Shemales Porn Stories

Josie's Awakening

My name is Joseph, and this is a wonderful trip down memory lane for me. Join me as I relive the first few experiences of what would soon become a life changing event......

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Jason and I were always best friends. We grew up together, we played sports together, we got laid at practically the same time by another pair of best friends, everything. This is our story......

I was out of town for a few weeks on business so we hadn’t had a chance to hang out for a while, so once I got back into town I called him up to see what he was up to
"Hey man what’s up"
"Nothin, my s****r is... Continue»
Posted by qqqqq2qq 5 hours ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 608  |  
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my Tranny Bud

I am straight. ok, so a couple years back after the divorce, had to go live with my b*****r. he gave me a little front room and I can never repay him for that. I had a female friend who's b*****r was a tranny. I wanted some hydro he sold. so called my friend to send her b*****r tranny over. he came after 1am. my b*****r was crashed. we smoked a little and talked about past experiences. obviously his were way more exciting. I mentioned that I loved to jack off in front of my wife while she was watching PORN, drove her crazy. ok got late, so he split.

3 months laters I was able to afford my... Continue»
Posted by flashmetal 17 hours ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 1513  |  
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LOOKING FOR KIETH IN TENNEESEE

WOW!!! i cant believe its been 15 years now..... meeting "kieth" changed my life forever!!!! hopefully, sumday i will be able to tell you the complete story in detail,... cas it will take awhile to tell... to this day, im "still" looking for him... ill probally never find or see him again... i met kieth 15 years ago... it was a one day thing.. i was hitch hiking... he picked me up in tenneesee... and along the way, he asked me to hav sex with him... and he was cute and i was horny anyways, so i said yea!! lets go sumwhere... and he took me to a place out in the woods that he knew... Continue»
Posted by 3DXXXSHEMALE 18 hours ago  |  Categories: First Time, Masturbation, Shemales  |  Views: 418

I never thought I would

I was asked a Truth or Dare about my sexiest fuck. Well this is I guess one of the sexiest moments of my life as I never expected it to happen.

OK, there have been a few and my favourite changes with my mood. So one evening I was having a drink at my local. I was sitting next to a guy who was fun and we joked and laughed. As it got to closing time he asked me if we could perhaps go back to his place for a drink. There was no suggestion of anything odd, he was just an ordinary guy in an ordinary pub and I certainly didn't fancy him. Anyway we went back to his place, a small flat in town. He ... Continue»
Posted by uniqelyme57 1 day ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1298  |  
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Losing my Cherry

Although l have been secretly cross dressing for years I have never took it beyond the confines of my bedroom or hotel room. Well I have been really wanting to take this to the next level. So as I was traveling on business this past week I answered an ad on Craigslist for a massage in my hotel room from a male masseur I made the appointment and waited with anticipation for my masseur to arrive. At promptly 8:00 there was a knock on the door and when I answered there was Chris a very handsome young man, I invited him in and he promptly set up his table..
As he was setting up his table and ... Continue»
Posted by mikkas72 1 day ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 2028  |  
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Lexie's Fantasy Day With Mr. Green

Lexie's Fantasy Day With Mr. Green

Here’s a fantasy from one of my sissy readers…

….sitting on a couch together, holding hands. Your hand then finds my knees, encased with sheer stockings, as you gently rub at them. Then slipping your hand under my satiny white dress you go higher up my legs as I lay my head on your shoulder, smiling at you demurely as you inch up to the silky spot where my excitement is bursting forth. We lean into each other for a soft kiss as you taste my lipstick. Our tongues intertwine as our soft kiss has become a full open mouth ravenous kiss revealing ou... Continue»
Posted by porngent 1 day ago  |  Categories: Fetish, Shemales  |  Views: 278  |  
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I wish I Could Be A Beautiful Soft Submissive Girl

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I So Wish I Would Have Been Born With a Female Body
I Envy Women and So Wish I Could Be A Beautiful, Soft, Submissive Girl I love to watch xxx adult films. Mainly, because I love to watch heavily hung male studs do the things they do to women. Most of the women in the adult films are beautiful and I wish I could be the girl. Watching a woman allowing a man to penetrate her and take full advantage of her feminine charms is thrilling, and I would happily trade places... Continue»
Posted by estephania 1 day ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 482  |  
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T-Girl University

