Stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me!
After my debts began to mount, college fees and all that, one of my mates from Brum suggested I try to earn a little extra cash. I was surprised when he told me how. He said he’d done it and ended up with a couple of hundred extra most weeks, sometimes just for an evening’s work.
“It’s easy, James. You’re a handsome man, use what you’ve got.”
I’d had my doubts but I’d done it. I’d registered with an escort agency. My mate had lent me his dinner suit when, only a week after registering, the secretary there had rung me up.
“It’s a Mrs Kenyon, James. Very nice woman. In her fifties maybe, she’s used us before. I think she’ll like you, and you should enjoy the evening. She’s like you to escort her to the theatre. In Stratford. It’s the production of ‘Romeo and Juliet’, she’s got two tickets for the show.”
In no way should that production be referred to as a ‘show’. And this woman had two tickets, to the ‘must-see’ event of the year! My mind boggled. I could get to see the play, free for Pete’s sake, and get paid for it into the bargain. And all I had to do was escort some older woman to the theatre, play along at being her toy boy, something like that.
I’d been reassured by Victor that it would be just that – escort a woman to an evening out, dinner maybe or to the theatre.
‘Mostly older women’ he’d said. ‘Lonely, maybe divorced or widowed, willing to pay for the company of a younger guy for the evening.’
I had to admit the idea of being paid and getting a more-than-decent meal inside me appealed. And to see that play too, no way was I ever going to be able to get tickets myself. I’d asked him one more thing though.
“Oh no” he’d said. “Not this agency, it’s their policy. Like they say, ‘No sex please we’re British’. It’s just the company, and showing off the toy-boy of course.”
He’d grinned. I could go with that. I rang the agency the next morning to say ‘yes’.
“It’s Mrs Kenyon, James” said the girl from their office on the phone. “She’s used us before, she likes to use a different escort each time. She’s easily pleased, it seems, always gives the guys a good report and they seem to think well of her. She does seem to like younger men though, usually about half her age which fits you perfectly.”
“So she’s – hell – over fifty then?” I must have sounded doubtful.
“Yes, by a margin really. But an attractive woman by all reports. I’ve not met her, she always rings or writes. Don’t let that worry you though, really, it’s just one evening after all. And she pays of course. So – how about it, James? Have you a dress suit?”
I thought. No I hadn’t. But I knew Victor wasn’t actually ‘on duty’ that evening if you see what I mean. He was at a party with his girlfriend and wouldn’t be wearing his dress suit for that kind of party. And the money was an attraction.
They gave me instructions to meet Mrs. Kenyon in the lounge of a rather swish hotel in Stratford. I arrived at seven o’clock prompt, wearing Victor’s dinner suit and bow tie which fitted me pretty well, and made my way through the lobby of the hotel to the lounge. There were a few couples at tables and some business types discussing work over drinks. In the central area of the lounge, sitting on one of the plush settees, sat a middle aged lady pondering over a martini. On seeing me enter she turned and smiled as I strode towards her.
“Mrs. Kenyon? Good evening” I asked as I reached her.
“Please, call me Rita, and I’d like to call you James. It is James, isn’t it?” she asked.
I held out my hand to her, she shook it gently. She had probably spent quite some time in the beauty salon that afternoon I guessed, judging by her beautifully styled hair and her immaculate, though slightly heavy, make-up. I looked down at our hands together, especially at her elegantly-manicured and varnished long red nails.
“Pleased to meet you” I said, hopefully not sounding as embarrassed as I felt as I gently shook the hand of the woman I was to ‘date’. A woman quite some way older than my mother.
“The pleasure’s all mine” she retorted as she stood up and we kissed on the cheek. “Please, do sit down and join me. What can I get you to drink?”
“Scotch and soda” I replied.
She slid a note into my hand. OK, so I was the gentleman, I was to be seen to be paying. I could do that! A waiter took my order and hurried off to get it for me along with a replacement for Rita.
Rita turned out to be indeed some way over fifty. She was a mature woman with a rather voluptuous body which she obviously liked to emphasise. Her hair was clearly dyed, a deep auburn colour which I thought actually suited her. She was dressed in a rich purple silk blouse, which plunged almost indecently to reveal a splendid pair of very prominent and bulging breasts. Her tight black slightly-above-the-knee length skirt split up the side to reveal a sexy amount of leg encased in black nylon stockings and high-heeled black stilettos. Indeed a very attractive ‘older woman’.
