sissy baby Jenny is a cuckold
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Becoming Sissy Jenny Part One free porn video
Hi, my name is Jonas and I´m 25 years old. This is the Story of how I became a sissy. So actually my name is Jenny now. But lets not get ahead of ourselves. The story has a slow build up, I hope it´s interesting for someone. Thats part one, I will continue the story from time to time. Everything sexual in this story happens to people over the age of 18.
I guess it all started whit my mom being a gold digger. One of those women who have a pretty face and a nice body and try to make a living out of it. After a few years of being an escort, getting to know people, sucking the right dicks, getting bend over the right tables she eventually met some rich dude who decided to marry her. Not only was he rich, he was also quite old. He was perfect for her, rich, old and never married before, so no k**s to inherit his wealth. Everything went according to plan, except for one tiny thing: me. The old man got her pregnant before he passed away four years later. I´m not really sure why she even told him, she could have terminated the pregnancy, but she didn´t. I guess she wanted to make sure he wouldn´t do something unexpected with his heritage, like giving it to charity or something. The only certain thing is, that she didn´t want to have me or better to actually take care of me. After my dad died she made sure I go to a boarding school as soon as possible. I guess I don´t get to bitch about her to much, she did make sure I would always get everything I need and never need to worry about money. Wont complain about that. Only thing I didn´t get were parents. But to be honest I didn´t miss it, can´t miss what you never had. My dad died so early that I can´t really remember him and my mom avoided almost any contact with me, especially after she got all my dads money. For her it was like her actual life started.
Well like I said, my mom sent me to a boarding school as soon as possible. Since I was six years old I spend most of the year at school. Only for a few weeks in summer I left school. But even then she often send me to some summer-camp or stuff like that. Well you get the picture. Arriving at school I had to figure out pretty soon, that I seem to have some sort of victim-aura. Bottom of the food chain, starting at day one. I guess everybody knows those clichés about boarding schools, and most of them are true. Bullys on every corner, teachers not noticing it or not caring about it. While in class everything is very disciplined, but as soon as school is out, that changes drastically. It´s not like I got beat up a lot or something like that, k**s can be mean, but they don´t run around like some violent gang or something. They are just mean to you, play pranks on you, call you names, stuff like that. I guess they did it out of boredom, there wasn't much to do accept for chores and homework. I read books most of the time, most of the other k**s got more creative than me. For me it was always: out of the classroom and to my dorm as unseen as possible.
That went on for a long time, but eventually I got my mom to have a heart and send me to another school. I was hoping to have a few last school years in peace before I graduate. I arrived at my new school a week before classes would start. Most of the other students would arrive in the next couple days. I got led to my dorm room, my roommate had not arrived yet. Its a small room, witch two beds, two tables and two dressers. There is a small bathroom, with a toilet and a sink. I started to unpack my stuff, when I finished I went to take a shower. Maybe I should describe myself a little at this point. I never was very tall, but going through puberty I got a small boost and got to 1,76 cm pretty fast. I have blond hair and at that time I didn´t really care about how it looked. It was kinda longish and tousled. There was never a lot of hair growing on my body, except for small bushes under my armpits and in my genital area, there wasn't much going on. No need to tell you that I didn´t need to shave my face. I shaved the rest of my body, I had no special reason to do it, I just figured it wasn´t much work and if I can´t grow a decent amount of hair, why have any? I weight something between 60 and 70 kg. So I wasn´t very skinny, but not fat or muscular ether. My dick is very small when it´s flaccid, I´d say around 5 cm. Erected it reaches unspectacular 13 cm. I had seen allot of other penises, because I always had to shower with other boys in my school, so I knew my penis wasn´t a highlight. But I didn´t really care, there were no girls around anyway and I convinced myself that size didn´t matter. I didn´t mention yet, but just like my old school, my new school is an all boys school. So I am in the shower washing myself, thinking about whats ahead of me. "I don´t wont to be the loser again!", this time would be different. I needed a plan. What did I do wrong last time, why did they all push me around? What was it that made me a victim?
