Attachment Enclosed

By tina foster

Published on Jun 1, 2008

Transgender

I'd met young John at an evening course we'd both been doing. We had actually met in the queue to sign up, with me dropping a coin and bending to pick it up, the start of the tale. It'd been much later that things got interesting, as it were. And, that was after we'd not seen each other in ages.

I'd introduced him to some friends and soon he'd been socializing with a whole different group of people, very different from the no-marks he hung around with.

I'd really liked his company and some evenings we'd sit and talk, smoke a weed, watch films and all the while, there'd been that sexual undercurrent between us. He knew I was bisexual and one day, had asked me if I fancied him. Of course I'd said `yes', but never pressed the point as it were, as I'd not wanted to ruin the friendship.

Then one day, he stopped calling; stopped answering my calls and emails; and that was it, I'd thought.

I'd resented his disappearance from my life, wondering if he'd just used me in order to meet those I'd introduced him to. `Or was it something else?' I'd mused.

And that might have been it, except for that email and a photo I'd not forget in a hurry. In the subject line it had said, `check this out' with an attachment, a .jpg. Needless to say, curiosity had got the better of me; and, I'd opened the attachment. There on the screen had been a pretty large fleshy member, the crown bigger than most I'd seen.

I'd seen that picture before, just after I finally confessed that I enjoyed wearing women's lingerie and that the slip of pink lace that he'd noticed above my coal black jeans that time we met at college wasn't a one-off, as I'd insisted that it was.

That admission of mine one evening had led to his question and then to us exchanging photo's, with mine showing some quite submissive poses, dressed in my pretties. I'd liked what I'd seen in his pic and told him so. And, for awhile, every time young John called round to get stoned with me, there'd been that sexual tension in the air; a sweet frission that filled me with anticipation.

Then he'd stopped calling.

Over the days since that email, that photo's image stayed with me, as I had thought of myriad things I'd have done for him. That photo, of his boxers round his thighs, tee-shirt drawn up, to expose his flat stomach; while he held his shaft in his hand. He was about my length, but thicker, with that large-domed cut crown, oozing pre-cum.

And, the message that had accompanied the pic, `Want this?' Simple, direct: to the point. I knew I had to reply; I just had to. But, what to say? I'd not heard from him in ages; and although I'd missed his company, it was that beautiful cock I'd thought of, everytime I'd closed my eyes, to blink. I'd been obsessing and, knew it.

Yet pride kept me from replying. After all, how would it look for a man of fifty to be chasing a young man like this? `Easy, it'd look like it was,' I reminded myself. Finally, after several hours and a couple of whiskey's though, any hesitancy was lost and thought's of lust took over.

I had re-opened the email, then pressed reply. "Very nice," I'd written, the pressed send. When I'd next checked my account, there'd been an answer, a simple one: "Still interested?" It had read. "Yes" I'd replied, having looked at it again, just seconds earlier. "So do you want it?" he had asked. "Oh yes," I answered. "But I do need something Sir, I need a cuddle and my nipples played with first..." "??" "I need to feel femme. Before a man takes me. Is that alright, Sir?!" I think he had liked the honorarium I had bestowed on him. "Yes. Saturday. Be ready..." He knew I'd be free Saturday of course, after all, we'd been hanging together for awhile, till he stopped calling. "Yes Sir," I replied, "I'll be ready."

I had shaved my chest and my legs, then found a crisp white shirt, which I wore with a red wool tartan skirt, that ended mid-thigh. It was tight across my backside and had an elasticised waist, so I'd not too much difficulty easing it over my hips. The panties I wore, were brief, light pink and edged in lace: and, I wore them back to front, so my genitals were hugged into place, with the gusset pulled tight between my arse-cheeks, rubbing hard against my anus, liberally coated with Vaseline. On my shaven legs I wore a middle-denier pair of tights in American Tan. Once I'd finished getting ready, I thought I looked pretty good. Well, at least I hoped that John would think so. Gawd, how I'd wanted him: so badly.

