I'D NOT LONG MOVED to a larger, three bedroom apartment when, one warm, humid Saturday afternoon, I finally got around to sorting out all of the various papers, books and magazines I'd accumulated over the last decade or so. Actually, I know it's something I should have done before I moved but I am one for keeping all sorts of things--you just never know when they're going to come in handy.
As I sat in front of the dining table, piled high with all sorts of papers and books, I flicked through the pages of the some dozen or so Transvestite, Transgender magazines and other publications I've written for over the last ten years or so--still, I must admit, enchanted by the pictures of myself either on the covers or accompanying the articles within--I began to wonder about some of the people, some of the clients (or customers), some of the 'punters', some of the irascible rogues I've met along my long journey to where I sit now. The usual reminisces really, about where are they now, what would they be doing, and would they even remember me? Can I even remember all or most of them?
I sat back in my chair and crossed my legs--feeling my tights swish against the lining of my skirt (a feeling that still evokes a pleasurably sensation no matter how many years I've been dressing up in female clothing)--then scratched around under my left bra strap, feeling my forearm caress the underside of my breasts as I did so. Hmm, another nice feeling, I thought. Feelings many 'real' women possibly never even notice, just take for granted. Yes, being a Tranny certainly has given me lots of memorable experiences along the way…still does if I am honest; experiences I could never have had if I was a 'normal' guy, with a 'normal' career and outlook on life. Hmm, pity I can't share some or all of them with other people.
For a few minutes I daydreamed about my recent and not so recent past, recalling some of the escapades and adventures I'd had; absentmindedly running my hands down my skirt on to my tights and tracing small patterns with my fingers on my thigh. Suddenly, I sat bolt upright, a rush of inspiration hitting me like the proverbial flash of lightning. I leaned forward, both elbows resting on the dining table and subconsciously 'puffed' out my cheeks, letting the air expel slowly as I thought; that's it! I am going to commit some of my experiences to print. I'm going to write a novella about them… Now where is my diary, my little 'black book'? Must be somewhere amongst all of these papers.
Although I must have written over sixty articles and short stories over the years--mainly for Transgender and Transvestite magazines or websites--initially, the thought of writing a story of sufficient length for publication as a book was daunting. It took me some time to put my thoughts in order and, for half an hour or so, I scratched around for an interesting enough synopsis.
I poured a drink of orange juice and stood looking out of the living room window for a while, admiring the blueness of the summer sky, until the ideas just started flooding into my brain.
Simple really, I thought, finally. Tell them all about what you are your life story. How you got to this point in your life. Sure to make a few people sit up and take notice. I smiled to myself as I studied the branches of the tree near the living room window and which swayed gently in the afternoon breeze. Maybe make more than a few people wonder if it's really them I'm writing about when they read my book. Give them a shock or two as well!
Now, once I get an idea, it usually consumes me--and this was no exception, consume me it did. Once I'd found my diary, for days on end I did nothing but write notes about my recollections and experiences, or should that be sexperiences--all of which are true and which really happened just about as I've described (but with names changed to protect the innocent or not so innocent as the case may be).
'I became a Transvestite Prostitute (without really knowing how I did so)' I slowly typed. Yes, that sounds a good enough title to me, I reflected as I sat in front of my laptop the day I decided to start writing in earnest. If I can find a publisher and the Editor wants to change the title that's up to them, but that's good enough for now. Anyway, here goes, the story of my life, well, the Transvestite part of my life--especially the last ten or so years. But where do I begin, there's so much to tell?
For a couple of minutes, I studied the nail varnish on my right hand, glanced across at my reflection in the wall mirror and then looked back at the keyboard, willing my brain to start deciding how to begin.
Well, it's been about two weeks since I personally had last met with a 'client', what with moving apartments and trying to sort out various matters relating to my updated business plan, I realised.
Plus, these days I was, far more selective of who I, euphemistically, slept with. Where did I go the last time I worked? I pondered, gently smacking the back on my right hand into the palm of my left. Ah, yes, Janice. Hmm, well maybe that's a good a place as any to start. Let me see…
I'd just finished having lunch on the concerned Wednesday afternoon when my mobile phone rang. Actually, it took me a few moments to realise it was my phone as the day before I'd upgraded to a newer model--one of those 'all singing, all dancing' dual purpose Blackberries which can be used as a phone as well.
