Shemales Porn Stories
Page 119

A Night to Remember

About six years ago just before Christmas I went to a transvestite bar in the centre Manchester after I had finished my act at a private party on the outskirts of the city. I was dressed in my sexiest outfit mini dress, suspenders, sheer stockings and 4-inch Fuck me hard stilettos, and my favourite long brown wig. I was fully made up with long false eyelashes and blue shadow, red painted finger nails, and dark red lipstick, pearl necklace and large chunky earrings. I looked quite stunning . I have a very good figure and long shapely legs. I need to, in my line of work, as a part-time tranny... Continue»
Posted by TgirlViki 4 years ago  |  Categories: Anal, BDSM, Shemales  |  
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First Real Cock i got

I must have been around 15 and it was during a carnival festival. Most of the boys were dressed as cowboys, super heroes, firemen etc. For me it was the chance i was looking for to dress up on woman's clothes.
I had picked up a mini dress, fishnet and a small top that was letting my belly free. I got a blonde wig (not the best quality) and tried to make up as good as i could. The result was not the best but for me it was huge.
I went down on the streets to walk without fear as everybody was dressed up, ended up with a friend of mine in a bar. He was dressed as an old granny!!!
After half ... Continue»
Posted by crazysissy 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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Walk his way

Just for the thrill of it all, I moisturized my freshly shaved body, combed out my long hair over my shoulders, and put on a pair of very short cut off denims, cuffed them even shorter, and a Betty Boop T shirt with the neck and sleeves cut out. I looked and felt very much on the fem side. Not really crossdressed, but without a doubt, sissified. I drove down the interstate to the nearest rest area and parked all the way at the end. I carried my little belly bag like a handbag, and walked to the rest rooms with a swish in my step and a grin on my face. Most people did a bit of a double take; a ... Continue»
Posted by dana213 5 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Jeffrey and Jayne

Jeffrey and Jayne

Jayne lay there awake again. She had Just looked at the clock and it was 2am, she had to be up for work in 4 hours! However much she tried to nod off she just couldn’t, she was far too frustrated.
It started when Jeffrey got home from work, as it always did.
She called “Hello sexy, I’ve run you a bath!” As he walked through the door, then “Tea will be 20 Minutes!”
All she got in reply was “I’m hungry and tired!”
He had a bath and then ate his tea in silence. After he had eaten she tried to snuggle up with him on the couch, then he put the football on and told ... Continue»
Posted by slave_ariana 4 years ago  |  Categories: Fetish, Shemales, Voyeur  |  
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The story of how i began crossdressing

This is copied from my blog http://cdcutiepie.tumblr.com, so the main updates will be there
i did think it would be nice to have it up here as well though :)

Entry #1:

I guess i was 17 years old and broke up with my first gf back then. barely had any sex, so was horny all the time :P


I decided to look online for couples and women who would be interested in camming with me, and a mistress responded to one of my advertisements on some swinger site (i cant remember why i actually registered there)

She told me she’s looking for a slave to entertain “them”
Thought it was a spelling... Continue»
Posted by CutiePie89 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
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First Time pt 3 by trans_love (Fiction)

Introduction: This is a true story that happened to me when I was a young "woman"

Here's another. Again, I was 13 at the time, I was 5' 2" , 105 lbs, long brown hair, green eyes, ass to die for, I stole my grandma's estrogen pills and started growing boobies, I was now a full b cup.

A couple weeks went by and I only seen my younger black guy a few times. He let me suck his big cock but that was it. One day he told me he met someone else and to not come around any more. As I turned the corner and was heading home his dad, James, pulled up along side me in his car. He said, "Jessica, why d... Continue»
Posted by 1superhornyguy 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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CD Maid Fantasy

Nervously, I knelt on the ground, and wait for Mistress to return. The whole day, I had spent cleaning her house, wearing my maid outfit, always making sure that everything on it was in order. It was difficult to keep the white stockings and gloves clean, but I had managed to do so, all while in 5" black heels, a lace-like maid outfit, and of course, a plug, collar, and cage to keep me from playing early. So I had finished my tasks, re applied my make-up, combed my short black, hair and had been on my knees for almost an hour: all as instructed. As it drew closer and closer to seven o'clock, I... Continue»
Posted by RosalynLee3 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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BBC fuck fests of Tgirl Barbie and Black Stud Ken

THE BBC ADVENTURES OF BBC SLUT TGIRL BARBIE AND HER BLACK STUD KEN

BBC FUCK FEST NO. 1, a continuing series


Starring Black Master Ken's thick, rock hard and irresistible BIG BLACK 8" MONSTER COCK

Featuring BBC sluts and lesbian Tgirls Mistress Barbie and her sex slave Tgirl Jill.

