Free Sex Stories
Page 1736

First time trying anal.

I didn’t actually write this one, a very dear friend called Wendy wrote it and asked me to have it published, here we go – be kind to her in your comments:


My first time trying anal was with Chris my b*****r so I would have been in my early teens. Somehow, it wasn’t done deliberately, well, I suppose it was, but not like, “Well we have tried everything else, might as well try this.”

It was like just experimenting and meaning so much to each other that we couldn’t wait to try everything and that was just part of what we were desperate to try.

From the size of my pussy, he could see... Continue»
Posted by pinks43 3 years ago  |  Categories: Anal, First Time, Taboo  |  
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BBC losing virginity to fat older woman

Ever since I was a young boy, I have had a condition where my dick would suddenly get hard and grow like crazy. Some days it would only happen once a day and other days it would happen up to 4 or 5 times a day. It didn’t really bother me at a young age. Sometimes my dick would get so hard that it did hurt a little bit, but it would never last for very long, so I never had to pay to much attention to it.

It started getting worse when I was 14 years old. I don’t know what triggered it, but I can remember that it was starting to become a problem at that age. I had my first “real” girlfriend wh... Continue»
Posted by giandro84 9 months ago  |  Categories: Anal, First Time, Interracial Sex  |  
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Strap-on Fun

While walking one evening I saw a friend go into his new neighbor's garage. A man walking into another man's garage may not seem odd, but rumors have surrounded this new neighbor since he arrived in town. Everyone says he is gay. He isn't married, nor does he appear to have c***dren, but that doesn't mean anything. He seems quiet and keeps to his self, so no on really knows for sure. Chalking it up to idle gossip, I pushed it from my mind until now.
I continued my evening walk, around and around the block I live on. I hate to say it but every time I walked by the garage I wondered if they ... Continue»
Posted by ookubit 5 years ago  |  Categories: Anal, Hardcore, Taboo  |  
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My first time gay anal

Note: ——I am NOT the author!
I am simply sharing this lovely story with all of you because I have not seen it on here



Gay Story


It was thursday Night and I got off of work at 6pm, I was not ready to go home just yet. I was In NewYork that day We had to go to this long boring seminar, My job makes us go every year.

So I was in NewYork city that day and was off work and going to a bar. I walked in to this bar it was nice. I asked the bartender for a beer and took a seatI was just done with my forth beer and had to go to the bathroom. I walked in to the batheoom and over tothe onl... Continue»
Posted by adel5000 4 years ago  |  Categories: Anal, Gay Male  |  
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Makin' An Asian

I could barely believe my luck...

You see, I was bored one day, and tired of watching the crap on TV, so I had gone on the Omnibus Meetup website just to see what was out there. I put in my Adult Friendface ID to log in, and I started looking around.

Within a few minutes, I suddenly got a message about a girl I probably would like to meet. She had gotten on recently, and apparently she wanted to meet a slightly older white guy (like myself) for some strings-free sex. And here's the kicker: she wanted to get pregnant!

Hastily, before anyone else could grab her, I sent her a messag... Continue»
Posted by billstew 6 years ago  |  Categories: Hardcore, Interracial Sex  |  
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Truth or Dare: The Adult Bookstore Part II

There he was, just blocking the way to the door. Over sized red t-shirt that did not hide his size, grey sweat shorts pulled down mid thigh, with penis in hand, tugging in a very automatic way. But it was the look on his face that I will never forget. Sort of like a hungry man looks at a piece of pie mixed with the way a k** looks at another k**s toy with longing and jealousy.

I kept trying to clean up, wiping the side of my face and neck. Then I made a move to step forward and pass him but he leaned in to block my way and smiled. And then a hand landed on his shoulder and the s... Continue»
Posted by beth080808 4 years ago  |  Categories: Group Sex, Hardcore, Taboo  |  
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THE SHOWER

Starr watched her father's big cock through the keyhole of the bathroom door. As he drew a shaver across his face, his huge prick moved. The thick cockshaft swung heavily. Starr licked her lips. She let her hands move to her virgin cunt and she stroked her pink pussylips as she watched.

