Shemales Porn Stories
Page 5

Submissive

Now I have a very feminine side and have always been interested in men,
however, being married and from a small mid western town where they called
guys interested in men queer, fags, well you know all the derogatory terms
the straight laced populace use. We had moved to Florida for the purpose
of a job that I had applied for and after two interviews actually landed.
I found that even though the city we had moved to was more of a large town,
the community didn't come down so hard on guys like me. I have always
ignored my interest in men, but over the years have been approached by men,
... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  
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In Püblic



I began my
transformation from regular boy into cock suckking teenage crossdresser.

we were having a really hot heat wave here in philadelphia; my mom wanted
me to get out of the house and off the computer so she suggested a movie.
I felt wierd going to the movies by myself but I really did want to see
that inception movie. I looked up when they the theater opens up and was
surprised they had a 1030am showing and it was a cheaper price which was
good for me. Being on summer break from school and not having much luck
finding a part time job I was short on money. I did not want ... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Nervous

I have never been so nervous in my entire life, what the hell was I
thinking?!

Before I start there, let me take you back a bit and describe myself. My
name's Sal and I'm kind of a huge pervert. I've got short black hair and
I'm 19 years old, 5'7" and 150lbs. I'm pretty small all in all, but because
I cycle a lot I've got nice thick legs and a bit of a bubble butt.

Back to me being a pervert. I'd never been with anyone before, so I was a
total virgin. I'd recently been getting my rocks off online looking at
crossdressing and bondage pics. I'd recently started buying linergie, sex
... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Mandy



Sissy Mandy


I haven't left the flat in months. But then, why should I need to? Master
John provides all I need, as long as I'm obedient and do as I'm told with a
smile. And, I do.

For instance, I've been told to entertain his friend this afternoon and
it's Alex, the big man who does martial art. He's got blue-eyes, blonde
hair and a pony-tail, a bit like the one I wear sometimes. And, he's got
muscles, biceps and chest muscles, so he fills his tee-shirts ever-so
well. Oh, he looks good? and, I felt giddy as he took me in his arms and
lifted me off my feet quite literally, ju... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Early Morning Encounter With Transwoman

Was walking back from town early in the morning, was stranded in the outskirts of the city which is distant from my own home in one of the suburbs. I had left the warmth of the house of my friend in the city, and ventured out into the early morning, 1:00 or 2:00 o clock, it was cold, but not as cold as it could have been, the clouds in the sky made sure of that, and for that i was happy, despite the occasional light to medium downpour.

I had been texting a Lady friend, a woman, asking her to let me in and stay and in exchange i would eat her pussy, she agreed and was horny however she was ... Continue»
Posted by trueblue934 1 month ago  |  Categories: First Time, Masturbation, Shemales  |  
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A surprise at the party - Part 2

In part one of this story I've told the tale of how I met Tanya. A party at my friend's house, in which we were introduced with no pretext. A few drinks and a slow dance later, We were running up to find a bedroom, like a high school couple in a college party. An hour more went by and we were standing together in the shower after an unusual, yet very pleasurable sexual encounter. She was tall, beautiful, and had soft East-European facial features I just couldn't resist.

As we were standing in that small shower cabin, and I was washing off the soap off of me, she leaned in to kiss my back, w... Continue»
Posted by GalFa 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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The odd meeting!

Once home from work, I made a cup of tea, sorted out a piece of cake and sat in front of the computer and logged on. xHamster first. Three new messages and a new friend request. The messages were easily sorted and so I checked the friend request. I liked the sound of the guy. He didn't have many pictures but I liked the ones that he had posted. Also he had left a lovely comment on my latest gallery and so I thought that I wouldn't be churlish and accepted him. Almost as soon as the messages went I saw that I had another message. He thanked me for accepting and said that he liked my profile and... Continue»
Posted by dasilva1672 1 month ago  |  Categories: Gay Male, Shemales  |  
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Cockatoo Part 8

