Pegging, from Fantasy to Reality

Posted by AuroracloseAuthor: Aurora Name:
Email: genobeba_24@yahoo.com
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About: Sex is probably my favorite conversation topic, just ask my friends! I'm a budding sex educator, killing time until I can go back to school by figuring out who I am and what makes me happy. I'm a bi, poly, switch and wouldn't trade that for the world.See Authors Posts (2)

For the longest time, I couldn’t really understand why a woman would want to wield a dildo. Even though I knew I was bi from the time I was 16, I didn’t get the appeal. It certainly never to me, not even in my deepest, most secret fantasies, to consider using one on a guy.

And then, one night, it hit me. I was at a New Year’s Eve party with some friends, including a friend who I’d had sex with more than once who was also bisexual. He and I were talking and I was trying to get up the nerve to kiss him (yes we’d had sex before, but I get shy easy), when the image of me bending him over and fucking him popped fully formed into my head with no warning. The image was a surprising one for someone who’d never seen the appeal of a dildo, but the wave of wanting to make the image real was even more surprising. I told him about the image that was becoming a fantasy and he also thought it was a lovely idea and would be more than happy to participate when it was feasible.

That particular fantasy has yet to be fulfilled, with that lover, anyway. I let it slip into the back of my mind, to simmer and get all kinds of juicy and yummy as I didn’t have a dildo and couldn’t afford to get one at that time. Plus, the only ones I’d seen then were either one sided or just unattractive double enders that looked like they belonged in a porn movie and not my bedroom.

Eventually, I started dating another friend of mine, who is also bisexual, but with much less experience with other men and almost none of it being on the receiving end of anal. We shared a fantasy about my fucking him. We went shopping for a dildo that we would both like. I favored the Share by Fun Factory, since that’s what my girlfriend and I use together. He was very interested in being penetrated, but also very nervous. I was/am also a bit nervous about doing the penetration, but excited at the same time. Being asked to be his first was a huge honor.

We set the scene by going to a hotel for the night. After dinner, he wanted me to cut his clothes off of him. It was…deeply erotic. The slide of metal on skin, the parting of the cloth, exposing more and more skin, until he was naked beneath me. Sometimes knife, sometimes scissors, sometimes ripping with bare hands.

And then, once he was naked, the real fun started. I got out the Share and slid the shorter end into myself and asked him to give me a blow job. It was mesmerizing, watching him slide his mouth down the length of the cock between my legs. The visuals alone were mind blowing; if I’d have been able to enjoy the sensation as well, I couldn’t have stayed standing. It got to the point that I couldn’t not fuck him, so I set about doing just that. Lots of lube, lots of working him until he could take enough of my fingers that I felt comfortable bringing the dildo into play, then, finally, insertion. I would love to be able to say that it all went off without a hitch, but that was not to be. I couldn’t really keep a hold of the Share and had a hard time thrusting, since I was soooo not used to being on that end of the cock. We tried several position, because even with the fumbling it was still deeply hot. There was so much love and need and trust in that room, it would have been impossible to not keep trying, no matter what we had to try to overcome. In the end, we had to give up on my fucking him to both of our wanted end, but we still had an enormous amount of fun and are looking forward to trying it again, now that I have a harness to help with the holding on.

I still have that first fantasy, the one that came from no where, floating in my head. I’m still friends with the man who figures so prominently in it, ass up and waiting for me. I have hopes that one day, I’ll be able to fulfill that fantasy and see if the reality matches the dream…