Shemales Porn Stories
Page 15

A Night Out To Remember

A Night Out To Remember
I had known Sue for almost five years but had known Liz for a lot longer. We had met while she was
still at school although I was four years older we still became good friends. After she left school I
helped her with her college work and more importantly when she needed advice about boys and later
girls. I helped her pass through that difficult stage when she was just discovering her sexuality. She
soon became aware that although she liked boys she liked girls a whole lot more.
It was difficult because we lived in a small country town and everyone knew everyone el... Continue»
Posted by pr1456a 3 years ago  |  Categories: Shemales  |  
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A Reluctant CD Meets the Gang

I was at the office and I guess I must have been a little quiet because I scared my coworker, David in the next cubicle to death, almost. Sometimes I take off my shoes and work in my socks and when I stood behind him and cleared my throat, I wasn't sure if he was going to hit me, shout, sit dumbfounded, or be incredulous about it.

He was looking at some rather hardcore porn where a few guys were makin' a girl airtight while she was tied up. I guess I was looking a little too interested myself. This gave him an opportunity to save face about what he was looking at.

"You like?" he said c... Continue»
Posted by LeslieStone 3 years ago  |  Categories: BDSM, Group Sex, Shemales  |  
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Just Like Being Girly For A Man


I've just been thinking how nice it is for a sissy to be able to be in the feminine role with a bf. I'm lucky in that regard in that my bf likes me to be girly and I really like to be girly for him. nothing like being the soft feminine girly boi that I am and being in the passive roll when being made love to. being the receiver and not the giver in the penetration. course sucking his cock is also pretty girly isn't it?

my sissy pussy just loves the feel of a hard cock entering me and the the slow movement as he penetrates me further, then feeling him completely inside me. laying on my bac... Continue»
Posted by sissygirl 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Finally

About a month ago I was away at a course. I noticed a guy across the room named Devin who was well dressed and had very feminine features. I sat with him at lunch because I had a feeling that he was a cross dresser or at least gay. Now I've been bi curious for a long time and have had close encounters, but nothing so far as to satisfy my appetite for cock/cum.
Over lunch we had a lot of discussions about the course and finally led to a conversation about what we do for fun. Devin told me he was a real clubber and liked to club as much as time would allow. At this point I felt a little ... Continue»
Posted by wantingtobiagain 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Art Student

It was the beginning of the semester at the Art Institute and I was pretty excited about my new schedule. Professor Ludovian always brought interesting nude models to his classes, and his tips on how to draw the human body were most useful. I had learned a lot in the intermediate class but now in this advanced class, I knew the professor was going to be more demanding.
Ludovian greeted his students with a grin and a wave of his extremely thin and graceful hands, the hands of a maestro, someone who had mastered the art of drawing the intricacies of the human body. "Hi Daniel, good to see you ... Continue»
Posted by latinCharm 3 years ago  |  Categories: Anal, Mature, Shemales  |  
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A Job In The Theatre

A Job in the Theatre
Chapter 20 -- Gary becomes Gayla
"Be a dear and get that bag from the car," Paula winked.
"Sure," Billy said stuffing his erection back inside his leather pants. He stood, and for just a moment,
was right next to Gary, almost touching. Gary could feel the heat waffling off of Billy. He looked so
obscene with that erection dominating his leather pants. You could see it a mile away. Gary could
never go outside looking like that. Billy could care less.
Billy looked Gary in the eye, had that crooked little smile of his. Gary couldn't believe what he had just
agreed to.... Continue»
Posted by pr1456a 3 years ago  |  Categories: Shemales  |  
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CD And Trucker

CD Adventures Truckers Ch. 02a
Part 2A: Portland to Bakersfield
I turned....
At least four things went through my mind the moment I heard Hank ask me to go along with him.
- One my wife was gone for at least 2 weeks so that was no problem.
- Two, with wireless connection and my laptop I could take my job on the road.
- Three, I had hardly any clothes in my bag that I was carrying. All the clothes in the bag were girl
clothes; my boy clothes were in the back seat of my car.
- Four, my ass (oops, my pussy) was on fire and now stinging a bit from Hank's big cock taking my
virginity just ... Continue»
Posted by pr1456a 3 years ago  |  Categories: Shemales  |  
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Sissy Training Assignment 1: For all Sissies wishi

Sissy Training Assignment 1:

Now the first assignment is pretty simple. Just fill out and answer all the questions below and then send it to me at mastersissytrainer@gmail.com . You do not have to fill out all fields but the more you fill out the better your grade will be. Also fill free to send me a picture of you as well but that is for bonus points and is completely optional. Also I will not be posting personal information, such as real name, address or phone number, unless given permission.

