Note: This story was dynamically reformatted for online reading convenience. School Panto Prince and Princess by (c) Joyce Hamilton I was a pretty boy and always played female roles in school plays: it was a boys' grammar school and amateur dramatics was very much part of its culture. No girls of course, so there was a couple or so of us able and willing to transvestite in a good cause! I was a good actor (actress?) and usually got a leading role if there was one. The teachers used to look for plays without women in them... Morning Departure or that one about the submarine stuck at the bottom of the sea.....but there are not many of those I guess, so I was in some demand. My greatest triumph was as Katerina in The Taming of the Shrew but I was in the Lower Sixth by then, probably sixteen or seventeen. This story is much earlier: I was in the second form and probably only twelve and it was my first starring role, The Sleeping Beauty in the pantomime of that name. It is not a great part in most pantos because apart from the first scene and the last she is often wordlessly demure .... or asleep! However she has to be a "beauty" and able to dance, including a flashy waltz!. There's only one photo of me at twelve, standing on a bridge by a river, in tight little swimming trunks. It's black and white of course, but you can see I'm tanned and that I've been swimming in the river, with my over-long blonde hair plastered down by the wet. This would be the summer before the winter panto, and I had a body and a face to die for! There's a newspaper cutting of me in drag as Princess Aurora and I must say I must have been pretty enough to set a few hetero male hearts racing. I've tried to get a proper copy of that from the news-paper, but it was taken over by a large group some years back and all the files destroyed. Like most actors I'm vain, you see! The panto always had three performances....a matinee for the whole school to watch, and then two evening performances for the parents and people who liked to watch little boys dressing up.... The local press always went to the matinee, and always said nice things, deserved or not. Parents and pervs went to the others. My tale begins the first day of the Christmas holiday, which was one of those clear, cold, sunny days that are still such a delight. I had decided to go out on my bicycle, along the old tow-path and then across the heath on the "Green Lane", an old grassy drove-road. I had stopped to look at the view from Cogger's Pike when Jack Spalding came plodding up the hill in his sports kit. Jack had been my Prince Charming in the panto, and was also a prop forward in the school rugby first fifteen: like me he had got rave reviews from the so-friendly local rag! 'Hello Princess Aurora!' 'Hello Prince Phillip!' We both laughed at this poor joke.... Walt Disney had chosen that name for his film version as most Americans had heard of The Duke of Edinburgh, and the teacher who wrote our script found it amusing too. If you know about rugby, you know what a prop forward looks like. They are big, broad and very strong. At seventeen Jack was all of that, and already hairy too: his hooped rugby shirt was tight across a barrel chest, and immense, muscular thighs over-filled his white shorts. He was steaming in the cold air, I remember, and running on the spot to keep warm. 'That last scene of all, after the wedding, when we had to pretend to kiss..' 'Not to be forgotten, my Prince Charming.' He hesitated, and I could almost see his embarassment, but he gulped and managed to say what had obviously been on his mind. 'While we hugged and pretended, I wished we were kissing for real!' 'Oh Jack! So did I. So did I...and I knew you did too as I could feel your hard cock against me. My clothes were rather thin, and your tights too!' 'Well you were stiff too, Aurora!' We both laughed... or to be more precise he laughed and I giggled.... girlie you see. 'Let's do it for real, then! Bring your bike behind those bushes. There was still frost on the grass hidden from the track-way so we just stood and embraced, a proper, sexy, lovers' kiss, open-mouth to open-mouth, tongues touching and exploring inside. He was stiff, I was stiff. It was a lovely feeling. Then I felt his hand on my cock, unzipping me and pulling my little, but so-hard cock out. He rubbed it, and then amazingly dropped to his knees and took it in his mouth. Jack Spalding, alpha male, rugby prop forward.... a cock sucker! But it was delightful, and he put a lot of energy into moving his mouth back and forth, sucking and licking at the front of my cocklet. I could feel myself cumming: I had not much boy-juice at twelve but was sure he would not want it in his mouth. I tried to pull away. He held me tight, hands on my bottom and sucked even harder, faster. 'But I'm gonna cum!' A stifled 'Mmmmmm' was the only response and re-doubled action. So "what the fuck" I let myself cum. Moments later my first cummy kiss as we embraced again. 'Me now!' And I knelt, pulling his shorts right down. My arms round his lovely broad bottom, and his big, veiny cock stretching my jaw. He must have been on edge because it seemed only seconds after his knob passed my lips that my mouth was filled with his warm, silky-slippery cum. So much more than I could produce, and soooo sexy! An even cummier kiss after he had pulled his shorts up. 