Thinking about my new start at this school I didn´t notice that someone else had entered the shower room. The room was quite big and had several entrances, they all led to different dorm room departments. The shower room didn´t provide much privacy, there were no separating walls or something. Just some shoulder high walls to support the shower heads. Those walls also separated the room into six rows. There where no showers at the outside walls, they had hooks for towels, benches and stuff like that. So I didn´t notice the other guy until I was finished washing myself. I went to my towel and started drying myself. He didn´t seem to have noticed me either or he just didn´t care about me being there. At least he didn´t acknowledge my presents. I looked at him, he was taller than me at least 1,85 cm. Dark hair and unlike me not only on his head. He turned his back to me and I noticed how hairy his ass was. I knew you could have hair there, but had never seen such an hairy ass. I reached around to check my own hair growth on my ass, never thought of shaving there. No hair on my checks, but I fund some lonely hairs right around my asshole, they would be gone next time. Still drying myself up I took another look at the showering guy, he was now turned sideways to me, still not paying attention to my presence. He was soaping up his body, with my eyes I followed his hands sliding around his body. Eventually his hands reached his cock. I noticed his cock was semi erected. He started to slide his slippery hand gently up and down his penis. I noticed that his cock was quite large, now that it was fully erected it was at least 18 cm long. He started to stroke his forehead only, his foreskin was pulled back completely. I knew about masturbation and technically knew how it´s done, but I had never done it to myself or seen someone else doing it. Internet porn wasn´t that far spread at that time, especially at schools and I where never cool enough to get a good look at those magazines, that got passed around at my old school from time to time. So I never got really experimentive with my occasional hard on. So seeing him pleasuring himself got me hooked. I kept watching him. He poured some more soap on his cock with his free hand, while continuing jerking his forehead with his other hand. Even though I couldn´t here him over the sound of the shower, he sure looked like he made some grunting noises. He started to stroke faster and faster. Suddenly I noticed how my own cock got stiff. Quickly I put my towel on it to hide it. Doing that, I couldn´t resist to rub the towel agains my stiff penis a bit, pretending to dry my privet area. It felt nice, kinda ticklish. I looked back at him. He was still stroking his cock very fast, it seemed quite exhausting at this point. Additionally to jerking his cock he was now kinda twitching, meeting his strokes by making quick and small thrusts with his hips. Than he suddenly stopped, I froze too. Witch one hand grabbing the wall he threw his head back and kinda thrusted into his other hand, now holding still.
Now worrying about him, noticing me, I quickly grabbed my stuff and went to my room with my towel around my hips. I put on my pajamas and laid in my bed. My little dick was still kinda hard and I kept thinking about what I just saw. What fascinated me the most was what I had seen at the very end. I guess I envied him for his a****listic drive to pleasure himself. He must have known that he wasn´t alone in the room, but he didn´t care. He wanted to pleasure himself and he did, he took what he wanted, I never could do that, I did´t have the courage. The amount of pleasure his body expressed kept going through my head. I closed my eyes and saw him again in my mind. I saw him in those last few moments before his orgasm. He is sliding his hand up and down on his cock, all the soap making it slippery. I hear myself breathing heavy. Without thinking about what I am doing, I start to touch my body, reaching under my pajama top with one hand, caressing my tummy, gently fondling my boyish breast and nipples. My other hand finds its way into my pajamas pants. I start to slowly stroke my dicky, using my foreskin to glide over my forehead. The water is raining onto his body, his hairy chest is soaked in water, I remember him having a muscular body. I feel inferior, my breathing gets even heavier and faster, I intuitive start to move my hips. But not in thrusts like he did, I make slow, circuiting movements, stroking my cock faster now. His lags muscles are clenched from the effort he puts into thrusting into his own hand. He grabs the wall and throws his head back. I stroke my dicky as fast as I can. Now he is making his finale thrusts, satisfying his basic needs, he gets his relief and empties his balls onto the floor of the shower room. I let out a tiny moan and arch my whole body, experiencing my first orgasm, I shoot my load on my stomach and immediately smear it all over my smooth and hairless tummy, still orgasming. For a second I get the urge to lick some cum of my hand, but I hesitate and the urge passes. I curl up into a ball, holding my now flaccid cock and my balls in my hand, twitching a little. After my breathing calms down to normal, I get up, go to the bathroom, and clean myself up with a towel and some water. Then I go to bed and quickly fall asleep.
