Note: This story was dynamically reformatted for online reading convenience. Big Issue Boy: by (c) Hamilton Joyce (My 100th ASSTR story features the feminisation of a boy). Mm 'Big Issue, Mister. Big Issue, sir.' Usually I just ignore them, no eye contact, nothing, and I had already been solicited twice in the two hundred yards between the restaurant and my car. I had my umbrella up, which was another reason for just walking past. 'Big Issue.' However, there was something about this boy, who seemed young to be selling the street magazine. He looked no older than fourteen, but he must have been sixteen or the organisers of the rag would not have allowed him to hawk it. And he was undeniably pretty: dirty and scruffy yes, but I have an artist's eye and I know beauty when I see it even when it is masked by the grime of street-sleeping and tatty, worn-out clothes. He was blonde, and had near-shoulder-length hair, in rat-tails because of the rain and greasy, unwashed. He had the blonde's typical complexion, clear and sun-tanned, blue eyes, and surprisingly white teeth. His lips were full and sensuous. I doubted if he had to shave much yet, if at all. He was slight and not much more than five foot three or four I should think, slender arms and his legs looked long and slim in too-brief shorts. He was sheltering in the doorway of Lloyds Bank, but had been in the rain, and his grubby t-Shirt, once white but now grey, had become damp and showed his nipples very clearly. Those shorts, faded denim and torn at the leg, were too tight as well. They were frayed at the groin and a tantalising glimpse of pink flesh resulted and stopped me in my tracks . You could tell by the clear, unblemished skin on his arms and legs that if he was into drugs, at least he was not main-lining. He had great potential, and my photographer's eye took that in immediately. A boy, still, but with something of the feminine about him, even in his voice and his smile as I took a coin from my pocket. 'Thank you, mister.' The voice was accentless, and I guessed he had seen better times, a middle-class lad come up to the city to find the good life, and finding it a great deal tougher than he had expected. I wondered if he had yet started selling his young body to the men who would appreciate it. I doubted it: he would have been cleaner and better dressed if he had started working as a rent boy. That would come, doubtless. I shoved the magazine in my pocket and turned to walk away. On an after-thought, I turned again and handed him a card from my pocket. 'You can keep the change...' In fact he had not offered me the ten pence change. 'But if you want to earn some real money, call me on that number.' I saw him stuff the card into his hip pocket. 'Big Issue....' I turned the corner, and threw the mag into a bin. ........................................................................ I am a photographer, but six years ago, as soon as I saw where the internet was leading, I started to set up web sites....pay for porn. I produce my own photosets and videos, and some of my models are eager amateurs I don't have to pay. Others I pay. But all in all it's a very good living, and keeps me in some style. The filming is amusing as well! It was Sunday morning that the phone rang. The voice on the other end was hesitant, well-spoken but full of doubt. 'You said I could earn real money....' 'Fifty pounds and hour for about four hours.' 'What will I have to do?' I guessed he already knew or suspected what some of the duties would be! 'I will want you to dress up while I take some photographs, and then we have sex together and I take some more.' 'For four hours?' 'At least. May be more.' I didn't add that if he was good it could well be all night: I'm a randy old bugger and use viagra! There was a long silence: good, as the hesitation confirmed my guess that he was not yet a rent boy, might even be a virgin. Then, 'When do you want me?' 'Four o'clock. The address is on my card. Don't be late.' .......................................................... Because I too would figure in the photograph and video recording session, I had dressed myself in my dinner jacket, Rolex watch, cufflinks, pearl shirt buttons, the full gear! I am big built but fit and look good in formal dress. The doorbell rang at exactly four, and I guessed he had been early and waited outside as the hand on his cheap watch moved round. Good! I wanted an obedient lad tonight! But he looked a mess. It was still raining, as it had been for days, and he looked bedraggled as well as grimy, a real street urchin. I had him leave his trainers at the door. 'First you are to take a bath. Wash your hair too.' I touched his face with my hand. 'And you may as well have a shave, though there's not much hair is there? There's an electric razor in the cabinet in the bathroom. When you've done use the hairdryer and come through wearing the bathrobe hanging on the door.' It took him the best part of an hour, but when he emerged he was transformed. Sexy before, he was devastating now. But I managed to keep my hands off him for the time being. The towel bathrobe was too big for him, and with his slender figure, blue eyes, and peaches-and-cream complexion he seemed very small and vulnerable. He would film well! 