This was a fantasy of mine for a long time. I had fantasized about men's dicks off and on for a long time. I even got off on some anal toys eventually too. But I never had the opportunity or knew where to look for a real guy trying to get off. For a while it grew into me fantasizing about men while looking at pictures of hung guys' dicks and guys getting blowjobs from women.
But when I realized there were gay ads on craigslist shortly after becoming single I found my opportunity. I found a simple post with the title "Top needs to get off". The post itself had a picture of a dick, which was about 8", a little more impressive than mine. The description said something along the lines of "Looking to host tonight. Be D/D clean, prefer thin/fem.".
I pictured myself sucking, licking it, etc.,. I figured I'd better go with it and see if I really am missing anything. I e-mailed him with a picture of myself just telling him I was interested. He quickly responded with his phone number and just said to call. I was so nervous I could barely dial the number, but I managed. He said "have you done this before?"
I said, "no."
He continued asking, "are you sure you want to do this?"
I said, "yes." I hardly said anything on the phone. We agreed to meet at 9:00. He gave me his address and told me to call if I get lost or anything.
It was 7:00 now, so I had a little time to prepare. I hopped in the shower right away. I thought to myself I want to be as feminine as possible. My pubic area was already shaven, so I started to shave my legs. It was tougher than I expected, but I got most of it done. When I got dressed I put on a pair of panties that were left at my apartment from an ex. Over that I put on some tight jogging pants from when I was younger and a tee shirt.
I left for his place around 8:15. I knew it wouldn't take that long but I didn't want to be late. I found his apartment pretty easily, which was in a pretty rough area though. I was pretty nervous about the situation. I was thinking of all the things that could go wrong or why I might regret this. I left all my stuff in my car, except for the keys, and locked the door. I knocked on the door gently. He answered immediately, thank God. He had some jazz playing, and looked to be quite a knowledgeable reader judging by the number of books filling all the walls. He introduced himself as Jason. He was a pretty average looking guy, wearing business casual clothes. He asked, "do you want a beer?"
"Sure."
He brought me a Heineken and we both sat down on two separate couches facing each other. He asked about where I'm from, what I do for a living, etc.,. He touched himself now and then during all this small talk. I kept thinking of that picture of his dick. It felt like foreplay to me, but I wasn't sure if it was suppose to be or not. After we finished the first beer, he asked, "so what made you realize you want to try this?"
I quickly answered him something about my fantasizing about it. I was trying to predict where it'd go from here. I asked about him.
He said, "my friend growing up told me he's gay in high school. He sucked my dick and I've been into it since. Are you single?"
I answered, "yes." I wasn't sure if he was considering dating me or what. But I asked, "what about you?"
"No, my fiance lives in a different state. I'm just here temporarily for work. She has no idea. So how about we do this." My heart jumped having heard this. He started undoing his belt. I took this as a cue to get into my position. I got down between his legs and on my knees, kneeling in front of him. He pulled it out. It was already big and hard.
