"I Made Four Figures In 30 Minutes": 21 Shocking Stories Of Sex Workers' First Client Encounters

Yahoo

15-07-2025

Recently, Reddit user drowning_fish_101 asked, "For those who worked (or still are) as a sex worker, what was it like having your first client?" and the responses were super fascinating. Here's what former sex workers, strippers, and others in the sex industry had to share about their first times working.
1."I was a 22 y/o crossdresser at the time, and I found a guy (let's call him Kevin) on Grindr. He said he liked spoiling people and said he'd pay me to have sex with him. He was a ... not my type, but I wasn't bothered by it. I let four people know exactly where we were going to be and who he was before I did it. I dressed up in a cute fit, and he complimented me, and I felt affirmed at a time when I was questioning my gender. He asked if $100 was okay. I was only expecting half that, so of course, I said it was okay. We had sex outside, and he was really sweet. We cuddled and talked more than we had sex. He told me his nephew was transitioning and started living with Kevin because he was escaping his bigoted parents. Kevin asked for advice on how to make his nephew feel safe and stuff. Kevin even respected my boundaries as far as what I did and did not want. He was a really caring guy who was just lonely."
"After I left, I bought some outfits and sent pics of me to him. I haven't heard anything after that. I hope he's doing okay."
—u/RavenQuill
2."I remember my first client wanted a foot job. I was in no way prepared for giving that type of a repeated movement with my legs. It was so physically exhausting. I was in my early twenties at the time. I just remember the client looking really young. I wore lingerie the whole time and did the foot job. After he came, he just wanted to talk for the rest of the session. He asked me a lot of questions about the job I was doing."
—u/LauraLovexxxgodes
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3."I was about 20/21 at university and worked in a cafe run by these two funny gay guys. They told me one day that they knew a lot of older women who were looking for sex and willing to pay for it. All I needed to do was turn up, be dressed nicely, have dinner and drinks, maybe a river cruise through the city, and back to their hotel for sex. This was before smartphones, so not once did I get a photo of these women beforehand, and I was always worried about what I was walking into and if I could perform."
"I only did it five to ten times for money, and I was fortunate that none of them were completely unattractive, and they were all extremely nice and interesting to spend time with.
The first one was a lady in her fifties who was career driven and just kind of missed the boat for marriage and children. First impressions: she looked like a cold corporate woman, but she was actually quite lovely and just lonely and wanted attention. We actually caught up again a few more times for no money, but she would always pay for everything."
—u/GhostKingHoney
4."I was absolutely terrified. I entered the industry for the first time as a mature woman, surrounded by young girls with long legs and perky tits. I had always been a very sexual person, so I thought that I'd be like a fish to water, but I was not prepared for the emotional toll of trying to sell myself to every man who walked in. My first booking was a man in his early thirties, and it turned out he was high on coke. ... He couldn't even get hard. I thought it was me. I never doubted my oral skills but assumed he wasn't attracted enough to me. It was some of the more experienced girls who later explained coke dick to me."
"Fourteen months later, I'm still in the industry and love it. The selling aspect has become so much easier. I make good money and meet some truly fabulous people. But whenever I get upset about missing a booking or not getting as many as I'd like to, I think about how excited I was the first time I was told that someone was paying to have sex with me and the dread that immediately followed about 'what now,' and I realize that a quiet day isn't so bad."
—u/BustyRedd
5."He asked to be humiliated. I smiled and made him confess everything and saved the receipts. Now, he tips extra just to keep them hidden. First client. Still my favorite toy."
—u/Mistress_Zaveya
6."I was 18, fresh out of high school, and wanted to make money for Christmas, but nowhere 'normal' was hiring. I got work at a brothel/parlor that I didn't realize at the time had a horrible reputation. It had known gang-affiliated clients. The owner would collect her 'room fees' in the morning (of a $200 one-hour booking, we would get $125 for ourselves, and $75 would go to her for using the room) and have a general vacuum and tidy up before leaving for the day; whatever girls were working that day were also the 'receptionists,' answering the phone, doing all the laundry, collecting money from clients, cleaning rooms, and locking up at the end of the night. We had no security on site. It was run out of a residential house, and it was JUST us girls for the whole day: 10 a.m. to 11 p.m."