Cockatoo Part 8

Shane's lips brushed mine so gently I wasn't sure he had kissed me at
all, as if he was still giving me the chance to back out. I closed my
eyes and pressed my lips onto his and I felt the pressure increase and
we were kissing properly, his lips crushing mine. I felt lightheaded,
and the bl**d began to pound in my ears as I felt his arm pull me
closer. I hesitantly put my hand up to his face to stroke his cheek, and
I was shocked to feel his stubble beneath my fingers. It was enough to
jerk me into the reality what I was doing and I froze. What the hell was
I doing? ... Continue»
Posted by nikkiesilk 1 month ago  |  Categories: Gay Male, Shemales  |  
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Love Dress

As Bruce steps up softly behind me, he slides his hand around my side and caresses my belly as he pulls me back into him. As his other hand grabs my left side, his right one slides down the my bare leg where the slit runs almost to my waist, and he begins to pet my smooth leg under the leather. I catch my breath, then lose it again immediately as I feel his whiskers poke my bare right shoulder at the base of my neck, and he sweetly bites and kisses me there. I take a long drag off of my cigarette, inhaling deeply as my free left hand reaches back to find his stiffening bulge through his sexy... Continue»
Posted by SexyLeatheress 1 month ago  |  Categories: Anal, Fetish, Shemales  |  
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A kitty in a movie hall Part -3

There I was, stuck in a movie hall naked after being fucked and cummed on again and again for hours. I realized it was evening and now there might be more people coming in. It was safer to get home somehow. But how? With no clothes and no one to turn to, I stood there shocked with a cum coved body, leaky cock and puffed red asshole full of sticky cum.
"What are you standing for boy? Cocksuckers belong on their knees!" I heard the man, suddenly beside me. I jumped at his voice because I never heard him coming but without a second thought I dropped to my knees facing his crotch and I knew that ... Continue»
Posted by CumLovingKitty 1 month ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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My shemale neighbor part 1

hello guys and gals this is a fantasy I had when I was in high school hope ya'll enjoy.

"Good Morning class today we have a new student" our teacher said. "Hey my name is Sabrina and I'm from California" said the new k**. She then took a seat next to me. She looked at me a said "Do you live in Hollow Creek". "Yeah I do" I answered. "Cool can you show me what bus to get on after school" she asked. "yeah no problem" I responded. Sabrina was a cute girl stand at 5 feet 8inches she had a butterfly tattoo on the left side of her neck, her boobs were c cups, and she had a cute bubble butt.

Af... Continue»
Posted by kingdick97 1 month ago  |  Categories: Shemales  |  
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Amy's Return

The phone screen displayed Amy's name, I had not spoken with her in months, my curiosity piqued I took the call but let her speak first.
"Hello Daddy" her voice low and sultry the way I taught her.
"Hello Amy, I see that hunky basketball player dumped you."
"Uh, what, how did you....huh?"
Ah the youth, so predictable. But I suppose I was no smarter when I was her age, looking back on those times, yes, I was just as dumb. "Because I know you my dear, remember I was the one that taught you. You were always my favorite." Trans girls like real girls love compliments and she was one of the s... Continue»
Posted by gypsy61 1 month ago  |  Categories: Fetish, Shemales  |  
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slut

Hotel Slut:
I take you to the hotel for some fun. So I decide to tie you down to the bed like a dirty sissy slut like you should be. I strip you naked and tie you down on your back with your head over the edge of the bed. This leaves your mouth open so you can be face fucked and the big cocks that will be coming can slide down your throat. I leave you there and go down to bar, but I leave the shades open so anyone passing by can see what a sissy slut you are.

I go to the bar and run across a group of men in town for a convention. Knowing that conventioneers are always horny and looking for... Continue»
Posted by bmld55 1 month ago  |  Categories: Shemales  |  
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Being trapped, a rewarding experience

It was many years ago, I was a newly minted Sargeant in the Army and was on a 48 hour pass in Bangkok. I was celebrating being promoted and had a few bucks in my pocket and a massive hard on. I went down to pig alley and went to several bars where the local girls were doing their version of Go Go dancing. Most were without tops and their small breasts with erect nipples were glistening with sweat in the tropical heat. My cock was certainly not softening in that atmosphere. A fairly tall girl approached me. I am a nipple fan and her's were extended a full inch above her small but firm bre... Continue»
Posted by phillymark1 1 month ago  |  Categories: First Time, Shemales  |  
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how did i lost my virginity

The storie start like that i was always goving to a secret place during day off and week ends for crossdressing and taking sunbathing
For many years i always go to this place and i never so anyone there !

