I gave happy-ending massages to women—for a year
Seven lessons from a year of erotic touch
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In 2014, I found myself broke, burned out, and unable to get hired because of the things I talked about online—sex, love, intimacy.
Then, a friend joked, “Maybe you should be an escort.” I laughed. And then I didn’t.
This is the true story of what happened next—and what I learned about giving erotic massages to women in San Francisco.
After years of driving a taxi in San Francisco, it was time for something new. Living in the Bay Area was fun but expensive. I saw all my friends with high-paying tech jobs and longed for that stability.
However, after a few interviews, I encountered a snag: some companies felt I was too risky to hire.
My years of writing blog posts on sex and love and the videos I posted on YouTube talking to my passengers about corporately unmentionable topics made it so that most tech companies didn’t want to hire me. I was “high-risk.” One company went so far as to say they thought I might hit on their employees and clients.
So, I found myself at a crossroads.
Do I whitewash my online persona to make myself employable, or do I go “all in” into the world of sex, love, and dating and see what happens?
The fact that you’re reading this is foreshadowing enough for you, I’m sure.
After being told I was “unemployable” by a tech company, a friend joked I should become a male escort. I laughed it off, but then started to wonder: what would giving pleasure to women look like?
So, I started doing some research and came across an HBO show called Hung, about a struggling dad who turns to prostitution.
The idea of spending my night at high-end hotel bars cruising for rich, single women didn’t appeal to me, and didn’t feel like the best use of my time. There had to be a better way.
At the time, I hung out with a very sex positive, queer, crowd. Come to think of it, I still do. A few of my female friends were sex workers and gave happy ending massages to male clients. Was there a market for female clients?
Would I want to do that? It sounded exciting, fun, and an excellent way to pay the bills.
Would women want that kind of treatment? Why wasn’t there more demand for this? You can find female providers easily just about anywhere, but are women looking for no-strings-attached sexual pleasure?
I guess there was only one way to find out.
I got a table on Craigslist, had my friends show me the mechanics of a happy-ending massage, and went to a weekend workshop at Esalen to learn their basic moves.
Then, I built a simple website with testimonials and advertised on Craigslist’s “casual encounters” personals section. I called myself Mister Sean, to, you know, throw off the authorities.
Close your eyes. Turn off your mind.
Relax into my strong hands and feel your stresses melt away.
Open your body and should to a new kind of experience.
Stop it. You can’t make up this stuff up. This is the real deal landing page copy I created for this service!
Slowly but surely, I started getting clients—not a ton at first, but enough to stay busy and start making a decent living. Some of those clients came back or told their friends. A few months into it, I was booked solid.
Along the way, I started seeing patterns. I figured out what worked and didn’t work to make my clients feel safe and open.
Here are a few of the most surprising things I learned.
1. The setting matters
I converted my living room into a massage studio and ensured it was clean, tidy, and warm.
Environment and setting can play a significant role in arousal. If my clients didn’t feel relaxed, they’d have difficulty letting go and surrendering to my touch.
Dim lighting, blackout curtains, and candles transformed the massage space.
Palo Santo, an earthy, sweet-smelling incense stick, gave the space a subtle and inviting fragrance. Sometimes, I spritzed the sheets with a little lavender water; a nice soothing touch.
I’d round out the package by playing a gentle massage mix. This one was my favorite:
2. Transparency equals safety
When welcoming my clients into the massage space, we’d sit on the couch and connect for a few minutes. I’d offer them chamomile tea to help them ground, even though a few requested something a little stronger. A shot of whiskey before your massage, perhaps?!
I asked them what they hoped to get from the experience, what prompted them to contact me, and if they had any questions.
Then I’d share a bit about what I offered—my “modalities,” if you will.
I told them that I would only massage them with my hands—no penetration, no oral, no sex.
I shared that I’d check in to ensure they were comfortable and encouraged them to speak up if they wanted direction.
The more they knew, the more they surrendered to the experience. And the more they could surrender, the more they could open up.
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