"My first client was an absolutely lovely older fella whose client nickname/regular visitor codename was Hot Rod. He was a super gentle fella, took it really slow, and actually tried to get me off before anything else happened (I was too nervous to, bless him, but he tried his best). He really tried to put me at ease and enjoy myself, tipped well, and was just a really nice guy.
The next 10 clients (10 hours as a first shift) I had that day were back-to-back bookings who were mostly alright, but some of them were super rough and tried to push boundaries (it's illegal to have sex for money without a condom or protective barrier between you and the client, but very legal/decriminalized to have sex for money with protection — including blowjobs with condoms on, which most guys absolutely hated and tried to get out of all the time). They tried to go over the booked time, and one sixties-ish man tipped me at least $500 to give him a blowjob with no condom and cum in my mouth because he knew I was 'fresh' and didn't have the backbone to say no at that point.
I lasted about a week at that place before I quit. I burnt out so quickly, having 8-12 clients every day, because everyone wanted to test ride the barely legal new girl. Thankfully, during university the next year, I found a much nicer parlor with an actual receptionist, and the owner stayed on-site the whole shift. Clients were actually vetted before they could book, and all the money exchanges happened in an actual office with security cameras all over the place. I worked there for three more years before I 'retired' when the business sold and I got into a career with animals. I'm still friends with the old owner and most of the girls I worked with to this day."
—u/FailAffectionate544
7."I was 19, and I was told I would be taking a woman to a wedding. There was no talk of sex. Just the promise of a bonus from the woman who set up the date if the woman I escorted gave me a good review. The mark was a 32-year-old divorcee who was absolutely gorgeous. The wedding was for her ex' sister, who was also her best friend. I played the part through the ceremony, where she pointed out her ex. He was skinny, short, and had no muscle — totally the opposite of me. We went up to change for the reception. That's where I learned what it would take to get the bonus, and I obliged. She was exaggerating and screaming since the ex was in the next room. We were all over each other at the reception. Back to the room where we performed all night, and she would get digs in on her ex. The morning, she pushed me out of the door naked in front of her ex, whom my manhood must have dwarfed, by the look on his face."
"Luckily, there was a room service cart. I used the house phone to call my handler. I was driven to her house, and I got the bonus. I was enchanted by the mark but disappointed because I didn't get out with the new tux or suit. A week later, those were dropped off with an envelope with 5k and a note saying I was a bargain, amongst other things. I admired her and wish I would have seen her again."
—u/Arnaghad_Bear
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8."When I was 19, I was stationed with the US Air Force near Tokyo. One time, at a local gay bar, I was essentially recruited by a local massage service...that was expected to end with extra services. I was young and enlisted, not making a lot of money. So the amount of money they told me I could make with my clients seemed really attractive. My first time working was a Friday night. I got off work, dressed, and went to the massage parlor. Clients could come into the shop, or we could be called for an out-call to a hotel. Clients would choose us in person or from a website. The boss came in and told me I had been 'reserved' for a hotel meet-up. I cleaned up and took the subway to the nearby hotel. I was so nervous. My Japanese was very weak, and I felt like everyone in that hotel lobby was staring at me and knew why I was there. ... The short elevator ride up, I almost bailed. I was about to have sex with a total stranger."
"What if he wasn't hot? What if he wanted things I didn't enjoy? I got to the room, and a well-dressed, decently fit man in his forties answered. I went in, and we barely spoke since neither really spoke each other's language. We showered, and I nude-massaged him until it was 'time.' To my surprise, he wanted me to TOP! It hit me — I just assumed I would always be the bottom. I was a twinky young guy. I didn't even consider I would be topping.
So it didn't go well. I couldn't stay hard. The condom was too small. It was hot in the room. He was very passive and didn't seem to be into it.
We finished, and I couldn't have gotten out of there any faster. I didn't feel great about it, but it got easier over time. I did it for the rest of my tour. I met a lot of really nice clients who mostly just seemed either lonely or looking to avoid the hassle of sex dating apps. I did top way more than I normally do, but I got better at it."
—u/throw_me_4way
9."He was a prominent Canadian businessperson, and I was a college student in Indiana in my twenties. He was married and used a fake name, but I figured out who he was. He was kind and generous, and we saw each other several times whenever he came into town. He really liked to see himself as a mysterious benefactor and had a weird breeding kink, but he was a lovely man. Then he died of cancer and had a big plaza named after him, and sometimes I see it mentioned and think, 'Huh. That was a weird time.'"
