I saw the above photo, and the memories came flooding back. The picture is not of me, but it might as well be. It perfectly captures a moment in my life, a rite of passage (in more ways than one).
As a stutterer in high school, I wasn’t one of the cool kids. As a matter of fact, I was the butt of a lot of jokes by the mean girls that every school has. But as a girl blossoming into a beauty with a round, prominent, callipygous butt, I was the object of attention of a group of horny boys. One of them, Tom Logan, invited me to prom. We hadn’t dated at all before that auspicious night (I hadn’t dated much at all). My prom was probably a lot like yours, my folks bought me a gown, he bought me a wrist-corsage, both sets of parents took lots of pictures, he took me out to dinner, we went to the dance, then we went out afterward. It was not respected if you came home before dawn. Tom took me to a secluded parking lot overlooking the lights of our city. It was very romantic, so I didn’t mind getting steamy, letting him kiss me, letting him fondle my tits. Because I was even more randy then than I am now (with teen-aged hormones raging), I started fingering my pussy through my dress.
“God, you’re sexy, do you know that?” he exclaimed when he saw what I was doing. I blushed. “Do you know you have an incredible ass?”
“I know a lot of people think so, for either good or bad…” I demurred.
“Let’s get in the back…” he suggested, so we clambered into the back of his mom’s SUV. He helped me pull my gown off over my head.
Now, up to this point, I’d never taken a man’s penis into my mouth, I hadn’t had my V card stamped. But Tom didn’t seem interested in any of that.
“Can I see it?” he whispered tremulously as he caressed my bottom through my fancy satin panties.
I got up on all fours and pulled them down. Tom caressed me so lovingly, looked at it so longingly. I felt more than appreciated, I felt adored. I got his erection out of his fly and started jacking him off inexpertly.
Tom lurched “You can’t do that and not let me get off!” Suddenly it was all my fault that he had blue balls. But I was excited, too.
“Do you have a condom?” He nodded affirmatively and got a foil packet out. We both put it on him. He was trembling, his cock was throbbing; I felt like royalty for inspiring these reactions. My bottom was all-powerful.
“I don’t want to get you pregnant…” he breathed.
“I don’t want that either,” I agreed conspiratorially.
“Let’s put it in… your… butt…” he whispered seductively.
“You can do that?”
“Yeah, some girls prefer it… because it’s safe.”
I continued to finger my pussy. I wish I’d known enough to suggest fingering some of my copious juices up my backdoor, but didn’t. Tom didn’t seem too knowledgeable either. We made up for our combined ignorance with enthusiasm. That’s where the above photo comes in. That must have been exactly what I looked like as Tom introduced his hard cock up my tight anus, introduced me to the world of butt fucking. It hurt, but I knew that taking one’s vaginal virginity was supposed to hurt, so thought that this was the same. It also was compelling. I felt like an outlaw, letting him do this, wanting him to do this. Apparently, Tom found it highly-charged, too. After just a second, he groaned loudly and withdrew from me. The rubber stunk, but we didn’t care. I didn’t see any shit or blood streaks, but I didn’t inspect it. We were both awed by the prodigious load of spunk making the condom droop heavily at the tip. I’d done this to him, my tight little butt hole up my big bottom had done this! I kissed Tom passionately.
At school that next Monday I felt different, I felt like a woman. Tom, in his elation, had to tell this news to his best friend. So, of course, by Monday afternoon, I had the widespread reputation as a girl willing to take it up the butt. Lots of guys showed lots of interest in me from then on. I didn’t date a one of them. I waited until I went away to college to let another man know me in the Biblical sense. Kevin took my vaginal virginity, and the next night (at my suggestion) revisited fucking me up the butt (this time slowly, gently, with lots of lube). I loved both experiences equally, have done both eagerly ever since.