After about four years of, let’s be honest, a mid-life crisis, my days of using escorts have recently come to a natural end. I’m moving onto a new, exciting time in my life that simply doesn’t involve them. I have no regrets, and reflecting on the end of this era is making me think of the girls I’ve seen.
Keep in mind, when I say girl, I always mean woman. I don’t call all women girls, it’s infantilizing. And these were definitely all women. But calling someone an escort can make it sound like they’re aloof. And calling someone a hooker somehow strikes me as deliberately mean, even when it’s not intended that way. I’ve always fallen back to call girls, a phrase I’ve loved since reading old detective novels. It’s a little old-fashioned, so I always just call them ‘girls.’
The first time I saw someone, it was almost on a whim. I just happened to be leaving on a four day trip to a hobby convention the next day, and was looking at some porn. An ad for an escort guide popped up, and a lightbulb went off. I had about $1000 budgeted for spending money for the weekend, and my wife and I had recently talked about how I could try and see someone outside of our marriage. I’d never considered paying for it, but what the hell? The stars just aligned.
So I looked at the listings for the big city I was driving through on my way to the convention, and found this girl. Now, my wife is gorgeous, but in a very specific way. My wife is that sexy midwestern type, curvy with strong shoulders and big tits, and a tooth crooked from when her high school best friend punched her after finding her blowing her boyfriend. That type.
So I was looking for something different, and I found it. I have always, always had a thing for women with tattoos. The more the better. There is just something supremely sensual about a woman so comfortable with their own skin, with their appearance, that they are sure about what they want to be, that they want to indelibly alter themselves to be closer to their own perfect self-image. That drives me wild.
The girl I found had a lot of tattoos, she was cute, and lithe, and had dyed pink hair. I love dyed hair, for similar reasons to why I love tattoos. So I reached out to her and asked if I could see her the next day, on my way out of town. She said yes, and we made plans to meet at a Starbucks near her place.
When I got there the next day, she texted to say she was running a few minutes late. She asked if I could buy her a coffee and grab a seat. When she showed up, she was very distinctive, and she lit up when she saw me; I had sent a verification selfie, so she recognized me, but she told me later that she say my eyes light up when I saw her, and that’s what she was reacting to.
She sat down, took her coffee, and we chatted for a while. I told her this was my first time doing this, and that I loved her ink. I clearly didn’t come across as a psycho, because she asked if I wanted to head back to her place, and I eagerly agreed. She didn’t offer to pay for her own coffee, which I though was a cute power move, and actually kind of sexy.
We got back to her place, and into her bedroom. It was exactly what I’d imagined a hooker’s apartment would be like, and nothing like it. There were black shag blankets on the bed, and lube and condoms on the bedside table. And her tennis trophies on the bookshelf and a bunch of bananas on her dresser, next to a copy of Infinite Jest.
She knew this was my first time, so she actually undressed me standing up, running her hands up and down my chest. When she unbuckled my belt and slid her hand onto my cock, she stood on her tiptoes and breathed “Oh, that’s a nice cock,” into my ear. I believed her. I am blessed with a pretty great dick, not terribly long 6″, but very thick. Thick enough that a friend in high school once glanced over at me in the urinal and practically did a double take, then ran out to tell everyone in the hall that he could find that I had the thickest dick he’d ever seen.
She went down on me for a while, and then we moved to the bed, and we tried to fuck, but I couldn’t. I couldn’t get any traction on that shag blanket, I hadn’t worn a condom in nearly 16 years, and to be honest, her pictures had made it seem like she had bigger boobs, Bs, but in person, they were As, and that was not really my type.
So it didn’t happen. She was disappointed, and told me I was a good guy, and that she’d love the chance to try again. I sighed and thanked her kind of half-heartedly. As I walked to my car, she walked with me, smoking a cigarette. When I got into my car, she gave me a hug and said “I mean it, I’d love to see you again.” I thanked her again, hugged her, and drove off to my convention.
Over the weekend, I had a great time, as I always do, and thought about my experience. It wasn’t bad, but it wasn’t great, and I know for a fact that sex can be great with someone you love or someone you’ve just met. I decided that it was first time jitters, and that my spending budget for the weekend could go a bit over. So on Sunday, just before I began the three-hour drive home, I texted to ask if I could see her again on my way back through. She was happy to, and told me to just come by her place when I got there.
