The Gentle Introduction of Ass-Play.

My boyfriend is very willing to explore sexually with me, and loves me for the fact that I am so liberated and willing to try new things. However, there is one thing he is very shy about: his ass. Ever since he went down on mine, and took my anal virginity, I have been dying to give him that same pleasure. However, he is one of those men that, to a certain extent, equates anal penetration with homosexuality in men. I have told him I want to go down on his ass, and he is willing to let me, although I haven't done so yet. He knows I would like to try pegging, but I think he is a little afraid of it. Any ideas on how to gently ease him into ass play? 

I finally coerced my bf into giving me his ass for my bday. What should I respectfully do to keep that small potential window open?

YES. YES. YES.

That being said, if it's a first time, be gentle and don't go full steam ahead on him. I'd suggest starting with a blow job and the slip of a well lubed finger. If he likes it, add a second.

Don't let him cum though, you need to move on to tonguing his ass. The first time Violet did it, I could fully tell that she had pleased as many women with that tongue as she has. Holy FUCK. Get in there and show him a good time. But don't abandon the cock. Use a hand to stroke away.

Then move back to the fingers, or perhaps a plug and get on top of him while he rides out the sensations. As you're fucking him, ask him how good it feels, and how good it would feel if you had him bent over the bed, stroking his cock while you fucked him.

As he comes, REALLY, REALLY HARD (like, animalistic HARD here, not even kidding) let him know how badly you want to do it all again, and to elevate it next time.

Assuming it all went well, he won't be saving that ass for special occasions anymore.

Oh, and have fun! It might be butt stuff, but it's still just sex. Get on it!

New to anal. What kind of lube do you recommend?

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Violet, or Rye, or both - any suggestions regarding amateur anal for a couple? Tried it for the first time tonight (albeit in the shower), but my girlfriend ended up pretty sore. Any advice would help (lube, position, pace etc.). Cheers!

OH MY. Oh. Shower? OH NO.

Okay. It was a good idea. Steamy, warm, relaxing. All great things. Unfortunately for you and your girlfriend's b-hole, the butt does not self-lubricate. Which means that you need lots of lube for things to go well. And in a shower, any natural moisture or oils or anything that may have helped will be washed away. Which is why she's probably feeling a little tender at the moment. This is an unbelievably common mistake, so you definitely shouldn't feel too badly, but you should probably buy her a bottle of champagne and give her a massage, just to be on the safe side.

My wife is warming to the idea of trying anal. Any suggestions for positions that work well for first timers? And of course pictures are always helpful...

What great news! This is a crucial time, because upon your first experience, you could either take all the right steps and make her love it as much as Violet and I both do, or fuck it up horribly and never get access again!

So, given that potential for greatness or ultimate failure, why don't you recap with a post about our first try at anal:

http://uncommonappetites.blogspot.com/2010/07/about-anal.html

As for photos, I take it you mean of us. However, we've never really taken any of us in the act. I can, however, offer you this for inspiration:

http://uncommonappetites.blogspot.com/2011/03/your-ass-and-why-you-should-open-it-up.html

And, you know, this photo of a fine, ripe Violet asshole:

Ask us anything. Make it filthy.