The skirt was really much too short for a woman of her age though I had to admit it looked good on her. I had always rather liked the look of some kinds older women though I’d never actually been out with someone so much older than me, but she did seem very attractive.
“You look very handsome James, I’m very impressed with the agency’s taste,” she commented.
“Thank you, you look gorgeous yourself, Rita” I replied.
OK then, a bit of flattery but not too far-fetched I have to admit.
“Ah, but you’re paid to say that” she teased.
“Well, yes” I said staring her straight in the eye. “But only when it’s true.”
“So tell me about yourself, Rita” I asked after the waiter had brought our drinks.
And with that we broke into friendly conversation, getting on very well indeed, very quickly. She told me she was divorced, very well off from it, lived from London and was treating herself to a few days away from the city bustle in and around the Cotswolds. Time passed quickly as we chatted over our drinks, eventually having to hurry into the theatre.
We got to our seats just in time as the lights dimmed and during the first act her hand occasionally slid rather suggestively onto my knee, squeezing it occasionally as the drama on stage increased. After more drinks during the interval her hand returned and crept a little higher as she leaned towards me. We both thoroughly enjoyed the performance and retired to the theatre bar again for another drink once the play was finished. Her interest in me was rather flattering but it began to worry me a little.
“You looked like you really enjoyed the production, James,” Rita commented as we sat at the bar.
I couldn’t help noticing, sitting there with her legs crossed she was revealing quite some amount of very attractive thigh through the stretched split in her skirt. She noticed me looking, and smiled.
“Very much, it’s such a good production, one of the best I’ve seen.”
“I find it such a romantic play” she said. “It really turns me on.”
That definitely worried me! OK so she was a gorgeous woman, extremely attractive and she didn’t really look her age at all. But – it was what she’d said.
“Come on, James, my darling. I think it’s time we left. Can you accompany me back to my hotel?”
We left half our drinks and headed back through the moonlit evening towards her hotel. As we strolled, hand in hand, she paused once or twice under the streetlamps and turned towards me. I guessed she was enjoying showing off to the other patrons who were leaving, demonstrating that even though she was an older woman she could still pull a younger man. On the last occasion, just outside the hotel entrance, she began to stroke my hand affectionately and to whisper in a very teasing manner in my ear about how handsome she found me, and how she hoped I was attracted to her.
I was determined to do the job right. On the one hand I realised I had to please her and get a good report back to the agency, and my fee. But I really didn’t want to do what it seemed she was leading up to. I realised I had to make an impression though, to meet her half-way in a sense. And, much older though she was, Rita certainly was a fine figure of a woman.
So I reached my hand to hold her bum lightly, and then ventured as far as to run my hand down her leg and through the split in her skirt, just up to the top of her stockings. She was still tantalisingly nibbling in my ear as I did this, I felt obliged to slide my other hand round to caress her breast through her silky blouse.
“Oooooh, James, that is nice. I can’t wait to get you upstairs!” she whispered to me in a slightly husky, sexy voice.
She held tightly onto my hand as we walked in and through the hotel lobby. I admit the drink had got to me a little, but I was certainly enjoying the flattery to an extent.
I pressed the button for the 3rd floor in the lift and as soon as the doors were shut she hugged me, burying her lips in my neck. OK, so I’d gone so far but Rita’s intentions were clear. How was I going to get out of this without ending up with a poor report to the agency, and probably a reduced fee?
As the lift doors opened, Mrs Kenyon had to release me briefly to open her room door. I wanted to just give her a quick goodnight kiss on the cheek and make my exit, but clearly she wasn’t going to be satisfied with that.
“Do come in, James” she said.
Rita walked into the lounge and sat down on the settee, the split in her skirt opening up to reveal even more of her long, luscious sexy legs.
“Do take your jacket off, James my dear. Come and sit down.”
I wandered over and sat next to her.
“Mrs Kenyon. Rita, please, I need to explain.”
