Discover Classes. Earn Rewards.

Sex & Dating Classes Chicago

Upcoming schedule view

Learn the secrets to successful dating and navigating the modern dating scene in Chicago with Sex & Dating classes, where you can gain valuable insights and skills.

7 classes have spots left

The Ultimate O

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

The orgasms you experience with your lover start with you. Our Sex Specialists will cover anatomy, techniques for self-touch, and, of course, our favorite toys, lubes, and erotic accessories. The more you know about your own response patterns, the better your sex life will be, whether partnered or solo!

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

Suck It, Lick It, Love It

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

Our sex specialists share tips and tricks to get you in the spirit of giving and receiving amazing oral sex. We'll cover anatomy basics, giving mind-blowing blow-jobs, eating pussy like a pro, lending your mouth a hand (literally) to please your partner, and the best toys to accessorize your licks, sucks, and squeezes. We’ll be serving refreshments, so bring your partner for a pre V-Day date night!

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

Energetic Sex

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

Craving more sensation and spirituality in your lovemaking? Curious about Tantra? Then this is the class for you! You’ll learn how to activate your pelvic floor muscles to extend orgasm and increase pleasure, move sexual energy throughout your body, use breath and touch together to create fuller, deeper sensations, discover new erogenous zones and more! One lucky guest will win a copy of Urban Tantra!

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

Sex & Dating Classes 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

Queering Heterosexuality: Girlfaggery

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

In an era when the definitions of such common words as "male," "female," and "sex" are unraveling, how can we still be certain about concepts like "heterosexuality" and "homosexuality"? Janet W. Hardy, author or coauthor of eleven books about alternative sexualities (including the bestselling The Ethical Slut and her recent memoir Girlfag: A Life Told In Sex and Musicals), will explore the ways in which girlfags, guydykes, transattracted...

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

Sacred Kink: The Eightfold Paths of BDSM

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

Using BDSM and Fetishism, you may already be doing sacred kink for your own magical, emotional, spiritual and energetic work without being aware of it! Exploring the eight major routes to altered states of consciousness, we will examine how we use the Path of Ritual for earning our leathers, Path of Rhythm for cathartic flogging, Path of Flesh for sensual bondage scenes, and so much more. Come learn how to be conscious of your own sacred kink workings,...

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

Pleasure Your Vulva: For Women Only

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

The orgasms you experience with your lover start with you. Our Sex Specialists will cover anatomy, techniques for self-touch, and, of course, our favorite toys, lubes, and erotic accessories. The more you know about your own response patterns, the better your sex life will be, whether partnered or solo! This workshop will be a safe space for women & trans* identified people only.

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

G-spot and Female Ejaculation

Pleasure Chest

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!

(26) All levels 18 and older
No upcoming schedules

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!

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!
Reset all filters.

No results found

Try removing some filters.

Sex & Dating Classes in Chicago are rated 4.3 stars based on 26 verified reviews from actual CourseHorse.com purchasers.

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...