Free Sex Stories
Page 1779

Housekeeper (moms best friend)

As a k** growing up, I would often go with my mom as she visited her lady friends. At some point I began always needing to use the restroom while we visited so I could search for the ladies dirty panties. I loved to sniff them while jacking off.

One lady in particular was my moms very close friend and we use to visit her often, both at her and her husbands house and their lake house. This lady was always very hot and I was checking her out all the time growing up to the point where I use to let her catch me looking at her tits, ass and pussy all the time. I use to stuff her panties in m... Continue»
Posted by dogg2009 3 years ago  |  Categories: Masturbation, Mature, Taboo  |  
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My Best Friends Mom 1

I had always considered Jimmy Bradford to be the luckiest guy in the world. Jimmy had a cool mom who was always friendly and went out her way to make anyone feel special no matter what. However that wasn't the main reason I considered my best friend to be lucky. It was the fact that he had a hot and sexy mom.

Ever since I can remember I had always had a crush on Jimmy's mom, Jenna. In the beginning it was more like a school boy crush and Jenna knew it no matter how hard I tried to hide it. Even though she was a good 23 years my senior, she thought it was cute and went along with i... Continue»
Posted by dallaskid23 5 years ago  |  Categories: Mature  |  
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Poker game Gang Bang



When I came home from work at 12:30 am, daddy was still playing poker with the guys. The kitchen was filled with smoke from cigars and pipe tobacco. I love the smell of pipe tobacco, it reminds me of my grandpa. When I was just a freshman in high school, grandpa use to watch me in the shower. He would always have to pee when the shower would turn on. I think grandpa was my first fingering, besides myself. Grandpa had thick furry fingers and he knew just how to slide in gently, so I wouldn't make a bunch of noise, once he was inside me.

I walked up behind daddy to get a look at his... Continue»
Posted by loloishorny 2 years ago  |  Categories: Group Sex, Hardcore, Mature  |  
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Watching my b*****r-in-law fucking my Mother

It began when my b*o-in-law Ashley came to stay with me and my mother for a week. Although older than me at 30, Ashley was an attractive man who looked 10 years younger . He was a successful businessman, married to my s****r, although they didn't spend a lot of time together unless it was at the office (she also worked part-time at his firm). Although at the beginning of the marriage she was not happy with the hours her husband worked, once his company became profitable, she got to enjoy the dividends that it brought (money, car, designer clothes, etc…). She also organised herself a good soci... Continue»
Posted by prathyushsinah 1 year ago  |  Categories: Hardcore, Taboo, Voyeur  |  
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mom is my birday call girl (Not True Story)

Introduction: a guy orders a call girl for his eighteenth birthday and is surprised at who shows up on his door

Two weeks ago was my 18th birthday. My f****y celebrated with cake and a party, it was great. But tonight I was planning on celebrating my birthday the right way. I told my mom I was going to go hang out with my buddies but instead I went to a cheap motel and called an e****t service. I asked for the nastiest, naughtiest slut they had.

I felt bad about lying to my mom, because I’m really all she has. My dad walked out on us a few years back and since then she has been s... Continue»
Posted by PornApocalypse 2 years ago  |  Categories: First Time, Mature, Taboo  |  
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Life With s*s

If one thing is certain, life is full of changes. Just when the girls were starting to plan their trip to Virginia Beach, mom and dad had a meeting with Stephanie to tell her that they really didn't want her to go that far, besides with plane tickets it was going to be really expensive. They suggested picking some place that they could go to by car no more than a one day drive. There was some arguing and crying, but she agreed to ask the others to reconsider and pick a new place.

This wasn't what they wanted, but the girls decided that they'd like to go to the Twin Cities in MN and spend... Continue»
Posted by batoutofhell 4 years ago  |  Categories: Fetish, Group Sex  |  
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Vacation

A few years ago I took my lovely wife on vacation to Mexico for a week. She enjoyed the shopping, but it was hot and sweaty. As a result I bought her several sundresses to wear and persuaded her to go commando. This she readily agreed to. We had a guide called Juan and he and his wife took us to a club which boasted “live entertainment”.

