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.

I grabbed them and brought them with me onto the bed. I held them in my hand and started to jerk off. I stared at them and then it hit me: she had been wearing these day. I’d never once done this before or even thought about it, but I put them up to my nose and sniffed. I focused on the precise spot where her pussy would have touched. The smell was strong and distinct. I stroked even harder and kept sniffing. Before I knew it I released a bunch of cum all over my hand. I hadn’t cum that fast since being a teenager. I was almost out of breath. I quickly put them back on the hook. I felt like a pervert.

Later that night I found Andrea on the internet. She didn’t appear to have any social media, but on their mechanic website there was a picture of her standing next to Ron and a bunch of cars. She had on a skirt. Not the same skirt but similar enough. I zoomed in so I could only see her up close. Her body was tan. I stared at her legs. I started to jerk off. I ran into the bathroom and quickly grabbed her thong and held it to my nose. I smelled again where her pussy would have been, all while staring at her picture. The smell was intoxicating and before I knew it I came again, quickly.

And this was my week. Twice a day I had done this exact thing. I had smelled them so much that by the following weekend the smell was barely there. Each time after I came I felt ashamed, but my level of horniness and obsession was overwhelming.

On Monday I had came back to the house from a run and saw a text from Andrea. It read: “jeep is ready. Pick you up around 2 today?”

I wrote back yes and waited around. I can’t lie…a few hours before she got to my house I jerked off again. I couldn’t help myself.

She pulled up around 2 and came to my door. When I answered she didn’t disappoint. She had on tight black leggings and a white tank top.

“Hey. I’m all ready.”

“Good – can I use your bathroom? I have to piss so fuckin’ bad.”

“Yes, of course. There’s a bathroom over there and one off of the guest room as you know.”

She walked toward the guest room. “I’ll use this one because I think I left something behind last time I was here.”

Oh shit. I hadn’t even thought that maybe she’d remember or figure it out. Where did I leave them??

Fortunately for me, she came out and didn’t mention it. I saw them in her hand, however.

She drove me back to get my jeep. We didn’t talk at all because the entire time she was on a call with a customer. Occasionally I glanced over and took in images of her hot body.

When we got to the place Ron had the jeep parked out front and ready to go. I didn’t seen him anyplace. I followed Andrea up the stairs and into her kitchen. I wrote her a check and she handed me the keys.

“Well, thanks for driving me and doing all this work!”

I then waved and started to walk out, as was still on the phone. She then put the away from her mouth and said “sit down. I’m almost finished.”

I sat down and waited. After she hung up she turned to me.

“Did you forget something? One hundred. Venmo is fine. “. I had truly forgotten.

“Oh of course. I’ll do that now.” I pulled out my phone and began the transaction.

“Add another $100, too.”

Before thinking I said “what? It was $100 last time!”

“John. My underwear was on that bed. Next to a box of tissues. You want to smell my pussy the you’re gonna pay me.”

I blushed harder than ever. I could feel heat radiating from my face. I was about to tell her I hadn’t touched them but there was no getting out of this.

“Ok. Umm…yes….ok…200 I’ll send it now. Ok. Ummm.” I was flustered and was half out of my seat.

“John, sit down and fuckin’ chill. I want to ask you something.”

I stared at my phone, not really doing anything but I didn’t want to look her in the eye.

“John grow up. Look at me.” I looked up. She had a slight grin.

“I don’t care about any of that. What I want to know is whether you want another pair before you leave. Just venmo me $300 total if you do.”

“Uhhh ok.” I sent 300 and within seconds her phone beeped. She looked at it.

“Good boy.” She stood up and took her flip flops off. Then, to my great surprise, she pulled her leggings down and off. She then slowly pulled her pink thong off. Her pussy was….very hair. I had actually not seen a hairy before. I could feel myself starting to get hard. She then handed me her thong and pulled her leggings back up.

“Here you go sweetie. Call us again if you need more work on that jeep.” Then she turned and started doing some kind of paper work.

