Who doesn’t love the pretty woman roleplay? In mine, the girl is not a hooker. We all know that’s already a reality for me. I often wondered what a girl would do for money. If you were homeless, with nothing, would you fuck a stranger for cash? 

I asked a few people I knew who had been down on their luck in the past. 3 out of 4 of them said they sold their ass for money to get a place to stay. All attractive, they weren’t the typical ones you would find on the streets. With all this said, I did something a little out of the norm for me last weekend. I was spending some time with a client of mine. We have “dated” for years, and he, at times, lets me indulge in my fantasies. So guess what? 

I was a homeless girl, and he was the Rich Man roleplay.

I set it all up that I would be outside of his hotel panhandling, and he would come out and offer me money for sex. Of course, I wanted this to be realistic, so I shopped the thrift store and got me some second-hand clothing. I don’t discriminate. This is not to make fun of the homeless plight in America. More or less, it’s a fantasy on how low someone will sink to have a roof over their head. With the economy in the shitter, I can imagine this happens a lot more than people realize.

Dressed in some tattered jeans, an old rock band t-shirt, and shoes that had a hole in the toe, I was almost ready. I left off the makeup and tucked all this long hair into a faded ball cap, and I will admit, I could have fit the part. One thing wrong, though. I smelled nice. I was not willing to give that up to get laid.

He played the role perfectly.

Standing in front of the hotel, I made 13.27 and a stern lecture about getting a job and doing something with my life. It seems the people of America are tired of paying for us good for nothing drug addicts who are too lazy to work. I bit my tongue so hard, trying not to go off on that woman. She had no clue what she was talking about, Another on the Trump bandwagon to hell.

My client, aka, the rich man, walked out, looking around, and the moment he found me, he had a look of hunger on his face. This was more for him than for me. Either way, I knew he wanted me. Dropping a few hundred’s in my hand, yes, it was a tip I got to keep, the man leaned in and whispered in my ear.

“400 bucks and I want it all. Come to room 408 in 10 minutes.”

Nodding my head, of course, this was all agreed upon beforehand. There would be much more than four hundred dollars in my hand. He placed the key card in my hand and went back to his room. I gave a girl nearby the change I had made and disappeared into the hotel. Can you believe I was asked to leave by security? Thankfully I had the key card, and I knew my client’s name. If not, I would have been out on my ass.

After 9 minutes of being detained, I arrived at the room. I was knocking soft before I allowed myself into his office. The client stood there with that look of disgust on his face, almost as though I smelled terrible. I knew I didn’t, but he played the role.

“Get those lice-infested articles of clothing off, and shower. You have seven moments to be out here and on your knees. My dick needs sucked Homeless girl”.

Clean, spotless even, but I did as instructed. I showered, washing with the hotel soap and was out and on my knees within five moments. I didn’t want to upset him, and to be honest, he seemed to love this roleplay.

He asked if I was hungry, and the moment I said yes, his cock was in my mouth. I guess he thought that was the proper way to feed a whore. He grabbed the back of my hair. His scent had me aroused. As did his Dominance. Rubbing his cock over my soft lips. The taste of precum flossed my supple lips, making me whine a little at the way he tasted. A flicker of my tongue over the slit, I loved the noises made while forcing his meat into my mouth. A quick slap to my face, he was so different this time. I like to roleplay.

“Homeless whore. What’s wrong. Did Daddy rape you, and Mama toss you out on your ass?”

That’s when the tears started. Neither was right, but I imagined that might be the case for many of the girls who live on the streets. Taking his cock down to the balls, he pounded my throat as he paid for it. Guess what? He did. He paid for an evening with a homeless whore who will do anything for a fix.

Stretching my mouth wide, his cock slammed down my throat. The sound of his balls on my chin echoing through the room, I swallowed every inch of his hard dick. Not holding back for my pleasure, he pulled out and shot on my face. Ropes of hot spunk dripped from my face, his dick drained.

“Go sit at the table. I will order you some food before I fuck that cunt of yours. Oh, and the ass too.” It was roleplay, but damn he was convincing.