Hi, Lisa again. I haven’t written anything in some time. Not that I haven’t had much happening. I just had to work through some events in order to know how they would turn out before I write about them.
As I stated in my last story the men I play with had offered to pay for a transformation procedure and drug expense to become a “woman”. In my occupation I was capable of handling the expense but the offer from the men I knew was more of a request to make the transformation.
I had looked into the procedure but was unsure. There were stated possible side effects from the hormones and I personally I enjoyed sex, a lot and I did not want to have my desires inhibited. I spent a great deal of time talking with girls already on the program and I finally decided to go for it.
About three years ago I went to a Dr. and began building a relationship. It required some psychological testing and some health screening. Soon after I started the hormones which are a combination that produce the female attributes and suppress the effects of testosterone, the male hormone. I am quite slim and have an athletic build to start with but I noticed quickly that the little mid section fat I carried was dissipating and that after about three months it was settling in my chest and on my rump. Incredible to see it happen. I noticed when I laid on my side and looked in a mirror at my back side my “curves” were really developing. The guys did take notice as well and some of our encounters were exceptionally vigorous.
One of the men, Mike, from my weekend retreat at the sex camp had been persistent about contact. I have relented and he has become a part of out group. It has put more demands on my time but he has shared the expense of my transformation. Everett, who has become quite close and very much a confident said that he has gotten many requests for a return trip to the cabin but wanted to wait till I was further along with the transformation process.
My trips to the Dr. were an event in themselves. The assistants at the Dr’s office were all encouraging and helpful as well as curious. They knew from my questionnaire I had had more than a few lovers and some of the women were amazed to find how much I genuinely loved having a cock take me anally. I needed to basically live full time as a woman. As my new hormones did their job I felt more and more feminine. My first trip to the Dr I wore sweats. By twelve months I went dressed up. I preferred nice conservative dresses, very feminine. Stockings, makeup, nice hair, confident, heels clicking as I walked. I love having my skirt or dress swishing around me as I walk. I’ve also found I really like the wrap around dresses. I can tie them at the waist and button a few button’s and let the front act like a long slit when I walk yet it covers plenty when standing and when sitting I can cover or let the dress fall to the sides exposing my legs completely if I’m so inclined. I’m not afraid of drawing eyes to me as I know I am quite passable now.
The first procedures I had done were my face and neck. Mainly the nose. I wasn’t bad with makeup, in fact with effort I could be hot but now I’m pretty good without makeup and very passable without any makeup what so ever.
Once my face was done I had my name changed so my documents could then be changed. I found these procedures to be much simpler than I imagined them to be.
Then last year I had a decision to make. Time for the breast implants. Of course the men all wanted monsters on the scary side. I on the other hand did want some size as I enjoyed approving stares but I didn’t want to be a freak show turned into a carnival ride though. I am 5’11″ and can carry some size, I decided on a D-cup or about 400 cc of fluid per breast to augment a little over 200 cc of natural breast tissue I had. I had to have tissue expander’s inserted surgically to expand the amount of tissue to work with. This required an expansion to 600 cc per breast, 50 cc each week in each breast. This extra expansion is done to provide for a more natural breasts after the implant is placed and sewn in and a certain amount of scar tissue forms. I decided to go with the newer implants filled with tiny silicone pellets and thick viscous oil as I wanted a more natural breast without the rippling that occurs with the saline implants. These do however require a larger scar under the breast as they have to be inserted filled as they can’t be filled once installed like the saline implants. You also want a surgeon that sits you up during surgury to check size and placement.
The day arrived and ended happily in a Demerol induced sleep. I will say this was not for the weak spirited and my hat is off to all the women that endure this procedure. It took about ten days to be comfortable with pain free movement but I will say I was visually inspired with my new enhancements. They looked HOT and the guys all agreed as well, evidenced by there teepee like jeans upon inspections. During surgury it was decided that 500 cc looked better on me so I came out of the hospitol a bit larger but happy non the less.
A word of caution though. My hormones were adjusted after this and my breasts grew another 150 cc of natural tissue per breast over the next six months giving me a total of about 875cc per breast which is quite a bit more than I was wishing for.
I decided to spend about a year now adjusting to living full time now before proceeding with the gender reassignment which I will have done in Thailand. I’ve been going to voice classes for two years to get my vocals up and I can now easily pass on the phone even. My confidence in public grows daily and it has been over a year since anyone was able to tell, even in everyday conversation. I love to wear skirts or dresses with a slit in the front. I have found they will get me out of every triffic ticket and a few date proposals
As for sex I still enjoy it greatly. My biggest worry was that I wouldn’t crave sex the way I had but I guess it fills a need somewhere deep in me and I still think of it when its been awhile. I will say my plumbing is different though. If you’re in love with your manhood this is NOT for you. The testicles will shrink some. I don’t generally get into describing my penis size but it becomes relevant to something that we discovered that I will describe in the latter part of a gang bang that my lovers had for me later in this story. My penis, never large to start with, about 5″ long and maybe a bit over an inch in diameter before when erect is now about 4″ long and the shaft is about three quarters of an inch in diameter while the head has remained about the same size when erect but erections are difficult to achieve now. I still get excited but the reaction of my body is different now. I still have orgasms but they come from inside now and I emit very little fluid. When not erect my penis is about 2″ long and about as big as a small finger.
The guys still enjoy playing (go figure) so we do so often. Sometimes singly, as a small group or recently all four guys and myself which was quite fun. This was the first time we had all played as a group since I had gotten my breasts. I wore a white boned corset that laced up the back. It had a rigid shelf cutout that supported and projected my breasts outward for maximum prominence. It tapered up to my neck to a collar around my neck, leaving my shoulders and arms bare. Three garter straps on each side held up some copper colored french heel seamed stockings with a dark seam and welt. I wore some 5″ dark brown open toed stilettos with ankle straps.
My home is a renovated barn, nice with all the modern conveniences but with lots of wood and a heavy beam construction. The guys took one the downstairs rooms which I had used as a small library and from the overhead beams installs some hooks and they made a sling with all kinds off loops and attachments. They lay me in this sling and can attach loops and bindings in many ways, thus holding my body in place in whatever position they’ve chosen for me. On this occasion they had me simply on my back with my legs up and splayed wide. A ceiling mounted camera focused on my bottom hanging over the edge of the sling and showed the picture on a wall mounted flat screen TV. My legs forced up and out allowed my anal rings to open slightly in anticipation. The tip of a bottle of lube was inserted in my bottom and at least half the bottle was squeezed into me.
Mike was the first to enter me. He has joined us from my experience at the cabin and I have played with him one on one now a few times since. He is not a tall man but very athletic, very sinewy, he is very impulsive, and authoritative. He fucks me vigorously with one goal. ORGASM! His cock is nice, about seven inches but not very thick. This guy though can squirt some semen. Enough to put out fires. Not sure where he stores it all but I can drown in it if I’m not ready to swallow and he shoots it deep in me and definitely fills me up. He can and usually does cum twice with each encounter. Not much talking, only action. Afterward, a kiss and good bye as I lay in a puddle of cream.
Anyway, as he rabbit fucked my hole I expected him to thrust and fill me but after awhile someone yelled “time” and he pulled out and Ted entered me with his mushroom shaped cock with that puffed up head. He slid in and out with the camera focusing on closeups of my distended ring as his swollen lime sized head tried to partially pullout only to ram back in. Again “time ” was called and this time Rex laid his ebony, steely hard pipe in me and again about two minutes in after time being called Everett moved up and put his monster at my opening. He slowing pushed, my body, sling and all. Being pushed up and away, gravity finally overwhelmed the tightness of my bottom and allowed Everett’s tree trunk like cock to pop through my rings. Gasping from the sudden stretch, I felt Everett continue pushing, oh so slowly, but forging deeper, his shaft thickening with each passing inch. I had had Everett in me at least a hundred times and each time he entered me I felt like a virgin being opened for the first time. The depth and the stretch were always envelope pushing when this man probed my depth. As he hit the curve he had to move and adjust, snaking his way up my gut. Once he bottomed he rocked back and forth. The head of his cock plainly visible under my corset on my left side. Mike audibly gasped how incredible that was.
At the two minute mark the process began again with Mike taking his place this time spending one and a half minutes pleasuring himself in my bottom. The men each took their allotted turns, not cumming but building up. They didn’t touch my breasts, allowing them to flop and flail, oscillate and bounce depending on the thrusts from my partner.
By the seventh go round the guys were only spending 30 seconds fucking me. Their cocks were as hard as I’d ever seen them, all pointing skyward and I could tell by the building level of excitement that large reservoirs of thick creamy semen overflowing with free swimming sperm would soon be unleashed and I was at some point very soon going to be the recipient of these pending explosions. Ted was the first to let go lunging hard and yelling. I could feel his cock throb. I’ve always loved, and today was no exception the feel of a cock pulsing in me, and today the pressure being released was exceptional. Rex entered me after Ted and fucked me for his allotted time. I always love seeing his glistening black cock turn frothy white as he fucks me when I’m full of semen. Today I was not disappointed as his cock dragged in and out, white globs of Ted cream. Evidence of sloppy seconds.
Rex was able to last to the next round and when his time was up Everett followed him in me. He took his time reaching bottom but once there I knew he wouldn’t make it to the next round. The guys had left my breasts alone but at this point Everett squeezed my breasts and pinched my nipples. He pushed me and the sling about a foot with his penis, making a pyramid like structure in my stomach as it pointed skyward, erupting hard. Everett shuddered and trembled. I knew at that instant the river of semen that tends to flow from this man was painting my insides. As Everett withdrew, Mike entered me . Mike being much smaller and me being as cream filled as I was now, I barely felt him slide in me. All the visual stimulation had super stimulated Mike to the point that on the third thrust he shot off like a rocket A ring of white semen formed around his cock as he remained rooted in me. Mike bent down and sucked my breasts.
The guys had not spent much time playing with my breasts. I realized they were trying to last longer and didn’t want the stimulation but when they were ready to cum they pinched, squeezed, sucked and slapped my boobs silly.
Rex still had yet to release his load and as he slid his black piston in me for what was now sloppy fourths, he looked into my eyes. We had been with each other enough and I could read the lust in his eyes. He was soooo ready to cum He was ejaculating before he even bottomed in me. His full pulses of cream breeding me again as my breasts were mauled in his palms. This was so HOT!
All four had tag team drilled me and now filled me. Rex and Everett took my feet out of the loops which had held my legs wide and helped me down. They had me bend at my knees and squat. Perched on my high heels with my gaping hole hovering inches over a mirror on the floor, ropes of gooey semen oozed and fell to the mirror. Strings of sticky cum spanned the distance and then a large glob appeared, then plopped out and fell to the mirror to a large “ooh” from my admirers.
Standing, the guys clapped as Mike handed me a glass of wine. The first toast was to my new breasts which all agreed were a raging success. I slipped on a white mid thigh opaque robe and we went and sat on the sofas, relaxed and recuperated.
This was only the beginning of this evening and it does get much much more interesting. Something was yet to occur that certainly had never happened to me before, that’s for sure. If you enjoyed this story and want to hear more and certainly the rest of this evening, write some feedback and let me know so I’m not wasting my time. Thank you so much to the few that have written.
So…my life has pretty much come down to this. I came home from work to see that my wife had bought a new skirt. She had tried it on and was modeling it for herself in the mirror. She looked great. The skirt nicely accentuated her sexy curves. And judging by her reaction to her image in the mirror she really liked it. But the first thought that popped into my head was, ‘that’s a really cute skirt, I can’t wait until she goes to work so I can try it on.’
I’ve been a closet cross-dresser since puberty first changed my life. In fact I was probably more like 10 years old when I first tried on a pair of my sister’s panties. I remember it was after school one afternoon. My sister was at a friend’s and my mom was just getting started on dinner. I happened to notice the panties on top of the hamper in the laundry room.
They weren’t all that sexy. They were just girl’s briefs, white with blue trim at the waist and legs. But the silky-smooth material was irresistible. I had seen them before, and others like them. But something in that moment made me stop and wonder what they would feel like. So I grabbed them, stepped into my room, and closed the door. I don’t remember many of the details other than once I had put them on I was hooked. They were so much softer and smoother than my briefs.
After that moment I would sneak my sister’s panties, and sometimes my mother’s panties, from the laundry whenever I thought I had enough time to enjoy them. Not every pair I saw, though. I was selective. I wasn’t into sniffing them, or turned on by the fact that they had been worn and had been rubbing all day long against a pussy. I couldn’t explain it at the time, but I can say now it was just the sheer femininity of them.
It was shortly thereafter that I discovered masturbation. The panties helped of course. At first it was just a natural progression from feeling my erection through the sexy nylon of the panties. But after stroking myself to my first orgasm I knew it would be a regular part of my secret panty wearing.
