Real Life Escorts

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I’m an actively working girl. My first time was only about a month ago. It was through a website where you make offers to pay a girl to go on a date with you. They had to be very clear that it was’t a prostitution website (you compensate for time it said, many many times) but sex was fairly well implied.
My first time was with a 43 year old married man in town on business. He had contacted me about a week prior, through the website, offering $80 for a date. he said he would give me $2000/month for regular sex if we liked each other. I said yes, and he told me which hotel to meet him at and when. He also told me what to wear.
I arrived and he wasn’t too bad looking–slender and way more tan than you normally see as far north as I am. He bought me a drink first at the hotel bar and we talked for a bit. I was unbelievably nervous, but he was fairly reassuring. I was sure everyone knew what I was there for, and I was terrified of anyone calling me out.
Eventually he suggested we head up to his room, and I gave the meekest “okay” that has ever passed my lips. We went up and sat on the bed and chatted a bit more before he kissed me. after a couple seconds he pulled back and said “i like the way you do that. Let’s take off your clothes, and see what else you do well.” I got naked and gave him a blow job. I was’t really expecting him to finish that way, but he did.
After that he laid back on the bed and indicated I should join him so we snuggled and talked for a bit more.
Eventually he told me that he thought I was funny and sweet and “too good at that” and that he didn’t want to see me again in case he formed an emotional attachment. He said he just wanted sex, he didn’t want to mess things up with his wife. I said that was fine and we talked some more.
Eventually I started putting my clothes on. I was waiting for him to give me some money, but he was’t making any moves in that direction, so I sat and talked with him a little longer. Eventually I reminded him that we had agreed on $80 for the date, and he acted all surprised. then he made a show of looking for his wallet and then counted out each bill and dropped it on the bed as he did. I took it and left, not accepting his offer to call me a cab.
I felt pretty gross. My later experiences were better.
My first job was a private client, and I was totally calm on my way there and during, it wasn’t until I got into a cab to go home that I started crying. I wasn’t even upset, It was just involuntary.
A month later I joined an agency my first night they gave me this guy who became my first regular, always booked half an hour and I never stayed longer than 10. The other job of the night was in an office in an old industrial estate, two very married man and another escort. She was really nice and reassuring and helped me get over the initial embarrassment. The rest of the night was just sitting in the car with my driver talking about WW2 and listening to Frank Sinatra.
Most of the time I even had fun! But I still always got butterflies on the drive there. I think it was the anticipation of not knowing who the guy was, they could he sincerely nice or they could be a complete jerk.
I was an independent escort for 4 years. My first night, I was ridiculously nervous.
I went to an upscale hotel, nervously walked thru the lobby, hoping I looked like I belonged there, and not like what I was really there for. I was nervous the whole elevator ride up to his room. I walk to his room, lightly knock on the door. He opens the door, says (for the story’s sake, we will use the name Sarah) “Hi, Sarah?” and like an idiot I reply with my real name. We laughed it off. It was quick, 10 minutes. He was polite and clean. In the area for business. I ended up seeing him a few more times over the years, always very nice. Tipped on top of the hourly rate, which was always appreciated and made me choose to see him over other clients in the future. I have dozens of other stories if anyone is interested in hearing!
I’m a straight male escort and my first day of work was definitely not what I expected. I had (female) friends in the industry so I already knew what a normal job would be like. It’s the same regardless of gender.
In a typical booking, you meet, chat for a bit, sort out business, ask the client to shower then get down to business. For me, that generally includes a massage, foreplay, sex and a fair bit of conversation.
For my first booking, I received an email from a girl that basically went as follows:
“Hi, I’d like to book you as a birthday present for my friends 24th surprise party.”
I turned up early to help these girls prepare the surprise and they’re all insanely attractive. Out-of-my-league attractive. The girl who booked me then drops this bombshell on me:
“Oh, by the way, all of us girls are either escorts or strippers.”
I do my best to remain calm and collected and we all enjoy ourselves before the birthday girl shows up. They all turn out to be lovely girls and we all had a fun night. No actual sex but there were a few shenanigans that went on.
At the end of the day it was a definite “thrown in the deep end” experience but one I’ll never forget.
My first time and only time as a male escort, I didn’t realize that I was.
I used to hair model from time to time for wedding photographers and hair salons, so I have a few headshots floating around on different modeling websites and stock images. One day, I got an e-mail from a photographer that said he was practicing drawing and needed a nude male model to practice form. He said that he had a studio he could book and would pay $100 for two hours.
I was saving up for a plane ticket to come home to surprise my parents for spring break, so figured this would be an easy way to make a connection in the art industry as well as pick up some cash. We agreed on a time, he gave me his number and we talked on the phone to voice verify, as well as the studio that we would be working at.
When I arrived at the location, he was waiting there and said that the studio had been booked out to the night, and so he asked if I wanted to grab some food and then head to a hotel so we could just pose and draw there. I agreed.
We had dinner, made small talk about church and what I was studying at my University, and eventually got a cheap hotel room in downtown Nashville.
