Teddy's Story

By SusanEngland

Original link: https://www.lushstories.com/stories/gay-male/teddys-story.aspx

Tags: gay, anal, woman, fuck, cum

Added: 18 Mar 2007 Views: 17418 Avg Score: 4.38

A young man is sedcued by an older man. The man's sister teaches him to love a female
This story was a finalist in the Short Story Category of the ASSTR Golden Clitorides Awards 2005

I was challenged by my husband to write a Male/male story instead of my more usual female oriented stories. This is my attempt and I stress that it is simply a story. There is no basis in fact and the characters are fictitious.All characters are of course of an age to comply with the requirements of Lushstories.com.

What is true is that my grandfather was born in 1900 and was too young for WW1 and too old for WW2. The setting for this first attempt by me to write a gay story is true – Grandpa was an Air Raid Warden, there were Social Clubs for working men. The ‘Blue Lagoon’ really did exist. He has talked of it and laughed about it many times. The dress code for boys was as I have described and there were elasticated ‘snake head’ belts for the boys.


My husband says my story is too feminine and romantic in its descriptions and I must “try harder.” Oh dear, ‘bottom’ of the class again !! If you find it so then I apologise. Feedback would be very helpful.


Teddy's Story


Preface

I am bi-sexual, although my family doesn’t know of it.
My name is Edward, Teddy for my family and friends.



I was born in 1932 and recently celebrated my 72nd birthday. I am very happily married. My wife of 49 years standing is my best friend as well as a woman I have loved since we first met. We have had four children, 2 boys and two girls (who don’t come into this tale), but I have had occasional interests with both males and females over the years.



My earliest experience was with a mature man. I very much enjoyed it, but thanks to the intervention of an understanding female it failed to lock me in a world of homosexual loving. Because of her I was able to experience and enjoy heterosexual love and sex, and I’ve I decided to set down how this came about. I have tried to tell the story with the innocence of wording and expression that I had at the time



Chapter One – Uncle Reg takes me as his friend.



In England back then immediately after the war it was safe for youngsters to be out late. Looking back I never remember hearing that children had been abducted, or raped or murdered as they are today. I was never warned, as parents must warn today, that there were evil men who would harm us, and that we must be suspicious of anyone we didn't know, that we must not talk to strangers, that under no circumstances were we to go with them, anywhere, at any time, day or evening.



 



I now know that men who got pleasure from a sexual relationship with a young person were careful to be friendly, especially to be friendly with parents. They were gentle. They knew that if they made certain cautious advances they would be rejected by most, but the advance wasn't such that it could interpreted as 'abuse' in today's sense. With the right response from the youngster, they knew that they could slowly take the relationship further until they had a willing, perhaps enthusiastic, partner.



 



Dad was a blue-collar worker for a large public utility company. The firm provided many benefits ‑ access to libraries, sports grounds, athletic tracks and not least, a clubhouse for employees. The club had in addition to a bar, dartboards, card tables, tabletop skittles and such like. In a separate room were two snooker/billiards tables. In the days after the war and before TV, this was an important social centre, and there were many teams, male and female, which competed in various sporting leagues.



 



My name is Edward – Teddy – and at that time I was small for my age, only 5’ 3”tall. My hair was brown and cut ‘short back and sides’ in the style of the time and my eyes were blue.  I was slim and to my embarrassment, had what were called delicate features. Women would call me a ‘lovely boy to look at’ and some would say ‘isn’t he pretty?’



 



I had an older brother, Fred, aged 22 who was in the navy, and an older sister ‑ Margaret aged 20. Our home was in a terrace of working class houses and had three bedrooms, identical to all the rest of the houses in the neighbouring streets. There was no bathroom; a zinc bath was put in front of the fire during cold weather and laboriously filled and laboriously emptied. The lavatory was outside – not a favourite place to visit in winter!



 



In those days there were no jeans or casual clothes of that kind. Boys always wore short, loose waisted grey trousers, buttoned at the fly and held up by an elasticated belt, fastened with an ‘S’ shaped clip in the image of a snake.



 



For my age I know that, compared with the youth of today, I was very naïve, very non-streetwise. I was now ‘a young man’ and was allowed long trousers, but in summer (the time of my tale) I wore baggy legged shorts for comfort in the heat.



 



Girls always wore dresses or a skirt and blouse. Older girls who worked in the factories because the men were at war were allowed to wear long trousers. Boy’s underpants had baggy legs and a girl had elastic around the legs to keep her private places firmly hidden from view!



 



We lived close enough to the club for it to be an easy walk and as Dad was a member of several teams (he particularly enjoyed cards, darts and snooker) we would go there frequently. Fridays and Saturdays were the regular evenings and my Mum would sit with her friends (there was a 'ladies corner') and have a good chat. Dad would sit with his mates and play cards or dominoes, and of course snooker.



 



Friday was usually fairly quiet I remember, and I would watch the men and try to understand their play. One of them was named Reg, a friend of my Dad's. He was so much a friend that I had called him ‘Uncle Reg’ for years. Family relationships and respect for older people demanded a proper form of address



.



Reg was single and lived with his sister, also single, in a street quite close to ours. As we walked to the club he would come out and walk with us, and was always very pleasant and would buy the first drink when we arrived. He always got me a large soft drink, and whenever he saw it empty he would buy me another.



 



He was kind in other ways. He would sit patiently and coach me in some of the domino and card games, and I thought of him as a mature adult that I liked and who treated me pretty well.



