Free Sex Stories
Page 1864

First Time With Tranny

I had fantasized for quite a while about hooking up with a hot chick with a nice cock. I gravitated towards shemale porn and couldn't get enough of it. On this particular day I was having a few drinks and browsing the web for my favorite shemale movies. I discovered the gay.com chat forum. Soon I was chatting with this hot asian crossdresser. She was about my age (21 or so at the time) and lived just a few towns over from me. We shared some fantasies and seemed to have a good connection. She was a smooth slim tranny and she loved to suck cock and get fucked and that's exactly what I ... Continue»
Posted by jay01973 6 years ago  |  Categories: Anal, First Time, Gay Male  |  
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My s****r Andrea comes to visit .. and stay

Please comment. I like writing, but your feedback is what keeps me posting here instead of somewhere else... And if you can't comment, at least click the X's at the bottom to show what you think!
Thanks, I appreciate it

This is all made up ... at least at this point in time...

Andrea is my younger sibling and about a week ago, she called to say she would be in town. I insisted she come and stay at my house. Susan, my wife, had left the day before to do a six month accounting job in the Orient. This was not that unusual for us over the last five years. In order to cope with our sep... Continue»
Posted by imornery81 3 years ago  |  Categories: First Time, Mature, Taboo  |  
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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 4 years ago  |  Categories: Mature, Taboo  |  
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Tempted by b*****r (Part 2 out of 8)

But I don’t know if it’s the movie or the presence of my b*****r. But I just couldn’t concentrate. This time I was pressed against his arm even more, but it was done all purposely. I had no clue what was going on in the movie. What I knew, was that the smell of his body was so musky, masculine and invigorating. His arms looked so strong and manly. The feel of his body so close, got mines shivering. My pussy wouldn’t calm down, and I couldn’t stop trembling.

-Woah. You look so cold. Hold on, I’ll get a blanket.

I didn’t want to let go of him. But reluctantly I did, still not able to cal... Continue»
Posted by MidnightFantasy 5 years ago  |  Categories: Fetish, Masturbation, Taboo  |  
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My First Erotic Massage


As a career woman, I have a very stressful and demanding job. It doesn't leave a lot of time and energy for a life outside work. So I get a massage and a professional stretch every Friday. As I walk into the Spa, I notice a muscular, well-defined man man with rugged good looks and bright blue eyes standing by the counter. I look him up and down admiringly while his eyes are averted. My breath catches as I view him from behind while he walks towards the back of the spa. He glides down the hallway, his ass looks so great in his tight black jeans.

As I check-in for my MST massage/stret... Continue»
Posted by EmmaLoveXXX 16 days ago  |  Categories: Anal, Taboo  |  
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Eileen's first time at 75

So Eileen lives just down the road from us and most of you men reading this wouldn't give her a second glance. She is 75, short grey hair & plump and not particularly attractive. In fact even for a horny guy like me who likes an older lady, Eileen wouldn't be in my top 50 to want to fuck.
However I have been sure for a number of years that she has a little crush on me.
Not that I see her often, but as she lives alone and has no f****y in the area, my wife and I do a few odd jobs for her.
In fact it was my wife, Kath, who first got friendly with her about 10 years ago and since then she ha... Continue»
Posted by maytoseptember 2 years ago  |  Categories: First Time, Mature  |  
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babygirl gets a late night visitor

It’s 3am and babygirl is asl**p in her bedroom… her k**s and m***y asl**p in their rooms. Daddy is awake and horny so he drives over to babygirl’s house and quietly walks over to her window… pushes the window up. Babygirl wakes up and wide-eyed looks at daddy with surprise… she whispers “No Daddy! You can’t come in! What if you wake the b**s?”