When he knocked on the front door I was wearing my blue terry-towel robe over the outfit, ready for him, yet nervous as hell. Although I'd known a lot of men, this was the first time I'd wanted to submit, to another; not just his femme, but his slut, cunt, whore, anything he might want. I'd opened the door, cautiously at first, as John entered my home, a smile on his face. Then, I quickly closed the front door, anxious to be alone with him. I'd taken him through to the kitchen, where I gestured for him to sit at a bench-seat at the table. "Do you want a coffee, with your cuddles?" I asked with a grin, very aware that John was staring at my nylon covered legs, with a smile, as I'd motioned round the kitchen. I was so sexed-up I'd do pretty well anything he wanted of me. But thankfully, John didn't know that. He wasn't aware just how bad I wanted his cock. "Why don't you take the robe off? He asked me, with a distinct leer on his face. The curtains were open and I already felt quite vulnerable, my femme clothes neath the blue terry-towel bathrobe. No matter how much I wanted him, or rather his cock, that was asking too much, I thought. I looked at him; this wasn't the quiet lad I'd developed a friendship with. "If I'm taking this robe off, can I do it in my room, please Sir?" I added the Sir, as I knew that John liked it. Yet he was quiet, still looking legs. I didn't have heels; though I'd like to have worn them, for him. But, from the end of the robe down, it was apparent what I was wearing and it was obvious from the look on his face, he liked what he saw. I felt very conspicuous. Other than the ex, who'd taught me of my femme side, I'd never dressed before another. I'd cottaged, before her. I liked cock. But, John would be my first, in ever-such a long time. He would also be the first to see me dressed in my pretty-things, since Tina. "I'll put on some blue for you to watch, while we cuddle," I encouraged, then added as an afterthought, "and there is a joint waiting in the ashtray." Still nothing. But, I noticed him lick his lips. It was plainly evident john wanted me, a lot.

"Finish making the coffee," he instructed. He stood and made his way to the kitchen door. "I'll be waiting for you, okay you slut..."

I hadn't expected him to call me that, but then I hadn't expected the email he sent either. Besides, `slut seems appropriate,' I thought as I finished making our drinks, considering just why I'd invited him round. I was a slut, for that cock I'd seen pic he's sent me. That much was true and the fact that my anus twitched at the name he called me, suggested I was as bad as he thought.

That thought had me smiling, as I walked through the living-room, to my bedroom, where I knew John was waiting for me. `To fuck me?' I hoped so.

Just behind the door, on several shelves facing my bed, were my tv, vcr and dvd recorder. I turned the tv on and placed a dvd in the machine, then stood to face John, who lay in the middle of my bed, left hand behind his head, as he stared at my legs.

Behind me the television flickered into life, adding its light to that of the single bulb above our heads, resplendent in a very seventies blue plastic glove, whorls etched into its exterior.

John was already smoking the joint.

I placed the drinks on the unit to his right and smiled, gently.

"All I want is cuddles and my nipples played with John... er, Sir and I'll be your willing sub."

I looked at him, `arrogant sod'. He knew it was not mere words, I'm sure. John must've realised my need and how he could use it. And boy, had he been right.

"You want cuddles, you do something for me..." he said flatly. I was going to say, `that wasn't the arrangement.' But I couldn't, not with the prospect of his cock in me so near. I just couldn't. "What do you want Sir?" I asked in a quiet voice instead.

He lay back on the bed, caressing the bulge in his groin. "Show me your legs," he told me. Nervously, I'd hiked up the hem of my skirt. My arousal was evident; but that wasn't why he was here.

"Turn round," young John told me, with lust in his voice. I did as I was told, doing so slowly, as I drew the skirt higher still. At last he could see my nylon-clad buttocks, with a hole cutaway in a strategic area, for ease of access.

"Nice," he murmured in a soft-voice, raking another hit off the joint. I was looking down at my toes, as I pulled my buttocks apart, so he could see where I wanted him: as blatant as that.

Then as I used a few fingers to pull the panties gusset to one side, I easily slid two-fingers into my well-lubed hole. I eased the fingers in and out gently, till they were as deep as they could be. Then I pulled them out slowly, leaving me wanting, more. "Can I join you, for cuddles Sir?" I enquired, as I looked over my left shoulder. "Yes," he grinned. I straightened my shirt and smoothed my skirt back down over my full buttocks, then turned to walk toward the bed. I lay on his right on the outside of the bed and as I cuddled up to him I drew my right nylon clad leg over his right thigh. He felt tense and uneasy as I ran my right hand over his firm chest and down his flat stomach, as I undid the zip on his windcheater, then began undoing the buttons on his shirt.

"If you enjoy it Sir," I whispered in his ear once all the buttons were undone and ran my hand across his taut belly.

"You can do me again, any way you want and dressed any way you want," I added, as I ran my hand toward his belt buckle, , looking down at his smooth bare flesh, so young, so lovely. Then my wandering hand moved downward, to the clasp of his jeans, which I snapped open.

"I want to dress like this again for you and be you fuck-slut. If you like, Sir," I said softly to him, as I slid my hand inside his jeans, delighted to be with him.

I was hard, yet that was irrelevant. I was just cunt to him, a hole to fill: and then and there, that's just what I wanted. His cock and my need were all that was important. That and the idea that he might call again: to use me.

Yet despite all my attentions, John just lay there, watching the screen, as a luscious Brazilian SheMale shook her long dark hair, just prior to undressing in a hotel room. Like him, I watched the scene unfold, as the Latin lovely began to stroke a medium-sized, circumcised erection, staring into the camera and thereby me, the viewer.

