The first white envelope
My name is Jake. Or at least it is to you. I’m an escort; at least I am at night and on weekends. I have a career that has nothing to do with sex. I don’t escort because I need the money but because it fills a space…
I posted a profile online, thinking I wouldn’t receive any hits. It was late, the posting was brief. I awoke to 15 emails.
My world began to spin, and I wondered if this was really happening. I wondered if this is what it felt like for every other young man who posted as well. Were there really that many men out there with the funds available to just have a boy at their disposal for a few hours a night? Apparently there were.
A lot of them message me, with the thought that they would enjoy paying a guy to show them a good time. But the digital interaction satisfies their desires while they stroke one out in front of their screen. They are heard from periodically, with the same types of messages where they describe their idea of a good time and how it involves you, your soft lips and sexual organs. Then the emails stop for a week or two.
Then there was Bill.
I had my first “date”. I prefer the word date over “appointment” perhaps to try and make it sound a little more like “Breakfast at Tiffany’s”. The date was set for 8 PM and Bill had booked for 3 hours, but the work began at 5 PM. First a workout to make everything a little more firm, then a shower to make everything a little more fresh. After that it was time to pack the big black bag of fun:
- 8” Dildo
- Douche Pump
- Condoms
- Lubricant
- Baby wipes
- Towels
Would I have enough condoms? Will he be ok with this lube? Hundreds of questions raced through my head. I like to be prepared…
Once the bag was packed, the hair and make up done, it was time to head out. From the time I left the comforts of my condo, I felt like everyone walking past me knew what I was about to do. They all knew I was off to some strangers home, to sex him up and take his money. I felt like everyone who made eye contact with me was judging me. I jumped onto the subway and hid in a corner until I made it to his stop.
I messaged him and he was on his way to the passenger pick up. I wondered, did anyone else here know what I was about to do? I worried, would I look like I was getting into a complete strangers car?
I got into his black, Lincoln SUV, he lit a cigarette and we chatted on the way to his home. Bill is older, early 50’s maybe. He lives with his 2 dogs, both affectionate as they are giant. We exchange brief life stories as I drink my water and he finishes another smoke. Finally it was time to head to the bedroom.
The room was lit with a single vanilla candle, furnished with a king size bed, and a 60 inch flat screen TV. The bed spread was polar fleece. Bill went to clean up and I set up my bag near by. While I waited for Bill to return all I could think about now was “Can I get it up?” He was old, and not my type. His hair was thinning and grey, his teeth yellowed from the chain smoking and cola.
Luckily he returned with a fresh minty mouth and we began the “date”. Bill has a talented mouth, he kisses well, and has some amazing technique when it comes to servicing a man’s cock. We kissed, sucked, and touched just about every part of each others body, until we both blew our loads across each others chest. Then for about an hour I gently massaged the rest of his body. There was no feelings of nervousness, or awkwardness. We both had just participated in adult sexual exchange and were now discussing the election results as the dogs curled up to us in the giant bed.
After cleaning-up and getting ready to go, Bill drove me back to the subway. There was a hand shake, and a mention of doing it again. Then came the “This is for you.” He pulled out a standard letter sized white envelope, sealed. I smiled, said thanks and stashed it in the side pocket on my duffel, hoping that no one would see. I closed the door of the SUV turned away and smiled.
It was the largest smile I have ever managed in my life. I had just completed the transaction. I put on my iPod and headed inside to catch my train. I smiled the whole way inside, paid my fare and headed down to the platform. It was empty, now 11 PM. I opened the envelope and quickly counted the 20’s twice. There were a lot of them.
I then stuffed the bills in my designer wallet and tossed the white envelope into the trash, jumped onto the subway car and sat there. This time not hiding, but instead sitting there with a proud smile on my face. That first white envelope made me realize that nothing is as it seems. We have no idea what is going on with each person we pass in the street each day, and we have no idea what each person is capable of.
The date wasn’t about the money. It was about the power. I am in demand. I am desirable. I am in control.
I am Jake…
…and this is what I do for more
