September 22, 2015

You Want Me To What? 21 Sex Workers Describe Their Weirdest Client Requests

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via Shutterstock
via Shutterstock

1. “He wanted me to put a plug up his butt and call him every hour at his office to make sure he still had it in. I did this for an entire week, only letting him take it out to use the bathroom and go to sleep. I actually enjoyed the power play of it way more than I thought I would.”

—Emily, 27

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2. “One guy asked to call me ‘mother’ the whole time we were having sex. Keep in mind, variations of this are pretty common stuff but I’d never had anyone want to matter of factly call me ‘mother’ like he was an English butler giving instructions on cleaning the mansion. It actually seemed weirder to me than a guy begging for a dildo ramming while calling out ‘mommy’.”

—Tammy, 23

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3. “Testicle slapping. I’ve had several clients request this but the first one had injected saline into his scrotum so that it was enormous. He wanted them smacked until they were red and hot. The guy came three times that way. It was actually kind of impressive.”

—Brianna, 30

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4. “I had a client that wanted me to tell him about how I lost my virginity during foreplay. Considering I lost mine the way most people do, in an awkward fumbling session that’s completely forgettable, I just made some stuff up about an older man who wanted to teach me, etc. He was super into that. I didn’t see him again. Every man I’ve come across that wanted to hear virginity stories has ended up being a super creeper and borderline pedo.”

—Michelle, 25

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5. “He wanted me to spit in his mouth and tell him what a piece of sh*t he was so I did. I mean, this isn’t that uncommon but at the time it was all I could do not to crack up. The whole thing seemed hilarious to me.”

—Jacqueline, 22

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6. “I had a client who wanted me to dress like his ex-wife (he brought a picture) and have conversations with me. It was a little disturbing at first but after a couple of sessions I realized this guy was harmless and just had a lot of bottled up emotions. When we had sex on the fifth date he thanked me and I never saw him again. You could actually see a transformation over those five sessions from a very unhappy and emotional person to a more relaxed and hopeful one. One of the few times I’ve felt like my work was objectively helpful to someone.”

—Sandra, 26

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7. “This actually happened just last week. A client had three different outfits for me for every part of our session. He wanted me to wear one during the getting to know you conversation, a second for foreplay, a third for actual sex (which he took off), and then he had me change back into the first one when the session was over. They were nice clothes too and he gave them to me as a gift which was cool.”

—Danielle, 25

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8. “I have two types of clients, people who want an intimate encounter and people who are working out psychological issues for themselves. Sometimes these two things cross over and sometimes they don’t. I had one client who was so insecure about his body that he wanted to watch me with another client beforehand so that he ‘wouldn’t do it wrong’. I ended up getting my boyfriend who’s totally cool with exhibitionism to pose as a client and we had a pretty hot sex session, apparently too hot. The poor client was so intimidated by what good sex looked like that that was the last time I saw him.”

—Anna, 26

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9. “I had one client who asked me to stick thumbtacks into his dick and got mad when I wouldn’t. Um, no. Also, get out.”

—Charlotte, 25

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10. “I considered this weird at the time because I was new to the game but I had one client, about 40 years old, who wanted me to crush bugs in stiletto heels while he watched. The guy brought a whole cardboard box of cockroaches (who knows where he got them) and a pair of vinyl heels in my size. He didn’t tough himself or anything, just watched as I played sexy exterminator. It was definitely gross at the time but it was also some of the easiest money I’ve ever seen.”

—Sarah, 24

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11. “I had one client who only wanted to see me when I was on my period so he could go down on me and he really enjoyed it. I have to say I enjoyed it too.”

—Catherine, 23

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12. “The weirdest request I ever had was from a guy who wanted to take a dump on my chest. When I said no he asked if I would take a dump on his chest. The answer to that was also no.”

—Ophelia, 22

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13. “I cam about once a week and the strangest request I’ve had that I was willing to do was a couple from the UK who wanted me to watch them have sex and kind of talk dirty to both of them while I played with myself. They were good looking and fun to watch so I didn’t mind at all but it was still the most unique non-gross request I’ve ever received.”

—Samantha, 24

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14. “I’ve had a number of ‘first timer’ clients but the only one I rejected was when this 18-year-old skinny kid made arrangements with me and then when he showed up and I spoke to him for about ten minutes it was clear his older brother had pushed him into the entire thing, that he wasn’t comfortable, and was possibly in denial about being gay. I felt really terrible for him and cancelled the appointment.”

—Denise, 30

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15. “In my profession you run into some extremely specific client fantasies and a lot of them seem very odd since you’re not the one having them. There was one client of mine who wanted to watch this specific Brazzers clip over and over with me and recreate it. I was fine with it but he acted like a director the whole time. He definitely seemed to enjoy it.”

—Cindy, 21

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16. “Not so much a weird request as just a weird thing that happened. I met one client who had warned me beforehand that he was unusually hung and I took this for the standard humblebragging that I’d heard so many times before. Well, when he arrive he really wasn’t kidding. The thing was as long as my forearm and thicker than my wrist and it looked even bigger than that since he was only about 5 and a half feet tall. I had to politely decline because there was no way I could have made that work. I actually felt bad for him though, he’d clearly been declined for the same reason before.”

—Jamie, 26

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17. “The first time I did a BDSM session I laughed through nearly the whole thing. It was something I was trying to branch out into because it can be a bit easier physically but it’s just not my thing. Every BDSM scenario I’ve ever seen or taken part in just makes me laugh because they all seem so absurd and hilarious. The costumes crack me up. I did two sessions like this and the second client who was apparently a BDSM veteran told me very nicely that this just wasn’t my thing. I was glad to hear that, actually.”

—Christina, 23

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18. “I have a fair number of clients who are trying to work through issues they have but I rarely have female clients. However another client of mine referred one woman to me who was a total sub but didn’t seem to know it. She had been married for 10 years and the sex between her and her husband had become almost nonexistent. Within three sessions I’d so worn her out with toys and bondage play that the problem became obvious. She didn’t feel comfortable being that vulnerable in front of a man. Once she knew it she was able to address it with him and herself. I mention this as weird because most people her age know what they like but she was basically just too stubborn to admit she liked being a sub.”

—Shannon, 30

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19. “I have a particular talent for being able to fit large things in my throat without gagging. I had one client who, once he discovered this, spent the entire session sticking large dildos into my mouth until he finished on my face which was fine by me but not at all the vanilla sex he’d said he was into when we chatted at the beginning of the session.”

—Emily, 20

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20. “I had one client who wanted to watch a friend and I pretend to study. He didn’t even touch himself while we did this but he would direct like ‘stretch and yawn like you’re tired’ and things like that. His one stipulation was that we never acknowledge his presence in any way other than following his directions. My partner was actually in school at the time and actually did study during these sessions which was even better for the client. I must have done this with her 10 times.”

—Janelle, 20

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21. “I was once asked to wear a pony costume so that the client could then penetrate me with a rubber horse phallus. While creative, I passed on that one. The costume material was polyester and I couldn’t imagine covering myself in it head to toe for more than a few minutes.”

—Rebecca, 26 TC mark

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