Christmas Fling

For various reasons, I decided to stay in town for Christmas this year. I've always gone home to visit my family or spent it with a girlfriend. This was going to be my first Christmas actually alone. I wasn't too worried since I have a good group of friends, but this year, it seemed fashionable for everyone to take long vacations over the holiday so as it got close to Christmas things seemed pretty lonely.

I noticed that the online M4M dating was a buzz for the holiday since everyone seemed to be looking for a warm body to cozy up with. I joined the fray and posted an ad. I got a bunch of responses, but none of them were appealing except one from a guy who while cute an thoughtful was just twenty-four years old (and eight year gap). I showed his profile to a friend and he asked when I was going out with him. I told him I was about to hit the delete key and my friend convinced me that I should at least go on a date with the kid. I couldn't come up with any valid reasons not to other than that it just seemed like too big of a gap for me so I responded.

We emailed a little while and ended up going out the next night. We me at a Starbucks after he got off work. Online dating is kind of a crap shoot and his pictures weren' super clear, but he seemed cute in them. He was pleasantly cuter in person. He was pretty shy and was a bit taller than average with short dark hair and pretty blue eyes. I'm normally the shy one but this guy was worse. This made me relax and focus on being friendly to draw him out. He seemed intimidated and nervous, but I felt like he liked me. We were there about fifteen minutes when the starbucks people came and said that they were closing.

One we were on the street, it was freezing and nothing else was open on that road so I got bold and asked if he wanted to come home with me to watch a movie. He had walked so we got in my car and made the twenty-minute drive to a video store by my house, rented a movie, and then went back to my place. I made a little snack and then we went to my TV room to watch the movie. I was getting a little nervous. I haven't done this thing a whole lot and it's kind of exciting not knowing what is going on. I've been on dates with guys where we did just sit and watch a movie. My 24yo date also had moved to Seattle recently from a small town and commented that he doesn't date much and is turned of by the sleazy gay scene so I wasn't expecting anything more than maybe a makeout session.

I had had a friend staying with me recently and the sofa bed in my TV room was still in bed state. We laid on the mattress and started watching the movie. I decided to be bold and cuddled up next to him. He didn't resist, but he didn't reall respond much. Then I brushed my arm against his. We continued like this for about ten minutes before I slightly rolled towards him and he wrapped his arms around me as we kissed.

Things got crazy as we rolled around making out. Hands went everywhere and I reached around to feel his shockingly tight 24yo ass. He moaned, "you're so hot," which would have seemed cliche coming from someone my age but was cute coming from him. Shirts were the first to go and I admired his slightly hairy body. I was prety amazed because he doesn't really work out, but he had a pretty decent body. The up side to being twenty-four...

Pants came off and we dry humped a little before heading to my bed. I picked him up and carried him cave man style (the advantages of being a gym rat) to my room. I tossed him on the bed and stripped his underwear off and attacked him. I got on top of him and kissed him and slid down to his largish cock. It was the second biggest I have encountered and I gagged a little trying to be all slick and do the deep throat thing.

He was super verbal and kept randomly moaning "fuck, fuck, fuck." After dating a really silent, awkward guy for a while, this was a pleasant change. I played with his ass and he got excited so I reached for some lubricant and worked a finger into him. His ass relaxed pretty easily to let my finger slide in and I worked the inside of his butt while continuing to suck him. I did a sniff test and decided against rimming him even though I wanted to :)

He was really getting into my fingering him and I decided I wanted to lay on him and grind my cock against his ass for a while and then try fucking him. I rolled him onto his belly and slid on top of him with my arms holding his down. I slid my cock between his cheeks a couple of times and then the head caught onto the rim of his hole. I had fucked one other guy before and it was way harder to enter him than this so I was surprised when the head of my cock slid into his ass. I was totally in lust and was kind of sex crazed. He started moaning and to my shock he opened his ass and lifted it up at me and then I matched him by sliding my condom less cock all the way in to the hilt. I knew I was doing something really bad. If I had been in his shoes, I would totally have pulled the plug and put a condom on the guy. As a circumsized top who knows that I'm HIV- negative, I just started thrusting. Eventually, I rolled him on his back and put his ankles around my ears as I reentered him. He started stroking himself and shot all over himself. I picked up the pace and absolutely exploded inside of him. I could feel my come hit the wall of his ass and then slam back into me. It was crazy. He moaned as I came. It was the hottest sex I have ever had, but I felt super guilty. I know that my more aggressive personality and physically imposing build probaly intimidated him.

We talked about it after and I asked him about condom usage and his sexual history. He's had very little sexual experience and not much anal sex. He's always been safe and we were both in a little bit of shock about what happened.

I spent my Chrismas Eve, Christmas, New Year's Eve and a lot of the holiday season hanging out with him. He's a good guy. We dated for about a month. He had a pretty bad breakup before me and was already battling depression so we stopped dating but are working on a friendship. I think that the age difference was a big problem since we definitely were at different levels and things got worse as time went by. Still, I don't regret it. I had a nice holiday season with a really nice guy. I'm convinced that I'm going to basically stick with a +- five year age window from my age going forward though.