'Drink?' 'Please?' 'Wine, or vodka or scotch.' 'Uh, vodka, please. And coke if you've got some.' I poured him a triple vodka and topped the glass up with coke. A small whiskey for me. 'Cheers! And swallow one of these, too.' 'They viagra?' 'Sure. One each. The longer we go on the more you earn....' I had a quick look at my wristwatch. Ten to five, which meant the pill would trip in at about half-past five. Photo-session till then.... 'What's your name?' 'Terry.' 'I'm Mr McPherson. You've finished your drink. Another?' He had swallowed it in one! 'Please, Mr McPherson.' I poured him another triple and topped it up with coke. It would help if he was a bit tipsy when it came to the sex, and especially if he really was virgin. 'Get into these, Terry, and I'll set up the lights.' I switched a dimmer on the wall, and as the lights started to come on, so five hidden cameras whirred silently into action. Two were set to show different views of the room, one more was focussed on the settee, one was overhead, and one would follow any movement, periodically Zooming in and out. My final video for websites would involve cutting and editing, pasting bits from each camera into a whole film of the dressing, undressing, and sex with this boy. I enjoy watching a boy dress almost as much as stripping him. I was right about this one. He undid the belt on the bath-robe, and as it fell open my eyes were drawn to his midriff. Tanned all over with no tan-lines (must have been spending lots of time on our nudist beach sunny days), nice flat belly. And that cock, still not the weapon of an adult man but no longer a boy's, would look good on film. It was cut and very pretty, and with a fringe of hair at the base, a darker gold than the hair of his head, the slender shaft almost the same tanned colour as his belly. He was looking at the carpet unwilling to meet my eyes, which must have been full of lust. Good! a chaste and modest boy would film well and would be all the better for sex when the time came. He was shy and turned round, giving me a view of a sun-tanned bottom, slightly boyish and still a bit rounded and shapely, not quite the angularity of an adult male. I like finding teen boys, as they still have something of the feminine about them and make the sort of convincing transvestites my punters are willing to pay good money to see. I had sorted out a green satin basque, with white lace trim, matching thong and fully-fashioned black stockings, sexy Cuban-heeled and glossy. His trainers (ugh!) had told me he took size six, and I found sexy sandals, high-heeled, strappy and gold, to fit him. Over all would go a slinky, thigh length dress, itself in deep green silk. My professional models (trannies from the clubs mostly) always put on a basque, suspender-belt too, by fastening it up down the front, and then pulling it round their body so that the catches and loops are properly down the back. He tried to do it up arms reaching round the back: no good! I helped him into the basque, standing behind him and fastening the twenty or so little catches. I treated myself to a quick grope of that firm little bottom, nearly as tanned as his back. He flinched momentarily when I touched him, and my suspicion he was an innocent first-timer seemed confirmed. I felt my cock stiffening at the prospect. I had to show him how to use the breast forms, reaching over his shoulders to slip them down into the cups of his basque, and letting my cock touch his arse as I did so. He would not need a wig as, washed, dried and brushed his blonde hair hung to his shoulders, and shone, sexy and the most feminine thing about him. I finished fixing the last of the the lights as he put on the stockings, managing well with the clasps at the front, but failing again with those at the back. His seams were nice and straight, though, making his legs look very feminine, and I fastened the difficult clasps for him, rewarding myself again with a feel of his bottom, this time a bit deeper into the crack of his arse. I turned him round to face me, but still he would not meet my eyes. He was looking at my crotch where my bulge must have been evident I was sure, and his interest promised a rewarding evening for me, for both of us probably. He was hard too, and I guessed the girlie clothes were fulfilling a fantasy (I was sure he had not been secretly trying on mother's or sister's clothes like so many, perhaps most little boys. He would have been handier with the suspender clasps and the basque catches if he had indulged in a bit of closet cross-dressing. But his hard-on told me he was a natural transvestite. And his sideways looks at me told me he had gay desires too, probably bisexual. Or maybe not yet differentiated. In which case this Sunday afternoon might well sway him towards the homo as opposed to the hetero!) His bum was beautiful as he bent over to put on the high heeled shoes, and they did wonders for already sexy and feminine legs. He looked a bit unsure standing in them, but that would come.... 