Pleasure Activist

Charming the Snake: An Interview with Jessy Schmidt

This is a discussion-based workshop about—surprise, surprise—pleasuring the penis! As Jessy Schmidt points out, many people buy into the idea that penises are these simple, practically self-operating creatures with crude and narrow pleasure pallets. While this may (or may not) be good enough for some, this view is a one-dimensional approach that compartmentalizes the penis as some isolated and externalized sex organ, rather than an extension of the whole sensual body. While discussing a wider and more nuanced variety of sensation techniques that also includes the use of some fun toys, Schmidt also contextualizes penis pleasuring as a holistic experience that includes much more than direct physical touch—such as the process of seduction, teasing, and charming!

Ally: I know coming up with a name for this workshop was a bit of a challenge. It's a "penis pleasing" workshop, but that feels so unidirectional. It leaves out the rewarding pleasures of confidence, a sense of sexual mastery, and empowerment that comes with eliciting pleasure in your partner. "Charming the Snake" gets some of that sense of power in there, but "snake" can evoke a potentially dangerous creature. What were some of the challenges you encountered with this process?

Jessy: I always want to be as inclusive to all bodies, orientations, and gender presentations as possible. It's important to find language that doesn't seem like it's cutting someone out. This is why I specify the genitalia rather than the gender—which in this case is "penis" versus "man." Folks all across the gender spectrum may have penises and I want them and their partners all to feel welcome at the workshop! And this is why I've stayed away from titles like "Pleasing your man."

I like "Charming the Snake" because I think snakes are super sexy creatures, with their sensual, feminine sway and their phallic shape. They bring together elements that are often presented as opposites.

Ally: What's going to be covered in this workshop?

Jessy: Well, people tend to think of penis pleasing, along with male/masculine pleasure, generally speaking, as very simplistic - just a bit of up and down, in and out, and you're good. But really there is so much more! We're going to bring the whole body into the penis pleasing experience—while also going over the specifics of anatomy and various techniques folks can try on the penis-toting people in their lives!

Ally: What are some reasons somebody would want to come to this workshop?

Jessy: They may feel overwhelmed, unskilled, bored, curious, or interested in adding to their repertoire. They may want to come to learn new techniques, share what they have experienced, or see what other people are up to. They may want to come, in general, to revel with fellow sex-positive folks! All are welcome!!

Ally: Do you have any interesting piece of trivia about penises or penis pleasing you can share with us?

Jessy: Yes! Do you know that seam that runs along the perineum, across the scrotum, and up the bottom side of the penis? Well, that is a really cool souvenir from prenatal genital development. Until about six weeks of development, fetus genitalia is completely undifferentiated and has the potential to either develop a penis and scrotum, a vulva and vagina, or other variations of genitalia. At this point the non-gendered external genitals include a genital tubercle and labioscrotal swellings or folds. A combination of genes, chromosomes, enzymes, and hormones determine whether these labioscrotal folds will fluff out and develop into the labia majora, fuse together to form the scrotum, or in rarer cases, develop into any number of different genital formations, as is the case with some intersex folks, who may have a chromosomal make up other than XX or XY and/or differences in their genes and hormones.

In XY folks, this fantastic labioscrotal fusion leaves behind its mark in the form of a deliciously sensitive seam that starts at the anus and extends all the way along the scrotum to the base of the penis. Not only is it a fun reminder of how homologous all of our genitals are, but it can also be a very sensitive and stimulating line to play with. Do remember that every body is unique so make sure to ask your partner(s) what they like and/or go slowly if you are discovering this together!

Ally Booker is a pleasure activist. You can often find her at her Tucson shop, Jellywink Boutique, 418 E. 7th St.. You can 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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