Shemales Porn Stories
Page 68

Dirty Tranny gang bang

Deep breath Charlotte, step into the night air and strut your stuff girl.

This is what I was born to do; I snuggle into my short white fleecy coat as my 5” platform heels click on the pavement. Glancing down I can see my shapely stocking clad legs and, the all important, ankle bracelet glitter in the light reflected from the street lamps.

It is not quite 8 pm as I walk the short distance from my hotel to the pre-arranged meeting place just outside the pub near Tower Bridge.

Two men walk past; mid thirties and well dressed, they have both been looking at me for some time,... Continue»
Posted by charlottekerscot 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1169  |  
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She wanted to Watch!

Everyone knows I'm bi and a Transvestite. I don't dress as much as I wish but I do go out two or three times a week. When I'm not dressed up I tend to hang at a straight redneck bar thats about two blocks from my house. They all know both mark and Kristy there and most are nice to me and respect me because of the respect I give to them.

Well yesterday I was in after work for a couple beers and Cindy the bartender and Lisa wanted me to do some drinks with them. Orange Crushes, wow I didn't want to get d***k cause I had plans for Kristy to go out clubbing. But after encou... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  Views: 1166  |  
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unnecessary roughness

Some years back, I was on an overnight business trip. I would often crossdress in my motel room to entertain myself and practice looking sexy. I could pass as a real woman from a distance but not so much up close. I'd been strutting around in a short a****l print dress and platform heels, admiring myself in the mirror and occasionally walking around outside my room in the motel parking lot. There was a convenience store/gas station next to the motel, and I kept walking over toward it, daring to be seen by people filling their tanks, etc. Late that night I decided that I just had to go over to ... Continue»
Posted by dana213 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 1165  |  
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A Walk after a Busted Date part 2 OR My First Day

A Walk after a Busted Date part 2 OR My First Day as a Hooker part 2

Toot-toot!

Crap that scared me! I wasn't expecting anyone to try to pick me up again. I thought it would have been a fluke. A one-off earlier with the k** and the handjob. Really?

Again? I can't say that I'm not flattered. I was, really. Gathering my nerves before turning to see who my next suitor was, I slowly turned without my legs shaking so much this time. Whomever was in the car, they would see me as fairly confident hooker walking the street.

Leaning on the passenger door of the Lincoln gave me a vie... Continue»
Posted by LeslieStone 1 year ago  |  Categories: First Time, Hardcore, Shemales  |  Views: 1162  |  
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A Different Kind of Woman pt2

My hands were at one and eleven o'clock tied to the bed, the beautiful creature that I was so infatuated with turned out to be a shemale and I was at her/his mercy. Tiffany was working her/his penis up my butt with precision all the while stroking my penis keeping me rigid hard. Each time I thought I was about to shoot Tiffany would stop long enough for me to calm down.
Tiffany had called some body named 'Joliet' and told her(?) to bring 'Bambi' with her(?). Tiffany was having her/his self a fantasy come true pumping her/his penis deep into my butt, all I could do was grunt and groan with... Continue»
Posted by d4david 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1161  |  
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A Sissy Slave for a Transvestite...continuation

Gwen took hold of my head and guided her penis to my lips and pressed her pre-cum oozing head against them. Gwen said tenderly, almost panting '...come now open those lips and let me in, we both are going to enjoy this...' Helpless and at her mercy, I opened my lips and allowed Gwen to slide her monstrous penile head and shaft into my oral cavity. Gwendolyn slid her penis into my mouth, her legs started to trembled as she gasp and took short quick breaths. She pulled her penis back slowly till only the head was still behind my teeth.

Gwendolyn gasp saying '...oh baby, yes that's just what... Continue»
Posted by d4david 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  Views: 1161  |  
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Working late

This story follows on from my last story “On the Road”

Working Late.

Dannielle had been woken by a call from Paul asking her to come into work early as they had some figures to go over. She knew what that meant, a quick fuck before work. As she was getting ready she remembered what those builders had said yesterday, the photos they had taken and the note they had left. “Wonder if they where actually going to come to her work and find her if she did’t get in touch” she thought as she got ready. It wouldn’t be that bad, she had fun with them and she loved Johns cock. “Bet they where just p... Continue»
Posted by danni1 3 years ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1160  |  
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The Lion, The Bitch, and the fucking Wardrobe.

