**This will be a new series, and I'd like to dedicate it to all the good submissives and doms who supported me last series and wrote me feedback. What a lovely community!
My name is John and became very fortunate at a young age. I had never planned to become wealthy but my father, who I barely knew, suddenly died when I was 30 and left me with all his assets. I wasn't super wealthy, but I had enough money to never have to work again and live well. The problem was that I couldn't find a partner that really worked for me. I was a decent looking guy, so that factor coupled with my financial status allowed me to date hot women on a regular basis... and I even had some longer term relationships. The issue is that they all had one thing in common: they were all semi submissive. Not in the kinky sense, but in the normal vanilla ways.
I discovered when I was in my mid twenties that I wanted to be dominated. I was still inexperienced so I didn't know exactly how, but I had briefly dated a woman on a visa from Germany. She was hot and unbelievably dominant. Nothing I had ever experienced in the US. She hadn't even don't anything that kinky, but after she had gone back to her home - I never saw her again - i started reflecting on things she would say when I was masturbating. Things like "that's a good little puppy," or "you'll be a good servant to me one day," or "you need a strong woman in your life because you are weak." During the relationship I actually found these very annoying, but after she left and I had time think about it, I started to realize just how much it turned me on. And then I started watching and reading submissive type content and I was hooked. I realized I was naturally a submissive...and that was why I had such trouble finding a good dominant partner.
It's not as easy to find as some people think. The pattern became obvious after awhile: I'd find a woman I was attracted to and after a few times having sex we'd inevitably talk about what we liked in the bedroom. As soon as I began saying how I really liked a dominant woman they'd back away. Occasionally they'd pretend to get into it, but the most they'd do is just get on top and use a sort of fake voice with me to seem in control. Some were pretty good at it; the problem was that even when they complied it was just an act. What I needed was a true dominant woman, and I'd find one in the least obvious place....and definitely nothing like I had expected.
At the time I drove a jeep Cherokee. Nothing fancy but a car I really enjoyed. Yes, I had money, but I didn't care to flaunt it. Oh, and one more thing: I had enough money to not work for the rest of my life, but in order for that to work I needed to be on a budget. So I treated every months allotment like a paycheck. Hence, the same old Jeep I had when I inherited all the money. I had found an old rundown mechanic that was on the outskirts of the small city I had been living in. The first time I drove up to it I almost just turned away: it looked like an old junk yard, surrounded by thick trees in a very rural area. But, I decided to give it a try; my previous mechanic was very good but had closed shop, and he had recommended this place.
I drove in and a tall, muscular guy who looked to be about 50 came out and met me. He was covered in tattoos but seemed nice enough. He introduced himself as Ron. A recently lit cigarette hung from his mouth. After we shook hands I described my issue and he took a look.
"Sorry to say this buddy, but you need a new transmission. This jeep ain't that old, so it might still be under warranty. Happy to do it for ya. Lucky you even made it out here from the city."
I called and discovered that my warranty had just expired. I sat there thinking while he waited for my answer. It's hard to explain but that car had meant a lot to me for sentimental purposes, so I decided to just get it done.
"Ok," I said. "Let's do it."
"Great. Andrea does all the paperwork. Shes up in the office if you want to walk up and get things situated." He pointed to the front of his house beside the junky garage. It was a small blue house that looked like it hadn't been well taken care of. These people seemed poor and a bit like "hicks" but nice enough. I walked up to the house. The "office" it turned out, was just their kitchen.
I walked in and saw a woman sitting at a kitchen table. She was doing some sort of paper work with - you guessed it - a cigarette hanging out of her mouth. As my mind was quickly judging her, she suddenly turned toward me and I realized she was actually pretty attractive. She had a few tattoos but her skin was very tone and tan. She had nice sized breasts and was wearing a tank top so I could see a lot of nice cleavage. She had dark brown hair that went down a little past her shoulders, and she was wearing a cotton type skirt. In summary, she was really hot. She was probably between 40 and 45. It was the first time I had truly found myself attracted to a woman 10-15 years older than me
"Did Ron send you in?"
"Yes ma'am.m," I said rather jokingly.
"Ma'am?? I like that. Nice to see a boy with manners. Now, what did Ron say you needed?"
I handed her the paper Ron had given me. She put out her cigarette and read it, then wrote out some sort of contract. I looked around the kitchen. It wasn't dirty in that they lived like pigs, in fact it was clean. It just LOOKED dirt because they clearly didn't have a lot of money. Appliances were old. Everything was old. Their fridge looked like the one my grandmother had from the 70s.
She handed me the contact and I signed it.
"Won't be ready into next week at the earliest. Not our fault, it's just that some of the parts aint gettin' here 'til then." She lit up a cigarette as she waited for my response.
It was strange to hear her talk like that and yet look so hot. It occurred to me that she probably had a rough life.
