This email showed up in my inbox this morning, so I wanted to put it out there. I’ll add my thoughts at the end, but I’ll let you read what I got first:
(Note that I have only very lightly edited the email for clarity. I haven’t changed grammar or spelling, and if you only knew how much I hate being called Theresa, you’ll know how hard I fought the temptation.)
Subject: Date with an Escort
Hey Theresa,
Hope you’re good. I’ve got to share this with someone who’d get it. It’s not the usual type I see you write about, so was wondering what you think.
Thing are a bit rocky at home and I’m not having any luck on AM lately. It’s been six months since I’ve been with someone, and Well, I found myself doing something I never thought I would. Ended up on this site, Leolist, just browsing the escorts and the pics.
I was looking at 40+ ladies — my kids are almost in there 30s so not going there, and MILFs, right? lol.
I kept going back to this on lady, beautiful pics, blonde, blue eyes, hourglass figure. She said she was 51. I was super nervous, but I got her contact info off the site and sent her an email. I felt like a kid. And then I sent text, lol. I didn’t know wtf I was doing. I was horny that night and just wanted someone. If we could have met then…
The earliest she could do was the Weds late afternoon, so I had a few days to cool my jets, but thought why not meet up? I could wait. I must have looked at her pics 1000 times I wanted her so badly.
We chatted a bit. I told her about myself and situation. I told her about my hight/weight and body shape — could lose a few pounds but not dad bod and offered pics.
All I could think about was this poor woman waiting for a guy she’d never seen come over, only to have some fat sweaty dude standing there with a dopey grin on his face. I’m not that great looking, but wanted to put her at ease I guess. She was pretty cool about it all. She didn’t share much, but it felt weirdly normal.
So I drove over to her place. I left work early for our 3:30 “date”. I did a street view of her place on google, and then drove past 10 mins early to see where she was. I didn’t want to screw up and knock on the wrong door. I parked up the road. What struck me was it just a regular house in the suburbs. Nice front yard, steps done up. From the outside, you’d never guess.
Man, was I nervous! Heart racing a bit — the whole deal. I texted that I was there and she told me where to park. When I pulled up I thought fuck it, act normal, and walk over like a boss without a care in the world.
She made it easy for me. When she opened the door, there was this big smile and it was just so genuine, you know? She was wearing an open silky robe and black bra, panties and garter belt. She was so HOT.
She took me into the kitchen, gave me glass of water, and we started chatting. I really wanted to feel her body. It had been so long
Place was neat, and very homey. She’s got good taste. I figured she had kids and I noticed a couple college and university diplomas on the wall. I didn’t ask but it was clear she was super proud of them. Like everyone else, she was doing this for them. That was my thought, anyway, and by the looks of her house, she’d done well by them.
I’m really turned on by sexy moms, and she was all that, for sure.
We just hung out chatting for 15–20. I know it sounds weird, but it felt like catching up with a friend. She was very sweet.
Now, there was this moment, right? I felt I had to say it. So, I told her, “I know I paid and all, but that doesn’t mean I think I own you or anything.”
I needed to know there was consent, beyond the money. She smiled. I guess all the newbies have some sort of reaction, but for me it felt good to clear the air.
We went up stairs, and while I’ll spare the details, she took good care of me. Some nerves returned lol. She’s a very sexy and sexual woman. I told her I didn’t want her to fake anything. I said I’d rather have sex with a dead fish if that’s all I was doing for her, then having her fake stuff for me.
Well, either she’s a Day Time Emmy Award level actress, or I made her feel good lol. I’m sure it’s a bit of both, because I’m not mr stud by any stretch, but it felt like she was into it. I know I was. Damn she was hot.
Time flew by. We laughed, shared a couple stories, and before I knew it, it was time to head out. The hour went fast.
Leaving her place, there was this sense of calm I hadn’t felt in a long time. Felt lighter, happier. Shot her a text later in the day just saying thanks. Told her I’d be down to meet up again sometime. She’s just… easy to talk to.
So why am I telling you all this? Guess I wanted to share how sometimes the most unexpected people can give us a gift. I didn’ know what to expect, but she everything I was looking for.
I wondered if I’d feel dirty or whatever, paying for sex, or if I was degrading her doing it, but I didn’t feel any of that. It felt so different. Warm and welcoming. She was a total professional and I have nothing to compare her to, but she’s got to be one of the best. I got the feeling that she cared about her work in the way few people do.
Where cheating is concerned, she was a bit more expensive than a hotel date with an AM lady, but the sex? So much better. I’ll see her again time and money permitting.
Life’s full of surprises, and for me, how she connected with me and put me at ease was one.
If you think others might find this interesting or helpful, go ahead and share. Just keep my name out of it, lol!
later,
[Name withheld ❤️]
I don’t know much about escorts, but I heard a radio show once where this guy in Toronto would interview random people on the street for a public radio station. I listened to it on my morning drive into the city. One morning he was at a subway station and ended up talking to a lady who was an escort.
She’d been doing it for years, and as I recall, she was in her early 30s. I was a little more prim and proper in those days, but still open-minded. What she said, though, blew me away.
She said she liked her work.
I couldn’t believe it. I supposed I’d always thought about trafficked girls and women or those forced into sex work by circumstance. I’d never heard someone say the liked it. Not like that. I never thought it possible, to be honest.
What she said went something like this —
There are people who can’t, for whatever reason, have normal sexual contact with others. They might have a skin condition or be disfigured, or whatever, so not only have challenges but go without physical touch because of it. When I work with them, I see beyond that, to bring them something we all deserve. Physical, sexual satisfaction in a non-judgmental way. I love my work, the money is good, and I get to help people. How many people can say that?
I get to help people. I started cheating because I know that loneliness. I was deprived of physical touch, and it gnaws away at your soul. To think that there are people out there to do this for people who otherwise wouldn’t be touched was heartwarming to think about.
That woman changed a lot of my thinking on sex work. It’s definitely a dangerous job, but it opened my eyes to the idea there were people who liked it, were good at it, and like the lady mentioned in the email, who used it to support their families.
When you step back and realize we only get one trip here, what you make of it becomes all the more important.
Messaging Support App for Men!
MSG HER NOW is a dating support app for men that uses the power of ai to write perfect opening messages and dating profiles she’ll love! MSG HER NOW will write the perfect opening message designed to get her attention.
Download today from the App Store!
Msg Her Now is the ultimate dating app messaging tool to help you start conversations with the ladies you’re…apps.apple.com
Married dating support for men!
Would you like me to get you started on your path to depravity? Follow this third-party link to my products and services ⇨ PRODUCTS & SERVICES!
Join my email list!
Get a free pdf copy of my ebook — How to Cheat: Field Notes from an Adulteress — by joining my list! Third-party link to ⇨ MY EMAIL LIST!
© Teresa J. Conway, 2023