The world’s oldest profession—and its newer cousin industries such as phone sex and cam shows—isn’t just about sex. Often it’s about giving clients the kind of sex (and often just the kind of emotional/physical connection) that they can’t get at home. Sometimes, it’s because a client has a weird kink that they only feel comfortable revealing to a professional who won’t reveal it to others. Other times, whether it’s due to injury, trauma, or a bad domestic life, the stories of unusual requests people have—like simply being held—can be almost heartbreaking. One thing is for certain, though: in a world where revealing these things is impossible for most sex workers, the Internet is a godsend for these stories. Here, compiled from several different AskReddit threads, are 17 of the most fascinating tales from women and men whose time and attention are in high demand.
Oh, right. This is all (obviously) NSFW af. Seriously. If you get offended, we’re blaming you.
1. Let’s start off easy with this sacrilegiously non-sexual request from a webcam/phone sex worker in Israel. (via)
So, I’m Israeli and worked for a bit in webcams. We also did phone calls. Chats were monitered, phones weren’t, sometimes the manager would write me things to say.
An Orthodox Jewish guy calls. Asks me questions about eating pork and seafood. The manager tries to feed me sexy lines linking shrimp and clitoris or whatnot, but the guy isn’t interested. He just wants to hear me say I’ve eatten pork and it was so naughty and it tasted so good. Yeah, I drive on Saturday. I’m so bad.
edit: to clarify, my phone wasn’t monitered but the webcam constantly was, so the manager could hear my side of the conversation but not the caller’s. So he could hear me say “yeah, I’ve had shrimp last week” and tried to get me to take the conversation into a dirty direction.
2. Here’s a German escort with a fairly amusing tale of a tourist (she later clarified he was visiting from Japan) whose kink was harmless but not communicated beforehand. (via)
Escort here, an Asian man asked me to lift my skirt so that my thigh was exposed and asked to take off my shirt, ok normal so far I thought. Then he pulled off his pants and I was like yea it’s get down time. He then proceeded to lick and kiss my right armpit and rub himself on my thigh. It took every bit of power to not burst out laughing. He came about 4 minutes later and asked me how I was doing then asked me to leave. It was easily the most fun I’ve had on the job
3. This story comes from a self-described “dungeon lady” and professional sub. It was hardly the only one she had. (More at #16.) (via)
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.
I’ve got so many more, but that client story is my favorite!
When asked what happened if he “found a cavity,” she responded:
He’d get out a battery operated dremel tool with a fuzzy bit put on it, then ‘drill’ away between your toes. Can’t leave the dentist with cavities, ya know!
4. Here’s a story from a guy who spends six days a week at the gym and is a part-time escort. Be warned: this one is less “wacky fetish” and more “genuine human connection and sadness.” (via)
Part-time escort here (I’m a guy). I have had quite a few very strange and at times degrading experiences, but the two that stick with me the most are the reasons I still do this work part-time. First was a tiny and very beautiful Asian lady, probably 50 years old (i’m 45). I went to her house and explained in person what the services were that she could choose from. She said she just wanted to start by being held, a gentle hug. Well, after about a minute, I felt her crying into my chest (i’m 6’2″). I just held her and she stood there crying for 5 more minutes before I just picked her up and took her to the couch when I sat down and held her for another 20 minutes while she was crying. Just soft deep sobs (I’m getting a bit teary eyed remembering this). I asked if she was OK and she told me (without moving her face from my chest) that her husband never holds her, never has. So I just squeezed her a bit tighter and we sat there until the time was up (45 minutes was what she paid for). The second is similar, yet different. A very tall and physically unattractive woman in her mid 30’s wanted me to slow dance with her. She is 6’4″. Her height, combined with her looks, had led to her NEVER being asked to slow dance by anyone. We just danced for 90 minutes. It was pretty amazing to be honest. Both of those were strange, but even more than that, they were truly intimate. Most of what I do feels like masturbation with another person. Very impersonal and focused on orgasms. I have now pretty much focused the work I do on trying to have some kind of intimate connection. Dinner, dancing, cuddling, bathing, etc. On a certain level I have developed an addiction to it.
