Shemales Porn Stories
Page 114

FIRST TIME WHORIN'

FIRST TIME WHORIN'

I was just 18 when I went out whorin' for the first time. It was something I had an overwhelming urge to do after fantasising it countless times. I had been painting up and dressing since I was 13 and my 18 month older b*****r had been fucking me regularly since I was seven until he went away in the Army when I was 16, plus I had been shoving all types of objects in my pussy almost daily. My desire to have my pussy ravaged was insatiable. I used cucumbers and even a slender long Japanese eggplant about two inches in diameter, fantasizing it was a BBC. I reveled as I watc... Continue»
Posted by tvsllutmichelle 22 days ago  |  Categories: Anal, Hardcore, Shemales  |  
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How it all Started....

Back in 1997 I was living in my dads place a condo on the beach.In the summers I had a friend come down from new york with her f****y. She was 3 yrs older then i was.I loved going to the jacuzzi the building had by the pool. one day I was seating in there and her grandfather and she came in. we where all in the hot water and i feel as where talking my foot being played with. after a while the foot got higher un till it was almost at my thigh inside my trunks. I got hard. I must of been twelve or so....As my friend get up to go to her towel. I figure out that It wasnt her, that was doing it.. ... Continue»
Posted by lucifer696 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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the first tranny I looked for

So i've had some tranny experience unwittingly. I respond to this ad on craigslist from this 19 year old tranny who lives fairly far away, but her picture was so sexy I decided to take the hour drive. So I drive to her parents house, nervous the whole way, when I get there I get out of the car. Stone sober, knock on the door and this little hottie answers. Black and white floral blouse, visible cleavage, tight little leather shorts and a bubble but that would make real girls jealous and about 5'3". She invites me in, she shows me around the house offers me a drink, we go around to the back whe... Continue»
Posted by hothothot103 2 years ago  |  Categories: Anal, Shemales, Taboo  |  
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My sexual fantasies



Well, I've always had sexual fantasies, since I was very young, I discovered the joys of masturbation around the age of 8, I remember playing in my bedroom with my pillow, I imagined it as a woman, or something like that, and so I took the pillow and I put it between my legs, rubbing my little cock against the pillow in a sensual movement, thinking about dirty things, until I reached the orgasm and jizzed over the pillow, it was so exciting for me and I enjoyed very much those situations. I remember several afternoons playing with one friend of mine in the staircases of my condominium, we ... Continue»
Posted by Porcellone 3 years ago  |  Categories: Masturbation, Shemales, Taboo  |  
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James

"James, stay out of my room or you'll be sorry!" Julia retorted.
I looked at my older s****r and hung my head. I had been caught
again in her room, looking in her dresser drawer. I was 9 years
old and had become very curious about girls. They had started
becoming a subject of my interest about six months ago, and my
two s****rs were a handy way to study the new subject of my
interest. "James - are you listening to me? I don't like it when
I find you doing these things. I don't go through your room, and
I want you to stay out of mine!" Julia really looked angry. "OK,
OK s*s, I got your... Continue»
Posted by alexwd0 4 years ago  |  Categories: Shemales  |  
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first time with a shemale

Well this is my first story i have wrote so bear with me and comment on what you think...

well this all happened about two years ago when i was 18 i always have had fantasies of having a cock in my mouth and ass but i wasnt attratced to men jusst the cock so i decided to find a shemale. i live in a small town and thats hard so i found one about an.hour away in the city. so i talked to her decided to leave work early i was already horny anways but the worst part was the drive because it gave me time to think and second guess myself but i kept going..
when i arrived there she was waiting ... Continue»
Posted by wildmanxd 2 years ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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Young Master Ch. 01

It was supposed to be the best day of my life...and maybe it was, but definitely not in the way I planned.

My 21st birthday...my first day as a man, as a true lord of the Manor...my first day as a Master. I was so nervous I threw up my lunch. Not very manly, I know, but just the thought of having my very own sissy to play with had me teetering between the giddy excitement of a k** right about to open the biggest present under the tree, and the stark terror of officially being a man in my step-father's eyes...how could I measure up to him? I felt destined to disappoint him...and I didn't eve... Continue»
Posted by bi_hengst 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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A First Time Out

I'd always fantasized about going out to a bar or a club, dressed as a woman, and after a few drinks managed to find the courage to do so. By the end of the bottle of wine I was dressed up and ready to go, suspenders, stockings, a corset on so tight it was hard to breathe underneath a loose, knee length skirt and close fitting top. My make up was done, a touch up of lipstick after the long black wig had been smoothed down and the last of the wine polished off.

