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Here are some ways I can suggest:
Come up with natural, unforced occasions when you can get naked in his presence or at least allow him to see you nude. Changing for bed or getting into the shower.
Let him catch you naked a few times innocently. If you are now walking through the house/apartment nude, then it might seem strange to just start doing so. So you first have to get him used to seeing you in various states of undress. Start my coming out with no shirt or lounging around only in your boxes or athletic shorts.
Later try to set up more 'naked' situations where he catches you naturally.
This might be his knocking on your bedroom door (to get something you borrowed or that you share - cordless phone, vacuum cleaner, etc). (if you have separate bedrooms) and you're nude doing something like trying to untie some knotted shoelaces (and you may have the stereo/TV on) or headphones on (so you can't him knock).
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1) Start freeballing - that way you'll already be half naked. Your roommate will get used to seeing your cock, balls and butt if you undress where he can see.
2) If he's too uptight, he'll keep looking away or even ask you to dress in your own room. They will give you clues about how to proceed.
3) If this avoidance behavior persists, especially if he mentions it or draws some attention to it (like leaving the room), you could confront him about his being too uptight or too restrictive on your own personal freedom.
4) If he jokes about it, then you could also joke back with him.. 'Try it out, you might like it'. Just be upfront (and clever).. " seeing me naked doesn't bother you, does it?" How would he answer that but say 'No, not at all."
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6) Always sleep in the nude so it won't be strange for you to be naked in and around your bedroom, also when you and he get to do some overnight trips or camping, etc.
7) Get a friend who is a nudist and whom you visit with your roommate. The friend can invite you and your friend to get naked (whether he's gay or straight or with a woman) the 'pressure' of your friend's request might help him to break down the barriers so he'll actually get nude too. At least, you can accept your nudist friend's invitation - so you'll be naked in front of your roomie.
You could do something so innocent as:
A) meet in the in-house bar/restaurant for drinks or snack,
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3) Hold a party in the room and play strip poker (or an easier kind of game where the loser has to remove a piece clothing until some (or all are naked).
4) More clever would be for several of your group staying in the same or nearby rooms and then pretending not to know each other.. .. so we can get some going like one guy jerking off in his bunk, and then another guy (our member joining in). It would get some of the other guys (not our group) horny and they would join in the fun... Maybe a little farfetched... but you never know until you try. Outside the hostel... it's very large and could be very crowded
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6) You might try going to a bar/club where nudity is either allowed or required
7) Perhaps some one would be willing to host a small group in his apartment, office lounge after hours..etc, for some naked fun.
8) Another idea is to have pre-selected roles for a type of simulation - visit to a doctor's for an exam. One guys in the patient, another two play the role of physician and or specialist, there could be a male nurse who gives sponge baths. It's up to your imagination.
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Am I losing you here? There are other roles that come to mind.. but it takes a bit of energy, a passion for realism but with a big dose of fantasy, and a suitable place where that could happen.
I hope you're able to get off with a guy if one of these tactics works.