Crossdressing & ME: How I became a Sissy 3

So, having learned to masturbate and basically being the "Leader of the Pack" because I had taught all my horny friends how to jack their dicks, I began to host little "Sex Parties" on the weekends at my house...My mom was an alcoholic and seldom home, so we could do what we liked. We began to explore one another's bodies, so tender and youthful, so winnowy and innocent. We began by simply jacking off together, then touching one another's hard cocks, then learning to kiss. None of us were interested in "icky girls" at that time. We all knew they didn't have the equipment we had, so easily accessible and so hard! We rubbed cocks together, kissed each other's hard-ons, sucked each other off, and tried valiantly to fuck, but not knowing about lube we did not get very far. So we fucked pillows as others watched and cheered us into having orgasms. Hairless, lovely boys all having wonderful fun together on my mother's couch. We spent hours inventing sexual games. Every week another friend would have come up with something new! It was an exciting time. About that time is when I found my mother's underwear was extremely exciting to me...smelling it, wearing it around so my hard little cock would jut from the pretty satin or silk. It felt wonderful to my cock and I began to use her panties, almost always her dirty ones which smelled best...to jack off into. Now my cum shots were getting way better and messier and I tasted it. It reminded me really of bleach. Salty bleach. I thought "Too bad it doesn't taste like cream!"

That year was very hard on me as my mother went into the hospital for cervical troubles and we were shunted off to some relatives, all my friends gone and I did not dare try any of my new techniques with my Aunt's k**s, not knowing if they might tell on me. I had no idea they were actually being abused by my Uncle! They knew more about sex than I did! But we never got together on that as I was probably three years younger than them and a stranger. Plus their sexual experiences were frightening and i****tuous in a bad way. So that long summer past uneventfully and when I returned home I was an unhappy c***d. I had used my aunt's panties to masturbate into and was starting now to take an interest in girls. Especially older women. Their smell and the thought of them undressed was always stimulating. But so was cock! When I got home we went through the winter and I had lost all my old friends. Then we moved to innercity Chicago. There I found Hard-Core Porno under my Step-Dad's bed...men and women fucking, especially black women being fucked hard by white men. I was pounding my pork now three times a day to this stuff! These photos showed everything imaginable. Then I even found porno pictures of my Mom in an old suitcase! She was shown spread, in all manner of beguiling poses, and also showed my Step Father fucking her little pussy with his big, fat cock, and many shots of him with a raging hard-on! I began stroking off in my Mom's panties a lot...and wearing her bras. That Halloween as you can see from the first picture in the series here, I dressed as a girl for the first time. Also I had began to take babysitting jobs around my apartment. I always babysat my brothers and sister anyway and I could make 50 cents or a buck or two a night sitting for other folk's k**s. I sat for a little girl who lived in the basement apartment, named Stephanie. Her mom was a big, not very attractive woman. But she had these fantastically complex bras and girdles and big panties that just turned me on so much! I loved masturbating with them, trying them on and looking at myself in the mirror, pretending I was a girl being loved and sexed up by a man! I loved sitting for her k** because the k** played alone in one room and usually slept, and I had the run of her mom's dirty clothes hamper filled with her pheromone scented foundation garments! She had a lot of my seed all over her undies for a good year.