'That was great, Princess, but it's bloody cold.' 'I loved it, Prince, but it would be nicer in the warm!' 'Look! My parents go to their Bridge Night every Saturday, and they are out from seven till after eleven, always. Can you come round and we can do it properly, in comfort?' 'You're in Millfield Grove aren't you? 'Number five.' 'Seven o'clock it is then.' 'Make it ten past. See you then. Gotta go before I freeze. Training for the match.... we've got St Jude's Saturday afternoon.' 'I know.... I'll be along to watch my Prince!' ................................................ I had not wanked Friday night as I wanted a lot of spunk for Saturday, but had found it difficult to sleep as a result. Finally I did, and dreamed of a big, strong guy holding me in his arms, me being a tiny girlie-boy dressed as a medieval princess! We beat St Jude's, and my guy had a great match, but I had a moment of panic when our coach came rushing over to treat him. But it was nothing serious... just a knock... and the match went on. He waved at me after the game and I waved back, my heart beating. I thought of Princesses and Knights in their jousts... daft little-boy fantasy but I was like that back then. I had told my mother I was going to play chess with a friend, and would come back when the contest was over.... but by 10 o'clock latest. So there was more than enough time for us to play a very different game! It was dark of course, and just as I was walking down the leafy road peering at the house numbers a car pulled out of the drive of number five. OK to go in! Can you remember the feeling of excitement when you were very young and looking forward to love-making? If you can't you've missed a lot and I'll tell you there is a tightness in the chest, and the heart beats so loud you think people will hear it: a pulse beats at the side of your head. Some people say this is "love". It aint! It's sexual excitement and is usually accompanied in males by a hard cock. Also there was a sudden moment of doubt: that cock-sucking had been spur of the moment, the sort of thing that any randy guy might do. But this was planned and different. I had the feeling that it would mean I really was gay as I suspected. But I honestly knew I was gay, didn't I? I mostly imagined men when I was wanking and my best jerk-off pictures were all strong men. When the other boys giggled over air-brushed photos of naked women in "Health And Efficiency" and suchlike mags I pretended to be interested.... if I could even be bothered to pretend. So I waverered and hesitated, but finally walked up the steps: it was a bit like the first dive into a swimming pool, a sudden brave decision, scary, but easy ever after the first! I had all these symptoms as I rang the doorbell. Jack opened it. And quickly closed it behind me. The house struck me as super-heated, especially after the winter air outside, but much hotter even than my own house. I was grateful when Jack helped me off with my overcoat, jacket and sweater. I could see why he was bare-footed and had only shorts and a tight sweat shirt that showed off his biceps and pecs. "Sod it!" I thought. "If he can so can I," and I took off my shoes and socks there in the hall. The slate floor was heated: my first encounter with under-floor heating: very posh! I stood alone a moment only, because we kissed. It was as good as the first two kisses, if less flavoured by boy-juice! Jack smelled of lemons: he must have showered and washed his hair in scented shampoo. The kiss could have lasted for ever as far as I was concerned, especially as we had our arms round each other, hands on the others' bottoms. 'Let's go straight up to my room, Peter.' 'You can call me Aurora if you like: I like that from you, Jack.' 'But only from me?' 'Mm.' ......................................... So Aurora and her Prince lay on his bed where he had draped the duvet over the foot of the bed so there was just an expanse of white sheet and two pillows. This kiss lasted much longer and our caresses were more explorative! As we writhed and pressed together I could feel his hard cock and I expect he could feel mine too. I felt him undoing the buttons on my white poplin shirt and then his hand inside stroking my chest, fingering my nipples. I felt free now to slide a hand up under his t-shirt. I was momentarily disappointed to find he had no hair on his chest, not like his massive legs and arms, but that disappointment was soon replaced by lust as I felt the flesh of his chest, big, strong pecs: I longed to se them. To kiss them.... He pulled his t-shirt off and I did the same with mine. Now we kissed half-naked and it was doubly interesting for our hands to caress warm, smooth flesh! I had never felt muscles like those of his biceps and shoulders.... Now Jack's tongue was in my ear.... I never knew till then this could be an erogenous zone.... and then his lips on my neck, my chest, and finally he was mouthing a nipple. I knew this as an erogenous zone and had been pulling at my nipples when jerking my little cock for several weeks since I found out about them! But the feeling had never been as powerful as this, sucking, nibbling, kissing. I wanted to do the same for him, for those muscular pecs almost as defined as a young girl's breasts but harder, firmer, muscle not flesh. I interrupted his nibbling and repeated exaxctly the same to him.... tongue in ear tasting the bitterness there, then kissing his neck, his chest, and lastly mouthing his nipple. He groaned, and I felt his hand on my cock through my trousers: I had taken my y-fronts off before leaving home in the sure knowledge they would not be needed this evening..... I felt for his cock.... not difficult to find! 