Daddy just smiles and says “Well, baby… you just better be quiet!” as he climbs in the window. Baby is a good little girl and is nakk** so when daddy throws the covers back her huge tits and bare twat are on display for daddy. Babygirl is nervous and... Continue»
Posted by SpankieDaddy 3 years ago  |  Categories: Hardcore  |  
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My First Straight Threesome

Further to my story "My First Cock Fucking" I want to relate what happened when the woman in that story introduced me to one of her female friends. After one of our group sessions this woman, the wife of one of the male participants, spoke to me out of earshot of her husband. She asked me for my telephone number and made me promise that I would say nothing to her man as he did not want her having sexual contact with other men unless he was present.
So I gave her my number in the UK at that time.
After a couple of weeks, I was still only 18 years old at the time, I received a call from... Continue»
Posted by shagaddict 3 years ago  |  Categories: First Time, Group Sex, Mature  |  
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THE FUN f****y TRADITION

Jeff sighed disgustedly as his dad swung onto the dirt path that led to their f****y summer cabin. He saw his father glance over when he sighed and he really didn’t care if he heard him or not. He knew it wouldn’t do any good to, once again, voice his dislike at spending his eighteenth birthday the whole damn weekend of it, down here at the lake. He had argued strongly with his mother and father about this but it hadn’t worked. They had insisted that he do as they wanted and that he would probably enjoy himself.
Fat chance on that he wanted to tell them. There was absolutely nothing, repeat ... Continue»
Posted by famlover66 4 years ago  |  Categories: Mature, Taboo  |  
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Sex sacrifice

I was over at Peter's place with his younger b*****r Matt. Pete and I had fucked plenty of times before but his b*****r Matt was younger (21) and I didint know which way he leaned so I had gone over not expecting much.

We started drinking and before long the subject turned to sex at whch time Pete whipped out a straight porno and put it on. I figured this was his sign that his b*****r wouldn't be interested...and beside he was his b*****r he couldnt' go there.

After a while Pete kept looking over at me realising the bulge in my pants and ralised I was horny and hard. He looked at me and... Continue»
Posted by joesal 5 years ago  |  Categories: Anal, Gay Male  |  
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First time with a guy

I had been without sex for a coupke of weeks.
I even had tryed to stop wanking, so my balls were ready fo r something to happen. I stopped of at a known gay loo I had always had a bit of a fasination there. I walked up to the urinal and there was a guy standing the other end almost with his back to me. I couln't see if he was up to anything. I got my cock out and started giving it a bit of a rub. I wasn't shy because he wasent looking at me. I got hard very quickly. Just then another guy came in and stood between us he was only an arm length away. he was very cheeky and wanted to look at my c... Continue»
Posted by gracebiboy 3 years ago  |  Categories: First Time, Gay Male, Voyeur  |  
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Holiday Fuck Fest With My Auntie


I'm Kyle , I Am 19 ,6 ft 2 , muscular athletic build , darkly tanned , 9 inch uncut, dark hair ...



About 2 months Ago I was Having A really hard time , i had just lost my job and weeks later caught my girlfriend cheating in a nightclub.
I was Falling Apart , I was constantly depressed and no matter what anyone said or did i didn't feel any better.
Then One day When i was sat at home during the day the house phone rang , i picked it up and it was my Auntie Liz Who Lives in Cyprus ,she asked me if my mum was home and i told her no , she then said 'how are doing anyway kyle i have not ... Continue»
Posted by bigwillyuk 4 years ago  |  Categories: Hardcore, Mature, Taboo  |  
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I can't believe I fucked my grandmother

This happened a long time ago, but it is still on my mind like it was yesterday.

It was the end of my high school junior year, I was barely 17 when summer arrived. I needed a summer job but the economy in my town stunk and I was having no luck. I was desperate.

