This is back in the 70’s, I was probably 12 or 13 and with my school friend Carl we used to ride back to school in the evenings (3 or 4 miles away) to go swimming at the sports centre. I remember we were getting changed in the cubicles when Carl called out to me to look. What? I thought, and climbed onto the bench to look into his cubicle.
He was stood there naked and with his huge (even at that age) rock hard cock in his hand, stroking it. I just said something silly and got back down and carried on getting dressed while he laughed. Obviously we were much younger, but if his cock was on a full sized adult I would reckon it was a serious 8 1/2 inches at least and thick. And of course at that age cocks are as hard a steel (i miss those days). Nothing was said about it, it was no big deal.
My cock barely had a hair on it and at that stage was still like a little boy cock. I was both jealous and impressed with what i saw. A few weeks later after games at school, we were all either showering or getting dressed when the teacher came along to hurry those boys still in the showers out, he chased Carl out who was proudly sporting a fucking huge hard on. We all laughed with him, it was not something we ever made any fun of him for, I guess with a cock that big (easily 3 inches bigger than any other of my friends and very fat) nobody could make fun of it!
Anyway, back to that original swimming session here’s what i wish i had done and how I imagine it all spanned out over the following weeks and months. So Carl called me to “look at this”, I climbed up on the bench and looked down seeing his huge hard cock and said wow. I’m coming down, i want a closer look at it. I quickly jump down and open my cubicle and knock on the door to Carl’s and he lets me in. His cock proudly and massively bouncing in front of him. He takes hold of it and gently strokes it, pulling the foreskin back. Can i touch it? i ask, Sure, he says.
I reach out and touch it and it’s so hot, i grip it and feel it bounce and bob in my hand. I gently pull the foreskin back. I cannot describe how turned on I am. i had wanked myself before, but it really only took a couple of fingers and my thumb. although i could not cum, i just had a nice feeling. But with Carls cock it took my whole fist to grip it. I knew that this was like a mans cock and that surely Carl could cum, something I had never seen. Take yours out he says, Ok but it’s tiny, nothing like this. I lowered my trunks and my pencil thin little cock stood up straight and hard. He said put it next to mine and I did, it was not even a quarter as long or thick. I started to stroke his cock again and I just got onto my knees so i could be closer to it. With one hand i stroked his hard cock and with the other hand i stroked mine. My fingers did not even reach around his cock and I was using my whole hand. With my own I was just using 2 fingers and a thumb to grip myself and of course my fingers easily overlapped.
After a couple of minutes Carl said yes and i felt his cock harden even more and cum exploded out of his cock all over me in 4 or 5 big long spurts. I had never witnessed that before and it was amazing. I guess i could have just grabbed a towel and wiped myself with it. But, instead i used my fingers to play with it and rub it into my body, it was all over my chest. I rubbed my hand through it and then used it to lubricate my cock as I wanked myself to the nice feeling.
I told Carl that was amazing and I would like to do it again. Over the next few weeks every time we went swimming it followed pretty much the same way. Whilst getting changed my little cock would get hard thinking of Carl’s monster and then we would swim, again often i would be sporting a little erection in my trunks. And then in the changing room, At some stage I would join Carl in his cubicle and would soon be stroking his beautiful cock until he came all over me.I used to try to aim his cum at my cock so that when i wanked myself it would be super slippery.
A few weeks later I was at the pool on my own as Carl was unwell. And I was just standing in the shower imaging Carl’s big cock when a man came in. He wasn’t very old maybe 18-19 but to me at 13 that was a man. He stood under the shower next to mine and soon slipped his trunks off. His cock although soft was still big, not as big as Carl’s, but as i was to find out over time, very few were.
His cock was soft but I could not take my eyes off of it and I was watching as he started to soap it and his ass. I could not help but pop a boner. Luckily I still had my trunks on, but I am sure he could see the little tent pole. He soon started to stroke his cock as he asked me if I was going to take my trunks off. I could not tear my eyes from his crotch. No, i said. Why not? You need to rinse the chlorine out of them. I guess he was right but my cock was hard and I did not want to show it. It’s OK i said. His cock by now was a solid 7 inches. You like looking at my cock don’t you. I didn’t know what to say, he moved closer to me, want to touch it? I said nothing, he soon grabbed my hand and put it on his cock. I could not help myself, i started to stroke it. he reached out and pulled my trunks down, my little cock jumped up. Nice he said, although it was nothing compared to his. I was enjoying stoking his cock, he in return was playing with mine.
