It had an amazing day, so relaxing! We spent our time over a leisurely lunch, chatting and laughing as only two good friends can. Then the afternoon was spent shopping. Some lingerie from a small shop, that had raised no eye brows at two `girls’ giggling over sexy underwear. Some stockings, dark and sheer. A lacy matching pair of boy shorts, bra and suspender belt. From Next you helped me select a dress; one you felt that would show my figure of in a way to catch the eye. With my newly purchased brunette wig awaiting me in my hotel room and shoes, I had a feeling Julie would come to life this evening.

The journey back the hotel seemed to take for ever. The contents of my shopping bags demanding they be worn and my stomach tingling with anticipation, in a way unknown since my childhood Christmases.

We slipped into our adjoining rooms, where our female sides would be allowed to be dressed and pampered. Shower and then shaved. This was the first time I had shaved my legs. But also the first time I had shaved around my man hood. I knew you were not expecting that treat and I hoped, no I knew you, would be so very pleased. If I glad to claim a best feature, my legs would take that honour and I hoped they would please you. My make up was next and I remembered all the lessons you had given me. Foundation, eye liner, lipstick neatly edged, and my nails. I took Julies wig from its box and know once that was on, Julie would be taking over. I adjusted it and looked into the bathroom mirror. The face that looked back was pure girl.. She smiled with an anticipation that her first night of love could only bring.

I took my time to dress, enjoying the sensation of the nylon sliding up my smooth legs. The red varnish visible through the dark mesh. I fiddled to connect the clasps, a task I knew would be easier in the weeks ahead. The breasts you had helped me select and the black bra made me feel as if I was born a woman. The dress fitted as if tailored, how you had known my size so well? Next a pair of heels we had picked together. I had practiced in them, but now it was the real thing. I walked unsteady, but with each step towards the adjoining door I felt my confidence grow and with each step the ability to walk like as girl,

The adjoining door was shut, and on the other side awaited a night of passion that would see me as your lover, for the first time. That would see us as girl friends, and would bind me to you as only the offering of girls virginity can.

I tapped gently on the door. Your soft girl’s voice told me the door was unlocked.. I opened it and slipped through. You looked up from the settee where you sat, your impossibly long legs tucked back in a lady like way. Your hair and make up were perfect and your dress pure sensuality. Your eyes ran from my shoes up to my hair, talking each part of my appearance and knowing that it was all for you. That this was to be `our’ special night.

I walked over, feeling the nylon of my stocking brushing. The walk seemed to last for ever as my eyes looked at the beautiful creature that awaited me.

We sat said by side on the settee our stocking knees barely touching sipping wine. The conversation was relaxed and we talked about the path that had led us to this moment and place. The talk was easy but we both sensed what we knew awaited us. I talked on, maybe nervous, but you leaned in slowly, as your lips brushed mine. The conversation ceased as we kissed tenderly. I could feel you hands encircle me, and pull me closer. Our breasts touched and your tongue teased my lips. I could resist you no more than a moth can the light, and my lips parted. I could feel your moist tongue enter my mouth. My own tongue sought you out it to feel and sense it. What can I say of that kiss but it was all I had anticipated, and my arousal was testimony to that.

One hand remained round me still pulling me closer, and your other hand sought my stocking knee. I could feel it touch and slide slowly along as my legs yielded and parted. You slowed your path along my stocking thighs to savour the moment and to tease me. My man hood throbbing with the anticipation of your touch.

The kisses became filled with more passion and your fingers reached my panties. I let out a moan as I felt you hand touch my silk encased arousal. The pre cum making my situation evident to your touch. Your fingers sought to release my me over the panties waist pant and they touched the wetness that had seeped from in me. You withdrew your fingers and stopped kissing me. You ran your finger over my lips so I could taste myself and so you would savour me as we kissed again…

Your hand returned to its warm nest only just abandoned and I could feel you letting me free of the satin prison. Your fingers stroked the shaft, and I could feel myself starting to throb, your touch being like a gentle electric current. Your fingers started to stroke the skin as I finally came alive. My hands sought the same nest and you’re stocking legs parted in welcome. Your man hood was aroused and my inexperienced hands fumbled to release it. The size, wetness and warmth of it were all I had anticipated. But my attention was denied as you with drew my hands. A smile and I could feel my dress being lifted and my arousal brought before your eyes. A second smile and your red lips opened to allow your tongue to taste my wet head, Then they parted as you admitted it into your wet mouth that sank over it like a welcoming pussy. I could feel myself deep inside your mouth and your tongue touching me as your fingers sought my balls. A few strokes and a warm wet jet emitted from the head. You looked up and smile…Please my darling you asked me, Show me how much you love me, as my hands sought the hem of your dress.

It had been the night I had surrendered my virginity to my lover. A night of passion and such new experiences, I was unable to take them all in. The morning light shone through the picture window, and the sound of the shower running came from the bathroom. My lover and dearest girl friend was freshening herself up for the day that lay ahead. More shopping, maybe lunch out? I knew what ever the day was to hold, the memories would be memorable. Maybe I should have joined you the shower, to show you how much my heart loved you, your gentle loving hands and tongue. I smiled and recalled the touch of your fingers and the depth they had explored me. How my virginity had been offered to their expertise. I smiled as I straighten the seams on my stockings. I had experimented with panty hose and with hold ups, but I was an old fashioned girl, and felt stockings were the only thing a girl should wear. I stood and faced the mirror. The reflection showed how far Julie had come from the days of her mother’s underwear drawer. My hair was long and autumn blond. My first style had been a bob, but you had helped me choose a lighter blond wig, a straighter cut, and I remember you smiling as you told me how much more fun blonde’s had. You smiled as you had kissed me lightly and whispered” so much more fun my darling”

Now several weeks on I was the blond girl your guidance had made me. You had shown me how to improve my first clumsy efforts with make up, and had been patient with my reluctance to shave. But once I had surrendered to your razor and brush, I had to agree I felt so much less masculine and so much more you’re Julie. The reflection looked back and I saw a tall well dressed girl. A short red skirt, which I knew you liked on me. My preference for stockings made minis unwise, but maybe in future when we were alone, you would permit me to show my legs off, stockings, topped with a mini skirt. A mini I knew would make my legs seem so much longer, and allow your hands so much more freedom. My blouse was clean and crisp and I had taken great care in ironing it. My new boobs were nestled into my favorite bra, and I could see my cleavage. My Cleavage! God it felt so perfect.

I had lost all track of time and had failed to hear you emerge from the shower. Your hair dry and clean. Maybe I could grow my hair to a length where, like you I would no longer need wigs? You were wearing the bra and panties you had purchased yesterday from Marks. Stockings showed your legs off as you walked up behind me and pressed yourself against me, your arms wrapped round my waist. I could smell the cleanness of you, as your hands pulled me back into you. I could feel how pleased you were, that I was your girl friend, as your arousal’s head pressed itself against my skirt.

I could feel my legs weaken as I recalled how you had opened teased and explored my virgin pussy with your finger. Then, how you had taken my virginity with your dildo. How it had at first hurt, but a pain of anticipation and love. I knew you would never hurt me other than the demands love would bring. How you had filled me with that toy and how I had felt I was finally yours.

Now your arms held me close and I could feel your breath against my neck as your face pressed into my long hair, parting it. So your lips could kiss the back of my neck. I moaned with anticipation, as I felt you guide me towards the large settee. Your hands holding mine as you brought me to the back of the settee. You whispered how I was your girl and how much you loved me, as you gently raised my skirt. I could feel as your hands sought my panties, silk, a present from you. I could feel you ease the fabric apart and your fingers tease me. I leaned forward and bent over the settee. My pussy there for you, for you to enjoy. “My darling” you whispered as I felt to the tip of your arousal tease my hole. I could feel the smoothness of the lubrication, as you teased the head around the entrance. You circle my hole with the head, and gently applied pressure. Lasts nights pleasures had made me looser, and I knew the penetration of your cock into me for the first time would not be as painful, but none the less it would be the moment my I was finally your girl and your lover, for now and for all time.

I felt the tip apply gentle pressure before it withdrew a fraction. Then pressure once more, this time a margin deeper. I could feel my own arousal as your hands reached under my skirt to stoke it. You tip with drew, and then re-entered, a fraction deeper, with each time. Then the moment came, my erect cock stroked in your hands as your cock finally entered me, deep, fully and completely. I felt the length slide in, and my pussy filled, and your cock spasmed as my pussy was filled with your warm wet love juices.

Everyone who worked with Andy said he was a regular guy, good to know, friendly, happy and pretty normal in a boring sort of way.

He’d do all the things workmates do, meet up to go out for a colleague’s birthday, talk about sport or the news or the latest celeb gossip and go out for a beer after work – unless it was a Friday which was the one odd thing about him. Every Friday Andy would say “Goodnight, have a good weekend” and no one would see him again until Monday, which was odd as he didn’t live far away from anyone in the office.

Andy had a secret. He was a cross dresser and on Friday nights he’d go home, have a quick meal, shower and change into his alter ego, Candy. Andy was a slim 5’7 with short fair hair. Candy was a curvy, busty, redhead with long curls, standing 6 feet tall in heels. She would dress to go out on a Friday and then to the cinema or for a drink with girl friend in all the same places Andy’s workmates went but although they all noticed the striking redhead no one ever recognised her.

All weekend Candy would walk and drive round the neighbourhood going shopping, meeting girlfriends and generally being the single girl around town and then on Sunday night, she would shower, put away her clothes, underwear, fake boobs and shoes and be back to Andy ready for work on Monday.

The only thing Candy had never done was have sex and she was desperate to do this. In the evenings after work, Andy would spend hours on internet dating sites trying to find someone he could meet up with as Candy for that first sexual experience.

Then after months of searching, one Wednesday evening he found someone. And they were in the same town! The profile said they were called Peter and lived on the other side of town and were looking for sex. The picture looked familiar but Andy couldn’t place them so just thought it was because the town wasn’t that big and anyway Candy’s favourite dress hop was on that side of town so maybe he’d just seen Peter on the street.

He took the plunge, sending a message with a photo of Candy saying could they meet soon? Peter replied within minutes saying how pretty and hot Candy looked and could they meet that weekend and suggesting they go for a drink and something to eat wherever Candy wanted. This was too good to miss so Andy replied suggesting Candy’s favourite restaurant in town where she knew people so felt safe and saying Saturday about 8? Peter agreed!

Andy was distracted at work for the rest of the week trying to think of what to wear and what Peter would be like. Friday came and he said “goodnight” as usual and went home. He showered and became Candy but didn’t go out as normal. Instead she spent the evening trying on lots of different outfits for Saturday nights date. Finally she settled on one and went to bed.

Next morning Candy slept in late then got up and ran a bath. She shaved really closely all over including round her penis, testicles and her anus, just in case. When she was sure she was smooth and hairless all over she dressed in jumper and jeans and drove to her local salon to have her nails and make up done professionally. Tonight she wanted to be perfect! When that was done it was 5 o’clock. Only three hours to her first date.

She carefully sorted out everything she needed for the night, including an overnight bag just in case and got ready. First her breast forms, 38D she’d chosen tonight, then her favourite under wear; a purple satin bra and panty set with lace trim. The panties went over her “boy clit” which was carefully tucked and held between her legs with a gaffe. Next a matching corset to pull in her waist a little and accentuate her bust. Candy was getting hot just getting dressed! Then her favourite long red wig, that curled down round her shoulders and framed her face. She put on the dress. It was a figure hugging blue number that stretched nicely over her boobs, hips and bum and down to her thighs. Silver 4 inch peep-toe pumps on her feet, then diamante ear clips, a diamante necklace, ring and bracelet and her favourite little clutch bag. Lastly a little silver shrug jacket and she was ready to go.

She went to her car and put her overnight bag in, and then drove to town to park near the restaurant. She was a few minutes early but she didn’t care. She was feeling horny, looking gorgeous and was hoping for sex. She went in the restaurant and was shown to her usual table in a private corner and told the waiter she was expecting a male friend and ordered a drink.

A few minutes later she saw the waiter greet a tall, handsome man and point him in her direction. So this was Peter. He was tall, dark, fit looking and she finally realised where she knew him from. “Peter” was her boss’s business partner! What could she do? She couldn’t leave, there was no time and she’d have to walk past him anyway? She was trapped? Candy sat and waited hoping that he wouldn’t recognise her as he didn’t come to the office that often but she wasn’t convinced and was now really worried.

Peter came over and introduced himself, the shook hands and Candy nervously offered her cheek to be kissed. She felt Peter’s breath on her neck and flushed. He noticed “First date nerves Candy?” She nodded. “Well no need to worry, you look stunning!”

Candy relaxed a little at that. He didn’t seem to recognise her and he was extremely handsome and very pleasant and charming. The meal was lovely and they shared a bottle of wine and chatted like any couple on a first date. Candy was very careful not to give anything away when Peter talked about work but she was sure he looked at her differently then. The meal ended and Peter suggested they go for a walk as it was such a lovely evening and Candy, who was now really enjoying herself agreed.

They strolled arm in arm to the local park which was one of Candy’s favourite walks. In a quiet corner of the garden Peter stopped, turned her round and kissed hard on the lips. Candy responded and soon their mouths were pressed together. “Candy” Peter breathed, “I want you”. “I want you too Peter” she replied huskily. “I have a room booked in a hotel, let’s go now” he replied.

They walked as quickly as they could and went to Peter’s room. The kissed again and Candy unbuttoned Peter’s shirt, running her hands over his chest and down to his trousers. She did it expertly and surprised herself at how easily all this came to her. She quickly undid his trousers desperate to feel his manhood in her hand. She found a huge, hard, throbbing cock.

“Suck it Candy” Peter said, almost demanding it. She wanted this so desperately she went straight down on him kissing his shaft all over before taking the tip through her glistening red lips and all the way into her mouth. God this felt so good why had she waited so long? He was moaning with pleasure and fondling the back of Candy’s neck.

Then something changed. Candy felt Peter’s hand tighten on her neck and pull her forward onto his dick until it caught the back of her throat and she gagged. “Get up” he hissed harshly. “Lift your dress and bend over… Andy” Had she heard right, had he really said Andy?

Candy tried to hold her dress down and protest. “Don’t look so surprised my little fagot, I’ve known who you were since you replied to my advert. Now if you don’t want all your workmates to know you are a cock-sucking sissy you’ll bend over and take what’s coming”. She really had no option, Peter had all the power, so she lifted her dress, bent over the bed and pulled down her panties and gaffe. Her she-cock fell out of the gaffe fully erect, she hadn’t realised how turned on she was. “You’re enjoying this aren’t you?” he sneered. “Are you ready slut?”and he pressed his steel hard rod into Candy’s waiting anus.

