April is focusing on the the female side of the equation...

Anonymous has left a new comment on your post "Need Some Questions From The Ladies":
"Here's one for you: I want to "peg" my husband. His response: no way.

How can I have my way with him? I want his "man cherry!" I want to experience, in some small way, what sex is like for a man — the dominance element that seems to be such a major part of sex for many men.

Not joking; any helpful advice would be appreciated."


For those who don't know - "pegging" is when a woman wears a strap on dildo and penetrates the man's anus with it. It can be pleasurable for the woman in that the base of the dildo can apply pressure to her clitoris and if it's a double ended dildo, then it also gives sensations inside her. For the guy it can be pleasurable anally and especially on the prostate.

So I'll answer this question in two ways, (1) finding a way of getting that feeling of sexual dominance and (2) shoving things up his ass.

If you really just want that feeling of sexual dominance once in a while - to be the one supplying the sexual pounding instead of the one of the receiving end of it - there's a couple of ways of doing that without cramming things into his ass.

One easy option is to tie him up. Once he's tied up, you're pretty much the one that's dominant and making things happen. Suck him, sit on his face and wriggle a little bit, tease him, kiss him and finally make him cum in a manner of your choosing. Ta-da! Easy dominance.

Another option is a variant on the Cowgirl Position. Do Cowgirl for as long as you like, but then lean forward over him, have him spread his legs apart and put your legs inside his ones. So now you're in a Gender Reversed Missionary Position. Having your legs together and tensed to support your body weight is going to tighten your vagina on his cock and create a stronger sensation for him. You on top and him under you is you in a dominant position. Then you pound his cock with you vagina.

Jennifer and I do this position once in a while and it really does provide a highly stimulating experience. This is about the only Penis-in-Vagina position where I have no ability to control my orgasm. Me on top, spoons, cowgirl or whatever, I can slow just a little or mentally adjust and not orgasm until I consciously choose to. In this position Jennifer can just fuck me hard and I can't not cum. So she's dominant in that position.

So anyway... assuming you actually want to boldly go where no one has gone before, some tips for that.

Start small. I'd start with handjobs that have an element of anal play with them. Using a good amount of lube, have one hand jerk his cock and the other gently play with his anal area. If he likes that a few times, then you can progress to inserting a finger into his ass as you do that. You can use gloves or a condom as a barrier.

For anything going into the ass you need a lot of lubrication. Too much is better than not enough. I would use your middle finger and assuming he is on his back, your finger goes in and gently "up". You're looking for his prostate gland and it will feel a little like a small soft bump against the rectal wall. You will know when you hit it right because your husband will probably have his eyes bug out and look at you like he just discovered he had a secret second penis or something.

You can gently stroke and play with the prostate - long nails are a no-no though. You don't want anything sharp poking at the rectal wall and scraping or puncturing anything. That's a nasty recovery. Another option here is a small, repeat small, butt plug. Should cost you about $10. Same deal as fingers in the ass, lots of lube. Basically thrust it to try and hit the prostate. It's good with a hand/blowjob going as well. Most men have huge orgasms from prostate stimulation. Just take it slow.

After that, you can build up his tolerance with a larger butt plug and eventually get up to pegging. That takes a lot of trust though. You're going to have to make him want that experience by having lots of good anal sexual experience leading up to it.

Jennifer and I have done all of this with the exception of pegging. I loved prostate orgasms when I was early 30's, but not so much now I'm 40. I think I'm just starting to get nervous about damaging myself in someway, a too firm poke at 30 and nothing much might happen, at 40... ya getting nervous I think.

I do like having my ass played with once I'm turned on and there's lube involved. We do anal toys once in a while and I handle a small one easily. We tried a medium butt plug on me once and that was just amazingly painful. It was kind of like me fucking Natalie Portman, the fantasy was exciting but there was just no way it was ever going to happen in reality.

Oh and be advised. You peg him, he can quite justifiably demand you put your ass up in the air and he gets your anal cherry too. I suggest you experiment a little on yourself and see exactly how big you can really tolerate in there before you set the hamster wheel in motion.

So have at it. It doesn't have to be man on top every single time. Try stuff out together, if it works, it works. If it doesn't work and it was anal, go easy on the spicy food for a day or two. Anyway... if she doesn't get her kink on with you, who can she get it on with? Her memories of band camp will only sustain her for so long...




As an aside, anal prosthetics sales are an exciting growth area in the medical field. It's quite possible to seriously damage yourself with anal sex, so be careful with it. Please don't make me link anal prolapse accident porn from the nastiest places on the Internet. Nobody wants that.