Building up to my First Experience with a Guy

I had always considered myself to be straight growing up but like many other guys I was curious what it would be like to have sex with another guy. These feelings just started as a fantasy when I was younger, jacking off thinking about playing with some of my friends in the neighborhood. I usually fantasized about getting fucked and taking the position of the bottom as I would later learn it is called.

My curiosity was strong when I was young but went away in high school so I thought I was done and had moved on from this phase of my life. However, I started watching porn in undergrad and the more and more I watched it, the more I started picturing myself as playing the role of the girl in the guy-girl porn scenes. After awhile I switched to watching some more gay porn but wasn't totally into it, I just felt like something was missing that was in the guy-girl scenes. So I started looking into gay sex and realized that most of the guys in the flicks were versatile and I solely fit the description of a bottom, wanting nothing to do with penetrating a partner but rather solely being penetrated by a partner.

With this new insight I got up enough courage to join a gay hook-up site and post a few messages as well as chat with some guys about my curiosity. After looking at my pictures they gave suggestions that they'd like to see me in some women's lingerie. I was really turned on by this idea because I thought it would really help me fulfill this fantasy of playing the women's role in the bedroom. So I bought a few teddiettes and camisole type outfits with stockings and the whole bit, and even invested in a nice 7" dildo, figuring I should see how I like that before I went any further. Needless to say I couldn't wait to get everything in the mail.

Once it arrived, I tried on the lingerie and took pictures to use for my postings, and went to work with the dildo. At first I thought I was going to give up my fantasy and be done altogether because the dildo was too much work to get in myself because I was so tight, but soon enough I was able to ease it in after a few attempts. man was I happy I didn't give up because I loved it, I used that dildo on a daily basis and it made me one step closer to the real thing, the only thing missing now was being able to suck a dick. Later I would learn that a dildo was not even comparable to how good the real thing was. After a few weeks of using my dildo I started to really search out my the top who was going to truly break me in as the bottom I wanted to be. Finally, one day I got a response from a person that I knew would be my first.

(To Be Continued) as "My First Time with a Guy"