How long should I wait before I ask my FWB for anal?

Me and this guy decided to try being friends with benefits. We've both done it before. We had our first time together and I for some reason I really wanted him to give me anal. I really enjoy anal and its part of all my relationships but I usually wait a while to make it special. This time I don't want to wait but I also don't want to look like a slut (we just met a few weeks ago) and don't want him to get bored with me. If a woman already enjoys anal, what's the typical time before doing it with a new guy?
Updates:
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PS, I already know he likes anal but he doesn't know I like it.
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Most Helpful Guys

  • I think it would be really hot if you asked for it at an inappropriately early stage. Since you've already met him, he can't still be a stranger, but you can go it right now. Just tell him what you want and know there's no reason to be shy! If he obliges you will on cloud nine, and if he doesn't, well he sucks!

    • Really? that's so opposite what I assumed. but doesn't that set us up for disappointment? if we have anal the first week, there won't be much new things left in a couple months

    • Oh ok. But don't you want it up the poopchute sooner rather than later?

  • You like it, you want it, you know he's good for it.

    I'm wondering what you're waiting for, and I think you are, too.

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What Girls & Guys Said

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  • Have to agree, confidence in a woman and her ability to express her needs is a definite turn-on to most guys. Just put it out there to him, especially in the heat of passion, I personally find it pretty hard to refuse most any request made at that point!

  • If the guy is as great as you say he is, he shouldn't think you are a slut. There is no set time limit. A guy doesn't look at his watch and say "Well, it's been three weeks. Time for the anal!" Ask him what he thinks about anal first. If he's weirded out (some guys are) then perhaps you can avoid the rejection. Don't go along with him if he dislikes the idea though. We agree to disagree sometimes, that is human nature. Good luck.

    • Thanks. He's a good guy or I wouldn't sleep with him so it's not that I'm afraid he'll "dump" me. But I want us to have great sex. It's actually more about making sure its good for him.

    • If you know he likes it then I'm sure it's going to be good for him.

    • Am I being too girly and over analyzing this?

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  • Ask away what's it's going hurt, not a damn thing especially if you like it!

  • I'm more interested in sex. Can I help me to gain knowledge. So that I can make my girl happy

  • Did you let him in yet?