Sissy Personal Information
Sissy Name:
Real Name:
Address:
City:
State:
Zip Code:
Phon... Continue»
Posted by mastersissytrainer 3 years ago  |  Categories: First Time, Hardcore, Shemales  |  
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Sissy Assignment 2 (Novice)

Sissy Assignment 2 (Novice)

This assignment is for new sissies to complete. However, I welcome all sissies to give this task a try and some of the more experience gurls can show some of the newbies how it's done.

Part 1: Sissy Mind Set
To begin I want to make sure you are in a good sissy mind set. You need to be submissive, slutty and ready to serve your master.
So this first part is a daily task I want you to complete. To get your mind into sissy mode I want you to go to the links below and watch these clips beginning to end without touching yourself. You will need t... Continue»
Posted by mastersissytrainer 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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Tranny Night Out

Tranny Night Out and One Kinky Session
Guess I should start by explaining myself, as a young guy I always knew I was not the same as a lot
of my friends and enemies for that matter, girls had no interest in me at all apart from ones who were
long term friends.
I knew something was wrong but never worked out what it was till one evening whilst dating a girl
named Becky I had met on an online dating service who seemed to accept me for who I am.
We had been dating for 3 months or so and I always loved the feel of her stocking clad legs and
seeing her in sexy lingerie, but I secretly was al... Continue»
Posted by pr1456a 3 years ago  |  Categories: Shemales  |  
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Adventures of Lexi Pt 1

The Adventures of Lexi
Chapter 01 - The Transformation
It's not easy being a college freshman. After my eighteenth birthday last week, my parents told me
that they were cutting off my allowance. It didn't take long for me to realize that I needed a job, and
fast.
Since I needed a job with flexible hours, due to my full schedule of classes, my choices were limited.
After responding to several want ads, the only call back I got was from a babysitting company. The
hours were flexible, but were also usually on weekend nights. I guess this was a sacrifice I had to
make.
It didn't take long... Continue»
Posted by pr1456a 3 years ago  |  Categories: Shemales  |  
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First time with a ladyboy at the San Francisco Sou

It  had been a long week at work. So I decided to go to the Sound Factory for a drink and maybe get lucky with the ladies. As soon as I got to the bar, I spotted a beautiful asian lady wearing leggings with pantyhose and a sexy little top. She offered to buy me a drink, who am I to refuse. So we had a few drinks and went to the dance floor. The music was pumping and we started to grind on the dance floor. After awhile she suggested we go back to her place to get a little more familiar with each other. I was tipsy and thought I noticed a small bulge in her pants but dismissed it to the effects ... Continue»
Posted by pog09 3 years ago  |  Categories: Fetish, First Time, Shemales  |  
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me being a pet

As you all know i am a bitch of my mistress "sissychick".
This incident happen recently during my training of being a little slut. So i was sitting right next to my mistress bed, like a loyal dog, still having anal plug inside my ass and my dog collar. It was the mark of me being my mistress slave. My legs were folded right underneath my ass, the floor was cold and i was all naked. My mistress was tired from fucking by 3 of her lovers all day, she was sl**ping still having cum all over her.
Her perfect little face makes me horny, i started to get hard again, it was 4rth time in l... Continue»
Posted by hunknextdoor 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Their First Adult Book Store. Part 5

Albert looks up at Gary with a wicked smile, he takes the hard cock into his mouth about halfway.
Gary moans as Albert’s soft, moist tongue slides along his big dick.
After a minute of slurping on Gary’s cock, Albert says “Your cock is delicious Gary”.
“Thanks buddy.” Gary has heard that many times before, but with this newbie it really means something to him.
Albert sucks the big dick, taking it a bit deeper every few slurps.
In and out, he tries to do it like Gary sucked him and begins gently rubbing Gary’s balls and stroking the cock while it’s out.
Gary tells Albert “You don’t have t... Continue»
Posted by Michelle_Satin 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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The Neighbor...