'Naked. Let's get naked!' I was as keen to see Jack nude as he was to see me, and we both tore at our trousers and flung them on the floor. Neither of us was wearing underpants: I realised with satisfaction that like me Jack had been looking forweard to this escapade, planning and preparing for it. Duvet on the end of the bed leaving it clear, no underpants: he was as keen as me! We stopped everything and just looked at each other. I could see a glint in his eye, and he must have seen me looking at his cock, so briefly seen at Coggers Pike, and now admiring the "treasure trail" of black hair in a line up his belly as far as his navel. This and the bush around his cock and balls quite made up for the lack of chest hair in my opinion. He was manly, noble, even beautiful in a stocky muscular way. Me first this time! I turned round quickly on the bed and snuggled my face up against his crotch, pointing my tongue to lick his so-hairy balls. I was about a foot shorter than Jack but he managed to contort himself so his face was in my crotch and I felt his tongue on my hairless balls. We hugged each other close, but not so close that I could not get my lips to his cock and allow the cock-head to slide between them so I was again sucking his cock. I felt the warmth and wetness of his mouth around my cock, and his hands on my bottom: I was laying on one of his arms but supposed I was light enough and he strong enough not to care. I felt his broad, hard bottom, but was more interested in caressing his hairy thighs. So we re-invented the sixty nine, mouths sucking and licking, hands caressing and fondling. He came first and for the second time in my young life I tasted spunk, so much this time that I nearly gagged as it spurted against my palate and even into my throat. Nearly, but not quite as I swallowed joyfully. And came! There probably was not more than a tiny spurt of thin boy-juice, but it was a big orgasm for me and Jack must have enjoyed it as he immediately turned on the bed, hugged me, kissed me on my cummy lips and told be what a little angel I was. I was proud! And happy! And knew I really was gay! And sod it! I liked being gay! More than half my pleasure was the knowledge that Jack was happy with me. ................................................... I was surprised a hyper-fit guy like Jack would smoke, but it suited me: I had not many vices.... one more than a week ago I guess.... but had been smoking secretly for years. It was cozy and pleasant laying propped against the bedhead, his arm around my shoulders, my hand resting on an oh-so-sexy thigh as we shared the same cigarette and chatted. 'I know I'm gay now, Jack.' 'I'm glad you are, my angel. And I'm glad you're so sure. I feel gay when I'm with you, but honestly I did not notice boys much till I saw you as Princess Aurora, danced with you and held you in my arms. I certainly fancy you now... feel that!' He took my hand and placed it on his hard-again cock. Mine had never gone soft after I came. 'Did you wear knickers and stockings under your dress? I was wondering when I thought about you later......' 'No. Just my y-fronts.' 'But you'd have liked to?' 'Oh yes!' 'I know where there's some you can try on, and then we can come back to bed for some more....' He stubbed out the cigarette butt. ............................................................... The laundry basket was in the bathroom, and Jack tipped it up, emptying it onto the floor. The emerald green knickers stood out from the rest, as did the black stockings. He draped them over the stool and put the rest back. 'Here, Princess Aurora, slip these on!' He held them as I stepped into them and then slowly pulled them up over my thighs till they were right, cradling my balls for a second, a fondle through the satin to make sure they were tight into my crotch. I could see myself in the long mirror.... the tent at the front spoiled the effect a bit for me.... but not for Jack, I thought. He sat me on the stool and had me stretch out one leg and then the other while he put the stockings on me. They were glossy and had black seams. They felt even sexier encasing my legs than the knickers, and I rubbed my legs together to get the feel. 'That feels so good on my bum and round my bits!' 'Looks good. What's your shoe size?' 'Six.' 'That's lucky!' He held my hand and we went into another bedroom..... you could see it was his parents'. There was a row of shoes inside the sliding door of a wardrobe, one of them hih heeled shoes with silver straps. I sat on the bed while he put them on me. 