She tensed and then screamed as he pushed past her ring, the pain was intense but her little girl-dick got harder still. After a few seconds the pain subsided and she began to enjoy the feel of his dick inside her ass, probing and pressing. She bucked and rode him enjoying the pressure insider her.

She felt him tense ready to cum and before she could help herself shouted, “Cum inside me, cum hard inside me, I’m your cum slut, fill me with your juice!” She bucked harder back on him making sure his prick was deep inside. She could feel her own cum rising in her balls as his pumping turned her on even more then suddenly he exploded deep in her ass and she felt his hot seed hitting her insides. She came too, her little she-cock pulsing in rhythm with his. She’d done it, she’d had sex!

But then the sinking feeling returned. Would he stay silent or would he speak out? She turned to him and asked “What are you going to do now Peter? Have I done enough for this to be kept secret?” He looked at her thoughtfully. “Well know my little cum-whore, that depends. Would you be prepared to do this again, whenever I want it?”

Was this a threat? Candy thought it felt like one but it also felt like an opportunity for more sex. She knew what she had to say and what she wanted to say. “Yes Peter, I would, whenever, wherever and however you want” she breathed looking up at him from under the fringe of her wig. “Then it remains our secret” he said. “Now, make me hard again”.

“With pleasure!” Candy purred.

Over the years as a Out bisexual guy I have always tried to keep Lisa my far more feminine side hidden away. I spent many years dressing and loved it but decided when I had to move to a new house share it was time for Lisa to go permanently.

Unfortunately as many other cross dressers and transvestites know that is far easier than first thought to destroy a side of yourself that gives so much pleasure.

And as for me I found myself in different ways by meeting many trans girls for no strings sex whenever I could, loving having a sexy trans girl to pleasure and be taken by in some cases.

Finally I settled by occasionally dating one sexy cross dressing guy from my hometown who enjoyed being treated like a woman. I loved our times together having hard dirty unprotected sex together and sharing ourselves with others as well at fetish clubs and swinging websites.

I had been asked several times by others if I dressed as well and on the odd occasion I would slip on a pair of stockings and stilettos for sex games but unknowingly this awoke my other persona Lisa the transvestite cock loving slut that I had tried to get rid of and this is where the story starts.

I found myself on online auction sites purchasing heels, corsets and short tight dresses to show off my tight body. By this time I was 32 and needed a full corset to give me the look of a convincing girl.

I managed on a budget to find a lovely black and purple satin corset, hold up seemed stockings, full brunette wig and 5 inch satin peep toe heels all covered by a gorgeous figure hugging satin mini dress that suited my new look perfectly. I now felt like a girl again and all though I did not have the confidence to be seen outside as yet so dressed in my room.

I so loved feeling like a convincing girl and when I was dressed in my male mode I just did not feel right anymore, I felt I had to confess to my addiction, my secret life.

I chose my best mate to do so as I knew he was bisexual as well, first off I showed him a picture I had taken of me dressed which I had on a profile on a transvestite dating website. He simply asked who she was and if I could set him up with her for some fun as he knew I was well established on the local swinging scene as a hung bi lad.

I agreed I could, but told him she was a trans girl and was well endowed as well. This really did not bother him. He did say he had never had sex with a trans girl but fancied her and wanted to fuck her, little did he know that girl was me, his best mate in drag.

I agreed to set him up on a date and told him she would meet him at a pub in town I knew was trans friendly. Fortunately he decided he had to leave after a one or so to go get ready for his date, the date that would change our friendship forever.

As soon as he had left I showered and started to apply my makeup and shape wear, squeezing my body into a tightly laced corset, stockings, stiletto heels and dress. By now I felt great but so nervous I near poked my eyes out more than once on my mascara brush due to my hands shaking.

After about two hours Lisa was finally ready to go and face the world for the very first time, I picked up my mobile a second number I kept for sex meets and text my friend to say I hope he has still up for taking me not only out on a date but deeply from behind later on. He soon text back saying he was definitely up for taking me out and maybe giving me what I wanted.

I knew he would be there for 8pm on the dot so I ordered the taxi for just before eight as I wanted to be late just like any girl. One thing I forgot about stiletto heels is unless you are used to the them then stairs are a nightmare as I soon found out trying to get downstairs to my taxi.

I slid onto the back seat trying to look glamorous and sexy and could see the taxi driver having a good look on the way. We soon arrived at my pub of choice in the towns gay district, a classy gay bar that did not mind trans girls using it to pick up guys. With that I passed the taxi driver his fare and a tip and with that he wished me a good night and said if you don’t get lucky give us a call and ask for mark. He was quite cute, in his late 20′s and well built but blatantly gay. I just smiled sweetly at him as now I knew I had been clocked as a trans girl by him.

I made my way through the crowds of hot gay guys and girls with a few trans girls on the pull to the bar area where I had told my friend he would meet Lisa. I wiggled my way over to him and placed a hand on his knee to which he turned to look and met my gaze.

I introduced myself as Lisa and he followed suit but offered me a drink which I was more than happy to accept. As I stood by his side on my 5 inch heels I felt his hand slip round my waist, I just adored being touched when im fully dressed and turned to face him inviting him to kiss me. As I thought he did not waste any time in kissing me full on the lips.

I took his hand in mine standing him up and we walked across the bar to where there is a collection of leather sofas for people to sit and chat amongst other things if you were discreet.

He followed making sure any of the other guys in the bar did not try to touch me up on my way, in fact one did but I did not respond I just kept walking and trying to wiggle my bum just enough to keep him interested in my tight backside.

When we reached the sofas it was very busy and I decided to ask him to sit so I could sit on his lap. He did not refuse and seemed to enjoy having me there, we just sat and chatted for a while exchanging the occasional light kiss. I knew what he wanted from me and he knew I wanted it to as I felt his cock stiffening in his jeans and prodding my tight bum as I turned to sit facing him in a me on top position. He moved his hands to my waist and complemented me on how sexy I was before asking can we leave as I really like you girl and I really want to satisfy your need for cock.

I knew this was coming and knew he was going to ask me to have sex with him but then the nerves kicked in. I replied yes lets go and grab something for me to suck on.

We left the bar and jumped into a cab outside and headed to my place, the minute I gave the address to the taxi driver I saw a look of confusion on my friends face but I sat with him saying nothing.

Within minutes we were back at my place and he said to me a mate of mine lives here, I think you know him. I agreed I did and had agreed to use his place tonight as he was out with another girl in town or in bed by now. This seemed to work for a few minutes til I opened the bedroom door and he saw my makeup and case I kept my dressing bits in and recognized it from all the times he had been round to visit me as a guy, his best mate.

I took myself over to the bed and sat upon the side patting the duvet down next to me trying to get him to come over. In the end he submitted and came over but suddenly would not touch me. He asked if I was who he thought I was and I just nodded.

I was so scared that I was going to lose a friend at that minute I started to cry and told him all about my dressing and my love of being a girl. I was shocked as he wrapped his arms round me and pulled me close telling me he still found me very sexy and would love to fuck me still if I wanted him to.

I went off to the bathroom to clean myself up and douche myself as I intended to take his hot spunky load deep in my man pussy. I so loved being fucked hard when I was dressed and played a totally submissive role to any guys who were lucky enough to get with me.

I went back to my room all clean inside and out and stood in front of him and unzipped my dress letting it fall to the floor and show off my lingerie. He got to his feet and removed his clothes and his briefs showing off his thick 7 inches of man meat. I could not hold back and pushed him onto the bed and dropping to my knees in front of him. I slowly slid my hands up his thighs eventually reaching his throbbing cock which I slid into my mouth and started sucking him deep and slow into my wet slutty mouth.

He laid there moaning with pleasure as my tongue darted round his impressive bell end, I could feel my own 8 inches was rock hard in my lace panties. I got to my feet and he sat up seeing me stood in my corset and lace panties with hold up stockings and a large 8 inch cock protruding from my panties, he wasted no time in sucking me while he slowly slid a finger round to my bum and massaged my man pussy.

Now I really needed cock badly and I slid my member from his mouth and got onto the bed along side of him, he turned to face me and started to kiss me. I was in fits of ecstasy feeling all my senses going wild for him. He soon asked me if he was going to have the pleasure of fucking my tight pussy and I simply smiled and moved onto the bed on my hands and knees begging him to rim my tight pussy.

Soon I felt his hot tongue lapping a my juicy man pussy and he reached through and slowly massaged my cock. I loved it and started to grind my pussy deep into his face as I adore being rimmed. He seemed to know what he was doing and I was aching for his cock in me, with that I pulled away from him and asked him to lay on his back for me.

He moved form his position behind me to flat on his back, his cock was rock hard and had a glaze of cum across its hood. I reached for the dressing table and grabbing a bottle of my favorite lube began to massage it into his cock and my pussy while slowly playing with my love hole trying to prepare it for his cock.

No longer could I wait for him to enter me as I climbed on top of him and slowly lowered my tight cock hungry pussy onto his cock inch by inch until I felt his balls deep in against my bum.

With that I began to slowly ride his meat in and out of my well stretched hole, he soon had his hands on my side encouraging me to ride him harder and harder til I was being bounced off his thighs and moaning with each deep push into my willing pussy.

Soon my thighs could take no more and I had to dismount his meat, but I needed more and I wanted his cum dumped deep in me. I moved onto my knees and held the headboard of the wrought iron bed frame. I instantly felt his large cock opening up my tight pussy again, he had the one of the nicest cocks I have ever had as Lisa and boy he knew how to use it.

Within minutes I felt like a complete slut again as I felt his full balls slapping against my bum as he drove his meat into me all the time calling me his little fuck slut.

I was loving being screwed so deep and hard but I felt his cock starting to throb inside me so I told him to pull out, he did and started to wank himself off thinking I wanted him to cum over me but I still wanted more so I stopped him and tied a stocking tight round the base of his cock telling him I needed more cock first.

I did not know how long he could last til I would have to release him so I pushed him back down onto the bed and mounted him again taking all 7 inches without hesitation. The look on his face said it all as he felt my anus clamped onto his hard throbbing cock. I knew what I wanted though and I began to bounce on his rock hard shaft harder and harder.

Within a minute or two he was begging me to let him cum so with one hand undid the stocking from round the base of his cock and slid all the way down his throbbing cock to his full balls. As I did I felt him spasm deep inside me flooding my anus with hot spunk, ream after ream of spunk shot up my pussy til it was running back out and all over his balls.

He collapsed onto his back on the bed and I slowly climbed off his now flaccid and cum soaked cock. As I did he thanked me adding wow thanks babe that was one hell of a good fuck. I had to agree but I was not finished yet as I had not cum.

I asked him to suck me again and he rolled to the side of the bed before sitting up and taking my cock in his mouth, expertly he sucked me deeply and slid a couple of fingers into my well fucked bum playing with my g spot and sending me into a huge orgasm and filling his mouth with my own spunk.

He tried to spit most of it out but I had bent down to kiss him and share my hot load from his tongue, we kissed for a while sharing my spunk and then both showered.

I thought I would just go back to male mode but he asked if he could stay overnight and take me again the next morning so I slipped into a silky teddy and panties and slid into the bed alongside him and fell asleep with his cock resting up against my anus and his arm tight round my waist.

I woke with him rock hard behind me and wasted no time in him sliding his meat into me again and fucking me senseless til he shot his hot load deep into me for a second time. After I got up from the bed and went to get washed and cleaned out.

Upon walking back in he was sat there looking shattered but told me he was glad we had done it as he told me he had always wanted to fuck me and me being Lisa was amazing as he fancied my alter ego as well.

That was not the last time he plundered my man pussy but that is another story for another time.

Lisa xxx

I am your typical sissy bottom guy who loves mature men. My proportions being large, club me into the BBW category so only the daring types can enslave me. Mature men in the age group 35-60 attract me. Only young guys with very huge dicks are an exception.

This is about a naughty adventure of mine which happened in a residential area in New Delhi. The hormones in me were raging and I was dying to get sissified. I called up my regular mature top and asked for a date. He responded with a yes but said that he had a top friend with him. I agreed for a 3some. As luck would have it, the person (who is also a top) who owned the place was at home. That made a 4some. We arrived at the place on designated time. I was sent to the bedroom to cross dress into a white skirt and a pink top. I had brought along my favourite black bra and panties along with stockings and a pair of heels. The owner’s wife’s make up kit was there in the bedroom so I used that. I dressed up and called them all in.

WOW, was there reaction on seeing me dressed up. They never expected a sexy fat whore in front of them. The ample proportions of my breasts and my huge ass cheeks sliding to and fro made their eye balls pop out.

I was made to serve them drinks. As they sipped on their chilled whiskies I slowly started unzipping them. These men were long and thick with manly bushes around the pelvic region. I started giving long licks to their balls. The man smell coming out of their cocks made them groan in pleasure. They started to get wild and rough. My head was held in firm grip and they started face fucking me very roughly. Their huge dicks were choking me. Tears came out of my eyes. I did not like being humiliated like that. I resisted and told them that I am leaving since they did not know how to behave with a lady. I called them names which further enraged them. That proved to be my undoing.

The owner of the place called his servant inside. Two of them grabbed my each of my legs and the other two my arms. I was thrown onto the bed. My hands were then tied with ropes to the bed poles. How helpless I felt at that time. I really was scared.

Then they roughly tore of my panties and my top. I was there naked and tied up. They started to undress themselves completely. I was surprised to see even the servant disrobing himself. It now occurred to me that I might be raped by 4 men.

Now, I had one dick mouth and a tongue in my ass hole. My nipples were pinched very badly. The dick in my mouth was fucking my mouth like a pussy. The man came very soon. My mouth became flooded with his thick cream. I could not drink it all so it was spilled onto the bed, my face and body. Meanwhile I had my asshole lubricated enough with all the licking. I do not know who but somebody applied a gel in my hole to lubricate it very well. I could not see my fucker when he inserted his thick penis in my tight ass hole. I was being mercilessly ripped apart. Another penis meanwhile had entered into my mouth and I was now being ravaged like a lifeless sex doll.

Soon I could feel my ass being filled up with thick semen. I could feel it dripping down my hole into my thighs and bed.

