Scratching an Old Itch

I was in my mid-40's and my marriage had been going south for some time. I travelled a great deal for business which I found to be a welcome respite from my home life. I surfed the web from my various hotel rooms and soon became addicted to adult chat sites. It did take me long to find my way into a gay chat room. I had some experience with gay sex in my late teens and early twenties but had not indulged my bi side for over 20 years.

I started with erotic chat with various guys and graduated to phone sex. It only left me yearning for something more. One of the sites I frequented let you post personal ads so I posted an ad looking for a hook-up during an upcoming trip to the DC area. I did not get too specific about what I wanted to do.

Gary answered my ad. Like me, he had experimented in college and longed to try man sex again. He was about 15 years younger than me but said he liked older men. He described himself as a little shorter than average and slender. We exchanged e-mails and arranged to meet in the bar of my hotel.

I nervously twirled the ice in my whisky glass as I waited for him to appear. I had given him a pretty good description of myself right down to describing the shirt I would be wearing. At precisely the agreed time, he appeared in front of me and said "Tom?" I looked up at a very handsome 30 something who stood about 5'-7", a very slender body and brown hair and eyes.

He ordered a drink and we chatted, nervously at first but we gradually became more comfortable with each other. "Well," I said, "shall we do it?" He concurred and I gave him my room number and asked him to wait 5 minutes and come up.

Once inside my room, I stripped down to my bikini briefs and anxiously awaited the knock on the door. Those 5 minutes passed very slowly and I began to fear he had left. Then I heard the knock. I stood behind the door as I opened it for him so I could not be seen from the hall. When he saw me standing there nearly naked with a very prominent bulge in my briefs, he gave me a huge smile and hugged me. He also kissed me on the lips, something I wasn't quite expecting. However, I found I enjoyed it.

Gary didn't waste much time after that first kiss. He stripped in a heartbeat and knelt in front of me and pulled my briefs down freeing my 7" throbbing erection. He took my cock in his mouth and proceeded to suck and lick it. I let this continue for only a few minutes before I said we should get in the bed.

We kissed some more, even working our tongues in each other's mouths, something I wouldn't have imagined just 15 minutes before. We rubbed our cocks against each other which was an incredibly erotic experience. His was very long, at least 9" but also very thin. I tasted his cock and fondled his balls. Gary seemed to enjoy that very much and he would return the favor and suck me. We held back from sucking too long since neither of us wanted to cum too soon.

As we kissed and felt each other's bodies, I let my lips and tongue range all over from his neck to his balls. I discovered that I enjoyed sucking his nipples and having mine sucked as well. We rolled around the bed kissing and rubbing our bodies together. After we had been doing this for around 20 minutes, Gary ended up sitting on me with his ass rubbing against my cock. I have to say I enjoyed this.

When I had sex with men as a young man, I was usually the bottom - the one who gets fucked. Now, my man on man fantasies were about me doing the fucking. Gary and I had not discussed having anal sex in our several e-mails but with him sitting on my cock I decided to try my luck. "Do you want me to fuck you?" I asked.

"Hell, yeah!" he replied. I had taken the precaution of buying some lube and condoms that afternoon. I applied some to his man hole and began to explore it with one finger. As I did this, I used my other hand to gently stroke his cock. He was a bit tense at first but soon got used to it. Then I inserted another finger and repeated the process.

Once I felt his hole had been loosened enough, I put on a condom and spread a little more lube on his ass. Very slowly I pushed my big mushroom head into his tight boy pussy. When I had the whole head inside, I paused to let him adjust. He was obviously in a bit of pain but told me to keep going. Bit by bit, I pushed my cock in him, always pausing every so often so he could adapt to it. Finally, I was balls deep. I let it rest there and rubbed his back and butt. I leaned over and kissed his back and neck. "We will both love this." I said.

Slowly I began to move my cock in his tight hole. He was moaning in a combination of pain and pleasure. I could feel his grip relaxing after a few minutes and I picked up the pace. He began to really get into it. "Oh, yeah, fuck me hard, make me your slut." he moaned. I obliged him. I started ramming my cock in and out of his hole, even slapping his ass a few times which he seemed to enjoy. "I want you to cum all over me." he said.

We had been fucking doggie style, but now I pulled out and positioned him on is back with his legs on my shoulders. I began fucking harder while he stroked that long pencil thin cock of his. I felt about to burst and I pulled out, tore the condom off and started to stroke my cock. I erupted all over his cock and balls. I reached down to rub my cum over him when his orgasm hit. He shot several strings of cum with the first one flying over his head, over the bed and landing on the floor behind. Each successive shot was a little bit shorter until the last one landed on his chest.

I was caught up in the moment and surprised myself by leaning over and licking up our cum on his body and sucking the last few drops out of his cock. I never thought I would do something like this but passion overcame me and it felt right. We both lay back on the bed and told each other how great the experience was. We made out a little more and took a shower together. We finally parted but promised that we would stay in touch and, hopefully, hook up again.