How I became a sissy.

This all started when I was in 4th grade. All the boys in the street used to get together to play in the afternoon when an older boy suggested we go play in an unfinished housing project. Once we got there he suggested the older boys fuck the younger boys. There was initial resistance from us younger boys but the older boys divided & conquered us by choosing one & taking them to their own room. I nervously pulled down my pants & let this older guy fuck me. His cock felt so weird but stimulating in between my butt cheeks. Penetration felt unlike anything I had experienced, almost fulfilling. This continued for maybe 45 mins, till we younger boys swapped older guys. We got fucked for maybe 3 hours & then went home & we never spoke about it.

A few weeks later while playing at one of the younger boys place the same older boy that suggested we fuck each other started touching my small penis. This caused an erection and if you remember those rock hard 4th grade erection you know it was not going down any time soon. He told me I want to be fucked because I am horny. I resisted while he told the other boys that it is time for fucking again. The other younger boys semingly did not hold up much resistance and proceeded to the back of one of the younger boys wendy house. I watch the other boys get fucked and I pulled down my pants to reveal my girlish curves & all the boys told me I have girl hips. Two of the boys came to grab my ass & told me its soft. Before long I was on my back watching a man pump my sissy ass. Even though I did not consciouly know it, this is the moment I truly became a sissy.

One of the younger boys, lets call him Matt, were good friends & we had both been fucked by the older boys that lived in our street. This included his older half brother. One afternoon Matt & I were playing at his house when I suggested we try what the older boys did to us and he accepted. He took his pants off to reveal the smallest stub penis I have ever seen. I would say it was less 1.5 inches when hard. He fucked my ass but it left a lot to be desired. His cockhead is the only part I could feel inside me. When it was my turn to fuck him with my 4 inch cock, he gasped as soon as I slid inside him. I thrust his chubby ass as hard as I could while he held in his moans. We took turns fucking each other until our dicks got sore. This would continue for 3 years until high school.

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Anonymous

by Anonymous

I was very young the first time I let an older boy talk me into getting naked with him and after playing with his dick he fucked me. I put up some resistance at first but once he had me on my stomach and he was on top f me rubbing his hard dick on y ass I relaxed and just let him have his way.
It hurt and he couldn't stick it in my young tight asshole but after spitting in the crack of my ass several times he pushed his way in to my ass and I will never forget the way it felt to be penetrated. It hurt quite a bit but at the same time I knew I liked it and the deeper he went the better I liked it and once he started to fuck me I knew I like it so I just moaned and pulled at the sheets while he fucked my ass and when he said he was going to cum I figured he would pull out but instead he shoved it all the way in and thrust it up my ass as hard as he could and he came in my ass. It felt very good and I liked how excited he got so I got even more excited and he never really stopped fucking me and really fucked me hard for a very long time before he came in me again.
I remember him laying on top of me breathing hard moving his dick in and out a bit as it went soft and I felt it slipping out of my cum filled young asshole. Shortly after it came out I felt his cum begin to trickle out of my ass and he got off of me and went to the bathroom. I just laid there with cum dripping out of my ass wondering how this happened and if it would ever happen again.
A few days later while his parents were at work I found out. I was naked face down on his bed with his big dick balls deep in my ass and he fucked me good and came in my ass again. At least once a week if not several times a week he would fuck me and after a few months he began inviting his friends over to fuck me and for several years I had quite a few older boys fucking me all the time Whites blacks and Hispanics and getting group fucked was pretty common. No wonder I still enjoy an occasional fuck in the ass after all these years.

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Anonymous

by Anonymous

We had been masturbating each other . We were both 12 . One day i got his pants down , and kneeled betweeen his thighs .To masturbate him . I decided that i wanted to have his penis in my mouth . So i leaned forward and put my mouth round him . Moving my mouth up and down , and using my tongue . I could see that he was enjoying it . Then he was cumming , his cum was filling my mouth . It made me swallow . So i was drinking his cum . When he had finished cumming , i asked him to do it for me . He gave me my first blow job , he let me cum in his mouth . Then he spit it out . Now we played with each others penis , also using our tongue to lick the shaft . Finishing by giving ech other blow job . Then one day he started talking about fucking each other . He wanted me to do him first . We used vaseline . After the first feeling of sliding in to him , i was enjoying it . Soon having an orgasm . Then he did it to me . Now if we could not be in his or my house . We would be in the woods , giving each other blow jobs . Too scared to fuck each other . If we were in the house , it was always fucking each other . He was the only one that i did this with . After him , it was always girls .

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