25 Sex Workers Discuss The Weirdest F*cking Requests They’ve Ever Gotten

Human sexuality is a deep, deep, deep, dark well. The range of fetishes, kinks, and taboo sexual desires is enormous, and yet largely undiscussed. For many, their cravings are a source of great shame, the most private and classified facet of their lives— secrets they don’t tell anyone.

Anyone but sex workers, of course. And people don’t so much tell them as much as hire them to fulfill their closeted fantasies. We perused a couple of AskReddit threads asking sex workers about the strangest requests from clients and holy cow did they deliver.

1. I feel like Bucket_O_Beef’s customer could’ve just asked a regular tax guy for this rate:

He wanted me to do his taxes with no pants on. 300/ hour.

2. ChillingMarmoset’s friend basically has every pitcher’s fallback dream job…kinda:

Not my story, BUT… A buddy of mine in college was one of the university’s starting baseball pitchers. He also happened to be gay. (Nobody cared about the gay thing. He was a nice guy. Whatever.) After college, he got an entry-level management job in the Miami area. The pay was crap, of course, so he started moonlighting as a RentBoy to augment his income. Eventually, he got hired by some wealthy closet case. Showed up at the client’s home where he was led into the garage and shown a 50 gallon barrel. Filled with oranges. The client went into the opposite corner of the garage, stripped down naked, and asked my buddy to throw the oranges at him. As Buddy tells it: “Man, I’m gay and everything. But I was a college baseball player. I throw in the high 80’s. Are you SURE you want me to do this?” Client LOVED HIM. Buddy plunked the guy for 20 minutes and got asked back every two weeks for the next 3 years. No sex. Just oranges. C’est la vie.

3. Spergmom has not one but three fantastic stories. Thanks spergmom!

Left the business around 13 years ago, but I still have a few memorable experiences to share.

  • One client wanted me to pretend to sleep, while he had his ways with me. Turned out that it only involved him groping me, spreading my ass and whispering “Oh my lovely little baby girl” while jerking off for half an hour. Just charged him my normal 30 min fee – Easy money, really!
  • One of my regulars progressed from licking my crotch to me facesitting him, to farting him in the face – and finally he had me pooping him in the face. It disrupted my OCD controlled toilet habits severely, but at the equivalent of around $750 per session it was all worth it.
  • Played the part of “suspicious customs officer” many times with another regular. Somehow it always ended up with an extremely thorough cavity search and simultaneous penis inspection. Never found anything though…

4. chasethenoise has a similar story, except, uh, classier:

I had the chance to ask an escort this very question. She told me she had a regular who liked her to shit on his chest, then take a spoon and feed it to him.

5. I don’t know who I feel worse for in Hurray_for_Candy’s sorry tale:

Not a sex worker, but I bang lots of dudes, and this one guy just wanted me to insult his tiny penis for like an hour while he jerked off. Tell him how tiny and useless it was. I did it, but I didn’t enjoy it, I don’t like saying bad things about cocks no matter how small they are.

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6. GirlHips shares the best and worst job memories:

Former Pro-Domme here. Client wanted me to scald him in a tub until he passed out, revive and repeat for several hours. I said hell no.

Client had a fantasy about being forced into a leotard and legwarmers and forced to do jazzercize with my canes as motivation. I did that and it was awesome.

7. Just when you thought you’d heard it all, Jitzgrrl rolls through with the dental foot exam:

I had a guy lay me out on the table, take my shoes off, get out a set of dental picks and mirrors and electric toothbrush, and do a “dental exam” on my feet. For an hour. Checking for ‘cavities’, ‘polishing’, ‘flossing’, etc. I was supposed to play the whole thing straight as if it was really my teeth he was examining. Never did his penis come out of his pants. It was actually a totally great time, if a bit bizarre to start.

8. Props to Gnashty Bounce for still kissing his ex:

My ex girlfriend use to do amateur web camming. One night she had a rather odd request. This guy asked that she put her dildo in her ass, take it out, and then gag herself with it until she puked. She did, and I honestly couldn’t tell you how much she made off the request. I can however, tell you that she spent an obscene amount of money on me, leading me to believe the gig (or gag, ~slaps knee) payed well.

