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Mom Talk: I Paid for An Orgasm

Written by Anna Diaz

Photography by Photograph Courtesy of Land of Women

For this week’s Mom Talk, writer and mom Anna Diaz gets deeply personal, opening up about how she researched and eventually ended up paying for a sensual massage—yep, pretty much a “happy ending”-type situation. But beyond the fascinating details of the session itself, it’s the self-realization that the intimate experience inspired in her that proved to be truly life changing. 

I’m a writer. I like searching out intriguing stories and following the rabbit hole of discovery. I am also a woman with a strong sex drive, and I had always had a particular fantasy about a massage turning into something more.

A few years ago, I stumbled upon an article about a man in New York City who offered highly intimate massages, resulting in dozens of satisfied women. The quotes he listed from women seemed real. The process appeared to be selective. Up until this moment, I had no idea this service actually existed for women, and I instantly felt envious of the women in New York—it was something I needed to have.

I was in a long-term, monogamous, and very committed relationship. We had a one-year-old. Often, our child would sleep in our bed. We still found time for sex, occasionally, but it wasn’t truly fulfilling for either of us. I remember thinking that there was something missing—the feeling of passionate love, taking the time to slow down and be present, the focus on satisfying the other person rather than a quick get off. It was all fast and routine. It felt like a checklist of actions, and then we were done. It was our young and inexperienced fault, we never actually talked about our sexual needs and desires when we started our relationship. I was highly sexual, but I wasn’t actually comfortable talking about what I wanted. I owned a perceived sexual power, but I still didn’t understand my body enough to know what would bring me to orgasm with a partner. I had past trauma that I had never worked through. And we never spent the time to build an intimate connection, exploration, and compassionate understanding.

So, here I was fantasizing about a random man in New York and the services he could provide for a few hundred dollars. I felt guilty. Again, I’m a mom with a partner. Is this cheating? Prostitution? Just a fantasy? But still I was intrigued and genuinely curious. The journalist in me kicked in. I went on a hunt. I lived in San Francisco, one of the most sex-positive cities in the world. This had to exist here. Who are these men who provide this? What kind of women do they see? What actually happens? Are there neon lights? I finally, hesitatingly searched Craigslist and found a posting under the search words “sensual massage.” This guy had a website with approachable copy and nice photos of himself. He was attractive. He seemed charming but in a trustworthy kind of way. I instantly used my internet research tools learned from MTV’s Catfish and image searched his photos to see if he was legit. I found his LinkedIn profile, old blogs, and more. He was a real person, with a secret job on the side pleasuring women. I couldn’t actually commit to seeing him as a paying customer, but I figured I could get a fascinating story out of this discovery. I immediately messaged him and said that I’d like to interview him. I wanted to understand more about the women who made appointments; who they were and what they hoped to get. Were they married or single, older or younger, sex-positive or timid? I also wanted to know more about him. How did he get started? Why? Subconsciously I wanted to discover answers for myself, too; like would I actually do it?

We met for coffee a few days later. He brought his dog to the café. We talked for an hour and he answered my dozen questions. At this point, I was in full-on research mode and my fantasy had receded. I learned that most of his customers were either in sexless marriages, divorced, or widowed. Some were single and career-focused. Some had suffered sexual trauma. But all were looking for affection and intimacy; not orgasms.

I can’t quite recall what made me do it. Maybe it was his sincerity and genuine interest in women deserving pleasure. But I made an appointment for myself.

In the days leading up, I was anxious. I was excited. And I was nervous. I considered canceling. But instead I took an early lunch from work to make my 11 a.m. appointment. I fully expected to go back to work afterwards, as well, like I had just hit the gym for an hour. When I arrived at his place, he greeted me with a smile and a hug. Usually his clients are completely anonymous, screened only by a phone call, but we had already met in person and talked for an hour. Plus, I internet stalked him. I felt like I knew and trusted him.

We sat down on his leather sofa and talked. He brought me chamomile tea. He wanted to discuss why I was there, what my expectations were, and if I had boundaries. This was the first time I had ever talked so openly about my sexual expectations and boundaries with a man. It’s the first time anyone asked. Already it didn’t feel the same way it did with my partner, not in some small part because I was paying him. I felt like I could be honest and open without him judging me. He was there to listen and provide a service.

The lights were low, spa music was on, and the room was warm. I laid down on the massage table, completely covered by a sheet. It started like any normal massage—upper back, stretching, oil. I tried to focus on me, but all I could think about was work, my family, and the mental load of life.

The massage took a gradual turn from a typical massage to a slow and sensual one without me noticing. I was relaxed and the nervousness gave way to physical pleasure. For an hour and a half, his hands were completely focused on my body. They responded to my breathing. I had multiple orgasms. My body felt things I had never felt before. And I couldn’t touch him. That was the hardest part. I had to focus only on myself and the new things I was feeling.

I think as women, we’ve been programmed to believe that if we receive pleasure, we have to return the favor. For me, not doing this completely shifted something inside of me. I had a startling moment of empowerment, somewhere in between orgasms, where I realized I was deserving of good things. I was deserving of love and respect. It was delivered under the guise of sensual pleasure. But still it was the same. I deserved to be seen, to be respected, to be loved. I deserved orgasms. But ultimately, I was simply deserving. I felt empowered and incredibly sad at the same time.

He whispered that we had five minutes left, caressed my head, and led me in deep breathing. I showered and met him back on the same leather sofa to talk about my experience. I can’t remember what I said. But I knew that my life had just changed. I couldn’t believe it took me that long in life to feel and truly believe that I was deserving of good things; not good things for my family, not for my parents, not for my partner; but for me. I deserved it. And, it came from paying a man I met on the internet for a sensual massage. But why didn’t I feel this way with my partner? Why had I never felt this way before? That was the next reality I had to face.

I did some intense personal work immediately after. I read books. I saw a therapist. I asked myself the hard questions, and I realized I was deeply unhappy. A month or so after my massage, I had the difficult conversation with my partner that I wasn’t happy. I didn’t feel seen or respected. We tried to make it work, but a few months later we began the transition to end our relationship. I’ve been single for about three years. We’re co-parenting wonderfully and great friends. I’ve just recently started dating again, and I’m going in fully aware of my needs and having done the self-work. I also know that I’m not interested in casual sex without a connection.

I learned from this experience that one of the most important aspects to building an intimate relationship with someone is creating a safe space; physically and emotionally. It’s not OK to be in a relationship where you’re not getting those needs met. But it takes communication and trust to get there. If your partner isn’t willing to have those conversations, that’s a problem. Now that I feel comfortable talking to my friends about my experience, I realize I’m not alone. “Happy ending massage” seems to be one of the most popular porn searches for women. Apparently, a large majority of women fantasize about a slow, sensual touch that ends in an orgasmic experience. Do you think that says something about what we’re missing in our sex lives?

For me (and so many other women), it took paying for a sensual massage to finally believe that we’re all truly deserving of more than the status quo—in and out of bed.

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