10 Things I Could Do If I Hired a Male Escort

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I thought a lot about male escorts when I was younger, because the thought of sex with men worried me and I wanted someone to shepherd me through it non-judgmentally. I wanted to be taught tricks and strategies, and to thereby embolden me for future (non-transactional) sexual encounters with men. When young male virgins write to me now to ask for advice on building sexual confidence and “getting into the game,” I’m being very serious when I suggest they see a sex worker – because I strongly considered taking this route myself. head harness ball gag

However, I ultimately decided not to, because 1) I didn’t have enough money, 2) I was scared, and 3) I fell in love with a man who was just as patient and kind about my sexual inexperience as I had hoped an escort would be. BUT. Even still today, I think about hiring sex workers every once in a while, as an indulgence if some extra dough ever fell into my lap. Being demisexual, however, I don’t think I would employ them for sex – and some escort agencies explicitly say that their workers don’t even offer sex. So here are 10 other things I might consider doing if I hired a male escort…

1. Massage. Yeah, I should really just hire a masseuse if this is what I’m after, but there is something different about a massage that is allowed to be flirty or even sexy. It has a different energy and I’m able to relax into it in a different way. Sometimes it’s nice to be touched in a way that is sex-adjacent but not explicitly sexual, y’know?

2. Masochism. As a masochistic submissive, I crave pain and subspace almost as often as I crave sex. But unlike pleasure and orgasms, good pain isn’t easy to administer to myself. Outsourcing the task would be better, especially if I found an escort who was experienced in whatever activity I was craving (let’s be honest – probably spanking).

3. Topping practice. Granted, I would imagine submissive male escorts are harder to find than dominant ones (correct me if I’m wrong), but I think some “hired help” could allow me to hone my topping skills, like impact play, face-slapping, and even just dominant dirty talk. It’s less embarrassing to practice on someone who does this stuff all the time than on someone who could literally break up with you if you mess something up.

4. Vacation accomplice. A while ago I was invited on a press trip to an all-inclusive swingers’ resort, and I had to decline, partly because of scheduling issues but also partly because my partner wasn’t available to accompany me and I would’ve been in social anxiety hell if I went alone. It’s a pipe dream that I’d ever have enough cash to splurge on a whole weekend or week of an escort’s time, but in a dream world where I do, they’d be a good date to a getaway.

5. Flirting. So underrated and so important! Sometimes – especially when you’re single and/or lonely – you just need somebody to make you feel wanted and wantable. I could see hiring an escort for a fun dinner-and-drinks date for the express purpose of being flirted with. Mmm, crushy energy.

6. Cuddles. Some studies show human touch is actually necessary for our well-being, and I believe it. It would be nice to hire a professional cuddler in the midst of a particularly lonely dry spell, or to comfort me at the end of a hard day.

7. Wedding guest. Weddings suck if you’re sad about your romantic life. I have definitely cried at them for totally self-absorbed reasons as well as the normal reasons people cry at weddings. I could imagine hiring an escort to be my +1 if my originally-planned date dropped out for some reason (like a breakup) and I didn’t want to go alone.

8. Photos and videos. Provided the escort was okay with it, it might be fun in an artistic-collaboration way if we shot some sexy pictures or clips together, either to sell (with profit-sharing, of course!) or just for personal perusal. Seeing myself from different perspectives is sometimes a good way to boost my self-esteem when I need it, and “entwined in intimate embrace with a hot escort” is certainly a different perspective!

9. Tourism. When you visit a new city, your experience of it is vastly influenced by the person or people who show you around. My Toronto is different from a Bay Street banker’s Toronto or a hippie artist’s Toronto, for example. It would be neat to hire an escort while visiting a new place, and have them lead me around to some of their favorite spots.

10. Learning. I have known enough escorts to know that they have skillsets almost nobody else has. They have to have above-average emotional and social intelligence, in addition to whatever sex and kink skills they may use in their line of work. I find that inspirational and could put similar skills to use in many areas of my life, so it would be cool to get some one-on-one tutelage from a willing escort on these topics.

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