Starr had always thought that her father, Rick, was an attractive man. Tall, dark, and handsome, with short Black hair and piercing blue yeas. He was 20 years old when she was born, so he was only 38 years old now, and therefor she didn't think of him as an "old man." The two of them were always close and, d... Continue»
Posted by sexaddict66 4 years ago  |  Categories: Mature, Taboo  |  
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step mum pantyhose

I was 18 yrs old and just moved into my dads and step mums house..Its a saturday night and my step mum was getting ready to go out..as i approached the top of the stairs i saw her slipping into a pair of sheer black tights..her big hanging tits brushing against her nylons as she pulled her tights up to her waist..i froze..just staring at her huge purple nipples.she smiled reached for her bra,bent over and sat her perfectly formed tits into her bra,re adjusted herself and closed the door...we arrived at the pub to meet friends and started knocking the drinks back..as the night progressed my ste... Continue»
Posted by hoseuk 3 years ago  |  Categories: Fetish, First Time, Mature  |  
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Naughty Girl


You are waiting in the corridor outside the headmasters office,you have been sent to him for playing with your moble phone and how you was playing, when they did a smokers check of the toilets they found you, knickers down with your moble on vibrate inbetween your splayed legs and when the teacher said Suzie get to the heads office that familier tingle of exitement went through you because you had been there several times before and knew what to expect.

So waiting in the corridor your 18 year old already experienced body tingling with anticipation of what was to come.Suzie the voice shout... Continue»
Posted by Sammysex 3 years ago  |  Categories: BDSM, Fetish  |  
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You've Got Shemale.

This is my first story of this type, so please, be gentle ;) It's a semi-true story, but definitely more fiction than fact, and it will be at least two parts.



I moved to a smaller town when I was in college and found that I didn't fit in at all. I actually got so lonely that I took up a friends advice and joined a dating site.

I had gone through a large number of messaging women on that site to find most remotely near me wanted nothing to do with me. My age range of early twenties had little selection and those that were in that range were surprisingly stuc... Continue»
Posted by MysticDude 4 years ago  |  Categories: First Time, Hardcore, Shemales  |  
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40th belated birthday

Chapter 1

It was a few years ago, my wife had done exactly what I'd asked her to do - for a change - and completely ignored my 40th birthday. I mean come on, people say don't make a big deal, but deep down that just means Hey Make a big deal!
So anyway the monday after the weekend of my non celebration i was back at work. i work as a rep for a computer sales and leasing company, so Monday i picked up my sheet for the week and hit the road.

I had three calls to make that day and the last of them was a new addition to my area. I was still feeling a little pissed off after the no event of ... Continue»
Posted by gerry69uk 3 years ago  |  Categories: Hardcore, Mature, Taboo  |  
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My first adult cock, part 3

As we pulled into Dougs driveway the older gentleman turned to me, his eyes lowering to my crotch and lingering for a moment. Though I was nervous my cock had begun to swell with my excitement as I had loosend the leg of my shorts. But as his eyes lingered I felt my heart race and felt my cock swelling faster now, I became filled with embarrasment and excitement. I felt my face flush as his excitement became apparent, in that instant I wanted to peel my shorts down and offer him my smooth young body as I begged him to allow me to taste his large cock.
As his eyes raised all I could think ... Continue»
Posted by Adicksion 3 years ago  |  Categories: First Time, Gay Male, Taboo  |  
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Road Trip

I just wrote this story and I would love all the comments you would like to leave for me.





My f****y was driving across country to see my mom's side of the f****y....
My dad was driving and my s****r was sitting next to him up front. We had a big van with a bed in back. Mom was sl**ping facing the front of the van and I was behind her. I suddenly felt her hand rubbing on my cock. Maybe she thought it was dad behind her at first. I don't know for sure. Then she pulled it out of my shorts and started stroking it. She started pulling it towards her pussy and I moved in closer to help. ... Continue»
Posted by presmith40 3 years ago  |  Categories: Taboo  |  
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My First MILF... (OMG)

My First MILF... (OMG)

in my first story, (the meeting) i shared how we met, now, I will tell you the incredible true story of our first shared lovemaking.