All through junior high and high school I would steal panties from the hamper, or even clean panties from my sister’s drawers. I would wear them under my clothes around the house, and even when I was outside playing. On occasion I would wear them all night long when I was sure I would have enough privacy to get away with it.
And eventually the panties weren’t enough. I would try on their bras and slips, and even their dresses and skirts, whenever I had the opportunity. In fact, whenever I was home alone I would put on a pair of panties and often a dress or skirt, and then go about my business as if I was a girl and it was a normal day. Sometimes I would pretend I was on a date with a guy while I masturbated. Sometimes I would pretend I was a slut and imagine myself being ravaged, stripping my clothes off as part of the fantasy.
I was devastated when I got to the point where their bras and dresses didn’t fit anymore. But I never outgrew their panties. When I finally graduated from high school and moved out for college I was overjoyed. I was a little bit sad about not having constant access to my sister’s panties. But I quickly realized that I could finally buy my own and keep them in my room as long as I wanted. And fortunately I had a roommate that kept to himself so I was able to build a fairly nice collection of panties and assorted lingerie that was all my own.
Even better was when my roommate graduated two years ahead of me and I ended up living on my own. I no longer had to hide anything and I was able to wear panties, lingerie, and whatever feminine clothing I wanted, almost whenever I wanted. My wardrobe grew to include a couple dresses and skirts. I even found the courage to buy myself a realistic dildo after I discovered the joys of anal self-pleasure. From there my fantasies expanded to include being a girl on a date with a man and having intercourse, or being forcibly taken from behind by a guy or another girl with a strap-on. I would experiment with whatever I could think of, bringing myself to orgasm and sometimes tasting or swallowing my own cum.
But I knew that eventually I would want to grow up and have what most consider a normal life. I dated a bit, but always kept my personal activities a secret. On one occasion a potential girlfriend discovered my secret wardrobe and freaked out. On another occasion a girl caught me wearing panties on a date and called me a pervert before finding her own way home. So I knew I would eventually have to choose between my life with panties and a normal life with a regular girl.
The transition turned out to be easier than I thought it would be. Once I had met the right girl I was able to suppress my inner desires, at least enough to develop a relationship. And she was totally worth it. Vivien was beautiful, with long blonde hair that had natural waves, deep blue eyes, and full, luscious lips. She was well proportioned, with tits that were just the right size, a narrow but not-too-skinny waist, accentuated by those wonderful, womanly hips, and lusciously smooth legs. And she made me laugh. She was one of the few people I had ever met that could make me feel at ease in just about any situation.
We started slowly. But after only a month or so I was sure she was the one. So I boxed up my feminine clothes and very reluctantly dropped them off at Goodwill. It was a bitter-sweet parting, and I actually turned around once and almost changed my mind. But once the deed was done, I was able to fully commit to Vivien. Our relationship grew quickly after that. We spent every minute that we could together. The sex was fantastic, but the way she made me feel when I was around her was far beyond anything I had ever hoped for.
We dated for a year before getting engaged. And another year later we were married. By then we had both graduated from college and found fairly good jobs. It was a wonderful life. The only downside was when our work schedules didn’t mesh. There were times, not extend times but often entire weeks, when Viv would be heading to work just as I was getting home, and we would have to wait for the weekend to spend any time together.
It was during one of those periods when my secret passions came back. I would say it was a gradual process, but in reality it happened almost overnight. I was alone one evening, folding some laundry, when the feel of her panties in my hands brought everything back. Without a second thought I had stripped off my clothes and had the panties on. And I thanked my lucky stars in that moment that Vivien and I were nearly the same size. She’s a hair under 5’8″ and I’m just a shade over 5’10″. And we’re both slim. So her clothes, as I discovered that evening, fit me rather well.
For the rest of the week, while our schedules kept us apart, I tried on nearly every stitch of clothing she had. Most of it fit, and quite a bit of it I liked a lot. So from that point on I would wait for the times when our schedules were off and I would wear her clothes around the house.
Eventually I grew bold enough to sneak a pair of panties either from the hamper or from the drawer and wear them under my work clothes. I even had a couple of close calls at work, and once at home, that made me nervous about getting caught, but not enough to make me stop.
But virtually all roads lead to a fork. And eventually the inevitable happened. On this fateful day I had worn a pair of Vivien’s panties under my work clothes. They were so comfortable that I actually forgot I was wearing them. She he was supposed to be working that evening so I wasn’t afraid of getting caught. But on this occasion she had actually gotten the night off, having traded with a co-worker who wanted a night off the following week. So when I got home I just naturally started to change my clothes. She was sitting on the bed, asking me about my day and talking about random things that had happened to her over the week. Without thinking I pulled off my shirt and then my pants. And before I realized what was happening I was standing in front of her wearing only my undershirt and a pair of her pink panties.
I held my breath, hoping she wouldn’t say anything. But her silence wasn’t because she didn’t notice. She was sitting on the bed, her mouth hanging open, too stunned to speak. Not knowing what to say I just kept silent myself, wanting to hide but unable to move.
Finally Vivien broke the silence. “What in the hell is going on? Why are you…wearing my panties? What…?”
I just hung my head, knowing that my secrets had finally come to light. There was no way out. I was totally caught. I could lie my way out, but what would I say? So after a long, pregnant silence I turned and was about to head into the closet to find something ‘normal’ to change into. But as I started to walk away she stopped me.
“Oh no you don’t. Don’t you dare walk away. You get your sorry…panty-wearing…sissy ass back in here. I want to know what’s going on.” Her tone was demanding. And since I was caught I figured I may as well get it over with. It was the moment of truth, if you will. From this fork in the road I would either spill my secrets and have Vivien walk away in disgust, followed by a nasty and humiliating divorce, or I would spill my secrets and hopefully find that she can live with it. Either way, I couldn’t pretend any more. Even if I hadn’t been caught, the desires were becoming so strong that it was only a matter of time.
I walked back to the bed and stood in front of her. Her eyes went back and forth from my face to the panties I wore. And her expression was a swirling mixture of anger, disgust, and confusion. Then finally, “Start talking!”
And so I did. I started at the beginning, just as I have here. I told her about my childhood, and the discoveries that I made that changed me inside. I told her about the things I had tried, about the self-sodomy and eating my own cum. I told her about how she changed my life, but that our schedules had given me too much of an opportunity to regress, not that it was her fault in any way. And finally I told her how the desire had become so strong that I wasn’t sure if I could ever go back to pretending they didn’t exist.
It was a long story, but I held nothing back. And by the time I finished she had tears in her eyes. I had no idea if they were tears of pain or fear, or if she would ever be able to accept me. But it was clear that things had changed between us. And after a long silence she finally responded. Her voice was quiet, almost a whisper, and devoid of almost all emotion.
“I’m not sure what to think about…this…right now. I’m…I think I would like to be alone. Tonight.” Her meaning was clear. And while it wasn’t an outright rejection, I knew I would be sleeping in the guest room.
I turned around and started picking out some clothes for the next day. But when I started to pull a pair of briefs out she stopped me. “Oh no. There’s no point in stopping now. No reason to…pretend…anymore, right?” Then she got up and pulled open her own drawer, taking out a pair of thong panties and a matching cami. Tossing them to me she said, “You may as well wear these. If it gets you off so much you should definitely wear them.” Then she grabbed the briefs from my hand and tossed them into the trash before going into the bathroom and shutting the door behind her.
I picked out some work clothes and took them, and the panties and cami she had given me, and headed out. I could hear her mumbling as I walked out. I couldn’t really hear everything she said, but the words “pervert” and “sissy” came up more than once.
I got maybe two hours of sleep that night before having to get up for work. Not knowing how late she had stayed up I did my best to be as quiet as possible. I showered in the guest bathroom and then put on the thong and cami she had thrown at me. They were actually one of my favorite sets, and I had worn them on several previous occasions. Had I not been facing an impending inquisition and possible firing squad I would have been overjoyed in that moment. But reality was heavy, so I finished getting ready for work and left.
We still had two more days of opposite schedules to go, so Vivien was gone by the time I got home. For the most part I was glad. I wasn’t ready to get into an argument, if that’s where this was heading. But part of me was disappointed. After a long, nearly sleepless night I really needed for us to talk about things. But either way, it had been a long day and I needed to unwind.
I went into our bedroom to change my clothes. As I started to take off my pants and shirt my mind went back to the day before. I actually found myself wishing Vivien was there to watch me undress, to see me wearing her panties again. I settled for watching myself. I stood in front of the mirror and stripped down to just the thong and cami I had worn all day. In all honesty I had really enjoyed wearing them. They felt great and fit well. I was still a man, so I looked a little silly in the mirror. But seeing myself wearing thong panties and a cami still sent a tingle through my body.
I went to the dresser for some clean socks. But when I opened the drawer I immediately saw that all of my underwear was gone. Vivien must have taken them out during the day. I had no idea what that meant. The second thing I saw was just as curious. Where my underwear should have been were two pairs of panties, one with a matching bra and one with a cami similar to the one I was wearing. There was also one of Vivien’s old nightgowns. And on top of them all was a note.
It was brief, but concise. “Tim, I’m still not sure what to think about this. We definitely need to talk, but will have to wait until Saturday. Until then, this should be enough to get you through. (If not, you’ll have to get some panties from the hamper.) I threw out your old underwear, figuring you wouldn’t be wearing them anymore. You should probably sleep in the guest room until Saturday too. Until we figure out the future of our relationship I don’t think we should sleep together. Still, you should be comfortable, so I’m giving you one of my old nighties. –Vivien.”
That was it. But to me it said a lot. There was very little emotion in the note. But at least she hadn’t thrown me out. And she had left me some of her panties to wear. So perhaps there was hope for us after all. I took the silky, feminine items she had left me and carried them into the guest bedroom. That’s when I found another reason to hope. On the bed were laid out two of Viv’s summer dresses. On them was another note that said, “You may as well be comfortable, if this is what you really want.”
Immediately I pulled on one of the dresses. It had been a few weeks since I had worn one, and it had been nearly three years since I had worn one without fear of someone finding out. I still had some fears about how everything would turn out. But at that moment I felt more free than I had in a very long time. It felt great to walk around the house in the dress and not have to worry about when Viv would be home.
And going to bed was a new adventure altogether. I had worn her nighties around the house before, but was never able to wear one all night long. It felt very sexy and feminine. In fact, it felt so good that I ended up masturbating twice before I was able to go to sleep.
The next day was Friday, and it went pretty much the same as the day before. I showered in the guest bathroom and then put on the fresh panties and cami that Vivien had left for me. Putting my work clothes on over the panties I headed off to work. All day long I kept thinking, ‘I could really get used to this. I just hope Vivien is still around while I do.’
Friday evening, though, went a bit differently. Not knowing how things would change after the weekend I stopped for a few personal supplies on the way home. Some things I was running out of, some things we usually shared but may not be sharing in the future, but some things I just wanted to change. Mainly I wanted to get myself some lady’s deodorant, always having preferred the feminine scent to the more manly scent of my own deodorant.
There were no notes for me when I got home, and no more gifts of clothing. So I slipped on the same dress I had worn the evening before and went about my evening. But my mind kept fixating on two things. I was worried about how our talk would go in the morning. By the end of the weekend I would either be starting the divorce process, or starting over with Vivien but with no more secrets.
But no matter how our talk ended, I was going to be wearing panties for the foreseeable future. There was no way I was going back to briefs. There was really no reason to. Ever. And so I found myself lost in thoughts of the changes I would make. While I never actually wanted to be a woman, I had always preferred things that were feminine, preferred being feminine. Before I met Viv I had actually shaved my legs and body a few times. I loved the way a woman’s legs felt when they were freshly shaved, and always wanted to experience that for myself.
So before going to bed that evening I found myself doing something else I hadn’t done in over three years. I took my electric shaver, and, using the mustache trimmer I trimmed the hair on my legs and ass down to just stubble. Then after a soak in a hot bath I sat on the edge of the tub and shaved my legs smooth. I was no expert, at least not yet, so it took me nearly an hour. (It’s not so easy to shave behind your knee if you hardly ever do it.) But after a final rinse in the shower, which also served to clean out the tub, every part of my body except my head and arms were completely hairless and smooth. I wondered what Vivien would think about it. But I knew that it was basically all or nothing from this point. My skin tingled as I dried off. And not wanting it to dry out I stole Vivien’s moisturizer and rubbed the lotion all over my freshly shaved body.
Now that my legs were totally smooth, the silky nightgown Viv had given me felt even more amazing on my skin. And like the night before I ended up stroking myself to orgasm before I was able to sleep. I wondered if this would become a nightly need, and I fell asleep hoping it would be Vivien taking care of that need in the future.