'Your complexion is so good, all you need is a dab of powder. Oh, and this of course.' I applied a sexy, tarty red lipstick. 'Don't lick your lips for a minute or two and it will set, non-smudge you see. There. Look at yourself in the mirror, Terry.' 'A girl fit for a millionaire. Very nice!' Like me, he was rock hard now, his cock making a tent in the shiny green silk. Without prompting he took up poses, admiring himself in the mirror. 'Now don't tell me, Terry, you've never dressed before. You're a natural.' 'Never. But these feel good.' He ran his hands up stockinged legs, and over his bottom, always looking in the long mirror. He walked across the room, looking over his shoulder and admiring himself. He seemed surprisingly steady in his high-heels now after only a few minutes. 'Well, slip this gown on, and you'll look the real thing.' The gown flowed over him, and he really did look like a young girl dressed for her first real evening out! A teenager at the High School Prom. 'Now you start earning that bread! Smile for the camera!' The smile was tentative and shy, but all the better for that, and I took a dozen of him in the gown from all angles, and even lounging on the white leather settee. As he got used to me the shyness began to lift, and I managed to make him laugh, getting some great shots, which I would use to start the photoset for my sites. I always start a photoset with posed "studio" type pictures, including close-ups of the face, showing how really feminine the tranny is. But we soon move on to sexier matters, and I had him lounging and showing lots of lovely, feminine leg, stocking tops and a bulge at the silken crotch. Then kneeling with the hem of the dress pulled up, stocking tops again and a hint of the pert bum. As well as my digital still camera, the video cameras would be getting all this, though I would only be using a minute or two to start the final film. Time, now, for some flesh. I had him unzip the back of his dress and hold it loose around his tits for a few pics, and then drop it to his ankles, in a pool of green silk. He was entering into the spirit now, and smiled as he shook the dress from around his ankles and took up a cheesecake pose. I zoomed in on tits, and then bulging crotch. Time for the dinner-jacketed fat-cat to enter the film. I left a couple of still cameras to click away, each every twenty seconds when I went over to join him as he sat now on the settee. I really ought to have a third guy here to take these pics I thought: these would probably do, with some freeze-frames from the videos but they might not be great. Old Mr Cohen would probly pay to be the photographer...that was a thought.... but he would be no good filmed, too old, fat and ugly! I stood so I was side-on to the cameras, and just in front of the pretty boy-girl. 'Unzip me, Terry, and take it out for me.' He was clumsy with the zip, and getting my hard cock out through the front of my boxer shorts, but that would look good on the video, showing he was not practised in it, innocent. 'I expect you know what men like their little girls to do, Terry?' 'I think so, Mr McPherson.' He was holding my cock in both hands, and he bent his lips towards it. I love that moment when a tranny closes her lip-sticked lips over my knob, and if she is young and pretty like this one it is heaven. I let him suck and lick me for a few minutes, but staying well short of coming. 'You can undress me now, Terry.' I have a good body as I have plenty of time to work out and enjoy my sessions at the gym. So I am muscular and a fat-free zone. Also I have my body completely waxed, so I am smooth. In fact years ago I had permanent electrolysis done on my "back, sack and crack" so the waxing is quite easy and non-painful! Anyway, I'm quite good enough to star in my own videos, which is amusing and also saves costs! I think he ....she!... was surprised I had tied my own bow-tie, but she pulled it undone, and went to work popping the dress-shirt buttons. I was amused as she tentatively treated herself to a quick feel of my pecs. I was right that this street arab was at least bisexual in orientation. 