We heard a noise and he said we better do this in a cubicle, in case we get caught. I followed him to his cubicle and he pulled me in. I started to stroke his cock again. I got on my knees and started to stroke him, lick it, he said. I said no. He told me to do it. And pushed his cock closer to my face and pretty much forced my mouth over his cock. i pretended i didn’t want to but secretly I was thrilled to be doing it, I felt all grown up, my mouth was stretched to suck his cock, my own cock was throbbing and bouncing on it’s own. I could hear my own heart pounding in my ears. I stroked him and he held my mouth on his cock and gently fucked it in and out of my mouth. After a while I felt it expand between my lips as that happened he gripped my hair and then he spurted his cum into my mouth. I swallowed some of it and the rest spurted over me and at the same time my cock just exploded, cum flew out of my cock, as I had my first ever real wet cum without it being touched. I was so excited and overcome i almost passed out.
After, I recovered he thanked me and told me he hopes we could do it again. I was both excited and embarrassed. I decided i better have another shower as I was now covered in cum, his and mine. I put my trunks back on and left his cubicle saying goodbye. As I came out a man was sat on the benches in his trunks. I don’t know what he thought had been happening but the cum on my body obviously gave it away. I had not thought to take my clothes or towel with me so had no choice, I made for the showers and started to wash myself down. The man followed me in. He was older, much older probably 40, quite fat. He stood next to me and soon said what have you been up to? I said nothing and he said, hmmm looks like you have been a very naughty boy.
About that time another man came into the showers. he was probably early 30’s, unlike me and the older guy he just dropped his shorts and his cock was dangling a good sized cock, he was quite muscly. Hello john he said to the older guy, alright Gary the older guy replied as he also dropped his trunks, his cock was not very big or thick but it was hard and about 5 1/2 inches long. Whats got you excited? Gary asked, Oh this young man just came out of a cubicle covered in spunk. I think he has been having some fun. Really said the one known as Gary. And he took the shower on the other side of me, his cock visibly hardening. I was not sure what to do. When he told me to take my trunks off. i said no, but he just grabbed them and pulled them down. My cock once again betrayed me as it bobbed out hard and ready for action.
Oh that’s a nice little cocklet for a youg’un said John. Gary took my hand and pulled it onto his big hard cock. I automatically started to wank it. Looks like he knows what he’s doing said Gary. Gary pulled me down bending me forward and pushed his cock against my face. John came behind me and reached through my legs grabbing my hard little cock and pulling it down. I was trapped between them. Hoping nobody else would come in. At the same time, I was kind of excited that these men wanted me. Gary pulled my head onto his cock and John still holding my throbbing cock down was rubbing his other hand over my ass, soaping my ass and cock. I felt his cock between my legs. Luckily it was the smaller cock. I felt him pushing it at my virgin ass and I panicked but i could not get away as my mouth had Garys cock in it and John gripped my hips tightly.
Don’t worry he whispered you will enjoy it and I will be very gentle. He slid a finger in my ass and wow it felt amazing, I felt my cock throb and so did he, mmmm you like that. Over the next few minutes he worked 2 then 3 fingers in me before finally putting his cock head at my ass and pushing in, It hurt, a lot, but soon the pain subsided and I was in such ecstasy. Gary had taken his cock from my mouth and he watched as John fucked me like a little girl. Do you like that he asked. Yes, I said, yes. Good. lets go back to my place so that we can do it somewhere safer.
I didn’t hesitate, I said OK and with that John gripped my hips and started ramming up my ass faster and harder and then I heard him gasp as he gripped me tightly and pumped his spunk up my ass. I felt his cock throbbing as it pumped his warm cum inside my ass. Sorry, he said to Gary, I just had to fill that ass. Anyway, it will ease the way for you later. Lets go back to yours. I got dressed and they put my bike in the car promising they would drop me home afterwards. It was probably a stupid thing to do, but I had decided to grasp the opportunity for sexual adventure.
