37 Former Sex Workers Share Their First Time Working

Buzz Feed

09-07-2025

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.
"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 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. It was not a bad experience; the client was respectful."
"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."
"My first sex work experience was with a man I met through SeekingArrangement (a dating website that facilitates 'mutually beneficial relationships' between 'sugar daddies/mommies' and 'sugar babies'). We had an ongoing thing where he genuinely helped me to get off drugs and encouraged me to do better. He became my sugar daddy and even offered me a job in his company if we agreed not to mention our past. I turned him down, and sadly, he passed away months later. He had cancer and never told me. I think about him often, especially when setting and achieving my goals."
"Former stripper here. ... It was absolutely terrifying. I will say that I had really no idea what I was walking into. I saw an ad on Craigslist, sent in a bikini picture (smart), received an email from the owner, and went in that night. I thought I would just get some information and go from there, but they convinced me to do a short shift then and there...when I had never done anything like that before."
"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."
"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."
"I've had issues with sex and being emotionally connected, so I thought I'd be great at stripping and sex work in general. The first shift was my last because I found the aggressiveness of the girl who was supposed to be helping me out to be unpalatable. It was day shift on a weekday, so hardly anyone was in there aside from a small handful of people. One dude who seemed ready to buy a dance kept getting followed around by the other girl. He kept trying to get away from her to talk to me, and I had no idea what I was doing and didn't want to step on any toes. After my first dance, he finally was able to approach me and told me to watch out for her and that they just returned from her aggressively giving him a blowjob in the parking lot, and that, apparently, she wouldn't stop complaining about me."
"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'm technically in the industry. I work as a lingerie barmaid — called Skimpys in Australia. My first day was terrifying. I'm confident and always wear tiny bikinis on the beach and post pretty revealing photos on my Instagram just for fun. But the first day, I was shaking, fixing my outfit, and being awkward. I realized my job was less about what I wore and more about the conversations I had. Don't get me wrong, I'm grateful to have a job with such a good hourly rate that put me through a degree, but it was so emotionally exhausting. It's called surface acting in psychology — constantly being on and in a good mood, laughing at dumb jokes, smiling at creepy compliments, and men double your age drooling over you, barely looking into your eyes. The half-naked part is honestly the easiest part of it. It's the constant pretending and the character you put in that's exhausting."
"I was a sex worker. My first client was actually nice; I was absolutely terrified, though. It hadn't been long since I had my daughter, so my body wasn't 100%, but he thought I looked amazing. It built my confidence up."
"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 started stripping on my 18th birthday. My first lap dance was a $200, 15-minute private dance. The guy was 25 and from the UK (this was in the USA). I cried while sitting on his lap because I had no idea what to do. He was so nice and just hugged me and told me it was okay, even though he had just spent $200 to have some girl cry on his lap. I hung out with him the rest of the night (with one of his friends and one of mine)."
"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."
"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??"
"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.'"
"I got into being a sugar baby and a sex worker not from financial need but more so curiosity and desire. I found it hot that people would pay me for something I already wanted to do. I'm not romantically attracted to men, but I have a good time sexually and enjoy their company, so it was very easy for me to not have any emotional messiness. The first client started up during the pandemic, so we actually ended up talking on the phone for months before we were able to meet up. By the time we did, I was very comfortable with him and was already receiving monthly funds. I left the scene when I started dating my girlfriend more seriously, but I have no regrets!"
"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. He was kinda lowkey good-looking. ... The guys on SeekingArrangement are super weird, though. I had various weird interactions with different guys after him, but he was actually pretty chill."
"I was pressured by my then-husband, of all people, to become a sugar baby at the ripe age of 38. I went on my first sugar date, and the sugar daddy and I instantly got along. We fell in love over the course of a year. We're together for life now. 🤷🏻‍♀️ I believe I've won the sugar life lottery."
"I was 18 and anxious as could be! I showed up to the hotel room. The guy let me inside and then started questioning me. 'How do I know you're not a cop?' I decided to get things started by telling him, 'Maybe you should check me for a wire.' It was pretty simple from there."
"My fiancé and I started doing it six months ago. I was pretty nervous for the first five minutes until we realised it was a normal guy, and then it was super chilled out and easy. We're no stranger to threesomes, so no confidence issues there, but we'd never done it for money before."
"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."
"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."
"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."
"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."
"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."
"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."
"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."
"I tried only twice, but it was weird, so I stopped. My first time was with an older man. I showed up on time, but he was finishing his salad, so I sat at his dinner table, twiddling my thumbs, waiting for him to finish. Most awkward 10 minutes of my life! Finally, we went to the bedroom; he got undressed and laid on his tummy. I offered a brief massage, but he was so frail I thought I was going to hurt him. Then he turned, and I started playing with him. He liked it but said he couldn't get hard because he had cum once already that day. ... I know he was old, but it still hurt my self-esteem a little."
"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.'"
"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."
"I did a solo OnlyFans for about three months as an experiment. I made $1K+ but felt empty; as a guy, I think I did well, but it just didn't feel right. My first client wanted a lot, and I gave in. I probably sat there texting for an hour because I had such a large bit of dopamine getting my first sub, but it wore off after realizing how much time I spent for $4."
"I have only had three shifts at a brothel, so I'm not super experienced. I was very lucky. Had this guy come in who specifically asked for me. He made me orgasm by eating me out, then we cuddled, and he gave me a great massage. Thanks, Mike!"
"I was looking for something high-paying and kind of stumbled upon my shop's recruitment ad. I applied, thinking nothing of it, and was surprised to be contacted regarding an interview. I live in Japan, so in my case, I needed to have the right residence/visa status, which I do. I was also fortunate to pick a shop willing to take a chance on me, as I think the majority of shops would not be open to allowing a foreigner to work for them."
"I still work in the same brothel I began sex work in. I was so nervous as I barely knew what the routine was and what to do. He was a regular, and we sat in the hot tub and talked before getting into it. He was very understanding and nice. I look back and realize I got super lucky as there is a whole range of men who come in, and for the most part, they aren't all kind, easy, clean, or not gross."
"My first client was a very nervous cutie who didn't seem to know where to start with explaining or doing. It was nice to know how to help someone feel relaxed, and that didn't need to perform or feel pressured. It reminded me how to be clearer with my own language/profile, though — that I only accept older clientele, and how I view/accommodate first timers. :)"
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."
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.
Submissions have been edited for length/clarity.