She leant over and began to kiss my neck which sent shivers through me. I have to admit I was quite considerably attracted to her and she was doing a very good job of seducing me. On the one hand I didn’t really want to kiss her. But on the other when she did touch her lips to mine and begin to caress my mouth with her tongue, pushing in gently to French kiss me, my resistance was rather feeble.
‘OK James’, I thought to myself, ‘One final heavy snog, enjoy this, then get out’.
I leaned over to forcefully push my own tongue between Rita’s luscious lips and again began to caress her breasts.
Her hands began to unbutton my shirt and pull it from my pants. She began to kiss my chest and slowly worked her way downwards as I actually enjoyed running my fingers through her silky hair. Her fingers crept to the belt and buckle on my trousers and began to undo them.
‘STOP!’ I thought.
“Er – Mrs Kenyon. You’re a gorgeous woman, really, I mean it, but ….”
She sat up and looked straight into my eyes.
“James, do you mean that?”
“I do, really Rita. It’s just that this is my first job with the agency and I don’t want …”
She interrupted me again.
“James. Look here.”
She began to unbutton her blouse, revealing even more of her cavernous cleavage. I just KNEW I’d have to get out, right there and then, this was becoming just too tempting.
“James, look at my pendant.”
I refocused on the gold locket as she held it just inches in front of her magnificent boobs. It glistened. It spun.
“Look at the locket, my dear. Look closely…”
Rita was speaking quietly, gently, carefully, slowly, oddly. Somehow it didn’t seem like a woman’s voice at all. I breathed in sharply.
“James my dear. Listen very carefully. I know you’re attracted to me and lust after me, that’s what this body is built for. To tease and please men. But, for the rest of the evening, don’t think of my age. Don’t think of me as old, just think of me as a woman. And whatever you see when we undress, well, you know what to expect so be sure that’s what you see. After all, looking like this, I must be built like any other woman, mustn’t I?”
Was it me saying that? Well, yes it was and no it wasn’t.
“And in the morning when I’ve gone, you’ll remember everything. Now, look at the pendant again, see it flickering, look closely….”
I juddered. I was staring at Mrs Kenyon’s breasts, at the most sensational pair of bulging tits I’d ever seen in my life.
“Rita, I just have to kiss you again!” I almost shouted, pulling her close and embarking on a very long, sensual kiss.
OK, so she was older than me, but what the hell! As we parted, breathless, Rita reached down to my waistband again and rapidly had my belt and buckle undone. Unzipping me slowly she then got off the settee and knelt in front of me. Her hands moved to the waistband of my trousers and pulled them down as I lifted my hips to help her remove them, and my shoes and socks. Now, clad only in my silk boxer shorts, she sat next to me again and slid her hand inside as our lips met yet again. We both moaned softly as she gripped my stiffening rod and began to rub it smoothly. It quickly grew to its full length and she let out an appreciative sigh as she fondled its full girth.
“My, James, I haven’t seen a cock quite so thick for such a long time. I hope it will fit!” she joked, teasing and caressing my rock-hard penis as she smiled joyfully at me.
She has a wonderful smile! My own hand slid down over her blouse and began to fondle her full breasts through the purple silk. Opening two of the buttons with one hand I slid my other hand inside and gently rubbed her nipples through her lacy bra. I moved her top to one side to free her breast and caress the soft flesh unhindered. Undoing the remaining buttons on her blouse I pulled it open to expose her chest, the nipples on her exposed breasts jutting out noticeably. I undid the central clip on the plunging purple bra she wore. I could still see that both nipples were deep red, and hard, and stiff.
“Fabulous” I murmured.
As her breasts swung free I took one of her nipples gently between my teeth and began to tease it with my tongue, much to Rita’s obvious delight, whilst I rubbed her other breast with my hand. We moved round so we lay next to each other on the settee and Rita continued to pull on my swollen penis as I moved one hand of mine down and began to rub her nylon clad leg.
Slowly I worked my way upwards above her knee, along the split in her skirt and up onto her thigh. Further still my hand travelled along the split to the top. I pushed it under the skirt and further up her leg. Our tongues continued to lock and our heavy breaths mingled all the while. My hand found the white of her thigh above her stocking tops.
“Mmm, very nice, Rita” I murmured as I caressed her stocking top and upper thigh with my hand.
“I thought you might like them. I think wearing stockings is so sexy” she said as I trailed my fingers along the line of her suspenders.