5. OK, this is a “my friend” story, but it’s short and great. (via)
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.
6. You’re probably familiar with phone sex and cam sex, but expensive sexting is also something you can pay for. (via)
I used to be a text sex operator. In the back of British newspapers and magazines there used to be a series of adverts saying things like “text BABE to 83777 to speak to a hot girl in your area”. There may still be, I don’t know. I was one of those babes (well, several). I’m a dude by the way.
Out of all of our crazy regulars two sprind immediately to mind. We had pseudonyms for all of our regulars, created by whatever operator happened to have a moment of inspiration when dealing with them. So let’s talk about 10,000″ Stan first.
His fetish was enormous breasts. Chats with him revolved around a magic substance called “expandium” – I don’t know whether he invented this or one of the other operators did. It caused the breasts to swell, and he would insist that the girl stuffed her breasts with it. Every session went the same way. He’d say “how big are they now? I bet they hurt! Shove some more in!” and you’d have to pretend to shove your boobs full of the stuff until they were as big as planets. As funny as this initially was, his sessions went on for hours and we had guidelines about how descriptive and expansive our replies had to be. We had to fill the whole 140 character message with original text time after time and he’d just text back “more! Do it again!”
The other regular that’s worth talking about was Prakash Boringest Man. As the pseudonym suggests, this dude was dull. He worked in a furniture store (in the warehouse part) and he didn’t even want to jack off that often, he just talked about his day. His really boring day. For hours. Bear in mind messages received by this service were charged at £1+VAT. He spent huge amounts of money having dull conversations with a fictitious girl. I occasionally wonder how this guy is doing. I’m pretty sure the service I worked for has long since shut down – I wonder if he graduated to actual hookers. He’d be spending about the same amount of money and at least he’d have a real woman to talk to…
…I only did it for a few months but it was decent money for a second job and I could do it from my sofa.
7. This story comes not from a stripper but from the club DJ who heard it from the very upset women who had a very lucrative deal ruined by a dumb co-worker. (via)
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.
At this point, a helpful commenter confirmed that the two smell different enough that ladies’ and men’s bathrooms have distinct odors. We’ll take their word for it. Responded the DJ:
…She wasn’t smart… and many of the girls were upset with her for screwing it up for them later.
8. This may not be “weird,” but it has a really happy ending. No, not like that, you creep. (via)
(Throwaway Account) My current SO was an Escort and we met through her work. I was her strange client. I was a law student at the time and had lost my previous SO to suicide. I really had a hard time “dating” (because of time constraints, etc) so, I paid an Escort to ‘date’ me. She would come over, and we’d made dinner, watch TV, fool around, take naps and generally be “boyfriend/girlfriend” on Saturday afternoon and evening.
We did this for over 6 months: every Saturday, she’d come over. She’d put on more comfortable attire and we’d decide on something to eat, either making it or getting take-out. Eventually she began to tell me what kinds of food she liked and what shows/movies she wanted to watch. I’d take initative and tell her what kind of sex I liked… and she did too. After a few months, we’d take afternoon dates to the park or to the movies.
Six months in, she’d stop leaving first thing on Sunday morning and we’d instead have breakfast, or go for a walk. Then it escalated to her showering Sunday morning and spending most of the day. I didn’t know if she wanted more money, so one Sunday I offered extra cash and she became quiet and said that she liked me and didn’t want to do this anymore as she thought it was hurting me. I told her I liked her…..
…. seven years later, I’m an associate partner at a firm and she teaches high school English. No one knows how we met or what she used to do. It’s like our weird little secret. We have this funny story that will probably go to the grave with us.
*Edit: still an ex-escort.
9. Of all the outlets for sex work, the domme/sub profession seems to have the best opportunities to say “no” to bad weird stuff and to say “yes” to good weird stuff. (via)
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.
