What I Learned About Shame From Dating A Sex Teacher

sexy teacher holds class's attention

Nine years ago, I was coming out of a marriage and looking to spread my wings. I knew sex advice and sex teacher Sheri Winston slightly and resolved to ask her out. I was attracted to her and I was also intrigued—I wanted to find out what it was like to have sex with a sex teacher.

At a Halloween party, I took the plunge and propositioned her. I was in drag, wearing a short, silver lamé dress. Sheri was a slutty fairy—my attention was divided between her pointy ears, big smile and massive cleavage. She countered my proposal with: “Let’s have dinner and see how things go”.

A week later, when the date happened, I figured that if at some point we did end up in bed together, Sheri would likely give me a mediocre grade. After all, I was just a regular guy, not a sex teacher or Tantra guru. I figured, at the least, I could put a check mark on my bucket list next to ‘sleep with sex teacher,’ and she and I would just go our separate ways. Only, the opposite happened. We kissed. We looked at each other (what was that?), and we’ve been together as a couple ever since.

It hasn’t always been easy. Relationships by nature are tricky, but when you put two strong-willed people together not all the sparks are sexual. But we’re still together happily and overall we’ve thrived. I even joined the fascinating world of sex teachers and sex activists—I call it ‘Sex World.’ I was there with Sheri when she was awarded a national prize for her first book, Women’s Anatomy of Arousal. I’ve even switched careers to being a full-time sex and relationships writer, recently assisting Sheri with her new book Succulent SexCraft: Your Hands-On Guide to Erotic Play & Practice, which is a guide to having the best sex ever.

So what have I learned in all of this time living with a sex teacher?

The most important thing is that, in order to truly take your sex life to a new level, you have to embrace one thing — being shameless.

Sheri is what’s known as a “big beautiful woman.” In our culture, people with her body type are often shamed and become riddled with body-image issues. But I’ve learned that shame shouldn’t stop or hinder them (or anyone one with any body type, for that matter). Sheri has a fabulous sex life—and that’s not on account of me, it’s because of her and her shameless attitude toward enjoying her body and pleasure. She was even featured on the television show The Doctors as “the most orgasmic woman in the world.” So clearly, Sheri’s body shape isn’t keeping her from having an over-the-top great sex life.

And it is this confidence and unapologetic shameless that attracted me to her initially. I admire that. And adore her smile. And appreciate her ease with all things sexy. She’s a role model for everyone with body-image issues and a champion for embracing your erotic birthright. She is shameless in the best sense of the word.

So, how do YOU become sexually shameless?

Focus On Your Pleasure
Savor all of the wonderful sensations and experiences you get by having a human body. Sheri didn’t start off shameless. She learned it. You can, too.

Replace Negative Thought Tapes
It’s time to kick those toxic thoughts out of your head and replace them with positive ones. In Succulent SexCraft, Sheri suggests that you notice and replace every self-negative thought with three positive ones. She also proposes activities like ‘mirror work.’ “There are innumerable ways to do mirror work,” she writes. “There is only one rule—no negativity allowed! Look into your own eyes. Whisper sweet somethings to yourself. Send yourself love, admiration, appreciation and more love.”

Or, if that seems too intimate or awkward initially, take that self-love-fest to paper. Sheri suggests: “Write down everything about yourself that’s wonderful, positive and lovable. Keep adding to the list! Put it on your altar or refrigerator and refer to it when feeling less than fabulous about yourself.”

Cultivate Shame Resilience
Almost everyone feels sexual shame at some point, not because we’ve done something wrong but for reasons involving low self-esteem (“I’m not doing it right,” “My body’s gross,” etc.).

While we can’t keep these feelings from happening, we can learn to keep them from triggering or derailing us. We do this by noticing the shame and then using various mind-body techniques to release it, such as breathing it away or replacing the triggering stories with positive ones.

If negative thoughts or feelings get intense while having partner sex, call a halt to the action and, if you’re comfortable with your partner, share what’s coming up for you. The biggest challenge with shame is that we’re ashamed to talk about it. Naming it aloud can take shame's sting away.

An Invitation To Let Go Of Sexual Shame Forever
Sheri’s tongue-in-cheek mission is to ‘save the world, one orgasm at a time.’ Imagine a planet where everyone has a healthy, responsible relationship with their sexuality and can easily get wildly ecstatic. It would be a happier place: there would be much less suffering. I"m delighted to be living with and partering in business with a sex teacher who is committed to helping create this positive future. During my time with her, I’ve learned that:

  • Our sexual potential as human beings is amazing. Miraculous, even.
  • It’s not about the body. (Be shameless—get out of your own way!)
  • Yet it also is about the body (without the body, we'd have no pleasure). And it's also about the mind. And the heart. And the spirit. 

Pleasure is our birthright. Shamelessness is the first step to claiming it. The second step? Learning to play our instrument skillfully. Like playing tennis or the piano, sex is something we can all get better at. We do so by developing our 'sexcraft' skills, by learning how to ramp up our body, mind, heart and spirit to a level of arousal that goes far beyond what most people are aware exists. Sheri knows how to do this: it's why she was invited on The Doctors.

Anyone can do this. You just need to know how.

Like love, like life, sex is a learning journey. For Sheri and me, it’s nine years later, we’re still learning—and I’m just loving the journey.

If you’d like to learn more about reclaiming your erotic birthright join Sheri and me for the celebration (and special promotion) of the launch of her latest book Succulent SexCraft: Your Hands-On Guide to Erotic Play & Practice. Buy the book September 14-16 and gain access to a collection of great free resources (valued at well over $1,000) from over 20 of our favorite fellow sex, relationship, and empowerment teachers.