This happened at a business conference about six months ago, and I am still thinking about it!
I came upon this site fairly recently, and enjoyed hearing about some of the experiences, so thought I would write up something that happened about six months ago while on a business trip. Not sure it will happen again, but been thinking about it since!
(I just re-read it, and it is really long, but wanted to share the details of it)
My company had its national conference last March, and it's usually at a really nice hotel in a different city each time, so was looking forward to it. Last minute, they told us we would probably have to share a room, due to hotel size (same gender in a room, of course), but didn't bother me a lot.
When I got there, I first thought the other guy was a no-show, but then saw his bag on a chair. The bathroom door was open, and I could hear the shower from inside. I started unpacking and after a few minutes, the other guy (will call him Ray), came out in a towel and introduced himself. He is a good looking guy, tall (about my height which is just over 6, and similar build) and clearly works out. He was friendly enough, and seemed comfortable enough that he just turned his back to drop his towel and pull on a pair of jockey shorts.
Ray said he was going to the hotel gym, and would I like to join him, which I did, so I quickly changed and headed down for a workout, which I always enjoy. Ray and me got on pretty good, always with a conversation going and swapping workout tips and some jokes. At one point, I was doing my chest presses, and he came over to spot me, and I have to say that I noticed this dude was probably pretty hung, by the bulge that I was looking up to from the bench (not that I usually focus on these things, but it was pretty noticeable!)
Anyway, rest of night was as planned, went to the conference dinner and drinks after, and saw Ray now and then through it, but was a big conference and lots of people I knew. Some folks were going to the city center for some more night life, but I thought I would pace myself, since its rough to start a conference with too much booze ( I have learned that lesson before)
So headed back to room and Ray was already there, flipping channels on the tv. I was surprised that the guy was relaxing on his bed with only his jockey shorts on, no shirt or anything else, but figured that is not so unusual for a guy, since I do that at home a lot, but did seem like this guy was making himself comfortable. Ray had brought a few six packs of beer with him, and he offered to me, which of course I accepted.
We chatted a bit about the evening, then I said I wanted to take another shower, which I usually do before bed. He kept chatting with me as I went into the bathroom, so like him before, I left the door part open and we continued chatting, even when I got in the shower. It was kind of fun, reminded me of being at the gym when you keep the conversation going in the showers, which I like, and I was glad my roommate turned out to be someone I got on with. Ray even came in to the bathroom to take a leak while I was showering (I heard him clearly, but didn't see him doing it) and he kept chatting with me all the while, which I thought was kind of cool for guys to do.
(I know I am going into a lot of detail, but it was a fun night and I enjoyed the parts of it)
So, I came out of the shower, with a towel around my waist, and when I came back into the hotel room, Ray said he wanted to show me some pics of a previous girlfriend. I sat on the edge of my bed, still in just my towel, and he came over and was showing me some pics of this really HOT girl. I could see why he wanted to show her off! She had really big tits, long hair, the whole deal. So he starts showing me these, and the pics got more provocative and more sexual (nudie shots and all that) and I started getting a major woody under my towel! I felt really embarrassed, but was also really turned on by the pics, so I kind of put my hand on the towel to keep my cock down and under wraps.
What made it worse was Ray keeps showing different pics, and talking about the girlfriend and the sex they had in more and more detail, and he sits right on the edge of the bed next to me to hold the phone where we both can see some different pics of her, more and more explicit. The guy is still wearing just his jockeys and I swear he was popping a woody as well, but I didn't want to look!