I slept pretty well considering everything that was going through my mind. But I still woke up earlier than usual for a Saturday. I figured Viv would sleep longer since she hadn’t gotten home until after midnight. So I got up and got dressed, putting on the last clean pair of panties I had. Like the others, I had worn them several times in the past, and liked the way the looked and felt. The bra also felt nice. I had only worn it once before, but it fit quite well considering I had no tits to fill it. Finally I slipped on a clean dress, and after an application of my new feminine deodorant I headed out into the kitchen for some breakfast.
Walking around the house in the dress felt great, especially the feeling of my smooth skin as my legs rubbed together and against the dress. And knowing Vivien was actually home and could walk into the room any minute brought an added thrill. But I still found myself jumping at every sound, wondering when Viv would finally get up and what she was going to say when she saw me.
It was mid-morning when Vivien finally emerged. She was looking rather casual, wearing a dress very similar to the one I was wearing. She walked into the kitchen and poured herself a cup of the coffee that I had started when I heard her in the bathroom. Then she came into the living room and sat down in a chair across from me.
“Good morning,” she said very cordially. “Did you sleep ok last night?”
“Actually, I slept pretty well last night,” I answered. “How about you?”
“Not bad. It was a bit hectic last night so it took me a bit longer to relax. I’m glad it’s Saturday.”
This is the next day in my experience of working with Trista. If you haven’t read the prior chapters, please do so. Don’t hesitate to contact me with feedback.
I awoke to the sound of my phone ringing; Trista of course was on the other end. She told me to have my stuff packed up, that I’d be switching rooms. She explained that instead of us having two separate rooms we may as well upgrade and get one nicer room since she was spending a large majority of her time in mine. I wasn’t going to argue with that, these Vegas hotels have some very nice rooms.
I also thought that maybe if we were sharing a room, I might have a better chance of getting some relief.
Each morning my balls were still sore and throbbing from being so full, but it was so much better than at night. It was like they got some rest themselves as I was sleeping. Trista had told me that I had 20 minutes to pack before she got to my room. She told me to pack up everything but the clothes I had on. When I reminded her that I still had on her bra and thong from the night before, she said that’s fine, to pack everything up but what I was wearing.
I didn’t like the sound of that but I wasn’t in much position to argue, nor did I have time to put much thought into arguing. I had a lot of packing to do.
I finished just in time, as I heard a knock on the door. I confirmed via the peephole that it was indeed Trista and let her in. She came in carrying a plastic bag and immediately looked me over. She had on black spandex tights and a red zip up vest. (Naturally I looked her over too in that outfit.)
“Well how did you like sleeping in my lingerie,” she asked. I admitted that the outfit was and is a turn-on, but also said I had a fitful night of sleep and mentioned the reasons why. She seemed sympathetic as she listened although she made no promise of any sort of relief coming my way anytime soon.
She asked if I had packed everything and I told her that I had. She dug out my tennis shoes and a pair of socks from my bags as there was another knock on the door. Trista told me to sit on the bed and not to move. It was a bellhop from the hotel staff who was there to move my bags. Unfortunately for me, Trista let him in the room as I was sitting on the bed. He saw me and tried to stifle a mocking smile but couldn’t totally suppress it as he saw me sitting there in Trista’s undergarments. Trista noticed his laugh and said, “I suppose you see something like this a lot.” Ramon (whose name I learned via his nametag) sort of laughed and said that not as often as people think. Trista then introduced herself and said that since it doesn’t happen often he should have a story to tell so she made me stand up and turn around so the bellhop could fully see me. When Trista asked what he thought, Ramon said, “he looks pretty good in it actually, but not really my type.” That made Trista laugh and she thanked Ramon and asked him to bring the bags up to our new room telling him we would return the keys to the front desk soon.
My face was now as red as the lingerie I had on, and I was growing concerned about what it was that I exactly was supposed to wear now that all my clothing had been removed by Ramon, except for what I had on and the shoes and socks Trista had dug out of my bag. It would certainly make a strange ensemble I thought.
My question was answered immediately as Trista pulled out of the bag a pair of royal blue spandex tights and a long sleeved red spandex shirt similar to what I had tried on the day before.
I started to protest that I couldn’t wear this outfit, but Trista cut me off. “Look, you’re going to take off the lingerie, we’re going to take off the chastity device, you’re going to put on nothing but spandex, we’re going to go work out, you’re going to be hard the entire time, everyone will see your hard cock in the spandex, then we’re going to go our new room and we’re going to put that little cock of yours back in the cage where it belongs. Is that understood?”
I answered, “Yes Ma’am.” At the present time, I didn’t have many bargaining chips. All of my luggage had been moved, the only clothes I had were the ones I was wearing and Trista didn’t seem to be open to any type of discussion on the subject.
I followed her instructions. Immediately my cock sprang to full attention as soon as it was released and remained that way for basically the entire workout. That includes the trip down the hall and the elevator and past the 30 or so people we passed on the way to the workout room. It also includes the 6 or 7 people in the fitness center. You know how they have those Viagra commercials that if you have an erection that lasts four or more hours to contact a doctor? That’s what I felt like.
When the workout finally ended, which was about an hour later, we headed back up to what I thought was going to be our room. Instead we headed to the front desk. It turned out that “conveniently” we had to return our keys from our previous rooms. So I stood there as Trista conversed with a cute young gal at the front desk named Kristin. I stood there nervously. On full display, I didn’t know if I should leave my back to the rest of the lobby allowing everyone to see my ass in the royal blue spandex or to turn around and cover my cock with my hands crossed in front of me. Neither seemed like good options as I tried to avert the humiliation of being in that outfit in the lobby. I wasn’t paying much attention to Trista’s conversation when I suddenly saw Ramon coming up to the front desk. “Ah, Ramon was so helpful this morning,” Trista told Kristin. I felt my face become totally flushed as Ramon received Trista’s praise. I knew he was going to tell others what he had seen earlier if he hadn’t already done so.
Finally Trista wrapped up her conversation and we got directions to our new room. I was very happy to finally get out of there. As we walked down the hall to the elevators, Trista kept the pressure on me, telling me things like people were probably staring at my ass or that the people we just passed looked down at my cock or that Ramon was telling Kristin about what he had seen earlier. I have to admit, the mental games she was playing certainly had an effect. While they were frustrating, it was such a turn-on at the same time. My cock had been hard for about 2 hours now and it wasn’t going down until she wanted it to.
We finally arrived back at our new room and before I was able to look around and admire the upgraded suite, Trista led me immediately to the kitchenette. There she had a bucket of half ice, half cold water on the counter. She had me lower my tights and she grabbed my cock in her hand. She stroked me up and down very sensually and whispered to be sure not to cum no matter how much I wanted to or I would be sorry. But boy did I want to.
Her hand then moved to my balls and she took them in her hand and squeezed, gradually increasing the pressure. I moaned. She smiled and then slowly she dunked my cock into the frigid water. Trista then knelt down in front of me and put me back into the chastity device as soon as I was flaccid enough to do so. “Now you can look around the room,” she told me as she went to shower.
I did look around the room, and it was a much nicer upgrade that the one I’d had before. Instead of my window overlooking the pool, there was now a little balcony off a patio window. We were 6 stories up, but below us was the strip. It was a pretty sweet view. The entire room was wide open, similar to what I remember seeing in a few movies with the floor to ceiling windows and the balcony that overlooked the strip. The only part that was separate was the bathroom. Also, we had a kitchenette, a couple of couches and a huge king sized bed. I liked that, I figured worst case, with only one bed; I could at least fondle Trista as we slept. Always the optimist I am.
Trista came out of the shower stark naked and into the room. She told me that we had a big day planned and that we had to get going, but first I had something I had to do. She had me kneel before her and she grabbed my head and pulled it into her pussy. I knew what to do from here and my tongue went to work. She ran her fingers through my hair as I ran my hands up and down her legs as my tongue darted all around her pussy. When Trista caught her breath after cumming she said, “You lick pussy almost as well as you sucked that fake cock last night. I am beginning to wonder which one you like best.” With that she told me to shower quickly so that we could get going.
In the shower, I watched as the water cascaded down my waxed legs, looking at my cock in its chastity device, and my mind kept wondering why in the hell I kept getting so turned on. I never before had any interest in any of this stuff, why was it turning me on so much now? And of course, as I kept wondering and replaying the past few days in my head, my cock tried to stiffen and my balls began to ache even more. I quickly flipped the shower to cold and decided to give the old cold shower remedy a chance. At this point, I was so frustrated with not being allowed to cum that I would try anything.
The cold shower didn’t hurt at all but it didn’t help as much as I would have liked. Trista told me to quickly get dressed. Getting to choose my own outfit this time, I went with jeans and a tee shirt.
In the car, I asked Trista where we were going and she told me we were heading out shopping. We pulled up to a little strip mall and went into a boutique that upon walking in seemed to specialize in lingerie.
As we walked in and were greeted by a very cute clerk who introduced herself as Kim. Naturally, when Kim asked what she could help us with, Trista said that she we were there looking for lingerie, however I think I was more surprised than Kim was when Trista told her we were there for things for me to wear.
I looked at Trista, and she said in an even tone, right in front of Kim, “Well we can’t have you always wearing mine like you did last night.” My face turned as red as could be as Kim giggled at that comment. Trista then added, “He really seemed to like it” with a wink.
From that point on, it didn’t seem that I had much need of being there, as Trista discussed with Kim exactly what I should get and didn’t include me in the conversation at all. Occasionally, they would hold something up in front of me but by and large I was forgotten for much of the next hour. That was just fine as I was embarrassed as could be and my balls were continually aching as I kept picturing myself in the outfits they were looking at.
Finally, all the outfits were picked out and Trista called me over and held up three outfits: a black teddy, a red chemise with matching thong and a black with white pinstripe baby-doll with a matching thong. Trista asked, which outfit I liked best of these three. I looked them over and selected the pinstriped one.
Trista then handed me the outfit, and said, “Ok, here you go, try it on.” When I started to stammer she also handed me a package of black thigh high stockings that she said would complete the look. I looked at Kim who just had a smile on her face as Trista pushed me into the dressing room.
As I stripped down, my heart was racing, my balls were aching and my cock was testing its bonds. I put on the thong first, and then I began to put on the stockings. I have to admit, that was quite the sensual experience, and the feel of the stockings against my smooth legs was definitely pleasurable as I was testing the cage once again. I finally slipped on the baby-doll top as Trista was telling me to hurry it up.
When I was ready, I opened the door, and peeked out seeing Trista still talking to Kim. I got their attention and even though there was no one else in the store, I didn’t think they wanted me to go over to them. I was wrong.
“Come over here,” Trista demanded. I walked over, feeling very much on display as they had me turn around a few times. My cheeks were burning with humiliation. They both said I looked very nice and to which I thanked them. Kim mentioned that it seemed I filled up the thong quite a bit. Trista laughed and explained that that was definitely not the case. She told me to pull down the thong to show Kim the chastity device I had on.
Both Trista and Kim knelt down in front me as Kim inspected it and Trista took her through the highlights of the device, namely that she held the key and I couldn’t get hard at all. Trista then explained how she basically owned my cock and could do with it what she pleased. With that she wrapped her hand around my still exposed balls and squeezed, gradually tightening her grip until my knees began to go weak. “Isn’t that right slut?” she asked me.
I couldn’t form any words as she crushed my balls in her hand but managed to get out a nod and she then released them from her grip. She told me to change back into my regular clothes but to leave the thong and the stockings on which I did. Trista then had me thank Kim for all her help and we headed to our next stop.
Our next stop was at a shoe store. This wasn’t your typical Payless place, this specialized in very high heeled shoes, that I believe this store could be best be described as a place where strippers would shop for their shoes. Upon entering, once again we were greeted by a clerk; she was a short brunette who introduced herself as Heather. When she asked us what we were looking for Trista told her that we were in the market for some “eye-popping fuck me shoes, something that leaves no doubt.” Heather giggled a bit and said she had plenty of options as she led us across the store.
We arrived at a large wall of high heeled shoes, almost all at least 5 inches. Trista eyed the wall before selecting a black strappy pair, with a 5 inch stiletto heel. Heather complimented her taste and asked what size she was. Trista smiled and said, “oh no dear, these aren’t for me, these are for him.” As was becoming standard for me, I could feel my face blush as I could also feel myself strain against the cage once again. When I told her my shoe size she got out a pair for me. Trista told me to take off my shoes and socks to try them on. That was when I was reminded that I had left the thigh high stockings on and now my nylon covered feet would be seen. Trista must have noticed my hesitancy and decided to explain, in full detail to Heather exactly why I had nylon covering my feet. “We just came from a lingerie store, last night he was wearing mine and while he looked quite nice in them, I felt it would be better if he had his own and he wanted to keep the stockings on.” Heather had a sly smile on her face as I was putting the shoes on. My jaw dropped when I heard Trista ask Heather if she wanted to see some pictures.