Jason was apprehensive about starting college, as any freshman would be. His high school girlfriend, Becky, whom he loved dearly, was going to a different college on the opposite side of the country. They had to promised to stay together but Jason was worried; there would be a lot of temptation for her from all those west-coast surfer dudes. He hoped she wouldn’t forget him and made a vow to himself to stay faithful no matter what. But there would plenty of temptation for him as well: Jason was going to a small northeastern college that, until recently, had been an all girls school. Jason’s in... Continue»
Posted by slatemhor 2 days ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 3605  |  
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Love my brother-in-law

As Brian slammed his cock in and out of Sally’s pussy, she constantly groaned with pleasure, as her tits swayed with every thrust Brian spanked his wife’s buttocks, Sally said she was Cumming and with a ear piercing scream she orgasmed, like mad Brian gripped her hips and drove deep, before filling his young wife’s pussy, collapsing on the bed unable to speak, they had made love nearly all night, as it would be nearly a month before Brian returned home from a business trip, getting in the shower Brian run his hands over Sally’s sexy smooth body, her ample breasts, filled his large hands, playi... Continue»
Posted by rodma 2 days ago  |  Categories: Lesbian Sex, Masturbation, Shemales  |  Views: 2478  |  
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Letting it all "hang out" 2

A new turn in my life.

One of the things I love about younger guys, is even after
shooting their loads, their cocks still stay somewhat
hard. Jack's cock in my ass, stayed nice and hard so he started
to slowly move his hips forcing his cock to push his cum out
of my ass.


Bob said, don't waste it. Jack stopped, reached over,
grabbed a towel and as his cock slipped out of my ass he replaced
it with the towel.


I climbed out of the jacuzzi, Bob stood up and followed me
into my bedroom. I climbed onto my bed on my hands and knees
wiggling my ass in the air.


Bob knelt down ... Continue»
Posted by Bigrodtaz 2 days ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 767  |  
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Letting it all "hang out" 3

This is a continuation of previous stories, it includes
homosexual and transsexual activities. If it's not
your cup of tea, I respect that but don't read it and
leave mean and nasty comments.





Kelly and I had just sucked each others cocks, exploding
down the others throats. My finger had been slowly encircling
her rosebud. She stopped me, turned and slithered up my
body until our cocks were touching. She looked at me in my
eyes, smiled, slid up some more until we could look directly
into each others eyes. Our lips met, just lightly at first,
I could taste my cum still on her... Continue»
Posted by Bigrodtaz 2 days ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 563  |  
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Sharon's Mistress Throws a Sissy Party

Sharon’s Mistress throws a Sissy Party
(Prior chapter is Sharon’s Sissy Saturday)

The next morning Mistress was kind enough to let me sl**p in, but an alarm above the door to my little cell went off at 6:30, rousing me from a delicious dream of being naked and fucked in the woods by a handsome, dark-haired man who kept me as his personal sissy slave slut. I woke with the sensation of his hard cock filling my dripping pussy, and I realized I was still leaking cum from my day in the booth. I crawled from my cell and saw a note from Mistress Angela telling me not to wash up but to dres... Continue»
Posted by scatpetsmaster 3 days ago  |  Categories: Fetish, Shemales  |  Views: 1522  |  
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The Bachelor Party

This is one of those stories that just popped into my head after looking at a friend's pictures of a bachelor party he had recently been to. I would welcome any feed back to this story.

What started out to be a normal bachelor party couldn't have turned out to be any less normal than the one I attended last year. I was a friend of a friend so I can't say that I knew the groom or all of the guys there, but I'm an easy going guy and as the beer started to flow of course we all became fast friends.

The word at the party was that there were some strippers coming over later and we were all ... Continue»
Posted by slatemhor 3 days ago  |  Categories: Anal, Shemales  |  Views: 1839  |  
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Halloween Pt4

(If you haven't read Halloween Parts 1-4, you'll have no idea what's going on. Except for sex.)

