I have sex when I can with homeless women. Sometimes it's for money, sometimes for food. I did my last one when I was in New Orleans last weekend. It was cold, and raining and at night this one woman about 45 years old, thin body was being hassled by a couple of the homeless guys under some store canopies, and she moved in the rain behind a dumpster. She had her jeans opened up and was tucking her shirt in. She didn't have on any panties or bra and I could see her black pussy hair. As I approached her she didn't even close up her jeans and we were talking while I was looking at her pussy. I started with an offer of some hot food, she said that none of the tourist restaurants in the French quarter would let her in. We went to a quiet bar/restaurant that was pretty dark. I got her some food and we both ate and talked. She was only 34 but had been on the streets for 4 years. After we ate and drank some she said "I guess you want to fuck me for this huh?" I responded that I wouldn't turn down some sex. I told her that she could come with me to my hotel, we could take the garage entrance and go up to my room. She could bring some clothes and I would have them cleaned and returned on the fast 3 hour service. She could also shower and shampoo. She asked what I was into and I gave it to her straight. I wanted sex in all ways, and I wanted kink. I would stick my dick in her mouth, her pussy, her asshole, and I would probably make her get fucked in front of the window of my hotel which looked out on busy Canal street. I would also want to watch her piss and shit in front of me, and I may just write things on her body with marker.

Up in my room I got her clothes, including the ones she was wearing, and sent them to be cleaned and returned. In the meantime I opened all the dr**es in my suite so anyone looking up from the street or other buildings across could see her walking around naked, laying down getting fucked, or sucking my cock, whatever we did. After a blowjob and a buttfuck ending with me shoving my cock up her c**t and ramming my full load all over her pussy, I ordered us some appetizers and wine from room service. I looked when the knock came and it was a guy bringing the food up. I made her lie on the bed with her legs spread so he could see the cum on her black pussy hair. He came in and dropped off the room service cart, he couldn't take his eyes off this thin piece of ass that had obviously just been fucked. "If you want a quickie go ahead and fuck her" I said. The guy looked at me then her, and couldn't believe it. "I'll step outside in the hall if you want, but go ahead and fuck her. You can fuck her mout, her pussy, or that sweet asshole, whatever you want" I told him. I could see the hesitancy. "Don't take too long" I said as I headed to the door to wait outside in the hall. He came out and thanked me after about 10 minutes. I went back and saw her on her belly her asshole covered in cum and gaping open. He must have had a huge cock because you could put a half dollar inside her ass and it would fall out. I picked up the marker and wrote "Buttfucked, ass whore" on her butt.

We had a good time, even kept her with me for a few days before she returned to the street, by that time I let 6 other guys fuck her for free, sold her to 8 different guys, and fucked her myself a lot in all holes, watched her shit and piss in the bathroom and wrote all kinds of shit on her body. By the time she left the rain was gone and I gave her a couple hundred bucks to see if she couldn't get off the streets a bit. I saw her my second to last day in town and she looked worse than ever. She had the money stolen, been beat up, and then I made her go behind that first dumpster I saw her at and fucked her up her butt, and wrote on her belly: "No good, pass around, cock sucking, cum guzzling whore" then over her c**t I drew a big dollar sign, and I left.