I just turned 39 and am struggling with the big 4-0 when I knew I wanted to try something new. Skydiving or a motorcycle was not what I had in mind. For years I had thought about doing it with a guy but I am married and resisted the thought of 'cheating'. I had jacked off a couple of times with a friend and 17 and had thought often of that over the years. Even at that time I wanted to touch him but did not. Years of gym membership kept me looking but still never touching. This summer I got my chance.
I signed up for a work conference in San Francisco before I found out who else from my company was going. There would be only two of us, myself and Nathan, a coworker from another state. I had worked with him minimally, but knew one thing from another coworker, he was gay! I did not know if he was involved or not, if he was, did that matter? I just realized that I would be in San Fran, with a gay guy, it may be time to touch cock!
The conference started on Monday morning and I had planned in advance to go early and see the city for the weekend while I had the chance. Luck!, I found out Nathan had the same idea. We made arrangements to meet on Saturday after we got there. Okay, I will cut all the tourist stuff crap in the middle and get to Saturday night. He said he had plans to go to this gay bar he knew and to his surprise I said I would like to go along and see what it was like. He seemed guarded about this but agreed anyway. We had dinner and I managed to have several beers to get me a good buzz going before we headed off to his bar. When we go there, there was a decent crowd. I must say I wish picking up women was as easy as picking up guys seemed to be. I saw guys hook up and leave just by seeing each other. Some headed somewhere in the back and would be back shortly, others would just leave. I was getting drunk.
Nate and I were talking about work and other crap. He would be checking out the guys and I was looking around too. Guys were checking me out and that was making me hot. Nathan must have picked up on this and finally just asked if I was me... I remember the line like it was yesterday, "Hey, you seem to be having a great time here, are you BI?".
I just got a big smile and said, "Not yet". Of course that just opened me up to some questions where I revealed I had been wanting to see what guy sex was all about.
He said, "Hell, what are we doing here then, I can help with that, lets go", so we jumped in a cab and headed back to the hotel. In the cab, he took my hand and put it on his cock. I could feel it was nice and hard though his pants. I was the same way.
He took me back to his room. These was no time for awkwardness, he shut the door and started pulling at my clothes. At this point he knew I needed someone to take charge and he did. Soon I was to my boxers with a nice little pup tent. He took his clothes off next and was soon in boxers too. Then he dropped to his knees and gently and seductively worked his way to having my cock in his mouth. He gave great head. I did not get a blowjob much at home anymore and this felt great. Still the thought of his cock was greater than the desire to cum soon.
I said I wanted to touch his cock, so he stood and we moved to the bed. He laid down on his back and invited me in. I pulled his boxers off quickly, like a kid at Christmas. I was nervous, but reached and took it in my hand and started slightly pumping. To that point, that was all I knew about cock. It was exciting touching another man's cock and soon I moved to have it in my mouth. It did not take me long to feel at home and bobbing on his cock, trying to give the pleasure of great head. I must have been doing okay as he was making all the right noises and trying to fuck my face. I don't know how long I was blowing him or if he was getting close to cumming, but I knew I was ready for more attention too.
I paused to asked something like 'what next', when he asked if I wanted to be fucked. I knew I did but replied with 'I will try it'. He got up and pulled some condoms and lube from his suitcase, came back and laid them on the bed. I was laying on my back so he gave me head again for a minute or two to just completely work me up again. I was so hot. Then he instructed me roll over and lift my ass up. He took the bottle of lube and squirted some in my crack and soon had a finger working my hole. I was tight and he told me to relax. It was feeling better and I was relaxing. Soon he worked another in then another as he was stretching my hole with short finger fucks. It was feeling good and he asked if I was ready. I said I was and he told me to open the condom. I tore it open as he came around and told me to put it on him. It had been years since I had unrolled a condom, but unrolling it on another man's cock made me shake, but I got the job done. It reminded me of seeing my cock for the first time wrapped in a condom and about to get laid for the first time. In a lot of ways it was the same.
He moved behind me, added some more lube and put his fingers back in me for a minute to make sure I was still loose. Then, out came the fingers and replaced by the head of his cock. Slowly he pushed until his head made it inside. He paused only briefly before he slowly pushed inside me deeper. It was a little painful as I got used to his dick inside me. He continued little by little, pausing with short fuck strokes when I would tense up. When he felt me relax he would push deeper. He repeated this process until I finally felt his hip on my cheeks. He paused there only briefly before he pulled back to almost pulling out and then slid it all the way back in. Another move like that and I remember saying "OH YEAH". Then he let loose on a wild fuck of my ass and I was feeling great. My cock was hard as hell as it slapped against my own stomach as we moved with each thrust. I could feel his balls slapping my ass and he pump his cock in and out of me.
We started getting a little vocal as he told me I had a nice tight ass and if I liked it. I said, "Oh yeah, fuck me", and we were both making or own fuck noises. He said he was about to cum and asked if I want him to cum on me. I said I wanted to watch him and he told me to roll over when he pulled out. He fucked me a little longer and I could tell he was getting close. Soon he pulled out of me and pulled at his condom as I rolled over. He moved over and started stroking himself over the edge when he started pumping his cum all over my chest and stomach. I was stroking myself watching this and was about to cum myself. As he finished he said let me and he moved and took me in his mouth. I would not last long. I reached over and took his just spent cock in my hand and gave it just a couple of strokes as I announced I was gonna cum. He did not move away but instead just sucked harder. That was it as I started exploding right there into his mouth. He slowed down as my climax was subsiding and he swallowed every drop of my cum. His mouth stayed on my cock until I started to soften. Never before had any girl allowed me to cum in their mouth. That made the blowjob perfect.
I still had my hand on his now deflated cock when he lifted he head, looked at me, smiled, and said, "I think you are Bi now".
I laughed and said, "Yes, and I think I like it."
I did not spend the night there, but every day until we left on Thursday, we managed to get together for me to learn more. By the end of the week, I blew better, swallowed cum, and fucked him a time of two, but I still preferred to receive since it was all so new to me.
I have not repeated any guy experiences yet, but I hope to hook up with Nathan again somehow and possibly find new partners.