Convince Your Man To Let You Peg Him In 8 Simple Steps

Approaching anal sex for the first time — whether you’re the giver or the receiver, whether you’re straight or gay — is not something to wing or take lightly. Not only is it a psychologically loaded act, but it’s one of the few sexual acts that can be done “wrong.”

The anus is not self-lubricating (unlike vaginas and mouths) and anal tissue is delicate. You’ve got to educate yourselves about anatomy, prep and technique — especially if you’re trying to convince a reluctant partner to share their precious starfish with you…especially especially if that partner is a straight guy.

This list is a good place to start — follow the links below for further enlightenment: 

1. Be the honey, not the vinegar.

Rather than pressuring him into this, or threatening to withhold his favorite sexual treats until he acquiesces, or shaming him about not being experimental or adventurous or brave enough, try to sweet talk him into it instead. Explain to him how this is your ultimate fantasy, how much this would turn you on, how much closer you think it’ll bring you two together for him to be so vulnerable with and trusting of you.

If you sense he’s worried about being emasculated, then ixnay on how you just want to pummel that sweet little ass of his. If you think he’s worried about seeming gay, make sure he knows that there’s nothing sexier for you than a guy who’s secure enough in his masculinity to say screw you! to old fashioned attitudes about sex and gender. And assure him that this won’t make you think any less of him — just the opposite, in fact.

Finally, explain to him that you love him so much, you’d love to get as close to seeing from his sexual perspective as possible: if fucking me is so great, why wouldn’t fucking you be amazing, too? 

2. Appeal to his inner scientist.

Male anatomy is male anatomy, whether he’s gay or straight. All men have a prostate gland that can be massaged for not only its health, but its pleasure, as well! There’s a reason the prostate, a.k.a. the P-spot, is called the “male G-spot.”

When stimulated through the top, belly-side wall of the rectum with a finger, a butt plug or a (strap-on) dildo pressing a few inches inside toward the navel or the back of the pubic bone, the happy prostate can make climax even more intense! Who wouldn’t want to at least try that once? 

3. Allay his fears about cleanliness.

If he’s worried about hygiene, tell him you two can plan for any time you want to experiment — no heavy meals 24 hours beforehand, lots of water, little to zero coffee (a diuretic), and some added fiber (psyllium husk powder in orange juice is a miracle worker).

And you won’t start playing until he’s “dropped the kids off at the pool” and had a shower, including his butthole getting up close and personal with his own soapy finger. You can even use medical gloves for any finger probing, which may help facilitate a smoother entry — but then again, may just make him feel like he’s at the doctor’s office. Give him the option, but don’t push it. 

4. If you want to dish it, you’ve got to take.

A.k.a. what’s good for the goose is good for the gander, or in this case, vice versa. If you think he should be willing to try anal sex as the recipient, then you have to be willing to try it out, too.

This is another good opportunity to prove that all anuses, no matter their gender or sexual orientation, are surrounded by enervated tissue and muscle that feels good when it’s stimulated correctly by someone they’re attracted to. 

5. Promise to start small.

You can’t just get a big ol’ strap-on set and go to town. As with all kind of anal play, the giver and recipient have to start out with the basics and gradually work up to more advanced moves. Make sure he realizes you aren’t planning on going in like gangbusters — that, instead, you see this sexual adventure involving taking baby steps along a hershey highway of pleasure that he can take an exit ramp from at any time.

First, you’ll try out some external massage with lubricant; if that feels good, you can try the slightest insertion with a well-trimmed, lubed-up pinkie, reminding him to breath and relax (because a clenched butt is no one’s friend here). If all is going well, upgrade to an index finger. Still okay? Then keep inserting slowly and gently, aiming toward his belly button, until you can feel his prostate and start to gently stroke it in a come hither gesture.

Save experimentation with small, then bigger, butt plugs, for their own dedicated sexual sessions, until he’s ready for a strap-on.  

6. Let him pick out the sex toys.

You’ve got to let him have some say in this fantasy. Together, pick out a progression of sex toys — perhaps an entry-level (ha!) butt plug, then a prostate massager, then a small dildo and a harness, and finally — if he gets into it — his own size equivalent (just not realistically veined if that’s too weird for him!).

Perhaps you’ll find something you both like that vibrates a bit to heighten sensation even further, for both of you! You can vote for a double dildo, to be used with or without a harness, so you can actually get some internal stimulation during your backdoor play. 

7. Guarantee him lots of foreplay and simultaneous stimulation.

You cannot whip out a new buttplug, have him bend over, insert it, and then expect him to explode in orgasm (like this contributor of ours tried). For many (if not most, at least straight) men, they will not climax from anal play alone. They need some attention given to their penises. In many cases, the anal play just enhances the male orgasm that’s achieved through more traditional methods (handwork or oral).

So make sure he knows there’s going to be lots of foreplay before and lots of simultaneous attention paid to his member. His penis will never feel left out!

8. Give him some quick, inspirational reading.

Have him check out this site for all the posts on strap-on love. We’ve had many thoughtful commenters and contributors sing the praises of anal attention within a straight, loving couple.