I guess it all started whit my mom being a gold digger. One of those women who have a pretty face and a nice body and try to make a living out of it. After a few years of being an escort, getting to know people, sucking the right dicks, getting bend over the right tables she eventually met some rich dude who decided to marry her. Not only was he rich, he was also quite old. He was perfect for her, rich, old and never married before, so no k**s to inherit his wealth. Everything went according to plan, except for one tiny thing: me. The old man got her pregnant before he passed away four years later. I´m not really sure why she even told him, she could have terminated the pregnancy, but she didn´t. I guess she wanted to make sure he wouldn´t do something unexpected with his heritage, like giving it to charity or something. The only certain thing is, that she didn´t want to have me or better to actually take care of me. After my dad died she made sure I go to a boarding school as soon as possible. I guess I don´t get to bitch about her to much, she did make sure I would always get everything I need and never need to worry about money. Wont complain about that. Only thing I didn´t get were parents. But to be honest I didn´t miss it, can´t miss what you never had. My dad died so early that I can´t really remember him and my mom avoided almost any contact with me, especially after she got all my dads money. For her it was like her actual life started.
Well like I said, my mom sent me to a boarding school as soon as possible. Since I was six years old I spend most of the year at school. Only for a few weeks in summer I left school. But even then she often send me to some summer-camp or stuff like that. Well you get the picture. Arriving at school I had to figure out pretty soon, that I seem to have some sort of victim-aura. Bottom of the food chain, starting at day one. I guess everybody knows those clichés about boarding schools, and most of them are true. Bullys on every corner, teachers not noticing it or not caring about it. While in class everything is very disciplined, but as soon as school is out, that changes drastically. It´s not like I got beat up a lot or something like that, k**s can be mean, but they don´t run around like some violent gang or something. They are just mean to you, play pranks on you, call you names, stuff like that. I guess they did it out of boredom, there wasn't much to do accept for chores and homework. I read books most of the time, most of the other k**s got more creative than me. For me it was always: out of the classroom and to my dorm as unseen as possible.
That went on for a long time, but eventually I got my mom to have a heart and send me to another school. I was hoping to have a few last school years in peace before I graduate. I arrived at my new school a week before classes would start. Most of the other students would arrive in the next couple days. I got led to my dorm room, my roommate had not arrived yet. Its a small room, witch two beds, two tables and two dressers. There is a small bathroom, with a toilet and a sink. I started to unpack my stuff, when I finished I went to take a shower. Maybe I should describe myself a little at this point. I never was very tall, but going through puberty I got a small boost and got to 1,76 cm pretty fast. I have blond hair and at that time I didn´t really care about how it looked. It was kinda longish and tousled. There was never a lot of hair growing on my body, except for small bushes under my armpits and in my genital area, there wasn't much going on. No need to tell you that I didn´t need to shave my face. I shaved the rest of my body, I had no special reason to do it, I just figured it wasn´t much work and if I can´t grow a decent amount of hair, why have any? I weight something between 60 and 70 kg. So I wasn´t very skinny, but not fat or muscular ether. My dick is very small when it´s flaccid, I´d say around 5 cm. Erected it reaches unspectacular 13 cm. I had seen allot of other penises, because I always had to shower with other boys in my school, so I knew my penis wasn´t a highlight. But I didn´t really care, there were no girls around anyway and I convinced myself that size didn´t matter. I didn´t mention yet, but just like my old school, my new school is an all boys school. So I am in the shower washing myself, thinking about whats ahead of me. "I don´t wont to be the loser again!", this time would be different. I needed a plan. What did I do wrong last time, why did they all push me around? What was it that made me a victim?