Eventually I got naked, and he asked if I thought I could get an erection so he could draw it. I said maybe, and he asked if he could help. I declined at first and attempted to get an erection, but eventually he said that he wanted to help and came over to me and started jerking me off. I didn’t know what to do, as he was significantly bigger than me. I started to try to get up but he laid on me and wouldn’t let me move. He kept saying “shh” and told me that everything was going to be okay and he would get me back to my dorm in an hour.
I gave up struggling and he gave me a blowjob while he laid on me and kept me down. I was so scared that I came in about 2 minutes. I didn’t say anything as he got up, tossed me my clothes, and said “let’s get you home.”
He drove me home in silence and as I started to get out of the car he grabbed my arm and said “I hope that was fun for you too, i’ll let you know if i need any more fun in the future,” and dropped two 50s on the seat.
I went back to my dorm and cried, not knowing if I just became a prostitute or got sexually assaulted.
Sometimes I get contacted by him, and got a couple messages from him while he was drunk, but I just ignore them and try to forget about it.
This sounds awful, but I was so desperate for money that I posted on Craigslist. Obviously that was stupid and dangerous, but I was 17 and I didn’t think about it. I basically asked people to bid to see who I would go with. Keep in mind this was a suburb in the midwestern US, so the money wasn’t crazy. I ended up driving 45 minutes to meet a guy who then drove me to his house. Again, so stupid. I can’t believe I didn’t die that night. This dude was like 50, heavy cigarette smoker, smelled like booze. I told him I was 19. (So stupid.)
The guy paid me $60/hr for three hours. He smoked a few bowls, talked about jazz, and then very creepily went on and on about my boobs. I jerked him for like 30 minutes with this horrible rose-scented lotion, blew him, and eventually we had sex. I was impressed he could get it up with how high he was and figured he must be on something else. That’s mostly what I was thinking about the whole time.
I didn’t feel it when he came because I was too concerned trying to give a good performance. So awkward, but he didn’t seem to notice. When I got off him there was no condom on his dick and I freaked until I realized it was still inside me.
We “hung out” for a little while (read: he slept and I tried not to puke) and then he took me back to my car, filled up my tank and gave me $300. All in all, not a horrible first experience, but also not wonderful. He’s called me a few times, but I never went back.
I started working because I’d gotten a few propositions through a dating website. I was studying med at the time and I was short on money. So one time, this guy made me what seemed like a lucrative offer and I agreed.
I didn’t know how any of it worked, so I told a friend I was going out and to call or text me in an hour’s time. We initially met in a park at night, sat in his very, very nice car, had a bit of a flirty chat, then made an appointment. He said he was 58 years old, but I think he was about 15-20 years older than that.
A week or two later, I drove over to his apartment. I was petrified, but I needed the money so I rang the doorbell. It was a lovely apartment, and he paid upfront. He was nice enough. He asked me to do some things that I didn’t want to do, so I said, “Maybe not this time.” Kept an eye on the time (via the helpful clock radio next to the bed) and thankfully he finished on time. Had a shower, bit of a chat afterwards, and then he kissed me goodbye on the cheek.
I think the fact that I said no to rimming annoyed him a little, but he texted later and asked if I would like to do a threesome with another working girl. Things proceeded from there.
I drank a heap of wine before I went to the agency. This was about 2.5 years ago when the industry was booming. I did booking after booking and went home with a massive wad of cash. I didn’t think about it too much. I just loved the rush of being booked and making so much money. The industry is dead over here now and I have no idea why.
Yes I was nervous, but it wasn’t really awkward. I had two clients that day.
I can’t even explain the feeling of my heart in my throat on the way to my first job. I thought my heart was going to burst out of my chest. But it ended up very well.
The first guy was really nice. Mid 30’s, extremely average looking. It was somewhat… boring. We started out with small talk, he offered me a bowl, which I refused. He smoked a little and then eventually kissed me. He had a bit of an ass fetish, I let him eat my asshole and lightly spank me, and then I let him put it in my ass- I figured that it was my first client, I should do a good job. I still see him from time to time, and he always tips very well. Along with the occasional gift of art or books.
And the second guy didn’t even try to have sex with me, he wanted me to smoke a cigarette while watching him masturbate. That’s about it. He paid me for an hour without question and I never saw him again.
I still escort from time to time. It’s great money and a lot of the time, it’s just lonely older men. My agency is very safe, my clients don’t have my personal number (unless I give it to them) and they make me check in with them before I go in and again when I’m done.) Don’t get me wrong, I get some strange requests, but for the most part it’s just sex. I love sex, it hasn’t discouraged me in any way shape or form.
My first time professionally was with an awkward Indian engineering student who paid me $500 to drive out to his apartment and do a two hour session with him.
Oh my gosh, I was so incredibly nervous the whole way, didn’t really know what I was doing, but once I got there, I pretty much went with the flow, chatted him up, started playing with him, and we had really epic conversation and he’s still responsible for one of my top ten orgasms (perfect little 4″ curved penis, hit my g spot with every thrust). Fucked twice, I gave him a blowjob while he was on the phone talking with people he was working with. I’m fairly certain he thoroughly enjoyed himself.