—u/All_In_A_Row
10."The first time was purely just to say I had done it. I was 19 and went on Craigslist and answered a post from a guy asking for a threesome with two women. We messaged back and forth for a while, but our schedules didn't line up right away. He had a woman text me to verify he wasn't dangerous and actually paid. He lived a bit away, and I didn't drive, so he eventually ended up driving to my city, picking me up, and getting a hotel. I brought a bottle of wine and some weed because I was nervous. We ended up talking for about an hour. Then, we eventually moved on to the deed. He basically had a micro penis, and that was my first time ever seeing such a sight. But I keep it professional. At some point, probably because I was tipsy, I started making out with him. That caught him off guard."
"Anyway, we finished (well, he finished), and I changed. He paid me and took me to a friend's house. I never met up with him again, but he did text me to ask about the kissing. He was so used to sleeping with working girls who had strict boundaries (rightfully so) that that had never happened to him before. He then proceeded to text me for nearly five years after that to try to arrange a meet-up. I figure I was more personable than other, more experienced girls, and he liked it was more like a girlfriend experience."
—u/-zombie-mami-
11."This guy liked to buy custom videos of me, and he asked me if I would make a video for him of me fucking some college student. I found a guy who I already wanted to fuck but who just lived an inconvenient distance away, and it turned out he was down to be filmed. I drove to his place, had an AMAZING time, took a video, edited it together nicely, sent it to the buyer, and got $3600. So, it really couldn't have gone better."
—u/Brueguard
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12."I didn't even realize it was happening until he paid me. I sneaked into the Bike Stop in Philly at the age of like 17 or 18, back in like 2002. Immediately, older dudes are offering me drinks and chatting me up. It was so much attention. I'm a chubby nerd, and it's new and flattering as hell. I wound up talking to this dude for a while. He was talking about how he was a lawyer. I was asking him about cases and shit. Finally, he was like, 'Are we going home?' and I was like, 'Yeah, alright.' So we got back to his place, we did some stuff, and it was all fun. I hopped in the shower for a minute, and when I got dressed and came back out, he handed me like $100 and said, 'For the cab,' with a wink."
"Yeah...I went back the next week. I made so much cab money."
—u/Netzapper
13."I was extremely nervous. I knew nothing about my client, and I was worried about whether or not she would enjoy herself. I arrived at the hotel and knocked on the specified door. She ended up being a perfectly average middle-aged woman. I followed my instruction manual to the letter for all the introductory stuff. She warned me that she doesn't get off easily and requires a lot of warmup."
"Long story short, I went down on her for at least 40 minutes. She went from zero reaction to a muted one, but I didn't see anything that indicated she might have gotten off. I raised the white flag after 40 minutes and apologized if I didn't get her off. She said, 'Are you kidding me? I got off like five times!' She ended up repeating this with me two more times and left some great reviews for me. She also gave me some insights about the industry. 10/10 first customer."
—u/WindJammer27
14."I'm a former OnlyFans girl. I'm well-educated, but I'm from a poor country, and I'm a breadwinner. I was so, so lucky; my first client was a sweet man — a widower. He just wanted company and some playtime. For my second client, I was even luckier. She was a lovely woman. She was just lonely. It was her first time ever on OnlyFans, trying it out. Everyone else after that were pigs. I really felt like an object. I was dissociating a lot and hated my body. But I stayed on for the money to pay for school (Master's, mind you) and my parents' hospital bills...until my second client (the woman), whom I had gotten close to, offered me a large sum so I could leave the business and focus on finishing my degree and getting another job where I was safer."
"I stopped. We kept in touch, got even closer, and fell in love. We're dating now. I'm in a good job and I graduated. It's been two years now, and I'm happy and safe!"
—u/ThrowRASufficient34
15."I was in my late twenties, had lost my job, a parent had died, I was about to be evicted, and my cards were maxed out. I knew a ton of gay escorts and porn models. I pretty much kept it to referrals only, as for a quick minute, I was on Rentboy. It mostly was that either someone wanted a three-way or the friend couldn't do it (usually out of town). So I wasn't nervous the first time I did it on my own. The first time I did one alone, it was pretty fun, and I earned a bit of money. He was in his late fifties and pretty good-looking, but nothing super wild. He came six times. It lasted like 30 minutes, and it was four figures. And when I stopped, I still hooked up with him."
