Pleasure Activist

It’s Anal Pleasure Month!

Part 1: Interview with Jessy Schmidt

In 2013, the good folks over at Good Vibrations declared August as “Anal Pleasure Month,” but we sometimes call it “August Anal” or “Anal August” for an alliterative good time. It didn’t take long for this relatively new event to gain popularity, and really, it’s no surprise considering many of us don’t need any excuse to turn anal pleasure into a joyous month-long observance. For our part, Jellywink Boutique will be hosting an anal pleasure themed workshop facilitated by Jessy Schmidt on Sunday, Aug. 16 from 6:30 to 8 p.m. This is a discussion-based 101 level workshop that will cover general information including warming-up/training-up; how to optimize comfort, safety, and pleasure; how to communicate and/or introduce your desires to you lover; lubes, toys, and other implements; and any questions that folks may bring to the table. You can reserve your spot on Eventbrite.

In the meantime, here is the first part of a two-part interview with Jessy discussing backdoor fun:

Ally: What are all the things that will be covered in this workshop?

Jessy: Or uncovered as it were! (wink)

I kid. No nudity in this workshop. Plenty of information, though, including anal anatomy, pleasure and safety, strategies for communication with partner(s) about such things, a bit about myths and truths, plenty of tips and techniques, and toys, lubes, and time to talk stuff out!

Ally: What experience are you bringing to the table?

Jessy: Mostly pegging. It is pretty amazing to be able to penetrate male partners, for them and me. My own tender bud is a little ball of tension itself, so I have some relaxation work to do before anything sizeable is going in there. It’s a goal. I’ve learned it’s best not to rush these things, so I’m not.

Ally: I remember a questionnaire from another sexuality educator about women’s preferences regarding erotica content. Anal sex won under the least favorite erotica content. However, anal sex also won under the most favorite erotica content! Can you explain why anal sex is so divisive?

Jessy: There are a couple of things at play here. First, there is the scat factor. We are taught from a very early age to equate our butts with poo, and since poo comes from our butts, they must be dirty places where we should never, ever play. So people have this idea that they are doing something really dirty and unsafe when they go back there and much of the information in the world still confirms that idea. Some folks think that makes it extra fun and sexy and some folks are totally freaked out by it. Add those who’ve had unpleasant, painful experiences, often because of bad information or unrealistic expectations, and it’s totally understandable that there would be such a... crack. 

On the other cheek, there is the homophobia/misogyny factor, this idea that being penetrated makes us weak or lesser or dirty, especially being penetrated a lot, and/or in more than one place. This idea can be hot for some folks and scary for others. There’s a lot wrapped up in it. I think it’s powerful to be able to open up to another person. Not everyone can do it. 

Ally: (Side note because not too many people will say this, butt I do love your puns!)

I’m guessing that most people reading this know what “pegging” is since this column is published right next to Savage Love and that column is the creator of this term. However, there is always the next generation, or those who missed that era of Savage Love, so how about you explain what pegging is as well as some other interesting info about it?

Jessy: Absolutely! Pegging was coined by a Savage Love reader in 2001 as a name for a specific kind of anal intercourse, where a woman straps on a dildo and penetrates her male partner for their mutual pleasure and delight! It’s great for many reasons, not the least of which is that both partners get to experience what it’s like to take on the role of the other, assuming they haven’t otherwise had that opportunity. Women get to pitch and straight men get to catch. It changes people’s view of sex. Women are often surprised about how strenuous and stressful it can be to be sticking something into someone else’s body. Men often really appreciate knowing how vulnerable it can be to take something into their body, and how easily it can become uncomfortable. People say it makes them better lover to the other. 

Ally: I wonder what other role reversals we could do with our lovers to help us learn more deeply about them? I’ll earmark that as a topic for another article.

Join us for Part II next week. We hope to see you at the workshop!

Ally Booker is a pleasure activist, passionate about educating herself and others on sexuality and things like communication, sexual self-determination, destigmatization, gender and sexual expressions, sex toy use and other mechanics of pleasure. You can often find her at her Tucson shop, Jellywink Boutique, 418 E. 7th St. Reach her at 777-9434 or

About The Author

Ally Booker

Ally Booker is a pleasure activist. She is passionate about educating herself and others on cool sexuality related things like communication skills, creating and respecting boundaries, sexual self-determination, destigmatization, gender and sexual expressions, sex toy use and safety, and all the other mechanics...
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