[connie]

When I was a freshman in high school, I discovered my love of being anally penetrated. I had been dressing as a girl since 8th grade, and had an interest in being female even before then. I read about being fucked in the ass in my uncles porn mags and books, and decided to try it myself. I started small, in my bed at night, dressed in my quickly purchesed panties and nighty sets, fingering myself, and it felt so wonderful, I would masterbate to a great orgasm, and then change before I fell asleep, so my mother would not find out when she woke me in the morning. I moved up in size, with veggies, squash, cucumbers, carrots, all carefully washed and fitted with old condoms my late father had owned. It was wonderful, on my back with larger and firmer objects slid up my bottom, my long legs spread in the air. But it was still not quite real, it was not sliding in and out of me, I wanted, needed that action, that movement. I soon ordered,(thank god for the mails and ads in porn mags), a realistic large vibrated silicon dildo. Then I learned the pleasures of riding a cock, I would set it up wrapped in clothes to steady it, on my bed then straddle it, sliding my hot little ass up and down it's length while it buzzed away. The first time I did it all successfully my orgasm shook my whole body, and I knew I needed that feeling as much as possible. So by freshman year, it was pretty clear that I would never be a macho boy, and my mom was okay with that, she saw the painted toenails, (fingernails were too far though), the longer hair, the interest in makeup and female clothes, but she loved me and wanted me to be happy, but to be safe as well. My mom's best friend came to visit, and she had a son who was a sophmore in high school, I won't say we hit off, but I adored him, he was so beautiful, and he saw someone who would satisfy his never ending need for sex. I learned so much during the month they stayed with us. For at least three weeks, not a night went by that his cock wasn't in my mouth, and wonderfully, in my ass. Here is how it happened, as he was staying in my room, it soon became apparent that I could not act nor dress as I usually did, but we all have drives, and mine was huge, and as soon as I was certain he was asleep on the third day, I stripped down to my panties, (I was wearing jammies), pulled out my nighty, and began to slide my favorite toy into my ass, I tried to be silent, did not even turn it on, but he caught me, and instead of telling on me, or being shocked, instead he began to hold me and kiss me, then he asked if I would go down on him, I had never done so, but tried it anyway. He taught me what he liked, and then came in my mouth. I liked it, not the flavor at first, it was a little strong, but him coming in my mouth,that I liked. Then he asked if he could fuck me, it was a dream come true, a real person fucking my ass. It was wonderful, I was still wet with lube, but when he slid his hot cock in my ass, slowly, it still hurt a bit, but inch by inch he slid into me, when he finally got it all in, he began to pump me, slowly at first then harder and faster, until finally he came in my ass. I did not even have to touch myself, I exploded all over my nighty and the sheets. He fucked me every night after that, and anytime we could be alone, but only if I were in female attire, panties at least, if not more. He loved lipstick on me, and so did I, so his cock was soon red from base to tip. He and his mother soon left, and he did not pretend that he loved me, nor that he would write, I was just some girl he had met and fucked for a month long vacation, that I had a penis was just a detail. That is why I love a hard cock up my ass, because it feels wonderful. Sorry this is so long, but someone asked for first time stories, and this was mine.