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Dear Kiki: Proceed with caution to enter at rear

Posted by Dear Kiki | Dec 6, 2016 | Arts & Entertainment, Dear Kiki
Dear Kiki

Questions about love and sex in the Iowa City/Cedar Rapids area can be sent to (queries can also be sent anonymously using this form). Questions may be edited for clarity and length, and may appear either in print or online.

Dear Kiki


I am a straight, cisgender female who likes pegging men. How can I meet guys who are into it, rather than dating someone for a month only to find out their butt is off limits?

Thanks, ToppingHim

Hi Topping,

There are a few ways to slice this question. Are you trying to meet a long-term partner who already enjoys pegging? Or are you trying to find hookups to practice on? Are you willing to put in the time and effort to convert your men to a life of taking it up the butt from ladies? Your strategy here will depend on your goal.

If hooking up or dating is the idea, there’s no need to hold back on your intentions. Plenty of men share this interest and you can shake the man-tree of the internet and watch the bums fall out of the sky. Tinder, Feeld (formerly 3nder), Craigslist or FetLife would all be suitable options. When meeting guys IRL, as you’ve probably been doing, it is more difficult to put things on the table up front.

Finding a seriously compatible partner who shares this interest off the bat may be a bit more challenging, so you may have to play a longer game to get exactly the kind of man, and ass, that you want. But the advice is the same for any kind of kink, or any kind of person. If you fall in with a fellow who is not immediately intrigued with the pegging thing, take it easy. Let your interest be known, and work with your lover to get to an agreement on how this will go down.

For many straight guys, conditioning is strong to divert any attention away from their ass, so learning about anal pleasure is a long, slow road — albeit one with obvious benefits for many of them. You probably won’t get many straight guys to agree outright to being pegged on the fourth date, but you’ll probably find that lots of them are willing to experiment with toys and rimming, given time and the correct circumstances. If you can get them feeling good and sexy about you touching their butthole, in a loving and patient and lubed up finger-sized way, it’s far more likely that you’ll get to peg them proper down the road.

xoxo, Kiki

This article was originally published in Little Village issue 211.


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Blog Comments

Good differentiation, and great advice!
Additionally, letting them know that combined prostate and penile stimulation can often result in an orgasm 10 times more powerful than anything they have experienced is not only accurate, but quite persuasive.

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