'It's all right, Terry, you're allowed to touch.' I laughed. She pulled my dress shirt loose from my cummerbund and laid it carefully on a chair with the tie. I could see her looking at me but with eyes that would not meet mine. She was still shy, and all the more desirable to me. I pulled her to me and kissed her, for myself as much as for the benefit of the cameras. My cock, sticking from my trousers, pressed against her and she wriggled as I fondled her bottom, hands caressing the tight satin. She started to undo the clips and belt at my waist, and then remembered she had to take off shoes and socks first. She knelt to do this, and before getting up again had graspped my cock once more, and swallowed the full length, looking up at me, and for the first time meeting my gaze directly. I could see the desire and pleasure in her blue eyes as she sucked and gobbled, tickling my balls as she sucked. I held her head for a second or two, fine blonde hair between my fingers, before I lifted her off me. It took only a moment for her to help me out of my trousers and shorts, and I was naked for the cameras. I turned, to give a good profile shot of my erect penis, and was confident one camera would have zoomed in on it as I shook it with my right hand so as not to obscure the shot. The lube was on the side-table, and I tore a packet open, greasing my cock. The tranny was so clearly a virgin that I did not bother with a condom; bare-backing her would be a rare treat for myself and for visitors to my website. 'Lay down, Terry.' I stood over her, looking down and rubbing the slippery lube up and down my cock. 'Take them off, your panties.' She was still hard, and her cock was very pretty. I promised myself a good long suck later. 'Don't hurt me. Please, Mr McPherson.' 'Your first time?' She nodded, eyes averted, shyly. 'I thought so. No, It won't hurt if you do as I say.' It would hurt of course: always does first time. But I would probably be able to make it "Hurt Good" just as Joshua, the Head Boy, had when he fucked me the first time, and me much younger than this boy. She was unresisting as I grasped her ankles, and bent her legs back over her, her arsehole coming into view: I thought I could hear a camera zooming in on the movement as I applied the residue of the silk-lube to the nice puckered rose. Her legs and bottom were deep-tanned, but between her thighs and in the very crease of her arse she was white and soft, her anus a lovely pink-brown, tight and inviting. I supported her legs on my shoulders savouring for a second the feel of the glossy nylon against my neck. Her arsehole glistened with the grease as I applied my knob to it. 'Push out, don't suck in. Push out as if you are taking a dump.' She turned her face sideways, averting her gaze from me, as I pushed and the knob slipped into her. There was a look of anguish on her face, but she did not protest or cry out. It might have been the thought of the pay giving her courage, but more likely she had been wanting this for a long age, but never daring to do it. I pushed again and my cock slipped easily into her until my body rested against her. I felt her anus contract, gripping me tightly for a second and then relaxing. She was still looking away as I started to fuck her with long, slow sweeps. After a bit I found I could rest my weight on her legs and on her belly, freeing my hands to feel her hard, enticing body. I pulled the straps of her basque down over her shoulders and her nipples were brown and hairless: as I fingered them they became hard little nuts between fingers and thumbs. Later I would suck these, I prOmised myself, yes and that cock and tight balls-sack. Her cock was stiffening again, and I knew I must be pressing the right spot inside her with each thrust. As I looked down a drop of cum appeared in the eye of her prick and ran down over the flaring helmet: yes, I would suck that too. She groaned involuntarily, and now it was with pleasure, or at least pleasure mixed with pain. I increased the pace and vigour of my thrusts, and her cock waved about between us. She reached down and started too masturbate, but I flicked her wrist with my hand and said "N0" very firmly. I did not want her to cum. That was for my mouth in a few minutes. And I did not want cum all over that basque: that would mean having to wash it before the next photo session with it. And these satin pretties are never quite the same once they have been washed. But I was not far from coming, and she was looking directly at me with a dreamy look in her eyes like a satisfied animal. Her hips were rising and falling everso slightly to meet mine. I knew she was enjoying it now, just as I had that first time so many years before. I think she knew I was coming without my saying so. Probably she could read the special look on my face, almost of pain, that the male has as he comes, or perhaps she could feel my cock swell just a bit more as the orgasm rose, or perhaps she could feel the first gush of hot cum inside her as I emptied my balls into her. It was good for me and I spurted four times, each with a spearing thrust deep within her before I had finished and eased off laying there unmoving again. Her anus finally expelled my cock, still half-hard. I got up and went over to the wash-basin in the corner of the room (this had been a bedroom before I converted it into a sort of video and photo studio). I rinsed my cock....no blood. Good, you never know with virgin boys: so no complications there! I dried myself on his bathrobe. 