My folks were worried about me and we brainstormed one evening about places I could look for work. Finally my mom hit upon an idea, I could move to Utah and live with my grandmother for the Summer. I would probably have better luck looking for work there than in my hometown in Oregon. It made sense. So, we called grandma and she a... Continue»
Posted by zopri 3 years ago  |  Categories: Mature, Taboo  |  
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f****y Camping Trip

2 friends want to spent the summer together and this get discovered
Abigail flung her bag onto Olive’s chair and threw herself down onto her best friends pure white bed making her long black hair spread out around her head. She locked her beautiful green eyes onto Olive as she exhaled sharply “I just found out that instead of staying home like we do every summer my dad planned this camping trip, we are going out to a f****y cabin somewhere in the middle of nowhere. You have to come with me Olive, my dad says it’s okay if I bring a friend along. You’re the only one I’d even consider bringing,... Continue»
Posted by majfred 1 year ago  |  Categories: Lesbian Sex, Mature, Taboo  |  
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“Some first date, huh”

So I had just gotten this new job at a fast food/dine in kind of place for the summer trying to make some extra money before the fall semester started. And there was this boy named Danny that would come into the restaurant every so often. He was really cute and had nice lean looking body. He was pretty shy but I could tell he was in to me because quite frankly the food wasn’t that good and he would always stop by during my shift checking me out. So a few weeks past and he had yet to make a move. I was a little hesitant as well because I didn’t know how accepting he would be of my “situation”. ... Continue»
Posted by pleasurenfun 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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My Ebony Prince

I had only just started licking the sultry asshole of my new roommate, Terry, when his plump, oversized balls began swelling in my hands. I love cupping balls, squeezing them. Especially ones that have been stimulated and deprived of their release for as long as Terry's. Before I started to nibble his furry bung I had given his feet and strong, well-toned legs the majority of my attention. I worshiped his powerful body with great fervor, taking each toe in my mouth and sucking their generous length as if they were, everyone of them, miniature cocks. I pressed my lips firmly against the soles ... Continue»
Posted by RazedGlory68 4 years ago  |  Categories: Anal, Gay Male, Interracial Sex  |  
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A COMEDY OF ERRORS......LONG VERSION

Chapter 1 - The Gift

Beth's mother looked at the box neatly wrapped in gold foil on the table. Why was Mark sending her a gift? She finally concluded that it must be a thank you for having him for Thanksgiving. It was so sweet of her daughter's fiancé to make such a nice gesture. She thought about calling Beth, but decided she would tell her this weekend at her birthday party.

Linda Franks would have waited for her husband before she opened it, but he was working late as usual. Besides, she was curious. She opened the card and it confirmed her suspicion. It was a very nice note from Mark... Continue»
Posted by sexaddict66 4 years ago  |  Categories: Hardcore, Mature, Taboo  |  
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Hot Retreat with my Nephew

I had always had strained relations with my b*****r growing up, and little changed as we got older. However, he got married and had a son, my nephew, whom I have grown quite attached to as he’s gotten older. I actually didn’t see him much when he was younger, which made it easier to find him so attractive now that he was 19. As he started resenting my b*****r for generally being a dick, he started to hang out more with me. I was single and had more time, and now that he was on the fence about college and wanted to focus more on simply having fun, I took the opportunity of inviting him to g... Continue»
Posted by cockonce 3 years ago  |  Categories: Gay Male  |  
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Confessions of an anal addict

Anal is all I think about and its all I want.

For as long as I can remember I have been drawn to the backside. For me its the ultimate sexual feature on the body. In fact its a thing of beauty and something that I would regard as art. What makes it so glorious is that hidden between these two mounds of perfectly formed flesh and muscle lies that small, dark, exquisitly beautifull backdoor love tunnel.

When I was in my teens I use to love wearing silk or smooth feeling underwear that I would buy a few sizes to small for me so that when I put them on they would fill up the crack between my... Continue»
Posted by analaddick 4 years ago  |  Categories: Anal, Gay Male  |  
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The niece 5 – Shower with mom


In my last installment, I shared a special event that happened while my niece was feeding her baby. This ended with the weirdest sentence she had ever told me. She had mentioned that I might be surprised to what my s****r, her mom, might be opened to. 

I left it at that. My s****r, as I said, is probably the straightest gal I know.

Divorced, she had never remarried, probably dated a few times but I’m sure that was it. Now my s****r is nobody’s fantasy. While she’s pretty, she’s bone thin, and wears a bra only because this is what women do. I’ve seen her in bathing suits and housecoats a... Continue»
Posted by Ticlem69 4 years ago  |  Categories: Taboo  |  
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