The 4 bastards fucked my ass and mouth one after another. They all fucked me twice. In total I was ass fucked 8 times that night. My hole was like a slippery wet tunnel. My whole body was drenched in semen.

Now they took me to the toilet where I was made to sit on the floor. I was confused but soon my confusion was eradicated. They all started pissing on my face, in my mouth and on my body. I tried to close my mouth but was immediately slapped and forced to drink their urine. When they finished, I was made to clean their dirty dicks. I could taste my own ass on their dicks.

They all laughed, called me a randi and left the bathroom. I lay there on the floor humiliated and ravaged. I wondered what will happen next. I felt my small dick; it was like a rubber band hanging down. Exhaustion overtook my senses and I drifted into semi-sleep.

What happened after that is something I am too ashamed to write. Next time maybe.


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You might want to read the first chapter for context…. On the other hand, you know what you’re in for here. I hope you enjoy the kink, baby.


I was back for more the next night. I figured that a blowjob from a pretty woman was worth the time, even if the pretty woman was Marion’s boyfriend, a feminine man dressed in lingerie. Her androgynous looks and lingerie made a difference. It did. I’d never let Steve suck me off, but Stevie? Stevie was pretty. She kneeled between my legs and looked exactly like a pretty flat chested woman sucking my cock. And Marion was very persuasive. I was enthralled with Marion and it was hard to say no to her.

Marion greeted me warmly at the door dressed in black high heels, black garter-less stockings, skimpy panties and a bustier with some sort of pattern running through it. She looked devastating.

“Hi baby. Mmm, you look good enough to eat,” she said, chomped her teeth like she was biting me and smiled and winked. “Come,” she took my hand, “Stevie is simply quivering with anticipation.”

Stevie was waiting at the window again, a barge slowly making its way downriver. She wore a multicolored silk robe, red stockings and high heels, she turned and white earrings and a matching necklace appeared. Red lipstick. Her shoulder length blond hair shimmered and she looked like a beautiful porcelain doll.

She let the robe slip from her shoulders and it flowed down her slender body and pooled on the floor. Stevie wore a red camisole with thin straps and red panties in the same style as before. White high heels.

Marion stood beside me, pulled my arm around her waist and said, “Isn’t she lovely. I’m so proud of her. Come dear,” she held a hand out to Stevie.

Stevie approached us and stopped, a little too close for social comfort. She put a hand on my chest and let it trail down to the hem of my t-shirt. She pulled it up and I let her take it off of me.

She kept her eyes on mine as she kneeled before me. She unbuttoned and unzipped my pants and pulled them down. She leaned in and nuzzled and mouthed my cock through my boxers and it felt amazing and I caressed her hair.

Stevie peeled down my boxers and I stepped out of them. She cupped my balls with one hand, wrapped her fingers around my thick cock and licked the sensitive underside and I moaned. Stevie sucked me and her tongue swirled around me and her hands were soft and firm, raking my stomach, flicking my nipples, gently squeezing and kneading my balls.

She sucked me. Marion had her arm around my waist, caressed Stevie’s hair and she talked. “That looks so good, baby. You like that thick cock throbbing in your mouth? I get so wet sucking it, watching you suck it. Are you wet? Is your little pussy leaking, Stevie? Mmm, you’re clit is so hard you might need to adjust it. Go ahead and adjust it, baby. You can rub your panties if you want. You can rub your little clit.”

I moaned with Stevie’s efforts and Marion talked. “You feel it yet? The contrasting feelings? The polarity of cocksucking? Such a submissive act and yet you hold all the power. Isn’t it a rush to the head? There’s nothing like a hard cock in your mouth, is there, baby.”

I was close and held Stevie’s head and I groaned and hitched and came in her soft, eager mouth. Stevie cleaned me, stood, gave me a shy peck on the cheek and ascended the spiral steps to the bedroom. She looked amazing walking up the stairs, her legs, her hips, her ass.

I took a deep breath, put on my underwear and shorts. Marion handed me my shirt and I put it on and she said, “I’d ask you to stay, baby, but I have to give Stevie a sound flogging and then a good reaming. She’s earned it, don’t you think? Tomorrow?”

I nodded and she walked me to the door, kissed me and left me breathless at the threshold.


Variations on a theme for a week or so and Stevie had yet to wear the same lingerie for each nightly blowjob, different styles, colors, patterns and materials. I didn’t know what most of them were called, but they looked fantastic on her. I became comfortable with a pretty, sexy crossdresser on her knees, my cock in her mouth, Marion looking on.


I arrived on time, knocked and Marion opened the door and handed me a glass of chardonnay. I took her in and she said, “You like?” She pirouetted. She wore a dark blue sheer lacy bra, cobalt she called the dark blue color, and matching panties, garter belt, stockings and high heels.

“Sizzling,” I said and kissed her, sipped the wine.

Marion said, “Special night tonight, baby. You’ll help me get off won’t you? I need you to help me. Tell me you’ll say yes,” She started unbuttoning my shirt.

When I was naked she handed me some cloth, rubbed it against me and said, “Put these on, baby. I’ve fantasized about seeing you in them. I get so hot and wet thinking about you in them.”

I held them up. It was a pair of cobalt panties, shaped like one of those bathing suits you see men wear on European beaches. Some stretchy material, very thin, not sheer, but not exactly opaque. “I can roll with this,” I thought. Especially if Marion got off on it.

I stepped into them and pulled them up. They were tight and I had to wriggle and shimmy them all the way up. The material felt good against my cock and it thickened.

Marion reached into the waistband and tucked my cock and said, “You make these panties look good, baby. Oh, yes you do.” She walked around me, her hand trailing on the panty and said, “Fantastic. Come.”

Marion led me into the living room, casual elegance, comfortable, and, as usual, Stevie was looking out the window at the river, a cabin cruiser making headway against the current.

She let her cobalt satin robe drop to the floor revealing her bra, garter and panties and she looked amazing, long slender legs, great ass, sexy back and shoulders. She turned and my heart beat faster and my cock stirred. She was breathtaking. Her blond hair shimmered in the low light of the room, daylight fading behind her. Her lingerie matched Marion’s. And the panties I was wearing.

Stevie strolled toward me. She stopped in front of me, took my hand and led me to the elegant leather couch. I sat on the extra wide seat and leaned back on the soft pillows behind me.

Stevie nudged my thighs apart and stood at the edge of the couch looking down at me, her silver dangly earrings glinting as they swayed. Her cock thickened and she adjusted it, toyed with it a bit under her lacy cobalt panties.

She leaned toward me, a soft kiss on my lips, my cheek, her voice soft in my ear, “Those panties look divine on you, they truly do. It’s a French cut. Marion and I have on cheeky’s.” She moved my hair and licked my ear, kissed my neck, sliding to her knees she bit and kissed her way to my nipples.

Stevie chewed and nibbled one nipple while toying with the other with her manicured fingers. She moved and bit and sucked and my nipples were throbbing and singing with delicious pleasure-pain when she abandoned them and kissed and nibbled her way down my stomach.

Her breath was hot on my confined cock and I was hard. Stevie mouthed me through my cobalt panties. She licked and mouthed and nibbled me and I moaned. She pulled the waistband away and down and tucked it under my balls. She pulled my cock toward her and looking me in the eyes she took me in her soft, hot mouth and I moaned.

She kept me in her mouth, head moving down then up, her lips firm, her tongue soft and caressing, hooked her fingers in my panties and pulled them down. I lifted my rear, thrusting into her mouth and we moaned together.

Stevie kept my cock in her eager mouth as she worked my panties down and off. She spread my legs and licked my balls and her tongue was flat and hard and rough on me and it felt so amazing. She went lower, as low on me as she could go then pushed my leg and I understood and I rolled over to my knees on the elegant leather couch.

Behind me, Stevie, stroked my cock, her hands soft and silky, she mouthed my balls and licked up and up and up and I felt her tongue on the sensitive nerves at my rear opening. I felt her manicured hands pry me apart and her tongue was hot and stiff at my hole. I moaned in joy when her tongue pierced me, stabbing insistently and entering me as far as she could with her probing tongue.

Urging me around again Stevie tweaked a nipple, stroked my cock and loved me with her mouth. I felt a slender, manicured finger work its way into me, followed by another and I moaned in pleasure and leaked cum into her mouth as she pressed and caressed my prostate. Stevie fucked me with her fingers and sucked me and stroked me and I moaned and moaned and shouted and grabbed her hair and came into her soft, tender mouth.

Stevie nursed me and cleaned me and to my surprise she put the panties back on me, sliding them gently up my legs and I raised my rear and she tucked me in.

Marion, sitting in a nearby chair, watching, clapped slowly and said, “Bra-vo, Stevie, bra-vo. I think that inspired performance deserves a little reward.”

Marion stepped over to us and held out a hand for Stevie to stand, two beautiful women in lingerie before me. She urged Stevie to sit next to me on the couch then took a seat beside her. Marion turned, put her arm around Stevie and trailed her hand down her front to her crotch and caressed her.

“Such pretty panties. That style looks good on you, Stevie, it truly does.” Marion pulled Stevie’s panties out and down and tucked the waistband under her smooth, hairless balls. In fact, I noticed Stevie was completely hairless from the neck down now that I took a good look.

I sat next to Stevie as Marion stroked her cock and talked. “Mmm, you’re getting fairly proficient at blowjobs. A little more practice and you just might be almost as good as me.” She stroked and palmed the head of Stevie’s cock and she moaned. “Are you liking the feel of his magnificent cock in your mouth? Do you enjoy the first taste of his slippery precum? Do you dream of opening wide and putting your pretty lips around his thick cock?” She stroked Stevie faster and she was breathing hard and as she arched and moaned and came Marion said softly in her ear, “Do you dream of more?”

Marion raised her hand to Stevie’s mouth and she cleaned her girlfriend’s fingers and hand. The whole scene was erotic yet discomforting.

Marion said, “You go get cleaned up, baby. I’ll see our guest to the door.” Stevie leaned over, gave me a quick peck on the lips, said, “Thank you,” rose and went upstairs.

Marion stood, retrieved my cargo shorts and squatted before me, her wavy black hair framing her pretty face. She put them on me and pulled them up my legs. She motioned for me to stand. Marion pulled them all the way up, over the cobalt French cut panties and buttoned them. She zipped me, deliberately putting pressure on my cock, and I thickened.

I arched my eyebrows and she said, “Keep them. My gift to you. You do look good in them, baby. And you can’t tell me they don’t feel wonderful against your skin, because I know.” I was quiet as she handed me my shirt. I put it on, we walked to the door, kissed, and she said, “See you tomorrow, baby,” and smiled and disappeared behind the softly closing door.

I drove home thinking about what had just transpired. I was wearing panties and had just sat next to a man dressed as a woman while Marion gave him a handjob.

I couldn’t help notice the pressure and the pleasant feel of the panties on my skin and cock as I drove home from Marion’s two-story condo overlooking that wide, deep river.


Three nights later I was wearing what Marion called a sweet cheeks. It was like a thong with a wide, lacy waistband. It was yellow. My cock twitched as Marion seated it firmly against my rear.

While Stevie went down on me, lovingly sucked and stroked my cock, pulled the yellow sweet cheeks off of me, put her fingers inside of me and sucked me and fucked me, I groaned and Marion, sitting beside me, talked. “Isn’t she lovely? So beautiful on her knees in her sexy lingerie. Do you ever think about it? After all this time? About what she’s feeling? The joy. The power.”

Marion caressed Stevie’s head, toyed with my shoulder length hair and said into my ear, “Do you ever wonder what it’s like to have a nice thick cock in your mouth? Growing to full hardness there, stretching you wide? Do you wonder what it feels like for a hard cock to start seeping precum while you suck on it?” I was close, breathing hard. Marion whispered in my ear, “Do you wonder what it’s like to make a man come with your mouth?” and I came and came and came and Stevie swallowed and swallowed and stayed on me and cleaned me and my breathing and heartbeat finally slowed. Stevie put the yellow sweet cheeks back on me, kissed me for a beat longer than ever before, said thank you and ascended the stairs.

I wore the panties home. Again.


A few nights later I was at the door saying goodnight to Marion, lacy cream colored boyshorts under my pants, and she handed me an opaque plastic box with handles that easily folded down allowing the lid to be removed. It was about the size of a shoebox. Marion said, “I’ll be checking tomorrow at work, just so you know. And if you’re a good boy I’ll give you a reward.” She kissed me, groped me and shooed me out with a wink and a smile.

Sitting inside my car my heart beat faster when I opened the box and, sure enough, it contained panties. A couple of dozen panties of all styles and colors and patterns. I drove home wondering about myself and trying to take stock of the whole situation. So far it had been fun. I was letting a guy suck me off, sure, but he was made up as a woman and was actually pretty, so it didn’t really feel like getting sucked off by a real guy. And now Marion wanted me to wear panties instead of my boxers. I guess the real question was how far I’d let Marion go. The truth was I wasn’t sure I knew.


The next day Marion cornered me in my small office and shut and locked the door. She had an excited, mischievous look on her face as she strolled over to me. She leaned down and began to unzip my pants and I looked down her blouse at her extraordinary breasts. “You’re peeking,” she said with a smile.

“Can’t help it, you have great tits.”

“Mmm, glad you like them. I like you looking at them, baby. And touching them.” She reached into my pants and smiled brilliantly and kissed me. She unbuttoned me and pulled the lacy panty down so she could fondle my cock. “You picked the salmon colored hiphugger, wonderful choice. And you get a reward for being such a good boy.” There in my office, on her knees, Marion took me in her mouth and made me come. Afterward, she tucked me in, stood up, fluffed her wavy black hair and shimmied her hips and said, “God, I got so wet thinking about you in panties, wondering if you had them on. I want you to fuck me tonight after Stevie does her thing. I want you to fuck my ass. Oh, god, I want you so bad.”

Marion left and I had to adjust my cock in the salmon colored hiphuggers. So that’s what the style is called, I thought.


Several days later Marion met me at the door to her two-story high rise condo. I stepped into her foyer and took off my pants and shirt, leaving on the red with black polka dots wide-side thong. She said, “Mmm, lovely. Just lovely,” and I might have blushed. She wore a white corset, sheer white stockings and white high heels. “Baby, I need you do something for me. It’ll make me sooo wet, and I know you like it when I’m all wet and slippery for you.” She kissed me and ground against me.

“What?” my voice was thick.