He broke off the conversation with the guy he was next to, and strode purposefully toward me, a cup in each hand.

"Where you going, Baby?"

Colette tried to intercede. "She's going home?" she said, with the sentence starting out f***efully, but ending on a high note,

so it sounded like a question. It was obvious he was ignoring her completely.

"I said, I'd be right back. I was just going to get us something to drink." He held up his left hand, to indicate it was for me.

Not ... Continue»
Posted by TransContinental 3 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 580  |  
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chase the pool boy (fictional)

after the thunderstorm and hurricane wreaked havoc on our town, and we had a lot of damage, my house was repaired but my pool was full of crap from the hurricane, no one could come out and help, everything was pretty much shut down, food was being dropped in by helicopter.
well finally, everything began to fall in place, but my pool still needed work, so my neighbor lisa(the shemale) came over and and said her friend was staying with her due to the death of his father, and knew a lot about pool cleaning and we worked out a price for the next day. i awoke about 6am and went into the kitchen ... Continue»
Posted by rollpayer1105 3 days ago  |  Categories: Gay Male, Shemales  |  Views: 627  |  
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My TS Mistress


It is night time and I am lying on my side in the bed. I am naked wearing just 3 silicon cock rings. I try not to touch myself. Earlier Mistress had told me to go up to our bed and wait for her. I did as she said.
I could hear her with her submissive for the night. A married man...well, another married man. Getting his kicks from my Mistress doing things to him. She never does sex with them. Most into just being abused and such. I was f***ed to watch one time she was with a client. I had been secured to the wall with chains and an anal hook inserted inside me. My cock was free to hang but i... Continue»
Posted by bottomguy757 4 days ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1295  |  
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Missed You

The gate agent walked down the jet way unhappy to share the news. She conferred with the flight attendant. The obviously gay young man phoned the pilots. Next the woman announced, “Ladies & gentlemen, this flight has been canceled. We need for you to gather your belongings and exit the plane. We can re-book you on another flight at the customer service desk.”

Nearly every passenger grumbled with disgust. Left with no other choice, they grabbed their bags and filed off the vessel.

Jessica Stewart waited patiently conversing with other unhappy travelers when an airline employee appeared sa... Continue»
Posted by faggyboi 4 days ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 1008  |  
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Fucking a hot Sissy in the woods

Well, this is what got me into CD myself I guess. Despite getting off being the subbie from some men and women, I always liked girls, gurls and sissies. These I liked more from an angle of domination. So this beautiful early summer day I am out on the streets with my car, doing my "travelling salesman"-job. Taking a short break, I start browsing profiles in "gayromeo". I stumble over "Melinda23". The picture was only her chin and lipstick mouth and a sweet snub nose. She wrote that she's looking for a sensible, dominant man to explore the world and have a nice fuck :) She was obviously around ... Continue»
Posted by Cellboy1 4 days ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1216  |  
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Fun with the Mechanic

Last weekend, I had a date to go out to a bar with some other CDs in another state and a 2 hour drive. I would get dressed when I got to the motel. On the way I had car trouble, but kept driving to the motel. Told the girls who were already dressed that I couldn’t go to the bar or play because I could not relax knowing my car was having problems. I was so horny because we had set this date up a few weeks ago and I had spent the day trying on my new sexy short black dress and getting ready.

I left the girls at the motel and headed home with the car having transmission problems. On the ... Continue»
Posted by hotcdsub 5 days ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 6393  |  
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Sissy Sharon's Saturday

The day begins at 4:30 a.m.. I am awakened by the alarm next to my bed on the floor in my tiny cell. It’s barely big enough for the old mattress I have to sl**p on, but it has been my bedroom for the past 8 or 9 years (I’ve lost track). Every day is basically the same. I wake up and crawl from my room to the bathroom at the end of the hall in the basement. Cameras watch my every move, so trying to cheat by walking (ever) is a no-no. The punishment is far worse than the crime, so I am always obedient. In the bathroom I administer several enemas, being sure to expel all the nasty waste from my b... Continue»
Posted by scatpetsmaster 7 days ago  |  Categories: Anal, Fetish, Shemales  |  Views: 2022  |  
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