9. The oddest part about mudbuttcoffee’s story is that ‘strip club DJ’ is a real job:

I was a strip club dj for a bit… Had this one odd duck that would come in and pay girls like $200.00 to piss in a glass for him… This happened several times, then once the girl took it to a bouncer and had him pee in it. She took it back to him, he took one sniff and said “this is a man’s urine” Left, and never came back while I worked there.

10. Hisladyalways’ story is actually kind of sad…

I work at a gentleman’s club as a VIP hostess. Guests would ask me for everything they wanted (blonde girls, fake Boob girls, drugs, sex workers) and the most unusual request I got was a man was looking for an escort to take out for $800 dollars to pretend to be his wife at a company dinner. Apparently he was single and gay and lied to his co-workers about having a wife to get out of a few events. The lie got out of control I guess…

11. Warning: you’ll probably want to unread asrah_’s contribution:

a girl I know used to be a dominatrix, her worst was a guy who used to pay her $800 per half an hour to stick syringes into his penis

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12. anotherglassofwine’s client must have a penis of steel:

Used to work as a stripper a few years ago. Hands down, the weirdest thing was when a guy in the VIP section bought a few dances and then asked me to step on his dick in my 7 inch stripper heels.

At first I was being careful, but then after he assured me that there was no way I could hurt him, I went to town. I even threw in a few combos where I’d step on it and twirl. It was actually pretty fun. Afterwards, he bought my thong for like $50. Really fun night.

13. I’d like to know where SchrubSchrubSchrub lives so I could make a point to never speak to any men in that town:

Was a sex worker, dealt with a lot of fetishes

  • A guy once hired me to pretend he was famous and act like I was a huge fan of his that got lucky.
  • One guy hired me and payed me twice as much to clean his apart whilst wearing nothing thigh-high socks and sneakers.
  • One guy had this big blue suit that blew up into a big ball and made me look like the girl that turned into a blueberry in Willy Wonka and the Chocolate Factory. He had me put that on, and then jerked off on me while I acted like I’d been turned into a blueberry.

14. What a time to be alive, right TeslaMust?

A college friend of mine used to play a game with her bf called “Indiana Frutta(Indiana Jones + Fruit(in italian)).

Basically she inserts chunk of sliced fruits in her vagigi and he has to discover them and pull them out with his tongue like Indiana Jone’s whip exploring a cave.

15. NOOOO, WoWDisciplinePriest, NOOOOOOOOOOOOO:

Previous sex worker:

$60 to give him my used tampon. Then, after giving it to him, another $60 if I would watch him eat it.

It was $120 on a slower night. All I could think was that he was going to get a terrible blockage later, no matter how well he chewed it.

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16. Well, cookiemonster247, how much would it cost?

I had a man once ask how much it would cost to get naked, wear sailor hats, get into a jacuzzi filled with pepto bismal, shave his ass and clip his toe nails.

17. Some genius responded to Dr_HQ’s comment by saying “To be fair that’s likely how Joyce intended it to be read” and it’s the most accurate thing I’ve ever read:

I had a friend who was a sex worker. My favourite story from her was a client who wanted her to stand in a corner, facing the wall, wearing nothing but combat boots and reading from Ulysses.

18. misscamgirl has boundaries, ok?

Am a camgirl, as the name implies. Only saw this guy once so maybe he didn’t like my art skills, who knows. He asked me to draw on crazy eyebrows, like stick straight pointed upwards ‘angry’ brows so I did. Then I needed a clown scowl. That was enough for the face so then he had me draw fangs on my nipples. Vampire tits haha. And then lastly, a face for my pussy. Complete with eyes, a nose, and mouth. We both had a lot of fun, I could see him and I don’t think he was jerking it, just laughing hysterically with me. Wish he’d come back! Recently had a different guy ask me to just fart, like continuously. He didn’t know that for fart porn vids the girls literally pump their asses with air. Yeah that wasn’t going to happen…