I turned, still blushing, and walked out. Her thong felt very warm in my hand. And also a little damp. I got to my jeep and started to smile thinking about how much I was going to enjoy smelling them when I suddenly heard Ron behind me. I turned around.

“All set? Got what you needed huh?” He looked down at the pink thong. “Her pussy smells good, don’t it?”

“Uhh….” I wasn’t sure what to say. I just stared at him blankly.

“Get the fuck out of here. Fucking pervert.” Then he turned and walked back into the garage. My heart was racing fast and I quickly jumped into my jeep and drove home.

That had scared me but once I got on the road I didn’t care. I’d never go back there again. By the time I got home I was no longer scared…I was horny. I raced into my room and quickly pulled down my pants. I shoved her pink thong into my face and sniffed as hard as I could. It was amazing. It was so strong and it was damp…probably some sweat and her pussy. I came in about 2 minutes. And then my phone beeped. It was Andrea.

Her text read: “hey sweetie. Did you get home ok? I want you to take me out this Friday. Yes?”

I replied: “sure…but that guy Ron seemed like he wanted to beat me up. I don’t want any trouble.”

“He’s not going to touch you I promise. And he knows we are going out. Text me on Thursday and I’ll let you know where we are going.”

And that was that. The week went by slowly. I was a little nervous but I figured why not? I had dated so many women my age and very different…maybe it was time for a change.

And as it turned out, she was indeed a bit different. I checked in with her on Thursday and she wrote back: “Decided I want to cook for you. Just meet me at my place. My actual living space is out in the back in the guest house.”

I asked if Ron was going to be there but she said no, and not to worry about him anyway.

So that Friday I put on some nice clothes and went over. I regretted wearing something nice since she hadn’t dressed up at all. In walked in after she yelled for me to enter and she was wearing basically pajama pants, a t-shirt, and had a cigarette hanging out of her mouth. She was drinking some kind of mixed drink. Her ass looked amazing in her pink and white pajama pants. Her tits were practically bursting out of her shirt.

She walked over and gave me a kiss on the cheek. “Hey sweetie. I’m glad you came.” She handed me a drink and sat down. It was good…just a rum and coke. “Want a smoke?”

“I cigarette? I don’t smoke.”

“Ya a cigarette,” she laughed. “You ain’t stuck up are you? Rich people like you like to get on their high horses.”

“No, not at all… I mean I’ve smoked some jn college but that’s it.”

“Oh college boy. I figured. Here, let’s play some cards while we wait. I cooked meatloaf but it’s in the oven.” I thought that was a weird meal in the summer but whatever.

I can’t lie, it was fun playing cards and drinking with her. I’d never been on a date like that. After about an hour she prepared us each a late and we ate it up. It was really good. No salad, but overall it was tasty. We then went back to drinking and playing cards.

“Sure you don’t want a smoke? They’re so good after a meal…and when you’re drinking.”

“Ha, I’m ok. I think I’ll have another drink though.” I made myself one and one for her. I was starting to feel drunk….and good…and horny. She must have sensed it because she asked if I wanted to stop playing and watch a movie.

So we moved to her living room on the couch. It was basically all a kind of in-law apartment. Maybe Ron was a cousin or something. Just like the big house, the place was really clean but still seemed dirty because it was just old and poor looking.

We sat on the couch and she put in a dvd. Didn’t seem like she had any streaming services. As we watched I noticed she sat very close to me, and then placed her hand on my leg. I felt my dick move. Not even 5 minutes into the movie she out her drink down and started making out with me. She smelled like rum and cigarettes but despite that she was an amazing kisser, and very aggressive. She would lightly night my tongue and lips, and shoved her tongue into me so hard I almost gagged, all the while her hand creeping around my groin area.

Her hand then moved up over my dick and started stroking it through my pants. She really stroked hard and fast. I tried hard not to cum and even tried slowly moving her hand away but she slapped it away and grabbed my dick hard and kept going. I let out a moan and felt like I was just about to cum when she completely stopped.