And a total stranger Big Black Bull wielding a BIG BLACK 12" MONSTER FUCKIN' COCK




Tgirl lesbians Mistress Barbie and her sex slave Jill are on a mission for Saturday night's BB8"C fuck fest with Black Stud Ken.

Their plan is to totally drain Ken's BIG BLACK BALLS of his lus... Continue»
Posted by tgirljillforbbc 1 year ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
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Summer affair with a latina ts mmmm

So, we all are busy and have our jobs n all and not much time for fun...So i'd thought ill try craig's list for the hell of it-which was something I would never have tried in a millions years lol. Jokingly I was repulsed by what i saw under the casual encounters but decided, "what the hell." I put up an ad with a toss away email saying something along the lines of 'big black juicy cock for horny latinas and white.' Mind you in the small town of Chico California i doubt any one would even check it, even left my cell number on there as well lol. So far, tons of spam, a few responses but they wer... Continue»
Posted by iluvtgurl 2 years ago  |  Categories: First Time, Shemales, Taboo  |  
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First blowjob (Part 3)

The next morning I awoke to something hitting me on the cheek. I opened my eyes and my "Daddy" had his hard dick out and was on the bed hitting me in the face with it. Without him prompting me, I wrapped my lips around it and began to suck. Once I got it into my mouth, he reached down to rub my little clitty through my panties.

This did not go on long when he yanked his cock from my mouth and demanded I take the panties off. While I removed my panties, he positioned himself between my legs. As soon as I got my panties off, he began to suck my little cock/clitty. After the session we h... Continue»
Posted by KaylaCD15 1 year ago  |  Categories: Gay Male, Shemales  |  
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summer vacation

hi my name is alex
and these is story is about, how i got my first taste of sperm.

it was the first week of summer holidays
i went to visit my grandmother, who lives in the north.
i took the train there, the cart was full first, but after several stops
i had it for myself.

i was really horny,so i looked around and saw i was really alone.
i took my dick out and started jerking it slowly.

as the time passed i got at my full size and i was pretty close to cumming.
the i heard a whisper behind me "hey boy, need any help"

i panicked and tried to hide my dick back into my pants .
... Continue»
Posted by readyCreampie 11 months ago  |  Categories: First Time, Shemales  |  
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A TGIRL FANTASY

For some time I've had a FANTASY of meeting up with a hot chick and bringing her home to have sex. After relaxing with a bottle of wine and getting aquainted we make our way to the bedroom. Turning the lights down low we beging undressing each other slowly as our passions rise. I lift her slinky dress over her head, she unfastens my pants letting the fall to the floor. I playfully touch her breasts covered by a lacy bra watching her nipples grow hard as she slips her hand inside my boxers. My cock begins to throb growing harder as she fondles me. I unsnap her bra and pull the straps off her sh... Continue»
Posted by querico44 5 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Me dressed as a Gurl

this happened about 25 years ago when i could half way pass i went to this night club for crossdresser, transexuals and transvestites west of balboa park one thursday night it wasn't has busy has on a friday or week end but there was a nice crowd mustly crossdressers a few trannys it was not to late about 8:30pm the company was fine mainly playing pool and looking around some good conversation us gurls we in back the guys were in front at the bar checking us out i was dressed to kill had on black 4" spiked heels with mesh stocking to my teights with a garter belt and black thong blac... Continue»
Posted by jackguns 5 years ago  |  Categories: Anal, Shemales  |  
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Always knock first!