He pulls up this one pic, in which the girl is bent over and putting two fingers in her pussy, and I think I almost fainted looking at it! And then, the worse thing, Ray just said to me that my boner had come out from under my towel! I looked down and the head of hard dick was facing right up at me, in open air, where he could see it! I almost died, but he just kind of chuckled and said he had shown these pics to a bunch of his friends and they all had the same reaction! So maybe I felt a little better, but not much, so I pulled the towel back over my dick and tried to act all easy about it (which was not easy, I can tell you)
Ray doesn't drop the subject and was saying that guys shouldn't be self conscious about their dicks, and especially around other guys since we all have one. And then he asks if I want another beer and gets up to get them. and the guy is sporting a major pup tent in his jockeys and doesn't seem to care! Really, he walked back over to me with the beers and his hard cock was pointing straight forward like nobody's business. It was really hard not to look at it, including there was a big wet spot where the head of his cock was, probably from pre-cum coming out.
So Ray sits down again and we are having more beers and talking about the pics, and he started saying that he loves the pics because he jerks off to them all the time, and its a good way to remember the girl and how much he loved fucking her. And he starts using really sexual talk about how he fucked her, and as he is saying this, he started running his hand up and down his shaft that was in his jockeys. I have to say, I got pretty turned on, all this talk about fucking and the pics and then a guy rubbing himself while sitting next to me, it was a major turn on! And without thinking too much about it, I kind of leaned back against the headboard of the bed reached under my towel and started rubbing my hard cock as well. My heart was pumping something crazy but I couldn't resist it.
Seems like Ray liked the idea of what I was doing, because sure enough next minute his hand was in his jockeys, and then he pulled down the band and his really big cock head popped out. It was a really nice one (mine is good too but it's different when you see it on another guy) and his was all wet with pre-cum. Our chatting turned to masturbation and how much we enjoyed it and soon we both had our cocks fully out and showing off our pumping with each other. It was pretty exciting and I surely forgot how embarrassed I was earlier in the night. My heart was really pounding something crazy now but I was all horny now and I didn't care, I was getting so turned on.
Then Ray said something like how he thought I had a nice looking cock, and he spat on his hand and reached over and starting pumping mine for me. First time I ever had that, and I thought I was going to cum in about two seconds! But he slowed it down and also went south with his hand to my balls and it felt really incredible, like the best jerk off I ever had. I started moaning and saying shit that I don't even remember, but it was crazy sexual and I guess they say, nobody knows better how to jerk cock then another guy!
Of course, I couldn't resist returning the favor and had my first experience of stroking another guys meat, which was kind of awesome, especially how the dude started moaning too and I could see that he was getting really turned on and started mumbling all sorts of dirty talk while I was jerking him. It was really horny and I get a serious bone everytime I think about it now!
One part, I laid down on my back while he was jacking me, and he got on his knees over me and started stroking me really hard, and I came about five ropes, mostly on my chest but one hit my face, which was pretty hot. Ray started jacking himself while still on his knees over me and I was feeling his balls and crack while he was doing it, and I got really excited and put my finger a little bit in his butt hole, and the guy blew a bunch of ropes right onto me! It was really horny and he laughed and kind of mixed both of our cums together on my chest and said that he guessed we were now proper roommates since we had mixed our jizz together!
I was really exhausted after, I didn't even want to take a shower, so just towelled off the cum and pretty much went to sleep, each in our own beds. Next morning, when I woke up, I couldn't believe we had done this, and started to feel embarrassed, but then Ray came out of the bathroom naked with a semi hard one and made a joke and we both laughed and just relaxed around each other.
Needless to say, the conference was for three nights, and you can guess what I was doing for the next two nights! Without discussing in advance, Ray and me would have dinner and drinks with the business guys, then head back to our room early for some buddy time! It was awesome, and I think I shot my wad more in three days than I had for months.
Part of the best of it, being so comfortable, him and me, we would strip down as soon as we got into the hotel room, and walk around with hard ons most of the time. I was so turned on you would think they were putting viagra in the water!
Other thing is, I think the room must of smelled like cum really bad, I wonder what the cleaning lady thought when she finally had to clean the room!
Update to now, Ray lives halfway across the country, and we email and talked on the phone since then. As you can imagine, our chats can get pretty horny (neither of us have forgotten those three nights at the hotel) and I often think about that first time at the hotel and want to see when we can meet up and might continue the activity.