When I was 20 my summer break from school started at the same time my roommate David had to go away on business for two weeks and decided to take me with him; David was 45, 6'2", muscular, furry chested, stubbly beard, short black hair and green eyes. We had been jerk off buddies for almost a year and bringing me a long was partially because he enjoyed my company and partially for stress relief, at the end of a long day.
The hotel room David had gotten us was really nice, it was a suite with a queen size bed, surprisingly large shower for a hotel room and a hot tub right in the room; despite David and I'm not having a romantic relationship, he often did things like this that from the outside seemed like dating.
The first thing we did was unpack, which is something I have never done before in a hotel but we were going to be there for two weeks so David was pretty insistent that we move in properly. The second thing we did was take a shower together, David had my back pressed against his chest as he jerked me off, he knew I loved seeing him wet and naked so he was teasing me by keeping me face away from him but at least he was kissing my neck. After I came I turned around and started jerking him off as he washed me, it was a game where I would try and see if I could make him lose focus of what he was doing.
We had been there for a week when David introduced me to Travis, he was the person David was directly working with. Travis was about 6 foot 1, 35, blonde hair, blue eyes, slim but with extreme muscle definition, very defined pecs and a six pack that was bordering on an eight pack. We had been hanging out with Travis for a few days, David told him we were roommates but I'm pretty sure he thought we were dating given the fact that we were sharing a suite with only one bed. I think it was a day or two before we were going to leave and the three of us had just had dinner, we invited Travis into the hot tub with us. Travis didn't have a swimsuit, not that we did either, so three of us went in naked. Seeing both David and Travis, naked in the hot tub was crazy hot. I'm pretty sure Travis thought the same because he got up the nerve to ask what was going on between David and I. We ended up telling him that we were jerk off buddies, the end result was the three of us sitting on the edge of the hot tub jerking each other off.
Travis ended up spending the night, all three of us in one bed, the three of us jerking each other off again that night and Travis gave me a blow job. The following day the three of us jerked off together again, ordered room service and then Travis and I took a shower together while David ran out to pick up some dry cleaning. Travis and I alone together in the shower was crazy hot, we were full on making out while jerking each other off. We both came within seconds of each other but Travis kept going. He started kissing my neck, chest and sucking on my nipples while continuously jerking me off, the second time I came was about five minutes after the first time and I never even went soft in between.
I was hoping the three of us would have a chance to do something together again before David and I had to leave but unfortunately we didn't, I did keep in touch with Travis though and we had several jerk off sessions over the phone over the next few years.
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