“Not yet. You’re gonna do something for me. Go get your phone and put it down on the coffee table.”

That’s weird, I thought. I did it and then she pulled down my pants and boxers, then basically pushed me back down on the couch.

“That’s your cock huh?” And then she laughed. I wasn’t sure what to do but before I could respond she dropped her pants and underwear. She grabbed my head and pushed it to her pussy. It was even hairier than I remembered. She didn’t trim at all. It was dark brown, practically black, and covered not only her entire pussy but ran down around her inside thighs. She shaved her legs but didn’t go all the way up.

“Lick my clit.” I dove into her bush and found her clit. It didn’t smell like she has showered that day but didn’t smell terrible. It didn’t matter because I was so horny and she tasted good. She pressed my face into her even harder. I had trouble breathing but could hear her starting to moan.

“Grab your little dick!” I grabbed my dick. I had never in my life had a girl say my dick was little, but I had also never heard anyone say it was big. It was at that money that for a brief few seconds I realized that i DID have a small dick. I started stroking it and licked harder as she moaned…when suddenly she pushed my head away and looked down at me.

“Do you want to cum??”

“Yes!!” I said.

“Grab your phone. Venmo me $300!”

“What??” What the hell? Was she a prostitute?

Then she bent down and grabbed my neck. Hard. “Look you little rich prick. I want your money and you want to cum. Pay me the fucking money!!”

I got on my phone and sent it. The second she heard her phone beep she yanked my head onto her bush. My mouth was full of her hair. I stroked faster and she began to moan louder. I suddenly exploded with cum, all over my hands and on pants. I stopped licking and started to move away when she grabbed me and shoved me back to her pussy.

“Where are you going? I want to cum! “. So I licked and licked. Her moans grew louder.

“Ohhhh yes! Goood boy, keep going! Ahhh yes yes yes, ohhhhhh!” Her legs started to shake and I felt some of her hot juices dribble down my cheek. She pushed my head away and grabbed my face with both her hands. “God that felt good.”

We sat back in the couch and watched the movie. I felt weird about the money part and wished we had had actual sex, but her assertiveness was such a turn on. Eventually she suggested I stay over so not to drive drunk and we slept together in her room.

The next morning I woke up and she was awake staring at me. Her hand was on my dick and she was stroking it. It quickly became very hard.

“Morning.” She gave me a big smile.

“Morning! This is a nice treat. ”

“Yes it is isn’t it? I want you to cum for me. Can you do that for me? ”

“Yes! I will.” She reached over and grabbed her thong and suddenly shoved it into my face. I immediately recognized her strong pussy scent

“You like smelling pussy don’t you?”

I moaned and mumbled yes.

“I know you do…that’s because you’re a perv, aren’t you? But you love it. You jerk off to my thongs don’t you? Smelling my ass and my pussy. Do you want me to stop?”

I practically screamed, “no!!”

She suddenly got up and straddled me. My dick slid inside of her so easily. She must have had a wide pussy because it didn’t feel tight at all. I was surprised. But it still felt good. She started riding me and her tits in her tshirt bounced. Her thick bush rubbed against my stomach. She showed no signs of enjoying it but instead just stared at me and pushed her thong against my nose.

“Cum inside me, John. Come on! You can do this. I WANT your cum inside me. It’s safe John. Cum inside of me. Come on. I can’t even feel you but I bet I’ll feel that hot cum.”

I thrusted my hips upwards. I placed my hands on her thighs and moaned. “Ahhh!” I came inside of her. She pulled away the thong and as she got off my she wiped herself with it, until all my cum was wiped up. Then she handed it to me.

“Here. Take this with you. Consider it a gift.”

I left and when I got home I showed and took a nap. The whole night had just felt…weird. But when I woke up I had a raging hard on. I grabbed the panties she gave me and shoved my face into them. I jerked fast and hard and I came under 2 minutes.

The next morning I woke up to a text from Andrea. She wanted me to come over again Saturday night. I agreed. I wasn’t sure what I was getting into, but I wanted it.

 

To Be Continued…

 

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