When I befriended Sherif back in 2019, we instantly bonded over our shared love of old people. Both of our oldest lovers at the time happened to be 69. As such, it came as no surprise to me when he mentioned having lost his virginity as a teenager to a woman in her thirties, clearly asserting that he had been the one who had initiated the exchange.

I didn’t pry and went on with my life, assuming that the older woman in question had been a teacher at his boarding school or a friend’s bored housewife of a mom. Flash forward three years and I finally got the real story. Turns out, his v card was swiped by an escort in a hilarious coming of age tale, which has become a bit in his standup comedy routine. I hope the transcript does it justice: 

Jules: So tell me about your first sexual experience. 

Sherif: It’s kind of a bizarre story. I was sleeping over at a friend’s house and his parents were driving his younger brother to a hockey tournament out of state. It was a group of young men. I was 14 years old at the time and my friends started looking at the newspaper and found that there were escort services being advertised.

They were really into this idea of ordering escorts to the house. I don’t think I stopped to think about it much before it happened. They started making phone calls and asking questions to some of the various services. I remember having no idea what was going on. I guess I was, in some ways, one of the more naive of the group, but I remember they were only calling ads that had full service in the classification, which I guess insinuated that full sex was on the table. 

And just to give you some contextualization of how old we were, my friends and I had been at the arcade the night before. There were probably like five of us and we ordered two people over and initially I was not planning on being one of the ones to do the deed. I remember it being extremely exciting. Waiting for them to arrive felt like an eternity. 

Then all of a sudden there’s a black car pulled into the driveway and out comes my friend’s aunt. She came in and she was like, “Hi boys. I’m just checking in on you guys. How are you doing?” Meanwhile, the escorts are on the way over to the house. One kid saw the aunt’s face and he ran out of the yard, hopped the fence and ran all the way home because he was not trying to be there for any dramatic confrontations.

So anyway, my friend’s aunt must have been getting the most frantic “Everything’s fine! Get the hell out of here.” energy. We were really nervous but luckily she did leave before they arrived. That would have been a crazy situation to have to endure and witness. A little while later, another car pulled up and these two women came out of the vehicle.

One of my friends had ordered the escorts so it was going to be him and another guy. But after taking one look at the escorts, who were a little overweight, the other friend was like, “Nah I’m not doing this,” so then I was like: “I’ll do it.” I found them very attractive. They were probably like 38 years old or something. And I was 14 at the time. So it was a drastic age difference. I’m sure they were not super pleased to see that. But I was like “Ya, it’s me,” and one of the ladies led me to the bedroom. I was only like 5 seconds behind her but by the time I entered the room, she had already taken off all her clothes. She put a condom on me and started giving me fellatio…is that the proper word for it?

Jules: Ya it is. And oh my god! Just like that? There was no discussion about age whatsoever? I mean even now, as a 33 year old, you look young.

Sherif: No, she did not have any concerns about my age. At least none that were outwardly expressed. I’m sure to some degree she already viewed her profession as illegal. It was also very clear what was going on. 

Jules: So no one was confused or unwilling? 

Sherif: Exactly. After receiving fellatio for some time, I was like, “All right, let’s have sex.” And then I entered her and it lasted maybe three seconds. It was so fast…like unbelievably fast. And she was like “all right,” and she got up and was ready to be done. 

The whole encounter had taken a minute or two tops, probably not even that. And I remember being like, “Uh, I’ve got a little bit more left in me,” and she didn’t give a shit. She just put her clothes back on and then left the room. And then she went into the other room where my other friend was with his escort and she was like: “Hey, do you guys need any help in here?”

And my friend was like “yeah.” So she  goes in and I remember thinking: “Where’s all the other guys?” And it turns out that they had gone outside and were watching our other friend through the window. This whole story is really uncomfortable and doesn’t really stand the test of time really well, but that’s how it happened.

When the escorts left, we were really careful about the disposal of the condoms. We tied them up and put them in paper towels before tossing them. Afterwards, we took our Razor scooters to the library to hang out. Then my friend receives a call from his dad and his dad is screaming on the phone: “I want to know what the hell went on when we were gone? What the fuck was going on here?” And we were so scared when we heard this but apparently there was just a leaky toilet we had flushed and the leak had gotten down into the basement and the water had damaged some of his work papers, and that’s why he was angry. 

Jules: Wow. Talking about a coming of age tale. Looking back at this whole experience now, do you feel like you were violated? A 14 year old in the U.S is not legally an adult. So technically, even if you thought you wanted it, you were not consenting. You were a child. 

Sherif: As a 33 year old, it’s not a very romantic story. I don’t think it was very romantic as a 14 year old either. I certainly did not feel violated though. I was very happy. For the longest time before that I had just been this excruciatingly horny teenage boy and so I found it to be a great source of relief. Honestly, if there are any victims in this story, I believe it to be the escort. She probably did technically statutorily rape me but she was absolutely the victim of circumstance and I do not feel like I was the victim in any way.

I kind of feel bad that she had to have sex with me and I don’t feel great about the whole frat boy vibe surrounding the story. It doesn’t feel great to reflect upon this story at all. I do think it’s kind of this wild story but it’s definitely not one that I’m proud of. With that said, it’s not something that I feel like has negatively impacted me. It’s just kind of informed the way I think about certain issues.

Jules: Cool, cool, and what came first – the chicken or the egg? As in, did you have a Mrs. Robinson fetish before, or do you think that this experience made you more attracted to older women?