I guess I have always been a sissy. I started crossdressing at a young age and it gave me such a wonderful feeling that I struggle to form the correct words to describe the way it makes me feel. It just felt right, and ohh so sexy! Like I said, I have always been sort of a sissy, and my father couldn't have been less plesed. I think he had his suspicions that I might be, uhhh... different before he found my lingerie and stilleto shoes, but once he knew for sure thats the first time he hit me. He made me promise, at pain of... pain, that I would never do any of "that faggot shit" again.
... Continue»
Posted by redk1 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1160  |  
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Becoming Linda


I am in my late teens with a very feminine side that I started discovering much earlier. I live with my s****r, my mom whose a workaholic, and my stepfather John who is caucasian.
I am Chinese-American, 5 feet, 4 inches tall with a nice, completely hairless body except my pubic area and under my armpits. My body is a bit on the full side, and I have long, thick and soft black hair that I keep in a pony tail. According to my s****r, I have the greatest butt any girl would die to have, and I tend to agree with her as I look at my profile in the mirror, especially when I wear her undies. I hav... Continue»
Posted by cocksucker1966 6 months ago  |  Categories: Shemales  |  Views: 1160  |  
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My First TV Cottaging Fun

My first time (And this is Genuine, I assure you)

I dressed under my normal clothes and took a rucksack with other bit's & pieces in and went to a nearby "Cottage" that had 2 Glory Holes, when I got there, it was empty, so I went in the middle cubicle, finished dressing: Stockings & Suspenders, High Heeled Lace up PVC Boots, PVC Basque etc.

I didn't have to wait long, the cubicle's then got occupied either side, through the peep holes in the door, I could see at least 2 other guys at the urinals.

Then I saw fingers appearing at the hole to my left, I looked through the hole on my rig... Continue»
Posted by uktvmaid 8 months ago  |  Categories: Group Sex, Mature, Shemales  |  Views: 1155  |  
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made me a slut.

I spent my time online since I was 18 watching tranny porn and crossdresser porn I really enjoy a mix of both especially with a big black cock in between I found a movie with a ebony tranny with a big cock and a white sissy gurl with a nice sized cock also... They got dolled up together and all of a sudden they were smearing each others make up on each others cocks... The things I saw that happened to that sissy was some of the hottest things I have ever seen... After this video I couldn't just go back to regular porn or continue searching online to watch videos, none matched up... So I starte... Continue»
Posted by reefermcrevolver 2 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  Views: 1150  |  
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The Making of A Sissy-Part Two

As Bella blossomed physically, Jane ensured the girls took control of her; she was made to know her place amongst females and was still subjected to their choosing her outfits. Bella was habitually made to pose before a full length mirror as Jane and the girls scrutinised her feminine shape; the girls were especially pleased on those occasions when Bella was held naked before the mirror as they stroked and admired her sweet white thighs and bottom, cupped her deliciously formed breasts; the smiling girls actions making Bella’s sissy hairless cock rise with excitement. This gave Tara licence ... Continue»
Posted by midsummerman 2 years ago  |  Categories: Fetish, Shemales, Voyeur  |  Views: 1146  |  
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Morning Routine at the Mansion of My Misstress


My eyes open with the gentle humming of my small alarm clock. I quickly shut it off so as not to disturb anyone else in the room. Its 4:30am, well before light creeps into the day and the room is now pitch black. Very quietly I rise up on my hands and knees and crawl off of the small doggy bed on the floor next to the big bed. It‘s embroidered with my name “Heather” in pink because it’s my bed and I’m the pet of my Mistress.