Marion produce sheer black stockings that didn’t need a garter. Thigh highs, she called them. “Put these on, baby, do it for me.” I took them in my hands. They were as light as air. “Say yes, baby, never say no to me,” she whispered in my ear and bit my earlobe. Somewhat numbly, I sat on a chair and started to pull them up but not having much luck and Marion said, “Here, baby, like this. You have to gather the fabric like this. Then you can put it on and easily pull them up. Helps to point your toes, too.” I did as she demonstrated and as I put my foot into a stocking she said, “Oh my, we’re going to have to do your toenails or else you’re going to snag and get a run sometime.”

I nodded and pulled a stocking up. It felt odd as my leg hair was pulled up as well. They came up high, not much below my balls. Marion kissed me and said, “God, that’s so sexy.”

Stevie’s hair was pulled back and clipped or something, but rested high on her head, emphasizing her long, graceful neck. She wore sheer, pale blue stockings, matching lacy panties and bra, dangly earrings and a darker blue beaded necklace and bracelet. Her stockings brushed against mine, a delicate whisper of a sound, as she stood before me. She adjusted her swollen cock and leaned down to me. Soft kisses on my forehead, my cheeks, my nose, and finally my lips. She stroked and fondled my panty covered cock and my breath quickened and my heart raced as I felt her tongue seek entry. She pushed in and our tongues swirled and I moaned and felt dizzy. Stevie broke away after a few long moments, worked her way down my body and with fingers and mouth and tongue made me come while my hands clenched her hair and I convulsed into her soft, hot mouth.

At the door, stockings and panties on under my trousers, I felt a bit numb. Marion hugged and kissed me goodnight. At the threshold she said, “You know, those stockings feel absolutely glorious, but you’ll never experience it with hairy legs, baby.” She blew me a kiss and gently shut the door.


Thanks for reading my story and I you enjoyed it. Please take a moment to vote and leave a comment. Let me know what you think of it.

You might want to read the earlier chapters for a bit of context…. On the other hand, you know what you’re in for here. I hope you enjoy the kink, baby.


At work people loved my shoulder length light brown hair with highlights. They loved my longer nails, now one quarter inch past my fingertip, as Marion dictated for optimum feminine grace. Not that they knew, of course. They thought it was because of the current ad jobs I was on, a hair care product and a fingernail product. In fact, they took to calling me PJ, for Pejic, Junior. I finally did the internet search and, surprisingly, they weren’t too far off.

But I knew different about my hair and nails, and what I wore under my clothes at work. And so did Marion. Each night, and weekends now, I was at Marion’s, shaved completely hairless from the neck down, made up and dressed as a beautiful woman, sucking her boyfriend’s cock and getting fucked with her strapon.

Marion had led me down a feminine path and I was afraid where the road would end. I was sucked into her world much farther and faster than I could ever have imagined. It was thrilling beyond words and yet utterly terrifying. I wondered if Stevie felt the same way.


I arrived at Marion’s two story condo a little after seven Friday evening. As usual, Marion handed me a glass, champagne tonight. I took off my shirt, revealing a pretty lacy teal colored bra. I took off my pants to reveal matching boy shorts and sheer thigh highs. By now she usually had earrings for me, bracelets, a necklace, and would put on some light eye shadow and lipstick on me before leading me to her living room overlooking the wide, deep river. Or to her bedroom.

“You look simply divine. That is such a sweet color with your hair and complexion. But we won’t be needing them tonight, baby. Tonight’s special. I’ve been so proud of you, baby, I want tonight to be so special.” She kissed me, leaned into me and reached behind me and unclasped my bra. She knelt and peeled down my panties and my cock thickened and she nuzzled it against her cheek and purred. Marion slid my stockings down my legs and the feeling as they whispered down my long, smooth, hairless legs was simply divine.

Marion refilled my glass, took my hand and led me up the black wrought iron spiral staircase to her bedroom. She was gorgeous in strappy high heels and sheer black body stocking and lacy black high-cut panties that showed off her slender, athletic build and magnificent breasts. Her wavy black hair was full and magnificent.

A slender figure with brilliant blond hair stood looking out of Marion’s bedroom window at the river beyond, a barge making its way slowly upriver. Stevie. Stevie wore a satin cobalt colored robe, sheer cobalt stockings and black high heels with an ankle strap. I imagined she had on a matching bra and panty set.

Stevie turned and smiled shyly, which sort of surprised me after all we’d been doing with and to each other. She seemed a bit nervous and it hit me and my heart beat faster and my cock stirred and Marion said, “That’s right, baby. It’s time for the next level in Stevie’s womanly pursuit. And you just have to help her, isn’t that right.”

Stevie untied the robe’s waist belt, gently moved it from her shoulders with manicured nails in a feminine gesture and let it drift down her body and pool at the base of her five inch high heels, her five inch fuck-me’s. I gulped and my heart raced. Backlit by the window Stevie stood there in a sheer lacy cobalt colored bra, matching thong, stockings and high heels. Her slight frame, her slender body so alluring, her brilliant blond shoulder length hair framing her lovely, delicately featured androgynous face. Light makeup, eye shadow, lipstick. She could easily pass in public as a beautiful, desirable woman.

She walked over to me and stood in from of me, taller than me in her heels she looked down at me and lightly stroked my cock with a manicured hand. “Are you sure?” I asked and Marion affirmed it and bade me remember the Golden Rule.

Stevie kneeled and blew on my cock, her breath warm, moist. She licked it, mouthed by balls and closed her hot lips around my cock and I moaned and let her love me. After a minute or two, before my knees buckled, I urged her up, led her to Marion’s huge bed and she crawled upon it and lay on her back in the middle and her brilliant blond hair fanned out enticingly.

My heart was racing as I lay down beside her, slipped my arm beneath her head and leaned over and kissed her. Our tongues sought each other and we kissed and I caressed her lovely face and my hand drifted down to her bra and I fondled her nipples. I toyed and twisted Stevie’s nipples and she moaned and I’m sure they stung and throbbed deliciously by the time I let my hand drift down her body, across her flat stomach.

My hand drifted over the front of her lacy thong and she moaned as I caressed her hard cock. I caressed and fondled her hard cock and she groaned when I bit and tortured her sensitive nipples. I chewed on her nipples and stroked her panty covered cock and kissed my way down her lovely, slender body.

I mouthed her cock through the panty and my heart thundered at the thought that I was a cocksucker and was about to fuck this man. I peeled her thong down and off and he moaned when I took him into my soft, hot mouth. I savored the glorious feeling of that thick hot cock as I rode it down, then up, so hard and wide in my eager mouth. I sucked and it throbbed in my mouth and I felt the veins with my tongue and he moaned and my fingers toyed with his rear opening.

Stevie was slick and he’d been prepared and he moaned and caressed my hair when I slid two fingers inside of him. I sucked him and fucked him with my fingers and my jaw was tired and my cock was leaking precum by the time I moved between those slender, stocking covered legs.

I was on my knees and Stevie raised her stockinged legs wide and high, her high heeled toes pointed toward the ceiling and I smiled because that’s an important style detail for Marion; a woman getting fucked on her back should point her toes toward the ceiling.

My cock was iron and poised at Stevie’s opening, her cock hard before me and I leaned in and pressed against her. Gently, insistent, I pressed and her rings released and Stevie groaned and I was in that hot, tight channel. I pushed gently on and I moaned at the tight heat and Stevie groaned as our flesh met and I wriggled my hips against her taught body.

On my elbows, “Oh god, so big,” in my ear. I slowly drew out and pushed back in. “So different,” she gasped. I did it again, and again, picking up speed and power. “Yes!” In my ear. Stevie’s legs wide and high, I drove into her and kissed her and toyed with a nipple and she moaned into my mouth.

Without withdrawing I put her on her hands and knees and grabbed her hips and slapped and slammed into her and wondered if the passengers on the cabin cruiser motoring down the river could see us. Stevie was moaning and wailing with each thrust, pushing back, her hair flicking. I reached around and stroked her leaking cock and she moaned, “Oh god.” I held her shoulders and rammed into her and her hot ass felt like a velvet vice on my thick cock.

Stevie rasped, “Oh god, I think I’m going to come.” I tossed her on her back again and snapped my hips, speared into her, side to side, in and out, a repetitive staccato rhythm and she wailed and moaned and thrashed and convulsed and I felt her ass clench and felt her cum on me and it sent me over the edge and I spasmed and shouted and came deep inside of her lovely tight ass.

I lay on Stevie, my breath slowing, her cock between us, wetness there. “Oh my god,” she said, her arms and legs wrapped tightly around me, “Oh my god.” I swiveled my hips gently and loved the feel of her tight ass grasping and clenching my cock and she moaned and my cock was hard.

I rolled us over and Stevie rotated her hips some before rising, her hands on my chest. Her hair swayed as she straddled me and gyrated, moving on me, grinding on me and snapping her hips and I moaned at the pleasure. I grabbed her hard cock and stroked it and she moaned. Stevie leaned down and kissed me and I punched my hips up and flesh was slapping and she rolled me over and said, “Fuck me” and I put my hands under her knees and pinned her down and drilled into her with everything I had and as hard and as fast as I could and we were sweating and grunting and moaning and she played with her cock and her earrings swirled and I cried out and arched and came deep in her tight ass and through the haze heard her shout and felt her ass clench tightly and I fell on her as before and we were limp.

I gently slipped out of Stevie’s amazing ass and we lay side by side getting our breath back. Marion handed us a glass of champagne and we sat up and she said, “Brilliant darlings. You were wonderful Stevie. I told you he knows how to use that thing. I hope you were taking notes, baby.”

“Oh my god, Marion,” Stevie said, “It was wonderful. Better than I imagined.” He looked at me, placed a manicured hand on my thigh and said, “Thank you so much. A first time couldn’t have been any better. Oh my god.”

I smiled, nodded and ran my fingers through my hair and sipped champagne.

The next day and for the next week Stevie and I would gleefully, enthusiastically suck cock and I’d fuck her hot, tight little ass while we were made up and dressed as a pretty woman in lingerie. One delightful evening I was wearing a lovely lavender camisole-garter outfit with matching stockings, red fuck me’s with a silver heel, big hoop earrings and bangly bracelets. Stevie was on her back beneath me, my thick cock deep in her garter framed ass, Marion behind me, her thick strapon sawing in and out until we all came and were complete. It was such decadent loveliness my cock thickens and I still swoon at the thought.

And that’s how it went until the next weekend.


Late at night I lay in my bed, the one on which Marion fucked me with her strapon weeks ago, before she took me on a journey. I was having trouble falling asleep.

Marion. Oh, Marion. So pretty, so sexy. That raven haired woman had me under her spell and I was lost in her aura of femininity. In months, mere weeks, Marion had led me down the rose petaled path and I’d gone from cargo shorts, boxers and flip flops to cute skirts, lacy panties and strappy high heels. I was shocked to discover how much I enjoyed wearing lingerie and feminine accessories, and how vulnerable yet powerful they made me feel. How the tug of my earrings and shoulder length light brown hair with highlight brushing across my shoulders made me feel so feminine, made me want to fuck. How I loved a thick hard cock filling my mouth and how I soared with pride making a man moan in pleasure.

I had no awareness that I had it in me, had never even thought about it before Marion brought it out in me. The feminine, the desire to lay on my back in makeup and sexy lingerie while a strapon filled me and thrilled me, or to be on my hands and knees with a hard cock in my mouth while getting fucked by Marion’s strapon and loving how my body felt rocking with her thrusts, my hair swaying and earrings swinging and my cock jerking to the rhythm of the fuck.

But Marion. Oh, my Marion. She saw something in me. Something deep inside of me that led her to believe I’d succumb. And I have. So far. Oh, I knew what the next step was. And I had a pretty good idea how, as well. What I didn’t know is if I’d go through with it. On one hand the thought of it was exhilarating; on the other hand it was terrifying.

Who am I that I even think of this? What am I that I have let this happen, have given Marion such power, such influence? How far would I let her go? I didn’t have an answer.

I let my hand drift down my flat chest, across my flat stomach and caressed myself through my lime green lacy hiphugger panty. My cock was hard.


Friday. I arrived at Marion’s after dinner, knocked on her door and she opened it and handed me a glass of white wine. I smiled as she unbuttoned my cargo shorts and took delight in my black and white striped lacy ckeeky.

She took my hand and led me up the wrought iron staircase to her bedroom and then to her vanity where she sat me down. Marion quickly painted my fingernails and toenails a dark red. “Look at you!” she said. “I barely have to do anything to get you looking like a high class runway model.”

She picked up some tweezers and made sure my eyebrows were perfect. “You shaved this morning like I told you to?” I nodded. I’d shaved everything from the neck down and was still tantalized by the way the air flowed over my skin. “Good, baby, real good.” She began to apply eye shadow, light mascara, a light touch with a brush on my face. “That’s good because tonight is a special night, baby, real special.” My pulse quickened.

Marion worked on my hair, brushing, arranging, spraying and said, “Have you figured it out yet? What tonight brings? You are most impressive, baby, you’ve gone the fasted the farthest and you’re ready.”

My heart was in my throat when Marion presented me with the cobalt garter slip. “Slip this on, baby.” It was sheer, lacy, thin shoulder straps and the garters had red ribbon over the tabs. It kissed and caressed my skin as I slid into it and it hugged my body, the hem ended low on my hips, a couple of inches above my cock. Red material in the shape of quarter moons under where my breasts would be, as if cupping them. Marion handed me dangly earrings and I out them on, leaning my head this way, then that. “Good girl. You should always put on your bracelets then earrings before you put on your stockings and shoes. Remember that. That way you slip into your femininity with more grace and ease.

My earrings tugged and my bracelets clinked as I quickly gathered a stocking in a practiced manner, leaned over, pointed my and swept the luxurious fabric up my long, slender leg. I gathered the other stocking and my cock thickened and I almost moaned at the glorious feel of its caress and tickle as I pulled it up and up an up and fastened it in that feminine twist of my body.

Marion gave me strappy dark red five inch high heels with an ankle strap and I put them on and closed the strap and they looked so sexy on my feet and I was glad to see they matched my nails and the ribbon accents on my garter.

I drank more wine and Marion refilled my glass with the bottle she’d bought upstairs. She handed me a lacy cobalt bikini panty and I stepped into it, pulled it up and tucked myself in.

Marion turned me to the mirror and yet again I had been transformed into a strikingly beautiful woman. She raised her glass in a toast and I clinked her glass with mine and my breath quickened when she said, “We have to get you ready. Bend over, baby, put your hands on the counter.”