Thinking about my new start at this school I didn´t notice that someone else had entered the shower room. The room was quite big and had several entrances, they all led to different dorm room departments. The shower room didn´t provide much privacy, there were no separating walls or something. Just some shoulder high walls to support the shower heads. Those walls also separated the room into six rows. There where no showers at the outside walls, they had hooks for towels, benches and stuff like that. So I didn´t notice the other guy until I was finished washing myself. I went to my towel and started drying myself. He didn´t seem to have noticed me either or he just didn´t care about me being there. At least he didn´t acknowledge my presents. I looked at him, he was taller than me at least 1,85 cm. Dark hair and unlike me not only on his head. He turned his back to me and I noticed how hairy his ass was. I knew you could have hair there, but had never seen such an hairy ass. I reached around to check my own hair growth on my ass, never thought of shaving there. No hair on my checks, but I fund some lonely hairs right around my asshole, they would be gone next time. Still drying myself up I took another look at the showering guy, he was now turned sideways to me, still not paying attention to my presence. He was soaping up his body, with my eyes I followed his hands sliding around his body. Eventually his hands reached his cock. I noticed his cock was semi erected. He started to slide his slippery hand gently up and down his penis. I noticed that his cock was quite large, now that it was fully erected it was at least 18 cm long. He started to stroke his forehead only, his foreskin was pulled back completely. I knew about masturbation and technically knew how it´s done, but I had never done it to myself or seen someone else doing it. Internet porn wasn´t that far spread at that time, especially at schools and I where never cool enough to get a good look at those magazines, that got passed around at my old school from time to time. So I never got really experimentive with my occasional hard on. So seeing him pleasuring himself got me hooked. I kept watching him. He poured some more soap on his cock with his free hand, while continuing jerking his forehead with his other hand. Even though I couldn´t here him over the sound of the shower, he sure looked like he made some grunting noises. He started to stroke faster and faster. Suddenly I noticed how my own cock got stiff. Quickly I put my towel on it to hide it. Doing that, I couldn´t resist to rub the towel agains my stiff penis a bit, pretending to dry my privet area. It felt nice, kinda ticklish. I looked back at him. He was still stroking his cock very fast, it seemed quite exhausting at this point. Additionally to jerking his cock he was now kinda twitching, meeting his strokes by making quick and small thrusts with his hips. Than he suddenly stopped, I froze too. Witch one hand grabbing the wall he threw his head back and kinda thrusted into his other hand, now holding still.
Now worrying about him, noticing me, I quickly grabbed my stuff and went to my room with my towel around my hips. I put on my pajamas and laid in my bed. My little dick was still kinda hard and I kept thinking about what I just saw. What fascinated me the most was what I had seen at the very end. I guess I envied him for his a****listic drive to pleasure himself. He must have known that he wasn´t alone in the room, but he didn´t care. He wanted to pleasure himself and he did, he took what he wanted, I never could do that, I did´t have the courage. The amount of pleasure his body expressed kept going through my head. I closed my eyes and saw him again in my mind. I saw him in those last few moments before his orgasm. He is sliding his hand up and down on his cock, all the soap making it slippery. I hear myself breathing heavy. Without thinking about what I am doing, I start to touch my body, reaching under my pajama top with one hand, caressing my tummy, gently fondling my boyish breast and nipples. My other hand finds its way into my pajamas pants. I start to slowly stroke my dicky, using my foreskin to glide over my forehead. The water is raining onto his body, his hairy chest is soaked in water, I remember him having a muscular body. I feel inferior, my breathing gets even heavier and faster, I intuitive start to move my hips. But not in thrusts like he did, I make slow, circuiting movements, stroking my cock faster now. His lags muscles are clenched from the effort he puts into thrusting into his own hand. He grabs the wall and throws his head back. I stroke my dicky as fast as I can. Now he is making his finale thrusts, satisfying his basic needs, he gets his relief and empties his balls onto the floor of the shower room. I let out a tiny moan and arch my whole body, experiencing my first orgasm, I shoot my load on my stomach and immediately smear it all over my smooth and hairless tummy, still orgasming. For a second I get the urge to lick some cum of my hand, but I hesitate and the urge passes. I curl up into a ball, holding my now flaccid cock and my balls in my hand, twitching a little. After my breathing calms down to normal, I get up, go to the bathroom, and clean myself up with a towel and some water. Then I go to bed and quickly fall asleep.
Mhairi
- 02.07.2022
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- 0
