My boyfriend Ryan, had opened my eyes to all sorts of sexual debauchery. He had encouraged me to live out all of my sexual fantasies, helping me in anyway that he could. One fantasy that he said that he couldn't really help me live out, was me be an escort.
He said that given that it would be our money that he paid me with, I really wouldn't be earning anything for it. Plus the fact that I allow him free rein to fuck me in anyway that he wants it wouldn't be the same as me being paid by someone else to fuck me. I agreed.
So we began discussing how we were going to do this. He suggested that I use Jay, the guy whom I had used as a bull when we experimented with the cuckold fantasy.
"You have already blown him by yourself, and fucked him in front of me. Plus he said that he would give anything to fuck you again." Ryan said.
"I don't know, I mean he was super sweet and I feel like I could trust him not to hurt me. I doubt he would pay for something that I've already given to him for free." I said with a chuckle.
"I'll message him as you and ask." Ryan said.
"Whatever you want to do." I said. But in truth I was very excited about the prospect of fucking him again, especially if I was going to get paid to do it.
Ryan grabbed my phone and began typing. After he was finished he handed the phone back to me to read what he wrote.
He wrote, "Hey, it's Marie. I was wondering if you would help me live out a fantasy? You said that you would give anything to fuck me, how much money would you be willing to give? I've always had a fantasy about be a prostitute."
I read the text and slapped Ryan on the arm. "I don't want to be a prostitute, I want to be an escort." I stated.
Ryan chuckled and said, "Sorry babe. I will clearly." as he took my phone and started typing, Jay answered back.
"I would definitely pay you to fuck you again. As far as a price, I guess that would depend on what all I would get to do and where you want to do it at." Jay replied.
Ryan typed back, "I would want to get a room, you can either pay for the room or I can add the room price in. How about $100. You pay for the room and you can do anything you want to me sexually except kiss me on the mouth."
Ryan handed the phone back to me and I typed "And you can't cum in me."
"Sounds like a great deal to me. When can we do this? My cock is throbbing now." Jay replied along with a picture of his big hard cock.
"I'm off work next Wednesday, will that work for you? We can meet where ever you get a room." I typed.
Ryan took my phone and added, "Get a room somewhere that has outside entrances to the rooms. That way i don't have to walk through a lobby."
"Why did you put that?" I asked Ryan.
Ryan said, "Because you don't want to run into someone you know in the lobby do you? Also I want to come in as soon as he is finished and reclaim my pussy."
"No problem." He responded and added, "I am really looking forward to eating your pussy again."
I assume that the idea of me selling my pussy got Ryan very turned on, because before I even sat my phone down, he jerked my leggings down and devoured my pussy.
I did as much research as I was able about how it all works between an escort and a "John" as the guy is called. I really wasn't able to find much information so I Ryan if he had ever been with an escort.
"Yes a couple of times when i was younger and traveled more." He said.
So I asked him how it worked, to which he was very open about explaining everything to me.
He said that most of the times that he had done it it was at brothels. He said that normally when you enter the room, the escort will have the John strip completely naked, while she steps into the bathroom and he lays the money on the bedside table. She has him strip naked to show that he isn't wearing a wire.
Then when its time to fuck, she has him lay on the bed and puts the tip of the condom in her mouth and rolls it on to his cock with her mouth and hand. That all sounds pretty hot to me.
I sat up a group chat on so that Ryan could see everything that Jay and I sent each other.
Jay messaged me a several times over the next few days trying to work out all of the details. Every few messages, he sent me some pictures of his hard cock. I figured that I should be polite and send him some nudes of myself as well. I made sure that every picture that I sent him I also sent to Ryan, except the ones that I sent Jay had my face cut out.
Jay asked me to bring a few toys, because he wanted to watch me masturbate while he sips his bourbon. I love playing with myself so I was happy to obligate his request.
I made sure that he understood that I would be taking pictures and videos to send to Ryan.
I also told him that Ryan would be waiting in the parking lot. And after he came on me that I wanted to let Ryan in to reclaim his pussy. Jay was all for all of this.
Wednesday finally rolled around and I was super nervous.