10. Some people apparently use phone sex operators for purposes entirely different than arousal or even therapy—business consulting. (via)
Former phone sex operator here.
I had a repeat client who NEVER wanted to talk about anything sexual. He would call each time he came up with a new business model or pitch for his business: skirts for men. He was a cross-dresser.
I would spend at least 45 minutes listening to him practice the presentation he was going give to the bank or whatnot. I was expected to take notes and give critiques. Once he realized that I would actually do this, he would also call me back when he changed something.
He was one of my favorite customers because he was a gentleman and he always upped my average call time.
11. Da da da daa da…he’s lovin’ it. (Also not a direct sex worker story, but you’ll like it, promise.) (via)
I managed a strip club for a while. Believe it or not, things do happen in the VIP room…shocking right. As the manager, I just tried to play super oblivious and dumb to that fact, so if anyone did get in trouble, it was their liability instead of mine. We DID have rules against it and enforced them when people were caught. There were no camera’s and I didnt have enough bouncer’s to stand outside of the 8-9 rooms. So naturally things happened.
One of the dancer’s who I knew got to talking one day about the strangest things they saw in VIP or had to do in VIP, and she said,
“You know XXX that comes in every Monday?”
“Yea the dude that always brings in the Mcdonalds bag?” i replied.
“Yea thats him! You know why he always comes in with that bag?”
At this point I was like, shit we should really be checking those bags, dude probably has a dildo or something like that in it, right?
She said, “No, it actually has a hamburger in it.”
“Oh god,” I thought as my mind raced to try to understand what the burger was for.
She says, “he takes out the hamburger, puts it in a plastic bag, then sets it on the floor in front of him. He then has me get barefooted and step on the bag squishing the hamburger while he pleasures himself. Easiest 300 bucks I make every week.”
To this day I think about that guy on Monday’s. Because somewhere in some club someone is stepping on a hamburger for him.
12. Here’s a short story from a cam girl about a guy who was into some very long books. (via)
One guy told me he’d pay me €100 for me to (fully clothed) wear Harry potter round glasses and use an asparagus (as a wand) to recite spells. At first I though it was BS but went along with it anyway, he paid up….
13. Just because a story is odd and mostly harmless doesn’t mean it’s not really, really human. (via)
I was a cam girl for about six months in college. My weirdest customer wanted me to make him weekly grocery lists, errands lists, and just general “honey do” lists for things he had to do around the house. He was a young guy, maybe 25, and actually really attractive. British. He claimed he was lonely after his fiancée moved to Belgium for a year for school, and now they were on a break. These were all the things she used to ask him to do, and now she was too busy. So every week, I’d have a private show with him, and we’d drink coffee and go over that week’s list, and I’d wish him luck at work that day.
It was kind of sweet, kind of heartbreaking….I got the impression his girlfriend had just left him. He would sometimes talk about when she would come back, but I really doubted she would ever come back.
14. It’s unclear exactly what kind of sex work this woman does, but it’s clear she has a really good sense of humor. (via)
One of my very favorite customers ever would just want me to do things like sit on his lap (with all my clothes on) and pretend to be riding a motorcycle and that he was my passenger. He would want me to tell him a story about riding our motorcycle, like the scenery and what would happen if we broke down and things like that. He always wanted me to make the vroom vroom sounds and lean back and forth like I was going around curves.
And sometimes he wanted to “dance,” but what he meant by that wasn’t me giving him a lap dance, but just for us to sit together and dance really wackily–again, with all my clothes on.
Sometimes he wanted to do regular, less clothed dances, too, but he was always super polite and funny.
I also have a guy who always brings me books and wants to talk to me about literature. He will bring me like 4-5 books at a time and want me to look them over with him. But after we’re done talking he’s also into lots of kinky, domination stuff so he’s not totally innocent, either.
