This is a story, based on real people, about some events that happened years ago. It's highly embellished and changes to some things were made to bring it in to this era. Like mobile phones for example, which didn't exist at the time. All the names have been changed. The only characters I actually had any sexual contact of any kind with were the ones referred to in this story as "Sherry" and "Shelly", their physical descriptions and the basics of the events described with them are reasonably accurate. All of the characters and relationships to each other are real. Any physical descriptions of the other characters which could reasonably be ascertained through normal clothing are accurate, and any description of sexual contact with the other characters is complete fiction.
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My story begins at a charity golf tournament. Let me tell you a little bit about myself at the time. I was 27 years old, and four years before, I had suffered an on the job injury in the factory where I worked. I was scheduled for surgery, but the day before the operation I got a letter from the factory saying I was fired. I called my brother in a panic. "Calm down. Open the phone book to the lawyers section".
That afternoon when I got home from the lawyer's office, my phone was ringing. And ringing. And ringing. When I finally answered, it was the man from HR at the factory. "Noooo, there's been a terrible mistake! You're not fired at all! You just have your surgery and take aaaallll the time you need"!
Yeah right. 6 months later, I was almost ready to go back to work. But I was broke. My landlord had been letting me slide with a promise, and that's the only reason I wasn't living in my car.
One day he knocked at my door. "I've got a deal for you"... and he did. He sold me the duplex I lived in and financed it himself, no payments due till I was back to work.
When the settlement came, I went to him to pay the place off. But he wouldn't take it. Instead he took me under his wing and showed me how to buy houses and rent them. So four years later, at the charity golf tournament, I was self-employed with over 30 rental units and doing quite well.
I was randomly paired with a guy named Doug. I'm a single digit handicap golfer. Doug was good, but not that good. We finished 3
rd
, and hung out for the payoff. That's when his wife walked in.
Sherry was a few inches shorter than my 5'10" with short brown hair, a little thick around the hips, and an absolutely fabulous 38 DD rack on her. We all chatted pleasantly for a bit. When Sherry heard I was a landlord, she was excited. "My sister needs an apartment! Do you have any vacancies?"
"I always have vacancies" I laughed, and pulled a card from my wallet. "Have her give me a call".
That Thursday, I was waiting in a vacant unit to show it to her sister. I hadn't yet had it cleaned, so there was still a ratty couch and some chairs in there when Sherry arrived before her sister. We made small talk for a little while. I was really starting to like her!
Well, a few minutes later, her sister breezed in. To make the long story short, she hated the place. I gave her a card for a friend who had some things that were a little more upscale, and she breezed back out.
"I'm so sorry I wasted your time" Sherry said sincerely.
"No, don't worry about that! It's the life of a landlord. I'll show a property 3 to 5 times usually before I get a tenant for it.
"Well, I still feel kind of bad. I knew how picky she was". She reached her arms out and gave me a friendly hug. A very friendly hug. As I pulled slowly away, her lips brushed my cheek gently. The next thing I knew, we were kissing passionately and shuffling over to the ratty old couch.
I don't know who pulled who down on to it, but in a minute her tight fitting satin shirt had fallen to the floor and I was struggling with the hooks on the back of her bra.
"Wait a sec" she whispered and reached her arms behind her back. "It's a sports bra. I like the way it holds me in."
The hooks gave way and she pulled her bra off and her 38DD tits literally sprung out.
I had never seen tits like that anywhere. Not in a magazine, not on TV, not even in a porno movie.
All natural, perfectly shaped, and topped with a perfectly round aureole and a rubbery nipple the size of a pencil eraser. My hands roamed freely over her breasts as we kissed. I had felt a lot of tits in my 29 years. Sherry's were easily the firmest I had ever felt, even firmer than women with much smaller breasts.
Her hand drifted to my crotch and squeezed my rapidly stiffening prick. My penis is circumcised and almost 10 inches long when fully erect. I'm told it gets longer in the minute before I cum, but I'm never thinking about that. But what made her come to her senses was my girth. I'm about as thick as a Red Bull can. And my cock was about to burst out of my pants.
"We shouldn't be doing this... I'm married" she said as she pulled away just a bit.
"Sherry, I'd never make you do anything you didn't want to. I promise I'll be gentle with you".
I had had more than one woman see the size of my dick and want to back out. I'd never want to hurt anyone, so I always let them, with a smile on my face.