 



Drinking so much soft drinks made me continually need to pee and often Reg would go at the same time.



 



The ladies had indoor 'facilities', but males had to go outside and along an unlit gravel path to a slate topped urinal. This consisted of a trough in the floor, and one peed against a tar-coated wall. There were also three lavatory stalls. It was quite roomy to allow for the times that the place was crowded, but it was lit only with a dim blue bulb that was a hangover from the war years. No one had got round to changing it for any brighter light. I think the men might have objected anyway, because the blue dimness gave uniqueness compared with other clubs. It was a masculine joke. It was known throughout the sports leagues. No other could compare with theirs.



 



The blue‑light‑illuminated urinal was known familiarly as 'the blue lagoon.'



 



As we left the rear of the club and crunched over the gravel path Reg had started to put his arm around my shoulders and I accepted this as natural.



 



When wearing my shorts I never undid the flies of my trousers. To pee I simply pulled up the baggy short leg and pulled myself out of my equally baggy underpants. If I wanted them down, I unclipped the snake belt and pulled the loose trousers down over my narrow hips. Providing there were no other men in the urinal Reg would normally stand right next to me. He would very deliberately unfasten the buttons of his fly, pull apart his trousers and take out his cock. With a little more fumbling, he pulled out his ball sac and stood, turned slightly towards me, his fingers moving softly on his manhood.



 



At first I tried to look away but I couldn't resist trying to see  out of the corner of my eye what he looked like. He didn't say anything; merely had his pee, then pulled hard on himself, shook it, and slowly replaced it in his trousers. Then he would look at me and smile and I would smile back. This continued to happen for several evenings.



 



One night I went out followed by Reg. His hand on my shoulder was gently caressing and he pulled me to him as we walked. There was no one else in the blue lagoon. As usual Reg stood close to me. He took himself out and by this time I no longer made any effort to look away. In fact I blatantly watched as he pulled on himself. I finished my pee and let my trouser leg fall. I was about to turn away when his hand reached down and rested on my far hip. He pulled me close. I made no effort to move away as his fingers curled under the leg of my trousers and lifted them up. His fingers slipped inside my underpants and he wiggled them about, brushing my prick. He said "tickle, tickle, tickle" and indeed it did. I giggled and hunched myself. He took his hand away and again caressed my shoulder. We walked back inside the club.



 



For the rest of that evening, each time I went out he would follow. He was I suppose very careful not to make it obvious, but he must have had a watchful eye out for me. If another man were there, he would stand well away and would chat in a natural way. If the man left quickly, he would move to my side. Each time he would lift my trouser leg, and his fingers would dance lightly over my prick and balls. Each time it became more pleasurable for me, and each time I felt myself swell under his touch, and I stood still and let him do as he wished.



 



"Is that nice?" he asked. I whispered "yes." "Do you like what I'm doing?" "Yes" I gasped as he pulled gently on me.



 



All the time he was touching me his other hand was pulling on his cock. Even in the dim glow I could see that it was thickening and swelling.



 



"Can you see mine growing?" he said softly. I could only gasp out that I could. "You are making that happen to me; it's because of you that it's getting hard. Would you like to feel what you are making it do?"



 



I didn't say anything. I just stood and watched his manhood grow in front of my eyes.



 



Still feeling my stiff cock, his other hand took hold of one of mine and placed it on himself. His fingers wrapped around mine and he moved my hand, up and down, up and down. I could hear his laboured breathing and he said, "That feels good. That's very, very good. Your fingers feel so nice on me. Can you do it without me holding your hand? Can you, Teddy?"



 



"Yes, Uncle Reg" I whispered back and I continued to move my hand along his hard, hot shaft. It felt as nothing else had ever felt. Silky smooth, very hot, and as I pulled it, I felt the skin jump over the glans of his knob before the skin covered the end of it.



 



He put his hand back over mine and began to rub faster, harder. Then he was making a soft grunting noise and his hips were jerking backwards and forwards. The cock in my hand was throbbing and pulsing, and after a minute he let go of me.



 



"Have you got any on your hand?" he asked. "Any what?" I whispered. "Is your hand wet and sticky?" "No, Uncle Reg" "Ok, you go back inside. Don't tell anybody what we've done. This is a secret between Uncle Reg and you. Just a secret between men, hey?"



 



I put my hand in my pocket and held my hard prick against my leg as I went back in the club, so that no one would see it sticking out.



 



Later that evening he was playing cards with my Dad. "I've been talking to young Teddy, Jack. He's interested in the night sky, and the planes we used to look out for. I'm going to bring my binoculars next Friday and show him some stars if it's OK with you." My Dad was quite happy with that, it seemed innocent enough.



 



Uncle Reg and Dad had been Air Raid Wardens in the war, and used to patrol the streets during the blackout. Then Uncle Reg became a 'Spotter', looking out for enemy planes and reporting by phone to an AA gun battery. I was thrilled that I was going to be shown how to use the powerful binoculars.



 



The following Friday there was almost no moon and the sky was clear, the stars brilliant in the darkness. Uncle Reg had his binoculars with him and I was desperate to see through them. I was pretty excited, not sexually, but at the thought of what I might see through them. The men were laughing at my excitement and eventually Uncle Reg said "Oh come on then. I'll never get any peace until you've had a go."