I looked quickly to my left. John was engrossed by what he saw; and his hips rose almost unconsciously to my touch and it was apparent from his breathing that he enjoyed the feel of my hand on him. He was wearing white boxers and he filled them well, my hand could attest to that. Yet, it was that cockhead that fascinated me, it felt massive.

I rubbed John's length gently, slowly: and he groaned softly.

Would I be able to take him, I'd wondered.

Then John passed me the remainder of the joint and I inhaled deeply on it, anxious and horny at the same time. Oh how I wanted him, to use me.

"Please Sir, play with my nipples..." I entreated, pressing up against his young, toned body, aware that my needs weren't his, whilst being mindful of his erection.

John was hard, he wanted a hole to fill: `after all, wasn't that why he was here?'

"Please Sir, I whispered, desperate for his touch, "please play with them. Make me feel really girlie and ready to be fucked."

I inhaled again, closing my eyes a little, as a mild euphoria swept through me and then began to feel elated, as young John's left hand undid two of the middle buttons on my shirt and slid inside.

I loved the feel of his smooth, small hand on my flesh: and I adored it, as it moved upward, toward my right nipple, already aching for his touch.

Stubbing the roach into the ashtray, I squirmed with a long groan of pleasure, as his palm grazed my erect nipple.

"You do want this, don't you?!" He queried: as I savoured his touch, imagining the look on his face as he questioned me.

"Oh I do, Sir..." I sighed.

"And I get what I want?"

"Oh yes Sir," I assured him, eager for him to continue what he was doing.

He squeezed the flesh, between forefinger and thumb and I opened my eyes, to see him smile, as I winced in pain.

`Would I do what he wanted?' Of course I would.

Shit, with what he was doing to my tit-flesh, I'd soon be feeling real girlie and ready to beg for his cock.

"Thank you," I murmured against his neck, as he mauled and mistreated each nipple, in turn.

Within a heartbeat, I groaned with pleasure and slipped my hand beneath the elastic of his white jockey's, to take his warm fleshy tissue in hand.

I edged the elastic over the dome of his powerful, young erection, revealed in the flesh, as it were.

Uncovering it fully, I began to caress him. Not that much longer than my seven inches, like me john was circumcised, a little thicker than me, with that dome-head that was much wider in real life than I'd first thought, seeing that picture.

He pinched my right nipple hard, as I slowly pumped at his flesh.

The pain, my femme attire and his cock-in-hand: It couldn't get better. Then it did.

He kissed me. John turned his face towards mine and actually kissed me. Heaven.

My lips opened and I held him with my free hand, as his tongue entered me and his nails bit into my nippleflesh. Ecstasy.

"What do you want now, Sir?" I asked eagerly, as he drew away from me a little, still torturing my left nipple.

"Now?" He asked, snapping his nails together and blinding me momentarily with the sheer pain of it, before he moved to the right nipple.

"Now Sir, anything, anything you want..." I murmured against his neck, as he pinched hard into my tender flesh, before snapping his nails apart, as he had earlier.

"Oh yes," I hissed, breathless.

"Onto the floor and over the bed. Is what I want..." he muttered, sliding me of the bed and onto the floor and my backside.

"Get over the bed," he told me, with a smile, as he stood himself, his hardon bobbing as he did so, already leaking pre-cum.

I knelt on the sheepskin rug on the floor, and then resting my upper body over the bed I hiked up my skirt.

Gawd, I wanted him inside me. I was eager, very eager.

I looked back, over my left shoulder, as John knelt behind me.

Cupping my right buttock, John's fingers glided onto my flesh, where I'd cut away the tights for that very purpose.

"You're ready to be fucked, aren't you?" John asked, as he slipped his finger under the pants gusset and pressed it straight onto my anus.

"Yes!" I replied, wriggling my buttocks to feel the finger better, encouraging him to enter me.

A fingertip teased my well-lubed pucker open; and as it eased into me, it was joined by a second.

I'd groaned against him, as John opened me up; and the gusset of the pretty panties was no obstacle.

Then, fully inserted, he began to move those fingers back and forth, widening me further, as my muscles relaxed somewhat.

"I think you're ready for me, now..." John told me, slapping my left buttock.

Slowly he pushed the head of his proud, young cock against my anus, watching my face, smiling, as my sphincter opening to accept it. The lube helped, but the fit was still intense and painful. I felt I was slowly being split in two. When it was fully inside me, I groaned. But, that was just the head.

Now he eased his length fully into me, until his belly rested against my buttocks.

Momentarily, he stilled all motion, a look of intense concentration on his face. For a second I thought he was going to cum, then hands on my hips, John began to pump his hips back and forth, his flesh in me. It was deep and intense.