I arrived, and texted her, and she came to let me in. She gave me a huge hug.
“I didn’t think I’d see you again! I’m so glad you’re here.” She led me into her apartment, but instead of her bedroom, she led me to the laundry room. There was a futon in there, and linoleum floors.
“Sorry,” she said. “My room’s kind of a mess right now, so we’ve got to do it in here.” I felt a little weird about it, but I was agreeable enough and said okay.
She slid my pants off and sat me down on the futon, pushing me back and pulling off her top. She squatted down in between my legs in a pair of pink and black panties and started to go down on me. This was entirely different than the first time. She took her time, working her way up and down my shaft, running her tongue in a circle around my cock every time she came up, then lowering herself down slowly, as deep as she could. She wasn’t deepthroating my entire cock, but she was getting as much of it as she could each time, occasionally gagging, then coming up for air before diving down on it again.
It was amazing, and it was then I noticed that while she was doing this, and one hand was stroking the base of my cock that she couldn’t get her mouth to, her other hand was inside her panties, her own fingers stuffed inside her. I leaned forward, over her, and grabbed her ass, squeezing, while she pressed her face even further onto my cock.
She came up for air, and spoke for the first time since she starting blowing me. “Force my head down on your cock.” No one had ever asked me for that, and I felt every part of my brain light up at once. I grabbed her hair and pushed it down on me. I heard her mutter around my dick, I couldn’t make out the words, but it was “yes,” or “more,” or some other primal noise.
This continued for as long as I could stand. She’d come up for air, and have barely enough time to inhale and breathe “Harder” to me, before I was forcing her down on me again. All the while, she’s fingering herself deeper, and deeper, squirming and moving her legs as if to find some perfect angle for her fingers.
Finally, she stopped blowing me and growled at me. “I want your cum on my face.” She leaned back, now furiously rubbing her clit back and forth. “Shoot your load on me, I fucking need it.” My cock was absolutely rock hard looking down at her, and I saw her gasp as she started to squirt, soaking her panties and coating the linoleum floor in her juices. I immediately came, as hard as I ever have, shooting all over her face, five or six spurts of jizz on her cheeks, chin, mouth and forehead. She rolled her neck, making the cum run across her face, then leaned forward, so it dripped down onto her chest. As I collapsed back onto the futon, she gave herself one more orgasm, leaning forward, pressing her cum-covered face into my crotch. I felt her body shudder against my legs as she grunted into the hair at the base of my cock.
At last, she collapsed on top of me on the futon. We were both gasping. When we caught our breaths, I said “Your room is perfectly clean, isn’t it?”
She grinned. “I can mop the floor in here.”
We hung out like that for a few minutes, talking about our weekends. I told her a bit about my convention, and she complained that someone had stolen her cell phone on Friday, and she was lucky she’d gotten it replaced on Sunday morning, otherwise she’d have missed my text.
She got up to clean up and get me a towel, and I said how amazing this time was. Almost entirely naked, covered in cum with a pair of soaking wet panties, she looked back at me, shot me a finger gun and the click-click sound dads usually use. With a drop of my jizz dangling from her eyebrow, she winked and smiled, and said “Yeah, I got your fucking number.”
As I left, she came out to smoke a cigarette and walk me to the car again. This time, her hug was huge and affectionate. Then she looked at her phone said “Oh, shit, I’ve got another appointment! I squeezed you in, hope you don’t mind!” Of course not, I said, and she ran off, her house slippers flapping against the concrete.
I turned to walk back to my car, but after a moment, I heard her running up behind me, the slipped slapping concrete. Before I can turn, she grabs my ass, one cheek in each hand, squeezes, and stands up on her tiptoes to growl in my ear. Then she ran away again, yelling back, “Okay, I really do have to go. Bye!”
I was hooked. And I never cared about a woman’s cup size again.
Source: reddit.com/r/gonewildstories/comments/iwgyvt/the_girls_ive_seen_the_first_girl_mf