"Hello, Samantha Wells speaking," I intoned in my best feminine voice. (I only ever took 'business calls' on this particular number and used a pseudonym when I did). 'How can I help?'
"Oh, hi," came a soft, slightly hesitant voice. "Er, Samantha?"
Yes, it is, I thought, having already said my name. "Yes, hi," I repeated, slightly surprised that the caller was a woman. "Samantha speaking."
"Hello, there. Yes, I saw your advertisement on the Web but now I'm on the phone, I'm not sure how to, er, explain things."
"No problem," I replied, sensing the nervousness in the woman's voice, and trying hard to place her accent. "Take your time."
"Well, thanks. I've never done anything like this before you see."
Maybe she's gay, I wondered, looking for a 'girlfriend' for the evening? After all, some women like 'chicks with dicks'.
"It's my husband's fiftieth birthday soon, you see," the woman suddenly blurted. "And I found out a few years ago he's a cross dresser. Loves to dress up and be a sexy woman now and then. So I thought if you could come around and keep him company for while on his birthday, well, that would be nice."
Aha, a frustrated CD, with a sympathetic wife. Maybe she doesn't quite understand but at least she's seems accepting of him. "Yes, would be happy to," I'd answered. "To whom am I speaking please?"
"My name's Janice. Can you come around on Saturday night?"
"Sure, no problem," I answered having first quickly checked my diary which I kept on my Blackberry. "Any preferences?"
"Preferences?" asked Janice.
"Oh, I mean for me to wear? And… er…" I began, realising it was my turn to be slightly embarrassed. Well she did say they've never done anything like this before. But sometimes, these sorts of clients are the most outrageous. "Does your husband want to participate in any particular activities?' I asked, phrasing my question as delicately as possible, keeping my tone warm and friendly. "Any special requests, anything I need to prepare for. Or does he want to just sit and have a chat?"
"Hmm, not sure about that," retorted Janice, hesitating again. "I just want it to be a nice surprise for him. Anyway, we can talk about it when you're here."
We finalised the arrangements and, after she had hung up, I mused whether she'd caught my real meaning about 'activities'. Maybe we'll just sit around and have some sandwiches and eat some cake, I thought rather facetiously. Oh, Samantha, don't be like that--everyone has to start somewhere!
Saturday night arrived before I knew it and, as I looked through the various drawers in my bedroom, picking up, looking at and then discarding things, I finally decided to wear the nice, new, white stockings and suspender belt I'd bought only the day earlier at one of the smaller, specialised underwear stores I frequented.
They go well with this white push-up bra and silk panty set one of my admirers gave me, I thought, as I slipped the rest of my underwear on. Mmm, this bra really accentuates the shape of my breasts nicely. Just wonder how best to hide my cock, as these panties are so skimpy? Bit of a problem really as I still manage to get excited when getting dressed, no matter how many times I've done it.
As if on cue, my cock stood up, pushing hard against the fabric of my panties as if it was looking for a way out. "Stay where you are," I said out loud, at the same time smiling to myself as I realised that I was talking to one of my body parts. "You might get some action later… not now."
I decided on wearing a white mini skirt and a black, clingy top--with a low scoop neck and small white motifs all over it. This skirt usually shows off my legs for the best and you can just about see the tops of my stockings once I sit, I thought. Should be a good enough outfit for Janice's husband. Now how shall I do my hair? Tie it up and go for the sexy, sensual look, or leave it down to give me a wilder, 'babe' look?
Just over an hour and half later, I stood ringing the bell of the address I'd been given, a curious tingling sensation working it's way up and down my lower stomach, making my stomach quiver slightly. Hmm, I don't usually get too excited these days when coming to see 'clients'. Maybe it's just like the feeling a virgin gets on her wedding night. Hmmm, but where's the virgin?
Yet when Janice opened the door, my first reaction was that the tingling sensation must have been caused by the 'antenna 'in my groin--otherwise known as my cock--detecting that I was within a few feet of a seriously beautiful woman.
