Shemales Porn Stories
Page 119

My Frist time with a tranny

My Frist time it was back when AOL frist came out. I was in a miami chatroom and I met a tranylicous. We Started to chat. I remember going to the profile on the side of the message window and I found out throu pics what a tranny was. I must of been 13 at the time or so. She gave me her address. it was not to far from Downtown so I head over to meet her as I smoked a joint. She had a nice apt, pretty empty She had just moved from Ny. After a little chat we had that helped me relax She came closer to me and we started to Kiss. I felt my bl**d rush threw my body I could feel my ear tingle. She w... Continue»
Posted by lucifer696 3 years ago  |  Categories: First Time, Shemales  |  
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Shemale secretary fucking

Ms Boss had said that I was to see her secretary concerning "letting of some steam". She and I had been at each others throats lately and Ms Boss didn´t like her two slaves to argue.
So we were left alone in the break room after most people had gone home. And we were not to leave until we could get along!
We started aruing about everything, from work stuff to personal tastes to sex. Culminating with both of us claiming to be Ms Boss´s favorite.
The competition was clear. Fuck each other so good the other one yealed.
We nearly tore our clothes of and started kissing and touching each oth... Continue»
Posted by Ankakalle 3 years ago  |  Categories: Shemales  |  
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Daddy's little boy

It was the summer before my senior year in high school and my 18th birthday. My father took me to the strip club down on Main Street. We were enjoying the evening watching all the women dancing when my father turned to me and stated that he was tired. It was one in the morning so I agreed and we started heading home.

Now my father is not that old. My mother and him had me at 16. He was 5'10 and in good shape with short dark brown hair and dark brown eyes. I had never looked at my father as sexy but all my friends would tell me how good looking he was. My mother left my father and I when I w... Continue»
Posted by sparkyking 8 months ago  |  Categories: Anal, Shemales, Taboo  |  
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First time

first time

This is the story of my first careful steps outside as a girl. I was at time 23 years-old, living in a house
with 16 other students and had been trying on girls underwear for some time, but always in private.
This time I would try out somewhere else.
I found an erotic shop in town, which had a cinema in the back. Or actually 3 different cinema rooms,
all playing different videos. I went there dressed in my normal guy�s clothes but underneath I was
wearing my favorite lingerie: a black lacy thong with matching garter belt and bra and a pair of black
stockings. It was my firs... Continue»
Posted by vince01 2 years ago  |  Categories: Gay Male, Shemales  |  
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"Game" Over???

I had not had any Barb time since returning from Kansas City. School was to start up in a week ending summer break and I needed to dress. The folks were at work and I was going to play.

I put on the open bottom girdle dad had bought me, tan nylons, a white lacy bra and my breast froms, and 4" black pumps. I went into the folks bedroom turned on the stereo and sat down at mom's vanity to do my makeup.

I then went to mom's closet and started looking through her closes to see what I could wear. I felt something brush my hard cock and looked down to see a manicured hand gently holding it!! ... Continue»
Posted by Barb51 5 months ago  |  Categories: Mature, Shemales, Taboo  |  
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Gang banged in bondage by shemale co-workers

I had just gotten back home after work when my phone called.
-That´s strange.
When I answered the phone I heard that it was my boss that called.
- Can you come over here please?
She said in a rather seducing tone.
I guessed that I didn´t have much of a choice so I said yes and drove to her house.
Just like the last time her secretary opened and asked me to come in.
-Ms Boss is waiting for you in the living room.
She also said that this might take some time.
Whe I entered the living room I realised that I was gonna get tied upp again. There was bondage stuff al around the room! Dildos,... Continue»
Posted by Ankakalle 3 years ago  |  Categories: Shemales  |  
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Ladyboys: Moving to Thailand and my first Ladyboy