'Just this and you'll be a lovely girlie-boy again. Better than Aurora in her grease paint. Purse your lips. I've seen them do this dozens of times.' The lipstick was a bright scarlet.... 'Now look at us in the mirror....' One of the wardrobe doors was a long mirror and we stood in front. I saw a big hulking male, and a pretty, half-naked girl. I was astonished how feminine my legs looked in those stockings and especially the high heels.These were a bit difficult to stand up in let alone walk in, but I felt so sexy. I half turned round and caressed my bottom... the green satin was quite tight across my buns and they really did look girlie: it felt so right too as I felt my balls and my cock through the knickers. This was the moment, I suppose, that a life-long transvestite was created! My hair was right too.... or nearly. My mum wamted me to have it cut short again but I was already resisting: it was not yet really long enough for a full pony tail which is what I wanted. There was nothing wrong with long hair now: lots of boys had it including rock-idols and footballers. And it would be nice to have shoulder-length, shining blonde hair to go with my peaches-and-cream complexion and ruby red lips! A pont tail was just about acceptable at school..... I put my arms around him, his cock sticking into my belly, and we kissed, Prince Phillip and Princess Aurora again! He picked me up bodily and carried me back to his own bedroom. He was so strong and manly my heart fluttered with excitement..... ................................................ On the bed again he wanted me to lay on my belly. I luxuriated in his almost worshipping attentions as he ran a finger nail down the length of my back, making me shiver .... Then I felt his face nuzzling my buttocks and it was clear he liked me in satin too! But he drew my knickers down till they got caught up in the stiletto heels of my shoes. He managed to untangle them and I felt his hands running up the seams of my stockings, both legs at once, and then his lips on my naked buttocks. 'I thought you wanted me in knickers, Jack!' 'Oh I did, Princess. But I wanted so much to kiss your cute bottom..... since our first fake kiss in the panto.' He must have liked my bum because of what he did next. As I lay there, eyes closed and enjoying these new caresses, I felt strong hands pull my buttocks apart and then amazingly his lips on my arsehole. He was kissing my arsehole! 'Oh no, Jack.......' But he did not stop. And then I felt the tip of his tongue go right in, and tickle up the rim of my hole. It was good, of course! I kept quiet and let him do it..... too good to protest! 'Was that nice, Princess?' 'Oh yes! Don't stop!' I don't know how long the rimming went on as I was almost hypnotised by it, but finally he stopped and I felt him drip something onto my buttocks. For a second I thought it was his pre-cum but then his hands again, slippery this time. Massage! 'I use this oil for wanking, my little Princess, but it makes a lovely massage-oil too.' Round and round my buttocks his hands pressed, fondled, caressed, sometimes straying up my back, but always returning to my bum. More and more his fingers slid into my bum crease, pressing against the place he had just been licking and kissing. And then his finger slid right up me, right up my bottom! 'Oh no, Jack!....' 'Just wait and see. You'll love it, my Princess!' So I lay quiet, submitting like a good little sissy-boy, and then it happened. He found the right place.... 'Oooh! That's nice!' 'Ah!' And it just got better and better until..... 'I'm going to cum! Oh yes! Yes!.....' My cock was still twitching as he turned me on my right side and bent my top leg. I felt his body pressed against me, his cock in my bum-crease. The knob was pushing against my arsehole and it felt good. Then he shoved with his hips, strong hands holding my body still...... and his knob forced its way into me. I screamed. 'You'll love this too, Princess, when your bum gets used to it. Be brave a minute or two.' I bit the pillow in the traditional way of the first fucking, as he slid the whole length of his cock up me, pulled it out as far as his knob, and then in again. We were fucking.... And gradually the first discomfort went and I started to feel the same strange pleasure his fingers had given me. 'I like that now, Jack.' That must have been his cue because he speeded up and the thrusts became more powerful. I felt him reach over me, hold my cock, and then start to wank it in time with his pushes. 