How can I tell my boyfriend that I wanna try anal sex?

We've been in an off again on again relationship for about 5 years now and I wanna try something new and that's anal sex. I don't exactly know how he feels about it since we've never brought up the subject, he did however ask me what kinds of things do I like besides what we already do (some regular positions like missionary, doggy, doggy standing) but I couldn't exactly get up the nerve to mention it. I also like rough sex, I love it when a guy pulls my hair and chokes and spanks me (it drives me crazy). So how do you think I should ask him?
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Most Helpful Guys

  • WOW! he's a lucky guy. I think you should tell him during sex when your talking dirty to him and just say " I want you to put your hard thick C*&^& in my ass and come in it!". That's how I would want you to tell me!

  • Say What what wanna put it in my butt ... Or just ask

Most Helpful Girl

  • Give each other oil massage and bring it up after haha

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What Girls & Guys Said

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  • Tell him to ask you again and tell him. Find a nerve. If you love each other nothing bad can happen, does it?

  • Just tell him. If you're into it, he's gonna go for it. it shouldn't be awkward...

  • dont talk about it just put it in there

    • Are you a fan of anal?

    • I like the puss more. Cause when I'm Fing a ass I really only feel the ass hole the inside feels empty So a big fan? no

  • My girlfriend asked me to do it after a couple of glasses of wine. I of course obliged and we've done it loads since. I guess if I had said no, she could blame it on the wine!

    • I just might give that a try :)

  • just tell him

  • Just tell him. Tell him that you would like to try it with him and see what he says. The best way to know for sure is to talk to him.