As the title says, it is always best to knock on a closed door prior to going in to someone whom you know is in that room! My bad! Earlier this week, i went in to see my boss, a hot guy whom i have fantasied having sex with, to check on my hours scheduled to work , as a swim instrucor. i did not knock i just opened the door and walked in, and there he stood, holding on to his desk, looking at a pussy magazine, and just jacking his lovely huge cock, with a huge mushrrom head on it, and then he saw me, and he froze
He kept his hand still on his cock, and i just laughed so hard, which made him r... Continue»
Posted by cumsquirter 5 years ago  |  Categories: Shemales  |  
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Trolling 4 BBC's in My Younger Years

With the help of two drag queens and friends,I perfected my "Sheila" persona many years ago.I looked a lot like Nancy Allen when dressed.Out on the town,I was completely passable as a hot,fuckable woman.When trolling for my DARK DESIRES,I never failed to tell them that under the make-up I was a man.I never lie and I didn't want to get beat up.Just like in my "Black Cannon" story,I've had many pricks pressed against my thigh.Even after learning the truth,a lot of the straight black guys I was dancing with took me to the parking lot for some "quick relief".I was more than happy to accomodate the... Continue»
Posted by sheilacd 5 years ago  |  Categories: Interracial Sex, Shemales, Taboo  |  
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A wonderful experience


When I was 20 years I was a wonderful thing happened as I remember all my life.

With my best friend Dani and friend, we agreed that we are going to our dull and went around the city a bit. This was a great opportunity for me to be dressed as a woman and such a walk around town for all to see. From what I can remember is I enjoy women's clothes and the role of women. Although I had all the things women I asked a friend if I could borrow her things and be with her disguise, that would not be too suspicious that I'm a transvestite since time immemorial.
Dani and I have come to friend Suzi w... Continue»
Posted by maximatv 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Introducing Jessica (part 2)

You can find part one on my profile if you've not read yet, so let's continue:

As I sat on Johns lap, grinding my ass into his cock while we kissed, I could feel it twitching against me, enjoying itself pressing against my ass. i slid off his lap and onto my knees between his legs. Looking up at his cock with wide eyes. My right hand reached out slowly, as the tips of my fingers touched it, we both sighed with pleasure. My hand wrapping round it instinctively, and immediately began stroking it slowly. John was moaning with pleasure and telling me how good it felt, calling me baby from time ... Continue»
Posted by Want2BeTrans 5 months ago  |  Categories: First Time, Shemales  |  
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Darlene, Jack and I: Part One

I was driving home from a local peep theater when my car broke down luckily I knew a couple from work that lived nearby. I called my road service company who told me they were unable to help me before Monday since it was a three day holiday weekend. Luckily, when I arrived at their home someone was there or I would have been in big trouble having traveled nearly 60 miles to get to the theater in the first place.

Darlene answered the door in a tight black teddy with three inch heels on which of course I thought was odd but she always was a snappy dresser at work. I saw she had a bit of
... Continue»
Posted by NaughtyNshy 4 years ago  |  Categories: Group Sex, Shemales  |  
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My first sex

I left home when I started college and had to take a part-time job delivering advertising leaflets in order to pay my way.

I had been doing the job for a couple of weeks when one houseowner, mowing his front lawn, asked me if I would like to do some Saturday gardening. He named the wage and I readily agreed.

I started that Saturday and after a couple of hours Tom called me into the house where cakes and soft drinks were waiting. He said he had an appointment and he left his wife Terri to keep me company.
Terri was a tall, graceful brunette with 48-inch doubleD breats that looked as if... Continue»
Posted by Dav10 3 years ago  |  Categories: First Time, Group Sex, Shemales  |  
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Learning how to deep throat...

I was working the drive through window at the burger late one Friday night, this somewhat diminutive husky voice placed an order. My cock instantly begin to twitch as I heard the voice. I took the order and instructed the customer to pull up to the first window. As the car approached I observed that the driver was a shemale in full dress with a split up her right thigh to the waist.

I was so absorbed by the sight of that yellow thigh and leg that I fumbled through the rest of the proceeding. The driver looked up at me and whispered 'you'd do better if you looked at my face instead of my... Continue»
Posted by d4david 4 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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