I'm always told I look gorgeous when I dress up, but I'd never been out before. Before it had just been for other people in private,... Continue»
Posted by amylee-jones 9 months ago  |  Categories: First Time, Shemales  |  
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BECOMING MY BOSS MARGO'S SISSY BITCH BOY TOY.

WHEN I GOT CAUGHT GIVING A SUPPOSEIDLY QUICKIE BJ IN THE MENS ROOM STALL TO A CO-WORKER OF MINE, I WAS SURE MY FIVE YEAR JOB AS AN UNDERWRITER AT MY INSURANCE COMPANY WAS A THING OF THE PAST. LUCKY FOR ME, THE GUY I WAS PLAYING WITH WAS ONE OF THE OWNERS NEPHEWS, SO I WAS CAREFULLY TRANSFERRED INTO AN NEW POSITION ON THE SIXTH FLOOR AS THE ONLY MALE IN A SEVEN PERSON RESEARCH TEAM. MY NEW BOSS WAS AN OLDER (LATE 40'S)VERY CONSERVITIVE WOMAN NAMED JOAN. FOR THOSE FIRST TWO WEEKS, I WORKED LONG AND HARD IN ATTEMPTS TO NOT ONLY REDEEM MYSELF, BUT TO FALL INTO HER GOOD GRACES AS WELL. JOAN ... Continue»
Posted by cddixie 4 months ago  |  Categories: First Time, Shemales, Taboo  |  
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I slept with Joanne, who had a dark secret

What is the weirdest sex I have had, I thought about is for all of thirty seconds, the night Joanne slipped inside me, on a f***ed stopover.
Now before you cry Lesbian or Bi-Sexual, you would be wrong, because Joanne was neither, she was a transsexual, something I did not know at the time, nor was she, him about to admit to, especially since I had offered to share my hotel room and not leave her stranded without.
We both worked for the same airline, which I shall not mention, due to legal obligations, but I knew Joanne from our first meeting her on a photo shoot, which was an advertisement a... Continue»
Posted by MarieL 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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Bar trap

Bar trap
By slut michelle

Steven was a dead-normal guy. At the age of 28, he felt very happy.
Everything had developed in the last few years like he always wanted it
to be. His job in a big insurance company was secure with an outlook of
a promotion in the next year. His partner, Nancy, was a very ambitious
lawyer. That meant some days with long working hours for her. But as
Steven was quite proud of her, being so successful in her job, and
because they still had enough time for each other left, he didn't
complain. Steven met Nancy shortly after both of them had left Uni. It
wasn't... Continue»
Posted by trans_michelle 3 years ago  |  Categories: Anal, BDSM, Shemales  |  
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The experiment

I'll admit that I was a little bit d***k when she sat down beside me at the hotel bar.

Another business trip, away from home, this was getting to be a drag, and sipping on some bourbon helped a little. The smell of her perfume as she sat down snapped me out of my haze, and I looked at her. She smiled, turned to the bartender and ordered a drink. Looking back at me, she said "Can I freshen your's up too, darling?" I must have looked like an idiot, staring dumbfounded at her. I looked down at my glass, then back to her and said "sure." Her voice was surprisingly deep, but she was pretty. I ... Continue»
Posted by abend 4 years ago  |  Categories: Anal, Fetish, Shemales  |  
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I am such a slut........7

I am such a slut........7


I couldnt believe that this was happening. I was so excited that I was shaking. I could hardly breathe. My first, my first real date dressed as a woman. I had met him over the internet on craigslist. We had talked. Exchanged pictures. And tonight, tonight was the night. I had checked into the hotel around five and began preparing. I laid my clothes out on the bed. My white panties trimmed in lace and my white thigh highs. My four inche white heels, open toed that would show off my pedicure and my pink toenail polish. A white lacy bra to push up my small breasts... Continue»
Posted by snuggle11 4 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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shemale experience (Fantasy wish it was true!)

