Homeless

I was 20, hadn't been laid in several weeks or really, months. No excuse, but out of town, around back of my hotel was a homeless woman. She asked for money, and once I gave her some she kept bothering me all the time. After 5 days of this, I told her I'd give her $50 but she'd have to show me herself naked and let me feel her all over. She thought about it and then took me around behind some large dumpsters and got totally naked. I was guessing she was in her 50s, turns out she was 39 but life on the streets I guess aged her more. She was clean, not dirty like I expected. I felt her sagging, pretty big tits, even sucked on each of them. Then I reached behind her and was pulling her to me while I felt up her ass. Reaching behind her and going between her legs I was rubbing her pussy then up her crack, rubbing her lower back, then back between her cheeks and to her pussy. She sort of laid her head on my chest and was moaning. I pushed her up against a wall, and started rubbing her off. She must have cum as she was breathing deep, then holding it and tensing up rubbing her pussy rapid fire against my hand, biting her lip. She looked up and said thank you.

The next day she offered again, and I told her that wasn't enough. I ended up getting bjs from her, and eventually I fucked her pussy and then her ass. She said she'd never done anal before and I believed her, it was not easy for her I could tell. She was incredibly tight. We never kissed it was just sex and a monetary transaction.

I am very ashamed I did it, I never should have taken advantage of her like that, and gave into my youthful horny self. Yes I paid her, yes she took money for it, but . . . I still feel bad.

Needless to say when people ask about my past fucks, even my wife, I never mention the homeless woman.