How do I introduce my boyfriend to anal play? Any specific tips on touching and/or licking a newbie you guys can give me?

Start by letting him know that it's something YOU want. Whenever my partner is the one pushing it, it makes it even hotter.

If you've done this, which it sounds like you have(?), let him know that despite what homophobic assclowns the world over have said, enjoying assplay doesn't make you a "fucking faggot" (gotten that once). And those people that use such language are utter cunts and a disgrace to society, so why would you listen to them anyway?

The prostate is just another level of sexual exploration that feels fucking amazing, so why the hell wouldn't you want to explore it?

Give it enough time, and you'll be here before you know it!

And you know, because you're even asking this question to a sex blog, you're probably cool as fuck. So perhaps he is too. And the above isn't even relevant. Let's hope that to be the case. The social stigma around men and assplay is fucking idiotic.

Ok, on to the important stuff:
Start slow.
Take a bath together.
Or a shower if you're not into the slow shit.
Make him comfortable, scrub that ass so it's nice and clean.
And then hop right into bed.
Now blow him.
Play with his balls.
Put some pressure on his taint.
Be messy.

Then go for it.

Adding a finger, or drifting down to his asshole with your tongue while you're giving him head is always a great way to get him revved. While you do something he's crazy about (I would assume he's crazy for a BJ), slip a (well lubed!!!) finger in. And yes, make sure it's lubed. Nothing is gonna turn him off faster than a pained wiggling finger entering his asshole.

If you decide to toss his ass first (how could you NOT love that???), give him some extra saliva and get in there. Once inside, go slow. Make it a goal to just get midway.

Remember, there are two points of entry to get past, the outer rim is only one of them (and the easier one). The next level is all about relaxation (hence the blowing). He'll pull you down that route when he's ready.

From there, if he likes what he's getting, add more and more. Eventually, he'll be begging for you to fuck his tight little asshole.

Good luck! And remember, lube that shit!

Oh, and don't forget his cock!


  1. Thanks for the suggestions! Your assumption is right, he's not homophobic in the least and indeed is pretty "cool as fuck". He knows very well that my greatest sexual desire is to peg him and has agreed to let me...eventually. To get to eventually, I figured I needed a place to start (such as fingering and/or licking). At the moment, we've had anal sex numerous times and I go crazy when he licks my ass, I'm just unsure of how to do things to him and make them feel as amazing as they do for me. Thanks again :)

  2. So great to know, Willow!

    And yea, no thought in my mind that he himself was homophobic. But that the social pressures from other men growing up make it so that we sometimes limit ourselves in that area. Which is fucking idiotic. Cause it's SO fun.

    Glad to hear he's agreed to be pegged, he's gonna love it. So now, it's just a matter of working your way there. Enjoy each step along the way. And remember, if it drives you fucking crazy, it's probably going to do the same for him. Plus, he's got a prostate in there, which beats you by a step!

    Have fun!