Trista then took Heather through picture by picture of the previous night and all the pictures she had taken of me in her lingerie complete with the pictures of me sucking on the dildo. I was mortified.
Finally I had the heels on and I tried my best to stand up. Trista told me to walk down the aisle so they could see how they looked. I went slowly, making sure that I would not topple over and putting one foot in front of the other. Trista laughed as Heather mentioned to her that I appeared to be a natural in heels and said I was “workin’ it.” Trista loved them on me, and thought they looked great. So great in fact, she told Heather that I would just be wearing them out to the car. When I started to protest, Trista said we parked right in front of the store, at worst people who I would never see again would see me, what would be the big deal. I relented and after we paid, I did a little walk of shame out to the car in my new high heels. Trista however wouldn’t let me in the car right away, she made me stand outside the door, pleading with her to let me in until an older couple walked by and saw me standing five inches taller than I normally would be in my new heels.
In the car, Trista told me that she had a couple stops left. We had an uneventful (surprisingly) stop for a wig for me. Luckily Trista had allowed me to switch back into my normal shoes before we went in. For our final stop we pulled up once again to the sex toy store we had visited the previous day. Trista told me to just wait in the car, she was picking something up. She was inside for no more than 5 minutes before coming out with a large plastic bag that seemed very full. When I asked what she had all gotten, my fears were confirmed when she told me to be patient and that I would find out soon enough.
We arrived back at the hotel and went back to the room and she told me how much fun she had had with me today. She wanted to see how I would look in my new outfit. She told me to go into the bathroom and to remove my clothing and to come out in the black bra and thong set, complete with the wig, stockings and heels.
I went into the bathroom and stripped off my normal clothing. I put on the outfit as directed. When everything was on, I looked at myself in the mirror. I had to admit, that I thought I looked pretty good. Not a supermodel by any means but from across a room I could certainly be mistaken for a woman. I turned around and admired my ass in the mirror. I was amazed at how different it looked with the heels on. Once again, I thought I looked pretty good all things considered. The more I admired myself the more my cock tried to strain against the cage it was still locked in and the more my balls started to ache once again. I didn’t know where this was going but I had to admit that it did seem I was being turned on by it all.
I opened the door to the bathroom and walked out, looking for Trista. She was sitting at a table across the room with a robe on sipping on a glass of wine. “Come over here and let me see you,” she told me. Once again, I slowly walked across the room, trying to keep my balance. I was watching where I was walking and I heard the click of her cell phone taking a picture of me in this outfit. I looked up and she just smiled. “You looked so cute I had to have a picture,” she said.
Once in front of her she was glowing, telling me she definitely liked what she saw. She ran her hands across my smooth body, up and down my legs and my ass. She cupped my balls through the thong and asked how these were doing I told her that they hurt and ached, even to the touch. She said, “Oh no, that’s not good. At least not for you, I happen to like you having that feeling.”
Trista then told me to kneel down in front of her and opened her legs. She had nothing on under her robe and her pussy was once again in my face. “Now, you know you that you weren’t fully cooperative today. You’ll have to be punished for that, but if you do a good job on your knees I might take go a little easy on you. Now get to work.”
With that she pulled me into her pussy and I did indeed go to work. She was so incredibly wet, which she told me, was from watching me walk in my new outfit. That stirred my cock even more and made me work all that much harder to try to get her off. After 10 minutes and 2 orgasms she stood up in front of me, her robe still open, her large breasts and shaven pussy still visible to me, which didn’t help my aching balls at all.
Trista walked across the room and came back with the paddle in her hand. She told me to bend over the table and to accept my punishment. I did as was told and she took a lot of time running her hands over my ass. She asked me, “Do you like being in this position? Knowing what’s coming, so open and exposed and me being behind you like this?” When I admitted that I was turned on by it she cupped my balls and said that was what she wanted to hear. She had me lower my thong and she proceeded to give me 20 smacks with the paddle alternating from side to side. When she was done he told me to hold still that she wanted to get some lotion to rub on my ass as it appeared to be pretty red.
Chapter 1: Friday
It all began that evening before my sister Katie’s wedding.
Well, I should mention that the big change happened that evening, as “everything” began much earlier. My name is Peter. Together with my family I live in a big mansion in southern England. I have three sisters older than me: Linda is 31 and lives in the West wing of the mansion. She is married to Harold and teaches English and physical education in our local preparatory school. Linda has always been kind of a replacement mother for me and my two other sisters because my parents are both lawyers and spend most of their time in their office downtown.
Katie is 28 and lives with her fiancee in the East wing of our large house. She currently studies modern history (at least I think so) at the university after having studied algebra, Greek history and whatever else. Her future husband is very proud of his well-educated wife-to-be and his income allows him to pay all of her expenses. Katie is a very pretty woman — she has blue eyes, long blond hair and the face of an angel. And people tend to think that she would be one — but deep inside of her a devil is living. If you don’t do what she wants — beware! If she’s angry — you better run for shelter.
My youngest sister is Nelly. She became 20 last week and is six years younger than me. She is in the middle of an apprenticeship for a medical secretary. Nelly is a very nice girl and we understand ourselves very good. We often talk and have tea together.
I run a small computer consulting company since I finished my studies two years ago. Although I have rented a small office downtown, I do most of my work from home — who could live without the internet, today? And such, I am the family member that spends most of its time at home, followed by the parlourmaid or the gardener maybe.
The mansion is quite ample, and all our units have separate entrance doors so that we do not need to meet ourselves unintentionally. Of course, there are some connection doors, but these are closed most of the time. For convenience, we share some facilities of the house like the laundry. Why buy an own washing machine and a tumble dryer if it’s possible to use mum’s? No child would decide differently, correct?
Adjacent to the laundry is a large room with wires to dry all clothes, which cannot use the dryer. Long rows of wires are used by our maid to hang clothes on to let them dry in the air coming in via a number of windows. These are rather high in the walls for the room is more or less the basement of the mansion. The windows are covered widely by shrubbery at the outside and therefore, it is not possible to directly look into the drying room.
In this room my love for female clothing started many years ago.
I remember one afternoon when I was alone at home. My sisters were at school or at the university, the maid already left and my parents — of course — were at work. I don’t recall why I went downstairs but the drying room was filled with some of my mother’s and my sister’s evening gowns. My parents hold festivals two or three times a year and the week before such a festival was filled with preparations of all kinds. And one of these preparations was cleaning of the clothes we would wear that evening. Needless to say that my tuxedo was hanging on a wire as well.
But my primary interest was on the lady’s clothes. They were nearly dry — or they actually were dry and the possibly the maid had forgotten to pick them down this day. So I strolled through the rows of clothing and touched everything and enjoyed the feeling at my skin and and the rustling in my ears. This lead to a big erection in my trousers.
At that time, I was still smaller than my mother and Linda. And somehow, the idea arose to step into Linda’s floor length evening gown and play girl.
After this first cross-dressing time, I did this many times again. I totally grew up, but I was still only slightly larger than mum and Linda, I am nearly of the same size than Katie (the width of her breasts is around my stomach). Nelly is smaller than me so that I can only wear some of her wider clothes like skirts with elastic bands at the waist.
Howsoever, I started to wear the ladies clothes before they were washed if they weren’t that dirty. Sometimes, a little accident happened, but this was much less uncomfortable with clothes, which needed to be washed anyways.
And during all the years of cross-dressing, everybody was clueless about my laundry activities. Or at least, nobody said a word nor mentioned any hint that something strange was going on. Even our parlourmaid did not get suspicious — okay, she was already old years ago. And the laundry was my playground.
Like this evening before Katie’s wedding. I didn’t went down to play because the mansion housed a number of wedding guests this evening. I wanted to check for some clean socks, which I could wear with my tuxedo. Mum had bought new clothes for all of us, or at least had paid for them.
When I entered the drying room, my eyes were locked by Katie’s wedding gown.
The first thing I noticed was it’s bright and shiny white. She would marry in satin! I thought and my erection began to grow instantly. Fabric and fabric covered more than three wires. They had put it on the wires to avoid the fine fabric touching the ground. I could observe lace around the hem, square yards of clean white satin, and embroidery on the top part and the sleeves.
My left hand instantly touched my erection through my trousers. I went closer to the bridal gown and touched it with my right hand. What a feeling! The fabric was so soft and heavy. I could hardly resist to put it down and jump into it. I was sure that it would have fitted me. I touched the dress with my right hand whilst my left hand massaged my stiff penis. My eyes found a long crinoline hanging beside the marvelous gown.
Shall I do it? Or not? I would certainly stain it with my sperm. I would not be able to avoid that. I was becoming so hot that I thought I would ejaculate even before I wore it. And then, Katie would get angry. Or even more!
No, I couldn’t dare to use her dress — now. So I would have to wait. Would she let the maid clean it after the wedding? I asked myself. Or would she let it be done by some professional downtown?
Now or never?
While my erection grew to new heights, I heard a noise behind me.
Before I could imagine what was going on, I heard Katie’s angry voice.
“What are you doing there, little brother?”
My face blushed and I retracted my hands instantly.
“What — I can’t believe it — you are masturbating while playing with my best dress ever?”
“I…” I tried to say but my throat was dry and I stared into Katie’s angry eyes. My erection was already down, but I was sure that she could see the wet spot in my trousers.
“My little brother gets aroused by touching woman’s clothes…” she said and shook her head.
“I…” another unsuccessful try.
“Touching?” she asked. “Are you — maybe — some of these poor little shy boys with a woman in them? A trans-ves-tite?” she stretched every syllable. “I cannot believe that.”
“Let me explain…” I found more words, but she cut off my sentence.
“This is not the first time you do that, right?” she asked. She had her hands at her hips, and now her face got red as well, but hers for anger. “In the past, I sometimes could not understand why some of my stuff was ripped. You were that!” she stated and raised her hand to slap me, but she regained control again.
Slowly she yelled: “You ripped my clothes because you wore them for what ever reason!”
“Please excuse…” I gave it another attempt. But again she cut me off and her voice got more sharply.
“I needed to get my favorite clothes repaired because my stupid little brother wore them and played with them! I would have never wore them again if I had known that!
And now he wants to do the same with my bridal gown. On the evening before my wedding! He plays with my bridal gown!”
Now I shook my head. “Please excuse my dear sister, it was a mistake! I never…”
She interrupted me with a very low voice and accentuated every word: “Did you ever ejaculate into one of my clothes?”
I became as red as a hot iron. And I felt such a shame that I could have sunken into ground and had disappeared.
I opened my mouth but I did not find a word.
“Confess honestly!” she requested with the same low, dangerously sounding voice. She stared at me and her beautiful eyes seemed to have changed their color into a deep steel blue. Her hands still stuck in her sides.
I still was not able to say a word. My face was burning and I never felt such a shame before in my life.
“Confess!” she shrieked and stepped one step closer to me.
With a very, very low voice I answered: “Yes.”
Next I felt was a giant slap into my face. And another on the other cheek. I could have cried out, but I felt guilty and accepted the punishment.
“We are not done with each other!” Katie screamed. “You will receive your punishment and I promise you, that you will never — never — never wear any of my clothes again. Did you understand that?”
She cried again louder: “Did you understand that?”
“Yes. – Please don’t tell mum…” The boy in my 26 year old body took control.
“What?” she asked and I had the impression that she would start laughing in a second.
“Don’t…” she cut me off instantly.
“I will tell the world! The world! And mum will get to know it from everywhere!”
“No!” I replied fearfully.
“You will have only one chance that I rethink that.”
“What do you want me to do?” I took the chance instantly.
“You will do everything I tell you. Got that?”
“I’m not your sister anymore. I am your Mistress.”
“What?” she cried. “Didn’t you understand?”
“Yes, Mistress.” I answered without thinking about the importance of this word.
“God, my little boy. Now, my instructions: You will never touch anything again, which is mine. Understood?”
She slapped me again. Now only on the left cheek and not so hard as before but it hurt.
“Yes, Mistress.” I corrected my answer after the slap.
“Tomorrow, you will be my best man as planned before, and you will play your role as rehearsed.”
“On Sunday morning, you will report at ten o’clock sharp in our unit.”
My breath caught. I saw her hand raise.
“And now: Leave this room! And never come back again tonight!”
