This is way more recent! Due to the pandemic I had to stop working at the bar where I previously worked as a waitress and from the moment I could, I found myself another waitressing job. This was at a more fancier place which functioned throughout the day more as a high end bar and then at dinnertime as a restaurant.
Throughout the afternoon a man in his mid-forties had been working on his laptop at one of the tables. He had been buying drinks and snacks the entire time, gave good tips and kept to himself so he was a nice customer to have around. He spoke English with a British accent and he turned out to be in the country on business for a few days.
We chatted a few times and we had a nice match. Suddenly he asked if I wanted to have dinner with him that day, his treat. He said he thought I was a nice girl, we had a good vibe and would prefer it over eating alone. I didn’t have to do the evening shift, so I figured, sure why not! He gave me the name of a restaurant some of his coworkers had recommended and what time I was expected there.
I went home after my shift, put myself into a nice dress and met him at the restaurant. We had a nice dinner! Good food (Italian, yumyum), plenty of wine and lots of laughs. When we had finished he asked if I wanted to have a ‘nightcap’ at his hotel before ending our night. I knew what that meant of course, and honestly, YES PLEASE! This man was a treat!
We went back to his hotel suite and pretty much instantly started making out which quickly led to me being on my knees blowing him. He told me to get undressed except for my heels and get on the bed. I loved his dominance and gladly followed his instructions. I layed on my back and he got on top of me. He had a condom next to the bed which he wrapped on.
He started fucking me and I have to say, something in the motion of his hips was incredible! His cock got into such a curve inside me that it was truly hitting the right spot so to say! Combine that with the alcohol, the hotness of the guy, his dominance and before I knew it I was building up to an orgasm. Something which he felt and enjoyed which pushed him to keep on going and even start to choke me a little.
After I had orgasmed he told me I should “lick my cum of his cock first”, which I did and found so hot how he said that. then He turned me around after that and fucked me doggystyle for a couple of minutes as well. After that he stopped, sat down on the edge of the bed, pulled his condom off and said “my turn, make me cum”. I got in front of him and really pulled out my best throating game. That really pushed him over the edge and I had him cumming down my throat before I knew it!
He fell backwards on the bed, panting in exctasy. He then said that he had to get up early in the morning so he’d like to turn in for the night but that I could use his shower if I wanted. I gladly accepted and when I got out there was a fat stack of 250 bucks waiting for me on his nightstand! “That’s your tip for all that extra customer service” he said :p
I honestly did NOT expect to get paid for this one, I figured the dinner was already plenty, however I gladly accepted!
Source: reddit.com/r/gonewildstories/comments/10z1skm/i_felt_like_an_escort_when_i_accepted_money_to