anal sex / Anatomy/Physiology / Coming Out / Desire / Fantasy

Getting a Girl to Do You in the Butt and Other Quandaries

Hey kittens, it’s Throwback Thursday, so we’re looking at a vintage Sex with Timaree piece that earned the highest amount of traffic on the site in all of 2009.


Question to the Sexpert:

“What do you reckon is the best way for a fella to find a lady that is into pegging? I’d like to whittle down the dating pool, but don’t necessarily want to make this a huge priority (i.e. I don’t want to advertise this on my online personals profile for fear of turning folks off through overt sexuality before I’ve even so much as chatted with them).

I have considered asking my primary partner, but she has expressed that she would not be into it (in a conversation that was not about her rubber dick and my butt). Even if she was flexible, I don’t want to be humored as much as joined.

In case it is relevant, I am not into BDSM.”

What do I reckon? I reckon you bring a number of issues into this here question, pardner and the answer is more complicated than a simple secret pickup line that only girls into pegging will know about.

You: “Hey, you seem cool. Do you… ahem…. like the theater company Pack of Others?”

Her: “Oh snap. You want butt action? You came to the right place.”

And for my beloved readership who are not familiar with pegging: it is the act of a female penetrating a male anally, something we have discussed here previously to uproariously hilarious result. For the record, it doesn’t make the man gay or the woman gay or anybody else  gay, besides actual real life gay people, who rarely want to hear about what hetero couples are doing with their free time.

You’ve laid out the obstacles you’ve encountered thus far on your journey to Buttfuckville, and here is the tourist guide I have amassed for you, in hopes of leading you to the outcomes you desire.


Yeah, yeah, yeah she acted like it wasn’t her thing. That might be the case. It might also be that in the context of the conversation she didn’t think you’d be into it and so she did what a lot of people tragically do every day: pretend to be freaked out by stuff that really doesn’t bother them simply so they don’t look weird.

Every day, across this fine country people waste precious time and valuable sextastic opportunities because they fear rejection. I can picture it right now: a couple that’s been together for well nigh two or three decades, sitting across from each other at the breakfast table, eating their Fiber One, both secretly wanting nothing more than to don full-body latex suits and piss all over each other. They waste away the years, fantasizing in vain, assuming the other would never go for such a thing, maybe even seeking outside encounters with strangers, never knowing what truly magical times they could be having.

Bring it up in the context of fantasy, wondering what sort of things really turn her gears and offering up some of your own as a show of good faith. It’s only through exposing our vulnerabilities and reciprocating with respect and mutually shared secrets that we can build intimacy. She says no? Say, “it’s cool” and drop it. Since you’re poly, you just move on to idea #2.


I know more than a couple perfectly good, committed, loving couples who found each other through adultfriendfinder or craigslist or some equally sketchy sex-seeking site. Sometimes it just works out. You can afford to be picky since you’re looking for more of a romantic partner it sounds, rather than just a fuckbuddy. It doesn’t hurt to try. (Note from Timaree 2014: now you have even more options, like Tindr!)


So you don’t want to mention your fantasy in your online profile. I appreciate that. It does set a tone of being more sex driven than you may actually be, diminishing the number of potential partners who want something with an emotional connection. But there are systems of screening out the sexually squeamish.

Bring up sexual openness in vaguer terms, perhaps even academic ones. Quote Anais Nin, Erica Jong, Henry Miller or some other sexually charged author. Refer to the importance of open-mindedness, willingness to explore and the importance of sexual freedom. Considering that you’re poly, this should be easier for you than for most. If you can bring up the fact you want to be able to bang out other chicks in a profile, this really shouldn’t be that big of a stretch. Girls who can’t hang with the kink will steer clear. The respondents who actually read your profile and pick up on the hint will be more open to the suggestions, even if they don’t actively seek out partners for pegging.


Let’s say your kink was involving balloon animals, red velvet cake and enemas. You’d be much harder pressed to find a fully willing partner, so in that way, consider yourself lucky. But even those folks find someone to indulge them now and then. They usually do so by aiming for partner with whom they click in general and then building trust, intimacy and sexual experimentation into their relationships. It’s a thousand times harder to find a fellow kinkster with whom you’ll fall in love than a loving partner who’s willing to give something a shot.  Good luck.

Questions? Comments? Violent reactions? Email or tweet @timaree_leigh See more at and

2 thoughts on “Getting a Girl to Do You in the Butt and Other Quandaries

  1. Pingback: Yeehaw! Check out the RodeoH! « Sex with Timaree

  2. Pingback: Can You Be Dominant… While Getting Pegged? « Sex with Timaree

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