But this time when i entered the forest i forgot to look behind me and this was my mistake and i will pay the price for that mistake !

So i walk true my secret place but a guy was following me but i didont see is
As usual i arrived t8 my place so i open my bag put a blanked on the floor and sited down and started to dress slutty and makeup sexy !
I was ready for my sunbathing so ... Continue»
Posted by sissyslave78 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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First Night Out as a Sissy

It was the first time I dared to act on my fantasies but the timing was most certainly perfect! Feeling the urge to explore my sissy side out in the world, I decided I’d hit the local sports bar in hopes I’d find a man that I could make want what I had to give.

After taking my time doing all the preparation for a confidant night, I put on my favorite panties and my tightest jeans (the ones I would never dare to wear outside until this night). I was getting so excited with anticipation of making my fantasies come true that I could feel I was having a hard time breathing. As I looked at my p... Continue»
Posted by Crystal_ed 1 month ago  |  Categories: Gay Male, Shemales  |  
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Beautiful yet Ugly

Was feeling a need to fuck a tight pussy one day when I noticed a profile on a guys dating site. A CD with a sleek, rounded ass on top of some very nicely shaped legs. A cute outfit said he cared enough to try, so I flirted and got an invitation to join him. I left work in a hurry and headed to his playpen, he had an RV which was set aside for playtime. I got there, horny as hell. As I approached him, the butt-ugliest face I have ever seen looked out with a scared, almost haunted look. I nearly turned away, but remembered that ass. So, I grilled and went on in.

Ok, his face was ugly, pock ... Continue»
Posted by Aden46lb 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  
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What a sissy wants from her Daddy

Many people ask me, Why are you a sissy? What do you get out of it?

Well I will explain.

I'm male and when I'm in normal clothes and at work, I look like a normal guy. I like girls and am straight.

BUT

I have another side!

Becky my sissy side!

Such a lovely little girl, cute, loving and submissive. Becky loves her Daddy or Mummy. She likes kisses and cuddles and loves being hugged.
Becky loves pink satin panties with white lace frill. Ivory sheer tights and stockings, pretty knee socks or frilly ankle socks and patent black Mary Jane shoes! Satin Dresses, Japanese Sailo... Continue»
Posted by igglepiggle 1 month ago  |  Categories: Fetish, Shemales, Taboo  |  
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A surprise at the party - Part 1

I was sitting at my desk, writing, when Ronnie called. She asked me if I was coming to her party and I said no, again. She persisted, saying quite a few of my friends would be there, and tried to convince me to come. I said I would gladly do it some other time, but mentioned I was just barely going to make my deadline. She said she had a surprise for me, but it was not something that could change my mind. So I refused again and hung up. Ronnie was a great reason to attend the party in her own right, divorced and very sexually open, but I had made the choice to focus on work.

It was a good e... Continue»
Posted by GalFa 1 month ago  |  Categories: Anal, First Time, Shemales  |  
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"I'm being brainwashed into becoming a s

This story is a true story and it's about me. My name is Gene Burnett and I'm a sissy, my gurl name is Jennifer. I give you my real name; "Gene Burnett", without being worried that I will be exposed. I'm not really worried because I've already been exposed on Tumblr. I will tell you what lead to my exposure now. I've always been bisexual and favored women over men when it came to sex. For a good part of my life I kept my bisexuality bottled up. I had only had a couple of sexual encounters with men up until 18 months ago. I have also always been submissive, with every girlfriend that I ever had... Continue»
Posted by JennyJean 1 month ago  |  Categories: Shemales  |  
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