The evening started out as expected with dinner, drinks and Spanish singers going from table to table. The entertainment shifted to the stage, with a romantic play going on. During the play I started to rub my wife’s leg under the table. Having had several ... Continue»
Posted by denniscarpenter 2 years ago  |  Categories: Group Sex, Hardcore  |  
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Wet Wednesday

Wednesday is the day every week that I get a delivery at work, I'm on my own until the drivers turn up usually around 10am. When they knock I adjust my dress, the bottom a little higher , the top a little lower, I always go commando so that when i sit on the stool my wet lips can be seen. This week there were 3 delivery men , all muscular middle aged men all carrying heavy loads! I watched them going to and fro carrying in boxes, I rotated on my stool so they got a good view up my dress from all angles. One of them asked me if I needed any help unloading the packages , I replied that I am a ex... Continue»
Posted by bookers 4 years ago  |  Categories: Anal, Group Sex  |  
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Spanking Day By Scott Darth

The twelve chimes of the clock tower heralded the top of the hour. It was noon, and a large crowd had gathered in the town square outside the courthouse. A crowd this big could only mean one thing. Today was Spanking Day.

A large wooden platform about three feet above the ground had been erected in the town square outside the courthouse. Judging from the number of cushioned mats that were brought out with the horse, it looked like about a half a dozen women would be spanked today.

William Davidson was in the crowd, looking down at his watch. Though he and a couple of the officials in... Continue»
Posted by slave_alison 3 years ago  |  Categories: BDSM, Voyeur  |  
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How Grandmother Kept Her Cool

My grandmother lived in the guest cottage on our property when I was a teenager. It had been a long hot summer. Too hot to do anything other than laze in the shade. I sat beneath the willow tree in our back yard and watched her as she bent and weeded the flower bed close by. Her amazingly plump breasts dangling in her loose house dress had the unexpected result of hardening my adolescent cock. I was a virgin and hungry to know what sex was all about, but too shy to approach a girl my own age. My sex life consisted of masturbating behind the closed bathroom door two or three times a day imag... Continue»
Posted by jackevermore 3 years ago  |  Categories: Mature, Taboo  |  
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Sam guards my cock

The summer after my senior year of high school I got a job as a life guard at a local swim club. I was one of two male life guards there, the other was in his 40's and was actually the manager of the club. All of the other guards were female, between 18 and 22 and all of them had swimmers bodies. Lean and thin, long legs. Working with them and all of the bikini clad girls running around could become a problem. I really needed to concentrate when I was on the stand because if I got too distracted girl watching someone could die. Luckily that never happened.

Some of the best days at the pool ... Continue»
Posted by slapnuts69 4 years ago  |  Categories: Hardcore  |  
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Another business trip (True)

I went down to the restaurant in the lobby for dinner at about 7ish. The place was pretty busy with mostly business dinners and office after work social gatherings. There was a group 6-7 of women sitting a table. As I went through dinner I noticed I kept connecting eyes with one woman in particular. She was a mid-30s, attractive business professional type, just above her shoulder brunette, about 5'7"ish great body in a girl next door type of way, slim to average but proportional. I thought that maybe it was a coincidence but after a few more glances I could tell she too was looking in my direc... Continue»
Posted by hunknhot 2 years ago  |  Categories: First Time, Masturbation, Mature  |  
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My Tickle Dream Cum

It starts out, with me staying with an old friend of mine. He lived in West Virginia, with his hot wife and his teenage daughter. Her name is Mckayla. I was staying there for a few weeks to house set for them so he and his Wife could go on Vacation. Mckayla was going to spend the week with a girlfriend down the road. I do a lot of House setting for people, and love it when they have a younger daughter.
Cause they have the most wonderful panties. I would spend the week masturbating with and into them. Sometimes taking videos of my sessions but one night I was just setting around when I he... Continue»
Posted by wackone 2 years ago  |  Categories: Masturbation, Taboo  |  
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A Mother's Fantasy come true!

Let me start by saying I first experienced i****t years ago with a cousin up until he got sick and passed away.