After living in the Netherlands for 33 years I was ready for a big change. I had been toying with
the idea of moving to another country to get away from the stress of it all for a while.
I had girlfriends in the Netherlands. Wives.
I had one nighters and 2 nighters. I wasn't doing bad for myself.
But, there was something missing on the girl side. I love variety. I think I've been with
every kind of girl I COULD be with in the Netherlands. I started thinking about other countries.
Other girls. Other types of girls...
I had seen shemales in Amsterdam. Emphasis on the boy part. And they ... Continue»
Posted by casinocock 1 year ago  |  Categories: First Time, Shemales  |  
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Cow Girl`s got something hard in her jeans

Last Friday night me and the guys from work stopped to have a couple of beers. which of course turned out to be a whole lot more. boy was i going to be in trouble when i got home. but when i got home it was all quite, too quite. then i saw the note. "You son of a bitch you knew we had that dinner at my mother`s!" i knew i was in big trouble now. being a little d***k i thought hell with it i am going to have a good time any ways. so i put on my boots and grabbed my cowboy hat and headed to the bar to do a little country dancing. as i looked around i noticed a nasty looking blond on the other ... Continue»
Posted by manard 2 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Dirty TS Supprise

True Story I'd been out drinking with a few mates first the pub then we hit the clubs. It was late and I had work then next day so left my mates and went to get a taxi home. walking up the street for a taxi I noticed a woman standing on the corner. The girl was facing away from me but looked hot from behind short skirt, fishnet stockings and high heels looked like a total slut my kinda girl. As I passed by she asked if I had the time of course I stopped and used the oppertunity to chat her up. She was stunning long dark hair brown eyes and tanned skinned after chatting for a few minutes she as... Continue»
Posted by crbigboy 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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What If My Mom

Country Boys with a Difference

I loved my b*****r's cock, don't get me wrong, it's just what happened and our Mother loves our cocks as well as she loves our breasts. Let me explain.

It all happened when I was 13 and my b*****r was 11. Ours was a happy f****y living in the hill country of Kentucky, way back in the hills, but we were not 'hill - billy's'. Dad had a good job with General Electric, a aircraft designer and Mom was a teacher at the local high school. I don't know why we got sick but we did.
Bobby and me, boy did we get sick.

Dad and Mom were real worried I got told later... Continue»
Posted by chchboy 4 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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The Bondage Whore, Chapter 9

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.



Chapter 9 - First Anniversary on the Job

It was July 15th, a quieter than usual Wednesday night, and Rachel was daydreaming. As tonight was her first anniversary as a bondage whore, Rachel was in a reflective, and somber mood. She thought back on the year just past, the many indignities, and was trying to sort out how exactly she wound up like this, and what was worst about it.

She remembered back to that fateful night when she happened across the "Bondage Whore" want-ad in the window of Jimmy's whorehouse, and how nai... Continue»
Posted by thongcutoffs 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Use me

OK, I've had this fantasy for a while and I still haven't lived it out yet :( ...

I'm on my back, tied to the headboard by my wrists - my legs are tied so they're up in the air. My arsehole is exposed and I have a ring gag in my mouth.

I can just about reach through the gag with my tongue so you mount me and rub your pussy into my face. Occasionally you switch directions, smothering me, really pushing back into my mouth and nose - I can smell your holes and I clean your arsehole out before you switch back.

Once I've flicked your clit for a while and lapped up your juices, you've come.... Continue»
Posted by tay1 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Sissy Captions Transcribed

Pet had a new assignment last night. Certainly video reinf***ement of her slutty sissy desires was on the agenda. But this time, she used multiple neural pathways for her reinf***ement.

http://xhamster.com/movies/2078893/sissy_boi_gif_training_3_sexy_time_by_dressmeuptoplay.html

A very nice hypnotic trainer, with lots of flashers and captions. But... i wonder? What do ALL those captions really say?

Thanks to pet... we now know.

