Shemales Porn Stories
Page 112

Be a Sissy







f***ed to be a Sissy I



The young man stood facing a very large woman sitting in an upholstered
armchair. There was no other way to describe her. She was fat, perhaps,
pushing 300 pounds he thought. The way she was staring at his puny
frame suggested that maybe he was going to be her next meal. She wasn't
saying anything as she visually appraised him for the first time...
Jacob had been brought to this woman by his step-grandmother earlier
that morning. He had been given over to his step-grandmother by the
will of his now deceased parents which made her legal gu... Continue»
Posted by klammer 11 months ago  |  Categories: BDSM, Shemales  |  Views: 2366  |  
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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 2 years ago  |  Categories: Shemales  |  Views: 1029  |  
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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  |  Views: 1692  |  
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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 5 months ago  |  Categories: Anal, Shemales, Taboo  |  Views: 2158  |  
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My Sister's best friend (fiction)

My s****r's friends have always been able to stay with me when things aren't going well with their boyfriends and/or husbands. They've always seen me as a big b*****r. My s****r and her friends were in their twenties and I'm in my mid-thirties. Anyway one night Kristina came to my house with tears in her eyes. I suspected that she and her boyfriend had gotten into a major fight so I invited her in. "Kristina what happened?" "Carlos and I got into a fight because I wasn't home when he got there." "He does know that you're working right." "He does but he wants me to drop everything and be at his... Continue»
Posted by aromanticsoul 1 year ago  |  Categories: Shemales  |  Views: 2657  |  
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Brooke Comes to Visit

Today was a long and stressful day and I just couldn’t wait to get home to unwind. The entire drive home all I kept thinking about was what I am going to dress into when I got home. I guess it was typical thoughts a girl makes like what skirt to wear, with what top and which shoes. I really love the look of short denim skirts. I also love the way they feel on my legs with stockings. Plus, with the mary jane shoes. Maybe add the knee-high white socks. I was getting so overwhelmed with these thoughts running through my head that I started feeling a tightness in my panties.
I quickly went upsta... Continue»
Posted by ahsleymills 1 month ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  Views: 4090  |  
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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 2 months ago  |  Categories: Mature, Shemales, Taboo  |  Views: 2162  |  
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First TS sex

I think I was near my 35Th birthday and, believe it or not I had never had experience with a transsexual. I had plenty adventures with men and liked it very much as well as with women. Decidedly I was completely bi.

As I wrote in previous stories, I’m writing about near 30 years ago. It was not as common as today, no way thinking to come out of the closet.

I was working with a engineering group, developing housing projects and our working hours were far from normal. I was preparing a presentation for our customers and stayed specially long in the office. I came out from the underg... Continue»
Posted by bloodyhugo 4 years ago  |  Categories: Gay Male, Shemales  |  Views: 873  |  
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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  |  Views: 734  |  
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Two hot CD lesbian sluts share an intimate moment

Her name was Kelly, we had met online in one of the gay chat rooms I like to frequent and for the next couple of weeks we had developed a friendship, exchanged pics and fantasies and I was really, really into her. we had a lot in common, more than just the mere fact that we were both gay CD’s with torrid fantasies.

After a few weeks of chatting we had grown comfortable enough with each other that we finally decided to meet in person, I was excited as could be, all I could do was fantasies about what our meeting would be like.

The day finally arrived, it was a warm Saturday in June ... Continue»
Posted by alex_boycd 4 years ago  |  Categories: Shemales  |  Views: 916  |  
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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 10 months ago  |  Categories: First Time, Shemales  |  Views: 4430  |  
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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  |  Views: 2111  |  
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Whore For Two Mexicans

One night I came home from work and saw a old beat up truck from Texas parked in in spot next to my room. As I walk to my room I looked in truck and the back was full of tools and junk, then looking in the cab I could sdee it was a mess with trash everywhere. I thought who ever it belonged to must be slobs. As I got to my room I saw my guess was right as two mexican guys came out of room next to mine and they were a dirty mess. I looked at them and said hi and sort of smiled, they both had sort of nasty grins on there face as they looked at me.

That night I was standing outside having a bee... Continue»
Posted by sissy_gurl 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  Views: 1545  |  
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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  |  Views: 3933  |  
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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  |  Views: 574  |  
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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  |  Views: 615  |  
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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  |  Views: 1040  |  
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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  |  Views: 344  |  
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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  |  Views: 738  |  
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Girly, part two

Laying on the bed after our first time, I grabbed her girly boi clit and squeezed, her breathing ragged and heavy. “So, babygirl … Nicole … you liked being daddy’s girl, didn’t you.” She turned her face toward mine, her makeup now smeared and running, and nodded her head. I caressed her boi clit, “be a good girl and clean daddy’s cock.”

I laid back on the bed as she moved down my body, I could see her wince a little as she got up on her hands and knees. “Keep that ass in the air, babygirl, I like that view.” Her face down, ass in the air with feet held high, still wearing the heels with her... Continue»
Posted by TruckerPerv 1 month ago  |  Categories: First Time, Shemales, Taboo  |  Views: 2110  |  
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