Janice looked sensational; like someone that you'd expect to see displaying her charms in one of those girly magazines or in one of those high end underwear advertisements--usually adorned only in black underwear--you know, one of those Victoria Secrets or La Perla models. She flashed me a disarmingly beautiful smile, "Well, well, well what do we have here?" she asked, rhetorically, talking a step backwards to look me up and down. "Quite a 'looker' aren't you? The complete woman."
My cock has already decided it liked the look of Janice too, as I felt very swift movement in my panties as my erection swelled.
I could make a comment about her being a 'looker' too, I thought, what with her dark brown eyes, high cheekbones and long black hair that tumbles down almost to her waist. Mmm, she looks like a Filipina, maybe 27 or 28. Aaah, I should have known from her accent on the phone. Sex-ee.
"Come on in, come on in," she continued. "My husband's still upstairs, he's not quite ready yet," she explained, and I thought I saw a slight grin play at the corners of her mouth.
Hmm, maybe even younger than I first thought, possibly not even mid twenties, I mused, as I watched her turn and wander off into the living room. What a figure. Lovely hips, long slim legs and a bust to die for… and as for that micro denim skirt she's wearing, jeez, it's…it's dangerous!
I limped after her, my cock straining in the elasticated panty girdle I wore over my skimpy, silk panties, beginning to wonder how long I could keep an erection as hard as the one I had at that moment. Don't want to injure myself; I smiled wryly, as Janice's back was still turned to me.
"Do have a seat," Janice said. "My husband should be down shortly. It takes him longer than me to get ready," she smiled.
An awkward silence followed for a few minutes as we both weighed each other up, until Janice suddenly said, "I've never met a Tranny before. Have you…er, have you had any operations or anything? Take hormones? You're so feminine. I'd never have known you weren't a real woman if I'd met you in another situation."
I smiled graciously at her, still trying to control my cock, yet recalling how forthright many Filipinas usually were. "No, what you see is almost all natural, most of it originally me," I explained, only telling part of the truth. "Well, with one or two exceptions. It's amazing what a bit of make up and some padding can do," I laughed--probably louder than I would have normally, but I wanted to try and put her more at ease. "So tell me, what would you like to do now I'm here?"
Janice's face flushed and I could see from her body language that she was going to have some difficulty explaining to me what I was required to do. She touched her face, gently rubbing her chin. "Oh, sorry Samantha, would you like a drink?" she enquired, avoiding my question. "I should have asked you earlier."
"Water would be nice, thanks."
As she went into the kitchen to get my drink, I suddenly remembered that she had originally said on the phone that my presence was for her husband's 50th birthday. Ah, typical, I thought. Older, well-established, foreign guy marries young Filipina. He's probably been a lifelong Tranny and thought an attractive, young wife would change him--only it's made him worse. She wants sex more than he does, so he probably talks her into some sexual games which, knowing most Filipinas, she's only too happy to go along with…. then he announces he's a cross dresser (sounds better than a Tranny), hoping she'll either accept him or back off on the sex bit…
"Oh, here's your drink, Samantha," said Janice, interrupting my thoughts. "Now where were we?"
I sat and listened as Janice briefly explained what was expected of me, and how they'd decided upon hiring me. The requirements I'd heard a number of times before and didn't appear to present any major problems, save that my cock was still sending urgent message to my brain as I found myself thinking about Janice and what lay in her panties
If the truth be known, from what Janice went on to tell me, perhaps not in so many ways, my assessment of the older guy/young wife situation was not too far off the actual position, save that it seemed to me that her husband was more than a Tranny--he was teetering on the edge of transitioning! And that was something she didn't want, not if she couldn't have a replacement cock.
I was just thinking, quite facetiously really, if her husband did transition, whether I should offer her my cock as a substitute--it certainly seemed to like her as I said earlier--when I heard footsteps on the stairs. Moments later, a very attractive 'lady' in a black, short cocktail dress swept into the room.
Looking only, probably, ten or so years older than me, she still cut an impressive figure--slim and long legged despite her relatively advanced years. Black stockings, black shoes, a lacy shawl draped around her shoulders; beautifully made up, wearing dangly earrings and a silver necklace--all topped off by an auburn coloured wig (I assumed it was a wig as not many fifty year olds have a thick head of auburn hair).
Wow, I thought, she looks good, very feminine, very passable. Wonder why she's waited so long to think about transition?
