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Chicago Student Prepping Midterms While Waiting for Clients

I am 19 years old and I’ve been an escort for almost a year. Living in Chicago and going to school is tough, so I pay for it all by working a few days a week, and I’ve even got money leftover to splurge a little on myself. It’s sort of out a damper on my social life, but I wouldn’t give up this money for anything. I can’t wait to graduate debt free.

Day 1

9am It’s a work day. I’ve got so much prep work to do. As soon as my alarm goes off, I’m up and in the shower. I use my expensive soap. Clients eat that shit up. I shave a bit, just to be sure. 

9:30am Time for makeup. It’s a full look day. Smokey eye and a dark lip. Perfect for the outfit I have planned. I get my hair dryer to and it falls in little ringlets down my body.

9:50amI slip on my work panties. I consider not wearing a bra, but I’ve got one that matches the black lace panties so well, I just have to wear it. Once those are on, I pull on a little leather skirt and a soft t-shirt for a rock band I’ve long since stopped listening to. I toss on a leather jacket and a pair of black stilettos. I’m really going for the groupie look here, I guess. 

10:15amI’m in the car with a banana in hand. I eat a bite every time I hit a stoplight.

10:45amI pull into the hotel. It’s a little far from home, and traffic was awful today, but the rates are better a little out of town. Plus, the owners have always treated me well. I’ve already got a room key, so I just walk right inside. This is my only early day, and I always struggle to make it in on schedule. Hopefully I haven’t kept anyone waiting. 

11am I’ve got the room prepped and I’ve turned on my work phone. Almost immediately it lights up with texts I got after my last session. Mostly “thank you”or “see you soon”, but some a little more explicit. 

11:10amA call comes. He says he wants to see me. I tell him where he can find me. I don’t recognize the number, so he must be new. 

11:30amClient one knocks on the door. He introduces himself. Let’s call him M. He’s tall. Kinda cute, but a little rugged. He’d look great with a shave. He’s quick to get started. He knows the cost, so he sets it down on the stand and lays on the bed. I ask what he wants. He says he wants my mouth on his dick. He wants me to choke myself on it. I do. 

11:45amHe comes in no time. I don’t care. I still get paid the full hour even though he leaves right after. 

12:30pmNo more calls so far. Mornings are always kind of slow. I tend to study in the downtime. Today I’m hungry though. Plus, my throats a little sore after that deep throating session. I grab a water and a bag of pretzels from the vending machine and snack on them while I wait for calls.

12:40pmA call comes just as I finish my snack. It’s from a guy I’ve seen a couple times. I call him K. He’s sweet but sort of shit in bed. I tell him to meet me at the usual place. I end the call with an “I’ll be waiting.” He likes that. 

1:10pm He knocks before entering, but doesn’t wait for me to come to the door. He’s impatient today. Interesting. I’m lying on the bed still. Dressed, but lazily so. He moves over to me immediately. He places the money on the nightstand without even looking over at it. It’s more than normal.

1:15pm He wants me to dominate him. It’s why he paid extra. Like an incentive to let him order off menu. I tell him I don’t have any toys. He doesn’t care. I tell him I’ll try.

1:20pm It takes a couple minutes to get going, but I can tell Ks enjoying this. I tell him he’s only worth what pleasure he can provide me. It seems to motivate him to take his time a bit more as he pounds into me. I don’t give him much time to do that though. It’s too much power for him. I flip him over and ride him. I tell him I’ll just have to do it myself and he almost cums right then. 

1:40pm He lasted longer than I expected, but I still got him. He didn’t stand a chance. Maybe I’m good at this whole dominatrix thing. Maybe I should add that to the menu. Either way, I made double for that session and Ks already out the door.

2:05pm Another call comes in while I’m watching a bit of daytime TV. Another new guy. I tell him where I’ll be. He tells me to get naked before he arrives. He wants it quick. Says he doesn’t have time for games. 

2:15pm He’s already knocking on the door. I guess he really is in a hurry. I open it and he almost touches me before he shows me the cash – I stop him and it’s like he growls when I do. “You must pay first”. He does. 

2:20pm He’s in me and getting close. It’s like the dude jacked off in the car and was just looking for a warm hole to cum inside. Unfortunately, I don’t offer that kind of service. So condom it is.

2:25pm He’s already dressed and heading for the door. I contemplate if I have time for one more client before I leave for the day. I decide to wait 30 more minutes before calling it. 

2:50pm No more calls, so time to head on home. I get fully dressed after taking a second to clean up, grab the cash and stuff it in my bra. I take the keys and lock up as I leave. Once I get in the car, I immediately roll the windows down. The hotel room always feels so stuffy. It’s nice to feel the wind in my hair for a bit.

3:20pm I walk through the door and put my money in my purse. I toss off my soiled clothes and get them in the laundry.

3:30pm I’m in the shower. I know I showered this morning, but it’s nice to wash off the sweat. 

3:45pm It’s sweatpants and studying for the rest of the night. 

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