My heart thumped inside my chest as I looked at my reflection, me and not me, a pretty woman. “Tonight will be your special night. All about you, baby. A sexy woman ready for the next step.” She peeled my panties down below my rear and I felt her soft hands on me. “You’ve flown so high and so far so fast and there’s only a few more steps to go before you’re all the woman I could ever want.” Fingers penetrated me and I moaned. Cool wetness and my heart pounded as she lubricated me, prepared me for what was to come. I was sacred but thought that I wasn’t fighting her so I must want this. Right?

“You know, I was just teasing about Stevie not knowing how to fuck. He gets off on that sort of torment, but he’s a fine swordsman, baby, I know he’ll treat you right.” She lubricated me and wiped me, pulled my panties back up. “There now, have some more wine, Steve will be here any minute to take care of your wet pussy, baby. I know you’re eager.”

From somewhere, “I don’t know, Marion…”

She put a finger to my deep red lips and said, “Shhh, not another word. You know you need to say yes, baby, never say no to me.”


“Don’t be scared. Don’t be scared to let this happen. Because you’ve known all along it was going to happen. When you first let Stevie take your cock in his mouth you knew. You knew when you put on that first panty. And last week you took a major step and I was so proud of you when you became my little cocksucker.” Marion brushed against my cock and I moaned. “All along you’ve known that a real woman takes cock. She takes cock in all her holes, baby. And you’ve only got one to go, so what’s the big deal?” She smiled and my cock twitched.

I knocked back the almost full glass of wine and Marion smiled and took my hand and I followed her into the bedroom. She handed me a red silk robe and I put it on and it felt glorious. I was so nervous standing at the window overlooking the slow flowing river, so wide and deep, a sailboat running downriver.

I’d done so much so fast had it really only been few months to go from only thinking about pussy to actual cocksucking? And now this? I looked down at myself and felt the tug and sway of feminine things, saw my high heels with the ankle strap. Marion told me a real woman wears high heels with ankle straps when she gets fucked so her shoes wouldn’t fall off and my heart suddenly hammered. Could I go through with this? Did I even want to? I was here, wasn’t that answer enough? I was so scared.

My thoughts were interrupted by a noise and I turned away from the never changing river. Steve. Wearing baby blue boxers. His brilliant blond hair pulled to a ponytail and tied at the nape of his neck.

He walked over to me and the roar in my ears was immense and I thought my heart would leap out of my chest. Delicate features, slender body, he was so handsome. He leaned in to kiss me and I felt his tongue pry my glossy lips open. He slipped his arms around me and pulled me to him and I felt his bulge press against mine and I quietly moaned and I knew I was going through with this and I was terrified. I was exhilarated.

I pushed him back and untied my robe. I shrugged it off my shoulders and felt it whisper down my body. “You are stunning,” Steve said, taking me in as I stood there in my sheer, lacy cobalt garter slip with red accents, lacy cobalt bikini panty, dark red five inch fuck-me’s.

I reached out and ran my dark red manicured nails down his chest, lower and felt him through his boxers. I leaned over and bit a nipple and he moaned. I fell to my knees, I got down on the floor, I looked up at him and he looked at me with loving eyes and I pulled down his shorts and took his cock into my soft, eager mouth.

I swooped down on his cock and it grew thicker, harder and it pleased me that I made it grow. I felt his veins and crown and urethra as my tongue and red lips moved over and around that cock so thick and hard in my mouth, and my bracelets clinked and my hair caressed my shoulders and my earrings swayed heavily as I tasted precum and heard Steve moan.

Steve gently urged me to my feet and I was a taller than he in my five inch fuck-me’s. He guided me to the bed and I lay down, on my back, in the middle of that huge expanse.

He lay beside me, looked at me, then at Marion sitting in a chair, legs crossed, sipping wine, dressed in a short, pink robe. Steve trailed a hand across my cheek, down my chest. The toyed with my nipples and I lay there and trembled. He leaned down and kissed me and I shot my tongue into his mouth, letting him know everything was okay. He touched me and I moaned.

Steve kissed my nose, my eyes, my forehead, my cheeks, worked his way down my neck and to my breasts. He played and toyed with my breasts and pinched and chewed my nipples and I moaned and had to adjust my hard cock in my lacy panties. I wanted to run my fingers through his thick blond hair so I released it from the band and he shook it loose then tugged on my nipples with his teeth.

This is a story about my first time with another man, so if that makes you uncomfortable, well, frankly, I don’t care. Don’t get me wrong, I wasn’t under age or anything at the time, I was 20, but some people, for some reason, don’t like that kind of thing. Personally, I find it hot as hell (N.B this is entirely fictional, but hopefully it’ll happen before too long).

Isn’t the internet a wonderful thing? Just last week I was another lurker, searching the web aimlessly for stuff to get off on. Now I’m a fully fledged knickers wearing cock sucker. I’ve been getting off on tranny porn for a good long time now, but recently (about a year ago know I guess), I started getting off on pictures of cross dressers, men wearing frilly knickers, bras, stockings, dresses and make-up. I don’t know why or how it started happening but one day, there I was pre-cum flowing like a leaky tap, a video of a foxy little cross dresser sucking off another. I’ve got off on that kind of thing so much, that the reservoir started to run dry and I began wondering where to turn next, that is when I discover cross dresser on man sex, even man on man sex.

I started to get more and more curious. These guys and girls, when their partner cums on their face or in their mouth, seem to enjoy it quite a lot, so before too long, my legs were up against the wall and my own spunk spraying all over my little slut face. Next I started to explore cross dressing myself, wearing knickers, bras, stockings and so on (I’m dressed in a cute LBD right now). And finally, bring us to the present, came anal, through the little gift to myself of a big, thick dildo. That was a good night, dressed like a slut, forcing a big fat member into my tight virgin ass.

Anyway, the net is truly a wonderful thing, without it I would never have got this far, the point of now having experience what so many men, myself once among them, have dreamed of, sucking a bit fat penis and having its warm seed blasted into my mouth.

The guy I met through a cross dresser personal site, I had recently uploaded a couple of new pictures of myself dressed, quite frankly, like a right little slut. One day, out of the blue, I got a message through the site, saying something along the lines of, ‘Hi, gorgeous, I’ve just seen your pictures and wow, I’d really love to get together with you some time. I’ve got a friend who has a place near you, we could hook up during the day. Looking forward to hearing from you, Kirsty’.

Needless to say, I checked out her profile before I replied and she was really hot from what I could tell (I always find people who find me attractive more so). I sat staring at the pictures for a while psyching myself up and replied, ‘Hi, I’d love to hook up with you some time babe, but it would be my first time so I’ll be nervous and everything so be patient with me. But yeah, I’m really looking forward to it, hope to hear from you soon, kisses…’ I realised I need as girls name for my female persona, in fact, it seemed quite strange that I hadn’t come up with one yet. I thought for a while and eventually came up with… ‘Clea’.

We arranged to meet the next week and I couldn’t wait, jerking off every night to fantasies of sucking Kirsty’s cock, having her seed in my mouth. I started eating my own every night to get used to the taste and make sure that, unlike when masturbating, I don’t pull out after unloading.

In preparation I went on a shopping trip. I got my self a bra, some new thongs, some fishnet stockings, and some make up (only lippy and mascara, I’m a poor student) and began practising putting it on in preparation for the big day.

The big day came. I arrived at the meet about five minutes early, with a pair of knickers and the fishnets on underneath my jeans. I given Kirsty details about how to recognise me. And after the five minutes passed like an eternity a guy came over a sat next to me. He looked about 30-35 years old, short hair and blue eyes. He looked at me, I looked at him and he said, ‘Clea?’

We shook hands and spoke a little while I subtly tried to check him out. He seemed to be enjoying the fact that I was clearly attempting to size up his cock through his jeans. We spoke for about 15 minutes before he said, ‘Shall we get going?’ I agreed and followed him back to his car. I was still pretty nervous, as I sat in the passenger seat and seeing I was almost physically shaking, he leaned over and kissed me. It was strange being kissed by a man, but not at all unpleasant, in fact, I was really getting into it, it felt great being so submissive to his will. He took my hand and placed in on his crotch, letting me feel his cock through his jeans as we kissed. It felt huge through the denim and I just wanted to lean over and wrap my mouth around it there and then. I went to slip my hand in side his jeans and he broke the kiss, saying ‘not just yet, baby’.

We drove off and soon arrived at the ‘love nest’, the caravan of a friend of Kirsty’s who was also a cross dresser. We went inside and Kirsty patted me on the ass and told me to go and get dressed in one of the bedrooms. I did so, slipping out of my jeans and shirt, and into my bra. I opened the closet and picked out a slinky little dress, as we had agreed I’d burrow one her friend’s dresses. I then started to fixed my make-up trying to make as good a job of it as possible. And, just as I was finishing Kristy call to me, ‘Are you ready, Babe? You can’t stay in there forever.’

‘I’ll be out in a minute,’ I replied. I checked myself out one more time in the full length closet mirror and, satisfied I was about as hot as I was going to get, stepped into the main part of the caravan, sharing, for the first time, my female side with another person.

She was looking gorgeous too, wearing a cute top and a leather skirt, as well as fishnets. She patted the seat next to her and I went over and sat down. She gently stroked my arm and told me, ‘Clea, you look amazing… I could just eat you up.’

‘You scrub up pretty well yourself, beautiful’ We started kissing again and I was a whole new sensation kissing lipsticked lips with my own lipsticked lips and I loved it even more than when we kissed as men. She ran her hand up my stocking clad legs and squeezed my ass under the skirt of the dress. I felt myself growing, straining against the material of my knickers. I rolled over, so I was straddling her and started kissing her all over the face and next, slowly working my way down her body.

Before long I was on my knees in front of her kissing her legs and feet. She stood up and I was faced with the bulge in her outfit. She pulled me up and we kissed again, she unzipped my dress and whispered in my ear, ‘Lets see some skin’, I wriggled out of the dress as it fell to the floor again we kissed as she undid her own skirt. She sat back down, and I fell to my knees, faced again with the bulge, this time in a pair of cute purple knickers. I hooked my hand around the waist band pulled them down, revealing her cock. I was beautiful, about 8 inches long, a bulbous, juicy head and I could just about fit my hand around it, as I found out as I started to stroke it. She was soon hard. It was strange, feeling another cock, like but unlike my own, hard and soft at the same time.

I saw a drop of pre-cum appear and gladly licked it up. Still slowly stroking her I wrapped my lips around her head and licked at the underneath. Kirsty moaned with pleasure. I was soon working it like a pro, licking and kissing it up and down, caressing her balls and generally making a mess of myself with a mixture of my own saliva and her juices.

Before too long Kirsty breathing got heavy and fast and she said, breathlessly, ‘I’m going to cum baby, where do you want it?’

I pulled her cock out of my mouth with a pop and said, ‘cum in my mouth,’ before diving back on. She groaned with pleasure and suddenly my mouth was full of spunk. I pulled off her again and spray after spray of spunk covered my face and chest, a few ropes even ending up in my hair. I swallowed what was in my mouth and we kissed again. I was in heaven. I could have stayed in that moment forever. But something else was calling for attention, my own throbbing member, I’d never been so hard in all my life, pre-cum was practically flowing out of me as Kirsty picked me up and wrapped her lips around me.

I was so hot already I soon came and Kirsty took in all in her mouth, sat back down next to me and kissed me, forcing my load in to my mouth. I gladly swallowed. We kissed and cuddled some more, Kirsty slowly feeding me the spunk that covered my face and chest from her fingers.

Later that day I lost another kind of virginity, but that is a whole other story.

*Sigh*, if only…

Kevin was your prototypical mid 20s guy. He had a decent job and lived on his own. He had good friends and whilst he was single he didn’t find any problems getting what — or who — he wanted in the bedroom. However he had long been fascinated by glory holes and by being serviced in them but by being the one servicing.

He was convinced he was straight and loved having sex with women. He was disgusted by the thought of being with a man in the bedroom but yet he watched so much glory hole porn and always found himself imagining that he was the girl and not the guy.

For years this had gone on but he had never done a thing to address his kinks. One day he was getting off on watching sissies sucking of guys in a glory hole and his doorbell rang. He stopped and answered the door and his long time friend Laura was there. Kevin had forgotten she was coming round to go to the football so he invited her in and said he’d take a quick shower and be ready in ten minutes.

Kevin showered and then remembered he hadn’t turned his PC off. He came out of the shower and was happy to see Laura was busy in the kitchen making a cup of tea. He signed a breath of relief and they went off to the game.

He thought nothing of it and life continued as usual for several weeks and had long forgotten about this possible situation until he came home from work one night and found a note in his letterbox.

I know your deepest darkest secret Kevin and if you want to experience what you really want then you’ll do as I say. To let me know you are interested put an ‘X’ in your window and I’ll give you further instructions.

Kevin knew this was a reference to his favourite sci-fi show but wasn’t sure who knew and more importantly couldn’t be sure of exactly what they knew but he was certainly going to find out.

The ‘X’ went on to his bedroom window and he awaited further instructions. Days went past and nothing and he just thought it was a crank letter but a fortnight later he came home and found another note in his letterbox.

‘So you are prepared to become the sissy glory hole whore that you want eh? Well now I know I’ve set up a scenario for you to become just that. At 7PM you are to be dolled up in the most slutty clothing you can get hold of and make yourself up to look like a whore. Use YouTube for inspiration on how to do your make-up.

‘You will drive to the car park outside the Lake Country Park and lock up your car and then you will walk the red trail footpath to the car park on the other side of the lake. It is very public but late at night very few people will be around so you will more than likely not be seen however I need to know you are serious.

‘Should you complete this task you will find a white Ford Transit van parked in the far corner of the car park and you are to knock on the window of the van. When the driver rolls down his window just look at him and say ‘I’m a sissy whore…get me out of here’ and I’ll make your dreams come true. You’ll be safe at all times and you will be returned home by 8PM on Sunday night so you can go back to your humdrum life. If you do not show up then you’ll never know who I am and I’ll never offer you this chance again.

Kevin read this letter over and over again and he only had two days to decide what to do. He changed my mind many times but when he got in from work on Friday evening he was fully prepared to go through with it.

Jumping into the shower Kevin shaved and got rid of all his body hair. He had a school girls uniform that he thought was slut personified that he put on before doing his make-up to look like a proper tart. Quickly looking in the mirror and he saw a person staring back at him of someone he’d want to suck him off and quickly jumped in his car and drove to the arranged car park.