Her name is Connie. She has no lack of confidence, she's very sure of who she is, and what she wants and needs. At the same time, she's a little girl and a woman with a wonderful sense of love, joy and life. She's just fun, and is really nice to be around... and a good person you would like to have as a friend. She has an incredible smile, bright eyes, and very soft light brown hair. A great figure for a 55 year old woman, quite... Continue»
Posted by lynnp123 5 years ago  |  Categories: First Time  |  
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S****r Love

s****r Love – Strap-on Fantasy

By billy69boy

Emma found herself smiling as she drove to the airport to pick up her little s****r Amy. The two girls were very close, despite the disparity in their ages. They really missed each other, and now they were going to spend the entire summer together.

Emma was proud of herself. At 20, she landed a good job, and she could afford her own place in the city. She was finally on her own; free to call her own shots. Funny thing, though, she was only away from her f****y for a few months, and she had bouts of homesickness that she kept to herself. Now... Continue»
Posted by drew1207 2 years ago  |  Categories: Anal, Fetish, Taboo  |  
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Wife's Surprise

This story is Fiction (as of now):



My wife and I have been married for some time now and we are both very sexually active. I am 6 ft, white, athletic build and a 7 in cock. My wife is a BBW, white with huge tits and ass. We love to do everything sexually including playing for people online, posting pictures and she even fucks me with a strap-on (as seen from our pics). But we haven't let anyone else join in yet until now.

I'm at at work and texting my wife and ask if she made any plans this weekend. She said the only plans she had was for tonight and it was a surprise. Intrigue... Continue»
Posted by michaelelaine 2 years ago  |  Categories: Anal, Gay Male, Group Sex  |  
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The Trip part 2

I awoke suddenly feeling dazed and with my head pounding.

"Kara, baby...you okay?" asked Chris

Chris roused from his slumber and reached for me. I was sitting up, breathing hard.

"It was nothing. Just a dream, I guess."



"Okay. If you say so." He rolled over to look at the clock. "It's about time to get up anyway. Must have been more tired than I thought."



As I gathered the covers around me, I noticed, I was wearing a Japanese schoolgirls uniform, there were red marks on my wrists that looked like rope burns and I could feel fresh cum leaking from my ass. Chris saw me squirm... Continue»
Posted by kara_zor_el 4 years ago  |  Categories: Shemales  |  
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How i ruined a 20 year old

Work gets boring sometimes, always the same thing every day but not that day as I glanced up from my work i saw something that instantly made me wet, he was on the tall side, I would say 6 foot, with beautiful soft long curly hair all pulled back in a neat pony tail, I'm not usually attracted to such dark guys but that smile and those deep dimples made my knees week. He spend a better part of a week finding any and every excuse to come talk to me and in one of those moments he asked how long I worked there and when I told him 12 years he asked how that could be and I told him my age, I was 39 ... Continue»
Posted by glowbug8 3 years ago  |  Categories: Hardcore, Interracial Sex, Taboo  |  
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Friends Mom

It all started when I met my friend Brian in the eighth grade. We bacme friends and then we decided to do something on the weekend. We went out to see a movie and I decided to spend the night at his house. His mom came to get us and when isaw her i realized that she was the biggest milf that i had ever laid eyes upon. She was gourgeouse. Her tits were plump and round I would say a 36-38 C. They were so perky and perfect that I was not sure that they were real. Her ass was the most beautiful thing that I had ever seen. It was small and plump and her jeans hug around it perfectly.

She gave us... Continue»
Posted by maxtester 1 year ago  |  Categories: Anal, Mature, Taboo  |  
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Ultimate Saddle Thrusting Sex Machine

'I think we are here', my husband said, trying to catch his breath. The long flight of stairs to the top were indeed daunting, but now we stood in front of a shabby looking door, at journeys end, for this part at least.
We had travelled here with the sole purpose of purchasing 'Ultimate Saddle Thrusting Sex Machine', the owner claiming it was as new, never used, and having vied it on-line, called him, and agreed a price of £85.00, less than halve.
I told my husband I thought he sounded oldish, but he just laughed and said wishful thinking, so when I rang the doorbell and he opened it, both o... Continue»
Posted by MarieL 4 years ago  |  Categories: Fetish, Group Sex, Voyeur  |  
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