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Sold myself to an older woman for sex

This is a confession of how I sold myself to an older woman for sex.

I was at a hotel bar on (in my mid-twenties) and struck up a conversation with a very attractive woman who was (my guess) around 50 years old. She was in town on business and we spent several hours just chatting and really hitting it off. She asked me what I did for a living, and with the drinking and the fact that I actually didn’t do anything for a living at the time I bullshitted her and told her that I, “made a living by pleasing women.”

She asked me what I meant by that, but I just played it coy and talked around it because I was BSing her and just wanted to see how she’d react. So, she comes out and asks, “So, what would you charge a lady to please her?”

I answered that it didn’t work that way…that if we hit it off and had a relationship that ..you know. There are gifts and such.
Well, anyways, a little while later she buys two glasses of wine and hands me one and asks if I want to come up to her room and finish the glass of wine with her. We go up to her room and immediately start making out. She tells me she doesn’t really want to kiss, but wants me to please her. At that point, she pulled down her undergarments, leaned back in the chair in the room and smiled. SO, I did what she wanted and just dropped on my knees in front of her and gave her head. She was actually kind of abusive in grabbing my head and graphically telling me what to do. It got kind of nasty but I didn’t care because it was such a huge turn on for me to be basically dominated by this woman.

After she came, she told me to stand up and take my clothes off, so I did. She gave me head till I was about to lose it then took me to the bed and gave me hand job to finish me. We fell asleep for a while, then I woke up and she was stroking me again. She got on top and took me into her and whispered in my ear that she believed me. Then she said, “Ok, finish me again” and rode my face talking dirty again.

Anyways, A little while later she got out of bed and took some money out of her purse and put it into my pants pocket on the floor. When I got back to my room in the morning I discovered she’d paid me 200 dollars. It is a memory that I’ve been conflicted about, but I’ve decided I’m not ashamed. To think about it now, that experience of selling myself to an older woman for sex is really exciting and erotic.

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