19. Imagine if pollywog313’s client was actually white? I sure hope so:

I had a friend who was a phone sex operator. She’s from South Carolina and has a strong southern accent. One of her callers was a black guy who wanted to be showered with racial slurs while he got off. She could only think of a few of the most obvious ones, so he had to help her along. “Call me spearchucker!”, “Call me porch monkey!” and so on

20. You’d think the coworkers in DontQuoteThisComedy’s situation would’ve quit within, like, a month:

I had an escort service a few years ago. One of the clients used to come with a plastic bag and a paper bag. He would get one of the girls to hold the plastic bag while he took a dump in it. Then he’d put it in the paper bag and take it to work. He said he would then hide the bag in various spots around his law firm, waiting for someone to find it and that was his get-off.

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21. cheevocabra’s old coworker went 0 to 100 real quick:

My old coworker was this Abercrombie model-looking surfer guy and one day some rich trust-fund guy approached him at the gym and offered to buy his socks after he was done working out. Told him to name his price. So my coworker just jokingly said $100 and the guy whipped out the money. This starts happening every time he goes to the gym so my coworker kept raising the price and eventually the guy started making him meet him at a restaurant so he could buy him lunch before he bought the goods and after like 6 months it all culminated to him trying to get my coworker to come to his house and rub his dirty feet all over his face while he jerked off for a few thousand dollars. My coworker was pretty creeped out so he cut off contact, but man, rich gay foot fetishist was a cash cow. I’m pretty jealous.

22. Yo, Indeedsir, introduce me to your friend. She seems like a good time.

A girl I know is a Dom. She has one client who pays for public abuse. I was at a bar with her last month and she asked if I wanted to see her next appointment:

She waits for this guy at a street corner and they walk together a hundred feet or so, then she starts raving and screaming at him about how pathetic he is. She screams at him to give her money, so he stops at a cash machine and while he’s there she’s just goading him.

There’s a crowd now and he takes out £250 and hands it to her.

She takes it, spits in his face and walks away, we go and have more drinks.

Other clients of hers, if we’re bored, she’ll call one up and make him collect us and drive us to another city for a party or shopping somewhere. He’ll wait in the car and be ignored, or come into shops silently and pay for whatever she picks up, then when we’re done drive us back AND PAY HER FOR THE PLEASURE AFTERWARDS!

Good times.

23. BBchick had a symbiotic relationship with her bruised-ball client:

Guy used to come see me every week and pay me to kick him in the balls. HARD. Repeatedly for 5-10 minutes. And I usually wore boots. He obviously loved it. He would flinch a bit, but usually asked me to kick him harder. I was apprehensive the first few times, but quickly learned that he seriously wanted me to kick him as hard as I could. If I had a stressful week dealing with assholes I would look forward to him visiting so I could take out some aggression.

24.😦 throwescorts😦

Former male escort here –

Had a larger, 50ish lady ask me to snuggle with her in a rocking chair. Wanted me to suck on her nipples as if I were nursing. She stroked my hair the entire time. It was really really weird and kind of sad.

Lasted for about 20 minutes. When we were done, she offered to jerk me off but I told she could do so if she wanted to. She said no, so I got dressed and went on my way.

25. Let’s just ruin the remainder of your day with MeatTornadoLove’s story:

I know I’m late to the party but I have a great story.

I used to be a male escort, had a guy once who I had going so bad he was up in a swing and I was shocking the shit out of his balls while he begged and screamed for more. I told him to shut the fuck up and stuck a plug up his ass, and that was the breaking point. I’ve had people use a safe word before and it’s really no big deal, everyone has their limits, and I can dial the intensity back and adjust the play pretty well.

This guy, however wanted to escalate. He used the safe word to take me out of the zone in order to discuss the next thing. This guy wanted me to castrate him.

I had to talk him down from that, he said nobody ever got him to the point I got him, and he was certain that it would never be this great again so why bother? Let’s full fill this last request. I refused and gave him a bit of aftercare, Sent him on his way. He came back a few times that month, never asked for that again.

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Related-ish: 17 People Shared Their Disgusting Little Secrets And The Results Were Hilariously Disturbing

 

 

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