I nearly run and crossed her at a safe distance. I had the impression to leave the cave of a dangerous dragon. At the outside, I took a deep breath. My mind seemed to stumble. I sat down and watched people preparing the wedding at the large lawn area outside the mansion. I couldn’t admire the wonderful evening with warm air in this mid July. My sister had caught me and found myself wearing her clothing. Something in me broke down.
Welcome back for another story in the Marion series. While this outing has similar antics as the other Marion stories, it also involves so much more. Consider this not a continuation or the official story, but another variation, another version that could have been. And, for the record and fair warning, it does involve male on male so if that’s not to your liking backclick on out and find something more to your taste to enjoy. If you read on I hope you enjoy the kink, baby.
Finished primping, I sat down on our buttery soft brown leather couch and waited for Marion to finish dressing. I crossed my legs and registered the sensual whisper of my sheer black stockings, nylon on nylon, felt the hem of my rich wheat yellow microfiber sleeveless front snap dress shift and drape on my upper thigh.
I smoothed my dress on my lap and thought how I love gathering a stocking with manicured fingers, leaning down and feeling my hair brush across my bare shoulders and cheeks, feeling my earrings and necklace tug and sway, feeling the weight of my bracelets and hearing them clank and jingle, pointing a manicured toe, then pulling the stocking up my bare leg and experiencing the utter femininity of the act and the glorious feel of that gossamer fabric as it flows up and up and up my toned thighs, then carefully adjusting the hem so very, very high. It never fails to arouse me.
I reached out and picked up my champagne glass with my dominant hand, my cock hand. Marion calls it my cock hand because it’s the hand I most often use to reach out for cock. The hand that I most often use to wrap manicured fingers around a hungry cock before taking it in my soft mouth, eager to hear the man moan as my pierced tongue swirls around the soft-hard head and shaft. I looked at my cock hand and the tattoo thereon and up and I smiled and a welling of love for Marion coursed through me.
I tucked my hair behind an ear and my bracelets tinkled and my dangly earrings swayed and pulled, underscoring my femininity. I looked out the window of our two-story high-rise condo, across the boulevard to the wide, deep river, glassy in the evening and temporarily empty of traffic. A cloud blocked the setting sun and I appeared in the window’s reflection, a pretty, androgynous face made beautiful from the makeup magic that Marion taught me and further refined through girly classes I’d attended.
Thick, silky shoulder length hair. Specifically, straight hair, one and one-half inches below my shoulder at the ear. Two and one-half if shaping and curling was most often the case. Marion said that women to a certain age often wore their hair a full head length below their chin, perhaps eight or nine inches, which was fine if one was actually a woman. But one and one-half inches was the perfect flicking length for me. That, as a man dressed as a woman, I’d feel more feminine if my hair freely whipped and flicked across my face and shoulders when I was sucking cock or getting fucked.
Tonight my hair was purple. Marion enjoyed mixing it up a couple of times a year, especially during holiday seasons and my ordinarily sandy blonde hair has been blue, lime green, red, bright yellow, orange and a few other neon colors and combinations. It’s fun and I have to admit that I now enjoy the attention.
I stood and the reflection revealed a rather stunning woman with a slender, though boyish figure. Flat chested, of course. Average height for a male, altogether transformed into a beautiful and sensual creature.
I wore guardsman red round-toe booties with a six-inch heel. It amuses me that the current trend in shoes again echoes fetish wear. I wondered what the pony-play folks thought of it.
Fetishes. Mmm. We were going to a party, a gathering of people with shared interests, sex being the commonality and mostly anything goes being the true unifying factor. My cock twitched in my black lacy cheekie panty, but there wasn’t much to do about it since Marion had it locked down. She kept my cock under lock because she didn’t want me to be tempted to self-pleasure while she was at work. She said she wanted my cum for herself. Or for others to enjoy, including me. I was usually unlocked when Marion was around, but she was toying with me a bit tonight, the cheeky bitch.
I had no doubt that at some point in the evening I’d be on my knees, my lips around and down a thick cock or licking a sweet pussy. Or maybe on my back with my wheat yellow front snap dress ripped open exposing my sheer black lacy bra and hard cock, my panties yanked off, my legs spread wide and high, toes pointing to the ceiling, savoring the first angry cock as it spread me and speared me and claimed me. My heart beat faster at the thought.
As I waited for Marion I sipped champagne, fingered my silver necklace with a guardsmen red manicured finger and reflected on our happy years together…
“I had an erotic dream about you last night.”
Marion said this to me one Friday when we found ourselves momentarily alone in an office together. I mumbled something awkward and left to finish my break. Sitting in another office, I thought about what she’d said. I thought about the frequent eye contact we’d shared since I took the job. I thought about her brushing against me time after time. I nervously decided to return to where she was, to where she waited for me.
I entered the office and gently closed the door. Marion smiled and said, “I thought I’d scared you away.”
I shook my head and barely croaked out, “What was the dream?”
Her gorgeous face was framed by glorious black hair that flowed down her chest to the outward slope of her breasts. Her voice soft and low, Marion began telling me about her dream and after a few sentences her intent was clear to even clueless me and I gathered my courage and walked to her, leaned down and kissed her. Her lips were soft. Her mouth opened instantly and our tongues embraced and she tasted so sweet. We kissed and I cupped her full breast in my hand and she moaned into my mouth. After moments, hours, we heard a noise outside the door and pulled away from one another. I was breathing heavy, my head was reeling. Marion’s eyes gleamed. I was hard.
I was in my early twenties and recently out of grad school with a computer degree and hired on to write code. Marion was in her late twenties and led the marketing end of the small tech startup. I’d noticed her immediately, of course. A slender, raven haired beauty, always stunningly dressed. She was confident, carried herself with an air of authority and the men who constantly hovered around her, drawn to her as to a gravitational force, ceaselessly vied for her attention.
Marion said, “My place. After work. Follow me home.” She put a manicured finger to my lips and sauntered away, the faint smell of her perfume lingered. I was surprised at my boldness in kissing her. Even more surprised that she had noticed me, even more surprised she had approached me. A skinny nobody, code-boy. I was thrilled beyond words. And nervous.
Marion drove like a mad woman that afternoon, as if challenging me to keep up if I was to have her, as if she couldn’t wait to have me, or perhaps had changed her mind.
We stepped inside of her two story high rise condo and she turned and pushed me against the door, pressed her body fully against me, looked down at me, took my face in her hands and kissed me and said, “God, I want you.”
Marion dragged me up the black wrought iron spiral staircase, down the hall, past a closed door to her bedroom. She ripped off my tee-shirt, I kicked off my sandals and Marion unsnapped my cargo shorts and yanked the zipper down. She pushed my pants and silk boxers down and I kicked them off and her eyes widened and she took me in her small, cool, manicured hand and I moaned.
“Well, look at you, baby. I must say you’re a right bit bigger than I thought you’d be by the looks of you. What a delicious surprise.” With one hand she cupped my balls, her other hand ran up my back and she entwined her fingers in my shoulder length hair and pulled my head back hard, exposing my neck and she kissed it and bit it and squeezed me and scraped my nipple with a blood red fingernail and I moaned.
“Oh yes, I’m going to enjoy you and your cock, baby. No doubt about it.” She maneuvered me around and pushed me down on her king-sized bed. I lay back on the bed, propped up on my elbows, my feet on the floor, my cock thick and hard. Marion kicked my legs apart and stood between my knees. She ran her fingers through her thick, black hair and shook her head. She was a goddess.
Slowly, button by button, she worked her fingers down her white silk blouse. She shrugged it off and it pooled on the floor. She reached to her side and slowly lowered the zipper of her tight black skirt. Looking me in the eyes she pushed down her skirt and stepped out of it and stood before me.
I had never seen a creature like her before in my life. She was radiant. A cream colored camisole, lacy black panties, stockings and pointy black high heels. She removed the camisole in the way women do to expose a sheer, lacy black bra. I swallowed. I was numb. I had no reference for this moment, nothing to fall back on as to what to do next, how to proceed with a woman of such presence.
I’d had sex before, though didn’t consider myself experienced. A few fumbling though ultimately satisfying experiences with girls in college and grad school, and some other involvements. But this was a whole different dimension and I was paralyzed.
Marion crawled onto the bed, her right knee, her left hand, left knee, right hand. I fell to my back and she loomed over me, her hair cascading down and framing her lovely face. Her breasts straining against the thin fabric of her bra.
“Hey baby,” she whispered. “Wanna fuck?” I gulped and she laughed and leaned down and kissed me and her hair brushed my face and I moaned into her mouth. Marion kissed my eyes, my cheeks, my chin. I felt her cool necklace brush my skin.
She kissed and nibbled and bit my ears, my neck and worked her way down. She kissed my hairless chest. She lingered and kissed and pecked on a nipple. She lightly stroked my cock with the back of her hand and nibbled and sucked and bit my nipple.
Marion played with my other nipple, pinching and pulling and flicking it with her nail. She bit me and chewed me back and forth until my nipples vibrated with passion. Building slowly, kissing, nipping and finally biting and twisting them roughly and when she moved lower they sang with lingering, delicious pleasure-pain.
Her hair trailed and tickled down my chest and stomach. She tongued my navel and my cock throbbed. She kissed her way down and I felt her hot breath on my cock. My muscles were tense and I felt her breath on me and then a silky presence floated over and on me, tickling and taunting and tormenting me. Marion looked up at me and smiled and threw her camisole over my face and I felt hot moisture envelope me and I moaned as her tongue swirled around my cock.
I pulled the camisole aside and looked down at Marion sucking and licking my cock, her hand in sync with her mouth, making me delirious with pleasure. She reached up and put a finger in my mouth and said, “Get it wet, baby. Get it real wet.” I sucked her finger and moaned.
Wetness back there, a sharp point wiggling, insistent, slowly piercing me. Her small finger felt huge as it snaked up my rear and I moaned and spread my legs. Marion sucked my cock and moved her finger in me, pressed a spot and I felt a surge of pleasure I’d never known before.
Marion sucked and stroked and moved her finger in me and I moaned and my hands involuntarily held her head and I spasmed and came into her tender mouth. My breathing slowed, my muscles relaxed. And when Marion crawled up and lay on me I could tell her panties were off.
Face to face, Marion said, “Mmm, that was nice. You taste nice, baby.” She kissed me and she encouraged me find the barest remnants with my tongue. She pulled away, lifted herself and urged me to lie fully on her soft bed. She crawled up my body, I looked up at her as she sat astride my face, my arms pinned under her stockinged legs. She looked down at me and said, “Lick.”
I put my tongue out and licked her bare pussy, her sweet, bare pussy. Marion ran her fingers through my hair, took hold of me and instructed me in what she liked, what she wanted.
“Mmm, that’s nice, baby. Lick me just like that. Long and slow. Very nice.” I licked and she looked down at me and talked, her voice husky, “Bite my lips with your lips. Yesss, like that. So good. Now chew them. That’s a good boy.” I did as told and was rewarded with soft moans.
She shifted and said, “Now concentrate on my clit. Lick, nibble, flick. Oooh, yes.” Marion got quiet, her breath grew ragged, she moved on me, working my face against her and I licked and chewed and tried to make it good for her and she groaned and arced and rippled and came.
Marion settled back, moved back down my body. Slid back down and rotated her hips and took my hard cock into her tight pussy and I moaned as I slid into her hot cunt. She lay on me, still, licked my face and emitted a low growl of pleasure.
“God, I think I’m in love with your cock. So full, baby, you fill me up.” I put my arms around her, caressed her small back and bottom. Marion moved her hips, swiveled them on me, over me, around me in mysterious ways and the pleasure was immense.
I reached for the clasp of her bra and she said “Yes.” I unhooked it and she sat up and let it fall away. She sat astride me in her stockings and heels and let me gaze at her as she writhed on me. Her breasts were perfectly shaped, perfectly sized for her body. She cupped them for me as she wriggled her hips and squeezed her pussy on my cock and I moaned and stared at her. Marion looked at me and brought a nipple to her lips and licked it, bit it.
She smiled down at me and told me to raise my arms. I lifted my arms up and she put the camisole over them. She put my hands on her breasts as she worked the camisole down my arms, over my head, and pulled it down my body as I arced and shifted to let her have her way.
“You’re hands feel good on me. I like your hands on my body, baby. There, it’s on you. God, that looks so sexy. Doesn’t it feel sexy? That slippery satin on your skin?”
Marion leaned down, swayed a little from side to side, letting her nipples glide across the satin camisole. “So good. I love lingerie, the look, the feel of lingerie. I love how your cock feels inside of me.” She kissed me, sat up and put her hands on my chest. She closed her eyes and rocked on me. She bounced and rocked and writhed on me and she snapped and swiveled her hips and finally I rasped, “I’m coming.” I couldn’t help it, my hips thrust and pumped into her again and again and she cried out and I came and she moaned and clamped and finally flopped down on my chest. Her head next to mine, her breath finally slowing. I was still hard and could sense her broad smile.
