I frequent several online forums that encourage members of the public to ask questions of sex workers. At least once a week someone, usually a young man, asks about seeing a sex worker to “lose their virginity.”
Virginity is an abstract concept, not something one can misplace, but it is a powerful one that carries emotional and social baggage. While I don’t prefer the phrase “losing your virginity” it is a popular colloquialism so I’ll be using it in this article. If you like, you can instead read it as “having sex for the first time” or “trying something new.”
Disclaimer: Losing your virginity to an escort is not for everyone. There will be condoms involved which can sometimes be awkward and do change the quality of sensation. If you find someone compassionate and thoughtful, it can be a great way to explore this activity that our society craves and also fears. If you wind up seeing someone with little investment in your learning and growth, it can be lackluster and possibly reinforce negative internal and external messaging. Seeing a sex worker also carries heavy stigma and may not be something you will ever be able to share in the future. Only you can decide if losing your virginity to an escort is right for you. Because these encounters aren’t spontaneous and perfectly organic, you are unlikely to forget it. Don’t be afraid to take your time deciding, or to change your mind.
Disclaimer two: This article is aimed as heterosexual men who want to learn how to sexually pleasure heterosexual women. Much of what I have to teach can be applied across gender and orientation boundaries and I welcome folx from across the gender and orientation spectrum. I will say that due to class and sex dynamics in the sex industry, my experience is less broad outside of cis/het men. People outside the cis/het/male box have as much to teach me as I have to teach you.
I love the expression “sex is like money: the less you have, the more you worry about it.” Sex lives at a major crossroads. Love, pleasure, physical touch, societal expectations, gender, orientation, identity, family ties… People may feel trepidation, excitement, fear, joy, worry, curiosity, and a range of other emotions, based on their previous experiences with their bodies both sexually and otherwise, and their feeling for, towards, and around the person they’re about to have sex with. We are confronted with sexualized images of men and women every day, selling us products to look better, smell better, fuck better, be loved better, work better, and in every case we are sold stories about how men are supposed to be. How women are supposed to be. And how men and women are supposed to be together. If you haven’t had sex yet, this ocean of imagery can be a painful and constant reminder of that fact, carrying the implication of deficiency, as well as images of a heteronormative future that you may or may not want.
Sex can be great. It should feel good, it can be a way to connect with someone you care about or a way to enjoy pleasure with someone you may not know again tomorrow. It is also highly charged and rarely talked about candidly. For young men, the pressure to perform properly the first time can be immense. In some cases, that pressure prevents people from seizing opportunities and if that happens often enough, you may start to feel behind the curve. Not just a late bloomer but inexperienced. You may begin to worry that when you do finally find a girlfriend, you won’t know how to please her. Shame may lead to fear, fear may lead to avoidance, and while I am a huge fan of doing things on your own time scale, we do not exist in a vacuum and societal pressures may worsen as time goes on.
Thats a lot of pressure to put on something that often lasts about three minutes.
The first time I had sex, it was wonderful. I am a sexual person, deeply physical, and our respective religious upbringings made each step forward excruciatingly slow. Kissing took weeks to work up to. Months later we were down to underwear. The afternoon we first had sex, we had kissed and hugged and inched closer for something like an hour. The anticipation had us both so aroused that actual penetration was effortless. All thirty five seconds of it.
While it was not enough for me to orgasm, the sensation of wanting to feel a penis inside my vagina and then finally getting it was incredibly satisfying. I *still* love that feeling. Unfortunately I didn’t have the vocabulary or the sense of self to say that and instead, I lied. I sad that I had come many times and for the next two years I lived with that lie. We never developed a mutually satisfying, healthy sexual relationship and it took me years of working with more mature, giving partners to come into my own. I sometimes wish I had been able to give him real feedback. I hope his wife is happy and has been able to mend some of the bad habits I never had the courage to confront.
It’s been fifteen years since that day. I have developed (and continue to strengthen) my ability to advocate for myself and offer constructive feedback. With my training in full body touch and my experience helping people slow down, I am finally ready to offer what I was unable to give my high school boyfriend. I didn’t tell him that his kisses were too big and too wet. I didn’t tell him that he needed to let me touch myself during sex if he wanted me to orgasm. I didn’t tell him that I wanted to try new positions or new things. I didn’t even know I wanted him to go down on me, much less tell him how to do it.
But I can tell you. If you’re ready to hear it.
Coaching sessions aren’t reserved for virgins, but recipients are best served when they come with open minds and are ready to rebuild from the ground up. Much of what I will teach you isn’t sexual. While many women are just as horny as men are assumed to be, *in general* women also need safety and time from you before they will have a fulfilling sexual encounter. I’m not a pickup artist. I’m not interested in teaching you how to trick women into bed or how to bed as many women as possible. I am not responsible for getting women into bed with you. What I *can* do is help you get them in bed more than once.
As your sex coach, I will teach you:
-Recognizing and confirming nonverbal cues
-Escalating touch
-Critical moments in sexual progression
-Establishing initial and ongoing consent (without breaking the mood)
-Giving verbal and nonverbal safety cues
-Reading body language during foreplay
-Recognizing the right moment for penetration
-Specific sexual positions to suit your body
-Aftercare
Incorporated throughout:
-Dirty talk
-Safer sex practices
-Kink awareness
-Tips and techniques to try out
-Self care and preparation
-Grooming
And whatever else pops up during our time together.
I love to give back. I have had so many solicitous, caring, encouraging clients (and a few notable boyfriends) share their experiences, stories, and cocks with me. I have learned a tremendous amount about sexuality, sex, how to do it well, how to take care of your partner, and how to advocate for yourself. It’s time for me to offer these skills in return to the next crop of eager, possibly a little nervous, young men.
Sessions are not discounted. This coaching is hands on and a branch of the work I already do. I won’t do a coaching session shorter than two hours and it is strongly suggested you plan on several sessions not more than a month apart.
At this time I will not be seeing couples or women *for coaching*. Womxn are still encouraged to come in for nourishing bodywork and enjoy 50% off on their first two sessions. Couples are welcome to book a minimum two hour session for regular intimate companionship and are not currently subject to an additional fee. My practice is growing but for now I’m sticking to what I feel most at home with.
My gratitude for those who shared their wisdom, my excitement for those with wisdom in their future, and my pleasure for all good people, wherever you are.