 



We went out together into the club yard. He led me around the far side of the club where crates of empty beer bottles waited in a small yard behind a fence, ready for collection. It was quiet and very dark, well away from the path to the Blue Lagoon. He opened the gate and we walked into the yard. He closed the gate behind us and put a couple of filled crates against the gate to stop it from being opened.



 



"Now listen to me, Teddy. These are very expensive glasses. I'm going to keep the strap round my neck so that if you drop them, they won't fall. You'll have to stand on a beer crate so you are high enough."



 



I stood on the crate with my back to him and he put the strap of the binoculars over my head. I took hold of the glasses excitedly and the crates wobbled slightly under my feet. He put his arms around my waist to steady me.



 



My back pressed into his chest and stomach and with one hand he showed me how to adjust them to my eyes. His other hand was now around my stomach and resting lightly on my hip.



 



I was aware of his left hand as it slipped gently down over my hip. It brushed on the outside of my upper thigh. It slipped lower, still with a stroking movement. His fingers had now reached the bottom of my trouser leg and dipped inside. Then they were gliding up inside my trousers, now inside my underpants and I knew again the excitement in my groin as his fingers began to stroke and pull at my prick and balls. I stiffened in his fingers and he massaged me gently.



 



His right arm was around my waist holding me close. His breath was warm as he panted against my neck. My breathing was getting ragged and my body began to tremble, my mouth dry.



 



He moved slightly away from me, but still fondled my hard cock. His right hand was now between us, and I could feel his hand in the small of my back as he fumbled with his trousers.



 



Then both of his hands were at my waist. I realised that he was unclipping my belt. It was undone and he began tugging at my shorts, pulling them down over my thighs. My underpants went with them and I knew the chill of the night air on my bare skin.



 



One hand now cupped my naked cock and balls and he used this hand to pull me close to him. I felt his other hand between us and his hot hard man's cock being rubbed up and down the cleft between my cheeks.



 



His hand left my cock, gripped me tightly round the middle. He lifted me slightly and his other hand tugged my legs apart on the crates. I now stood with legs straddled the night air between my legs.



 



Still holding me tight, his other hand was now back on his cock. After the coolness of the air it seemed to burn against me. It was so hard it could push my cheeks apart and suddenly it was gliding up and down in his hand, up and down, rubbing all along the join between my legs. I knew it was wet, I knew it was slipping easily along me. Each time it passed my bottom hole I felt myself twitch.



 



He stopped rubbing along me. He held it still against my bottom while his hand began to beat up and down along the length of his manhood. There was again the low grunting, again the thrusting, jerking of his hips. Hot wetness spurted against my tight hole and began to run down my legs. He was gasping and so was I. My cock was so hard it was almost hurting.



 



"Oh, Teddy. That was the most wonderful thing. Are you OK?"



 



"Yes, Uncle Reg, but I’m aching down there."



 



"I know what you need. Let me play with you and see if it gets any better.”



 



He held me with my back to his groin and as he started to jerk my cock, he kept pressing himself between my cheeks. I could feel his prick swelling against me once more.  He let go of me and I could have cried with need but he pulled my cheeks apart, put his dick against my bottom hole then pulled me close and started to fuck at me while he jerked me off. I could feel my thighs tingling, my prick was harder than it had ever been, there was fullness in my balls and then my cum spurted out as if I was emptying my whole insides. My hips were jerking and making fucking pushes in time with Uncle Reg fucking at me. It almost hurt when my cum jetted out, I was so tense. Then he cum again against me and I felt his knob end spurt against my ass hole.



 



We stood gasping. Then he said “We’d better go in but first we'd better get you cleaned up."



 



He pulled a cloth out of his pocket and started to wipe all around my bottom and down my legs. He was very careful between my cheeks and asked if he could make sure I was dry.



 



He told me to stand with my side towards him and to bend over. When I did he felt between my legs, all the way to the back and then his fingertip touched against my bottom hole. He pressed gently and I tightened against his touch.



 



"Another time, another time" he said so quietly I only just heard what he said.



 



Then he fastened himself up and said we should go back in the clubroom.



 



"Would you like another go with the glasses one night? he asked.



 



"Yes please Uncle Reg."



 



His teeth showed in the semi darkness as he smiled down at me.



 



After that, every Friday and Saturday night he would take me outside, close the gate behind us, take off my shorts and underpants and rub his cock between my cheeks. He would jerk on my cock and make me cum and finally he would put the end of his on my bottom hole, hold my hips and thrust at me until his cum spurted on me. I always had to bend over so that he could wipe me clean, and he always felt me there and pressed on my bottom.



 



Then he began to make me bend over before he wiped me, and I could feel the smooth wet stickiness of his finger sliding along me. One night he pressed harder and I felt his finger tip go in me. He massaged my hole and smoothed his sticky cum over and in me. At first it hurt a little bit, but he always tried to be gentle and asked me if it was hurting too much. I always said “No” Uncle Reg. Then he asked if I had liked it. I always said “Yes” Uncle Reg.”



 



 



Chapter Two – Teddy learns the hard way.



