Bend Over Boyfriends… We’ve Got You Pegged.

by David Wraith

“Bend Over Boyfriend,” written and performed by Elva Maxine Beach

My junior year in high school, a friend of mine came to me with great concern on her face. She’d heard something about me and wanted to know if it was true. She looked me in the eye and asked if I let my girlfriend fuck me in the ass with a strap-on. For the record, the answer was no and it still is. This was 1990, and while I was familiar with dildos and knew enough about human anatomy and physics to know that they could be inserted anally as well as vaginally, I had never heard of or considered “the strap-on.” This was about four years before I met Carol Queen, director and star of the seminal (sorry) instructional video, “Bend Over Boyfriend.”

I was in my 30s before I heard the term “pegging.” It was over dinner with a woman who (for the sake of her anonymity and because I’m not very creative) we’ll call “Peggy Sue.” After our first date, Peggy Sue sent me a lovely photo of herself, naked, stroking her big, purple, strap-on cock. I was charmed, but not converted.

Then, recently, I fished this letter out of the Sex+STL mail bag:

Pegging: I’ve heard of it, but have yet to be fortunate to find a woman that is as attracted to the idea as myself. Is it a fool’s errand?

A fool’s errand? In a word: no. I have the opposite problem of our reader. He’s into pegging and can’t find someone to do it. I’m not into it, and have to keep turning down offers. For insight into the matter, for all you would be peggers and peggies out there, I reached out to my friend Peggy Sue to get the woman’s perspective. She replied, “A bit of a strange request, David, but yes, I would be willing.” So, without further ado:

Peggy Sue’s Pegging Tips:

  • It is something that should not be introduced the first time having sex with a woman, unless of course you have previously discussed it. It is a pretty intimate thing to do and I’m not sure how receptive a woman would be the first time she was having sex with someone new.
  • For women that are new or are wanting to know some basics, the place to start is with lots of lube and condoms or latex gloves and their fingers. Too much friction can cause pain, so condoms help with that and also makes for easy clean up afterward. Also, many women don’t realize that having long nails can really get in the way of having fun. I think that using fingers first is a must. How else are you going to know what you are doing? And fingers are the perfect size to start with. With virgins it is always best to start off small. Same as with the pussy, you have to get it warmed up. Circling around the anus lightly, slowly and then increasing pressure and speed will help with the warm up. Even better yet…make him beg for it.
  • Take your time; it is not a race and once the real actions starts he probably won’t last very long anyway. Reapply lube often. Insert one finger slowly and then pull out. Tease more. Reinsert your finger and slowly push in. If he is on his back you can feel along the top portion on his anus you will feel a large bulb like knob; that is his prostrate, amazing how it is in the same location in women only they call it the g-spot. Rubbing and slightly pushing on this brings about very intense orgasms. And this is great to do to him if he is having a hard time reaching orgasm or is having a problem getting an erection. He may not still get an erection but he probably will have an intense orgasm. You can buy smaller sized butt plugs and that is also a good starting place. I have seen a 3 pack with varying larger sizes, one a little larger than the first and so on.
  • Once you get a strap-on you may want a longer dildo, reach is important and not all of it has to go in. A good position to start is man on top. He controls it and she still has access to his cock. So she can stroke him and he can rub her breasts. I think any woman may feel a little awkward using a strap-on at first, but like with anything else, practice.
  • As far as willing partners go, there is someone out there that is willing, go find them. If your partner does not want to please you then it would seem to me there are other issues going on there. And on the other hand, anyone has the potential to learn new sex skills, we all start off somewhere. Your partner may be willing you just need to ask, or better yet, show her.

If I may interject, every female pegging enthusiast I’ve ever met, Peggy Sue included, has self identified as a Domme. If you’re having trouble finding a willing partner, head over to our links page or our calendar and check out some local BDSM events.

Got thoughts on pegging? Let us know in the comments or drop us a line at sexpositive.stl@gmail.com.

Bye, sexuals.

Posted in ask SEX+STL, David Wraith, men, pegging, women and tagged , , , , .

2 Comments

  1. Great article, love the advice and it’s good to know there ARE women out there that are into this. Now if only I could find one.

  2. Pingback: Sex Positive St. Louis » Blog Archive » Bend Over and Say Hello to Mistress Simone

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