Discover Classes. Earn 10% Rewards.

Pleasure Chest
Upcoming Classes in Chicago

(4.3-star rating across 26 reviews)

View School's Profile

Pleasure Chest

Unfortunately, no classes have spots left

Booty-palooza

Pleasure Chest

Looking for a booty-full start to Anal August? Stop by your favorite neighborhood sex shop and enjoy tasty treats, mimosas, and some free mini-workshops that will help you delve into your deepest fantasies! One lucky Pleasure Chest shopper will win a $250 Ass-tastic Gift Basket! 2:00: Butt Plug Basics — How to choose, wear, and get the most fun out of your plug 3:00: Anal Sex Achievers — For the giver and receiver, these tips will help you...

(26) All levels 18 and older
No upcoming schedules

Butt Sex for Beginners

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Ready to explore the final frontier? Our sex specialists have the knowledge you need to make your fanny happy, from positions to plugs to prostate play. We'll teach you how to warm up your butt for a good time, fill you in on the best toys and lubes for solo and partnered anal play and address common concerns about comfort and cleanliness. Bums away!

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Advanced Anal Play

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

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.

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!
Discover Classes. Earn Rewards.

CourseHorse Gift Card

Thousands of classes & experiences. No expiration. Gift an experience this holiday season and make it a memorable one. Lock in a price with the Inflation Buster Gift Card Price Adjuster™

Buy a Gift Card

Episode IV: A New Rope

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

There are lots of "Rope 101" classes for beginners, and they're fairly standard in what they offer, unchanged from the early days of the San Francisco, NYC, and Chicago scenes of the mid-80's. Graydancer challenges that paradigm in this class, based on research conducted all over the world with rope instructors. This is the "Rope 101" that they wish they'd had, with the extraneous or erroneous or boring stuff left out and the juicy sexy...

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Introduction to Tantra

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Learn tantra techniques that will take sex to the next level. This class will introduce you to ways to create and use sexual energy in the bedroom, solo or with a partner. Discover different styles of breathwork, energetic approach to orgasm, integrating kink with tantra and more.

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Getting Cocky

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Want to learn the techniques that will assure stronger, harder, longer-lasting orgasms? In this class, Louie will discuss the anatomy of the penis (and beyond), toys to use alone or with partner(s), how to communicate your desires, and how to increase your libido. This workshop is open to anyone interested in learning new ways of getting off, staying harder longer and how to have those elusive multiple orgasms (oh yes, it's possible!).

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

A Field Guide to Shaking Things Up in the Bedroom

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Join educator and author Jenny Block to explore the ultimate art of the blended orgasm! Learn more about procreative sex vs recreational sex, how the media effects our sex lives and why what you see isn' t really what you want when it comes to sexual play. Plus, discover more about the connection between mind and body, and unlock the mysteries about getting your head in the game to discover the best sex of your life!

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Playing with the Family Jewels

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Join renowned educator and author Hardy Haberman The Family Jewels: A Guide to Male Genital Play and Torment to learn everything you ever wanted to know about CBT (cock and ball torture). This class covers the basics for anyone interested in tormenting a male partner's naughty bits. Hardy will discuss safety, health and anatomy, toys, activities, and using CBT as a way to spice up any scene. Demos are a big part of this class and they are always...

(26) Beginner 18 and older
No upcoming schedules
Free
Gift it!

Putting the Sex Back in SM

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

How many times have you heard someone say that BDSM isn't about sex? What? To miss the erotic aspects of SM is to lose the full impact of the experience. The class will discuss ways to create a more erotic experience from SM play and ways to enhance sexual aspects of the scene. Additionally, the class will explore why sex doesn't have to be “Part A” into “Part B” to be enjoyable!

(26) Beginner 18 and older
No upcoming schedules
Free
Gift it!

Exploring Domination & Submission

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Rihanna told us we could be bad, but are we perfectly good at it? If you're curious about bringing some spice to your relationship, let's talk D/s: Domination and submission. Whether you're looking to renegotiate an existing relationship, start a new one, or bring some power play to the bedroom for one night, we'll talk about how you can incorporate D/s responsibly and ethically into your life. We'll go over basic terms like Dom/Domme, sub, slave,...

