SufficientlyConfused

Situational Sexuality, an enigma.

Expensive Gamble

As I have noted, I feel as though I would be able to initiate some kind of physical contact with my “crush” if I were able to get him in the same bed with me. If I am able to get him in the same bed with me, and I am able to initiate some kind of physical contact with him, I believe he will respond; hesitantly at first, but I honestly believe that at least on some level, my “crush” has the same kind of feelings for me, even if he a) hasn’t realized it yet, or b) doesn’t understand it yet.

As I have also noted, I have no way of justifying the two of us sleeping in the same bed because we are roommates…why would he come sleep in my room when his is across the hall? My plan.

My parents have told me that upon my graduation from college (a year from now) they plan on giving me a vacation as a gift, and I’ll be able to take one person. Even if I weren’t “crushing” on this man, I would still take him because he is my best friend. However, I can’t help but to see this as an opportunity. I brought up the idea of a two week long cruise to him, and he responded with absolute excitement. I figure I’ll probably use the first week to loosen things up…I’ll sleep naked, change in front of him, bring up sexual conversations, watch late night “porn” on the ship’s HBO…that sort of thing. My hope is that by the second week I’ll be able to pull of some staged “contact” with him. For example, a friendly and brotherly slap on his naked ass while he’s changing won’t be so awkward at this point. Hopefully, by the time the trip is over, I’ll have the intimacy I’ve been longing for with him or at least have the seed that I planted that has lain dormant for so long finally begin to grow.

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July 19, 2009 - Posted by | Uncategorized

2 Comments »

  1. Sounds like a great bro-trip. (Cool parents, too.) But… that’s a year from now. That’s a long time to be on the fence with him.

    You guys are roomies now (separate rooms). You’ve got a whole year to start relaxing the usual guy-guy barriers for nudity and contact. Sleep naked now. If you’d normally wear shorts around the house, just wear boxers. When you’d wear boxers now, leave those off too.

    How he reacts will probably say a lot about how comfortable he is around you. If he freaks out: Oops, sorry bro, my bad, I was sleepy and forgot my shorts.

    If he doesn’t freak out but he still needs an explanation: You just feel so casual around him you didn’t really think it mattered anymore.

    I’ve heard that getting drunk is another classic solution to this problem. 😉

    PS – Keep posting, it really does help. Even if it seems like whiny rambling at the time (mine sure has!).

    Comment by maybebi | August 24, 2009 | Reply

  2. Have any of this worked out for you?

    Comment by micclaria | September 16, 2009 | Reply


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