My next door neighbor had never shown any interest in me before. He was married and straight, as far as I could tell.
One night, however, there was a knock at my door. I looked through the peephole and saw my neighbor standing there. He was tall and stocky, with a beer gut that I found sexy.
I answered, not knowing what to expect.
"Hi. I'm sorry to bother you so late." He said.
"Its ok. Is there something wrong?"
"Look, I don't really know how to do this... so I'm just going to be blunt. I know that your gay. My wife and I have seen several different men coming and going at all... Continue»
Posted by bttmblw 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  
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daydreamin slut

YOUR COCK LOOKS SO SOFT AND SEXY.I GOT HARD THE MOMENT I SEEN IT.I WANT YOU TO GET HARD IN MY MOUTH.THAT WOULD BE SO INDESCRIBABLY HOT.ON MY KNEES YOUR WHOLE SEXY LIMP COCK STUFFED IN MY MOUTH.BOTH HANDS GRIPING YOUR SEXY ASS.BOTH YOUR HAND ON THE BACK OF MY HEAD PRESSING ME INTO YOU. YOUR STARTING TO GET HARD I'M BREATHING HEAVY THREW MY NOSE.THE MORE YOUR BIG SEXY BLACK COCK GETS THE HARDER YOU HOLD ME. MY HANDS ARE SQUEEZING YOUR ASS HARDER AND HARDER.MY EYES START WATERING YOUR COCK IS GETTING BIGGER WITH EVERY BREATH. I STRUGGLE .MY COCK IS POUNDING BETWEEN MY LEGS PRE-CUM IS SPILLING OU... Continue»
Posted by blackcocklove 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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my friend's new roommate and her surprise

So my friend Rebecca and I were planning on going to this bar for the evening but she called me and said she was running a bit late and that I should wait at her place and that her new roommate Shawna should be there to open the door for me. Rather, than wait in my car I went upstairs to her apartment like she suggested. The door was slightly open so I walked in saying hello; to see if anyone was home. I heard some noise in the kitchen so I walked over to check it out. It was Shawna cooking. She was actually a pretty cute girl. She was wearing a white tee shirt that just about covered her ass ... Continue»
Posted by pleasurenfun 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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caught masturbating & crossdressed living at a

This is the first story of a few that I was so lucky to be a part of and I would love to share them with you!

I had hired this woman as a delivery driver because the store I had just taken over had ruined the reputation of the business with terrible service. Her bubbly demeanor, bordering on ditzy was cute and she was herself a beautiful 40 year old woman and a milf for sure! She would be my best tool in the road to rebuilding the business. The customers will love her. She was tall with long slender legs and a real nice round ass, small titties with huge pinky size nipples. Her hair wa... Continue»
Posted by happytayls 3 years ago  |  Categories: Hardcore, Shemales, Taboo  |  
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sissies obey rules


1. A real sissy whore is always ready to be fucked at anytime and anywhere
2. A real sissy whore shows sissy clitty and cunny at every opportunity
3. A real sissy whore begs to be fucked hard
4. A real sissy whore sucks anything that's offered
5. A real sissy whore must be prepared to be fucked in any position
6. A real sissy whore does as told no matter how dirty and low the task
7. A real sissy whore plays with herself as instructed for others amusement
8. A real sissy whore loves being m*****ed in public
9. A real sissy whore moans loudly, especially when allowed to cum
10. A rea... Continue»
Posted by sissyteri 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Visiting shemale goddesses

Sexy hung shemales have long been a favourite of mine and over the years i have had several sexy encounters of all kinds. As ive got older it has become more appealing to have these beauties top me if possible. Most ive met have been quite abrupt and arrogant and have suited the top position well. Not every experience has been nice. However my last one was a really nice suprise.
I was in Amsterdam working for a week and had a 3hr slot early afternoon to amuse myself so took a short walk around the red light area. I am a nicely dressed and reasonably decent looking transvestite so find the she... Continue»
Posted by Jennifertaylor 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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