'I'm gonna cum again, Jack. Oh! Jeez!' I knew he was coming too as his cock went even faster in and out and then slower with several fierce thrusts, and I imagined each one leading to a gusher of white cum inside me. I had loved it, as he said I would, and I wanted more, and more, and more..... The moment when a passive "bottom" was born, I guess..... Jack's Story I suppose if we had not met that winter's morning up on the Moors I would just have lived with an occasional fantasy of sex with a pretty young boy in girlie clothes without taking it any further, and my life would be very different..... much more respectable but frustrating and boring! It was the day after the pantomime, and a couple of days before the annual match with St Jude's, the school's derby match. I was keen to be superfit for the most important match of our season and went out for a morning training run every day: I enjoy stretching my body, asking it to perform better and better, and had a rigorous training regime. However, my sleep pattern had been disturbed by little Peter Farleigh, the Princess Aurora to my Prince Charming in the panto: that kiss on-stage had been feigned..... no mouth contact.... but the hugging embrace had been real enough to give me a hard-on. Good job my short doublet covered the top of my white tights and hid the bulge! Oh, and Princess Aurora had a hard on too: I could feel it through her dress and my tights. I jerked off several times the next few nights thinking about him (her?) and what I would like to do with her (to her?), but was still obsessed by that slender male-female body in my arms and the thought of a hard little cock and hairless balls. I had always considered myself heterosexual, though I had never had a girl friend and only briefly snogged a girl at a party. My hands had never felt a naked breast or pussy! My life had been the school (boys only), sport (maculine), and my mates (all guys). When I jerked off it was to fantasies and images of women.... but that was the end of my involvement with the other sex. And here I was with a Second Year boy filling my mind night and day! Perhaps I was bi? Or even gay? I suppressed this disturbing idea with the comforting thought that dressed as Princess Aurora he was prettier than most girls I knew, and far sexier! And if I was gay I would not like him girlie. Would I? But what about those thoughts of cock and hairless balls??? As I ran up Coggers Pike that morning my mind full of this adolescent nonsense, there he was with his bike. Fate! It was cold and I was running on the spot to keep warmed up, but it was obvious to chat about the success of the panto. Obvious, but not easy for me to tell him how aroused I had been by our embrace in the last scene, me in my tights and doublet, he in a lovely white wedding dress, how enjoyable the waltz had been, his young body against mine, his legs between mine so often.... And the feigned kiss.... how I had wanted it to be real, for our lips to touch. But I stammered it all out. Beyond hope, he felt the same and we went behind some rocks and bushes out of sight of the track. We embraced and this time kissed, properly with our mouths open, tongues meeting, entering. Despite the cold my cock was hard and I could feel his as our bodies pressed together. I reached down and felt his cock, and then with an un-thought impulse knelt in fron of him on the frozen grass and unzipped ..... He was wearing tight, white underpants, but I found the way in and pulled his cock out. It was soooo sexy, not as thin as I expected, and all the better for that, but quite short, very white, and with a pretty little pink knob just peeping out from his foreskin. I rolled the skin down and put the whole in my mouth. Apart from masturbation this was my first ever sex act, and it was delightful. Shortlived, though, as he came almost immediately and I tasted cum in my mouth for the first time, not much I guessed, but exciting all the same. I did not even have to ask him as he knelt in front of me and treated me to the same. I might have doubts as to whether I was gay....after all he was quite a feminine boy. But Peter must be gay I thought, wanting to suck a great big cock, to service a big, hairy-arsed rugby-playing male. I held his head, the blonde hair slipping between my frost-dry palms as his mouth bobbed up and down on my cock. I moved my hips, shagging those pretty, ruby lips and soon came. Our kiss was cummy and sexy, but it was too cold to linger. We had a date for Saturday evening when my parents always go out, and both of us knew what we wanted from that meeting! ......................................................................... I had been tense all day, my cock usually misbehaving, straining against my jeans. I had not wanked Friday night wanting to be on form for what I planned as a crash-course in gay sex.... for me as much as for the boy. In fact all the week I had been dreaming about him at night, despite jerking off thinking about what I wanted us to do together, despite unloading again in the morning before getting up. And my dreams had not been of a boy in drag.... they had been memories of younger days when I had so often seen my classmates nude in the showers. I knew how Peter would look naked, and was desperate to see his body, to have his smooth skin under my hands and my lips. These fantasies were stronger than any I had known before the panto.... usually of girls.... and I knew they were the real thing. I was certainly bi and possibly gay. This was a bit worrying, but I just knew I wanted him as my sex-partner and was going to have him. He wanted it too, so sod it! Saturday evening I showered and washed my hair, and wondered if I should wait for him naked, open