“Whew! Mr. Code’s wild ride. I’ll buy another ticket, for sure.”
I laughed. I was hard.
Marion rolled us over, grabbed my ass and pulled me in tight against her. She kissed me. Her lips at my ear, “Giddy up, code-boy. Show me what you got. Make me feel it.”
Not being that experienced I simply went on instinct, past exposure and what I’d seen in porn movies. I moved my hips back and forth, side to side. I caressed and squeezed her breasts, bit nipples that she offered to me. My hips moved faster and I propped myself on my hands and pumped and thrust. I put my hands behind her knees and pushed her stockinged legs down and pounded into her again and again, over and over and heard her rasp, “God, yes.” I fucked her hard, as hard as I could; fast, wet slaps as our bodies collided. The camisole fluttered and danced with my movements and sweat trickled and dropped on Marion’s heaving chest.
Marion grunted, “Harder! Oh! I’m there!” and she arched and yelped and stiffened and I moaned and released and waves of pleasure washed over and through me.
My heart racing, I collapsed onto Marion. We caressed, stroked each other, ran our fingers through one another’s hair, soothed each other as we calmed. I could feel her heart beating in her chest. I finally rolled off of her, onto my back. We turned our heads, looked at each other and broke out in laughter.
Marion turned on her side toward me and caressed my face. “Nicely done. You’ll be pleased to know that that’s right up there with the best I’ve had in awhile.”
I blushed and said, “You’re the best I’ve ever had.”
“Mmm. You must have been around the block a time or two.”
“No? Then you’ve got good instincts, baby. You’re going to be quite the swordsman when I get through with you.” She elbowed me.
“I’m thinking I hope the lessons never end.”
Marion laughed. We looked at each other. A moment of comfortable silence.
I said, “Why me?”
“Why not you?”
“I dunno. You’re older. You’re gorgeous. You could have any man you want. I mean, some of those guys in the office, the contractors and vendors…”
“What do you mean?”
“I mean, look at me. I’m a skinny geek. You’re way out of my league. I’m just a nobody in the office.”
“Don’t sell yourself short,” Marion said. “Your code is starting to drive the train. You’re taking the original stuff to a whole ‘nother level.”
“Really?” I said, not sure I believed her, though I had received good praise.
“I’m management, remember? I hear things.”
I smiled at her. “Cool.”
I was quiet for a minute, then, “But why me out of all the other guys?”
“Well, for one thing I like the way you move, baby, fluid, delicate, sensual. I like the way you look when you’re at your computer, the way you tuck your hair behind an ear, or blow a strand out of the way when you’re concentrating. I like that you have your ears pierced. I like what you have to say in meetings. Plus, I think you’re beautiful.”
“Look it up sometime. It means more than a woman’s pretty looks, but your looks are pretty.” She winked at me. “Yeah, I’m not so much attracted to hairy, testosterone fueled, aggressive, he-man types.
“Oh, there’s a time and place for everything, baby, and I’ve brought a few neanderthals to their knees in my time, but you got under my skin a bit. And I began to want you skin to skin. So… I hit on you. I do hope you don’t mind,” she said and snuggled up against me, her soft skin warm and yielding.
I smiled and snaked my arm around her.
“The dream was real, by the way. But nowhere near as good as this.” I kissed her in response.
Marion stroked my chest, fingered the camisole I wore. I plucked it and said, “This?”
“Care to, I dunno, elaborate?”
“It’s one of my kinks.”
“One of your kinks?”
Mmm hmm. I’m a kinky girl, baby. If I keep you around long enough you just might wear some kinky boots too.”
“Mmm, I love lingerie. The look, the feel, oh god, everything about it. I love a man in lingerie, especially men who are not he-men. Men like you,” she said and poked my chest with her finger. She stroked my cock with her knee and said, “I nearly came when you let me put this gorgeous camisole on you. God, I gushed. Could you feel it? You look so hot in it!”
“If you say so.”
“Oh, I do, baby, I do. Does it shock you? I hope you’ll play along with me. You won’t disappoint me, will you?” She stroked my cheek.
“I’ll, uh, try not to.”
“That’s a good boy,” she said and kissed me tenderly.
In the shower Marion paid special attention to my rear. Face to face, our bodies pressed against one another, she slid soapy hands between my cheeks. A finger pressed lightly into me and I moaned into her hair. In my ear, “Do you like it? Do you like my finger in you? Do you, baby?”
You might want to read the earlier chapters for a semblance of context. On the other hand, you know what you’re in for here. I hope you enjoy the kink, baby.
“I have a friend who wants to suck your cock, baby.”
Marion said this to me late one Thursday night as we lay in bed, preparing to go to sleep. I wore a darling amethyst colored Canterbury knot nightie that had spaghetti straps and eyelet lace top and bottom, and Marion wore a black with white polka dots satin boxer pajama set.
I rolled to my side to face her, tucked my thick, silky, shoulder length sandy blond hair with highlights behind and ear with a manicured finger and said, “Say what?”
“You heard me. I told a friend about you, about your marvelous cock and he wants to suck it.”
“Some guy wants to suck my cock.”
“That’s right, baby. He’s a gay friend and I showed him your picture and told him what a fine sword you have and he wants to suck your cock.”
“Really. Well, maybe I egged him on a bit. And, truth be told, I want him to. I want to watch him put his lips around your beautiful penis and suck you while you sit there and enjoy the pleasure he gives you.”
My heart beat faster. “You do.”
“Oh, yes. I really do. He’s coming over tomorrow night so get some good sleep. I’d hate for you to embarrass me by not being able to have at least a little staying power because you’re tired.” Marion pecked my lips and rolled over. She backed into me and wriggled her bottom against me and I put an arm around her and spooned her.
My cock twitched and thoughts drifted through my mind. The surprising journey I was on, the journey that Marion led. I would never have imagined it in my wildest of dreams or fantasies. But it happened, is happening, and to my amazement, I went along and enjoy it.
I had a few bisexual experiences back in college and grad school; let a guy suck me, fucked him a couple of times too, then a couple of really drunk hook ups, don’t remember much about those. In fact, other than letting the guy suck me all my male experiences were alcohol fueled.
After grad school I got a job where Marion worked and there were sparks despite our age differences, her being in her late twenties and me in my early twenties. Apparently, Marion saw something in me, liked it and exploited it in the service of her kinks. In return, I got Marion and her, our, kinks. Well, it’s not entirely that simple, of course. But as it turns out I am way more submissive and compliant than I ever thought, and she dominant. Plus the other personal dynamics shaped by our personal histories and cravings and longings and relationships. All that allowed me to let Marion lead the way and for me to willingly follow. I trusted her and loved her with all my heart.
We now live together in her two-story high rise condo overlooking a wide, deep river. And when at home, which is two or three days a week lately since it was arranged for me to write a lot of code at home so I wouldn’t be distracted by all the office bullshit, I am dressed as a woman. A slender, toned, flat chested woman who is shockingly pretty.
I fell asleep thinking about the road ahead and about Marion, the love of my short life.
Friday. Marion did her makeup magic and I looked stunning, sensual and alluring. I tilted my head and cleared my hair and put in my dangly earrings, big silver hoops tonight, and put on a thick silver necklace with practiced ease. I gathered a cobalt blue stocking with manicured hands, my nails a rich taupe shade, pointed matching toee and pulled the gossamer fabric up my long, toned, hairless leg and my cock thickened. I repeated the act on my other leg and reveled in the feel of my hair, one and one-half inches below my shoulders at the ear, drifting over my face and shoulders, felt the tug of my earrings and the sway of the necklace and my cock thickened.
I put on a midnight blue lacy thong and snugged the extra thick strap tightly against my rear and my cock twitched.
I put on a precious microfiber, taupe colored flutter sleeve dress with an empire waist and deep cleavage. I liked the way it looked and flowed. I felt so pretty and feminine and desirable in it.
Steven arrived on time, after Marion and I cleaned up after a dinner, a delicious blackened salmon and a to die for side of a slice of mouthwatering fresh tomato, olive oil and feta cheese sprinkled on top. Mmm. We were well into the champagne when he knocked on the door and my stomach flip-flopped. He would be the first person besides Marion and a few delivery boys to see me dressed up.
Marion answered the door and ushered Steven into the living area. He was tall, a head taller than Marion even in her heels. About Marion’s age. Lean, fit, and ruggedly handsome would be the casting term to describe him.
Introductions were made and Steven said, “Wow, Marion, your lavish words didn’t do her justice. You are gorgeous!” he said, looking at me.
“Thank you,” I said and tucked my hair behind and ear and my bracelets tinkled and my heart raced.
“I’m really serious. You are. You could walk right down the street and guys would drool over you and no one would know. Unless you walk funny or something,” he joked.
I smiled and Marion said, “She’s got a great walk. Took to the heel to toe stride like a runway model.”
“I know this is awkward, weird even…”
“He knows about my kinks, baby. And I know his. Isn’t that right, Steven.”
“Yeah, Marion and I go back a ways. And, uh, I have a few kinks of my own…”
“I told him about your magnificent cock and Steven’s eyes lit up and I knew his mouth was watering for you.”
“Marion!” Steve blushed.
“So, anyway, I offered you up. I hope you don’t mind, baby, but I want to see him suck your cock.”
I shrugged my shoulders slightly. I would probably do anything for Marion.
“I want to see him on his knees before you, with your cock in his mouth. He’ll even swallow your cum, won’t you Steven.” She looked at Steven, paused a moment and when he didn’t respond said, “Answer me.”
Steven nodded and she said, “That’s a good boy. Come,” she held out a hand to him and the other to me. Marion led us to the buttery soft, brown leather couch and gestured for me to sit.
“While we’re at this, Steven, we might as well have a little CFNM fun for old time’s sake. Hmm?”
“What’s that?” I said.
“Clothed female, nude male. Steven here likes a bit of power exchange play, don’t you, Stevie.” He blushed again and nodded. “You may disrobe.”
Steven took off his Tommy Bahama silk shirt, kicked off his running shoes and socks. He unbuttoned his cargo shorts, unzipped them, pushed them down with his underwear, stepped out of them and stood before us naked.
Marion slowly circled him, appraised him and his cock thickened. “Steven, Steven, Steven. Gone a little soft, have we?” She poked his stomach and waist with a manicured nail. “Last time I saw you you were pretty ripped. But look at you now, you’re practically a flabby blob.” Steven reddened slightly.
I didn’t know what she was talking about. He looked in fabulous shape to me.
Marion stood beside him, turned toward him as he faced me. She hefted his cock and balls with her hand and he grew harder. “Well, at least this hasn’t shriveled up. Good thing you like men because I doubt this could ever really please a woman.” Steven flushed.
I didn’t know what she was talking about. It looked like a perfectly normal penis, in fact, it was about as big as mine, maybe a tad longer, a tad thinner, thick enough.
“Time to do what you do best, Steven. On your knees.” Steven started to take a step toward me and Marion said, “Aren’t you forgetting something?” Steven dropped to his knees and started to crawl to me and Marion said, “Oh my, have we forgotten so soon? This is shocking. Why I think I just might need to punish you so you’ll remember your manners without reminder.”
Steven turned to Marion, lowered his head and kissed her shoe, her gleaming black five inch strappy high heel shoe. A slight move of her weight and he kissed the other one. “She released him with, “That’s a good flabby naked boy, now go suck some cock while I sit over there and watch you please my man.”
I wondered exactly what their history was. Steven kneeled before me, reached under my dress, found the hem of my thong and pulled. And in a move I’ve come to love, a move that makes my pulse race a little faster and my cock thicken, I lifted my rear and Steven cleared my thong and it was off and I was hard.
Steven pushed my dress up. He smiled at me, looked into my eyes and took my cock into his mouth and I moaned. A handsome man sucked my cock and I watched his head bob between my stockinged thighs and his mouth and tongue and hands were practiced and wonderful.
Steven savored my cock, brought me to the edge several times before retreating. I’m sure my moans pleased him and he finally, finally, finally let me come into his sweet mouth.
I sat there panting. Marion said, “Nicely done, Steven. Was it as good as you dreamed?” Steven stood and nodded. His cock was hard. She looked at me. “You’re staring at Steven’s cock. Go ahead, baby, it’s a free country.” She smiled and I blushed. “You may get dressed Steven. Will you be available evenings this week?”
“Yes,” he said, dressing.
“Good. I’d like you here each night.”
“For more of the same?”
Marion smiled and said, “Mmm hmm. For more tasty fun.”
Steven smiled, went to her and kissed her offered cheek, did the same to me, said thanks and goodbye and Marion saw him to the door.