"Hi, I'm Lucy," she breathed, a slight huskiness to her voice, but certainly a voice that was more female than male. "Nice to meet you, and thanks for coming," and she flashed me a genuinely warm smile.
I nearly said, 'I haven't come yet', but that was just me being facetious again, so I just said, "Pleased to meet you too. I'm Samantha," stating the obvious.
Lucy sat down opposite to me and began, "My wife, er, she explained, did she?"
"Yes," I smiled, trying to put her at ease. "Should be no problems."
"Good. Well, let's have a proper drink then," Lucy said, noticing my glass of water, "Would you like a brandy? I'm going to have one, Dutch courage and all that. Hmm, I'm shaking with nerves."
I shook my head and declined gracefully. "Don't worry," I proffered. "Everything will be fine, believe me."
"Yes, I'm sure it will," affirmed Janice. "Samantha's very nice."
Twenty minutes later, Lucy 'retired' to the bedroom, leaving me alone again with Janice. Wonder whose idea this really was, I thought. Not many wives would arrange something like this for her husband's birthday. Especially not attractive, sexy wives like Janice anyway… wonder what the real story is?
I stood up, discreetly adjusting my cock in my underwear, moving my balls to a more comfortable position, and looked across at Janice, silently willing her to ask me to make love to her or at least fondle her breasts before I went to 'service' her husband. But she didn't ask and so I flashed her a broad smile, and simply said, "See you later, then."
"Yes, hope so," she replied and lay back across the sofa, curling her legs under her, yet giving me a look that made me think there might be some hope for later.
"Do come on in," called Lucy softly, as I tapped lightly on the bedroom door a few minutes later. "It's okay."
As I gingerly stepped inside, my senses took a moment or two to adjust to the semi darkness, the bedroom being lit only by a small bedside lamp. I could see somebody, which I took to be Lucy lying on the large, king size bed and, as I advanced towards her, she said, softly. "Hello there, my love, I've been waiting for you. Waiting for a long time."
Wow, sounds like she's already got herself quite excited. Her tone is pure sex!
My cock was already in a state of semi-excitement as I was still thinking about Janice and the softness and tone of Lucy's voice made it grow harder as I took off my bracelets and put them on a nearby chest of drawers.
"Take your top and skirt off, my dear, and come and join me here," continued Lucy, patting the bed beside her. "I think you've got suspenders and stockings on, right?"
"Yes, just for you," I breathed, hoping it sounded sexy enough. "With a nice big cock inside my panties, all ready for you too."
Once I'd dropped my skirt, undone the buttons of my top and pulled it over my head I took a few steps nearer to the bed. Lucy looked quite magnificent as she lay there--wearing a black, tightly laced corset and stockings and suspenders; strands of her hair falling across her face, accentuating her good looks; her eyes sparkling in anticipation.
Wow, she looks even better than when I saw her downstairs, I thought, slipping my hand into my panties and touching my balls. My cock's all hard just looking at her.
A small shudder of pleasure ran down my spine and circled the tops of my thighs, before it dissipated towards my knees. "Oh, you look very sexy, Lucy," I murmured and lay down alongside her. "Very sexy, indeed."
"Samantha, I want you to take my clothes off slowly and then fuck me with your big cock," began Lucy, rubbing the cups of her corset, her eyes semi closed, her mouth slightly open. "Treat me like the woman that I am. Do what you want with me. My pussy is waiting for you."
"Sure, Lucy, whatever you want," I breathed, as I reached and began to unfasten her corset. "Let's have a look at your cock first, though shall we?"
Lucy signed deeply and I could feel that she was almost overcome with the sensations that were, obviously, flooding through her. "No, need to play with my cock just yet, just kiss my pussy," she whispered. "She's waiting for you."
Momentarily, I was puzzled until, in one swift motion, I pulled Lucy's black, lacy panties down to her ankles. Hmm, where's her cock? I wondered, hard to see in this light.
Then, as I moved my face closer to where her cock should have been, I realised what she meant. There was only a pussy staring back at me--one of those fake vaginas that looks so lifelike; curly black hair framing it and moist, soft lips just waiting for a cock to caress it. She's somehow got her cock and balls pulled tight across her stomach, her pussy between her legs. I know they're there because I can feel their shape. But, hey, never mind, everyone to their own.
