So you want to ask your girlfriend to peg you? Broaching this topic can be tough. To some ass play is very taboo and almost a turn off right away. But, where there is a will there is a way. If you are a woman interested in pegging your man, check out our article here for a little direction.
Even if you want her to shove a dildo up your ass, don’t worry, you are still very much a man.
First Lets Get Her Comfortable With Her Ass
If your girlfriend isn’t very comfortable with asses or you haven’t explored that yet, then this is where to start. You need to find some ways to warm your partner up to the topic, slowly. It is good to start with a little anal play on her. Give her ass some love (and kisses)!
Note: The ass contains some bacteria that may not make you sick, but can throw off the balance of a woman’s vagina. So after licking her cute little button hole, don’t lick that pussy until you clean your mouth out. Same thing goes for your fingers and cock. Don’t double-dip without a washing in between.
Depending on how you like to fuck, any number of introductions can happen. If you are eating her pussy, maybe you can have a sloppy finger gently slip around her asshole (don’t go in yet). Or you could let your tongue wonder around down there after you finish eating her pussy and just before you fuck her. If doggystyle is your thing, then pull her ass apart a little so you can see that cute butthole and you can also slide a wet finger around it while she is in the heat of it.
Key points here are:
- Make sure she is aroused and hot, don’t jump right to butt play cold or without other stimulation.
- Plenty of lube, start with your spit while playing on the outside so you don’t have to pull out a bottle of Anal lube in front of her.
- Keep it light and on the outside the first few times, don’t try to shove your fingers in there right away.
- Tell her how hot her body and her ass is, kiss and caress her ass cheeks and make her feel sexy.
You may never need to actually finger her ass, she may not be down for that, and that is fine. But, you DO want her to realize that the ass is an erogenous zone (a place of pleasure) and a place that you are very comfortable with.
Next Let’s Get Her Thinking About Your Ass
Once you ass play on her is part of the routine, you now need to see if she can reciprocate. If she is giving you a blowjob or stroking your cock, ask her to massage your perineum (area between your ass and balls) and eventually your ass. Just tell her to rub around on the outside. Same as you did with her, let her work her way up to it and gauge her comfort level. As with her ass, don’t force her into something she doesn’t want. You want her to WANT your ass and to know it brings you pleasure!
A Little Penetration
So hopefully by now she is at least curious about your ass and knows that it brings you a little pleasure. Now see if she is down to put a finger in. While laying in bed, you might take the time to browse here or here and share your phone with her. Both articles are on the prostate and are from mainstream sources like WebMD, making them less threatening.
From there you can get her to explore more with her fingers, you might need some lube, so order up a little Sassy Sliquid. Once she finds that prostate, life is good. As with all of this, take some time on this step and enjoy it. Make sure you take good care of her though sex is all about reciprocation.
Intro to Toys
The next step is toys, but for her! Do you ever look at sex toys together, or can you make an opportunity to look at “sensual massagers” that end up showing a few sex toy results? Once again, sometimes laying in bed on a weekend is a good time to look at this stuff. The prior link takes you to an Amazon search on sensual massagers, page one has some good personal massagers and a few sex toys, then on page two it dives a little deeper and you get into clit suckers.
At this point you really need to know your partner and don’t push it. If she is comfortable with just getting a little personal massager, great, start there. You just need to start building your toy box and any addition is a start. If she wants to explore a little more, maybe she wants to try a clit sucker.
Note: You cannot feel threatened by her getting sex toys otherwise she might feel threatened as well when you want to get some toys. It is good to have some open dialog that you want to use the toys together on one another. Or if you are OK with them masturbating without you and using the toys, set that clear expectation. But make sure both of you are in agreement.
Now that you have the first toy in your toybox, have some fun with it and make sure she really enjoys it. Focus on her.
After a few fun sessions, it might be time to mention that you are interested in a toy that she can use on you. While in bed or in a sexy mood, do a quick search for “Best Sex Toys for Him.” Start searching, as you dig into men’s toys you will inevitably come across prostate massagers and go from there. Just be patient and slowly steer her in that direction. If she was open to reading the article on prostate orgasms earlier, then she is likely going to be receptive here. Order up something that gets your fancy and hers and have fun. Once again, keep getting her more and more comfortable.
Shall we Peg?
OK, time to head down the final pleasure road toward your goal. Once again, you should share some mainstream articles like this one from Healthline on how pegging is going mainstream. That should really help lower her guard. Tell her you think it would be really hot to try it out. Then go exploring some toys. You can start with something basic like a strapon kit with both a harness and dildo. This is a low cost entry point and you can always spend more from there. But start simple, and then expand your toybox.
Good luck to all! Pegging is great.
