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Get Cheeky With Us During Anal AugustFree Workshops & Comedy in Chicago

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by thepleasurechest

Anal August is here! It’s an entire month devoted to celebrating butt play, from spanking and teasing, to pegging and pleasing. In addition to our lineup of free butt-focused workshops, we’re hosting the return of the Performance Anxiety comedy night. Read down below for a complete schedule of free events!

Butt Sex Basics with Sarah Sloane
Wednesday, August 1st @ 8-10pm FREE!

In this workshop, no topic on taking it up the ass is taboo. Learn why a warm-up is important before anal exercise, why lube is your butt’s BFF, and how building comfort and trust with your partner can dispel common concerns such as pain or cleanliness. We’ll show you our favorite toys, how to use them solo or with a partner, cover the perks of having a prostate, anal g-spot stimulation, and toy and partner safety.

Bend Over Buddy with Antoinette
Wednesday, August 8th @ 8-10pm FREE!

Is your bedroom buddy just begging for a pegging? In this workshop, we’ll teach you how to get your guy on-board for some ass loving. If you don’t know how to approach the subject (or their sphincter), we’ll give you tips on communication, the pleasures of perineum and prostate play, strap-on sex, anal sex safety, and the best toys and tricks to arouse him anally. This class will focus on bending over your boyfriend, but all genders and orientations are welcome.

Spank Someone Happy with Antoinette
Wednesday, August 15th @ 8-10pm FREE!

Looking to make your sex a little naughty? Let our Sex Specialists bring you into the wonderful world of erotic spanking and role play. We’ll show you how to combine spanking with sex in a fun and consensual way. This workshop is perfect if you’re feeling curious, need help getting started, or just want to fine-tune your technique.

Performance Anxiety-Comedy Night at The Pleasure Chest
Monday, August 20th @ 8-10pm FREE!

Get your laughs and lube in the same place. Join us for Performance Anxiety, a comedy night hosted by Caitlin Bergh and Rhea Butcher and featuring live performances by some of the best comics working today. As a bonus, all audience members get 15% off their purchases on the night of the show.

Advanced Anal Play with Sarah Sloane
Wednesday, August 22nd @ 8-10pm FREE!

For those who like to push the boundaries of butt loving, we’re excited to offer this advanced workshop on everything from anal douching and enemas to safe and sexy anal fisting. We’ll cover smart ways to engage in extreme ass play, double penetration for all genders, and help dispel the myths and shame around this enjoyable orifice.

Coming up…

9/5- Talk Dirty to Me: Roleplay & Fantasy in the Bedroom with Antoinette

9/12- G-Spot & Female Ejaculation with Sarah Sloane

9/26- Suck it, Lick it, Love It with Antoinette

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