So here I am sitting at the sherries accross from my hotel.Eyeing a good looking blond girl, she looks about 21, nice little bubble butt,hips and D tittys,very pretty. she catch's me looking at her and give's me a wink, I make it a point to chat her up(while being intoxicated by her strange happy attraction)I end up talking her into coming back to my hotel for a swim,after of course I get her a bikini at the store down the street. we end up back at the room and we talk and begin to make out,she goe's and changes we go for a dip and things get hot so we head back.....

At this point I can't ... Continue»
Posted by tonkier101 2 years ago  |  Categories: Anal, Shemales  |  
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Something more to her, part 1

Something more to her, part 1


jasmine had just left the local club and was walking to her favorit street corner. jasmine had an IV league education, was extremely beautifull, having dark tanned skin, having 34 DD breasts, a perfect figure, and perfectly done honey blonde hair. she was smart, sexy, and she was one of the most charming people she knew. so why was she selling herself on a street corner? the reason was simply becuase it pleased her as much as it pleased her customers. she may have convinced herself it was becuase she couldnt find a man that would except her 10 inch "secret" t... Continue»
Posted by mj2397 3 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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Milking Time B3 Chapter 2 Barocca Confronts Ebony

Chapter 2: Barocca Confronts Ebony

Barocca and Ebony sat together in Barocca's quarters, watching a delayed video broadcast of the final moments of Jordan finishing her afternoon of sex with Clyda. As the final scene came to an end, Barocca pressed the button on the remote control and turned off the monitor. She let the remote land loudly on the end table next to her.
"I don't believe it. I simply can't fucking believe it!" exclaimed Barocca. "Neither you or Clyda could manage to put that little slut away, and get her ass carted off the Island."
"What is your problem, girl?" asked E... Continue»
Posted by gregster 2 years ago  |  Categories: Hardcore, Lesbian Sex, Shemales  |  
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My day with Maggie

I kissed my wife jumped in the car. As I turned out of the driveway I dialed in work and called in sick for the day. As I drove to Maggie's I could feel my rock hard cock beg for relief. I tried not to think about it but my cock stayed hard the entire drive. As I pulled into the hotel and walked to the room number she had text me I felt nervous, excited and so horny all at the same time. No matter how many times we have sneak off together I always feel the same. Maggie opened the door and I quickly slid into the room put my arms around her as our lips touched. The kissing turned to passion as ... Continue»
Posted by iheartm2f 11 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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The Politics of Dancing

"What the fuck are we doing here. Seriously?" I growled in his ear. I was still smiling, and I doubt anyone was going to be lip reading.

We were on the dance floor, my arms around his neck, slowly swaying to a crappy Lawrence Welk-wanna be band.

"You know what we're doing here, darling." His reply was sugar coated, sappy with his big grin. And why shouldn't he be smiling. He was dancing with the most beautiful woman in the place. The men were obviously jealous of his new trophy wife, and the women were too polite and too mannered to say anything directly, but their eyes said it al... Continue»
Posted by TransContinental 9 months ago  |  Categories: Shemales  |  
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BBC "GIANT" David

this is for my huge ultra hung super strong friend too2badd David

It was the morning i would meet the biggest man i ever mett ,A huge hulking black man who hada huge hard on ever since we met and is as hot for me as i am for him not only is he hung bigger than a bull but is way taller than any one else nearly twice my tiny five feet zero tall and his cock goes on forever long and thicker than my fore arm.
I stood loking in the mirror as i aplied my whoreish make up and slipped on my tight white silk panties god i was having trouble already with my big throbbing hard clit in anticipation of... Continue»
Posted by huge_cock_rules 3 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Little Public Stripper

I walked across the nightclub floor, two female friends either side of me. My short red dress looked perfect with my red patent heels, and my ass and g-string showed below the hemline. My skin felt alive, smooth and shaved and tingling, ready for this experience. The matte gloss of my long, black 1950’s style hair style (an expensive, convincing wig) picked up the pink and purple lights of the club, and I felt everything below my waist relax as it prepared for the sexual treat. Eyes were on me, desiring me. Girls and men alike looked my way, the women celebrating my liberation with me, the men... Continue»
Posted by CD_CutieBoi 2 years ago  |  Categories: Fetish, Shemales  |  
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