Immediately afterwards, on the drive back, I was just so utterly dumbfounded that I got paid that much to fuck a guy that was theoretically dating material if he had the time to date. It was tremendously encouraging, and I have those sorts of experiences with wonderful men (usually around thirty years my senior) sufficiently often that I’m not going to quit escorting until I age out.
When I was 18 I was tight on cash and decided, fuck it. I need a sugar daddy. I went on craigslist and found a guy. He wanted to meet me first and needed a new girl to replace his old one, he was willing to pay 4 figures per date. I drove to meet him and was stuck in traffic on the way for an hour or two. I sat at a Starbucks for a while waiting, he got lost because he was only there on a business trip. I was shaking by the time he came. We got burgers and drinks and sat at a table waiting for everything, talking. He was sweet but not my type, I was so nervous and shaking. We got to his hotel and sat and talked and ate, then started getting frisky. He would not stop talking about how amazing I looked and was and I know he was trying to flatter me but after a while it got really old. I stayed the night and left in the morning. He gave me money for gas. I later told him I’m sorry but the age difference felt too weird and he would have to find another girl, but really I just couldn’t stand him.
Then I found this married guy. We talked, I sent him pictures of myself and he was hooked. He ordered things off of Amazon for me to bring (we’re talking bondage/anal stuff) Anal was on the list of “necessities” to him. I was an anal virgin and reaaallly hesitant about it. I told him I wanted to be blindfolded for the thrill of it, but really, I just didn’t want to see his face. Drove an hour to a motel in his town to see him. The way everyone looked at me, I knew they knew what I was there for. I knocked on the door, it opened. I stepped inside where the lights were off, kept my eyes to the ground. He came up to me and started stroking my arms, my face. He instructed me to put the blindfold on and I did.
I hated it. I hated every minute of it. I lost my anal virginity to him and it was painful and I cried. I could feel his fat slapping against my stomach, he kissed me with his bushy beard tickling my face and I fucking hated it, I wanted to vomit. He gave me the $400 and I left. I cried all the way home.
He was nuts about me, wanted to take me on trips and buy me an apartment in his town and all that. I agreed to meet him again, but no anal and no kissing. I told him it felt weird to kiss him when he had a wife (I know, what a fucking lame excuse but what was I supposed to say, “you disgust me”?).
The second time he was coked out and had a hard time keeping it up. I had to awkwardly console him while he beat himself up over it, and suck his flaccid dick several times. We laid together for a while and we had a bit of “sex” (without a full boner it’s pretty much a fail). Once he gave up on the whole thing and admitted defeat, I packed everything up and sat at the edge of the bed. He brought my money and placed it in my hands, and told me to look at him. I was still wearing the blindfold and I shook my head. He took it off of me and told me to look at him. He was wearing a bandana that covered most of his face except his eyes. He had lovely eyes, and it made me want to cry when I thought of his wife.
This dude was convinced that I wasn’t in it for the money. I had a sick mind, I had a dirty side, and only he could fulfill it. I didn’t bother correcting him because I didn’t want to kill the self esteem he was building for himself.
I told him I couldn’t do it anymore. He messaged me a few times over the next year but I kept telling him no, no matter what price he gave me.
I regret both encounters to this day and nobody knows about it.
When I was 18 I was looking for a sugar daddy when the CMO of a very well known company (he didn’t tell me this, I screened him and the reverse image search brought heaps of Forbes articles on him) offered me $1000 for the hour if I came to his hotel room. I hadn’t considered transactional sex for money before but I was interested with the price so I showed up, got my money in about three minutes and went home with an uncontrollably large smile on my face.
I wasn’t nervous and I didn’t feel guilty but then again I’ve never been sexually repressed and did plenty of research beforehand. The only awkward part of the night was when he finished rather quickly and then, I’m assuming from embarrassment, threw the cash at the door and asked me to leave.
I’ve been doing it ever since (15 months now) and it’s been such a positive experience I’ve begun seriously considering taking a sabbatical from university and pursuing sex work full time.
Just after high school, my girlfriend got a job as an escort. It was back when pagers were cool, for reference. I dropped her off at work on her first night. The place was in a strip mall, just a little spot that looked like a half-empty travel agency or insurance shop. It was out-calls only, so you basically wouldn’t know it was an escort service. I hung out in town, because she said she’d page me if she needed me to come get her.
She paged me pretty quick. I picked her up and we drove to a McDonalds and got coffee. She was a wreck. She said that she told them she was going on a break, but that she wanted me to take her home. She wasn’t even going back to get paid.
She went on an out-call, to a guy’s house. They had bouncer-like guys to drive the girls places, and so a guy drove her to some guy’s house and waited outside in the car. The customer obviously wanted to have sex, and she was totally blindsided by this. I honestly don’t think she knew that she was a sex worker. She thought she was going to be a “go out on the town for a date” kind of escort. She even wore one of her nicest dresses.
Long story short, she ended up just watching the guy masturbate before fleeing the place and getting driven back to the office. Then I picked her up and she never went back. The thing I remember most clearly was when she was describing it to me. She was disillusioned, incredulous. “There were pictures of his wife on the walls! Pictures of his family!”
I remember the first time I accepted money for sex. A
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