Most hetero men are more or less protective of their behinds. Yet, after dropping those initial inhibitions for anal play and with careful steps, most will learn to thoroughly enjoy the occasional anal play. Maybe it’s for your man – maybe it’s not. Only one way to find out, I would say.

Spoiler alert: None of the guys I know were any less manly after some ass play, none of them became gay because of it, but I dare say most would miss anal fun once they experienced it.

Let’s look at four steps how to start slow opening up a new world of pleasures with your guy.

1Grab That Butt

Men generally love a good old squeeze of their bottoms, grabbing it – say whilst giving a blow job or just during foreplay. You can test the anal-readiness of your guy by squeezing a bit lower. When you spread the butt-cheeks and push them back together, you massage the anus ever so slightly. A great way to see what response you get – especially during a blow job, there is no hiding if he likes it or not.

2Tender Massage

Massaging the perineum – that’s the bit between the balls and the anus – is am effective technique supporting hand and blowjobs. Try coming closer and closer to the anus to gage his arousal and finally massage the anus itself – don’t be too gentle with the pressure so you don’t end up tickling him.

Your man might get giggly or squirmish now, because of that ‘nothing goes up my ass’ attitude. Dirty talking whilst giving hand and blowjobs can be a great way to assess if you can go further. “I want to play with your ass, would you like that? How about if I just massage you right here, does that feel good?” Obviously not with your teacher-voice, but with the ‘wtf where did that slut come from’ voice.

3Pinky Play

Anal penetration is where new-to-anal-guys get touchy. That’s why starting with the pinky is a good idea. Assuming that the pinky is well manicured and ideally lubed. The first is important for health reasons so you don’t hurt the anus, the latter is just common courtesy 🙂 And if he likes it, try other or more fingers.

4The OMG Gimme More Spot

Men do have the equivalent to the female G-spot: the prostate. It’s super easy to find, once they let you fiddle around with your fingers up their ass. Pinky will probably not do, so try the index finger – remember, trim those nails. The prostrate is essentially on the upper end of the whole genital area. So if you make a beckoning motion with your fingers, facing front, you should feel a soft bubble spot at the end of your finger. Keep on ‘beckoning’ whilst giving a blowjob or hand job and your partner will get to totally new levels of orgasm.

Congratulations if you have gotten this far. Trust me, he will love you for spicing up his sexual experiences. If your man likes these simple practices, and you two like the idea, maybe you are ready to try some advanced stuff. There is a whole world of anal sex toys for men and techniques out there. And if you like to play more kinky, you could even try a strap-on and who him who’s boss 😉

Sonja is a co-founder of boldpleasures. She's on a mission to free people to revel in their true sensuality by removing the stigma surrounding kink. Sonja writes about first steps, ditching the shame and how to combine kink and 'normal' family life. She's a mother of two.


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