===========================================

DressMeUpToPlay
Presents
“Sissy gif Training 3, Sexy Time”

Put on a nice outfit and find the nearest coc... Continue»
Posted by dwadd73 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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My Wife My Mommie part4 con

About two block from the house Ann stated "Tom's Home". It was
then that Tami noticed the pacifier around his neck and in his
mouth. He took it out immediately and saw the two girls in the car
next to them at the stop light smiling.

Since it was a warm day, Ann had the car windows open. Tami
looked at the girls, and now being himself, stated "I'm trying to
quit smoking."

"Sure you are," the driver of the other car said, as the light
turned green and she drove off laughing.

"Please Ann, don't do this to me. I'm sorry, I really am,"Tami
said.

"Now you know ... Continue»
Posted by alexwd0 4 years ago  |  Categories: Fetish, Shemales  |  
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TV/CD adventures - going for ice, remember ID

It's amazing what high heels, wig, makeup, nylons, mini, etc can do for ya when going out in public.

Couple months ago I got me a room at Imperial Palace on the strip and I think the front desk caught on I was using the room for casual sex. I put up an ad on craigslist and gave out the room number. But setting up times and availability was difficult because I didn't have a computer in the room. So the front desk constantly was connecting me to "different" guys. After being drilled deep by 2 guys I decided to go for ice in my fishnet no panties slut outfit. My ass was gaped and sloppy... Continue»
Posted by vegasjful 2 years ago  |  Categories: Shemales  |  
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preparing for date fuck

When ever I had a date with a guy,who would end up fucking me.First I would take along hot bath,shaving my legs,arms,chest,and face.squirt some babyoil into the water,making my skin real soft.then I would use my fem wash bottle,and clean myself out realy good.I would then pull out my dildo's,and would fuck myself until my ass was ready for a real cock.then i'd get out,and dry off,put on my makeup,then go into the bedroom,I would pick out what to wear,which ment to wear a mini skirt,short of course.I love wearing short revieling skirts,low cut shorts.I would also put on a matching bra,and panti... Continue»
Posted by blonde68 2 years ago  |  Categories: Shemales  |  
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my cd experience part 2

Then i feel my ass hole being f***ed open as you slowly entered me it was slow but you did not stop till all 10 inch was buried in my ass, ive never felt anything like this as you stay still and let me adjust to your length! My legs are shaking i cant stop them pure xstacey is what i feel! I pluck up courage to start rolling my hips which made your cock touch places ive never had touched before aaah aaah aaah mmmh i couldnt control my groaning, then you withdrew just to the rim of your helmet and then BANG BANG BANG BANG BANG BANG you pile drove your dick into me like a cars piston! I fucking ... Continue»
Posted by andytmpson 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Milking Time B2 Chapter 3 Ebony & Jordan Part

Chapter 3: Ebony & Jordan Part 2

"Okay," said Ebony. "See that pile of mats over there? Get on top, and stretch out on your back. I'm gonna feed that little blonde pussy of yours its first dose of real cock that it's ever had on the Island."
Jordan moved over to a large pile of floor mats that Ebony indicated, and climbed on top as she instructed. Now Jordan was lying in a horizontal position, but she was elevated several feet off the floor.
"That's perfect girl," said Ebony, as she lined up her massive cockhead with Jordan's pussy. "Any last words?"
"I'm going to shove this blac... Continue»
Posted by gregster 2 years ago  |  Categories: Hardcore, Lesbian Sex, Shemales  |  
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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  |  
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Caught wearing my mother's stockings

For as long as I can remember I've been obsessed with my mother's legs. My very first wank was brought on by the sight of her curvaceous stockinged legs in high heels. She also liked to wear knee high black leather boots which would send me into a frenzy. I once saw walked past her room while she was getting ready for bed and saw through the gap in the door that she was wearing those boots and nothing else! Needless to say my dad fucked her senseless that night and I listened with my ear to the wall, wishing it was my cock for fucking her beautiful curvaceous body.

I longed to kiss her stoc... Continue»
Posted by petearch 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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