Escort Diaries: Roleplay



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

I actually 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 just to get a place to stay. All of them attractive, they weren’t the typical one you would find on the streets. With all of 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 the homeless girl, and he was the Rich Man.

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, and this is not to make fun of the homeless plight in America, more or less it’s just 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 actually 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 just to get laid.

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, Just 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. Maybe 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, and 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 stopped by security and asked to leave? Thankfully I had the key card and I knew my clients name. If not, I would have been out on my ass.

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

“Get those lice infested articles of clothing off, and shower. You have 7 moments to be out here and on your knees. My dick needs sucked Homeless girl”

I was clean, spotless even, but I did as I was instructed. I showered, washing with the hotel soap and was out and on my knees within 5 moments. I didn’t want to upset him, and honestly, he seemed to love this role.”

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. Gripping 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 he was forcing his meat into my mouth. A quick slap to my face, he was so different this time. I liked it.

“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 like 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 demanding 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.”


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I love a man who can find my dirty little secrets and force me to confess them all. All this beauty doesn’t come without brains. Top of my class, I started college at the age of 16, and am very savvy to the ways of the world. Most that I attend to are the CEO types. They demand a girl with brains as well as the outer package. Nothing is sexier on a Male, or Female, then an intelligent mind! A pretty girl with a filthy mouth is always a keeper. Well that’s what my Mother would whisper to me as she tucked me in bed at night.

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