I wore a sexy little open bust corset teddy, fishnet thigh highs, platform heeled boots and no panties under a longer coat that barely covered my ass cheeks.
I pulled up to the hotel and sent a message to Ryan to let him know that I was there and waiting on Jay to arrive. I hot boxed my THC pen as I sat in my car. Jay finally pulled up next me, waived and walked in.
While I waited for Jay to come back out of the hotel lobby, I opened my coat and took
a few sexy pics and sent to Ryan. I closed my coat and inserted my dildo and pumped it in and out of my pussy a few times.
Jay came out and walked over to my door and opened the door while I still had my dildo in my pussy. I took one last hit off of my pen and pulled the dildo out of my pussy. I licked my pussy juices from the dildo as I let the smoke escape my mouth.
"Holy fuck." Jay said as he offered me his hand.
I stuck the dildo in my coat pocket along with my pen and grabbed my bag of real clothes as I accepted his hand as i stepped out of the car. My fishnet stockings and knees high pattern leather boots could clearly be seen below the bottom of my coat
We entered the room, opened the front of my coat, took a puff on my vape and said, "Get completely naked and place the money on the table."
As I walked across the room, I took out my toys and lay them on the bed before entering the bathroom.
Once I got in the bathroom I sat my bag on the counter and checked my hair and makeup.
I took off my coat and took another hit from my THC pen. I tweaked my nipples and said to myself, "Time to make some money slut." I blew myself a kiss in the mirror and opened the bathroom door.
I stepped into room and saw jay standing there completely naked with his hard cock pointing at me.
I took another puff off of my pen as I walked to the table and picked up the stack of 20s next to a pint of bourbon. I counted it, sat it back down and dropped to my knees in front of him and took his cock into my mouth. I took a few selfies of myself with his cock in my mouth and sent them to my boyfriend with a text that said, "Love ya babe. See you soon for your sloppy seconds."
I sat my phone back on the table raised back to my feet as I took another puff of my pen and said, "Can I pour you a drink?" as I squeezed his balls gently in my hand.
He nodded as I strokes his cock. I poured him a plastic cup of bourbon and said, "Have a seat and enjoy the show. I want to make sure that you get your money's worth."
I lay down on the bed and spread my legs as I began to trace my fingers along my legs. I reached over and grabbed my vibrating dildo and teased it up and down my slit.
I focused the vibration on clit for a few seconds before I inserted the vibrator into my dripping pussy and quickly brought myself to my first orgasm.
Jay sat his bourbon down, crawled up onto the bed and took over the vibrator from me. He worked it in and out of my pussy while he sucked on my clit. Ryan is the best pussy eater that I have ever been with, but Jay was a close second. He had me bucking with orgasms in seconds.
I handed him my phone and had video me as I came. I knew that Ryan would love seeing that.
After cumming and squirting, multiple times, I sat up and said, "I want to sucks your cock some more."
Something that he was happy to to do. His cock was in my face in an instant. I took back my phone and made another short video of me sucking his cock.
I looked up at him and said, "Are you ready to fuck me now?"
"Yes, I want you to ride me." He replied.
I opened a condom and held to tip in my mouth and used my mouth and hand to roll the condom over his large cock.
He laid down and I straddled him. I grabbed the base of his cock and slowly fed it into my dripping pussy. I took a few seconds to adjust to the size of his cock and began to grind back and forth, stretching my pussy to accommodate his large cock. He tweaked and sucked on my exposed nipples as an orgasm flowed through me.
After I came again I looked down and said, "Fuck me from behind." Something he was more then happy to do.
I crawled off of him and got on all fours as I stuck my ass in the air. He entered my pussy again and really began pounding me hard from behind. His cock was going so deep as he pushed me into another round of orgasms.
He saw my anal bead wand and said, "Can I use this on you?"
"Please do." I said with a smile.
He pulled out of my pussy to grab the wand as I took another hit of my vape. He spit on my asshole and inserted the wand in my asshole, then reinserted his cock into my pussy. I reached over and grabbed my phone, handed it back to him and said, "Get some pictures and videos of you fucking me like this."