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Couples Massage

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

This class will give you all the skills needed to perform an awesome massage. Learn how to deliver the right amount of pressure without hurting yourself or partner, how to avoid tired, achy hands, and the best practices for communicating your needs to your partner.

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Sex Toys 101

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Did you know that using lube can enhance and prolong your sex? Want to hear about the best condoms for sensational safe sex? Valentine' s Day comes once a year, but you don't have to. Discover the best toys for getting romantic and getting off. We' ll have some wine and cookies for you to enjoy while you learn & shop, and a chance to take home your very own sex toys goodie bag, courtesy of Pleasure Chest. Topics include: vibrators for beginners...

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Queering your Sex

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

This class is geared toward all gender-variant, gender curious folks, or anyone looking to incorporate some type of gender or nontraditional power play into their sex. We'll cover: communication and negotiation anatomy (including trans bodies) strapping it on pumping oral pleasure role-playing tips, tricks and toys for hot queer sex

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Body Beautiful: Sexual Power for Different Bodies

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Almost nobody has a model's body, yet sometimes, we feel shame or guilt when our bodies don't look, act, or feel like the folks we see in the media (not to mention porn). Instead of focusing on how our bodies aren't like theirs (whether because of size, age, mobility, or strength), let's talk about how to have the best sex of our lives in the bodies that we live (and love) in. We'll cover: how we look at our bodies explore our strengths and...

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

The 5 Biggest Myths about Sex and Aging

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Joan shatters the myths and shares the most common questions that Boomers, seniors, and elders ask her. She'll answer those questions, too — in the candid, upbeat manner that led the media to dub her the "senior sexpert."

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Erotica Reading

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Come listen to erotica author and editor Rachel Kramer Bussel read from her latest anthologies, Best Women's Erotica of the Year, Volume 1.

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Bend Over Buddy

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Is your bedroom buddy just begging for some anal attention? 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...

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Blowjobs 101

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

Want to have him squirming in his seat? Our Sex Specialist will show you how to use your mouth, hands, and more to give mind-blowing blowjobs. 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.

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Open Relationships

Pleasure Chest @ 3436 N Lincoln Ave, Illinois City, IL

What are open relationships and how do they work? From polyamory and consensual non-monogamy to swinging, we'll explore how to negotiate these often challenging relationship models. Learn the pleasures and pitfalls of open relationships, improve communication and discover how to find other non-monogamous people.

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!

Unblocking Your Orgasm

Pleasure Chest @ 3023 N Broadway, Chicago, IL

This workshop is the first in a four-part series dedicated to exploring the female orgasm. We will discuss pleasure-oriented exploration, basic anatomy, breathing, and common blocks that get in the way of achieving pleasure. This class is limited to 12 attendees and requires pre-registration to guarantee a spot by emailing [email protected]. The store will be closed to create an intimate environment and safe space for discussion and...

(26) All levels 18 and older
No upcoming schedules
Free
Gift it!
Reset all filters.

No results found

Try removing some filters.

  • Price Lock Guarantee

    Secure your booking now and we'll match any price drop within 48 hours across all booking platforms, ensuring you never miss out on savings!

  • Earn 10% Reward Points

    Maximize your savings with every purchase. Unlock rewards on every transaction, ensuring you get the most value out of your experience!

  • No Added Fees

    Enjoy hassle-free transactions without worrying about additional charges. With us, what you see is what you pay - no surprises!

  • Curated Courses

    Discover a curated selection of courses handpicked by experts in the field. Dive into quality content that suits your learning needs and interests!

CourseHorse Gift Cards

  • Creative & unique gift for any occasion
  • Thousands of classes & experiences
  • No expiration date
  • Instant e-delivery (or choose a date)
  • Add a personalized message
  • Lock in a price with the Inflation Buster Gift Card Price Adjuster™
Buy a Gift Card
gift card with the CourseHorse logo gift card with the CourseHorse logo
Loading...