the door and his first sight would be my erect penis. I decided this might scare him off.... though I doubted it.... so be safe and just dress as usual.... no underpants, though, for a quick release! The minutes between half-past six and ten past seven seemed to take hours as I had that tightness in my chest, slight dizziness, and above all straining cock, symptoms I still feel sometimes when "in love" with a new partner. I suspect this first was the most powerful excitement of all, though. I did not dare touch my cock, which was "edging" untouched! Finally the doorbell rang... He had a shy smile as I took his coat and hung it up, and then we kissed. I could feel him hard! I certainly was. He took off his shoes and socks, strange but clearly he knew we were going to bed. I carried him upstairs, showing off my fitness, though he really was no weight at all. On the bed we kissed again and I took his shirt off. He still had some remnants of the summer tan, his hairless chest a sort of golden colour and his nipples pinky brown. He had his hands up my t-shirt and was fondling my nipples; I pulled my shirt off and we embraced naked chest to naked chest, me reaching between us to grasp his cock. I said we should get naked, and we did. I was momentarily disappointed that he had not got his little-boy white y-fronts on, but then realised that he, like me, had not worn them to make the stripping easier and quicker. And he was lovely, so lovely that I stared at him in silence a long moment. He had that blonde peaches and cream complexion and full red lips you only find in young girls and boys, and that they lose some time into puberty. he still had that innocent, blue-eyed look of an angelic child, and his blonde hair was still Princess Aurora pantomime-long. I've described his hairless chest and nipples, but the same golden tan coloured his thighs, though you could see tan lines on his hips and lower belly, but this was decorated by a tiny triangle of fine first-hair, almost as blonde as his head, but perhaps just a bit more golden. I was so pleased that his balls were still hairless in their crinkly white sack.....so small and delicate. I had already seen his cock, but only the bit that could stick out from his flies: it was longer and certainly broader than I had expected, and as stiff as a rod of white marble, except for the little tip of his knob that peeped out from foreskin. It was a very beautiful, straight cocklet, and perhaps average for a boy of twelve, though I had imagined it smaller. He was studying me as well. I think I said he was beautiful. Whatever I said, he gave me that shy smile, and blushed. Then he turned round on the bed and nuzzled my cock and balls..... before I had so much as touched his. He was as keen as me, the twelve year old novice as keen as the seventeen year old..... equally novice to be honest! We sucked each other, wordless. I was so excited by the cock in my mouth, by the feel of his bottom, and his hands on my bottom that I came first, I'm sure filling his mouth with even more cum than our first time in the cold of The Moors. He came moments later. Our kisses after were doubly cummy! .............................................................. He was still hard, but I was not. Oh to be twelve again and repeat, repeat, repeat! We shared a cigarette and I talked to him about the panto, asking him if they had made him wear proper lingerie under the wedding dress. They had not, but he wished they had.... I tempted him with my mother's from the laundry basket, and helped him into green satin french knickers and seamed holdups. My cock was stiffening! We were lucky that he took the same size shoes as mother and I did up the buckles on a pair of silver high heels that made his legs look really feminine, and to me incredibly sexy. I was careful to remember exactly where I should put them back later! and we went back to bed.... he had no difficulty walking in the high heels and looked so cute! I realised how much more feminine the boy's legs looked in high heels....those trim little ankles, and of course the seamed stockings making already smooth legs look so glossy and soooo long. We lay on the bed and after a lovely snog, my leg between his and feeling the hard-silkiness, after that long embrace I lay aside and looked at him, committing this image to my memory. How nice it would have been to have a photo of him like this: but how dangerous! I wanted to see his back and turned him over on his belly. There were fine hairs at the nape of his neck, ash blonde and not golden like his pubic hair; I leaned over and kissed him there, hands feeling the smooth skin of his shoulders. His back was summer-golden and without blemish. I ran my finger nail from his neck down to the waistband of my mother's knickers. He shivered but told me he liked it, so I did it again and then the same with the tip of my tongue. I caresssed his buttocks through the green satin and sexy as that was I still wanted to see his naked bottom. I drew the knickers down to his thighs and his bum was so white compared with the gold of his back and the black of his stockings. 'I thought you liked me in panties....' He was giggling, enjoying being an object of male lust. 