"I was on Doxyprep, so I would charge extra without condoms. I don't do drugs, so that got strange at times, but most didn't ask. I kept testing every two months, and things turned out fine health-wise.
I met a few people, and most were professionals who saw it as a convenience. When I smelled meth, or something seemed odd, I just left."
—u/ughliterallycanteven
16."I was a sugar baby to different successful men for three years. My first sugar daddy had 800K followers and 'public figure' in his Instagram profile bio. He smiled and told me not to be nervous because I was just his type. When I asked him what that was, he said, 'Scared skinny European girls who don't talk.'"
—u/slavicgypsygirl
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17."Does phone sex count? Many moons ago, there used to be phone numbers in little sleazy magazines with pictures of pretty girls and women. Phone 18-year-old Missy now! Talk to 33-year-old Karen, the single mum, now! 55-year-old granny Rita is ready for your call now! Ring Gina, the transgender 24-year-old, for a chat! None of these people actually existed. All but one of us on the phone lines were ex-working girls. I was the exception. We signed into the phone system on our own home phone. We heard a code when calls were connected, and then we knew which character we were to play."
"I was terrified for the first call. I had no idea what to say, but I got through it. The boss listened in. Funnily enough, I turned out to be exceptionally good at it. I bought some books on the psychology of sex and sexual fantasies, and that helped. I was running the company, doing the phone system, the rostering, and checking on the girls' calls within a couple of months of starting. I was also making phenomenal money. We were paid by the minute. Later in my employment, I was offered a video slot when they began doing video calls. I left the company. I was fine being an anonymous, never-to-be-found voice on a phone line, but no way was I going to do video chatting.
... The most popular characters on the phone lines were the transgender ones. By a country mile!!!
I also became adept at sound effects. Some guys wanted to hear you urinate on the toilet (always kept a glass of water next to the loo), high heels walking across a floor (high heels on a coffee table), a 'wet pussy' was a mouthful of water and a finger squishing around in there or a piece of latex with some lube and of course a vibrator had to always be on standby.
Personally, I preferred the guys who were just lonely and wanted someone to talk to. My record was over four hours with one caller. The system would automatically hang up every hour as a reminder to the caller about how much money he was spending. Depending on the line he rang in on, it was $1.95 or $3.95 a minute. I got about a dollar a minute. Not bad sitting at home in my comfy clothing watching TV with closed captions whilst pretending to be in sexy nightwear with an insatiable sexual appetite!"
—u/Lightfairy
18."I met him on SeekingArrangement. I was 19 years old. We had a drink at a dive bar I was familiar with in the downtown part of my hometown. I blew him in the backseat of my car for $200. I had sex a bunch, so I was 'experienced,' but I never did it in a straight-up transactional way. I had worked some shifts at strip clubs, though, so I wasn't SO green on taking the money. But the money actually changed my life. I needed it badly for some bill. I went immediately to the bank right after he finished to deposit and pay the bill. I didn't use a condom because I'm an idiot, but yeah, that was the first time."
—u/stephiree
19."I was on the SeekingArrangement website for not very long, and there were some genuinely nice men, looking for their taste, I guess (IDK a better way to put it), but there were also some straight-up creeps. I will admit I slept with a guy 30 years my senior, and we had arranged a monthly agreement where he'd pay me $2000. It didn't work out, but the men I met on there beforehand made me question society. They were blatantly cheating on their wives, not even trying to hide it, saying you will get this amount if you have a place I can fuck you, or this amount if I have to rent a hotel."
—u/leighsknees16
20."It was stressful AF. Meeting someone new and then having sex as a service instead of for fun was definitely anxiety-provoking. ... For me, I think most of the jitters came from the fear that I would disappoint the client in some way. What if he sees my body in real life and doesn't like it? What if I'm too awkward? What if I'm not as good at tomfoolery as I thought? What if he wants me to ride him, but I lose my balance and break his dick and accidentally punch him in the face while trying to catch myself??"
—u/Iskracat
21.And finally..."It was a blast. I got tossed and flipped around like a doll. She was a 6ft Slavic woman. Mira, wherever you are, I miss you so."
—u/This-Peace654
If you've worked in the porn, stripping, or sex industry, we want to hear your story — share in the comments below or via this anonymous form.
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