My New Career

Please find below the fifth part of my story, for inclusion in the Transgender Control section.

• Amanda Stern

Welcome to the fifth chapter of this kinky tale. if you have any comments or reactions, please don't hesitate to email me, as I adore hearing from anyone who shares my love of crossdressing, writing or both. And do think about donating to help support this wonderful site.

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MY NEW CAREER - PART 5

Spent, streaked with sweat and still amazed, naked except for the ubiquitous stockings, I walked on unsteady legs to the bathroom, closed the door and leant back against it, trying to collect my scattered thoughts.

I had faced a lot of challenges in the past couple of months. The ruthless feminisation that had been imposed on me, to the point where I was finding it hard to remember what it was like to walk or talk like a man, let alone look like one. Being forced to abandon what I'd thought of as a career in teaching and instead work in a strip club, flaunting my body and teasing voracious men into giving up cash. The sick feeling of helplessness every time I was reminded just how much the Ceder College controlled my existence. And much more besides.

But this was something else again. I might have lost all the trappings of masculinity, I might have started even thinking of myself as Katy, not Martin. But regardless of the humiliations heaped on me, I could retreat within myself and find that core of feelings and desires that still belonged to my old self. Or so I'd thought ...

I walked to the basin, washed my face and then mechanically started

brushing my hair and repairing my makeup. And as I did so, I thought again about what I had just done ... and wondered, what had happened to make me love it so much?

The initial shock at being sent to dance in Club Angel had gradually worn off over the next few weeks. Although much of my time was still spent in lessons at the College, I was rostered to work for an hour or two each day.

While I always started with a show on the stage, much of my time was in fact spent around the club mixing with the clientele. I was expected to chat with them and encourage them to buy me expensive drinks (which I was instructed to pour away when they weren't looking) or, preferably, to pay me for a "private show". These were held in separate booths and involved me stripping off my clothes (at least to my panties), teasing the client and letting them fondle my body - again, except between my legs.

My fears that I wouldn't have enough on my chest to display, or that my real gender (or what I hoped was still my real gender) would quickly be rumbled, were dispelled on my second visit to the club, when I was asked by a client whether I was "one of those girly boys".

It seemed that the customers were fully aware that some of the "girls" in the club were naturally female, and some weren't: indeed it appeared to be something of a selling point. Most of the clients who wanted private shows could already see I was sufficiently flat-chested to probably be a guy underneath. Those that couldn't either asked, or found out in the booth - and not once did any of them show any irritation at my being something other than all woman. In fact there was probably an element of self-selection: if they'd wanted a more busty or curvy dancer, they wouldn't have approached me in the first place.

Despite this, I still found myself feeling disappointed sometimes that I didn't fill out my glamorous costumes, or have more to display when I took off my top. Once or twice I even thought about asking Mr Everett - who I still tended to see only at the club - if I could use some of the fake boobs he'd mentioned. But that really wouldn't have made sense - the artifice would have been exposed (so to speak) the minute I started undressing.

What was really scary? The fact that I'd caught myself wondering what real breasts would be like ... That and something else: the arousal I sometimes felt now when turning men on. It wasn't any kind of attraction to the clients themselves - or at least I didn't think so. Even if they were young and good-looking - which most weren't - I didn't feel any urge to touch or kiss them. But if I made them excited, if I saw or accidentally felt their erection ... well that made me tingle. And just a little bit hard myself ...

Worse still, it was happening at home. I had bitten the bullet and agreed to move in with Graeme, my landlord. I simply didn't see any other option. For the first few nights, he had insisted on sleeping on the couch, chivalrously insisting that I take the bed to get what he kept calling my "beauty sleep". But after seeing him so stiff and sore in the morning - hardly surprising, given the need to squeeze his large, sixty-something frame onto such a short sofa - I had taken pity on him and agreed that we both use the bed.

It was a queen size, big enough so that we weren't on top of one another. But with the nights getting colder, it was only natural sometimes to huddle together for warmth. And after leaving me alone initially, he had taken again to wanting to kiss and cuddle. In the circumstances, given that I was getting free board and lodging, it seemed churlish not to let him have his fun. Besides, I'd got used to it ... and there was something oddly endearing about his passion, his excitement, his sheer wonder at making out with the gorgeous creature he clearly thought me to be.

And where kissing started, so arousal followed. And I would wrap my hand around his meaty cock and sometimes pump, sometimes tease him to release. He never asked me to do more, though I could see in his eyes he would have liked to. And I felt no urge to go further. But what I did feel, increasingly, and confusingly, was an arousal of my own - something I went to considerable pains to conceal, but fretted about all the same.

