So you want to peg or get pegged? 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 man interested in getting pegged, check out our article here.
Getting Started with Anal Play
Similar to our other article, you need to start with anal play. Some men have a very strong aversion to this thinking they are “gay” if they were to submit. But while giving a blow job you can always have your mouth and hands roam. Just a flick of the tongue while giving his balls attention, or a little pressure near the asshole while cupping his balls is a good place to start. Almost like its an accident. Keep the focus on the hand/blow job and make sure he really enjoys that. If he is receptive, then work your way a little more into that each successive time. Also, I find that talking dirty is always a turn on. If you don’t already tell him how much you love his cock and sucking it or how much you love licking his balls, start there. Then if he is a little receptive to the ass grazing, you can tell him how much you love his ass and you can kiss his ass cheeks and give them playful bites. Once again, slow progress is key until you get positive feedback to move forward. Then you can tell him how much you love licking his cute asshole. As you move to penetration with your finger, make sure you do that very slowly. Start by playing around on the outside (plenty of good nerves there), and make sure your finger is sloppy wet with spit. I would say lube, but remember this is supposed to be accidental/heat of the moment stuff at this point, not planned. At least that is what he needs to think. Keep the focus each time on him cumming from a hand/blowjob and listen for cues that he likes what you are doing, maybe a small moan you have not heard before.
Push a little further (and deeper)
As you go further and further into his ass (literally speaking) each successive time you should just do some slow penetration in and out with one finger. Do some reading on where the prostate is, that is your goal as you move in deeper each time. If he likes the ass play, then use some lube in the future to hit that prostate and try to have some open conversations about how you heard from your friends/girlfriends/coworkers/book/magazine/etc that the prostate can be very pleasurable for a man and you want to hit it. If he is laying on his back, stick your finger in and curl it up in a come here fashion. There will be a smooth wall of tissue inside his ass from his asshole to his prostate. As you work you way up that tissue, you will run into a walnut sized bump, that is the gold! Slowly massage that, while giving him other stimulation if you can. If you cant do both at the same time, just get some pressure on the prostate and push on the center high point of it. He should moan a little and really enjoy it. Massaging the prostate can also be called milking the prostate because it will force a little milky ejaculate fluid out. This is not him cumming (yet), but he will much enjoy it. Make sure you ravenously slurp that up and tell him how good he tastes. Remember, he really needs to see that you enjoy it and he needs to enjoy it.
Be Prepared
Now, keep in mind ass play can be a bit messy depending. Most people know if the need to poop and will do so, but if you can keep a darker cleanup handcloth nearby just in case, it is not a bad idea. You might get a little bit of poop on your finger and you need to make sure that is not an issue for you and he does not see it as an issue.
Time for Some Toys
Once you get him comfortable with all the finger ass play, do it for a while. Make him want it. Then you can introduce toys. Pegging is a lot bigger of a toy than your finger. You need to work his ass up to it and his acceptance of it. You can start with some smaller butt plugs, or multiple fingers. Tell him that you see he enjoys ass play so much and you do too, so you want to buy yourself a little ass toy you can wear while he fucks you. Maybe you look at this together and this becomes part of broaching the topic of looking at sex toys. Find a butt plug set you can work with. Then as you wear one and work your way to the larger one, you could try a smaller one on him while giving a blow/handjob. Pick one that is not much bigger than your finger and make sure you:
- Play with his ass first and get him hot.
- Use lube all over the toy and his ass AND
- Go slow!
A bad anal experience can turn anyone off for a very long time. Even if you have put a certain toy in his ass before, you will need to make sure you work him up to it each and every time. The ass is elastic, but that also means it tightens back up within a matter of hours. So always stretch him out with multiple fingers before you try a toy that is bigger around than one finger, because it can HURT when you aren’t ready for it.
Once the toy is in his ass, just push on it a little and lightly move it around while pleasuring him. At this point you should be pretty good at picking up on cues he is giving.
Go Bigger
Now work him up to bigger plugs/toys slowly. This is when you could buy a strapon compatible toy that is thin like the plugs you have played with or about the same size if you have been graduating him. If he has fears of being “gay” then make sure you get one that does not look like a penis at all. As with before slowly start to use this on his ass to fuck him and see if he likes it. Prostate toys are also a great option, get him something he really likes and use it on him. Either way, you are just getting him more and more comfortable with the feeling of things in his ass while he is in sexy hot situations with you.
Lets go Shopping!
You can either head back to the toy web site and do a search together on “Best Sex Toys for Him” or a search that helps you trip across a few strapons in the results. As you look at that together in bed you could casually mention, “ooh that would be hot for me to fuck you for a change,” or whatever you think will peak his interest. Don’t force it yet, if he seems uneasy, then keep looking at other butt toys and find something else he might like. This may be a topic you don’t bring up again for a couple months. But at some point it will feel right to bring it up again Maybe this time you can say you ran across some articles on this thing called “pegging.” Tell him it is when a hetero woman fucks her straight man with a strapon and it is really becoming a mainstream thing as men start to discover the pleasure they can get.