'But your bum is so cute, sexy.' I pulled the knickers right down , getting caught up a moment in the high heels. I thought about taking his shoes off too, but those ankles were so trim and sexy like this. I prised his legs open a bit and ran my hands up his stockings, the seams leading my hands up towards the so-desirable bum. I lingered at the stocking-tops.... the skin here was so silky and smooth, and nearly white like his bum. I kissed him there and felt his legs open just a tad wider for me. One hand on each firm little buttock I parted his crease and for the first time feasted my eyes on his arsehole, tight closed of course and looking so tender and innocent, like some little flower, pink-petalled. It was so pretty I had to kiss it, though if you were to ask me if I would like to kiss an anus a month ago I would have been horrified. My lips on his most secret place he started to protest, but as I licked with the point of my tongue, feeling round and round the lovely rose, sometimes straying into his arse-crease, but always returning to the spot, then he went quiet and finally begged me not to stop. I penetrated with the tip of my tongue and felt the firm little muscles holding it. So, holding his bum apart I rimmed him for several delicious minutes, and my mind was getting more and more eager for real penetration. I got my baby oil I kept hidden in the drawer of the bedside cabinet and squirted a few drops onto his buttocks, and then as a second thought onto my cock. 'I keep this oil so I don't get sore when I jerk off.' 'Good idea! I get sore sometimes too if I do it too much.' 'Can't do it too much, Princess....' He giggled and wriggled his bum as I massaged his buttocks: my hands slipped when I tried to hold them apart, but it felt great as I caressed and fondled round and round, sometimes straying up to his back but always returning to his cute arse. More and more I put my hand into his arse crease and rubbed there with oily fingers. He particularly liked it when I pressed on his anus, but protested when I slid two fingers up into it. I reassured him and told him he would like it in a moment, hoping he would! I had read about the prostate, where it was and how to massage it, but my knowledge was completely theoretical. Now I would have to put theory into practise. It worked! He told me it was good! I stroked his back and bum with one hand as I finger-fucked him with the other and very soon... 'I'm gonna cum. I never knew.... Ah! Jeez!' I didn't stop. 'Still good?' 'Fuck yes!' 'Let's try this then: it's supposed to be even better. I lay him over on his right side with his left leg bent over so his anus was available to me, but also his cock. I lay up aginst him, my own cock nestling between the slippery halves of his bum, my hand on his cock, still erect. I pushed and my cock slid in where the way had been prepared by my fingers. 'No! That hurts, Jack!' 'Only for a minute and then it will be good.' It was certainly good for me as that sudden grip on my cock relaxed and I was able to slide right in till my pubic bush touched his smooth bottom, pull out as far as my knob, push in again and we were fucking. 'I don't think you're pressing on the right place, Jack: not like you were with your fingers.' I thought about it a moment, remembered the diagram I'd seen on-line and shifted a but higher up his back. 'Ooh! That's it. Jack! Ooooh yes!' So we fucked, me wanking his cock with my oily fist in the same rhythm as my cock. I promised myself that I would not cum till he had a third time. It took all my self control as I kept saying to myself "I'm buggering a beautiful teenage boy and he's enjoying it": but somehow I managed and finally with muttered endearments, panting, little-boy oaths he came.... just a wee bit of boy-juice on my fist this time. I came as well just as his bottom contracted and relaxed on my cock. I'm sure I must have pumped at least three great gushers of cum into him I was so excited. ....................................................................... There was still some time before he had to leave but we were a bit messy and needed a shower .( I still had not learned abot anal douches, and it was several months before I did and bought him one, showing him how to use it before visiting me). The shower was fun, but we had both had enough for the evening and just sat watching stupid tv till it was time for him to go. We had a proper good-night kiss, though! As I lay awake late, not able to sleep, I decided to spend some of my savings on lingerie for him.....at least some knickers, a suspender belt and stockings. Mother's knickers that fitted him were marked size 8-10. The women's department store would be easier than that lingerie boutique..... but the boutique probably had sexier stuff.... I would have to steel myself to go in! It would be worth it!. I suspected shoes would be expensive but if I could find some sexy size 6 shoes in a charity shop, that too.... if not there was always mother's. I must take measurements next Satuurdy as he would look great in a basque.... Shit! I needed to wank again....... The End for now at least.