homeless woman, paid her and raped her

She was homeless, about 35 or so I guess though she looked 50. She had been paid to have sex before she said so. I paid her $10 for a nude BJ. Her tits were small and yet sagging, her brown nipples were very big and erect most of the time. They stuck out under her shirt, she didn't have any bras, really didn't need them. Her body was not very saggy yet, she had a pert little ass and really nice legs. She was petite, probably not bad looking if she was cleaned up. Her pussy was in full growth, not curly like a lot of pussy hair, straight and medium brown. Half way through the Bj I gave her another $10 and told her to lay down. She knew what I wanted and took the money. We were behind some bushes in an area where she camped out in a park. She laid back on a blanket and spread her legs, and started rubbing on her pussy to get it wet. It was a very pretty shade of pink her inner folds, for such a little woman her slit was probably 4 inches long, she had a nice pronounced clit, and a non-virginal, but tiny little pussy hole. Her legs pulled up, she grabbed my cock and put it to her hole and I went in. I bred her, cumming in that hairy little fuckhole. She let me, though didn't like that I was sucking on her little tits while I was fucking her. It was good, I wanted to go back since I was in town for almost a month.

The next night I went back with some warm food, and cold drinks.I gave her $20 and she stripped, sat naked and ate. Then she laid back, rubbed herself again, and told me to get on with it. She parted her legs more, and I fucked her again. Getting up she was wiping my cum from her pussy she turned and that ass was the most perfect thing ever. She had a body like a pre-pubescent, straight down the line, only a very slight indent in her waist. I asked her about coming back regularly and she was OK with it but emphasized that it could only be me, no one else with me. Eventually I learned that she'd been through gangrapes on the street before.

After fucking her for a week sometimes staying longer to fuck her twice or get a BJ then fuck, I asked her how much for her ass. She refused, she didn't do that! The next day we sat and I brought some whiskey and she was getting drunk. I earlier had given her the money for the BJ I had, and I wanted to fuck. She asked for the extra $10 to fuck her, and I gave her $50. "What's this for" she asked. My only answer was "it's for this" as I pounced on her naked body, roughly turned her over, and spread vaseline I'd bought on her asshole. She was crying and telling me not to do this, she didn't do THAT. I held her down, which was so easy because of her petite body, and holding my hand over her mouth, I slowly moved my cock into her back hole. She was closing her eyes, in pain, grunting, kept saying PLEASE NO over and over again. I heard her say it hurt too bad, but I started fucking that virgin ass. I came in probably only 10 to 15 minutes. I took pictures of my cock up her ass, my first virgin hole ever. Her ass was so damn tight. I told her it was tight and it felt too damn good as i blasted my cum up inside her rectum. She just stopped struggling, just laid there, I moved my hand from her mouth and gently pulled out my cock. I got off her and she immediately went to a bucket she had and sat on it to push out what I'd jammed into her. She wouldn't look at me just asked me if I was going to leave now. I did.

I waited a day or two, but would watch and when she'd leave, I'd go in and left her some money and some food and drinks. I went back after three days and apologized to her. "Do you have another $50?" she asked. I did, so she said to give it to her, she stood up took off her pants and panties and laid down on her belly taking the $50. I left the vaseline when I left, and she pushed it to me. "I still am gonna need this" she said. I lubed her ass, slowly finger fucking her asshole, then lubed my cock. "Get on your hands and knees please" I instructed and she was now doggie in front of me. Pushing my cock into her she still winced and I tried to go slow this time. I reached around and was rubbing her clit while I fucked her ass, then reached under her shirt and played with her tiny tits and puffy, pouty nipples. I came and she sat down and started drinking some of the whiskey i left that time I raped her. Breaking the silence she spoke "I don't care that you threw $50 at me, you raped me, you raped my butthole" I answered "I know, I'm sorry, but you're so damn attractive with the best looking butt I've ever seen."

There was a price. I took her to the apartment the company rented for me, and let her get cleaned up, wash clothes, clean her belongings. In bed, her clean, pretty, and lying there with her tiny tits and hairy pussy, I handed her a $20 and she said no. While she was there she fucked me for free, and I bought her clothes, even helped her get a job. For the rest of the time, I had a full time girlfriends or I guess sex friend. After about 6 or 8 times in her ass, she got to where it was very easy and using a vibe on her clit while buttfucking her made her cum.

Then I left town, left her with new clothes, makeup, shoes, a job and a tiny studio apartment as part of a homeless project.

I paid to fuck the homeless woman, even raped her in her ass. I think it was good all around thought.