Cherry Popper

Based on my experiences of the last six months, you'd think I was chasing down the title of Anal-Fisting Cherry Popper (AFCP). I don't know if there is someone out there already considered (albeit unofficially) AFCP, but I think I am in the running to dethrone whoever it is. Since I teach anal-pleasure workshops around the country, I've, naturally, had requests for classes that cover the whole, um, hand-chilada. In the name of sex education, I get a good manicure, pack my bags, and travel to new cities, where I lecture on safety, preparation, and the wonders of there's-no-such-thing-as-too-much-lube. But talking tips and techniques doesn't always do justice to this five-finger subject, so, when possible, I also perform hands-on (more like hands-in) demonstrations. And lately, I have been on a roll.

To many, Anal-Fisting Cherry Popper might sound like a homo porno series, conjuring images of Crisco-coated arms disappearing into hairy buttholes as deep trance music plays in the background. That's because dipping into the bunghole is most often linked with gay leathermen—they popularized hand-in-the-butt love in the 1970s, and have been its main practitioners and teachers ever since. But the rest of the world has caught up with queer boys with short nails, and there is much more interest in this subject from folks who don't even know what a red hankie in your pocket means. Case in point: I mostly teach and demonstrate on heterosexually inclined women and men, as well as lesbians.

Since I don't have an anal-fisting demo bottom who travels with me everywhere I go (résumés for such positions gladly accepted!), I must rely on the kinky kindness of strangers in most cities where I teach. The usual scenario goes something like this: I tell the organizer of my workshop that I need a volunteer for either of the two classes I teach, "BDSM and Anal Play" or "The Art of Anal Fisting." I arrive in the city, and if I'm lucky, I get the chance to meet and talk with my willing ass-for-hire before my workshop. More often, I've got about a half-hour to assess their experience, negotiate limits, and form some sort of connection before I dive in. Inevitably, my demoee informs me that he or she is "an anal slut," a "butt pirate," and "a total exhibitionist." The thing that most people forget is that we are not having sex or doing a scene in the traditional sense: I am teaching a class, in which my focus is constantly split between the person with his or her ass in the air, and the students with their hands in the air (to ask questions, of course). I cannot devote 100 percent of my attention to my bottom, and the audience is always a part of our experience. I've probed some asses that are tighter than Air Force One security, and no amount of arousal is going to relax their sphincter muscles, but I am skilled at making the best of less than ideal situations. Overall, few encounters have been mediocre, and most have been incredible.

There's Annie, whom I've done twice; she's sexy and fun, and I nicknamed her Miss Giggles. Both times, when I put a butt plug in her ass to illustrate ways to warm up the butt, she laughed so much that it popped right out, giving me the perfect segue to talk about how to keep a plug in. And then there's Vena, who had been doing lots of anal play with her girlfriend in order to prepare for my workshop. But nothing could prep me for taking out a thick plug from her ass, lubing up my gloved hand, and finding myself slipping all the way inside her so quickly. The audience was flabbergasted, and I tried to play it cool, like, yeah, this happens all the time, but secretly I was thinking, "Damn, she's making me look good!" I met Adam when he gave his bottom up for education last year. Although he looked so nervous before we began, once we got into it, he took my hand like a champ.

At one event, I was scheduled to teach two classes in one day. I became so smitten with my demoee, John, in my "Anal Sex 101" class in the morning that I put a butt plug in him and told him to leave it in through lunch and return for my advanced class in the afternoon. He was sweetly submissive, looked me directly in the eyes, and communicated well about what he needed to make it happen. When I got my whole hand in his ass, I was transported. I looked up at the crowd of people watching, and for a moment I was speechless. There are no words to describe the feeling of having your entire hand inside someone's ass. It can be simply magical when our bodies are joined in that moment. (To top it off, after the workshop, John sent me a "thank you so much for fisting my ass" note on cream-colored embossed stationery that would've made Miss Manners proud.)

Of the 10 people I've recently anally fisted, only one had been anally fisted before me; likewise, only one of my demonstration volunteers had ever been fisted; the rest of them volunteered to let me plow them for a crowd. How gutsy! To know that a stranger could be the one to pop your anal-fisting cherry! I have very small hands, seven inches from the tip of my middle finger to my wrist and seven and a half inches around (yes, that was a blatant advertisement), and size does matter.

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