He started to thrust steadily and deeply, full-length penetrations, ending with the thump of his pelvis hitting my buttocks, as I pressed back against back against him.

He maintained the slow rhythm initially, as I revelled in him fucking me, with my face pressed into the duvet. My whole being was focussed on John stretching the ring and the sensation of that hard shaft sliding through it, and the wonderful feeling of being full, as he possessed me a little more with each thrust.

I could feel my anus being pulled in and out, as the speed increased, as with each thrust John became more urgent, his breath heavy, as sweat dripped onto my backside.

Soon his thighs were slapping on the back of mine, his ballsac swinging against my buttocks.

John grabbed my shoulders and with each stroke deep inside me, he pulled down on my shoulders, pulling my body to meet his thrusts.

"Oh yes," he exclaimed, as he pumped his length into me, harder and faster.

With each powerful stroke, I grunted in pleasure and pain, as his thick cockhead stretched me. I had got what I wanted, his beautiful cock, inside.

I can sense that John is close to cumming, as he bangs hard, making my anus sore as he hits sensitive spots inside, Yet, I'm becoming very excited by the roughness of it, and the feeling that John doesn't care how I feel, only interested in his own needs.

I'm his slut; his whore; his cunt, to use and abuse. I love it and want it to last. but, it is apparent, by the tremor in his thighs, his grip tightening on my buttock flesh and hips that he will cum very soon.

"Oh, yes. Fuck it, I'm going to fill you now," John began to suddenly grunt and shout, as he begun to thrust without any hesitation.

As it was withdrawn, my anus was pulled with it, as it was thrust in, my anus was forced back into him. Inside, I felt a great emptiness as the prick was withdrawn, and then the beautiful sensation of overwhelming submission as pushed back into me, refilling that space inside me.

John was gasping now, very close. Then he is there, thrusts deliberate and deep. I can could feel his spasms deep in my belly and in the shaft, which my ass walls gripped so tightly.

I can almost imagine, that moment he exalts his cries, I am his woman being filled with is seed.

Abruptly I cum myself and I flood my panties, with my own cum, at the thought of it.

"Oh yes, I can think of several of my mates, who're desperate and want a bit of ass, just like this ..." he says to me, caressing my buttock-flesh, as he wilts and plops out of me.

I feel empty, without him inside me. I want more of his hard youthful cock, filling me: and I listen, as he quietly dresses.

As I lay panting, I looked back to see John finish button his shirt, zip-up his jeans and buckle-up his belt. He looked distinctly thoughtful, I mused. "Yeah, that wasn't bad at all ..." He said finally. "So, you'll be back again?" I asked, hopefully.

The scene on the television was an attractive brunette on all fours on a patio on a sunny day, sans bikini, a mouth full, cheeks parted, as another pressed forward.

He turned from the moving image on the screen and back to me. I lay over my bed, as he'd taken me: a submissive toy, `coz that's how I felt.

John was obviously thoughtful, while I felt shagged out, literally. I seemed to contract after he'd pulled out. Now I relaxed those muscles, I'd held since then: and I feel his cum leak from me and down my left inner-thigh, into the edge of the nylon.

I listened to John talk, half to himself, with growing interest. I had two-fingers knuckle-deep, but I wanted more.

"You could entertain one of `em, every Saturday..." Then he stopped, watching me as I swirled cum coated fingers inside myself.

"Of course there'll be something in it, for you..." he told me, "but not money, of course. My friends are always broke." He paused, deep in thought. "I know, they'll give you a weed for your services..." He furthered, adding to his ideas.

"An I'll want my nipples played with awhile, before they fuck me," I suggested, getting, into the spirit of it myself.

"Yeah I guess, why not?" he retorted blithely; "After all, you'll sure as hell be satisfying them."

It sounded enthralling.

I wanted to cum again, I was aching for it: and his words increased my arousal. "Though by the looks of things, a weeks going to be a long time for you to wait for you, won't it?" John said to me, with a light smirk, as he fastened up his windcheater jacket.

"You're leaving?" I whined in desperation. Oh-Gawd, I needed filling, badly. "Yes," he told me, watching as I drew my fingers out. He continued to watch, as I grouped together my fingertips, then eased them into anus, stretching myself wide, to his gaze.

He liked that he saw and that was apparent. So, I was all the more upset when young John said to me: "Have fun. And, be waiting for a phone-call at about 12:00, or so..."

Realizing I couldn't stop him, I stopped fucking my cummy hole and made to stand.

"Nah, slut..." John started, don't stop. I'll see myself out."

I got back onto my knees and pushed my steepled fingers back into as John closed the bedroom door after himself, as he left the house.

Much as I was disappointed that John had left, I was eager to fuck myself at the thought of being his whore, for his young friends.

`Would there me more to cum... ?'

tinafosteruk@gmail.com

Next: Chapter 2


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