We were soon driving to Gary’s house, I got a shock when we walked in and a pretty women was there. Around Gary’s age and obviously his wife. I have brought you a little toy he said. Oh goody, let’s play with it then. She grabbed my hand and I was dragged upstairs, with him calling after us, he’s a sissy, I didn’t know what that meant. This is it i thought, I am going to fuck a women. I was soon to be disappointed, So, you like a nice mans cock do you? She asked me. I said nothing. Shy huh, well let’s get you dressed shall we. She made me strip off my clothes and i stood in front of her with my little cock straining to reach the sky. Oh that’s no good, we cannot have that. She pulled a pair of stockings up my legs and connected them to a suspender belt all the while my cock was bouncing in front of her begging to be touched. Then she pulled some lacy panties on me. She tried to pull my cock down to between my legs but it would not go down and the more she was touching it the more I felt I was going to cum. She gave up and left my cock pointing upwards encased in the panties. She then pulled a small mini skirt and on the top she put on a what i now know to be called a basque. She put a wig on me and then did my make up.
I was passive, i did not know what i was doing there and I knew i could not just leave. She made me stand up and then she put some girly shoes on me, with quite high heels, I could not walk in them. She led me to the bedroom and she stripped off, her big tits bouncing in front of her and her cunt covered in a fine blonde hair. My cock if possible was even harder, Ok lie on your back the women said, I did as told, my cock fit to burst with the anticipation.
OK, she had dressed me like a girl that was weird, but I was going to fuck her! And she then put her cunt over my mouth and told me to lick her. I was not sure if I wanted to do that, but she just pushed her cunt onto my face and soon the beautiful smell of her sex and the wet softness of her cunt, both things I had never experienced before had me lapping away at her wonderful tasting cunt, I liked this, my cock was bouncing on it’s own. I was willing her hands to stroke me. Then I heard the two men coming into the room. Gary said you have him first to loosen him up for me, but don’t cum this time, save that for my wife, he can clean the creampie.
With that, I saw Garys cock looming above my face as he slide it into his wife. I then felt hands on my legs rubbing tthe stocking tops and onward to my knickers with my cock bulging for release. I was licking Garys wife as his cock was sliding in and out of her cunt and my tongue was occasionally licking his cock. I then felt john ease lubricant into my ass and soon it was followed by his cock, he was fucking me slowly and gently and it was lovely, I felt nothing but pleasure and I am sure my cock was slowly leaking a continuous stream of pre-cum. He kept stopping as I approached the point where I would cum, Dam, I can’t keep this up, I’m going to cum he said.
OK stop, here, take over fucking the misses and be sure to fill her up with your cum, so our young lady has something to lick clean. Soon John’s cock was above my face, sliding his much smaller cock into Garys wifes cunt. And then I felt Gary probing at the entrance to my ass with his much bigger cock and I felt it forcing its way into my ass. I just sighed and my cock started squirting cum uncontrollably into the air, fuck said Gary, that’s the hottest thing I’ve ever seen, our little Sissy just cum hands free when I slid my cock up her. John also came into Garys wifes cunt around the same time, pulling out and forcing his cock into my mouth for the last two spurts. As he pulled his cock out of my mouth, Gary’s wife pushed her cunt onto my face telling me to lick her clean, clear up the cum, she said.
Gary’s continued to fuck me, his huge cock was causing me so much pleasure, my cock was throbbing and bouncing, hard again and then I felt Gary really push his cock hard up in my ass, he was groaning as I felt his cock throbbing and pumping his liquid into me and I had accepted my second load of cum. You are a naughty little girl said his wife as she got off of me. We all lay on the bed and Gary’s wife ‘Jane’ pulled my face to her soft breasts and told me to suck her nipples. I enjoyed stroking and playing with her big tits. Being young of course, my cock was soon hard again. She told me normally if Gary brought any boys home she would let them fuck her but as my cock was tiny she did not think it would be worth the effort, and I am sure she would not have gotten much pleasure out of it, especially after Gary’s monster, as she was saying this she was stroking my little cock between her fingers and her telling me I was so small and was meant to be a sissy just seemed to tip me over the edge, I spurted my cum high into the air some of it landing on her tits, lick it off she said to me and pulled my head onto her breast, I licked her clean, feeling her big juicy nipple in my mouth.
A bit later they dropped me off as promised and told me that they would love to see me again. I decided not to tell Carl about it, but I had decided that if I get the chance I would like to suck him and have him fuck me. We would have to find somewhere safer than the cubicle at the pool. For the next few days he could not go to the pool as his bike had a puncture. I was quite excited to go on my own again and see what adventures I could have.
part 2 to follow
Source: reddit.com/r/sexystories/comments/clyitn/teen_becomes_a_sissy_part_1_fantasy_sissy_gay
Dayum.
That was hot.
Very nice
that escalated quickly.
Gary has a good wife.