 



One Friday night my Dad had forgotten his favourite darts and he asked me to run home and get them. Nobody locked doors then so when I got home I opened the door and went to the cupboard where he kept them. Suddenly I heard a noise from upstairs and my sister’s voice. Then I realised there was the noise of bedsprings. I knew about that noise because I had peeked in my Mum and Dad’s room when I heard it and I saw him on top of her and I knew what they were doing. But Mum and Dad were at the Club so I was curious and crept quietly up the stairs. I went down the passage to my sister’s room and the door wasn’t closed. I looked in and she was naked with her soldier boyfriend lying on top. Her legs were spread wide and he was pushing and pumping at her with his hips just like Uncle Reg did to me. I heard him say “Maggie I’m cumming” and she cried out “Take it out, take it out” but he didn’t and he gave an almighty push and collapsed on top of her.



 



My sister said “Get off me you fool you promised to take it out” and he lifted up and I saw she was all hairy between her legs and there was a hole there and it was wide open and creamy white stuff was running out of her hole. I crept away and went to the Club and Uncle Reg took me outside and I saw stars again.



 



A few weeks later there was a terrible row between my Mum and Maggie. I heard Mum tell Dad that Maggie was in trouble and not long after that they were married and went to live away from home.



 



There was a big parade in London and all the Services were there and even my Dad’s Air Raid Wardens were asked to send two men. There was a ‘draw’ and my Dad’s name came out of the hat. He could take my Mum and they would be put up in military barracks for two nights. My Dad said they couldn’t go because they would have to leave me behind because Maggie was living in Scotland now. Uncle Reg told him not to be a fool because I could stay with him and his sister. So Dad said was it OK if I stayed with them for a week because they could see relatives who lived near London. So I did.



 



Uncle Reg was about my Dad’s age. He was quite tall, 6’ 1’’ I think. He was very slim and my Mum used to say he was handsome. My Dad would pull her leg about her saying that. Dad would say she would have to watch herself and not get caught in a dark alley with him or else. She would pretend to slap him but she liked the teasing I know she did.



 



His sister Lizzie was a bit younger than him. She was very pretty I thought and the smell of her was always nice and not sweaty at all. I was always surprised she didn’t have a husband for herself.



 



Uncle Reg was some sort of boss where he worked. They didn’t live in terraced houses. They lived in a semi-detached house and it had an inside bathroom and inside lavatory. It was really posh. It had three bedrooms.



 



The other half of the semi-detached house had a widow living there. Her husband had been killed in North Africa by the Germans in 1941, and she didn’t have any children. Her name was Rose and she and my Aunt Lizzie were great friends. While I was with Uncle Reg she even stayed with Rose for two or three nights because she said that Rose was still weepy about her dead husband, and Aunt Lizzie would be a friend for her and comfort her. They must have been really good friends because once I saw Aunt Lizzie kissing Rose. It must have been to make her cheer up I think.



 



The first night I stayed with them my Aunt Lizzie stayed with Rose so she wouldn’t be alone and feel sad.



 



Before bedtime my Uncle said he would teach me hygiene for myself and did I know about a thing called an enema so I was really, really clean. I didn’t know about that. He said it was a bit like me brushing my teeth and washing my boy pieces properly all the time, only this was to do with my bottom, my bum. He showed it to me and told me how to use it and to let it pour into me and then sit on the lavvy and let it out. Only I had to do it several times until the water from me was clear. He said he used it all the time and it made him feel really clean and good inside. He said Aunt Lizzie used it too.



 



He said it would feel funny but after I was really clean it would feel great for me. And he was right.



 



In his house it was like living in a palace. The bath was there all the time in its own room. You didn’t have to take it outside to empty it and then hang it on the wall; and there was real hot water coming out of the taps, and there was nothing to empty from the bath you just pulled a plug out and the water all went down the hole in the bath. That night after I had used the enema he filled the bath for me and gave me soap and the soap smelled nice. He helped me wash and I stood in the bath and he washed soap all over me with his hands. Then I sat down and he poured water all over me.



 



Then I had my very own towel, not a shared one, and he helped me get dry.



 



When I was dry he showed me to my bedroom. He kissed me. It felt nice. I was tired and I went to sleep.



 



I woke up and it was dark. I wasn’t by myself anymore. I knew it was Uncle Reg holding me because I could feel him pressing his cock at me. He had his hand in the opening in my pj bottoms. He was playing with my cock and making it hard for me. I must have made a noise because he pulled the cord on my pjs and said, “Take them off” and I did. Then he undid the buttons on my coat and suddenly I was bare.



 



When I was naked I could feel his skin against me and I knew he was bare as well. He was feeling my cock. I loved him feeling it. I tossed it off at home and thought it was his fingers doing it, but his fingers were much nicer. After a few minutes I got that funny feeling somewhere inside, like a little knot somewhere behind my balls. My legs started to tingle. It was like heat coming up my legs, in my little knot, into my balls and then I was fucking at his fingers and my hips were jerking as my cum spurted out over my face and chest and belly. When it stopped he gave me my pj bottoms and told me to wipe it off me.



 



He turned on a bedside light and made me stand up. I’d never seen him naked, only been with him in the dark. He had a hairy chest and curly dark hair round his dick that drifted up to his belly button like a little whirlwind. His cock looked angry and wanting as it made little twitches in front of my eyes. His foreskin had gone back off the end of his knob and that was sort of purple red and his cock had blue veins standing up all down its length. It didn’t seem huge like I expected, but it was bigger and fatter than mine, but not all that much.



 



He put a big towel over the sheet.



 



“Lie on the towel Teddy” he said. I lay on my back and he said “The other way. Bottom up.”



 



As I turned onto my tummy I suddenly felt a bit nervous. I knew what he was going to do. While I was lying down he was going to do what he’d done to me standing up but I knew this time he was going to get it in.