"Oh, Lucy, so nice," I mumbled and proceeded to suck and chew on her pussy lips, as she writhed around on the bed, clasping her legs around my neck as I worked her, and running her hands around and around the outside of my bra.
"Ooh, oh my God," she cried, as I slipped my tongue deep inside her, wondering how the fake pussy stayed wet. "Oh, Samantha... I don't think I can stop myself coming. Oh... stop, stop, stop."
At this rate, I don't think I can stop myself coming either, I thought. The feeling of you squeezing my breasts and of my stockings slipping and sliding against the silk bed sheets is going to set me off very soon. Hang on in there Samantha!
Lucy, clearly, had greater willpower than me, a greater will to desist and pushed my head away from her pussy. "Oh, Samantha... oh, Samantha," she panted, lying back on the bed with her arms spread wide and her legs wide open. "That was so, so nice! But I don't want to come too quickly. Want to make it last."
As she spoke, she took off her corset and lay there dressed only in her bra and panties, the sheen of her black stockings catching in the light of the small lamp.
"Tie one of my wrists to the bed. Please. The rope is in the bedside cupboard."
I could feel the wetness of my pre-come around the rim of my cock as I duly obliged her and wondered again how long it would be before I came once we started the 'action' again.
"I've always fantasised about being tied up and someone fucking me," explained Lucy. "But it's so hard for someone who's not a Tranny to understand this. They just think you're gay or something but I'm not... it's just that I want... "
"Sssh, don't need to explain anything, Lucy," I empathised. "I know exactly what you mean," I added, truthfully. Oh, the feeling of being dressed up like a woman and have someone making love to you... caress your breasts, run hands up and down the nylon of your stockings, gently ease your panties down, let your cock spring out… is well, all in all, quite indescribable. I know!
I slipped my panties off and grasped my cock, cupping my hand under my balls, and showed Lucy what she was about to receive. "Look, Lucy. Look, I'm going to slip my big cock right inside your pussy in a minute," I said, holding my organ only a few inches from her face. "Then, I'm going to make you shout just like a woman does. Shout as loud as you want because that's what I'm here for."
Lucy swallowed hard and I could see expressions of pleasure dance across her face. "Oh, Samantha," she gasped. "Tell me that again. My cock feels like it's on fire. I don't know how long I can wait before I come, especially when you talk like that! Say it again."
So, I told her again what I was going to do then, without further ado, slipped my cock into her pussy. I must admit the feeling of being inside one of these fake pussies was almost as realistic as being inside a real one. Wet, warm and a big turn on. Oh, so nice, almost as good as the real thing, I thought. Maybe should buy one myself.
Lucy was right about one thing--once I was inside her it didn't take her long to come. She rotated her hips a couple of time, tightly grabbed my back (almost pulling my bra off in the process) and thrust her hips hard against mine. "Ooh, ooh, ooh," she began, her rhythm building with each nano second that passed. "Ooh, oh, oh my God, my God, my Go-rd. oh, Samantha!" and she dissolved into a series of cries and screams that told me she'd reached the very pinnacle of her pleasure.
She grabbed my arse, digging her fingers between my cheeks and holding my lower body tightly against her--as if she was worried that I'd try and withdraw my cock or something. As her orgasm finally subsided, her breathing seemingly taking an eternity to return to normal, I felt the beginnings of a wet patch radiate from under her and seep along the sheets, touching my balls where they came into contact with the bed sheets. Oh, all my come is flowing out of her pussy, but she doesn't seem to mind. But how did she manage to come with her cock in the position that it is, I puzzled. Anyway, she did it, but must take some practice!
"Now it's your turn," Lucy whispered. "Let me make you come. You can fuck me from behind if you want--you can still get your cock up my pussy from there if you get close enough."
"No, let's stay like this," I suggested, still lying on top of her. "If you don't mind that is. I like the way your pussy feels from this direction. So soft and wet."
Just as I finished speaking and Lucy had opened her legs again to let me re-enter her, I thought I heard something behind me. But I was concentrating on the matter in hand, namely to get my cock back up inside Lucy as soon as possible, and was paying little attention to anything else. A slight draft seemed to waft into the room as if something had disturbed the air motion. Hmm, was that the wind, or something else? Oh, never mind.