Marion led me up the black wrought iron spiral staircase, past the locked door, into our bedroom and fucked me hard with her strapon, fucked me until she cried out and came.
Marion spooned me as we were falling asleep and I asked, “How do you know Steven? You’ve obviously done some sort of scene together.” I wasn’t jealous, the past was the past and he’d just sucked my cock at her insistence and I knew Marion loved me as much as I loved her.
“Not in the way you think. He doesn’t like to have sex with women, but he does like women to, oh, I guess, dominate would be the right word. He definitely likes women to dominate him.”
“And you did that?”
“Mmm hmm. It was fun.”
“Like you do with me?”
“Oh no, baby, it was much different.”
“Go to sleep, baby. We’ll talk about it later.” She kissed the back of my head.
As I did for the following week, I fell asleep wondering if Steven was going to be the one, if that’s what Marion had in mind, and how soon if he was going to be the one.
Steven came over every night and gave me a blowjob. Sometimes Marion taunted him, sometimes not. Sometimes on the couch, sometimes in the bedroom. He was handsome. My lingerie was always divine.
Friday night. I looked beautiful. I felt beautiful. My hair brushed sensuously across my shoulders, and my dangly earrings tugged and swayed and I felt lovely and feminine and ever so desirable as I put on the long sleeve, medium square, crotchless fishnet body stocking and high heels with a strap. Marion said it was often necessary for a woman to wear high heels with straps so they wouldn’t fall off when she was getting fucked. She put a beaded choker necklace on me.
It was very late when the doorbell rang, Marion answered and ushered Steven into the bedroom. Marion and I were quite tipsy from champagne.
Naked, kneeling between my legs he smiled and said, “It still knocks me out how pretty you are.” He took my face in the palms of his hands and kissed me tenderly. I felt his tongue seek entry and I opened my lips and kissed a man and my heart raced and my stomach fluttered I knew it was coming and I was scared and excited and nervous.
Steven kissed me then worked his way down my neck, to my chest, licked, sucked and bit my nipples. He worked his way down, kissing flesh, biting squares of exposed flesh between the netting, he cupped my package then peeled off my thong and it looked sexy, the hem of the crothless fishnet body stoking rising to just above my cock and back down. Steven stroked my hairless balls and took my cock into his soft, hot mouth and sucked me and loved me until I came. He stayed on me and his tongue swirled and he loved me until I was once again rock hard.
Marion urged me to the bed, urged me lay on top of her. She was so wet and I slid in so easily and I moaned and I kissed her and she purred. She wore sheer black thigh highs, pointy high heels, earrings, a necklace and an ankle bracelet. I moved slowly in her. It was an odd feeling to be having sex with my beloved Marion with someone else in the room.
I felt the bed shift and my heart thundered and I saw Marion’s manicured hand close around Steven’s cock and I saw her stroke his hard cock, so close to me, so close to my red lips. She stroked his cock and took him between her soft red lips, into her soft wet mouth and I moaned and moved slowly in her and she sucked him. She stroked his cock and I felt her hand on the back of my head and heard her softly say, “It’s time, baby, time to repay Steven for the pleasure he’s given you. Time to take the next step.”
Gentle pressure from her hand, almost imperceptible, as if her hand only followed my willing head as my mouth opened and my red lips closed around a man’s cock. A flesh and blood cock throbbed in my mouth and I tasted precum and I moved my tongue on him and sucked his cock and heard Marion whisper, “That’s my good girl.”
My heart raced and my stomach did somersaults as I felt wet fingers on my rear, penetrating me, and I groaned and moaned around the hot, hard flesh and blood cock in my mouth and I sucked the man’s cock while my earrings swayed and then the man’s cock was gone and my mouth was empty and the bed shifted and Marion said, “I love you, baby. I want you to have all the pleasure in the world.” Hands spread my legs, my cheeks. “I want this. And deep down, I know you do too. So take his cock, baby, open up and take it deep inside of you and see how beautiful it feels, how wonderful, so different from my strapon, you’ll see.”
Marion ground her hips against me. I felt that familiar blunt pressure pushing, insistent, relentless, and I felt my divinely sensitive rings slowly part, slowly spread before that hungry cock and I opened and he was in me and he filled me and I moaned and said, my lips at Marion’s ear, “Oh god, Marion, he’s in me, he’s inside of me.” I could feel her supportive smile as she caressed me and the handsome man behind me started to fuck me.
So big, so hot, so hard and soft at the same time, Steven filled me and fucked me and drove me into Marion and it did feel wonderful and beautiful and my emotions were reeling and I pushed back against Steven and his thick hard cock and I thrust forward into Marion and lay on her and kissed her, again and again and again until I heard Steven moan and crash into me and I felt him come and I clenched and came with a man’s cock in my ass. I came inside of my beautiful Marion and heard her sigh and we slowed and stopped and disengaged and as odd as it seems, as late as it was, we sighed and purred contentedly and simply fell asleep.
In the morning, not much after dawn by the light leaking in the window overlooking the boulevard and wide, deep river beyond, I woke to pressure at my rear. I drifted awake as Steven’s thick, hard cock pushed and pressed into me. Immense pressure, pushing, spreading, seeking and my rings slowly parted and I stifled a moan as he penetrated me and made my sensitive nerves sing. His arm crossed over my chest and grasped my shoulder and that big ruggedly handsome man’s rocked into me and oh god how good it felt, so good, so good, so full of thick cock.
He fucked me gently with long, deep, tantalizing strokes, almost all the way out, all the way in and it was glorious when he passed and pressed my prostate, my pleasure center. Marion lay on her side facing me. She woke to the gentle rocking, a smile slowly forming on her beautiful, lazy morning face, her raven hair in disarray. “He’s fucking you, isn’t he,” she said, her voice morning thick. I nodded and pushed back against Steven as his magnificent cock sawed in and out of me. “I’m not surprised. He once told me he really likes morning sex.”
Steven rolled to his back and pulled me onto his chest and drove his cock deep into my ass, my legs spread, my head lay against his shoulder, he thrust into me and I moaned. Steven fucked me faster, harder and Marion rose to her knees and took my hard, leaking cock into her soft, hot mouth and I moaned.
Getting fucked, getting sucked, I was delirious with pleasure and groaned and grunted as I let them take me in my wide square fishnet body stocking and high heels, oh my god, they were still on.
Steven fucked me and Marion sucked me and I came in her mouth and she raised her face to mine and I kissed her and took my cum and Steven jackhammered me and roared and came deep inside of me, he came deep into my ass and I kissed Marion and felt him slip away, leaving me empty and throbbing and, god help me, wanting.
We rolled apart, caught our breath and I said, “Whew, now I’d say that’s a hell of a wake-up call,” and we laughed.
Marion cupped my cheek, turned me to her and looked into my eyes and said, “I’m so happy you enjoyed it. I’m so proud of you, baby.” I smiled back and our eyes conveyed our deepest love.
I took off my high heels and earrings and necklace and body stocking. We all did our business then stepped into the large shower together. I never tire of seeing Marion’s lithe, toned body and perfect breasts, and she lovingly appraised my toned, slender hairless body and androgynous face.
We all took turns washing one another and Steven didn’t seem to mind helping wash Marion, didn’t mind touching a woman, though he paid special attention to me. Makeup was scrubbed off of Marion and me and she looked beautiful and Steven said I did too.
Under the cascading water Marion pushed gently on my shoulder, pushed me gently down and I did as she wanted and let her push me to my knees on the white tile floor, water flowing around me, my wet hair slicked back, and I took a man’s cock into my mouth. I sucked Steven’s cock and my stomach had butterflies at its full feel and I ran my tongue and hand around and up and down and around as Marion had so often done to me, as Steven had done to me, as the football player in college had done to me. I sucked his cock and a peace welled up inside of me, a growing acceptance, a sense of gratitude and I loved Marion for her insight, I loved her with all my heart and through the roar in my ears I heard her say, “That’s my good girl.”
I sucked his cock and my wet hair snapped across my shoulders and he pulled me up and turned me around and I faced Marion sitting on the bench. I leaned and put my hands on the wall with my rear out and up and I moaned as Steven’s thick, hard cock speared me and possessed me, his hands on my hips as hot water rained down and steam encircled us in a swirling sensual cloud.
Marion kissed me and stroked my cock and roughly, mercilessly tormented my nipples and Steven fucked me and I moaned and he fucked me faster and harder and I heard him cry out and Marion leaned in and I came in her mouth and Steven came in my ass, so very deep in my ass and I clenched around him and he moaned.
They broke me in that weekend, oh god, Marion and Steven broke me in, they truly did. Marion had me changing into a new set of lingerie or outfit after each round of sex and I must have changed dozens of times over the course of two days, all manner of panties and fabrics and stockings and colors and dresses and earrings and bracelets and necklaces. It was a glorious orgy of fashion and sex and I opened myself and embraced it, I fully embraced it, I truly did.
This story is completely true. I hope you enjoy it because I have been dying to write it for almost 4 years now!
Hi, my name is Ashley. At the time of writing this story I am a 24 year old crossdresser living full time as a woman. It wasn’t always like this however…so let me tell you about how it all began.
Chapter 1: The beginning, and going out.
Flash back 10 years when I had just turned 18 years old and had just been accepted into the University of Vermont. I was ecstatic because this was my reach school (I wasn’t all that smart book wise) and it was the school that my sister Elizabeth (20, a junior) was already attending.
My sister and I were as close as you can get sibling wise. She was always there for me during high school and would always help me out when kids at school would pick on me. I wasn’t the biggest kid…I was only 5′ 5″ and weighed about 135 pounds. I had also never really quite hit puberty and didn’t grow much hair on my body, especially in my face. I was also into heavy grunge music and wanted to emulate some of that 90′s look with kind of longish hair that fell to shoulder length. (brunette).
This caused me to become kind of introverted. I didn’t really have many friends, and because of that, it caused my sister to take me under her wing so to speak. She was beautiful. She was the exact same size as me. Actually, her body looked a lot like mine except that she had size C breasts and blonde hair. She was a very popular girl when we were in high school. She had a lot of boyfriends and was a cheerleader in high school and at Vermont. She also has a killer butt, which we both share, as well as hips…(something that was always very awkward for me as a boy).
Being so close, we did a lot of things together. She also had really cool friends in high school which would always accept me into their hang outs at home and stuff. They would talk about all sorts of girly things…boys, shopping, school, and even sex. This had an affect on me throughout my entire life.
You see…my sister didn’t know this, but when she would go out with her friends I would try on all sorts of her clothing. My favorite and first parts of her clothing were her underwear. From a very young age (12) I had put on her panties and would wear them under my clothes whenever I had the chance. When she got older she kept getting sexier and sexier undergarments, and I would keep evolving into wearing more and more of her clothing. Not just the underwear, but the bras, the shirts, the pants, the dresses, and the heels. I eventually would start wearing her make up too.
But back to the story! So I had just moved into U of V. I had gotten a single dorm like I had requested and had unpacked everything and set up my room. My parents had put everything away for me and helped set up my room and were now leaving. I had brought a special bag with just a few pairs of my sister’s thongs that I tucked away under my bed without them noticing. When they left, we had some stupid meeting with our Resident Assistant in the hallway where we had to say our names and stuff.
After the meeting, my neighbor to the right of me came in and greeted me. His name was Paul. He was huge! He stood at about 6’4″ and had muscles everywhere. He told me that he played for the hockey team and that he was actually 20 because he had gone to prep school for hockey but was also a freshman. I said hi to him and we talked for a bit but realized that we didn’t have much in common so he left.
Finally! I thought to myself as I went under my bed to grab the bag of underwear I had stowed there. I was in such a rush that I had forgot to lock the door as I went into the bag and grabbed one of my favorite thongs. I had stolen so many of my sister’s underwear by this time I had no clue how she had not noticed. It was a pink and black thong with ruffles along the top and a tie string in the back above the butt. The front had pink flowers and was made of a sort of stretchy mesh material that was see through. I pulled down my shorts and boxers and slid it up my legs. I was a heavy masterbater, and it made my balls very small…which went well with my penis size which was roughly a solid 4″ when hard. Because of this I never tucked, and just kept my soft penis and balls in the encasing of the thong.
I looked back at myself in the full length mirror on the door and admired my ass. At this time in my life I had never considered my sexual orientation. I would masturbate to all sorts of pornography. Shemale, crossdresser, straight, gay, whichever i was feeling at the time. But I had no inclination towards any gender. I just liked looking like a girl, and would envy girls daily. I had shaved before leaving for school and was completely hairless except for my head and eyebrows. I was also a heavy pre-cummer, and some was already leaking into the thong just looking at my wonderful full bubble butt.
