Fbailey story number 219

Older Women

When I turned sixteen my mother had her hands full with me. Dad was never around and when he was, he was still never around. He was your preverbal traveling salesman. He was a womanizer, a drunk, and a poor excuse for a human being. He provided a roof over our heads but that was just about it. Mom worked to pay for the food we ate and the clothes on our backs.

I started my own lawn business that spring. I handed out fliers in a nice neighborhood just outside of town and got a couple of jobs right away. I did the best work that I possibly could and apparently impressed them. Word spread quickly and that first week I mowed a dozen lawns in that area and everyone was very pleased. It was a really nice middle class neighborhood where the men all worked at pretty good jobs and where the women had a lot of free time.

That second week one of the women said that she would pay me double to mow her lawn in just my underwear but she settled for just my shorts. To me that was really a deal that I sure couldn’t resist for double the pay. About halfway through the work she brought me out a big glass of iced tea. She was wearing a very skimpy bikini and told me that she would be out back getting some sun. I had already mowed out there. I was to go back out there when I was finished to get paid. I took my time and did a good job while several other women walked by to check me out. A couple of the women stopped me to ask me my price and then they had me add them to my client list. My business was doing great.

Once I finished and went out back to find the lady I got a big surprise. She was lying face down on a towel and she was completely naked. Where she was lying she was concealed from most prying eyes but I was standing right there admiring her tanned body. For a woman in her forties she sure looked good. I cleared my throat and got her attention. She smiled up at me and just rolled over onto her back. I got to see my first set of tits and her bald pussy. She opened her legs up, told me that my money was in her deposit box, and that I had to make my own withdrawal. It was awfully sexy talk. She reached down and parted her pussy lips to show me that there really was money inside her. I got down on my knees between her legs and reached for it. I had to poke my fingers in a little way to get a good grip on it. I pulled out two damp twenty-dollar bills. I told her that it was way too much money. I was only expecting twenty dollars and that was double my normal fee. She told me that I could leave a deposit in her box if I wanted too. She saw that I was confused so she came right out with it. She wanted me to fuck her. Wow! I was a virgin and there was a real woman, a really nice woman, asking me to fuck her.

I dropped my shorts in a flash and got back between her legs. She kept telling me to slow down but I couldn’t. I cum in her way too quickly. She told me that it was okay and that I could stick around a few minutes and do it again. She was right I got hard again in just a few minutes and that time I lasted a little bit longer. She thanked me and asked me to come by again next week even if it was raining. She said that I could fertilize her garden indoors. Again it was awfully sexy talk but I was beginning to catch on.

I thought that loosing my virginity would be different somehow. I didn’t feel like a man or any different. It sure felt good slipping my cock into a real woman though instead of just jerking off like I always did. She was warm, soft, and she smelled so good too. She just laid there open, exposed, and waiting for me to fuck her. The first time was way too short because I was so excited that I could have cum just looking at her. I was so pleased when she said that I could do it again. That time was too short too but it was a lot better.

I mowed three more lawns that day and the last lady did the same thing that the first lady had done. I pulled forty dollars out of her pussy and filled her with cum. That time was the best. I had plenty of time to recover and to think about my first lady so when I saw that lady lying there nude on her belly I knew exactly what to expect. I only lasted a few minutes but it felt like a lifetime to me. I really needed that too because I couldn’t get that first lady out of my mind.

When I got home mom asked me about my day. I told her that I had mowed four lawns and made a hundred dollars. That caught her attention. Soon I was telling her all about loosing my virginity and fucking two of my customers.

My mother looked at me then smiled and said, “Like father, like son.”

Every day after that I mowed lawns, fucked women, and made lots of money. Some days I made a hundred dollars and other days I made two or three hundred dollars. The women just paid me what they wanted too. Halfway through the summer I was fucking four or five different women every day and I was getting a lot better at it too. I could work on Saturday too because most of their husbands were off playing golf or something. My mother wouldn’t let me work on Sunday because she said that I needed at least one day a week to relax.