15. Let’s check back in with the dungeon lady from #3. Here are a few of her other favorite stories. (via)
1.
had a very nice gentleman come in wearing one of those dust masks. Wanted me to get up on basis pieces of bondage furniture, naked, and pose/spread. Then he would come right up and put his face about 1 cm from my parts and stare intently for a few minutes, then have me take a different position. Never touched me, even accidentally, over the course of the hour.
2.
had a gentleman who would book multiple girls, have us play completely dead, then whack us with riding crops and pinch nipples and stuff. If you grimaced or flinched our gasped, you were out of the (several hour, lots of money) session.
3.
had a very muscular guy come in who would shower, then once he was clean, would flex and want me to sink my teeth into his muscles and gnaw gently. Was surprisingly fun! These weren’t nips or play bites…he liked me in particular because I have a huge mouth and was able to get his whole rather massive bicep in my mouth, then gnaw with my back molars. I’ve bitten lovers before, but never like that.
16. Here’s another phone sex tale of several clients, proving that phone sex operators may, indeed, actually have the weirdest stories. (via)
I did phone sex for a couple of months back in 2004. I found it to be a depressing job because a) the pay sucks and b) you get some sickos. Unlike others in this thread, we were allowed to hang up on people who crossed certain lines (underage, incest, rape).
I had several memorable callers. One was a guy who claimed to be about 20 and in college, and he did most of the talking. He wanted me to just “breathe heavy”. So for 20 minutes he’s doing the most boring dirty talk I’ve ever heard (“I’m licking you up…and down…and up…now down…and up…”) and I’m sitting there panting and hoping he gets it over with already. By the time he finally finishes, I’m nearly hyperventilating, and was too lightheaded to take another call for an hour.
There was the redneck with a strong Southern accent who really liked ass to mouth play. So he’d want me to put my finger in his butt to play with his prostate and then suck on my fingers. Whenever I described something he liked, he’d say, “Oohhhhh, yerrr kinkyyyyyyy,” in this weirdly creepy way. He must have liked what I did because he’d call back often.
There was a Scottish guy who would call while his friends and roommates were in the apartment and talk to me like I was his girlfriend. When they left to go somewhere, he’d hang up. I’m pretty sure they had to know his girlfriend was imaginary…
…My favorite caller by far was one who wanted a very specific scenario. The operator, before connecting us, would tell me that he wanted to talk to a “she-male” (his words, not mine) who was flamingly gay and had very large breasts. I didn’t really know what to do the first time, so I just put on my best drag queen voice and threw in a lot of, “Oh, HONEY” and that sort of thing. He loved it. He had a really strong Boston accent and kept saying, “I love the quee-ahs!!” He was a regular caller, and I really started to understand why some called the job “phone actress.”
Finally, there was a guy who called himself “Super Leg Man” and I liked talking to him because all he wanted me to do was talk about how I worked out on the stairmaster all the time and tell him how muscular my legs were. That’s all he wanted for 20 minutes at a time. I dug it because it was so nonsexual for me and his long calls upped my call time average (which determined my pay rate).
Also, for some reason, about 75% of guys choose to call themselves Steve. No idea why.
17. Cam show workers, however, clearly have the most fun. (via)
Camgirl here, I hope that counts!
I have a guy that comes in every few months and wants to have a pretend “gunfight” with me. Like, we face off, draw our “weapons”, and “shoot” each other. He is super specific with the wording he wants me to use, and it’s such an easy show.
When asked how the gunfights worked, she elaborated:
Haha we just point our fingers at each other and make pew pew sounds.
Someone (correctly) commented that this sounded like a blast:
It is! Seriously, the more creative the fantasy, the more fun. I try to inject some humour whenever I can. I had a Boss/Secretary fantasy the other day, and I just started injecting office buzzwords. Like…”I want to be a real team player, sir.” and “Let’s get Dave in here for a team building exercise.”