I am the mother of 2 wonderful sons and ever since they were tots I taught them to be free spirited and not afraid to express themselves, I was a nudist by nature and I taught them to be free to walk around nude as well...when they were young I never thought of touching them nor have them touch me but as they got to be teens I started noticing they were growing rather well if you know what I mean.

I would busy myself so that I would not have to think of how sexy they both have ... Continue»
Posted by justimagining 4 years ago  |  Categories: Taboo  |  
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the holiday

The story that follows is completely true, only the names have been changed to protect their identities.




I was almost there. I was almost at the end of a long bus ride home for christmas break. I was meeting my ex-girlfriend, and spending the holidays at my b*****rs house. After about a week, my ex asked me to stay with her. I styed with her through the rest of my stay before going back to college.

She told me she had a suprise for me, for new yers eve. We went to dinner, and then she directed me to a motel she had booked a room at. Little did I know, until we went to t... Continue»
Posted by chefjohn2112 2 years ago  |  Categories: Anal, Gay Male, Group Sex  |  
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Jerking off with Karen

The April before my senior year, just turned 18, and there was a lot of change in my life. One of the biggest is that instead of having a large stand of woods behind my house there was now a small strip and then a development of new houses. This was a really big deal, I spent a lot of time in those woods as a k**, and now it was one more sign that I was not a k** any more.
I would often take walks in the early evening and I still did, just with a new route. One night as I was walking behind one of the houses I noticed lights on in the second floor. The blinds were wide open. I paused and w... Continue»
Posted by slapnuts69 1 month ago  |  Categories: Masturbation, Voyeur  |  
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s****r In Law

Oh my sweet s****r in Law


I read a number of stories about how guys have a fling with their younger and old s****r in laws. How they enjoy fucking other member of their f****y and how hot they are compared to their wives. But my story is truly true and to this day I still can’t believe what happened between us.

It started when I was dating my wife and we went to visit my now s****r in law in another town , My wife and I had not been sl**ping together so I got to sl**p on the couch in the f****y room while she slept in the spare bedroom . My now b*****r in law was away on a busi... Continue»
Posted by bigcityguy 5 years ago  |  Categories: First Time, Taboo  |  
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Sweet Dreams My Love (Part 3 of 3)

"I don't regret it though," said Jason. "I've always fancied her. Thanks!" he said to me and I thanked them back for a good night, although it felt strange to do so.

"We should do it again, maybe?" said Leighton and I couldn't help but agree. The sight of Lyndsey being screwed was still playing over and over in my mind, and despite having cum twice already, the thoughts were still making me aroused.

"Maybe," I said to them both as they prepared to leave. "We'll see. I'd rather she was awake and fucking you, but she's too prudish to ever let that happen."

Leighton showed me a picture o... Continue»
Posted by tcg 4 years ago  |  Categories: Group Sex, Taboo, Voyeur  |  
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Complete Stranger's Toy

I was 24 working at a bar in the bottom floor of a condo in Daytona Beach last summer. It was a small place with mostly the same couple of locals and the people staying in the condos. I could almost take a new peice of ass home every night witht the constant flow of d***k girls and guys coming in and out every week. I am a bi guy average build brown eyes and hair. I was working one Tuesday night which is always the slowest night of the week when a guy came in and sat down at the bar. I asked him what he wanted to drink and he ordered a crown on the rocks. It was getting close to closing ... Continue»
Posted by tim_likes 3 years ago  |  Categories: Anal, Gay Male, Hardcore  |  
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Daddy's fat cock

I came home from work so so frustrated I had finally caught my boss fucking one of the other cashiers I watched them his fat cock sliding in and out of her wet pussy. I could feel my pussy get so wet watching him fucking her so hard hearing her gasp and and moan fucking her harder and harder . I was so hot wanting to be her she is my age 18 he is 56 he was so sexy to me his cock filled his pants he was always rubbing against us as he would pass by us. sometimes he would stand behind me and grind his cock into my ass !! Damn her why her and not me !! I suddenly heard someone coming back into... Continue»
Posted by sweetflower 2 years ago  |  Categories: Taboo  |  
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