I’m silent when I move because I have done this so many times before. On all fours I make my way to the master bathroom and gently close the door behind me. I then st... Continue»
Posted by heatherlingerie 3 years ago  |  Categories: Fetish, Shemales  |  Views: 1142  |  
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xmas pet

Please see my first blog for background info: http://xhamster.com/user/p1llow/posts/18252.html

* * * * *

I never got anything from my father for xmas or bday since I started leaning toward my feminine side. I knew something is strange when I got up on xmas morning and saw some presents. He does buy me clothes he sometimes wants me to wear at home but that's never a gift - more like a strange punishment (or at least he thinks he's punishing me most of the time). I was too afraid to open them before he wakes up, they might not be for me after all, so I did my chores around the house until ... Continue»
Posted by p1llow 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 1142  |  
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Back to the shitty date which ended up not so shit

I straddled Ron, the black hung stallion and impaled myself on that huge cock. I slid the whole length of that massive shaft swallowed that shit up, til I felt it in my lungs. It must have felt good because his eyes got all googly watching me take that black dick all the up inside me! It felt soo deep pulsating inside me!

then WTF? Andre, starts to straddle his face and get rimmed by Ron! I knew these fuckers were fags, and that really fucking turn me on! Not because I'm into gay sex or anything. Just into the possibilities it presents!!!! I start to grab his balls and stroke dre's ... Continue»
Posted by sataori_fukame 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1140  |  
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Tranny Gang Bang

Gang Banged
I stood there looking in the full length mirror very pleased with the image I saw. I was ready for the evening and the first time I would be with more than two men at once. Freddy, had talk me into doing him and two of his friends in a sleaze motel.

Freddy had found me on my internet messenger. We had chatted for a long time and meant twice. Once at a small lake in a subdivision near where I lived. An Italian man about 40 with a bit above average dick. It was so exciting to get screwed in the shrubs around the lake’s edge with the lights from the houses softly illumining ... Continue»
Posted by littleoralvee 2 years ago  |  Categories: Group Sex, Shemales  |  Views: 1137  |  
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5 COURSE MEAL

There are a group of people I regularlly swing with. This 1 night I got a phone call from one of the women named Susan who asked me if I would like to come over. She told me sh had a few friends over and they wanted some fun. None of their husbands were there. I asked susan if I could bring a friend and she said of course. She knew who exactly I was going to bring, mt t/s girlfriend. We got there and we all starting talking. Everyone was so horney that my friend went right over to one of the women named Nancy and started to feel her up. Nancy reached down expecting to feel a pussy but instead ... Continue»
Posted by firefighteral276 2 years ago  |  Categories: Lesbian Sex, Shemales, Taboo  |  Views: 1136  |  
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Lisa at last

My phone buzzed “in the parking lot” was the text. “Meet me at the side door” I quickly texted back. It was dark out as I opened the door and Lisa slid past. She followed me in silence as we went down the hall and I opened my room door. As I closed the door we paused looking at each other. She had long dark shoulder length hair, dark black eyebrows. Her brown eyes were sexy circled with dark black mascara and eyelashes. her lips were a mild pink, her neck had a dark black choker and she wore a necklace with a black heart. She was in a cute black dress that just covered her small chest with sh... Continue»
Posted by iheartm2f 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 1135  |  
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The Fanncy **Dress** Party

I went to a Priests and Prostitutes party a short while ago in South Africa and loved getting dressed up as a prostitute, it was so much fun and It made me really horny.

I had to get a cab dressed up like this and we all met in a bar before hand. I was the first one to arrive at the bar which was already packed as it was a Friday night and the early (going home from work) crowd had not left. I sat quietly at a table and ordered a double Vodka and Tonic and was watching the door hoping that someone else from the party would come to assist me. I must have been sitting there for 10 minutes an... Continue»
Posted by africangraham 2 years ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  Views: 1132  |  
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White sissy tp black man

On the bed in the guest room, Jamie lay back against the flowered pillows, feeling pretty in his pink satin nightie, his stockinged legs spread wide, and the long black vibrator pressed to the mound in his panties that betrayed his tied-back cock. He slid the straps of the nightie off his shoulders and pulled one pale little tittie out a frilly lace-lined cup. He squeezed the small sensitive nipple and took the vibrator off his already wet panties and placed it instead against his tight asshole.

"Oohhh…" he moaned, licking the raspberry lipstick off his lips.

He opened his made-up eyes a... Continue»
Posted by jeffreybarnes 1 year ago  |  Categories: BDSM, Interracial Sex, Shemales  |  Views: 1132  |  
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