All in all though,, my life at home had become much easier, even pleasant. Graeme was good and attentive company, treating me in many ways as a kept woman. He cooked for me, took me out for dinner or a movie once a week, and brought me pretty clothes. He especially loved getting me lacy lingerie, which I would model for him or wear to bed - something which in turn increased both his ardour and his chances of getting a handjob. I mean, it seemed only fair ...

The College had also loosened some of their controls somewhat, even though it was still made very clear to me that I had no choice at all about either my lessons or my work. While I was still expected to be in high heels when I both arrived and left, the biometric lock that had previously kept them on until late each night had been removed. By now I had got used to them anyway, so while I certainly no longer wore them while at home, it was rare for me to go out in anything else.

Truth be told, I had come to love the feel of the clothes I wore, the way the different fabrics moved against my now permanently hairless skin, the way I looked. I felt ... sexy. As my hair had grown out, so Lily and Daniel were able to experiment with different looks ... as indeed I often did now as well.

Today I had it braided and then tied back into a tight bun, with a few stray wisps left to frame my face. The look for the day had been Sexy Secretary, so I had paired an electric blue silk blouse with a tailored black jacket and a very short black skirt which showed off my legs, looking fantastic in patterned black nylon and six-inch pumps. In fact, the look was really Fuck Me Hard Over a Desk, and judging from my earnings at the club, that's exactly what some of my clients would have liked to do to me ...

Unusually, I was wearing my day outfit to go home in this evening, rather than changing into more nondescript clothes. For one thing, I wasn't going straight home. And for another, I had my own sexy secretary to see.

Catching up for a drink with Grace had become the high point of my week, without exception. Although she remained very reticent to talk about anything that happened at the College, or her life away from it, we still managed to find a lot to chat and giggle about.

As I walked into the drinking hole she had chosen this week - we always tried to move around, as well as avoiding anywhere the other College staff were known to frequent - i had a real spring in my step. But two things stopped me dead in my tracks as I caught sight of her at the bar. Unusually, she was still wearing her work uniform - an outfit very similar to mine, but with the classic white blouse, unbuttoned to display more than a hint of cleavage. And she was talking to two young men in suits.

As I stared at her she caught my eye across the room, waved and then said something, smiling, to the men. With a laugh she left them and came over to greet me. "Hey girlfriend!" she called brightly and stepped in close to peck me on the cheek, lightly resting a hand on my hip. As she did so I felt a familiar shiver at her nearness and inhaled her delicate and familiar aroma.

"Hey yourself", I returned. Jerking my head at the two men, I asked as lightly as I could: "Who are your friends?"

She smiled, took my hand and led me to a table. "No idea", she said, "I think they were just trying to chat me up. Not my type though ... Okay, this looks good, I'll keep the chair warm, you can go get them in." Her smile broadened as she sat down. "It being your turn to buy and all ..."

I nodded my acquiescence and headed to the bar. I was now getting a small amount of pocket money from the College and it was actually quite nice to be able to buy stuff again. I ordered a bottle of our favourite riesling and was just about to pay for it when a voice beside me asked: "Any chance we can take care of that and help you two gorgeous young ladies drink it?"

I turned around to find one of the men Grace had been talking to smiling at me, his eyebrows raised. He was really good looking ... if you liked that sort of thing.

It was not the first time I'd been approached while out with Grace. And I'd become pretty comfortable talking with guys at the club. Keeping my voice soft and a touch higher than my natural tone, as I'd been taught, I affected a look of surprise. "Oh wow, that's really sweet of you. Only ..." I gave him my most dazzling smile.

"Thing is you see, my friend and I have got to drink up quickly, then spin the bottle to work out which one of us is going to eat out the other's pussy tonight. And do you know how much we love having men watching us and then joining in? That's right - not in the slightest. See ya!"

Taking my change, the bottle and a couple of glasses I strode back to the table, putting an extra wiggle in my hips. Grace was staring at me. "Oh my god", she said, "what on earth did you say to him??? He's still trying to pick his jaw off the floor ..."

"Who, me?" I asked innocently, sitting down and then pouring out the wine. "Nothing really ... Now, tell me why you're still playing the secretary babe, I thought you were sick of that outfit?"

She took a long pull of her drink and then grinned at me. "I am, usually, but I saw what you were wearing today and I had a feeling you were going to keep it on, so I thought it'd be fun if we, you know, matched ... Now anyway, tell me how things went today at the club, I want to hear about every tease you put those poor men through ..."

