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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.
Edit: Thanks for the editing help! :D
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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.
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.