 



“Teddy, don’t be scared. I’m going to be very careful and gentle. I’m going to use lots of cream for you. You know what I’m going to do don’t you?”



 



“No, no Uncle Reg I don’t know.”



 



“Yes you do. You know you want me to so don’t be a baby now. Not after the way we played at the club in the dark. You know you want it as much as I do. Teddy I’m going to fuck you, OK?”



 



I didn’t say anything, just screwed my tight fists into my eyes. I was shaking and shivering and all my skin seemed to be goosebumps. He pulled my cheeks apart and I could feel his knees each side of my hips. A he opened my bum cheeks it was like a shock had run up and down my spine. His fingers were cool on me and I realised it was a sort of creamy stuff he was putting on my ass. His fingers worked on my hole and he told me to relax. I tried and tried but it was hard not to clench up. He told me to take a deep breath and let it out again slowly, and as I did his creamy finger was pressing at me and suddenly it slipped in. I could feel him wriggling his finger around in my ass then he used his other fingers to put lots more cream on me. His finger came out then went in with more cream on it. He kept doing that. More and more cream in me and on me.



 



He was wiggling his finger round and round and I could feel it getting easier for me. Then he was pushing two fingers in and after making me loose for them, the he did it with the tips of three. He’d put two fingers right up as though they were fucking me. But with three they were only a little bit in.



 



His fingers were slipping in and out, easy now and they didn’t really hurt, not really, really hurt.



 



I could feel all the tense muscles in my neck and my back and my legs and my thighs relax and as I lay there it started to feel not too bad. Nice in fact.



 



His fingers pulled out and I knew he was changing his position above me. Then I felt the familiar blunt hardness of his cock pushing at my asshole. For a moment my muscles contracted to deny him, but he had prepared me well and I felt his knob end lodge inside. I whimpered as it started to stretch me and then it went in and I cried out. The pain was awful. I think I was crying a little bit with the pain.



 



“Teddy relax my little friend. That’s the worst over. It’s going to be nice for you now. It’ll always be nice after this.”



 



I was gasping, trapped underneath his man’s weight. I felt him push and my body allowed him in. Then he eased back and pushed, again he eased back and pushed, and little by little I felt his swollen cock filling my insides. When it was all inside me, he lay still. His arms held him up from crushing me now. His cock was buried all the way up me and I could feel the roughness of his dick hairs pressed on my firm bum cheeks.



 



I was panting. I realised my hands were clenching on the pillow. My own dick was hard underneath me. He started to fuck me.



 



I felt his hardness slide out, almost right out, but before it left my hole he slowly pushed back in. His groin pressed hard onto my buttocks, and my hips ground on to the towel, and my cock had its little throb against the roughness of the towel.



 



I knew when he was close. I knew his urgency. I had a mental image of my sister saying ‘Take it out, take it out.’ I saw in my mind her slit, her hairs, her hole and her boyfriend’s cum as it ran out of her.



 



Uncle Reg rammed at me and froze. Inside me I could feel his cock jerking and throbbing and pulsing and the warmth of his spurting. My bum was lifting to his every spurt. Then he was done. He relaxed. He held himself from crushing me and I heard his whisper in my ear.



 



“Teddy, Good boy, good boy, good boy. Oh my sweet boy. Oh my darling boy. Oh Teddy.” Then as he calmed he said



 



“Teddy did I hurt you. Was it good for you?”



 



 “It hurt me Uncle Reg. It was nice after it went in though.”



 



“It won’t hurt so much next time. Shall we sleep together then we can do it again? My sister is busy tonight and won’t be home.”



 



“Yes OK Uncle Reg.”



 



As I stood up his cum ran out of me and down my leg but he had the towel and wiped me. Then he took me to his bed. The first thing he did was to make sure I slept on his towel.



 



During the night I woke and he was feeling my cock. He made me lie on my back. We weren’t covered with sheets or clothes or anything. When I felt myself starting to cum I could hear myself making noises and he did it more and more and then it spurted out, like tearing out of me, it was so strong. He held me and rubbed my cum over my balls, then he spread my knees so he could rum my cum over my ass hole.



 



“Turn over” and I did. He straddled me and put the cream on me. I felt his knob end forcing me open. Then he was gently sliding in and he started to fuck me. It didn’t hurt so much, only a little bit. When he finished he didn’t wipe me and I felt cum dribble out of me and on the towel. As I went to sleep I could see my sister Maggie with cum running out of her.



 



Chapter three – The understanding Aunt



 



 



I must have been tired because I slept late. I heard movement in the room and thought it was Uncle Reg but when I opened my eyes it was Aunt Lizzie. I was naked and still lying on the towel and she had my pj bottoms in her hand. She was fingering the stiff parts where my cum had been wiped up.



 



I felt shy and covered my cock with my hand but she laughed and said



 



“Teddy, dear, you don’t need to cover it up, I have seen men before” and she laughed again. The she took my hand away and looked at my dick and my hairs all stiff with cum round it and I couldn’t help it my dick started to swell up.



 



“I am going to run a bath for you so you can get cleaned up. I’ll tell you when it’s ready.”



 



I heard the bath water running and after a minute she told me to come through. My clothes were in the room Uncle Reg had given me and she had my pj bottoms. “I haven’t got any clothes,” I yelled.



