Q. When I was 19, I met and slept with a guy I met on the Internet. He flew out to where I lived, and we spent a week together in a hotel. Not the greatest experience, though it was consensual. Essentially, I wasn’t attracted to him in the least, but I didn’t want to enter my 20s as a virgin. Not a great reason, but it was mine. Fast forward to today. I’m a 35-year-old, 300 lb woman. I haven’t had sex or even kissed someone since that week. I’ve had lots of reasons/excuses: college and grad school, depression, no guy has given me more than a passing glance, and not really wanting to have casual sex. Not that I’m opposed to it, I just didn’t like the way I felt about myself the last time. However, I’m sick of being alone and am going to force myself out of my shell and try dating. I’m frustrated that I have essentially zero experience, and I worry that guys will expect me to have some basic level of knowledge/experience at my age. I almost think I need to go find someone to have sex with just to get over the hump and gain experience. If I do that, how do I find someone, and be safe about it? Hire a pro? Or am I just freaking myself out and guys won’t care how much experience I do or don’t have?
A. My love, I don’t believe in such a thing as a “pro.” Now, before you go thinking I’m completely off my rocker, let me clarify. I do believe in paid pros. These are the good people of the sex industry whose job it is to bring fantasy, pleasure, and comfort in whatever form they work. They are professionals, yes, but they are professionals because they have dollar signs behind what they do, and what they do? Well, what they do is always a hotbed of opinions, catapulting from extremes, from anti, to pro, often leaving out a lot of that gray middle area where the people who are actual pros don’t always get a say on where their business, personal experiences, and vast complexity meet. The dommes, the cam-girls, the porn stars, the escorts, the fetish workers? These are the people whose working experience attest to “professional.” Work. But for the rest of us (and I only mean us as a demarcation between those whose business is the sex industry and those whose business is not the sex industry), I find it hard to label anyone a “pro.” Mostly we are people skiddling around, trying to figure out what it is we want or need from sex. This goes for people with no experience, and this goes for people with years of experience.
Just a quick Google search reveals that the idea of hiring a male escort has not been yours alone. Of course, these tend to be a bit sensationalized, usually with an overarching narrative of what the author learned about themselves, while still being hush-hush on the actual nitty gritty (though Rose Russo has a great first time story) or a oh-so-silly bachelorette party vibe. However, request for male escort services are on the rise, which means that women are paying for escort services. Which means you aren’t alone.
But aside from the pro aspect of this, there is a lot going on in your question. There might be how you feel about yourself as a whole or, really, how the world at large might make you feel about yourself for not falling into acceptable boxes A and B on what women should look like. There is the idea that your future sex partners will have a required check-list of what you should be doing in bed or should know how to do. Then there is the idea that you just need to get some experience. You just need to. And maybe you need to just do this through casual sex, even if you didn’t really like the way you felt about it the time before. That then leads us to your money shot question: Should you hire a pro and how should you do it?
So let’s hash out some things.
Body Image: Let’s set one thing straight. The world is rather unforgiving to those who do not fall into those nice, neat little categories of how one should look like. Hell, we barely pretend to tolerate the ones we do accept or hold up on a pillar. By all means, and I am certain you have probably already done this, fuck those folks. Fuck people who think that there is a gatekeeper to who and who is not allowed certain experiences based off physical looks. But I do want to pose this question: How will you enjoy yourself if you allow those demons in? I don’t know if you have or have not, I don’t know if you are happy with your self now or if you aren’t. But I do know that the thing that makes any type of physical intimacy damn near impossible is that weight of negative body image.
How do you get past that? Well, that’s the trickier part. If it even applies to your current self. All I know is that if I feel shitty about my body, I don’t enjoy anything. Much less stripping down and getting down.
Checklist: I’d like to tell you that there is an acceptable checklist that everyone gets at age thirty, the one that ensures you have passed tests 1, 2, and 3, and have developed the skill set that meets requirements 4, 5, and 6, that you are proficient enough for sex.
It is not like that.
What’s better is that it differs. Wildly. Sex, more or less, doesn’t really have a standard guideline. Sure, I mean there is the insert slot A into slot B or whatever, but for the most part, sex itself will vary from person to person and how you are with person to person. What person 3 thinks is par for the course, person 9 might not even consider or care about. What someone might think totally taboo is another person’s Wednesday afternoon. That’s sort of the brilliant thing about sex — there isn’t a set guideline. There isn’t a standard how to. Sure, Cosmo might argue with me, but sex isn’t about doing it “the right way.” There isn’t one “right way.” Inexperience or not, you aren’t required to know how to do anything. The only thing that I would hope you require of yourself during sex is to do what feels good. For both of you. Which brings us to the next point.
I Need Experience: You may, you may not. But again, I don’t think you should look at it as a checklist that needs to be checked off, as if you were gathering points till you were “worthy” of being experienced enough. The need strikes me the most. Why do you need to? What about the need is so great? Why does it feel as if you are pushing yourself towards need as a must? Why do you need experience? Do you need experience because you want it? Or do you need experience because you think somewhere in the back of your brain, an ever so small thought has convinced you that if you don’t have experience, that person who has sex with you will laugh you off the block.
Think about it.
Go Pro: I love this Will Rockwell interview in Mother Jones. Rockwell, at the time a 24-year-old male escort, has this interaction with Titania Kumeh.
MJ: How do you respond to feminists who say they could never imagine any person willingly selling their body for money?
WR: It’s not selling your body, it’s more like controlled-access rental.
MJ: Does your own narrative dispel or confirm myths surrounding sex work?
WR: I’ve long since stopped trying to reconcile the disparate narratives people think about when it comes to sex workers. Victim, whore, whatever, it’s all about circumstance.
Why include this? Just to let you in on what you hopefully already know. Going pro? Is going into a business transaction, and there ain’t nothing wrong with that. But it is stigmatized. Horribly. Not only for sex workers, but for those who use sex workers’ services. Especially women. Especially women? Especially women. Go with a pro because you want to, not because you have to have experience. Go with a pro because you want a non-judgmental experience. Go with a pro to get sea legs. Don’t go with a pro because you feel you have failed some test. Don’t go with a pro because you have hit rock bottom. Don’t go with a pro because of reason x, y, and z that not only debases you, but the pro you hire.
Because at the end of the day? None of us are pros, except those who put a dollar sign after what they do (whatever that it is that they do). All of us are just muddling around through the thick of it, hoping that we figure it out. We front and puff out our chests, but sweets, we all don’t know what the hell we are doing. I promise you that. So if by going pro means you find a reputable site and hire someone to help you figure more of it out, then find a reputable website and go forth. If by going pro you mean finding out why it is you need to have sex or finding out what is it about sex you enjoy or want to enjoy, do it. If going pro means finding out what makes you sexually happy and healthy, then that is what matters, not whether or not you match the checklist of “must haves” on a sexual skill resume.
Otherwise, ain’t no such thing as a pro. Never been, never was.
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