Getting out of the car he took a big breath in and noticed the place was deserted before exhaling and checking with himself that he wanted to do this. Kevin had decided not to wear high heels which was a decision he would come to regret as he walked quickly along the path looking out for anyone but no-one was about.

He got to the car park but saw no vehicles there. He checked his watch and saw it had only just gone 7:15PM. He stood there wondering what to do and if anyone was coming and what to do if anyone turned up and saw me. After what felt like hours but was actually just 15 minutes a white Ford Transit drove in and pulled into the farthest car parking spot.

Kevin waited a couple of minutes before plucking up the courage to go over and knock on the window. He knocked on the window and the window came down and looked in and said, ‘I’m a sissy whore…get me out of here.‘ The driver looked me up and down and said, ‘you’ll do but you need a lot of practice.

Kevin stood there for a few seconds and then the doors of the transit opened up and two men rushed out and gagged him with a penis gag before handcuffing him behind his back and bundling the sissy into the back of the van.

At this point Kevin was wishing that he had ignored the letter. He was genuinely scared. No-one said a thing as the van sped off. Kevin feared he might die but before he could get a sense of what was going on the van pulled to a stop and the two men opened the door and told the gagged sissy to get out and walk to the door of a house.

His heart was pounding faster than it was when he had run the London Marathon the previous year but he had no choice and he knew that. The door opened and he was instructed to go in. Inside was a vixen with stunning long ginger hair who was wearing a mask. She nodded at the guys and they left and then she spoke.

So Kevin you want to be a sissy whore. Well this weekend my friend you’ll be the sissiest whore in town. It is 8PM now and for the next 48 hours you are a sissy whore. That is all you are. You can stop this at any time but if you do then you’ll just to left by me to fend for yourself and look at you — if you were left like this I’m pretty sure whoever found you would treat you like a whore. With me you’ll only suck cock. Without me who knows what anyone would use you for?

‘I have decided that as you are new you’ll be eager but pretty sloppy in giving blowjobs. So I have put the price on you at £10 a blowjob and you have to swallow to get paid. Your goal is to earn £480 in the 48 hours which as you’ll have worked out is an average of one blowjob an hour.

‘You’ll be taken from here to a fetish club where there are lots of open minded people. At midnight you’ll be taken into the bathroom and locked into the toilet cubicle with a glory hole where you’ll have four hours to earn as much cash as possible. Before then you’ll have to drum up business in the club and tell people who you are and what you are there for.

‘As for tomorrow you’ll have to wait and see. That depends on how much you earn tonight. If you make your £480 total then you’ll be rewarded by getting to find out who I am and I will let you go back to your old life if you want to. However if you have enjoyed your experience I would be interested in you being my partner as I’ve always wanted a real sissy because I get the best of both worlds. An obedient partner who’ll do what I say in the bedroom and worship me in every day life.

So are you in or do you want to walk out of that door right now?

Kevin tried to say that he was in but the gag was still in and he couldn’t take it out. She laughed. Kevin was desperate to find out who this stunning woman in a black latex catsuit with cascading red hair was. At this point she came over and added two further points.

I notice you haven’t worn any high heels which is not very slutty of you. I shall lock on a pair of my 5” high heels around your ankles. As a punishment for not wearing any you’ll not be freed from until 8PM on Sunday night.

‘Secondly as a whore you’ll want everyone to know clearly what you are to help you get paid. Here is something I made especially for you,‘ and she pinned a badge on Kevin. She unlocked his hands and gag and told him to go to the bathroom and freshen himself up. Kevin scurried to see what he looked like.

The first thing Kevin saw was the badge which was like a name badge ‘Sissy Whore Allyson‘ are the words that glare out at him but the words ‘Glory Hole Whore’ were above them and below them was the slogan ‘Swallowing cum so you don’t have to!‘ Kevin felt more humiliated by that than he had anything else so far. He touched up his make-up and walked back into the living room.

There he was told to sit down as 5″ heels were locked around his ankles. He stood up and fell straight back down again. The ginger vixen laughed and said that all whores are used to high heels and that he should get used to them and quick. They walked out and the van was still there and once more he was placed in the back but with no handcuffs or gag this time.

Again no-one spoke and the drive was a long one. When they got to the club he was taken out and told to stand there whilst they spoke with the bouncers. The bouncers looked at him and smirked and they were waved in.

Now Allyson, remember that is your name this weekend. All you have to do between now and midnight is talk to as many people as possible and get as many punters lined up for your four hour suck-a-thon as possible. The only thing you are not allowed to do is suck anyone off for free, leave the premises or make any contact with me.

He walked into the bar and realised he had no money. He went to the barman and said that he had no money and the barman smiled and said it wasn’t a problem ‘you are a glory hole whore…drinks are free for you lot.‘ Kevin or was it Allyson? He wasn’t sure who he was anyone but he sat in the corner and nursed a pint before a friendly man approached him.

Allyson is it? What time are you in tonight?

Erm…midnight I think,‘ Kevin muttered and he said that he would see me later and instructed me to have fun. Kevin went to the bathroom and saw the bathroom stalls and the one on the end had a sign on it ‘Sissy Whore Allyson is out. She’ll be in from midnight. £10 blowjobs and if she doesn’t swallow your full load you’ll get your blowjob free!

Kevin shuddered. This had all become too real. He panicked about diseases and didn’t know what to do. The best plan he decided was to get drunk and then at midnight he could explain to the red-headed vixen that he was scared. As the booze flowed he found himself dancing and getting a lot of attention. A lot of the men in the club came up to him having seen the notice in the toilets and seeing his name badge. Lots of ladies came up to him too and he felt he had never been so popular.

He found himself feeling like the most popular person in the club and he liked this feeling. Lots of people pinched his bum and squeezed his stuck-on tits and this just turned him on. He thought about having a wank as no chastity belt was stopping him but he decided to just enjoy the attention.

At 11:30 he felt hands on his shoulders and it was the two bouncers. They told him it was time to ‘pay the entry price‘ and escorted him to the backroom. ‘No, no, no‘ screamed Kevin but that weren’t listening. He felt so much relief when he saw the vixen who had brought him here in the backroom as well but saw her with a cock in her mouth and a sign around her neck stating ‘Paying the price for Sissy Whore Allyson’s rent.

Kevin was confused. Very confused. ‘You see your owner? She has to pay for your rent in the glory hole and she’s been in here all night sucking cock so you can sell blowjobs tonight — you must be grateful.‘ Kevin had to watch her finish sucking off her latest punter before the bouncers said that he was next up and promptly she started sucking me off. She was extremely eager and he exploded into her mouth and she gobbled it all up. The bouncers said it was time and she got up and thanked them for their hospitality.

Kevin’s head was spinning and the vixen whispered into his ear, ‘the thing is I love sucking cock too and I was extremely jealous of the night you have in store and I have to supervise you tonight so I had to get my cock sucking in early. I had the choice of paying £100 for your spot in the glory hole or suck off all the male staff. I chose the latter.’

I just wanted to ask you about condoms and diseases…’ Kevin started to say but was quickly stopped in his tracks, ‘you are a sissy whore…you don’t care about these things you just care about the money. If you get something then it’ll mean you are a proper whore and you should be proud of it.‘ Kevin’s head was spinning as she escorted him to the bathroom and opened the stall that was to become my workplace.

There was piss and poo on the floor and the whole place felt like it hadn’t been cleaned in weeks. ‘This is the glory hole stall for a reason — it is for starters like you and is as skanky as they can make it. If you stay in here without asking to leave then you’ll make it sucking cock anywhere.‘ The vixen smiled and told her sissy to go in and kneel on the floor in the pee and poo.

Kevin did as he was told before his vixen placed a collar around his neck and chained him to the wall. ‘Are you ready?‘ she asked and he nodded and she closed the door and he could hear the unmistakeable click of a padlock. There he was locked into a bathroom stall in piss and poo and before he could get his head around what was going on a cock came through the glory hole.

He caressed it with his right hand for a minute or so before he heard ‘suck it you fucking bitch‘ and I took it into my mouth. The cock’s owner decided it wasn’t as much of a blowjob as a face fucking as he roughly fucked my face and exploded but before he could swallow it dripped out all over my dress and on the floor. All Kevin heard was ‘the bitch didn’t swallow…a free blowjob…get in!‘ and Kevin sighed.

The vixen apologised to the customer and told me through the stall that she was disappointed in him. Kevin was distraught and promised himself that he would do better next time. Next time happened to be just 30 seconds or so later and this time the guy wanted a slow and sensual blowjob and he got into rhythm and swallowed. Kevin found the taste disgusting but a ten pound note came through the gap underneath the door and he put it down his bra and got back to work.

This is how the rest of the evening panned out. Some cocks pulled out on purpose to get away with not paying and some he couldn’t handle but some loads were swallowed. Kevin had no idea how many cocks he had sucked but counted his ten pound notes and there were just 17. He knew he had given at least double that many blowjobs and felt like he had let the ginger-haired vixen down.

The padlock was unlocked and the door opened. She asked for the money and she counted and seemed to be quite pleased, ‘£170…not bad for your first night. However it isn’t the £480 I want off of you so you’ll be working again tomorrow but for now lets get you back to the house.

She unlocked Kevin and told him to not utter a word as she helped him off the floor ‘you are a disgusting mess Allyson…I bet you still feel like a Kevin but you are most definitely an Allyson,’ she said as she ushered him out into the bar. No-one was there and the club was closed. The bouncers came up and said they wanted extra payment for a good nights work. The vixen quickly got on her knees but they said they wanted ‘Allyson’ to show them whether she was worth all the hassle. Kevin still was struggling to be called that but he didn’t struggle in sucking them off and swallowing. At this point the vixen came up behind me and uttered the words ‘Allyson I am arresting you for prostitution. You do not have to say anything but whatever you do say may be used against you in a court of law.‘ I was once more confused as she handcuffed me behind my back and led me outside to the van and bundled me in the back.

Taking blowjobs that were rightly mine now is it Allyson? I told you never to give away free blowjobs and you got on your knees so quick and started sucking them off before I could stop you. You are some whore and maybe the safety of a fetish club isn’t enough for a whore of your calibre.

Kevin had no idea what she meant but he would by the time he fell asleep the following night. They got back to where the vixen seemed to live and she told him that he wasn’t coming in the house looking or smelling like he did. So he had to go around the back to a small shed. The vixen opened the door and he saw a small jail cell.

Right then Allyson lets book you in,’ as she asked Kevin a series of questions as she typed in the answers into her computer. She then instructed Kevin to stand in front of the camera. She placed a sign around his neck with his real surname but luckily only his female first name, a number, the date and the words ‘Sissy Whore Jail‘ before proceeding to take his mugshot. She then took off his handcuffs and fingerprinted her prisoner before ushering him into the jail cell.

Right then Allyson…you will stay in jail overnight whilst I decide what to do with you tomorrow. You have been booked into the Sissy Whore Jail and there is no bail here. You’ll face court in the morning and your sentence will be passed. You shouldn’t have sucked off two guys for free as that is against the rules of being a sissy whore. Sweet Dreams…‘ With that she locked the door to the jail cell and the shed and left him alone. Kevin was still in a daze and wasn’t sure what was going on but one thing he did know was that he was shattered and he fell asleep within minutes. Friday night had been more than he could ever have imagined and he had no idea what was in store for him come Saturday morning…


Doing bad things sometimes feels so good…..

I had been planning for weeks in fact ever since I had started my new job to play in my office, since starting I had been fortunate enough to fuck a Trans girl over my desk in my daytime guy mode but had never had the pleasure of a guy screwing me on my desk yet.

Knowing there were several guys who were interested in helping me indulge in my fantasy play I decided to set up an evenings fun, now as a manager I got to set the rota for the week and knowing I would sign myself onto the twilight shift I could organise my evening of debauchery.

Soon enough Wednesday rolled around and I had been chatting to a very well endowed guy I had got to know on a swingers site, he had his invite and was promising to make me feel like a total slut for a few hours. Not only that but his muscular torso and 8 thick inches would make sure I felt like a total slut as well.

Getting to my office early afternoon I had so much to do and a staff meeting to run but all that was going through my head was the thought of me dressed and being fucked hard on the desk we were all to sit around during our staff meeting, I have to say even sat doing my daily paperwork I was nursing a semi hard cock in my work trousers.

Knowing my bag was in the back of my car just outside the door was enough for me to make excuses to go and find various useless items from the boot, any excuse to slip my hand inside my bag and feel the soft feminine lingerie I had ready for the evenings shift.

Sat watching the clock as I spoke to my staff about site issues and upcoming improvements I knew full well I could not wait for the evening, as soon as the meeting was over I sent both my guys home and took on their duties myself just to pass the time and sure enough by the time I had finished attending to customers and problems it was getting on for 7pm.

Sitting down to have a light dinner of tuna with pasta and dressing I felt the stirring in my groin again but I knew I could not risk dressing yet as we still had regular customers who would come to the offices up until 9pm ish, deciding to go have a walk around site and do some inspections did little for my raging sex drive and soon enough I found myself in the toilets nursing my thick 8 inches to an explosive orgasm coating the toilet seat and floor in my spunk.

Now there was one more job to do and as I had to clean one toilet cubicle I thought I may as well do the whole toilet area, not the job you really want to be doing but sure enough it helped pass the time and by the time I finished it was approaching half past 8, grabbing my bag from the boot of my car I headed back into my office and cleared my desk popping my bag down just underneath ready for me to change.

Setting up my laptop so I could get online and watch some porn to really get me going again I decided it was near enough to 9pm so I thought I wont get any customers now and began the log off procedures from all our computer systems, finishing up and about to close the front office a regular face appeared and wanted to pay her permits so logging everything back on again I quickly did her paperwork and tried not to appear flustered.

Spotting I was rushing around instead of standing around chatting the customer asked why I was in such a rush tonight as she had obviously picked up on me checking her out on other evenings when she popped in, she was right too a proper gorgeous little blonde always in heels and always smiling.

Boy if I got chance I would of loved to fuck her hard on my desk but tonight it was my turn to enjoy some cock and as I had not been fucked in near 3 months I was gagging for it, making my excuses saying I had a friend I had to go meet the customer just said well have fun and I will see you soon.

Just those few words made me all the more horny as the thought of making her cum all over my cock rushed through my mind, pulling myself back together and once again logging out I decided this time I would close all our security shutters so we appeared closed to the public. Doing this meant I could get in trouble if any senior management happened to drop in this evening but normally after 9pm I was always considering going home anyway so I knew I would have the place to myself.