 



“You don’t need any just come through here and get in the bath.” I put my hand over my cock and went in the bathroom and she was standing there. I had to use my hands to steady myself on the wash basin to get in the bath, and I saw her looking at my cock.



 



I sat down and she sat down on the toilet lid.



 



“Teddy, are you alright?”



 



“Yes” I said “why?”



 



“I just want to know you are happy. Are you happy?”



 



“Yes, you are really kind and I like your house and everything.”



 



“EVERYTHING?” she stressed.



 



I blushed all the way down and hung my head. “Yes.”



 



“Uncle Reg hasn’t hurt you has he?”



 



I shook my head ‘No’ and she said, “Well as long as you are happy.”



 



“Yes, Aunt Lizzie I am happy. I like Uncle Reg.”



 



“Teddy I know what he did. You were in his bed this morning. He likes handsome boys like you and I’m glad it was nice for you as well. But, Teddy, it is even nicer with girls so I want you to think about girls as well and not think only about men” and she kissed my shoulder and went out.



 



I lay in the warm water and relaxed. My bum hole felt a little bit sore.



 



She came back in with my towel and told me to get out of the bath. I felt a bit shy being all bare in front of a lady, but I got out and she dried my back. She asked if I was sore and I blushed and said I was a bit sore.



 



She said to lie on my bed she had a soothing cream. I didn’t know what to do so I was still standing naked when she came in my room.



 



“Lie on the bed” so I lay on my back with my hands over my cock. “On your tummy.”



 



I turned over and she opened my cheeks and gently rubbed nice smelling cream on my ass. Then she told me to lie on my back and I did.



 



She took my wrists and moved my hands away from my cock. It excited me that she was looking at it and then it started to get hard. She kept holding my wrists and looking all the time and I couldn’t help it, it just got harder and harder and harder. It was pointing straight up towards my chin and it kept twitching.



 



She said, “I think we should take care of that or you will get the aches. Have you ever seen a lady with no clothes on?”



 



I shook my head and she undid the buttons on her blouse and took it off, Then her bra. I saw a woman’s tits for the first time and my heart was nearly bursting. Then she took her skirt off then her panties and there was nothing there. Not like a man. There was nothing there except hairs and a gap between her legs.



 



She knelt over my thighs and I could see her spread wide and the slit that I’d seen on my sister. Then she held my cock and started to rub it and jerk it and I was looking all the time at a real woman who was naked for me. I thought my balls were going to burst when my cum spurted on my face and chest. She rubbed some of my cum on her breasts and the rest over my chest. She bent down and kissed my lips and I felt her breasts press softly on my chest. Then I knew the feeling of her slit as it touched along my soft cock.



 



“Good boy, Teddy. You are a wonderful man. Don’t forget. You are a man. Tomorrow when Uncle Reg is at work, we might make you a proper man. A real man for a lady. I will see. Now get cleaned up and do anything you have to do for when Uncle Reg comes home from work. I shall sleep at Rose’s house again tonight.”



 



She stood and I looked achingly at her female body. All soft curves and hollows and shadows and loveliness.



 



When Uncle Reg came home I had bathed and used the enema thing and was dressed neatly. I was clean for him. Rose served dinner and after we had eaten and she had cleared the dishes, she went to see her friend Rose again.



 



We sat and talked a little about my interests, and he asked me if I was ‘ready for bed.’ I said “Yes” and he asked me what I had done to get ready. I told him I had bathed and used the enema like he had told me and I was clean all over. He grinned and told me I was a good boy. We listened to radio and he read his paper and smoked his pipe. I must have fallen asleep because he woke me and I had gone to sleep on his couch.



 



“Go to bed, Teddy. Remember to get in my bed. And don’t forget to put the towel on the bed.”



 



I did as he told me and fell fast asleep but I had this little excited feeling in my tummy. Like little butterflies. I knew I was going to get it again.



 



I woke and he was holding my back to his stomach and I could feel his cock poking between my cheeks. He was playing with my cock and pushing his own hard one at me and when he knew I was awake he said, “Get on your stomach” and I knew it was going to be now. He had the cream with him and he rubbed it over my bum hole and in it and then his fingers were in me again making my muscles relax to make it easier for him to get in, and for me to let it in. Then he lay over me and I felt helpless and trapped underneath him. Even if I wanted to I couldn’t get him off me, and whatever I did or said he was going to fuck me until he’d had enough and finished.



 



It was easier than before. He told me to take a big breath and let it out slowly, and as I did I felt him force me open with the hardness and strength of his prick. Then his knob was up me. He eased out and in, and again out and in, and kept doing that and each time I felt more of it filling me up. I could hear myself groan every time he pushed in, not because it hurt much, but it just made me feel good to be going, groan, groan, groan as he fucked in me. My own dick was hard against the towel and when he pushed in, his hips made my cock rub on the towel and that felt nice for me. Soon he was going harder and faster, then he gave his big push and I felt him jerking and spurting up me. He lay gasping and I felt his cock slowly get smaller and then it slipped out and I felt his cum run from my ass down over my balls.



 



When he had stopped panting he got off me and lay at my side holding me, and saying, “Good boy. Good boy Teddy. You are a very good boy for Uncle Reg.” Then he was quiet and he was asleep.



 



He woke me early in the morning before he went to work and after he had done me again I fell asleep.