"Ok that's makes sense. Uhhh....i have a little problem though. I don't have a way to get home. Will Uber or taxis come out here?"
"'Nope. And our one borrow car is out with another customer. But I guess I could give you a ride since you're paying us for such a big job. Want me to drive you in?"
"Sure. I feel bad though, are you sure?"
"Oh, I'm sure. And don't feel bad, you're going to give me some money for doing it."
I sort of half laughed but she just stared at me with a straight face. "You can afford it." She grabbed her cell phone and keys and we headed outside. We walked to her car, which was an old rusty Toyota Corolla. We got in and the doors squeaked. After starting it we drove off.
It was about a 20 min drive to my place. While we drove I glanced over at her body. Her skirt rode up high exposing her thighs. They looked very tone and tan. I was noticing that she wasn't wearing a wedding ring, and wondering what her relationship was to Ron when suddenly she said "like what you see??"
I couldn't believe it. "Oh my god, I'm sorry, I was...uhh...just noticing ...."
She laughed. "I'm just fucking with you John. It's ok."
I'd never had a woman call me out like that. I wonder how many other women actually noticed when I was checking them out?
We finally arrived at my suburban home. As soon as we pulled into the driveway she gasped.
"Are you fucking kidding me? This is all yours?"
Part of me inheritance was a large house. It was on a busy but wealthy street. It had a large pool that you could see from the driveway, and in general it just screamed RICH.
"Ya. It is!" I was about to tell her I had inherited it, but I wanted to impress her. She asked what I did and I lied and told her I worked as a financial advisor. The truth was that I didn't work at all.
"And that's your pool??"
"It is! You can take a dip if you want!" I jokingly said.
"Fuck ya! I have an extra pair of shorts in here. I'd love to just dip my legs in."
"Uhh sure, let's do it." I thought it was weird but why not? Plus it was at least 85 degrees out.
We got out and walked into the house. She kept saying how nice it was. I showed her around and then where she could change--there was a guest room on the first floor. She came back out wearing the same top but instead of her skirt she had on what looked like some black running shorts. I opened the slider and she walked out ahead of me into the pool area. It was the first time I noticed her ass. It was very "bubbly" and pretty big but seemed super tight.
I sat in one of the chairs. She went in just up to her waste and lifted up her tank top so not to get wet. I could see she had a tight stomach as well. I watched as she walked around in the shallow.
"Ah this feels so good. It's been such a hot fuckin' summer and we just have that shitty pool in our yard that ain't even working this year. Ron said he's gonna buy a new one but we'll see."
"So, is he your....uhh....boyfriend or...."
"We just work together. I actually live out back in a little guest house. He does all the mechanical stuff and I do all the business side of things. We grew up younger. It was actually his father's business but after his father died he hired me to take care of all of that. It's a good deal."
Didn't seem like a good deal to me, given the dump they lived in, but who was I to judge?
"Alright, towel please." She said with such authority. Maybe because she saw me as younger? I grabbed a towel and handed it to her. As she dried herself, her cellphone rang and she answered it...talked for a minute and then hung up.
"Shit. I need to get back. More customers." She went in and changed back into her skirt. I walked her out to the front to her car where she lit up cigarette before hopping into the drivers seat. Her skirt rose up again. Damn she was hot.
"Hey," she looked up at me. "I want one hundred." I genuinely had no idea what she was talking about, and then I realized. For the ride.
"Oh...uhh... " I sort of laughed. $100 for a short fucking drive?
"One hundred." She held out her hand. I couldn't believe she was serious.
"Ok but I don't have any cash on me." She yanked her hand inside the car and looked annoyed.
"Venmo then. Here's my cell and here's my Venmo tag." She gave me all information.
"Thanks John." As I handed back her phone she grabbed it but also grabbed my hand and very subtly but intentionally rubbed it as she brought her phone towards it. I noticed she was checking out my groin area. I'd never seen a woman do it so blatantly. " When your jeep is done I'll come get you."
"Ok," I said and she drove off. As I walked into the house I realized I was hard. I think it was her touch. Or the way she talked to me. Or her legs with her skirt pulled up. Was I hard when she looked??
I went back into the house. I wanted to jerk off. I went into the guest room where Andrea had changed and flopped onto the bed and stared at the ceiling. She had made me so horny. I was trying to figure out why. I found cigarettes disgusting. I found tattoos a turn off. She was older. She seemed a bit uneducated. She swore like a sailor. But she had a hot body. But that wasn't it either. I'd been with lots of women with hot bodies. And then I figured it out. It was just the way she took charge. Or was assertive. The way she just demanded $100 for a simple drive in. And the way she called me out for checking her out. The way she demanded her towel.
I started to rub my dick. It was fully hard. I went into the guest room bathroom to grab some tissues in anticipation of cumming pretty quickly. As I was about to walk out I saw on the towel hook something that would change my life. Her panties were hanging. A black thong, to be exact.
