The Ultimate O with Ash

Wednesday, June 19th 8-10 PM FREE!

Maybe you've never had one, maybe you have but you're still not sure what all the fuss is about, or maybe you're a total orgasm overachiever with an unquenchable thirst for knowledge. Whatever your reason for taking this class, you'll learn all about anatomy, techniques for coming with a partner or solo, how masturbation can help you expand your orgasm, g-spot orgasms, anal orgasms, and, of course, our Sex Specialists' favorite tips and toys.

Sex Specialist: Ash

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Blowjobs and Beyond with Ash

Want to have him squirming in his seat? Our Sex Specialists will show you how to use your mouth, hands, and more to give mind-blowing blow-jobs. We'll cover male anatomy, tips and tricks, the truths and myths of "deep throat" plus other sexy secrets that are sure to have him begging for more.

Sex Specialist: Ash

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!

The Ultimate Guide to Prostate Pleasure with Dr. Charlie Glickman & Aislinn Emirzian

Wednesday, July 10th 8-10 PM FREE!

Curious about prostate play? We'll discuss the common concerns that prevent people from exploring it (and how to overcome them), tips for easy and pleasurable anal penetration, prostate massage, choosing the best toys, pegging, and much more. Whether you're just starting out or you already enjoy prostate play, come learn some new ways to make sex even better.

Guest Educators: Dr. Charlie Glickman and Aislinn Emirzian

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Pegging 101 with Dr. Charlie Glickman & Aislinn Emirzian

Thursday, July 11th 8-10 PM FREE!

"Pegging" (women using strap-on dildos with men) has become very popular, but it's much more fun when you have the info to make it easy. We'll discuss the different options for dildos and harnesses, how to pick the right lubricant, positions for prostate stimulation, ways to include hand jobs, roleplay and much more. You'll learn everything you need to make pegging your new favorite way to play!

Guest Educators: Dr. Charlie Glickman and Aislinn Emirzian

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Performance Anxiety- Comedy Night at The Pleasure Chest

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.

Safe is Sexy with Sarah Sloane

Regardless of how much sex you have, what kind, and with whom, there are many ways to be super sexy while still playing safe. Learn how to negotiate for the safer sex you want. Discover the perfect toys and barriers for sharing the fun. Explore how to keep yourself physically and emotionally happy as you play the field. We’ll share all and bare all. Bring your questions and your ideas to this event, held in conjunction with the PORAE professionals retreat.

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Basic Bondage & Sensation Play with Antoinette

Wednesday, July 24th 8-10 PM FREE!

Learn the essentials of bedroom bondage and sensation play. Our kink connoisseurs will show you the ropes, including how to communicate and negotiate for what you want. You'll discover quick and easy bondage techniques and how to use blindfolds, feathers, massage candles and other items to play with your partner's sensations. People of all experience levels and orientations welcome.

Sex Specialist: Antoinette

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

G-spot and Female Ejaculation with Ash

Looking for an all-over orgasm? Seeking the ever-elusive female ejaculation? This class will provide you with tips and techniques to expand your orgasm, both with your partner and on your own. For years the existence of the G-spot has been rejected while some have hailed it as the ultimate pleasure center; come find out what the buzz is about!

Sex Specialist: Ash

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Butt Sex Basics with Ash

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.

Sex Specialist: Ash

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Performance Anxiety- Comedy Night at The Pleasure Chest

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.

Down & Dirty with Antoinette

Wednesday, August 14th 8-10 PM FREE!

Add some spice to your sex life with our hottest tips and techniques. Our Sex Specialists discuss ways to take your play to the next level by owning your fantasies, learning the art of the tease, and reclaiming the "dirty" side of sex. We'll also share our secrets for G-Spotting, squirting, blow jobs, and anal play.

Sex Specialist: Antoinette

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Sluthood Practicum with Janet Hardy, Author of The Ethical Slut

Monday, August 19th 8-10 PM FREE!

Here's a chance to get answers to some of the pesky poly issues in your life, and to help others resolve some of theirs! Janet has found that group wisdom is almost always wiser than one person can be, so in this class everyone helps teach. Participants will have a chance to submit their questions (anonymously, if desired) about parts of their poly experience that may not be working for them, and Janet will lead a group brainstorming session about ways to move forward toward the abundant poly life you want.

Guest Educator: Janet Hardy, Author of The Ethical Slut

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Warm Cheeks, Warm Heart with Janet Hardy

Tuesday, August 20th 8-10 PM FREE!

Mommy's hard palm, Daddy's big belt, Coach's paddle, Mistress's cane: few BDSM activities are as erotically and emotionally charged as spanking. Whether you're a jaded aficionado or a nervous-but-excited novice, there's always more to learn about the craft and art of butt-whacking. Come discover how to negotiate the scene you want, play the roles that excite you, pace a spanking for maximum pain and/or pleasure, understand your partner's anatomy and physiology, surf the pain so you can accept the sensations you crave, choose implements for sensation and drama, select positions appropriate to your goals, and much more.

Guest Educator: Janet Hardy

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Advanced Anal Play with Sarah Sloane

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.

Sex Specialist: Sarah Sloane

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

The Ultimate O for Him with Sarah Sloane

Wednesday, September 4th 8-10 PM FREE!

Want to blow his mind? In this class, you'll learn the basics of men's anatomy, while exploring the physical and psychological patterns of male arousal. Discover how to expand his pleasure through breathwork and other techniques and learn about the different types of orgasm (penile, prostate, energetic, etc.) This workshop is open to all genders and orientations, but will focus on male-bodied people and their partners.

Sex Specialist: Sarah Sloane

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Tantra Techniques with Antoinette

Wednesday, March 21st 8-10 PM FREE!

Want to learn tantra techniques that will take sex to the next level? We'll cover how to visualize energy and make it your own, while raising and moving that energy solo and with others. Discover different styles of breathwork, energetic approach to orgasm, integrating kink with tantra and more.

Sex Specialist: Antoinette

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Performance Anxiety- Comedy Night at The Pleasure Chest

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.

The Ultimate O for Her with Ash

Wednesday, September 18th 8-10 PM FREE!

Maybe you've never had one, maybe you have but you're still not sure what all the fuss is about, or maybe you're a total orgasm overachiever with an unquenchable thirst for knowledge. Whatever your reason for taking this class, you'll learn all about anatomy, techniques for coming with a partner or solo, how masturbation can help you expand your orgasm, g-spot orgasms, anal orgasms, and, of course, our Sex Specialists' favorite tips and toys.

Sex Specialist: Ash

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!   
detailed info

Blowjobs and Beyond with Antoinette

Want to have him squirming in his seat? Our Sex Specialists will show you how to use your mouth, hands, and more to give mind-blowing blow-jobs. We'll cover male anatomy, tips and tricks, the truths and myths of "deep throat" plus other sexy secrets that are sure to have him begging for more.

Sex Specialist: Antoinette

We do not offer advance registration or reserved seating for free workshops or events. Attendance is on a first come, first served basis. Early arrival is recommended to secure your spot!

The 3rd Annual Art of Sex Show

The Pleasure Chest presents the return of The Art of Sex, our 3rd annual exhibition, showcasing Chicago artists and their sexiest, most provocative work for your perusal and purchase. Whether your taste is subtly sexy or overtly kinky, you're sure to find something that you find… inspirational. Meet the artists over wine and cheese and shop for things that will help you discover your own art of sex!