'Better clean yourself up too, Terry. Your arse will be a bit sticky!' I watched as he ran some hot water, soaped himself, and dried off, returning to the sofa. I knelt in front of him and ran my hands up slender legs to the soft flesh above his stocking tops. His cock was still not that of an adult, as long as some men's perhaps at about six inches but still not as broad as it would be in a few years' time. I kissed the fine fringe of blonde hair at its root, and another drop of precum appeared in the eye of a flaring, broad knob. I was glad the cock was cut, partly because it would make for good photos, and partly because I have a bit of a fetish for cut cocks on young teens....you don't get enough of them nowadays! I touched the droplet of clear liquid with the tip of my tongue, lifting it so a spider's web thread joined my tongue to his cock. I was thinking of him as a boy again as I took his knob between my lips and heard him give a sigh of contentment. While fucking him he had been my little girl! I lowered my head, and allowed the whole of his shaft to enter my mouth, till my lips rested on his belly. He held my head between the palms of his hand, holding me in place on his cock. But now I gave him a real professional blow-job, for which I am famous throughout the neighbourhood. You need to really love sucking cock to do it well, and I just love the feel of a cock in my mouth, and if there are nylon-stockinged legs and a satin basque for me to caress at the same time, then that is heaven. I did not expect it to last long, and it did not! His hips heaved and wriggled as I bobbed up and down on him, and then I heard him groan and my mouth was filled with the boy's cum. I guessed this was also the first time he had come in someone's mouth. His cock twitched and throbbed in my mouth as the orgasm passed, and I was careful not to make it sensitive. It was still hard and erect when I pulled back to sit beside him again. My cock was hard again as well! ................................................ I poured us another drink each, malt for me and vodka and coke for him, and we chatted a bit side-by-side on the couch. I found that I was right. He was a grammar school boy from Kent, one of the few places that still had that old-fashioned selective education system. He had done his 'A levels' a year early at sixteen and got good grades in english, history, french and latin. But the love of his life was drama and acting held all his ambitions. For years he had been the 'juvenile lead' in productions in the local repertory theatre, taking female as well as male roles, and enjoying the female parts even more than the male. He was going to university in September to study drama and hopefully get some more acting experience. He had come up to the city in the hope that he would find some theatre work before his drama studies began, but had not yet got his union card, which was why he was selling Big Issue as a stop-gap. I told him he made a really convincing girl, even with minimal grease-paint! He said it felt as natural as being male. 'Might be a first! I mean the first transvestite star actress!' 'There was always the great Sarah Bernhardt!' As we chatted I fondled him, and especially his cock and balls, now ensconced in satin again, and kept him nice and hard: the virility of a sixteen year-old, plus the little blue pill, and of course, he was enjoying this new feminine role. I was still hard and looking forward to enjoying him the way I like most, from behind. 'I want you again, Terry. Shall we?' 'Please, Mr McPherson, and this time I want to really remember it as it happens. The first time it was all so new and exciting it went by in a flash.' 'I'll make it last a bit longer this time, promise.' 'I didn't mean that... I mean...' He blushed with emarassment at his faux pas. I swear he blushed, and looked so lovely! 'I know what you mean, Terry, and I think it's sweet. Give me a kiss.' I felt his little cock in its green satin pouch, the soft inner thighs, and the glossy stocking tops as we embraced and his tongue explored my mouth. He was stroking my cock and I was soon rock-hard for him. I pulled his panties down (yet again!) and he raised his bottom so we could remove them completely. 'Now, Terry, on all fours with your head on the pillows.' He leaped to it! Knelt for me over the sofa his face in the velvet cushion. There was still a dribble of cum and lube between his arse cheeks, but to be safe I stroked some more lube over his anus and slid a finger in to make sure I penetrated easily for him. He wriggled his arse provocatively and I finger fucked him a few seconds, pressing against his prostate. 'Please....' I placed my knob and heard his groan of pleasure as I sank my shaft deep in him till my thighs were pressed against his tanned arse. His sighs and little squeaks were muffled by the pillow as I fucked him with long, slow sweeps at first, grasping his hips to control his movements beneath me. his back was bronzed and I thought the green satin was exactly right for his complexion. I stroked his back with the tips of my fingers and then leaned forward and kissed the back of his neck, where the blonde hair was finest. I was moving faster now, with short, stabbing thrusts, and a drop of sweat fell from my brow onto the green satin of his basque making an almost black spot. I reached for his panties on the floor beside us and mopped my brow, still fucking hard. It occurred to me that this was going to make a great video for my web customers: a stunning little tranny, me on good form, and real, enthusiastic fucking. I had slowed down to long, slow pushes while I thought about the cameras and Terry protested. 