Well I got restless one Sunday and started mowing my own backyard, then I mowed along the side and out front. When I returned my mower to the backyard there was my mother lying on her belly on a towel, naked. She rolled over and there was a one-dollar bill sticking out of her pussy. She took one look at my face and told me that she wanted change too. I took the bill out of her pussy with my teeth, dropped my shorts, and fucked my own mother right there in the backyard. According to her I was a lot better than my father was at sex.

After I filled her with cum she took me in the house so that we could shower together. I had done that a few times with the other women. Then mom took me into my own bedroom and got on the bed. I told her that I had never made love in a bed before and she just smiled at me. She was pleased that there was still a first that we could do together. When she asked me to eat her out first, we both realized that there were several more firsts that I needed to try.

We spent that whole Sunday in bed trying various things. Mom became my sex teacher. I learned to perform oral sex on her until she had a multiple orgasm. She performed oral sex on me until I cum in her mouth. She taught me sixty-nine, doggy style, and even anal sex. When we woke up together on Monday morning in my bed mom just kissed me, patted my morning erection, and told me to get ready for work.

Each night she enjoyed hearing about my day, about the sexy women that I had fucked, and putting my money away for college. I was bringing in about a thousand dollars a week and that summer I made over ten thousand dollars that went into a bank account. Mom calculated that over the next three summers that I would be able to pay for most of my college expenses.

Mom started sleeping with me every night after that even when dad was home. She would go to bed with him and let him fuck her first if he wanted too and then she would get in bed with me. That was all that dad needed to rekindle his affection for mom. He started fucking mom every night whenever he was home just so that she would come to me dirty and full of his cum. I didn’t care one bit. For some reason he also started spending more nights at home with us than was usual. Mom enjoyed the best of both worlds. Mom and I knew that dad was fucking every woman that he could out on the road.

Dad introduced me to ‘double penetration’ where we both fucked mom at the same time. She had three holes so we each picked one and went for it. Mom loved the extra special attention. She said that she liked it best when we were in her pussy and her asshole at the same time. She said that it was the best feeling of fullness that she had ever experienced. Dad and I kind of liked poking her mouth and pussy at the same time as she shuttled back and forth between us.

Then one day dad brought home one of his girlfriends and we had an orgy. I fucked both women, dad fucked both women, and together we watched them make out too. Mom claimed that she had never been with another woman before but I sure couldn’t tell. She said that she had done it just for me and I appreciated that very much. I even asked her if she would do it again.

After that summer dad started to bring all of his girlfriends home to meet his wife and son. Sometimes we had a four-way orgy and sometimes dad just took them into his own bedroom for a little one on one. It never mattered because mom always took care of my needs. Mom never minded dad fooling around again.

The End
Older Women

Similar stories

HOBO Chapters 12 & 13

CHAPTER TWELVE I woke up early the next morning and was able to ease out of bed without waking Michelle up. I went to the kitchen, started a pot of coffee. I then cooked scrambled eggs, bacon and sausage and was just finishing up when Michelle walked into the kitchen rubbing her eyes. “What are you doing ?”, she asked, yawning. “Making us breakfast. Please sit down on the stool.”, she smiled at me and walked around the bar and took a seat. I fixed her a plate and set it down in front of her , then poured her a...


Likes 1

My Itch - Part 2

When I made it back to the condo unit, I grabbed my purse and ran into the door, crying out in triumph when the lights came back on a few seconds later. Knowing I wouldn’t have a lot of time, I quickly grabbed up several thick towels from the bathroom and shoved them in the dryer along with Itch’s soaked t-shirt and cranked it on high. I ran back into the bedroom, retrieving a laundry basket we kept in the units for the guests and walked back into the living room. I turned the electric fireplace on low, just enough to...