Sherif: I had one before that. I never look at porn now and I don’t know why it’s important for me to emphasize that, but I definitely was looking at pornography with older ladies, not younger ladies back then.

Jules: What’s your opinion about sex work in general?

Sherif: I think sex work is a more complicated issue than it’s often credited with being. A lot of people say, “Oh, it’s horrible because people are selling their bodies,” but hard laborers sell their bodies too. But when construction workers suffer physical injuries on the job, they don’t face the same stigma for selling their bodies that sex workers do. 

I do think that in this society, women have been objectified to a degree that they’re being valued for their looks and appearance, but there’s undoubtedly a sexual power that women have. And with certain ways that they’ve been able to monetize it, it’s been interesting. But I also think it’s very important to draw a line between sex work and trafficking and to acknowledge that trafficking is not the only way that people get coerced into forms of sex work. So it’s kind of a blurry line for me and I’m not entirely sure where I stand on it. 

I think websites like Only Fans have been really, really liberating for lots of women. There’s people making hundreds of thousands of dollars just selling pictures of their feet online, which enables them to enjoy a certain kind of lifestyle and provides way more flexibility than other jobs. It can easily become a full-time job though. You have to engage with your clients and market yourself. You have to be taking photos all the time. It’s not easy work, even though it might be far less strenuous than other forms of labor in certain contexts.

I’ve also dated a sex worker before who was seeing a regular roster of clients. She really enjoyed the work and had the luxury of being very selective about who she saw. But there was something about the work that was not entirely wholesome on an energetic level. Like every form of labor, sex work has it’s trade-offs, and like I said before, it’s a far more complex issue than either pro or anti stance gives voice to. 

Jules: I totally agree with that. In my own sex work journey, it’s been important for me to separate morality from spirituality. The Judaeo-Christian patriarchy we live in basically ascribes moral judgment – good or bad – to everything we say and do, which in turn, perpetuates shame culture. I have no moral hang ups about my time as a sugar baby, but I totally get where you’re coming from with the whole energy exchange thing. 

As I’ve gotten older, I find myself seeking more spiritually connected sexual experiences. I have no regrets about all the casual sex I’ve had (and might have again at some point in my life), but for now sex work doesn’t really do it for me. So tell me, was this teenage adventure your one and only encounter with a sex worker?

Sherif: I’ve had two other experiences with sex workers, which were drastically different. One time I met a lady online who I was talking to and we were really hitting it off. I was being super, super funny and towards the end she was like, ”By the way, like I’m a professional,” and I was like, “professional, what?” And she was like, “Well you know, I do this for a living.”

So I was like, “Oh shit, that’s a deal breaker for me.” I was not into that at all. I’ve still never paid for sex. That first time, my friend paid for it because he was supposed to go and he had already committed so I ended up not having to pay. 

So anyways, this lady was like, “That’s okay,” and we ended up meeting anyways. She understood that I was not trying to pay. We met at a short-stay motel where she had to leave a $50 deposit. And we went into the room and I ended up smoking her son’s weed. This was some Mrs. Robinson vibes for sure. 

Jules: How old were you and how old was she?

Sherif:  I was probably like 19 and I don’t know about her, but she was definitely a woman. She had a 15 or 16 year old son and she looked like the therapist from the Sopranos.

Jules: Ooh hot! That’s like your favorite show, right?

Sherif: Yeah, I loved that show. I remember at one point she took her glasses off and I told her to put them back on. I don’t know why I needed to include that detail but I feel strongly about it being printed. Then when we were leaving, she said that she was embarrassed to go pick up the $50 deposit from the front desk. So I said I would go pick it up, and she was like, “I’ll tip my boy toy.” So I went and picked up the $50 deposit. This is a story I tell very proudly because I got paid to have sex with a sex worker, which I thought was a unique turn of events.

My other encounter was with this creepy pervert I met online. I ended up talking to this guy who said that he wanted to watch me have sex with someone that he hired. I was like, “Uhh this is sketchy,” but I was at a really low point in my life, so I agreed to meet up. 

Jules: What do you mean you met him online?? What forum was this? 

Sherif: Craigslist. It was in the middle of the “Men Looking for Women” ads and he didn’t pose as a woman or anything but he kept the whole thing vague at first. He basically was this really rich guy who went around and got me food and stuff and then we rented this really nice suite.

Jules: Was he cute?

Sherif: No. I don’t think he was particularly good looking or ugly. So this lady shows up after this other lady had gotten into a fight with the guy and left. It was this whole thing. At one point he asked me if I would ejaculate in his face and I was, “no, I wouldn’t.” So then he has this other guy come and tells me, “You gotta get out of here,” and then this other, much hotter lady shows up. So I start making out with her and he goes, “Hey, hey! This is not for you” and then I just left and that was it. 

Jules: Wow what a trip! I appreciate the perspective you bring to the table. From being the client to dating a sex worker and kind-of-sort-of even dabbling in sex work by accident, you make a great storyteller! 

Sherif: Thanks for the opportunity to share my stories. 

Sex Work



Based in Brooklyn, Jules has dedicated her twenties towards harnessing her pussy power, exploring the muse, whore, and wild woman archetypes along the way. When not blogging, you can find her sweating the toxins out in a hot yoga class or sipping a matcha latte at a pretentious coffee shop, whilst she scribbles away in her journal.

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