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Caught and used
I was a boy who secretly wore my sister's panties and dressed up in her clothes. First sexual experience was dressed in her clothes. I was horny and getting ready to masturbate and had crouched down to do that and also was going to use one of her tampons anally while I did. Instead, got my asshole licked by her dog and let him do that, then mounted. Not planning on sex, but he got his prick inside me. It felt better than a tampon. The sex was raw and rough while he fucked me and knotted, and I had a strong orgasm from it. I ended up using the tampon afterwards to soak up his fluids. He licked and fucked me several times in her clothes after that.
I started taking stupid risks and let him fuck me in our yard while dressed in my sister's clothes a couple times when no one was supposed to be around, but the neighboor kid came over and knocked on the door when I was home alone one day. I had seen his mom only a couple times before. They were complete opposites. She was pretty, blond, and white, but he was black and ugly. He was about a year older than me. Some thought she had been raped, others thought she had just been wild when she was young.
Well he didn't just decide to come over to say hello that day. He asked if it was just me home, I nodded and he pushed himself inside. I tried to protest, but he told me he had seen me letting the dog fuck me. That shut me up. He told me what he had in mind. He must have known he wasn't going to get a white girl with his looks, but he liked the way I looked dressed up. In short, so for his silence I was going to be his bitch. He had me dress as a girl for him and put on my sister's lipstick and perfume then suck him. I wasn't any good at blowjobs and didn't like swallowing, but did what he said and he fucked me up the ass afterwards.
He came over regularly after that. My mom thought it was great I was making new friends. She probably thought we were going to my room to study or play video games, but we weren't. We were in my room, but doing none of those things. I was dressed up in my sister's clothes with some light makeup and perfume on my knees sucking him or bent over getting fucked to keep my black black-mailer quiet. His favorite outfit was my sister's old school uniform, but liked a few of her dresses too. Luckily he didn't have and sexual diseases, but that went on for at least a year till he and his mom moved away.
If my mom noticed makeup on me or that my room smelled like girl's perfume and sex, or the fact that I always quickly took a shower after he left or that my armpits and legs were shaved, she never said anything.
A guy I thought was my friend did much the same to me in reverse. We hung around a lot. I went over to his house one day, he had invited me over. When I knocked on the door this good-looking chick answered. It was him, and he'd gone all out, makeup, nails, sexy dress, he had really long hair and it was styled.
I know I was shock, but he grabbed my wrist and pulled me in, asked what I thought. I didn't know what to say, he just laughed and said he was the only one home and led me up to his room.
He told me how freeing dressing like this was, and he always felt like he was a girl. Honestly he got teased in school because he did have a very feminine body, not much on breasts, but girlie nipples and he had the curves and bum of a young girl, and he had a really small penis. Telling me that he felt that we were such good friends that he could confide in me, then he started to hug me and sort of rub on me and we looked at each other and then it happened we kissed. It wasn’t as horrible as I imagined kissing a guy would be. We made out for about half an hour and then our clothes came off. We did a little 69, again I was surprised that I did it. Then he wanted me to fuck him, I was like ok, and I was going to roll him over but he says wait, gets the KY out smears it on his butt, then lubes up my dick and says be gentle and guides me on top of him missionary. Once I got in him and started to pump, he wrapped his legs around me and arms around my neck as the whole time I’m pumping him all he wanted to do is kiss passionately. I came in him and that seemed to make him ecstatic. We lay there, I’m think what did you just do. He cuddled up alongside of me playing with my penis, kissing my ear and neck.
I started to say how this was a crazy thing, and he told me that if I didn’t come visit him, he tell everyone that I fucked him and we’d both be pariahs. I ended up fucking him about once a week for 18 months. I graduated and went in the service.