 



Aunt Lizzie woke me and told me breakfast would soon be ready. She asked if I was ok and if he’d hurt me and I said ‘no he hadn’t hurt me’. When I stood up suddenly his cum started to run down my legs and I grabbed the towel to wipe myself and Aunt Lizzie giggled and said before you do anything else get in the bath.



 



She came in the bathroom with my towel and told me to stand and she would help me get clean. She washed between my legs and felt my bum then she pulled my foreskin back and washed my cock really clean and fresh. I got hard and she kissed my cheek and said, “We’ll have to take care of that for you won’t we.”



 



I dressed in clean underpants and my shorts and a shirt and went downstairs. After breakfast she cleared away the dishes and said she would have a bath herself as it had been very hot in Rose’s house last night and she felt very sticky.



 



I could hear her splashing water about and there was the smell of her nice flowery soap and I tried to picture her woman’s naked body with breasts and hairs and not having a dick hanging there. Uncle Reg hadn’t made me cum last night and I felt my cock getting hard thinking about her.



 



When she came downstairs she looked pretty and fresh and she had combed her hair and wore her lipstick and makeup. She had put on a cotton dress with flowers all over it and she looked really nice.



 



After doing some things in the kitchen she went upstairs and after a few minutes I heard her call to me to come up to her room.



 



I hadn’t been in her bedroom before. Her bed wasn’t as big as the one Uncle Reg had. The covers were pulled back and the sheets looked cool and fresh. There was a dressing table and mirror and she had her makeup things on that. There was a chair for her to sit on in front of the mirror, and a chest of drawers and a wardrobe.  There were pretty curtains with a flower design and they were pulled closed.



 



She stood in front of me and stroked my face and then she held my shoulders and gave me a little kiss on the mouth. Her lips were soft and when she took them away and I licked my lips I could taste a lovely sweetness from her lipstick. She smiled as I licked my lips then kissed me again. Her hands were stroking my arms and I started to shiver. Then the shiver was a shake down to my hands.



 



“Sit on that chair, Teddy” and when I did, with my back to the mirror, she again stood right in front of me. “Would you like to see me again, Teddy, like yesterday?” I swallowed hard and managed to gasp “Yes please.”



 



She started to unfasten the buttons on her dress right at the top. When she got down to her middle she said “You undo the rest for me.” I couldn’t believe it. I was going to undo a woman’s dress and see inside.



My fingers were really trembling as I reached out and fumbled with the buttons. She just stood and waited and let me struggle and one by one I got them all undone right down to the bottom of her dress.



 



I didn’t know what to do, or could do, or if she would let me do anything else and I looked up at her face.



 



“Open it.”



 



I pulled it open and again saw her breasts all held up in her bra. I looked down over her tummy and instead of baggy blue girl knickers with elastic round the leg she had panties. A sort of pink silky stuff and lace round the legs and the legs were all baggy.



 



She turned her back and said, “Unfasten my bra.”



 



I stood up and there were clips holding it together and I undid them and she shrugged and the straps fell off her shoulders and the bra fell down on the floor. She turned to me and I saw her bare breasts with the nipples all pink and hard sticking out at me.



 



“Stand behind me.”



 



She got close to the dressing table and I could see her in the mirror from her face to her thighs as I looked over her shoulder. Her naked breasts and her woman parts covered in this pretty silk.



 



“Put your arms round me and feel my breasts.”



 



I saw my hands and arms in the mirror and my hands reaching up. This had to be a dream. It couldn’t be true. But it was true because her hard nipples were under my hands and she was whispering “Stroke them gently.”



 



My hands were shaking like mad and my dick was hard and trapped in my underpants. I was holding her close to feel her and my trousers were hard against her panties. Then she said, “Take all your clothes off.”



 



I couldn’t get them off fast enough and while I did that she just stood waiting in front of the mirror. Then I stood close and felt round for her breasts and my knob touched the silk panties covering her bottom cheeks and it felt really good and I knew why Uncle Reg liked feeling his knob on me just there. I pushed my dick at her and she pushed back at me. We kept doing that. Both of us pushing at each other and my dick started to push the silk between the cleft of her cheeks.



 



“Feel my breast with one hand and feel underneath my panties with the other one, Teddy.” 



 



I watched as this hand, my hand, slipped down over her hip and like Uncle Reg had to me, I put my hand under the leg of her panties and felt up at her. My fingers were in her hairs and I was desperate and grabbing to feel more.



 



“Gently, gently, Teddy. Be gentle for a girl.”



 



I tried to be gentle but my hands were shaking and I had my fingers in between her legs and it was wet and slippery and there wasn’t a dick hanging there and I exploded my cum between her cheeks and over her panties. My hips were jerking at her as I fucked at her cleft and she was pushing back at me every time I went forward. My arms were holding her tight or I think I would have collapsed on the floor.



 



I was panting and I could hear her breath, heavy and her chest heaving in my arms. She had one of her hands over mine inside her panties and she was using my fingers to rub and stroke and feel at a hard thing there. Then she was crying out and her hips were jerking at my hand and she was holding my fingers tight between her legs.



 



After a minute she turned to me and held me tight. “Teddy that was Mmmmmmmmm. Let me take these wet panties off.”



 



I stepped back and she took them down slowly over her hips, and I saw her hairs and her gap and her legs, then she stepped out of them and we were naked in front of each other.



 



She took my hand and led me to the bed. I expected her to tell me to lie down for her like I had to for Uncle Reg. Instead she lay down on her back. “Kneel beside me.”



