First Times are the Best Ch. 01

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.

I always pictured my first blowjob to start by sucking the guy's balls, but he had his hand rubbing his so I intended to start with his dick instead. I was still pretty nervous, though excited with all the anticipation. I grabbed his dick and felt the whole thing up and down a couple times. I looked up at him to see him looking down at me. I told him, "I've never felt another guy's dick before, I love the feeling."

He told me, "you'll get used to it."

I finally put my mouth to it. He moaned a little immediately. I felt the head in my mouth and started swirling my tongue over it. Then I started bobbing my head. He guided my head gently. I closed my eyes and put more concentration into it. I tried going deeper in my mouth but I gagged just a little. He said, "hold on."

I removed my head from him as he stood up. He pulled his pants down to his ankles and sat back down in one quick move. He grabbed my head and guided me lower, and told me "start sucking these."

I extended my tongue, and licked between his balls. I tried to get one of them in my mouth, but to not avail. His moans were noticeably louder when I licked them.

I continued licking his balls for a minute or so before continuing on his dick again. He said, "stand up for me."

"OK," I said as I stood up.

"Take off your pants, if you don't mind. Get comfortable."

I started by taking off my shirt. He reached for my chest and felt around. Then I took off my pants with relative ease. I saw him notice the panties, to which he just smiled. He stopped me there, and pulled me toward him. He put his mouth on my left nipple and started sucking. I wrapped my arms around him. He took his hands and put them on my ass. He started feeling up and down.

He turned me around and pulled the panties down to my knees. He said, "you have a nice, feminine bubble butt," he said. If you come over again, we'll go a little further." He then stood up, and I felt his dick between my ass. "Go back to what you were doing before."

I felt dirty but pretty turned on having the panties around my knees at this point. I kneeled in front of him again. This time I licked his balls right away. His moans gained some momentum, and then I went to bobbing my head on his dick. This time I tried doing it with much more confidence. I went faster and a little deeper. I tasted the saltiness of his pre-cum.

He said, "lick my balls again." I complied eagerly. He stroked his dick for a minute or two while I was doing that. I was really into it at this point. He whispered, "I'm going to cum!".

I wasn't sure what to do! I hesitated and felt a little get on the very top of my head. I opened my mouth wider and got into position to catch it in my mouth. I felt several large spurts of cum land in my mouth. I had the urge to swallow it right away. But I tried waiting until he was completely done, to show it all off to him as a badge of honor that I am swallowing all his cum. I looked up at him and smiled with a huge gulp. I ran my fingers through my hair to taste the little bit that escaped. I licked the length of his dick a couple times, which made him moan.

When I felt him go completely soft I stood up. We both got dressed. He asked, "how was it?"

"That was great. I wish I didn't wait so long to experience that." I went home, very content with myself.