With any kind of "experimentation" or trying new things sexually, the bottom line is that both people ABSOLUTELY need to be comfortable and okay with it. It doesn't matter how long the relationship has been or what, that is the only thing that matters is that both people are okay with it.
What's good is that you don't seem like a macho jerk that's going to jump down her throat. So take that honest and respectful attitude that you already have and tell her EXACTLY what you said above: "I wanna keep her happy, but this is outside my comfort zone."
If she gives you crap for it still, even after knowing that you aren't okay with it, then ask her how she would feel if the situation was switched and you were asking HER to do something in the bedroom that she really wasn't comfortable with. And remind her that you wouldn't push the issue once you found out that she wasn't okay with it and that's all you're asking for.
That being said, if she gets mad or is trying to pressure you into this, then you might have to seriously ask yourself if this is someone you want to be with. It's harsh, I know, but someone who doesn't respect your boundaries obviously cares more about their own needs than yours, and that's not fair. But I hope that's not the deal :).
Good luck hun!
Thanks for putting things into perspective. :)
First off, the strap on might be nice for you because anas stimulation feels good for the man. But if you don't feel comfortable with this, just tell her. If she seriously would break up with you over this, she has problems. Would you force her to something she wasn't comfortable with, probably not. I'm sure wouldn't dump you for something that petty. But honestly think it over, it could be fun. If you really don't like the idea, jst be honest, she'll understand. She is afterall asking to penetrate you like she's the dude & your the woman. That's gonna turn some people off, I'm sure she realizes this.
Go slow, lots of lube. Probably the best thing to do is give it a go on your own first. Will be less of a shock when she fucks you. But watch out for the multiple O’s
HAHAHAHA!
Oh my!
I laughed so much when I saw this!
Maybe let her do it, lube the damn thing up plenty first, though. And don't tell your mates, otherwise you will NEVER live it down!
Fucking hell... lol! xD
I think the only way, and I stress only way I'd let her have her way as if she's willing to do a 3some with me, her, and another chick.As another ChrisB said, she's probably bi curious.
Dude, that's a good compromise. You're doing the right thing.
A woman wanting to give anal sex to man is often more about control and power play then bisexuality.
Nothing wrong with it, little experimenting every now and the won't hurt, just use lube, you will be her little bitch... only do it if she will respect you afterwards...
Scroll Down to Read Other Opinions
What's Your Opinion? Sign Up Now!DON'T DO IT
Free spirited much?
comfortable and trust are key in a relationship.
If you don't want this she should not pressure you to do it.
If she does she is selfish.
haha.. I laughed out loud..tell her its out of your comforzone lol...she might be bi-curious... LOL
I suspected that the instant she told me about this idea.
just say the magic word" No" nicely
tell her since she want to use a new hole and she has new holes to offer you get to f*** another women then she can play with your booty.
how often does she do things she isn't so keen on?...man up and take it like man
Just tell her that is a turn off to you and you don't want to do it. I doubt she will throw a two year relationship away over that.
Sexual Relationships 
Sexual Health 
Most Helpful Girls