Free Sex Stories
Page 1849

My First Prostate Massage

It was a warm summer afternoon and I had just finished an airshift at the Country station where I worked in Texas, when a co-worker came up and asked me to accompany her to a function our station was sponsoring. The event was at a local club where Gary Stewart was appearing and the co-worker was what is known as a BBW and she was married, but her husband was in the Marine Corps and stationed in California. And she had four c***dren at home ranging in age from 7 to 14. Now all the girls I'd gone out with before had been petite (and somewhat passive and empty headed) and I had never been... Continue»
Posted by discmandanny 5 years ago  |  Categories: Anal, First Time  |  
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My Fantasy

Ever since I was younger, I've always been attracted to older men. I would always picture them showing up in suits to whisk me away to some wonderful dinner or show. Then I got older. I started fantasizing about an older man in his 40's or 50's, calling me up and inviting me over. We'd grab a bite to eat then head back to his place. He'd rub my shoulders and kiss my ear. Slowly we'd tease each other to the point of insanity and then the wild and earth shattering sex would begin. I'd stroke him until he begged for release and then we'd fuck on ever surface possible until our bodies could take n... Continue»
Posted by insearchofdaddy 3 years ago  |  Categories: First Time, Mature, Taboo  |  
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My fucked up weekend in San Diego

Hey guys, it's been awhile, some of you have been asking for another story and I didn't have a new one...until this weekend. As some of you know who chat with me, I'm a dancer here in Las Vegas. Anyway, I work with this girl who is like the biggest slut in the place but she can be cool too, she is the only other girl I know who admits to like getting gangbanged so we kinda bond over that cause she makes me feel a little more normal, shes 28 and let's just call her Crystal.

Anyway, she has this total sugar daddy, Mark, down in San Diego and he comes to Vegas and she goes down there sometim... Continue»
Posted by lvdarling 4 years ago  |  Categories: BDSM, Group Sex, Lesbian Sex  |  
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I Did Bukkake One Last Time

I'm really not into being part of a sex show, I wasn't really sure I'd do anything like this again, but Lisa called me. Lisa really wanted to do this, she said she knew the tips would be really big. It was her friend that knows my boss again, he wanted a bukkake party, but he wanted it kicked up a notch or two, he wanted some live sex, instead of just his videos.

I told Lisa I wasn't comfortable with doing too much, and I was going to talk to my boss, just in case he doesn't approve, I won't do it. She told me that he already had a couple, maybe a threesome, to perform live sex acts for ... Continue»
Posted by batoutofhell 4 years ago  |  Categories: Fetish, Group Sex  |  
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Going Down Once Again

"Wait! Hold the elevator!"

My heels clattered against the floor as I made a run for it. I couldn't afford to be late. I was on my way to a business dinner with my boss and a prospective client for the architectural firm where I was employed. It was an important client, and we really needed the contract. I hadn't met Mr. Grant face to face yet, and I wanted to make a good impression so I took a little extra time with my appearance, hence the rush.

I was in a little black number that hugged every curve, with strappy black sandals adorning my feet. I had left my glossy brown hair down aro... Continue»
Posted by oralTcmlvr 3 years ago  |  Categories: BDSM, Hardcore, Mature  |  
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s****rs by the pool

I had admired Danielle for quite some time. We had been in a high school class together for almost a year now, talked on occasion, but never much more than that. She couldn't have stood much taller than 5'3'', and couldn't have weighed more than 100 pounds. Danielle had natural blond hair and blue eyes, with tan skin and an extremely petite, though toned frame. In the few times I had seen her outside of school, she wore tiny cheerleader shorts that showed off how beautiful her slender, firm legs were. She was a bit ditsy, but pretty smart when it came to academia.

I never had much to talk ... Continue»
Posted by aidan1995 2 years ago  |  Categories: Group Sex, Hardcore, Taboo  |  
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CREAMPIE GIRL

"What's the matter, s*s? Can't get off?" My b*****r, Rick, leaned against my bedroom doorway, his arms crossed. I'd been at it for nearly an hour. My MP3 player had a vicious porn video playing and with the ear buds in, and trying with all my might to cum on my vibrator, I simply hadn't noticed he'd been watching me.