So, it came as quite a surprise when, just as I had slipped my organ into Lucy's pussy again, I felt a presence close to me. Sensed another person standing by the bed. Smelt the aroma of another person close to me...
As I turned my head to the left slightly, still prodding Lucy with my cock, my mouth dropped open. Just at about my head height, I came face to face with a long, black erect cock.
My God, what's that? I thought, rhetorically. Where did that come from?
It looked to be about nine inches long, with perfectly shaped balls hanging below it... all attached to a slim, sexy and totally naked person standing right alongside the bed. I strained my neck and looked upwards to see a pair of the most beautiful breasts I've seen for a long time; hanging loosely, nipples dark and erect.
"Oh, Janice. Just in time," gasped Lucy, her breathing intervals becoming shorter and shorter as I kept thrusting my cock in and out of her; her pleasure gripping her again. "Samantha's just about to...to try and make me come for the second time. Come and join us, my dear," she murmured, between gasps.
Janice needed no second invitation and climbed on top of me, sitting astride my back and straightaway running her cock over the cheeks of my bottom and into the small of my back.
"Ooh," I shuddered, involuntarily, "nice."
"Yes, I was hoping you'd say that," the woman said before she nuzzled my neck, then let her tongue linger in my ear as she licked around the side of my face. "This won't hurt, Samantha my dear. Just relax and I'll be inside you in a moment."
Lucy was stronger than I had thought and managed to lift both of us off the mattress, lifting and dropping her hips as she sought to find the 'trigger' for her second orgasm, my cock by now moving in and out of her like rapid fire. "Ooh," she groaned, repeatedly. "Ooo…"
"Ooh, Samantha," groaned Janice and she wiggled her cock close to my arse, trying to find the right entry point, leaning forward and letting her breasts rub against my back.
Christ, I'm the meat in the sandwich, I thought, feeling my breasts rub against Lucy's bra and my stockings slide against Janice's bare legs, as she wriggled and writhed, trying to seek the optimum position on top of me. What do I do?
The answer came within thirty seconds of Janice penetrating me. I came. A huge orgasm. Lots of noise and sweaty movement, but I came.
"Oh, Jeezuz," I cried as my cock repeatedly dumped all the come that had been building up in me since I'd arrived at Lucy and Janice's into Lucy's pussy. "Oh, my, my-yy, Gord!"
My cock still worked in and out of Lucy's pussy so quickly that I wondered, for a few seconds, if I'd get friction burns. I clawed at Lucy's breasts, feeling the need to scratch at something other than the bed sheets and, for a second or two, almost considered biting her neck.
Janice was in full flow and, if you've ever had a strap on up your arse, you know that it only adds to the excitement that's already causing your cock to tremble by being inside a pussy--fake or not.
My coming set off a chain reaction as, firstly, Janice pumped me from behind, shouting and screaming so loudly as her orgasmic wail took hold of her that I was quite worried for a moment or two about my eardrums.
Her thrusts into me kept pushing my cock harder and harder into Lucy and Lucy, to her credit, managed to flood the bed again--still with one hand tied to the bedpost!
The afterglow, if that's what one can call it, was interesting as we all lay in a heap on the bed.
Lucy dishevelled and wet, with come under her and down her legs; me with Janice's pussy juices having made small wet patches on my bottom; me unable to get off Lucy until Janice dismounted from my back.
And Janice, exhausted and content still lying on top of me, her warm breasts and still-hard nipples occasionally touching my back and sending small currents of pleasure down into my lower spine area.
Wow, I thought. I've certainly earned my money tonight. Mind you, I'd actually offer to have sex like that for free if I had too--not that I'd tell any of my 'customers' though!
Janice stirred slightly, interrupting my thoughts.
"Could we do that again?" she whispered softly, placing her lips so they rested against my right ear. "I'll take this strap on off and you can put your cock inside me this time, though... "
"Sure," I murmured, "just give me some to recover," trying to ease her from my back.
"You're very naughty, Samantha," Janice continued, whispering into my ear almost inaudibly, "you never told me you'd had your breasts done when I asked you earlier if you'd had any operations," and she smacked my bottom hard once, like a mother to a misbehaving child. "Now Lucy will want hers done too!