My BF wants assplay. On him. How do I anally pleasure a guy?

Exokisa / Woman / Likes Men / Single

It isn't uncommon. The butt is filled with nerves and can be a source of real pleasure for both males and females. Assplay works the same way for a guy and a girl. The only difference is that men have a prostate, while women don't. The prostate is like the male equivalent of a g-spot.

Since you seem a bit squeamish, I'd recommend starting off slow. Make sure your boyfriend has cleaned himself thoroughly beforehand. An enema shouldn't be necessary, but it can't hurt. Get yourself a nice pair of gloves. It'll make clean up later a lot easier and it will also protect his ass if you have long finger nails. Use plenty of lube.

You can just move your finger around his anus to start, experimenting with different speeds and rhythms. Try gently massaging it. If all is going well, try inserting a finger. Since he's used to fingering himself, he should be able to accommodate yours easily. Ask him what he likes/wants, as in how fast or slow. Stroke his butt cheek while you work, make it sensual for yourself. Just keep an open mind and feel free to ask him for directions if you're not exactly sure how to proceed.

If this is something you absolutely cannot do, let him know. Be honest with him. Don't force yourself to do it if you're only going to make both of you feel uncomfortable afterward.

Xtinacicchelli / Woman / Likes Men / Single

I've met many men who said they wouldn't want their butt played with. And I've met many more guys who couldn't get enough assplay after trying it once or twice. Your boyfriend is one of those lucky guys, and that he is able to share his desires with you is fantastic! That means he respects you and trusts you enough to play with him. There are several books and DVDs on the market right now that share advice and techniques for beginners and advanced anal-lovers alike. Tristan Taormino's "Expert Guide to Anal Sex" not only gives you down lowdown on anal play, but it also shows different couples having fun (This might be an arousing video to watch with your boyfriend too). If you haven't watched him play with his butt yet, then maybe next time he can show you in the bedroom. Make it apart of the sexual experience, then, when you're ready, take turns and play with his butt too! The anus experiences different sensations than a vagina, so the usual back-and-forth approach with the finger isn't as pleasurable (most times, it never is) as sliding your finger in and making a come-hither movement. Wear latex gloves and use just a dime-sized bit of lubricant to make this comfortable for the both of you. If direct contact is uncomfortable, then slowly work your way there and start with anal toys. Benwah balls and prostate stimulators can please him, just make sure you have control over the toys, so that way you're always participating. Have him help you if he experience any discomfort. Eventually, the smile on his face will hopefully have you begging to play with his butt!

jMarie / Woman / Likes Men / In a relationship

Wow, I think this is more common than I realized. I just posted a similar question about my guy. He wants to be locked in a chastity device (for weeks!!) and have me take him wih a strap-on. I thought those were only for lesbians but I guess I was wrong. I don't have any advice but at least we know there are others out there with the same desires.

Jojooome123 · Honestly, most men, including me, love assplay. The easiest way to satisfy a man anally is to actually finger his anus with two fingers, or even a metal dildo (because the dildos for women feel to wierd). Do this whiling sucking him off and he'll be going nuts. The first time I tried it, I came in like 8 minutes, and i'm a man who lasts about 39 minutes!

Rage / 26 / Man / Likes Women / Single

I can definitely say that I enjoy a little ass play. Rimming is a great way to do it... if you move into penetration, be easy about it at first. Perhaps a finger or something... And use lube! Lube is ever critical.

AmandaS / Woman / Likes Men / Single

You might have been grossed out by the initial idea, but the truth is that assplay is actually very clean and can be extremely pleasurable -- for the guy and for the girl. It helps if you and your BF have emptied your bowels prior to a given sex session. To stimulate his anus, you can use your finger(s) with your saliva; don't be afraid to penetrate his anus as deeply as your finger(s) can go; and don't be afraid to use all four fingers of your hand. This can give him extreme pleasure and probably will cause him to have one or multiple ejaculations of cum, especially if you are sucking the shaft of his cock at the same time that you are fingering his anus. You might be surprised to learn that your BF can give you the most intense pleasure you will ever experience in your life by either fingering your asshole or tongue-fucking your asshole or having anal sex with you. Your anus and rectum can actually accommodate many more inches of penis penetration than your vagina can, plus there is no risk of pregnancy with anal sex. Enjoy and have fun!

Alias / 22 / Man / Likes Women / In a relationship

An ass is extremely sensitive and a lot of guys like to have it stimulated. The way to do it is different for every guy so try something and just ask him how it feels. If he told you he wants anal sex, I don't thing talking about sex is an issue for you.
If you manage to stimulate his prostate, he might cum from anal stimulation alone. If not, a combination of anal and a BJ guarantees succes.
If you're grossed out by the idea, try some fiddling in the shower or demand him having a shower first. If that's not enough for you... try some nurse-roleplay. I bet he won't mind a latex glove then...