So we talked, and drank, and talked some more. And somehow one bottle turned into two. We didn't normally drink so much, but we were both in a buoyant mood and the time slipped past as easily as the wine slid down our gullets. By the time we got up to leave, we were both more than a little giddy. As we walked slowly to the exit, concentrating hard to stay on our heels - or at least I was anyway - Grace turned to me, her face serious for virtually the first time that evening,

"Listen Katy", she said, slurring slightly, "would you mind coming back to my place? It's not far from here and there's something I'd really like to show you ..."

I was surprised, as I'd never seen her apartment, though I knew she lived near the city centre. "Sure", I said, "why not? Only you'd better be offering coffee rather than more wine, or you'll have to roll me into work tomorrow ..."

She nodded gravely, made as if to say something, then taking my arm in hers, led me outside. "It's this way", she said, "won't take us long ..."

In fact it took a good twenty minutes, at our admittedly slow pace. But soon enough we were walking into the hallway of a very modern and well appointed apartment. As Grace closed the door behind me I peered into a spacious living room, with a gleaming and well equipped kitchen beyond it.

"Wow", I said admiringly. "I had no idea you lived so well!" Turning back to her, I continued: "Want to give me a tour? Unless of course you want to show me whatever-"

The sentence was cut off as she grabbed me and pushed me hard against the wall. For a moment she stared at me, her eyes wild. Reflexively, I tried to ward her off. But my cry of alarm was cut off as she leaned in and crushed her lips against mine. After a moment of consternation, I returned the kiss. Her lips felt so soft and creamy, so different to what I'd become accustomed to with Graeme, her tongue darting into my mouth ...

I gently disengaged, pushed her back so that her face came into focus. Her eyes were wide, her expression almost scared. I shook my head. "Tastes so different", I murmured inconsequentially, "kissing a girl with lipstick on ... On me, I mean. Or both of us ..."

There was a pause and then suddenly we were in each other's arms, kissing again, pressing tightly against one another. And my hand was running down her back, stroking it, then reaching lower to grab her behind, just as I felt her doing the same to me. As our nylon-clad legs came together I thrilled at the contact, marvelling at the sensuous feel of the fabric.

After a long moment we broke apart. Her expression was still intense, but determined now rather than afraid. "I want you", she said in a low voice, then drew me down the corridor into what was obviously her bedroom. Turning back to face me, she threw off her jacket, then slowly, looking at me the whole time, unbuttoned her blouse, and unclipped the white, lacy bra that lay beneath. Reaching down, she took both my hands, then brought them up to place them on her soft, inviting breasts. As I gently stroked the nipples,I felt them come alive under my touch. She moaned softly and I let out a shuddering sigh. "Oh Grace ..."

And then we were on the bed, pawing and groping at each other, crying incoherently as we tried to tear off our remaining clothes and simultaneously bring our bodies together. I was quickly down to my panties

... but then stopped, suddenly afraid to reveal what was underneath.

But Grace did not hesitate. With a smooth movement, she pulled my panties down, disengaging my engorged member from its protective sheath. With one hand on the shaft, she used the other to push me down so that I lay flat on the bed. Then, after kissing me once more, fiercely, she took her head to my groin. In a second she had enveloped my straining cock in her warm, wet mouth.

The sensation was incredible. I had barely touched myself during my time at the College, so wary had I become of my own impulses. And even as a man I had rarely experienced oral sex. So to now have this gorgeous young woman fellating me, her tongue flickering over the sensitive glans as her lips slid up and down the shaft ... there were no words to describe it.

Looking down at her head bobbing up and down, I was sorely tempted to just lie back and let her deliver me the sweet release that would surely not be too far away. But I wanted more ... "Grace", I said hoarsely, "I don't think I can ... last too long ..."

She looked up, grinned and then slowly, lasciviously, ran her tongue over the tip of my cock. "We can't have that, can we?" she said playfully. "Besides, I want it somewhere else ..."

She rolled alongside me and we kissed again, my free hand fondling her beautiful breasts, then slipping down to the top of her panties. Before I could slide it inside, she grabbed it and held it tight. Breaking from the kiss, she looked into my face, the smile gone, her expression once again intense. "Katy", she said softly, "I did say there was something I wanted to show you ..."

She guided my hand inside her panties and onto ... a lump. A meaty lump that throbbed under my touch ...