Never the one to turn down an opportunity to get myself off, I didn't bother to do anything more then pull one ear piece out and snarl, "Fuck no! I'm horny as hell and nothing seems to be working." I continued to pump my favorite dildo vigorously into my weeping cunt.

"Want ... Continue»
Posted by sexaddict66 3 years ago  |  Categories: Mature, Taboo  |  
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A walk in the woods

It was really hot and sunny today, and I decided to go for a walk in the hills above my town. There's a path leads through some farms over the hill to a little village on the other side of the hill. I'd left early, and there was no-one about. As it got hotter, and he path got steeper, I stripped off my shirt. The heat, and the fresh air on my skin, and the regular swaying of my dick in my shorts got me kinda horny.
The hill levelled out, and the path went into some dense woods. I jumped off the path into the trees to have a piss. I was standing behind a tree, pissing through my semi, when I ... Continue»
Posted by BrendanUK 4 years ago  |  Categories: Gay Male, Masturbation  |  
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The Mechanic

My name is Bruce, I am one of those mobile mechanic chaps you call out when something goes wrong with your car. You get to meet a nice variety of people, some good some not so, with some very good looking ladies thrown in as well, which make it nice. A lot of the clientele are people you see a couple of times a year for a car service so you get to know some of them quite well.

I hadn’t had that much in the way of action for a long time. I had split with my wife a few years before and now I always seemed to be working. Anyway it’s not the most attractive of looks when you hands are covered ... Continue»
Posted by domestique01 3 years ago  |  Categories: Shemales  |  
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School Bus Ride for Virgins only

It was early morning and I found myself dozing off as the bus sped towards town and school.
It was late February, 06:37 and the bus was packing up, with girls from my school and man going to work. The journey was a 45 minute commute for myself, and I started to doze off, more for the lack of oxygen, as it was being used up and replaced with the CO2 breathed out from all the passengers, all the windows were closed because of the snow, and as I looked about me, most of the people around were sl**ping, even those standing.
At one stop some people disembarked and a couple got on, at first I thou... Continue»
Posted by MarieL 3 years ago  |  Categories: Fetish, Group Sex, Taboo  |  
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Buck Scores a Double First - First Milf and First

I was in my 20's when I was transferred from the East Coast to the Pacific Northwest. I moved out there and I liked it - but I didn't know anyone and I had been not going out with anyone. After about three weeks out there, getting settled and getting used to the place, I decided to explore - and I was horny.

I went downtown to an area where there were a lot of clubs and bars. I went in a few of them, trying to find a rocking place - I finally found a bar where I heard some good music - the band was great - some rock, some blues - and lots of folks were dancing and partying big time. I ... Continue»
Posted by buckaroot 2 years ago  |  Categories: Anal, First Time, Mature  |  
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His Wife finds out - Now she my Whore - BBBBTS

Buck's Big Boob Bed Time Stories....


I am 24 and live near the ocean and love my single life. I never want to get married because the women in my neighborhood are to good to give up. I'm still in pretty good shape. I still have my athletic frame from high school. I am 6ft 4in and work on cars for a living. I fuck many lonely women in my shop as I work on there cars. Sometimes I trade sex for repair work. My friend Dave came by the other day. He is married. He just had a baby about a month ago with his wife. You think he was all settle down but he still helps me fuck some ladies who want m... Continue»
Posted by therealbk 2 months ago  |  Categories: Group Sex, Mature, Taboo  |  
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Lena and Masie Chapter 2


Len and Masie Ch. 2

To say that Len was nervous would be a serious understatement.


He had slept a bit later than usual which was normal if he had masturbated the night before, and when he first woke, he lay there luxuriating in the warmth of his bed. In his semi-comatose state, that time when you are not quite awake or asl**p, his mind wandered all over the place, then the events of the previous day came back.