"No... no... It's just that I'm not on birth control. I don't think I'm on my fertile time, but I shouldn't be taking chances like this"
We began to kiss again, and I guided her hand back to my rod as I ran my other hand up her thigh. She spread her legs just slightly, and when my hand reached her pussy a moan escaped from her mouth.
She was soaking wet.
I unbuttoned her pants and began to work them off.
"No...No she protested weakly. I had worked my shorts down and her soft hand was gliding slowly up and down my thick shaft.
"Do you have a condom" she whispered. I didn't.
"No Sherry but I'll pull out, I promise... I promise"
Normally for me this would be a lie. But there was something special about Sherry, and I knew if I didn't keep that promise I'd never be banging her again.
"Just let me pull out this time Sherry and I promise I'll always wear a rubber with you... I promise..,"
"I can't get pregnant" she whispered. I could tell her resolve was gone. She laid back on the couch and spread her legs just a little more, revealing her smooth shaved pussy.
"I'll pull out, I promise... I promise"
"You promise"? She said softly and spread her legs wide for me to mount her.
"I promise" I whispered as I rubbed the fat knob of my circumcised cock up and down her shiny wet slit and pushed gently. Her inner labia snapped over my glans and I began to sink my rock hard prick in to Sherry's pussy, an inch or two deeper with each stroke. Soon I was fully embedded in her. I began to thrust in and out with long smooth strokes as she wrapped her arms and legs around my back and rocked her hips gently.
"Oh honey... Oh honey" she gasped as I felt the walls of her silky vagina begin to spasm on my cock and a shattering orgasm swept over her.
30 minutes later, we were both soaked with sweat and Sherry's big firm tits were mashed against my chest. Sherry had had a series of powerful orgasms, how many I have no clue, and she began to have another one. As her pussy spasmed hard on my thick meaty rod, I felt the familiar tingling begin in the head of my dick.
I knew I wanted to be fucking this succulent young wife every chance I got, so I didn't dare break my promise. I quickly pulled my steaming cock from her vagina and stroked it rapidly, pointing it at her big firm tits. A few seconds later, the first spurt of hot semen burst from the tip and splattered on her belly and breasts. 6 or 7 big ropes blasted from my cock, and my balls were completely drained.
Sherry began to giggle. And I did too. I let her use my underwear to clean up and we got up and got dressed.
Sherry kissed me at the door. "I can't believe how good that was" she said, and I could tell by her face she meant it. "Next week"? She smiled.
"Next week"! I smiled right back. I drove home commando.
Five years later, my empire of rentals had grown to the point where it was just too much work. I turned it all over to a management company, and right away I wished I had done so two years earlier. All I do now is cash checks, play golf, and once a week, on Thursday when her husband stays late to do payroll, fuck Sherry silly. We fuck for two or three hours straight. She's still not on birth control, so we use condoms. But because my dick is so big and thick, once in a while one breaks. Last year I had to pay for an abortion for her.
I live in one of the duplexes I own, and my bedroom shares a wall with my neighbors, Jeff and Shelly. They are a very young and very pleasant Christian couple, and his dad is a prominent local fire and brimstone preacher.
Once a month or so I can clearly hear them having sex for about 10 minutes, even as quiet as they are. So even though it's always during the day, I know good and well at least Shelly has heard me fucking Sherry's brains out for two or three hours straight. Sherry's not a screamer, but she's plenty loud. And that heavy oak headboard bangs against the wall when I really start to slam my cock in to her!
One rare Saturday afternoon, Sherry appeared at the door.
"He's playing golf, we have an hour"! She bubbled, and we made a beeline for the bedroom.
Little did I know Jeff's dad was visiting.
When Sherry left, he "Happened" to be sitting on the porch swing. There was no way to miss the big diamond glinting in the sun from Sherry's wedding ring.
"Let me ask you a question, son" he said. "What are you going to do when you get to hell"?
"Mind your own business buddy" I growled and walked in to the house.
For the next week or two, Jeff and Shelly kinda avoided me.
A month or two later, I was supposed to meet Sherry at my house, but I was running a little late. I fired off a quick text to Sherry, and she texted back "NP we R sitting on the swing". About 20 minutes later I parked my truck and walked up the steps .Sherry and Shelly were sitting on the porch swing, talking and laughing. Sherry jumped up and hugged me. "Time to go"! She smiled and winked at Shelly.
"She's cute as bug" Sherry said.
"Yes she is" I replied.
"Would you fuck her?"