I snatched my hand back and gave her a startled look. She held my gaze steadily, almost defiantly. I heard a rustle as she pulled down her panties. She glanced downwards and I followed the look. Standing out proud from her lithe body was the last thing I could have expected to see. It was small, smaller even than mine, but no less erect. And unmistakeably a cock.

As I stared in consternation, Grace took my unresisting hand and gently guided it to her member.. As my fingers closed around the shaft it throbbed again. And so did I, as she transferred her hand to my own appendage.

"It's part of me", she breathed, "and you do want me ... don't you?"

For a second we were motionless. And then we were kissing passionately again, crushing our lips together, tongues moving urgently. And as if in a dream I felt my hand stroking her shaft, reaching down to the bottom to feel the tight skin of her hairless ballsack, as her hand roamed over me in turn.

Then, without any conscious decision, I was on top of her, still raining kisses on her cherry lips. And now our cocks were pressed together and both the hardness and softness of her were driving me wild. And I knew her excitement matched mine, when she gasped "Fuck me ... please, fuck me!"

Her words pulled me up short. I wanted to , but ... She must have understood my confusion, because she gestured frantically at a bedside cabinet. "In there, top drawer, lube ..."

Lifting myself off her, I scrabbled for the drawer she'd indicated and found of tube of lubricant. Turning back to the bed I found Grace on her back, legs drawn up, knees to her chest. "Give it to me", she called, motioning me back onto the bed. As I knelt in front of her, she ripped the top off the tube and squeezed out a generous dollop of viscous fluid. Reaching between her legs, she smeared it around her puckered anus, then pushed some inside.

Lifting her legs high she guided me into position, bringing me forward and over her. I paused for a minute, still struggling to take in what was happening, what we were doing, what we ... were.

And then my cock was moving irresistibly into place, pressing down against her exposed asshole. There was a brief moment of resistance and then need and desire drove me inside. It was so tight, tighter than the few vaginas I'd penetrated, and for a moment I was worried that I might hurt her. "You ok?" I asked, unable to keep the anxiety out of my voice.

She laughed then. "God, yes. I've wanted this since I first saw you in that schoolgirl outfit ..." Then her expression grew serious again. "Now just fuck me, ok?"

I started to thrust, slowly at first, then picking up speed as I opened her up and the lube did its work. As I did so, I started to go deeper, tentatively at first, then ramming down until I was slapping against her ass. I must have hit some kind of spot, because she let out a cry. "Oh god, yeah, right there, right there ..."

As I settled into a rhythm I leant forward and for a few moments alternated kissing her willing mouth and licking her nipples, all the while driving deep into her, or as deep as I could. I would periodically be rewarded with ecstatic moans as I hit that magic spot.

And then I looked down for the first time since entering her and was transfixed by what I saw. There was my cock, disappearing inside her back passage ... and there was hers, still fully hard, flat against her stomach. As I watched, she brought one hand up and began first to stroke it, then pump it, using the remnants of the lube in her palm.

The sight was erotic beyond belief and it drove me to fuck her even harder. And now her gasps were coming with almost every stroke, and I felt a pressure building inside, aching for release. It had been so long, and to have this gorgeous creature underneath me, her beautiful face twisted with lust and desire, her luscious breasts there for me to taste, her tight hole taking everything I could offer, her hard cock a blur as she wanked it furiously ...

It was nothing I could make sense of, I just existed in the now as I savoured the sight and sound of what we were doing, felt the sweet pressure on my rock-hard member, watched in amazement as hers erupted and spat streams of creamy white spunk over her belly and breasts.

And then I was coming too, in wave after wave, crying out with ecstasy and release as I emptied myself far inside her, the orgasm more intense than any I could remember. And then the sweetest sensation of all, locking into her shining eyes and seeing all my joy and desire perfectly mirrored, leaning down to kiss her tenderly, her lips soft and warm against mine ...

With a groan I lifted myself off her and collapsed beside her on the bed. For a moment I lay there panting, still feeling the aftershocks of my climax. And then, as if at some unspoken command, we turned towards one another and embraced, pressing our bodies together, heedless of the liquid remnants of our passion, our shrinking members gently touching as we kissed again.

Nothing was said. The questions, the explanations, they would come later. For now, there were no words, just bodies entwined, and at peace. After a while, we just lay in each other's arms, and as I listened to the sound of her breathing and took in her scent, I gradually slipped into a deep slumber ...

I had no idea what time it was when I awoke. I only knew I had been dreaming about Grace, about kissing her breasts, running my hands down her stockinged thighs, fondling her cock, feeling my own stiffen in response. And I realised that right now, not in a dream, but here in her apartment, on her bed, my cock was indeed coming alive under her gentle touch.