She lifted her leg and my hand moved round to the inside of her thighs and continued its journey. Pausing at the top of her thighs my hand circled her soft flesh and Rita gasped in anticipation.
“Don’t stop there, my darling” she urged sexily as I paused. “Let your fingers enjoy themselves.”
I let them travel further until they brushed her over her smooth purple thong. Rubbing gently I could feel her warmth through the material and pulled it to one side to explore further. She moaned loudly as I began to rub her long, stiff clitoris with my middle finger before probing inside her arse as her beautifully painted long fingernails began to wank me faster.
Pulling my hand away gently she looked questioningly at me. I just smiled and began to move down the settee. I moved in between her legs and ran my hands up to her thighs.
“Pull your skirt right up, Rita” I said and she did so without question.
Pulling her thong down she lifted her knees to help me get them off and still kept them together as I dropped them to one side. Placing one hand on each knee I gently prised her stocking-clad legs apart. She lay before me, her blouse open with breasts exposed, her skirt was up around her waist and her erect clitoris glistened and beckoned to me. It must have been at least eight inches long. Rita lay smiling gently at me with a look of pure sex in her eyes.
“Make me climax, James. It’s been a long time.”
“I have every intention of doing just that, Rita my darling, and more than just the once.”
My hands worked their way along her inner thighs once more and met at her hot erection. I pulled her balls down and bowed my head towards her. Poking my tongue out it touched her clit to lick the liquid beginning to ooze from her slit as she pulled me towards her.
Rita gasped slightly. “James, oh James, I’m going to cum!”
I swallowed her clitoris deep inside me and she groaned loudly as I sucked at her sweet, freely flowing juices. She began to grind her hips into my face as I continued to lick at her and clawed at her hair. Her whole body bucked uncontrollably as she pushed her groin against my face whilst crying out in sheer delight. I delighted in swallowing her love-juices, wondering why I’d not had such a beautiful and erotic experience with any of my previous girlfriends, then I moved up and lay beside her again.
“I know I said it had been a long time but I never thought anyone could make me come like that” she said breathlessly.
“Mrs Kenyon, I’m so pleased. And you’ve got the most gorgeous clit I’ve ever seen on a woman, I love it,” I said.
Her hand began to creep to my crotch again and slipped inside my boxers. After wilting slightly while I’d been sucking her clit, she soon rubbed me back to full length.
“My turn, darling” she murmured.
Rita rolled off the settee from where she lay and knelt on the floor next to me. Discarding her blouse totally she leant forward and pulled down my boxer shorts to expose my straining cock. Sliding my shorts off completely then, she took me in hand again and gently rolled back my foreskin to expose my knob. Slowly lowering her head, whilst smiling at me as she did so, she extended her tongue and touch the tip of my cock with the tip of her tongue.
Shivers ran through me as she made contact and then I was in heaven as she closed her soft wet glossy lips around it and began to suck me off. Her warm saliva ran down my shaft as her silken mouth caressed my yearning cock. I climaxed quickly and violently – I had to. No man can take treatment like that from such a sexy woman and not do so! Presently she stopped. I was done. Boy, was I done!
Taking my hand she stood up and I stood up to face her.
“Let’s go to the bedroom” she said ” I want you to screw me like I’ve never been screwed before.”
“It would be a pleasure, my darling.”
I led her through to the master bedroom and we stood by the huge bed. I unzipped her skirt and it fell to the floor. I was now completely naked and she just wore her stockings and suspenders.
“Would you like me to keep them on?” she asked.
“You look fantastic in them, and they feel wonderful. Ok, Rita my darling, onto the bed” I instructed.
She turned and lay on the bed.
“Open your legs wider.”
She was a sight to behold as I knelt down on the bed behind her and wrapped my lips round her still-wet clitoris again.
“Oooh” she gasped as I did so.
But this was just a temporary measure to make sure she was ready for me and soon I stopped. She pushed her hips back towards me in anticipation of what she was about to receive.
“Are you ready Rita” I teased, stretching out her anticipation as I moved towards her welcoming hole, erect cock in hand.
“God yes, stop doing this to me and get on with it” she pleaded.
I pressed the tip of my erection at the edge of her arse lips and ran it slowly up and down her groove.