Anal with roommate???

Discussion in 'Sex With a Large Penis' started by Damn2great, Apr 25, 2011.

  1. Damn2great

    Damn2great New Member

    Dec 31, 2010
    Likes Received:
    This is the situation:

    Me and my roommate are really great friends, we talk about everything, though, we dont really specifically talk about our sexuality. I know that he is bi-curious(-ish).

    We oftenly go out together lookig for girls, whatever! Not every time we succeed, so than we're lonely :p Always after going out, I like to take a shower (it's really nice to take a shower when drunk). Suddenly he came in to the bathroom "to take a piss". After I got out of the shower, he told me he saw my cock (what a surprise...), he asked me if he could see it again, in favor he would please me....he didn't say how!

    After some talk, porn, and other things I cant remember anymore, we ended up him giving me a BJ and I jacked him off --> this was my first experience jacking another guy (have had other experiences though). His BJ was great, i even came on his face, and he licked it off, and licked his cum from my chest.

    I said that what he did, was a nice favor for me showing my cock, but he said that that wasn't all, he wanted to fuck!

    Now comes the problem: I wasnt sure of many things:
    - Did he want to be bottom, of would his pleasing be that he would fuck me?
    - I never did anal sex before

    So I lied myself in a strange way out... The next day we spoke a bit about it, not too open though: the only thing he said was that his offer is still open that's it!

    Last week he started being really nice, doing everything for me, when in a bar/restaurant/shop he offers to pay etc... I feel a bit awkward, maybe he wants more! I only see him as one of my best friends (with once a month a little benefit)--> how can I handle this best, without telling it straight forward?

    My second question is that i am mentally prepared for anal sex, i would like to try it! I'm not sure wether i will be top or bottom! so can you help me what i should do when:
    -I am bottom
    -I am top
    I've watched some vids about how to "clean" your ass befor anal sex, but i dont want to eat nothing all day, or buy a little ass-shower! how do i prepare for being bottom in about 10 mins (for example, in the shower..)

    Thanks guys, i am really looking forward on your reactions on how to handle this situation of him paying/doing everything for me and how to have anal sex!!

  2. Rikter8

    Gold Member

    Jun 30, 2005
    Likes Received:
    Depends on what your living situation is.

    Generally having sex with your roomate can turn sour in a hurry. So be prepared for that aspect if it happens.

    Preparing your ass in 10 minutes?
    Don't be suprised if you get some "presents" with a 10 minute prep.
    The shower shot kits are very helpful to speed the prep. An enema solution is also the way to go. But your going to have to clean out several times to be squeaky clean.
    I won't do anal unless i've had time to properly prep for the occasion.

    No matter what anal play you do, make sure condoms are involved.
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