He was suddenly wide awake and wondered if it had all been a dream but quickly recalled caressing his neighbours breast and feeling her hand cupping his penis. It was excitin... Continue»
Posted by sandhilman 2 years ago  |  Categories: First Time, Mature  |  
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My wife flashing customer

It was at the mall the other day we were shopping for some clothes, it was getting crazy because there where so many people she decided to try on a black dress at the dressing rooms, i was there watching with other couples as she was trying it on going back and forth inside the dressing room, i struck a conversation with another fellow bu the name of mike hes wife was trying out clothes as well, my wife comes out and ask me to help her with the zipper as she is holding the top, i try to get it but her big bbos got in the way so i tell her to hold the bottom well what came next shocked me she d... Continue»
Posted by joe6977 3 years ago  |  Categories: Voyeur  |  
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wife knocked up for 3rd time by ex boyfriend

Vegas seems to be my wifes weakness.

My wfe and her best friend were there in November celebrating their 40th birthdays. At the time they left, I was not aware that it had been arranged by my wifes friend for her ex from highschool, who now lives in Dallas to meet them there to help her celebrate in style.

She was not told he would be there this time, so it was a total surprise, when they were lounging by the pool and who should swim up and climb out of the pool, but Darcy, her well hung ex from high school.

After 2-3 hours of swimming, drinking, flirting, my ussually pu... Continue»
Posted by rt305 5 years ago  |  Categories: Hardcore, Mature, Taboo  |  
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A Roommate

Just before coming to college, my girlfriend and I ended it. Though I had slept with a few girls since then, I still couldn't get over my ex.
At college, I live in a dorm room, and have a few friends on the same floor as me. Seeing me upset over my not so recent break-up, one of my buddies asked if I wanted to have a few beers and watch a movie. Thinking that it would take my mind of things, I agreed.
After a few beers and much searching, we finally agreed to watch a comedy movie, he told me that he had seen it just last week with his girlfriend but would like to see it again. As the movie ... Continue»
Posted by menusite 1 year ago  |  Categories: Anal, First Time, Gay Male  |  
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My shemale boss part 3

I was woken by the vibrating noise of my mobile and looked over at the time, the bedside clock said 1am. The caller I'D on the phone simply showed Bitch, naimly my boss Miss Jones, would she never leave me alone.

I answered the phone and still being half asl**p simply said 'yes'.
'Don't answer me with that tone Rob' she said. 'Sorry, but its one in the morning' I replied.
'Be a darling Rob and pick me up from the club, text me when your outside'. Before I could say anything she hung up.

I pulled my arse out of bed, slipped on some tracky bottoms and a t-shirt, jumped in the car and dr... Continue»
Posted by big_rob49 2 years ago  |  Categories: Shemales  |  
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Long Time Crush

When I was twelve I met a new classmate named Dave, he and I became great friends hanging out, joining clubs and what ever else high school k**s do. His f****y was from the Phillipines and he and his s****r were the first generation born in this country. His s****r Mai is the focus of this story. She is two years younger than Dave. I had a crush on her from the moment I saw her. She was one of those girls that even at a young age people would say how beautiful she was. Long black hair, deep brown eyes and that great skin tone she was just stunning.
But as she was only ten at the time I ... Continue»
Posted by triphammer73 1 year ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Titty fucking my granny



My name is Jack. I live with my mom. My grandparents live right around the corner so I go there a lot. My grandmom has very big tits (36DDD) and most of the time she shows cleavage. It ALWAYS gives me a boner. I"ll usually go to the bathroom to jack off and relieve myself. Well this is a story about the one time I couldn"t take it anymore.

Let me describe myself. I"m 18, 7 and a half inch dick. Six pack. That"s about it. Now let me describe my grandma. She"s 51. She"s skinnny. She has, like I said, 36DDD tits. And... Continue»
Posted by iceman0804 2 years ago  |  Categories: Mature, Taboo  |  
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SWING SHIFT GRANNY II

My wifes job scheduled her for an out of state training seminar the weekend of our anniversary. I had already taken the week off because we were planning a trip before Judy got the news, but since her trip was manidtory I decided to relax at home while she was away. Judy told me that her Aunt Gladys was still coming to town to spend some time with her mom Lillian. She said, "you know my momma didn't want to just be here alone while we were on our trip". The two s****rs hadn't seen each other in 5 years and thought it would be a good time to catch up.

Judy said, &... Continue»
Posted by lexasgreen 5 years ago  |  Categories: Anal, Mature  |  
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