Homeless Pretty Woman

Just another Wednesday night, going home after work as the sun is setting. Life has become boring. I go to work selling insurance, get in my Honda, go home and masturbate. My name is Jarrod and I'm a 24 year old man. I'm very tall but average looking. I'm able to pick up girls at the bar but lately that's gotten boring. I've been looking for a little excitement...

I came to a stop at a red light and in the darkness saw a homeless woman holding a sign saying, "hungry, please help". She must have been about 50 and was probably very attractive in her younger years. But now she was dirty and wrinkly from obvious drug abuse. Her blonde hair matted and tangled. She was very skinny, wearing a green T-shirt and dirty jeans. She would not look up, and her face was sad.

As traffic moved along I started to think about this homeless woman. By this point I was right next to her. I decided to take a chance and roll down my window. She noticed and stumbled over.

"Hello young man, can you spare anything?" She asked in a raspy voice. I had a $5 bill in my cup holder and my hand shook as I reached for it stumbling upon my request.

"I'll give you $5 if you show me your tits."

She was obviously very offended and looked like she was about to cuss me out, until she saw the money and sighed. She leaned into my window and lifted her shirt showing her saggy little tits. They looked like they would have been nice years ago, but now looked like deflated balloons. But it really turned me on. I handed her the money and the light turned green and I drove home. I sat alone on my couch and rubbed my cock to the thought of this woman.

The next night she was there again. This time I had a $20 bill in my cup holder. As I pulled up next to her again, I rolled my window down. She remembered me from last night and flared as she came up to me.

"I've got $20 this time and it's yours if you stroke my cock," I said. She looked into my lap and saw my dick was already out. With a sad look in her eye she reached down and began stroking my cock. She was jacking me off in the middle of the road! The light turned green and I still hadn't come. I was on the verge of explosion and there were cars honking at me to move. I drove down the road with my cock pulsating. My mind was going crazy with dirty thoughts. It really didn't take much to get that dirty bitch to do anything I wanted. I pulled into McDonald's and ordered two meals. I looked into my wallet and saw I had a $50 bill. I took a route that led me back to that stop light. She noticed me and approached yet again.

"I'll give you $50 to come over and have dinner with me tonight."

"I ain't no hoe," she replied. I held out a burger and I could tell she was hungry. She reached for it and I pulled it back and told her she can have it if she comes with me. After a couple seconds of thought she got in the car and I drove her to my apartment. In the short drive I found out that her name is Monica and she lost everything due to drug abuse. She had been sleeping behind a dumpster.

We pulled into my apartment and walked up the stairs and led her to my living room. I had fed her and she asked for her $50.

"Not yet," I said as I unzipped my pants and pulled out my cock. I held it in front of her face and as she mumbled some profanity, eventually took it into her mouth. I grabbed a handful of hair and fucked her face while she gagged and spat. The feeling of knowing I could do anything made my cock tense and I blew my load in the back of her throat. She looked up at me with tears in her eyes.

"Give me my $50 now," she demanded.

"I tell you when it's time do you understand?" I said sternly. I pulled her shirt from over her head exposing her tits. Then I told her to remove her pants as I grabbed a condom. She did so, but flared at me the whole time. I was already hard again and saw the huge bush this unfortunate woman had. I laid her down on the couch and kissed her gently. She kissed me back as I pushed my cock into her hole. This smelly bitch was so tight! She felt amazing. Her moans and the way she matched my rhythm was unlike any other woman I had experienced. I kissed her again, pushing my tongue into her mouth. Her tongue met mine and her fingers rode through my hair. I started fucking her faster and faster until I came again. I handed her the $50 and went to leave. She got to the door and then came back to give me a passionate kiss before leaving for real.

Now it's Saturday and I can't stop thinking about her. I had the day off and decided to go shopping. When I got back home I returned with a short white dress with new underwear, as well as a razor and perfume. It got to be later in the evening on my cock was craving her. I got in my car and drove to the same light. And there she was.

"Get in," I said. Without hesitation, she jumped in my car and we headed towards my apartment. As soon as we got there I directed her to my bathroom. I told her to take a shower. I watched as she stripped out of her raggedy clothes and watched the dirt run off of her as the water hit her skin. I smiled and turned around and walked to the kitchen. I started making dinner and poured us some wine. After some time, she came out of the bathroom looking absolutely stunning. The dress was so tight around her petite body and her hair looked amazing. She sat across from me and she wouldn't stop smiling as she ate her dinner. We engaged in conversation and laughed a bit.

After dinner we moved to my bed where I pushed her onto the bed and pulled down the new thing I bought her. A freshly shaved little pink pussy stared back at me. I began to lick her clit and those beautiful moans came from her. I inserted two of my fingers inside of her while continuing to flick her clit with my tongue. Her moans were so loud and her rhythm matched my fingers. I took a third finger and pressed it against her asshole. It made its way inside her and her body shook as she came. I couldn't wait to fuck her. I put my cock in that little pussy and slammed my hips into her body. It did not take long as I came inside of her. My cum leaked out of the pussy I had grown obsessed with. We laid in bed and kissed passionately, not knowing what tomorrow was going to bring.