I used to have a group of friends that did pretty much everything together. There was probably around 15 of us in the group and usually 6 to 10 of us would take vacations together 3 or 4 times a year. Or favorite destinations were Sagautuck, MI or New Orleans.
One of the guys, named Jeremy, was a wild child. I always said I would share a bed with Jeremy, only because Jeremy was out most nights and would only come back to the room to shower and spend a few hours with us during the day. So I usually had the bed to myself. I'm a heave sleeper, so the few times we slept together I don't remember much. But one time Jeremy and I sat together on the train to New Orleans (which is an overnight trip). During the night, he moved the armrest up so it wasn't between us and he cuddled up against me under the blanket. I put my arm around him and held him. It was very nice. At one point, I woke up and his head was laying in my lap and my hand was very close to his crotch. I moved my arm to get more comfortable and my hand was on his crotch. I could feel his dick was hard. I gave it a few squeezes and I saw he got a smile on his face. Not sure if he was asleep or awake, but I just left my hand on his dick.
The best time was when I had made the hotel reservations for a trip to New Orleans. I had made hotel reservations for 8 of us (2 rooms). We had to delay the trip by a day, because one of the guys had to work so I changed the reservations to arrive a day later. The guy we were waiting on suddenly couldn't go, so the seven of us decided to go down there a day early. We get to the French Quarter and started day drinking. It was about 9pm by the time we arrived at the hotel and tried to get our rooms (we were a day early). The hotel only had 1 room available. We were drunk and tired, so we decided to take the room. So all 7 of us piled into the room. 5 of us decided to share the bed. With lots of spooning we decided we could make it work. Guy #6 slept in the chair and #7 (the straight guy in the group) slept on the floor. We were drunk, feeling good and lots of grabbing and groping happened in the bed that night. (Not much sleep.) Two of the guys did go to the bathroom together and were in there for a good 10 minutes with the door locked. They made it obvious when they left the bathroom and the toilet never flushed. Great times.