Likes 0

Give Me Some Sugar Part 1 - Rochelle's Tryout

​ Life sure is funny is how it plays out. I have never been a religious man, still am not, but I did listen to the Joel Olsteen guy when the times were bad. He was so positive, that helped, but he also talked about how God could make up for decades of crap, in just a few years through super natural increase. Like I said, I am no Christian and am agnostic about the existence of a deity, but I have to agree that in the least, life can make up for a lot of misery very quickly. In fact...


Likes 0

Keco The Special One

Prologue My name is Keco. Technically that's my human name. My real name is geltrone6went. I'm from a planet called Glutinous billion of galaxies away, and due to some circumstances I ended up on a weird planet called Earth. Where I came from everyone has the ability to transform into different objects and animals. But I was a little different if you will call it that. I was born with every super power u could possibly think of. I think that's why my parents sent me away. To protect me from all the jealous people on our planet. My parents teleported...


Likes 0

CAW#11 - Cold Winters Day

It was a cold winter’s night, in late autumn. The fog had set in; just before midnight and gradually blanketed the streets. The air was full of mist and visibility was becoming difficult, as I walked the City streets. My pimp forced to work the streets tonight. I was hoping for profitable night; to keep him and his henchmen, away from me and my family. My name is Louise and I am a single 21 year old mother, and also a prostitute. I have a three year old daughter, Misty (Melissa). She was being looked after by a close friend. My...


Likes 0

Hoosier Taboo?? Ch. 3 of 6(REVISED).

CHAPTER THREE.. So after aunt Deena & I got finished with our breakfast, we cleaned up the kitchen and the living room where we ate, slept & fucked the night before. It took us no more than 45 minutes to get everything done. Then she suggested that we take a shower together, because of what we did overnight. But I also knew that aunt Deena might still be a little horny, because she was getting a little frisky with me. But what did I care, I just made sweet love to my mom's younger, sexier sister I called my aunt. So...


Likes 0

The Chalkline

The Chalk Line a story by LePhantom © 1997 They had met online, in a chat room. He had been attracted by her quiet manner and sent her a rose as an introduction. They instantly formed a bond. Their casual flirting led to deeper discussions of movies and favorite scents, erotic things, sensuality... It blossomed, the next day they found themselves searching, finding each other every time they signed on... They talked of lives and loves, of things funny and sad... They shared a kiss... tender and gentle, deepening quickly to an almost unmanageable passion... Neither were completely new... neither were...


Likes 0

ROOKIE COP CAPTURED BY WHORES !!! (Femdom, CFNM, reverse gangbang)_(1)

Officer Dan responding to a call from Angela (a police dispatcher), saw them in front of the alley, congregating again. Jesus, these hookers are like cockroaches; you just can't get rid of them he thought to himself as he turned on the red & blue lights of his patrol car. Dan thought about calling it in, but decided against it; he wasn't very well liked by his fellow cops these days. Nothing good would come from mentioning this to dispatch. Officer Rosita, his former partner had just been assigned desk duty, pending an investigation thanks to testimony that Officer Dan had...


Likes 0

Sex on the road side pt of my short stories

We have been to your mothers fiftieth birthday [arty and We’re on our way back home in your car, You have been looking at me all night like you want to eat me alive and decide to pull the car over to the side of the road and drag me out, walking us into a field you tell me to take my dress off. You tell me to stand there in the cold air in just my bra and French knickers; you stand in front of me looking at me before you decide what you want to do. I notice four...


Likes 0

In the closet

Hiding in the closet- My household consists of my mom my my dad and brother. My brother is only 2 years younger than me and we are almost similar. My name is Marcus and this summer my 2 cousins Shay and Aniya are coming over. Shay is my age and Aniya is 4 years younger. It's been a while since I last saw them so this was going to be exciting. I fishing cleaning my room and got ready for my brother to move his things in so that the girls can get his room for the summer. By midnight they...


Likes 0

Popular searches


Report this video here.