My first summer as a crossdressing slut

How my older cousin turned me into a sissy in one summer.

My story really started with my cousin Joey. I was spending the summer with my grandmother when I was twelve. My first cousin was 14 and he came to stay as well. About one week into the summer, Joey and I were sleeping in the same bed. He taught me how to masturbate. Actually I could feel him moving around and doing something, and when he finished, he said “Feel this.” He guided my hand to his stomach where I felt something wet and sticky. He called it cum, and then he proceeded to tell me all about jacking off. Well, I took to it enthusiastically, and the very next night, all alone in the bathtub, I stroked my hard little dick with soapy water until I had my very first orgasm. I was hooked. It was fantastic. Joey and I would go swimming at a creek behind my grandmother’s house and sometimes at a nearby pond, and we would swim naked and sit on the bank and jack off together. He could always finish before me, but watching cum spurt from his hard cock, which was somewhat bigger than mine, always got me where I needed to go. Since our grandmother worked as a nurse, we were left by ourselves during the day, and we sat around the house using her hand lotion and jacked off a lot. Once down at the pond, Joey decided that we should try to fuck a cow (there were several around), but we never accomplished it. One day when he was particularly horny, he wanted me to lie down and let him get on top of me…just to see how it felt. I was reluctant, but I eventually let him. He laid down on me and humped a few times and then got off. Then he suggested that I lie on my stomach and let him try, so I rolled over onto my stomach and he got on and began to hump against my butt. I could feel his penis getting quite hard as it bumped against my crack, and then he took his hand and moved it so that it would slide between my thighs just up under my balls. He began to “fuck” this crack between my legs, and in a very short time he was cumming all over me. I found it very exciting! About a week later, Joey persuaded me to dress up in some of my grandmother’s underwear. I tried on several of her panties and bras (which were all much too large for me), and I even tried a long-line bra and a panty girdle. I had an incredible orgasm jacking off with that panty girdle on. Before the summer was over, it became a regular routine for me to dress like a girl and suck Joey’s dick. The first time I was quite nervous, but i very quickly got turned on by doing it, and in no time at all I was a very experienced cocksucker, and I would swallow every drop of his delicious cum. Joey never did fuck me that summer. We never quite got to that point although we came close. But it was the beginning of a lifelong fascination with crossdressing for me and the first steps for me wanting to become a girl.

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