The guy I was meeting was called Jason, I had looked at his profile maybe a couple of times and then one day he dropped me a message saying he like what he saw and wondered if I would meet him for some hard sex sometime.

A few day earlier I had sent him a message just saying that I had this fantasy about being fully dressed and bent over my desk and used by a hung stud like him, fortunately he took the hint and said he would love to give me his cock and ultimately his cum deep in my tranny butt along with his contact number which I quickly saved into my mobile.

And sure enough at exactly 9.15pm my phone rang and as the display lit up with a name it was Jason, answering in my very best feminine yet submissive tones I simply said

“Hi Jason, not quite ready yet babe been held up at work”

Answering “No problem give me the postcode and I will see you in say half hour?”

Agreeing and giving him the office address and postcode he chuckled and when I asked why he replied

“That’s a car park, I park there all the time…Don’t tell me you work in the site office?”

Replying that I do Jason just chuckled again then added “I bet I can guess which one you are but I am still going to fuck you senseless”.

Now feeling a little nervous about the meet I said yeah ok I guess I will see you in around half hour then, putting the phone down and heading to my office to get ready the whole time thinking if anyone else I know finds out about this my job will be over.

Fighting off the urge to cancel I quickly checked my online profile and saw I had another message, opening it and looking at the sender it was Jason and all it read was

“Don’t worry I won’t tell anyone, you can be my little secret.. See you in a bit”

I was so glad he had sent that and all of a sudden I found myself sat in my big leather chair naked bar the pair of lace top stockings I was pulling into place up my shaven legs, standing up and tucking away my rather large cock I slid my stocking coated legs into a tight pair of purple and black lace panties before slipping on a pair of 5inch black satin high heels.

Now I was starting to feel horny again and trying to keep my cock from getting hard and spoiling the illusion I was creating, pulling my steel boned corset into place and making it tight enough to feminise my waist and increase my bust. It hurt like it did the first time after it had been so long since I last tried it on, squeezing my waist from 34 inches down to 30 inches and giving me a hourglass figure with my chubby bottom that I was always told was very cute and infinitely fuckable.

Now came the hardest part as I sat and rediscovered the joys of being breathless from the extremely tight corset pinning everything in and squeezing my internal organs to the point where as I would bend I could not breathe at all, taking a moment to get used to the short breaths I had to take I slowly fixed my make up making sure every last bit was perfect from the rose red lips to the mascara and eyeliner making me look totally feminine from every angle.

Getting to my feet and picking up my wig I had chosen for tonight I wiggled my way to the staff room where I knew there was a long mirror, its always so strange seeing myself looking totally feminine without the wig but as I put it into place and let the long black hair fall past my shoulders and across my brow I knew I looked as good as any genetic girl could if not better.

Tottering back to my office I pulled out my dress for the night a tiny but very stretchy Pvc mini dress that barely covered my pantie encased cock and balls and didn’t even make my stocking tops, I knew Jason loved this dress as he had commented on my pictures in it online.

Now I was ready but suddenly I forgot I had not douched and going out into a dark car park and across to the toilet block to douche with freezing cold water was not going to be fun especially in this dress, checking the cctv system I decided it was clear and as I wanted to move quick I decided to take off my stilettos and put my shoes back on which must have looked bizarre.

Unlocking the toilet door and darting inside I quickly filled the sink and filled my douche with the water, getting into one of the cubicles I inserted its neck deep into my anus and as I began to spray the water inside me it hurt like hell, the water was so cold it didn’t help me relax my anus at all so as I sat down and had to expel it all the rush of cold water and shit was foul and painful all in one go, there was no way I was going to do a second one as I usually would.

As I locked up the toilets again and headed back across the yard to the office I saw a figure stood outside and the rush of fear took control, I knew I had been seen and as yet I was unsure who it was. Feeling my heart beating so hard I could hear it in my head I took my time and was trying to work out who it was.

It was not until I got close and the voice said

“You know those shoes look shit with that outfit Lisa”

The feeling of relief washed over me as I knew it was Jason, he said he had been trying to call me and as I explained that I forgot to douche he just chuckled as I unlocked the door and led him into my makeshift boudoir.

Trying to still relax I went round closing doors in the office block so he only had one choice and that was my office, as soon as we were inside my office I turned to face him and he locked his large muscular hands around my corseted waist and just said very hot babe.

Leaning in to kiss him he said not yet bitch, and with that he reached down and released his belt and his flies letting his jeans drop to the floor to reveal he had no boxer shorts on, reaching to wrap my hand around his already semi hard shaft Jason said I would prefer you suck it.

Not having to be asked twice I got to my knees on the horrible cheap office carpet and slowly wrapped my rose red lips around his impressive thick bell end lapping at his piss slit before taking his shaft deep into my mouth, slowly encouraging his rapidly stiffening cock to get to its full erection, taking the back of my head Jason started to pump his cock in and out of my mouth making me gag as his bell end hit the back of my throat almost making me vomit.

Choking and still trying to impress him I looked up to see his deep brown eyes watching me envelop his thick cock between my made up lips, letting me go I stood again and took his now near 9 inch cock in my hand and began to slowly wank him off as our lips met for the first time that night.

Fortunately I had chosen well as I discovered Jason had a pierced tongue and a lot of tattoos which is a major turn on for me, I just adore tattooed guys.

Also I am quite tall at near 6 feet 3 when dressed and in 5 inch heels I make most guys look short but this time Jason almost matched my own height so it was easy for us to maintain full body contact, as our tongues began to meet I was in ecstasy and then without any warning Jason pulled my panties aside releasing my own 8 inch stiff prick and went to his knees and began sucking me off.

Trying to move closer to the table so I could rest against it Jason knew what he was doing as he took all of my 8 inches deep into his throat making me squirm with pleasure, making my way onto the table Jason got my message loud and clear as he released my cock from his talented mouth and pulled my panties off over my 5 inch heels throwing them to the floor.

Eager for his cock I laid back teasing my nipples begging him to fuck me, but as he stood still rock hard he bent over kissed me hard on the lips and then disappeared between my thighs working his pierced tongue around my tight balls and down my perineum to my puckered little Tgirl pussy hole.

Feeling his tongue investigating my arse pussy I spread my legs a little and Jason held my legs back slightly as he buried his tongue deep into my butt, his piercing running around my anus was driving me wild and as I laid back enjoying the licking I was getting Jason suddenly pushed a thick finger into my butt stretching my anus open and then another making me moan as he continued to lick me out savouring my juicy little arse pussy.

I knew I had to have him inside me as soon I was going to cum if he kept lapping at my butt, begging him to push his cock up me Jason didn’t take much convincing. Standing at the edge of my desk he slid me onto the side and put my heels up to his shoulders and offered me his thick veiny 9 inches, I had never had one so big before so was sure it would hurt but Jason had me so relaxed and turned on that he eased his bell end in and with a audible pop he was in me.

Filling stretched and full of cock I moaned with pleasure begging him to give me as much as I could take and with that he slid into me inch by inch, biggest I had ever had was about 7 inches in me so Jason’s was to be a challenge especially as he was so thick as well.

Easing into me he made it in about three quarters of the way then began to slide slowly in and out of my tight hole making me purr with pleasure each time I felt him slide inside me again, soon enough he had me totally relaxed and enjoying his fat prick inside me and sure enough once he had me wet and juicy he went for it and managed to slide into me right up to his balls.

Good it felt so good having a thick 9 inch cock in my arse being used like a gorgeous all be it slutty girl, now I was comfy on his prick I asked him to fuck me hard as he had promised and I didn’t have to ask twice as Jason built up the speed and soon enough his full balls were slapping my arsehole as he drove his manhood into my tight anus.

I had never felt so good and wondered why I hadn’t taken Jason up on his earlier offers to fuck me, now I was wet and so relaxed Jason was slamming into my butt pushing me across the desk as he did. Moaning hard I begged him to give me his cum and he replied not yet.

Pulling his massive cock out of me I suddenly felt empty but as he pulled me to my feet I attempted to catch my balance in my heels and found my legs were numb from the deep pounding he had given me, fortunately I didn’t have to stand for long as Jason ordered me to turn around and bend over the desk.

Getting a good fix on the desk I wasn’t sure what was to come next, suddenly I felt Jason’s pierced tongue licking out my well fucked butt I almost shot my thick creamy load there and then but as he reached round and grabbed my girly cock I knew it was time and I needed to cum bad. Begging him to let me cum he once again said no not yet hun and put an elastic band from my desk tightly around my erect prick preventing me from cumming.

Standing behind me I felt his thick cock run down the cleft of my arse and with a push against my anus Jason had all of his thick 9 incher deep in my butt again, this time he took me nice and slow reaching round squeezing my nipples and kissing at my neck as he ground he thick cock in and out of my well fucked arse.

Begging him to fuck me and fill me with his spunk he pushed me face down onto the desk and began to fuck me hard deep and fast slamming his thick cock as deep as I could take it almost pushing me off my feet with each time his full balls smashed against my arse, screaming and writhing in not pain but pleasure I began to buck into him so he could get as deep as he liked and with that Jason grunted hard and I felt the rush of his cum filling my insides.

Pumping 2 or 3 loads up me I felt such a slut and loved the warm spunk running all round my anus and washing past Jason’s cock as he still continued to fuck me, egging him on I begged him for another load up me and sure enough this time it didn’t take long, a few hard pushes into my seriously cum soaked anus Jason spat the last of his load up me.

Sliding from my sopping wet cunt Jason fell back into my big leather chair panting like a exhausted dog, sliding my fingers into my cum soaked bum I got a good soaking all over my fingers and hand and proceeded to lick my fingers clean of his spunk, it tasted so good with the mix of cum and lube and my own sweat.

Savouring the taste I looked over at Jason and sure enough he had been enjoying watching me eat his cum so much he was sat nursing a hard cock again, asking him if he wanted to ride me again he asked if I would suck him off.

How could I resist after the fuck he had given me….

Getting to my hands I knees I crawled across the room until I knelt in front of him slowly wanking him off as the cum that had been in my butt was slowly making a puddle on my office carpet, sliding my still rose red lips around his bell end and lapping the remaining cum and anal juices from his prick tasted amazing.

Slowly taking his impressive shaft into my mouth he started encouraging me to make him cum again

“Come on you little gorgeous slut make my prick fill your sexy mouth with spunk”

I could not resist that invite and sure enough I began to use every technique I know and as I groped his balls as I sucked him deep, it was seeming to take forever but after Jason had already cum 3 or 4 times in my butt I should of expected it would take a while.

Getting bored of sucking him I decided what I would do and as I pushed a finger into his anus I took at least three quarters of his shaft into my mouth and as I flicked at his G spot his bell end exploded not once but two or three healthy spurts of thick man cum filling my mouth as I attempted to swallow as much as I could.

Asking him when I could cum he said maybe I will let you now and with that he released the elastic band from my still rock hard 8 inches and pushed two fat fingers up my butt as he sucked me deep laid back on the office floor, the orgasm hit me like a train and as it washed over me my whole body contorted firing several thick spurts of cum direct into Jason’s mouth.

Swallowing most of it he said I know you love the taste and laid on top of me as our lips met, sharing each others spunk as we both laid exhausted and emptied.

As we went to clean ourselves up Jason said to me any time you need a fuck baby please call me and with that he pulled his Jeans and shirt back on and left, sat on the edge of my desk and looking around my office there was cum all over my carpet and the smell of sex filled the room so much I was sure I would be fired the next morning but as my big boss walked in he commented you must have had one hot slut in here last night.

Little does he know that hot slut is me, a sexy hot dirty tranny slut with a penchant for hot guys and gallons of spunk in my tight butt…..x

“Don’t worry Jo,” Alex reassured me with a gentle smile. “We’ll take it real slow. But you may want to start lubing up and doing your ‘stretching’ exercises.”

“Yeah Jo, and we’d be happy to help you out,” Maria chimed in. Quickly she came over and took one hand while Chantelle took the other. “Charlene, be a dear and grab some lube from over there near the wall.” While Charlene went to follow Maria’s instructions, she looked at me with a worried look on her face. I returned the look with a subtle nod indicating that everything would be okay.

The girls led me over to the chest and got me settled over it like I was laying across someone’s lap. Chantelle slid my skirt down my legs, caressing them lovingly all the way down. “You know you have beautiful legs. I could almost eat them up.” Then she gave a quick kiss on each cheek before Charlene handed her the lube. Maria knelt down in front of me and gave me a deep tongue kiss, distracting me from the cold lube being spread on my ass.

“Mmm,” Maria intoned through our kiss. “You taste like strawberries.” I smiled at that and returned her kiss with a playful nip. “Now are you feeling okay back there?”

“Yes, Chantelle has very soft hands,” I replied.

“Okay, then she’s going to start stretching you out,” Maria started to describe what Chantelle was going to do and, out of the corner of my eye, I could see Charlene looking on with a mix of awe, nervousness, and a little bit of fear. “Jo, what Chantelle is going to do is use her hand, okay? Just nod.” I nodded. “She’ll start one finger at a time, until she can get her hand in there…then her fist, and by then, you should be plenty stretched for Alex and Mark, okay?” I nodded. “I’m going to stay right here next to you and if it gets to be too much or if she starts moving too fast, I just want you to squeeze my hand, okay?” I nodded.

I closed my eyes and started to lose myself in the sensations of Chantelle’s hands on my butt. She wasn’t rough in her technique…not that I’d expected her to be. But it’s just, she was straightforward about getting her hand in either. She took her time with one finger, sliding it in and out, slowly, gently, and from different angles…tickling my prostate…curling the finger and pulling it out…every move measured against the reactions she drew from me. The thing was, she didn’t just focus on her hands connection to my rear. With her other hand she caressed each cheek, sometimes running her hand all the way down my thighs to tickle the backs of my knees. It was such an odd sensation when she would do that with her fingers still inside me because I got confused about where I wanted to move to or how I wanted to move. When she added her second and third fingers, I couldn’t help but moan. Unconsciously, I started to rock against her hand, but I gasped in surprise when I felt her bite my cheeks. I didn’t think she drew blood, but the sensation set off sparks in my head. The spankings that she mixed in left me reeling and dizzy…not because they were hard enough to really hurt, but simply because the sensations came out of nowhere. I think I gazed out of half-closed eyes momentarily to see Maria smiling at me and licking her lips. I could still feel her hand in mine, but when I searched for her other hand with my eyes, I found it hidden in her own panties and I could see she was enjoying herself almost as much as I was. She gave a gentle squeeze when she saw me looking and I smiled at her.