As I opened my eyes, I saw she was looking at me with a half-smile. She kissed me gently, then said playfully: "Oh, I'm sorry, did I wake you up?" While she said this, her hand became busier and I stiffened to full erection.

Without thinking, I reached down to find her own member. It was already hard, but leapt and throbbed under my touch. As I caressed it, my mouth found hers, and I marvelled again at how that combination of soft and hard flesh could so inflame my senses.

This time there was no desperate urgency in our lovemaking. We caressed and explored each other's bodies for what seemed like forever, before I took her doggie-style, slipping easily inside, my penetration greased by the remnants of my first, shattering climax. This time my strokes were long and leisurely. When I tried to pick up the pace and drive deeper to find whatever spot had so aroused her last time, she dissuaded me, content to move her rump in time to the slow and steady rhythm of my thrusting.

The orgasm this time was much longer to arrive and not so powerful, but no less sweet, as I arched my back and shot my load inside her, "Mmmmm", purred Grace happily as I slid out of her, "that's what I wanted, you filling me right up ..."

She got up off the bed and then squatted down on the floor. I watched, fascinated, as a steady stream of my cum dripped from her behind. She reached between her legs, caught some of it on her fingers, then licked them clean. She laughed when she saw my expression. "What? I just wanted to see what you tasted like ..."

Once again though, her face grew serious as she rose and stood by the side of the bed, gently stroking her stiff cock. She looked down at me and said softly: "My turn now - don't you think?"

In answer I swung my legs down and sat on the edge of the bed. She moved forward slightly to stand between my legs, her member jutting out towards me. I hesitated, but only for a second. She had given herself to me, utterly and completely. If she wanted this, I could not refuse her. Leaning forward, I took her into my mouth.

Until recently I would have gagged at the very idea of sucking a cock. But after weeks of Miss Everett forcing me to lick and suck a variety of dildos, most much bigger than what Grace was packing, I wasn't just used to it - I had some idea of what to do. So as I wrapped my lips around her meat I didn't just take part of her, I let the full length slip down my throat, going all the way to the base of her cock. I held her there for a few seconds, gagging slightly (I hadn't yet lost the reflex entirely), then released her.

I was rewarded with a long moan of appreciation. I ran my tongue a couple of times along the shaft, then used it to gently probe the glans. As I did, I looked up and asked: "Is this what you had in mind?"

Grace let out a long sigh of pleasure. "Oooooh, yes ..." She gently placed her hands on either side of my head and started moving it towards then away from her, so that her rock hard cock moved in and out of my mouth. I made an O with my lips and picked up the rhythm, careful to keep my teeth out of the way as I'd been taught (Miss Everett had spanked me unmercifully if she ever saw bite marks on her dildos).

It was just the way I'd experienced it in those lessons ... and yet totally different. Dildos, no matter how lifelike, were not warm, they didn't feel of flesh - and they definitely didn't twitch and throb. And the person holding them didn't react to every lick, every sudden squeeze of the lips. They didn't moan and gasp, they didn't start panting, their legs and hips didn't shake with arousal ...

I was sucking her faster now, or she was forcing me to, it didn't matter which. There was no subtle stimulation now, no teasing, no clever use of the tongue, just suction, the provision of a wet and willing hole into which to plunge her meaty sword. Reaching round behind her, I ran my hands up and down her nylon-clad legs, then grabbed her buttocks and started pulling her even harder into my mouth.

And now she was no longer moving my head, she was thrusting with her hips, spearing herself into me, fucking my face. I felt her whole body stiffen, every muscle tensing, and she cried out: "Oh fuck, yeah, Katy, that's it, that's it, just a little bit more, keep going, oh yeah, that's it ... oh fuuuuck ..."

And the living thing in my mouth bucked and spat, and I felt jet after jet of liquid hit the back of my throat. I swallowed convulsively, barely registering the salty taste as I gulped it down. And I would have pulled back then, but her hands held my head in place, as she pushed her jerking cock deep into my throat one last time. As her thrusts slowed and became shallower I opened my mouth and took a ragged breath.

And then, surprising myself, I closed my mouth over her again and sucked a little more, as I had seen girls do in porno clips, teasing the last drops of cum out and licking her cock clean. And I felt a surge of ...

For a minute I wasn't sure what emotion I was feeling. And then I realised with a shock that it was pride. I had brought her to orgasm with my mouth, sucked her off and swallowed every last drop. And as I looked down, I saw that I was already hard again ...