Just then, the door knob started turning and I was frozen with fear…Who could this be? Not an RA please! Not my parents! Not Paul!
It was neither…In the door frame stood my sister…holding a case of beer. For a second we just started at each other. My head turned over my shoulder at her, with my ass in clear view encased in her black and pink thong. Her standing there with the 30 rack in a skirt, black tights, tan boots, and a white sweatshirt.
Then we both moved at once. I turned around and covered my self up while she hurried in and closed the door.
“I…I can explain!” I tried to get out.
“ALEX!” she screamed, then quietly “What the hell are you wearing! Are those my panties?!”
“Y…yes…” I started crying “I’m so…so sorry!” I put my head into my hands and cried.
“Little brother, don’t be sorry. You honestly don’t think that I didn’t notice that every time I bought new underwear they were stretched in the crotch? That they would go missing for weeks at a time just to magically appear washed and in my dresser drawer again?”
“You mean…you’ve known this whole time?” I asked through sobs.
“Of course I have! I’ve been waiting ages for you to tell me! Are you gay? Do you like boys? Why do you do it?!”
So we started talking. I told her all about it. How I had the figure of a teenage girl. How I was always so envious of her life. How I was constantly picked on and just wanted to look just like her and hang out with her and her friends because my life sucked.
“You know what little bro, I think that I can help you out with something if you want to go along with it….”
“What do you mean?”
“Well…you see I haven’t really told my friends that my sibling was coming to this school yet. You haven’t always been really sociable with people, and I just didn’t want to mess anything up with them. I had trouble making friends here, and I didn’t want to show them my kid brother who doesn’t like talking to anyone. But now that I know why you were like this…I want to help you out.”
“What do you say…you become my sister?”
“How would that work! I have to take classes as Alex! I got accepted here as a boy!”
“Oh I know, don’t worry about that. You can take all of your classes as a boy, but when you come hang out with me, and my friends, you will be my sister. Ashley.”
“I…I don’t know, it seems kind of risky.”
“Nonsense. Come to my apartment tonight. And wear those panties hehe.”
For the rest of the day I was extremely nervous/excited. I wasted time by watching TV and playing some video games in my dorm until the clock rolled around to 6pm and I made my way over to her apartment. I was wearing the black and pink thong like she requested underneath my jeans.
I rang the buzzer and she buzzed me in and told me to come up. I got up the stairs and knocked on her door. She let me in. Her apartment was a single like mine. It was a large studio type apartment. It had a kitchen and a living room and a bed all in the same big room. It also had a bathroom and a closet attached to it next to the bed.
“How’s my little bro…sister!? Nervous?!”
“You have no idea…”
“Don’t be, this is going to be a great night! We are going to go out to a party with some of my friends. It gets pretty wild here on the first night of the semester.”
“Yipee…” I said unenthusiastically.
My sister was already dressed. She had a short purple dress on. It had ruffles at the hem of the dress, and was tight to her body. Her hair was up in a type of loose bun, and her make up and nails were also a light shade of purple. Her heels were black, and were huge. She liked to wear big heels. They were about 4″ big with a 1″ platform. She looked hot!
“Stop looking at me like that weirdo! You’re creeping me out. You are going to look just like this…but hotter! All the boys are going to want to get with you tonight!” She laughed at me with a wink.
“I don’t want that! I just want to have some fun for a few hours with you and your friends and sleep here and go home!”
“Ha! Not if I get lucky tonight you aren’t sis…you will be going back to your room!”
“Ew!!! Please don’t talk about your boyfriends in front of me.”
“Come on sis, all girls talk about their boys. Even one night stands. Now come on, let’s get you ready. Strip!”
I took off my pants and shirt and stood there in the black and pink thong…already leaking pre-cum in anticipation. I instinctively lowered my hands to cover my small bulge.
“No need sis, we will both be seeing each other getting ready from now on, so it’s only a matter of time. Plus your small penis is cute…it’s perfect for a girl…who has a penis,” she laughed again.
I was beat red but did as she said. I stood there awkwardly with my hands to the side as my sister looked over my body.
“Well it looks like my sister knows how to shave herself…let’s get to work on your nails and make up.”
I showered and returned to her with a towel on my hair and the pink and black thong on. She had me sit down at the table and she got out some nail polish. She painted my fingernails first. A bright shade of pink. Than she went to my toenails. She did a french pedicure, and they looked sexy…precum was leaking into my panties once again….Next she moved to my face, where she went to work with all sorts of make up that I had no clue what was going on. She blow dried my hair and than straightened it and curled it into some wavy curls that hung by the side of my face.
She then got out some tweezers and worked on my eyebrows. I knew now that everything that she had just done could be reversed, but shaping my eyebrows was permanent. I was really in for the long haul…
When that was all done she had me get up and go over to her closet. She got out a black bra that had lace on the cups. From there she opened up a box of breast forms (“Bought these for this occasion today hehe”) and put them in the cups, giving me a real feel on my chest.
Next she pulled out a black dress. Much like her own in that it was short. I pulled it over my head. It came down to about mid thigh, barely covering my butt. It had ruffles on the sleeves, and a very revealing bust line.
Than she pulled out a pair of pink heels. They were 4″ with a 1″ platform, just like her own, and had a bow in the back, just above the heel.
“Holy shit sis!” Liz squeeled, “You look hotter than all of my friends!”
She turned me around and faced me to the full length mirror on her bathroom door. What I saw completely shocked me. It wasn’t me anymore…it was a hot freshman college girl, standing there looking completely shocked. My make up and freckles were perfect. I had a light shade of pink that matched my nails and heels. My lips were painted with a bright pink lip gloss.
I twirled around. My ass was amazing. Like super-model amazing. The heels had pushed it back and up, and it was framed perfectly by the dress. I was getting hard, and precum was leaking, no, flowing into my panties now as I became rock hard.
“I…I don’t know what to say…thanks Liz…” I said in astonishment.
“Don’t thank me, you look amazing! Now let’s practice some walking, and work on that voice of yours!”
So I started walking around the room working on practicing to move my hips and my voice to become slightly higher pitched.
I got it down in no time, and we were ready to go! We walked into the cool autumn air, and were heading to pick up 3 of Liz’s friends and head to the party.
“So where are we going tonight?” I asked in my new girlish voice nervously.
“To the hockey house of course, that is where the biggest and best parties are thrown here at UVM. They have the hottest guys there too…you’re going to LOVE it!”
“Liz, I told you I don’t want to get with guys! I am straight, I just like the clothes girls wear…”
“Ok sis, suit yourself, but good luck fending off the guys tonight!”
So we got to my sister’s friend’s apartment and went upstairs to get the other 3 girls. Amanda, Kristen, and Sara were their names, and they looked just about as hot as we did. They were all wearing the same sorts of clothes we were, with slutty heels, and short dressed. We exchanged hellos, and I was very nervous saying hi and getting introduced as my sister’s sister. It was weird…
We started to take some shots to “pregame” the party and I started to get more and more buzzed. This was my first time drinking, and I was loving the feeling. All my anti-social behavior that I was used to was going away, and I was talking and acting as girlish as possible. I was doing a good job too, because her friends were loving me. They kept saying how they were so excited to have a new friend come to the parties with us and loved that I was so fun.
So after we took about 4 shots each we all got ready and started to walk to the hockey house. My feet were killing me, being the first time I was ever wearing heels, let alone monstrous ones like these.
We approached the house, and from the outside I could already tell this was the place to be. It was so loud from the outside and there were a bunch of people already outside and noticeably drunk. People were playing dizzy bat and beer pong, and most of them were older, looking like Juniors and Seniors.
My nerves started to come back to me, and I was extremely nervous that someone would notice that I was a guy. But that quickly went away as we entered the house and 3 guys migrated towards us and started some conversation.
My sister deflected their comments and moved us deeper into the house.
“Hey Ryan!” Liz shouted over the music to a guy about 6’1″ With huge muscles and black hair.
“Liz! I’m so glad you came! And who is this?!” The guy said as he tilted his head towards me.
“This is my sister, Ashley! She is a freshmen, and this is her first time out, and first time drunk too hehe.”
“Well Ashley, nice to meet you…I hope you have fun tonight. There are some freshmen kids here on our team. They are already pretty trashed though considering we had our hockey initiation tonight.”
Just then to my left a hulking guy came over and through his arm around me and my sister. I looked up and then my face went white with terror. There stood Paul, one arm around my neck, the other around my sister’s.
“What up Paul,” said Ryan “looks like we have a new girl for you to meet…Paul meet Ashley. Ashley, Paul.
“Hey sexy,” he breathed on me with an intense smell of alcohol, while also pinching my ass.
“Hey,” I said in my quietest girlish voice…
But that pinch did something to me. Maybe it was the alcohol. Maybe it was just my own feelings towards guys…but I got rock hard in my panties. It was like a turning point in my own head…something just…went off.
My sister looked down and noticed the tiny bulge, instantly grabbed me and pulled me to the side.
“Sis, relax. Looks like someone does want to be hit on boys tonight! Ryan is this kid I had been with last year. We were kind of…fuck buddies. All the hockey kids are extremely built, and the best lays on campus…but are really rough. I don’t want you to do something you don’t want to get messed up in, or hurt.”
“Liz, I’ll be fine!” I giggled at her, “I just want to have some fun!”
“Ok…but be careful,” She said worried.
With that I sexily walked over to Paul, and grabbed his hand.
“Do you have some more alcohol?” I asked sheepishly.
“Yes…yes I do, come up to Ryan’s room, that is where my beers are,” he slurred back to me.
So he took me by the hand and led me upstairs, with the sounds of woooo coming from his friends. He led me up into Ryan’s room and shut the door behind him. He went behind his desk and grabbed 4 beers, and a funnel.
“You ever done this before?” He asked me.
“Well come on, it’s easy.”
He poured 2 beers into the funnel and stopped it at the nozzle. When all the foam was cleared away he said, “Get on your knees, and put this end in your mouth.”
So I knelt down on the floor, my sexy bubble butt resting against the spiked heels and put the nozzle in my mouth. The beer came flooding into my mouth and I managed to swallow it all.
“Mmmm, that looked hot,” Said Paul.
“What?” I said taken aback.
“You just looked hot…sucking on that hose…” Paul said, stroking the unmistakable outline of a giant penis in his jeans.
I don’t know what came over me, I was extremely hard and leaking precum again, as I moved towards Paul, looked up and kissed him on the lips! The strong smell of beer and other alcohol invaded my mouth as well as his tongue. I had never been kissed before, and it was so weird that it was a guy! He was rough, and sloppy. I was just letting him force his way into my mouth as much as he could get to.
As we were making out, he was moving his hands down to my ass and rubbing and grabbing it. Pulling my cheeks apart and smacking it from time to time. I was so horny, but staying far enough away from him that my own penis would not rub his gigantic one. I started to move my hand over it. It must of been at least 8″ and very thick…then he broke our make out session.
“I’m very drunk Ashley…I don’t want to do something you don’t want to do, I can’t risk being kicked off the hockey team if you thought I was raping you or anything.”
“Shhh, just keep going, you’re not doing anything wrong…I’m so wet…”
And I was…i was leaking precum so much into my panties it had to be leaking onto the floor by now…
“Ok cool, then bend over.” he said abruptly.
I was so nervous now…he couldn’t know my secret! Thinking fast the first thing I said was “I’m on my period!”
“Oh thats cool, we will do it in the ass then…are you cool with that?”
“Do I have a choice?” I winked at him. “It will be my first time though…”
“Mine too…but don’t tell the guys, they think I’m a ladies man haha”
With that I spun around, walked over to the couch moving my hips seductively, and laid over the couch arm with my ass in the air, making sure to squish my bulge into the arm to not let it be seen.
Paul moved behind me, already taking off his pants and lining up his cock with my waiting hole. He hooked his finger into my thong, and pulled it over to the side. “Mmmm you have such a tight little hole and a great ass Ashley.”
“Thanks hehe! Hurry up I’m so horny! But go slow!” I said not really making sense in lust and drunkedness.
Paul put his finger into his mouth and sucked on it. He added one finger to my hole, and then a second quickly followed. It hurt at first, but he was slow and gentle, moving eventually three fingers into my waiting hole and pumping in and out slowly. Girly little moans escaped my mouth as his fingers fucked my virgin boy pussy.
“Are you ready Ashley?”
“Yes…sexy,” I said in between moans.
Paul pulled his fingers from my hole and moved his huge penis head to my waiting now slightly loosened hole. He then pushed a tiny bit and I felt what felt like fire on the entrance to my ass. It felt like a mack truck was trying to enter my body, but slowly, inch by inch he worked his way in. Stopping every other inch and letting it rest there before all 8 huge inches was filling my insides.