Apparently Chantelle saw our brief interaction and decided that I needed a little more…distraction, so she abruptly inserted her fourth finger into my rear eliciting an audible cry. Still, she didn’t rush it after that. She gave me a few moments to adjust and wiggled her fingers just to hear my breathing get ragged. Slowly and methodically, she continued to slide her hand in and out, filling me…stretching me…making me feel sensations that I couldn’t describe, only experience. As I got acclimated to her hand, I couldn’t help but rock back and forth with her rhythm. But just when I thought that I had reached the pinnacle…that I could start to really relax and let myself go, Maria whispered to me “one more finger to go, then the hand…then she MIGHT let you come.” I nodded as best I could and let myself slide back into that mental and physical cloud that was supposed to be carrying me to ecstasy.

“Here we go,” Chantelle said. And with that, I felt her pull out slightly and change her hand position so that all five fingers were teasing my sphincter. Her hand slid in until there was resistance…a silent “O” on my face the entire time…then as I relaxed, further and further in… Maria reminded me to breathe because I’d apparently forgotten to do so while focused on Chantelle’s hand. Seconds seem to stretch into minutes and my ass felt fuller than anything I’d experienced thus far. Finally, the pressure eased and I could tell that Chantelle’s hand was fully inside me. I could feel her moving her fingers around, and when she actually made a fist, I damn near cried. It seemed like every sensation I had was centered there. I didn’t even feel the trunk under me. I was only vaguely aware of being pulled back from the trunk, guided by Chantelle’s hand.

“Open your eyes Jo,” Chantelle told me. Slowly I opened them and as I did, I saw Maria positioning herself below me. She had stripped off her clothes (although I had no idea when she’d had time to do that) and had slid under me. Chantelle raised her hand and cantilevered me down to kiss Maria’s welcoming mouth. As we kissed, I felt more movement near my groin. But it wasn’t Chantelle’s hand in my ass that I felt. It was her other hand stroking my penis… I’d been so focused on what she was doing to my rear that I’d forgotten I even had one. Slowly she stroked me, letting the silky softness and gentle touch of her hand massage me to a hard state. Maria and I continued to kiss and I started to lose myself again in a world of warm sensations that I had tasted over recent days, but had never really experienced before.

Chantelle used her hand again to guide me lower, forcing my legs straighter until I started to feel a different warmth on the tip of my penis. It was then that I knew that she had positioned me right at the entrance of Maria’s vagina. I could feel Maria start to shiver beneath me as my penis twitched against her labia and involuntarily jerked up towards her clit. As we continued to kiss, I could hear Maria moan lightly.

As if that were a cue, Chantelle pushed her arm further into my ass, forcing me down and in to Maria’s waiting embrace. An indescribable sound escaped my lips as I entered Maria. It had been so long since I’d been with a woman (instead of “being” the woman) that I’d almost forgotten what it felt like. But Maria’s warmth…the way she fit me like a glove and used her muscles to clamp onto my penis…it was like riding a bike and I remembered the beauty of sexing a woman.

I was still at Chantelle’s mercy though. With her hand in my rear, she dictated the speed and pace of my thrusts into Maria. It’s like she was using me as a dildo to fuck her girlfriend. Not that I minded. Each push and pull and squeeze and release elicited sounds from Maria and from me…sounds without words, but speaking of passion and excitement and feelings of pleasure.

I thought that I heard the guys whispering something in the background but I had no clue. The focus of my world was being used by Chantelle and Maria…no, not used…accepted or included in the lovemaking experience maybe. I didn’t know. I could barely think. All I knew was that I was enjoying one of the most fulfilling (and filling) sexual experiences that I’d ever had.

Chantelle changed her hand’s position in my rear to put pressure on my prostate and I knew that I would not be long in cumming. Oh, the feeling of cumming inside a woman was something that had been too long in coming. From Maria’s vibrations and moaning, I could tell that she was already well on her way over the brink of ecstasy. A few more seconds of Chantelle’s pumping me into Maria and I was sent over the cliff as well…crying out…tensing up…shuddering uncontrollably…and tightening my ass around Chantelle’s wrist. Until finally, I was done. Of course, Maria continued vibrating for a few moments, clutching onto my penis with her muscles like her life depended on it. Every little movement of Chantelle’s hand in me caused me to move in Maria and set off a new round of fireworks for her (I think I actually saw sparks of color in her eyes when they rolled back in her head).

As I lay there on top of Maria trying to catch enough breath for both of us, wrapped in Maria’s arms, I felt pressure behind me. “Hold still,” Chantelle said as she straightened out her hand and slowly removed it from my rear. “Did you enjoy that?”

I nodded. I tried to speak but apparently my voice wasn’t ready to work yet.

“Good, good,” Chantelle said as she caressed each butt cheek. “Well, don’t get too comfortable yet. I think the guys are ready for their turn.”

My eyes snapped open at that. In all the pleasure for being with Chantelle and Maria, I’d managed to forget the original plan. “Do we have to do it now? Can’t I just lay here with Maria for awhile?”

“No baby,” Chantelle responded. “You probably ought to ‘get your ride on’ now while you’re still stretched out and can accommodate them both.”

Some of the nervousness returned, but it was overwhelmed by the warm afterglow I was feeling and the soft touch of Maria’s hands on my back made me feel safe enough to go for it.

“Okay, okay,” I mumbled from my after-sex haze. “Let’s do this.”

“Alright, gentleman?” Chantelle turned to Alex and Mark who had already taken off their shirts and looked like they were ready for action…if I was judging the bulges in their pants correctly from my vantage point.

“Here Jo,” Alex offered. “Let me help you up…and over to the bed.” Alex grabbed me by the waist and quickly got me into an upright position. I tried to stand up but found myself leaning on him because I couldn’t trust my unsteady legs. He led me over to the bed where Mark had been getting situated. Mark was sitting on the edge of the bed when Alex surrendered me to him. He took me into his arms and gave me a slow, languid kiss. As he pulled me closer, he laid back on the bed, pulling me on top of him. As he continued to kiss me, I couldn’t help but rub myself on top of him, letting my hands sneak up and play in his hair, while his hands caressed my legs and pulled them up until they were bent, one on each side. I felt him raise me up a little bit in order to slide his pants down to expose his erection. He settled me back down and I was able to feel his cock sliding through the crack of my rear. He stopped kissing me for a second. “Are you ready?”

“I am,” and with no further words, he slid his penis into my stretched out rear-end. I was still able to feel him even though I’d been stretched farther than I ever though possible by Chantelle’s hand. I placed my hands on his shoulders and levered myself up to a “riding” position. Mark put his hands on my hips as I got him settled comfortably in my rear. After a few up and down movements (and more than a few moans of pleasure from both of us), I indicated that I was ready to go for two.

“Well it’s about time,” Alex said. “Ya’ll were acting like you didn’t want to share.” He crawled up on the bed behind me and gently pushed me back down on top of Mark. Mark was kind enough to grab both cheeks and part them so Alex could see what room he had to work with. The feel of his hands spreading me wide was…yummy. Still, I knew what was coming. I felt another pair of hands on my hips and knew that Alex was about to make his presence felt in a space that might or might not be able to accommodate him.

“Here we go,” Alex said. And with that, I felt Alex’s cock fighting to slide past Mark’s. “I’m going to add a little more lube…just to make things easier.” The coolness was welcome as I enjoyed the heat and friction from Mark’s penis and tried to relax enough to let Alex join in. Slowly and steadily, Alex pushed his penis past my opening.

“Ohh…” I didn’t have any words as I experienced double penetration for the first time. The feeling was unlike Chantelle’s hand because it wasn’t just the width that I was dealing with, it was the contradictory movements as the guy’s cocks slid past each other and moved around in an effort to get settled. If Alex moved, I felt sensations on one side, but if Mark moved, then I felt sensations on the other. And if they moved together…I experienced sensory overload. I think my eyes might have been open, but I wasn’t sure. If they were, then I’m pretty sure they were rolled back in my head like Maria’s had been. I won’t say that it didn’t hurt, at least a little bit. But if this was pain, then I was ready to be a masochist. Alex and Mark continued to jockey for position for a little while, eliciting grunts and moans and squeals (those were mainly from me) from all parties involved. Finally, after a few minutes of pleasure, they settled down so we could proceed with the next step of the plan.

“Charlene, why don’t you take your place up front?” Maria suggested. I tried to refocus my eyes as I watched Charlene make her way over to the head of our bed. “Alright Jo, time for you to complete the foursome.” Maria seemed to enjoy her newfound role as director. “Charlene, lift up your dress so we can see Jo sucking your cock.” Charlene didn’t hesitate to comply with Maria’s suggestions and I didn’t want to disappoint any of them, so I opened my mouth to enjoy my second taste of Charlene.

Charlene stepped forward and slid her cock into my mouth while I moaned around the sensation. As soon as she got situated, the boys went to work. Alex and Mark started to pump in and out in and alternating fashion…never leaving me empty and leaving me confused about whether I was coming or going. Thankfully, with both of them holding my hips and waist, I didn’t have to worry about which way I should be sliding. I was able to lose myself in the pleasure that they were generating inside my rear. I could tell that Charlene was enjoying watching me get fucked by the guys because she kept whispering “ohmigosh…Jo…that is so freaking sexy…” I responded by sucking with a little more insistency, occasionally switching up my technique and curling my tongue along the underside of her shaft as I tried to coax the cum out of her.

“Jeez that’s a helluva shot,” Maria whispered. “Did you get it Chantelle?”

“Mmm-hmm,” Chantelle murmured as she licked her lips with anticipation. “I’m just waiting for the money shot now.”

“Did you hear that Alex?” Mark asked. “The girls are ready to see it all.” (funny…his breathing was just a tad ragged) “Shall we give it to them?”

“Heh,” Alex chuckled, “I’m ready whenever you are. Charlene, are you ready?”

“Oh God yes,” Charlene stammered. “Jo is GREAT at sucking cock.”

“Will you look at that grin?” Chantelle asked. “I’d almost say that you like her better than me.”

“No baby, that’s not it,” Charlene backpedaled. “You know I love how you do me, but I’d be lying if I didn’t say that I really like Jo’s technique.”

“Fine, fine,” Chantelle said with a smirk. “Are you ready? I think the guys are waiting on you.”

“Yeah, if Jo keeps doing what she’s doing, I’ll be there in a minute,” Charlene replied. Since that was all the encouragement I needed, I started going after Charlene’s cum like it was the fountain of youth. I sucked with a little more force, tickling the underside of her shaft, moaning on her head, and trying every technique that I could imagine to send her over the edge. As my moans and my efforts got more enthusiastic, Alex and Mark started really taking advantage of their position. I could hear their grunts as they starting pumping in and out of my ass more aggressively, intermittently eliciting a squeal or delight from me as they hit spots I didn’t even know could bring me pleasure. Seconds and minutes seemed to stretch into hours as I got lost on wave after wave of ecstasy…until…I felt Mark starting to tense up…then the first jet of cum filled my rear as Mark let out a grunt signaling the beginning of his release. As Mark continued to spurt cum into my rear, the activity spurred Alex’s own climax and soon, both of them were shooting ropes of cum into my ass which was already filled to capacity. And to make sure that she wasn’t left out, Charlene started to blow her load deep into my mouth and throat, quickly overwhelming my swallowing capacity. It didn’t take long for the cum to start leaking out of my mouth and Chantelle made sure she got some shots of that. Then she quickly made her way around to get a close-up shot of Alex and Mark’s cocks stuck in my ass with cum leaking from around them.

“Jo, I think you’ve got this little contest won. These shots are fantastic,” Chantelle exclaimed.

I started to answer, but all that came out was “mmmpph…mmmm…” What I had been trying to say was “I can’t wait to see them.” But I knew I would have to try again after Charlene removed her penis from my mouth and I finished swallowing her gift to me.

The collective hard breathing from Mark and Alex started to slow down as they recovered from their orgasms, and Charlene reached down to stroke my face as she looked at the world through half-closed eyes and twitching in her own post-orgasmic glow. “God Jo…that was a great blow job.”

Maria came up behind Charlene and started caressing her arms and chest. “Did you enjoy that hon?” Charlene nodded and I gave one final lick to her ‘clit’ as Maria pulled her from my space. I looked up into her face and saw her succumbing to Maria’s ministrations.

“Were you enjoying yourself Jo,” Chantelle asked. She’d come along side me and started to stroke my face even as Mark and Alex continued to lie there keeping me trapped in their sandwich.

“Honestly…I did. I wasn’t sure that I’d be able to do it…but it was…intense,” I replied through my own warmth and glow. “I think I…oooohhh.” My thoughts were interrupted as Alex, than Mark, extricated himself from my derriere. Their abrupt exit left me feeling empty, and more than a little weak. Chantelle continued to caress my face as the guys moved me over onto the bed and started to clean themselves up.

“Jo,” Chantelle started, “I do want to say thank you for helping us all out. I think that whatever Maria and Charlene and I get into is going to be interesting and you are MORE than welcome to join us whenever we’re in the same area.”

“Hmm…,” I hummed out through the contented smile on my face. “Thanks girl. I know ya’ll are going to have lots of fun together. We’ve got to keep in touch.”

“Oh definitely,” Chantelle said as she leaned down to give me a deep kiss…and lick off some of Charlene’s cum that had dribbled down my chin. “You’re amazing girl…and next time, I get to ride.” She winked, gave a last caress to my face, then moved over to Charlene and Maria who were doing some caressing of their own.

Mark and Alex came back to help me up, bringing warm washcloths to help me clean my face and dab at some of the gifts they’d left behind in my behind.

“Oh…ok, as fun as that turned out to be,” I squeaked out as I winced in discomfort, “I’m gonna be sore tomorrow.” Alex chuckled as he ran a washcloth over and between my legs.

“We’re gonna get you some fresh panties and clothes to wear before we take you back to Frank and Tom,” Mark said. “And a pad,” Alex chortled. I wanted to be mad at him, but I couldn’t help but smile since I knew he was right. I was going to have to do something about the leaking I was doing, but I didn’t feel like inserting anything else back there for awhile.

“Alright guys,” Maria called out. “It’s time for us to head home. You’ve had your fun…hell, we’ve all had a great time…but it’s time for us to get to bed.” She walked over and gave me a kiss that rivaled Chantelle’s. “Thanks chica…you’re magnificent. Don’t be a stranger, okay?” Then she moved out the way so that Charlene could say her goodbyes.

June 2018
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