18. This is equal parts fun and grossly informative. Or infartmative, if that’s what you’re into. (via)
Am a camgirl….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. Some people have kinks, this guy just liked crooks (crook is also a word for the bend your arm makes at the elbow). (via)
I used to waitress at a strip club. I remember one dude came in and asked girls to let him rub their elbows. …One girl did. She kinda thought it was funny. He didn’t like my elbows though. He was picky haha.
20. There is a really surprising number of very similar, and in some cases much more severe, fetishes like this one. (via)
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.
21. It’s not technically on-theme, but as a ball-kicking palate-cleanser, listen to sex workers answer all the questions they’re sick of answering.
22. Let’s bring the romance back with this delightful pie-in-the-face story (no, that’s not a euphemism). (via)
My wife is a cam girl. Some dude wanted her to do her makeup just like another girl (of whom he provided a picture) and for me to slam a pie into her face. It was probably the most fun I’ve ever had making $50.
Asked how his wife broached the request:
Well, the guy asked for it, but she was super nervous it was someone she knew trying to make her look stupid. I said “they’re paying $50 to see it. who’s stupid?”
“Ok”
I started laughing before I stopped filming, though. You also have to keep a pretty high acceleration for force required to keep a pie stuck to your hand horizontally so I hit her a little harder than intended.
Now, there were some very strange requests, and we never judged a soul. “That’s odd, but ok” was the extent. I didn’t think this guy was stupid, but anyone paying for this to make her look stupid would be stupid.
One thing I learned from her doing it was; there are a lot if dudes who love feet.
As for what kind of pie it was:
Nickelodeon style. Just whipped cream in a pie crust.
23. This guy who used to do cam shows remembers a client who took burning through all his cash more literally than most. (via)
I used to do webcam shows and I’ve been asked for all sorts.
Probably the most unusual was a guy who sent me money in advance of the session and the got me to burn it on cam whilst masturbating. Normally just £20 or £30 a time, but in our final session before I quit he had me burn two £50 notes and masturbate with the ash. I didn’t mind since he was paying for it himself and he always tipped well.
I’ve done all sorts of strange stuff though, pretty much any kink you can name I’ve indulged in.
Asked whether he considered counterfeiting the money:
Considered it, but I wanted to be honest and give the guy the proper experience
24. These stories have somehow avoided any really graphic descriptions of what genitals are doing during these meetings (well, except maybe that video), but this one was pretty noteworthy. (via)
A couple of times I had a young married couple who got me to jerk the man off inside the woman. As in, the guy would put his dick in the girl’s pussy, then I would slide my hand into her pussy around his dick, so I was sort of jerking him off and fisting her at the same time. That’s literally all they wanted (in a few different positions).
The guy actually had quite a large dick, just she had a very very loose pussy (the man could get both his hands inside her pussy at once). They were a very young couple, like 21 or something, so I dunno how she got to be so big (she said she hadn’t had any kids).
25. OK. There were a lot of weird ones. This one is the weirdest. (via)
I’m not a sex worker, but when I lived in San Francisco I had a few friends who worked as pro-doms at a BDSM dungeon in Oakland. They had all sorts of amazing stories.
There was one guy who booked a two-girl session, and brought two high school marching band outfits. He and one of the girls dressed up in the outfits, and the other girl yelled humiliating insults at them for being high school marching band dorks.
Another guy wasn’t even an actual client. He came over to book a session in person. While he was booking it, he asked if any of the girls needed to buy a car. “’98 Toyota Tercel 80,000 miles.” “Nah, we all have cars already.” “Are you sure?” “Yeah. When do you want your session?” “It’s been in a garage all the time. Looks brand new.” “I’m sure it’s very nice. About your session?” “I just got the tires replaced, so they’re brand new too.” “Listen, do you want a session or not?” “Sure, I just need to get my wallet from my car. I’ll be right back.” He didn’t come back. The other pro-doms said that he does this all the time. He doesn’t want a session. His kink is trying to sell you his car.
This article was first published by our friends at Someecards.
