I've been in pretty similar situations with a couple of guys. One worked out well and we had great sex for months - still do from time to time but the other was not so great.
This guy was a new friend - we worked together and travelled on business lots sharing a room - and indeed a bed as most of the hotels never separate their twins. I quickly came out to him as bi - he let me know that he had snogged a guy once but was not really interested in going any further. I decided to take the bull by the horns and let him know that i had a serious crush on him and needed to let him know - he said he wasn't into guys again. a few days later we were at a work thing and both very drunk that night in our room. I asked him if he wanted to cuddle and he agreed - he said nothing was going to happen so i turned my back and let him spoon me. I couldn't sleep all night with his arm around me - turned me on so much. He also had a semi-hardon for most of the night... This flirty thing went on for months - various pretend fights, almost kissing moments, cuddling, and like you blewboi101 i would brush against him in the middle of the night - and not sleep just in case he reciprocated. Alas, he never did.
The closest i got was one night he was really seriously drunk and i was actually asleep - he got up and this woke me up - he was standing at the side of the bed - not sure what he was doing - asked him to come back to bed and he came and cuddled me - the next thing i knew he had my hand and it was pressed against his cock which was getting hard. I pulled my hand away (he is my friend i wanted to be sure he was up for it and not just really drunk and horny) he grabbed it again and put it down his pants. I started to wank him off and just as he was getting solid in my hand he changed his mind and pushed me off - i tried to cuddle some more but he really pushed me away. I took this as a real signal not to push it any further and that was an end to it. I decided we needed to clear things up - told him how much i wanted him and how his flirting was really eating me up - we agreed to be friends but i knew from his response that we were never going to go any further no matter how much i wanted it...
Anyway my advice is tell this guy you have a crush on him - maybe do it in a way that suggests that you "know" he's not interested - leave the ball firmly in his court - let him tell you one way or the other what he feels. Tell him you don't want to ruin your friendship but you really need to know... It's best for both of you! If he's not interested you'll need to move on - it's hard - i'm still in love with my friend 2 years later and speak to him daily at work but i know nothing will happen.
Hope that helps.
By the way, RRRalph your advice is always sound! Keep it up!
IMO i like this idea.


