 



When I did that she said, “I’m the first lady you’ve seen. So you can look at me anywhere and touch anywhere so you can see how a lady is made and where she’s different from you men.”



 



WOW she had said “YOU MEN” and she meant ME.



 



I touched her breast and I saw her nipple go from soft to hard. I stroked it and she told me to kiss it. I sucked on the nipple and I heard her sigh. Her hand was stroking her other nipple. After a while she said “Now the other place.”



 



I looked at her and she smiled and her eyes were all soft and a bit puffy and she said “Yes, between my legs.”



 



She took my hand and placed my fingers in her hairs, then I felt her legs spread wide and she was sliding my fingers in between where it was all wet. She took my middle finger and moved it and there was a tight hole and she pushed my fingertip at it and said “Put your finger in me.” I pushed and I felt the wet warmth of a woman gripping my finger.



 



“Keep pushing it in and out and don’t stop ‘till I tell you.” My finger went right in all the way and when it came out of the hole it was wet. The more I did it the wetter she got and then she put her own fingers in her hairs and started stroking. Her other hand reached down and was feeling my cock, stroking and feeling it. Her fingers were really soft and gentle and not like mine when I jerked it off or Uncle Reg when he made me cum.



 



Her hand stopped feeling in her hairs and she took my finger out. “Get between my legs. Hurry. Hurry Teddy.”



 



I knelt between her spread legs and I could see she was all puffy and a bit open from my finger. She took my cock and pulled it to her and I felt the very tip of my knob as she moved it up and down her slit and I got all slippery from her. She held it still and said, “Push. Keep pushing. Don’t stop pushing.”



 



It was incredible. My cock went straight in. I felt this wet warm tightness all around my dick. Her hips pushed at me and I pushed back. “Keep pushing in and out. Please don’t stop Teddy.”



 



Her hips were lifting and pushing and I couldn’t get my push at her right and my dick came out.



 



“PUT IT BACK” she shouted and grabbed it and held it so my cock would go in her hole again. Her hands were on my hips now and as she pushed at my dick she pulled me to her and got the timing right so I stayed inside her hole. One of her hands went between us just above my cock and I could feel them twiddling at herself as I went in and out and then her head was rolling from side to and she said “I’m cumming, fuck me, fuck me, fuck me” and her lips lifted right up and held me in the air and she was calling out and making noises and “Yes, yes, yes.” Then she fell back on the bed and she held my hips tight to her.



 



I was hard and I wanted to keep pushing but she held me still for a minute. Then she said



 



“Oh, Teddy. You poor man you. I was greedy. Please keep doing it to me.”



 



I started pushing in and out and nearly straight away I felt my legs tingling and it was in my balls, all swelling up and I spurted and spurted like I would never stop. She held me close when I collapsed on top of her. I was sobbing and panting and shaking and she was making little soothing noises to me “Good boy. Good man. You are so GOOD, Teddy. You made me feel like a woman. You were a man for me” and I felt proud and contented and couldn’t believe I had done it to her.



 



My prick slipped out and she pushed me onto my back. She climbed over me and spread her legs over my tummy and I saw her hairs all covered in sticky stuff.



 



“Watch,” she said. I saw white creamy stuff drop out from between her legs and fall on my tummy. “That’s your man cum. You filled me with man cum, Teddy.”



 



For the rest of that week Uncle Reg would do me in the night-time in his bed. During the daytime I would do Aunt Lizzie in her bed. She let me look everywhere between her legs and held herself open so that I could see where my prick went when I fucked her. She told me how a man had to be careful not to make the girl pregnant and that the man must always be gentle with a girl and never ever to force her to do anything she didn’t want to do. She showed me how to make the little lump come up for her at the top of her slit and told me it was her clitoris, her clit, and that if the man did it right it was heaven for the girl to let him touch it for her. She told me about contraception, and that she had used a special cream inside herself so that I didn’t make her pregnant.



 



I felt 10 feet tall. She had to use something so my cum didn’t make her have a baby. I was a MAN.



 



Epilogue



 



She let me go to see her sometimes in the day when Uncle Reg was at work. Not every time, but sometimes she would kiss me and take me to her bed. She always told me that I would be wonderful for a girl to love. She gave me confidence in being a man.



 



At the weekend I was often invited to have tea with Uncle Reg and her. Straight after tea she would go to be with Rose and would tell us when she would be back or if she was staying over. Uncle Reg would then tell me to go and get ready and I would use the enema and take a bath. I would get dry and put a towel on his bed and wait for him, naked. Soon he would come to me.



 



I always enjoyed what Uncle Reg did, being submissive and letting him have me. It was always exciting when he followed me outside at the club, or when he told me to meet him during the dark evenings of autumn when he would take me to a secluded spot on waste land.



 



After the war there was no street lighting for years, so everywhere was dark. Quite often we would be aware of dim figures not far away, and would hear female cries of lust as she was fucked by her man and I would picture Maggie’s spread legs, her hole leaking cum. Uncle Reg would take down my trousers, cream me and I would thrill to his penetration as the other couple were moaning.



 



He never asked me to fuck him. I never wanted to. I never have fucked a man. I am content and get the greatest pleasure by submitting.



 



I always loved what Aunt Lizzie taught me. Making me a man and teaching me to be patient, to give her orgasms as well as myself. I discovered the pleasure of being bi-sexual. Without Aunt Lizzie I don’t think I would ever have known the intensity of love I could have for a woman.