'Faster, Mr McPherson. Faster and harder. Please......' That suited my mood too, and I shagged that arse as thoroughly as ever arse was shagged! My thighs smacked hard into his bottom and I could hear his gasps with each penetration. I reached under him, and found his cock still hard. I gripped it and used it to control his movements, because he was flexing his back so his bottom rose to meet each thrust. His cock throbbed in my fist, and the whole effect was so sexy that, despite myself, I found I was coming, the tension rising from my own arse to my cock, and then spurting cum into him, one great gush with each of about four thrusts. I slowed now, enjoying the feeling of satisfaction, fucking slower and slower till we were still again. His arsehole expelled my cock, only half-hard now. Some cum dripped onto the carpet. I got up and went over to the sink to rinse off. No blood! He took his turn at the sink, and then sat beside me again on the sofa. 'That was wonderful! Great! I can't thank you enough!' 'I could tell you enjoyed it, Terry.' 'Oh yes!' There was a silence as I considered how satisfying it was to have awoken a young lad to the real nature of his sexuality. He was gay, and a cross-dresser. Lucky guy...or girl! 'How much have I earned?' I looked at my watch. 'Just over two hours...so that's a hundred and fifty.' 'I asked because I wondered if I could keep these clothes and shoes. I'll pay for them!' 'You're going to dress again, then?' 'I think I'll always dress as a girl from now on. It feels so good. And I look good, don't I?' He stood up and posed in the mirror again, pulling the panties on for the last time. 'You certainly look better in those than the dreadful stuff you arrived in'. He laughed. It may have been an illusion, but even the laugh had a feminine timbre now: of course he was a skilled actor...actress? 'And I'm feeling generous. I'm going to give you them for being such a good camera subject, and such a good fuck too.' His arms were round my neck and his lips on mine. I was very aware his cock was still hard, but to tell the truth I had enough, and was not really tempted to suck him off again. 'I've got a friend called Sir Joshua Sallah....' 'The guy who owns newspapers and race horses?' 'That's him. We were at school together and have stayed close. His steady girl Donna is a transvestite, but she has gone to New York to manage a night club, so he's on the loose a bit nowadays. I'd like you to meet him.' 'He's a very handsome man....' 'He is.' I was silent a moment as I remembered how Josh, two years older than me, had seduced me at school, and taught me the joys of gay sex. 'Yes he's certainly good-looking, and very, very generous. He can afford to be, of course. He'll be looking for a new little squeeze, and it could be good news for you, Terry, if you play your cards right. Fill your gap year in nicely, better than selling Big Issue at any rate.' That tinkling laugh again. 'I'd like that. I suppose he'll want to fill my gap too, like you just did. I hope so: you've really woken me up down there...' 'I'll give him a call then.' Terry listened to the half of the conversation he could hear.... 'Yes, Josh, blonde, tanned, slender, legal, and very pretty.....twice and she loved it.....yes, virgin, or at least was an hour ago, you know me!.....educated, articulate...yes, keen to meet you....half an hour, then.....' I went to the sideboard drawer and took out a little gold handbag I use as a film prop sometimes, counted out £150 and put it in the bag, handing it to Terry. 'He'll be here in a few minutes, and we'd better sort out your make-up. I've kissed some of the lipstick off even though it shouldn't. Powdered and lipsticked, and hair brushed again she looked the perfect teenage girl once more. We put the powder and lipstick in the handbag, and as she slipped into her gown I put three condoms in it as well. 'You won't want to use these with Sir Joshua, but sometimes he has rent-boys and lads he finds in bars. If you both go clubbing tonight he's quite likely to take one or two lads home with you. If one gets to fuck you, make sure he wears a condom, sweetie.' she kissed me again, and we went through to my proper reception room to wait for him. 'When Sir Joshua arrives, remember a lady never gets up to shake hands with a man when she's already sitting, and always "Sir Joshua" even though I call him "Josh". It was all very satifactory. I seldom want to have sex twice with the same person, whether girl, boy or cd. So all that was taken care of, and no doubt Josh would send me a nice present in the morning, probably a dozen of good wine...... ..............................................................