I’m 30 years old, and I have been a high-end escort for 3 years now. This diary is from the first time I ever saw a “client”, and about how I changed my life around from a broke drop-out party girl to a well-off experienced, sexual woman.
4:30pm. The Friday night bartending shift is a fun one. My little dive hole is woefully silent during the week, but comes alive on the weekends. I’m here preparing for the fun.
5pm. Crowds come earlier on Saturday. Already I’m making drinks and flirting with the customers.
5:30pm. I’m tipped a $20, and I make sure I lean forward a little more when I snatch the bill from his fingers. My DD-cups are perfectly plump on my 5’5 body and help balance out my thick ass.
7pm. The drink orders come like crazy. It’s me and two college students I hired behind the bar tonight. I bump into D, the older of the two, and he drops a vodka bottle. It breaks. I curse loudly.
8:30pm. It won’t be winding down for several more hours, but I slip away into the office for a breather. I ignore the bills littering my desk. Buying a bar suddenly after dropping out of business school was stupid. I financed that stupidity with basically all kind of debt that I could possibly get. Business school and college debt isn’t going anywhere too…
10pm. A lull in the rush. Most people are enjoying the live music, and there is a slow moment at the bar. I start to chat with one of the older gentleman seated there, and he asks me a lot of personal questions.
2:45am. Last call was 30 minutes ago, but Curious Guy is still seated there… staring. I ask if he would kindly leave.
3am. As he starts to get up from his seat, he turns and slaps two crisp hundred dollar bills on the counter. My eyebrow raises. “Come home with me.” My jaw goes slack.
4am. Back at his shitty apartment, I take off my tight clothes for him, my tits barely held in the black bra I wore. I let down my blonde ponytail and ask what he wants me to do.
4:15am. I’m sucking his dick and he seems to like it. Tells me to slow down, so I do, and he pushes me off suddenly. “Flip over,” He grunted.
4:30am. Now he’s fucking me right there on the floor next to the door.
4:40am. I can tell he’s trying not to cum because he slides out and makes me suck him off again, slowly.
4:45am. He came on my face.
1pm. I wake up with $200 + tips from last night. Feels good to get paid for what you love to do.
3:30pm. Saturday’s are even busier, so I’m back at work early preparing.
11pm. A cute guy orders a pretty girly cocktail, but I don’t see a girlfriend nearby.
1am. It’s starting to quiet down finally. I’m exhausted, sweaty, and red-faced.
1:30am. Cute Guy is back, asking for the same drink. I give him an extra shot and wink. He strikes up a conversation.
2am. Last call.
2:10am. “What will it take for you to take me to your place tonight?” Cute guy asks, but I know he hasn’t been tipping very well.
2:15am. “Hmmm… $400 and I’m yours for the night”, my flirty answer. I expect him to laugh it off. “Deal”. Not exactly the kind of deals a once MBA-hopeful expected to clinch.
3am. Back at my place, I let Cute Guy in, and accept my payment before we get down to it. He immediately asks to eat me out and I oblige.
3:10am. A few minutes later, we proceed to 69 and Cute Guy is still as eager to put his tongue as deep as possible in all of my holes. He orders me to stroke faster and asks to cum in my mouth. But there is a twist. Once he is done, he wants us to ”split the cum” . Lets see.
3:12am. He cums hard in my mouth. He no longer wants to split …
3:30am. We took a shower together and talk about life.
5:30am. I can’t sleep with a stranger in my bed, so I’m sitting on my couch….. Realizing I just figured out how to pay off my debt.