Shemales Porn Stories
Page 59

From a shy virgin college boy, to makeup and heels

So I'd been away at college for about a month, didn't have many friends, or any confidence to speak of. Not long after starting classes I started dating this older girl, she was cute, but a real bitch, she wouldn't fuck me, she'd treat me terrible, and make me wear her panties while I ate her pussy, and after she came, she would watch me cum on my stomach, and then run her fingers through it, and stuff them in my mouth. While this would turn me on to a point, I knew this girl had to go, after a few weeks I finally managed to get away from this abusive girl.

So a little time goes by after th... Continue»
Posted by smonkeys32 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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CL Meeting

BABY MOMMA GONE…NEED ME A FAGGIT

That’s what the title read.

It caught Jeremiah Hall’s attention. He clicked to open it.

The content read, ‘Looking for a faggit bitch to use tonite. Gonna use you as my cumdump, etc. I’m a thug that need a sissy ASAP. Hit me up. Five 55. Let’s fuck. 2 zero zero. Very soon slut. 56 want it now. Hosting at a motel. Seven. Call only. 5’

The ad on Craigslist intrigued Jeremiah. So he punched the number in his cell phone and hoped the posting person would answer.

“Hello,” said a deep voice.
“Hi. I saw your ad on C-L. I’d like to be your bitch boi t... Continue»
Posted by faggyboi 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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a very special girl

"Slam!"

Everyone in the hallway jumped slightly, turned and quickly looked at
the tall girl near the sound of the slamming locker. Satisfied that
there was no crisis at hand, the k**s at the school mostly went about
their business. Of course, there were the few admirers that glanced at
the girl at the locker, but it was no major deal.

After all, Marilyn Walker was used to being looked at. After all, how
many 6'3" girls wear 4 inch platform heels? How many 6'3" girls are
there? Oh well.

She swung her backpack over her shoulder, and strode slowly along the
bustling hallways ... Continue»
Posted by pcarter 1 year ago  |  Categories: Interracial Sex, Shemales, Taboo  |  
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Sissify Yourself



Behaviour Modification and Sissy Training

1. Think about why you want to become a girly girl before you do it.

Having the clear goal of looking great and being happy because of it, will add to your self esteem. Which in turn will increase your attractiveness through radiating self assurance. If you just go through the motions, it will show.
"any "female" can present herself in a feminine and alluring way with patience and practice, but before you can captivate and entrance even an audience of one, you must learn to move with effortless beauty."

2. Substitute clumsiness and jerky ... Continue»
Posted by klammer 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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Sissy Story




(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences for writing this story were things like those fantasies, straight interracial gangbang porn flicks, a strong fetish for female cigarette smoking, strip clubs, hard rap/rock music, an overactive imagination and a weird, corny sense of humor. If you're easily offended by "low-class grammar", si... Continue»
Posted by klammer 1 year ago  |  Categories: BDSM, Gay Male, Shemales  |  
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Trip to the Bathroom




Strong hands pulled mine behind me, and I felt and heard the unmistakable sensations of a nylon tie-wrap locking my wrists securely behind me. A deep brown voice whispered into my ear, "Well, well, well, what do we have here? Looks like I got myself a little piece of white meat to play with".

A very large black hand clasped tightly over my mouth prevented me from responding, protesting, or finding out what the fuck was going on, the voice continued: "I tell you what Whitey, we're going to try a little experiment. I'm going to outline what your future could hold, and if your rea... Continue»
Posted by klammer 1 year ago  |  Categories: BDSM, Gay Male, Shemales  |  
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The MILF next door [parte uno] (Karen)

This a story, fictional, nothing more!

I have lived in the the out skirts of this big city for quite some time now. I do have a great relationship with most of my neighbors and the community in general.

Across the street is the old grumpy George, he sits in his porch and drinks his coffee every morning looking at people gone by, always complaining about something. Next to him are the Rogers, nice f****y, and on the other side are the Smiths, and on my right side are the Ortegas, nice Mexican f****y, on to my left were the Chavez, now only one member of the f****y left in the house duri... Continue»
Posted by ilialenyc 1 year ago  |  Categories: First Time, Shemales, Voyeur  |  
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Wrong Time for a Trip to the Bathroom




Strong hands pulled mine behind me, and I felt and heard the unmistakable sensations of a nylon tie-wrap locking my wrists securely behind me. A deep brown voice whispered into my ear, "Well, well, well, what do we have here? Looks like I got myself a little piece of white meat to play with".

A very large black hand clasped tightly over my mouth prevented me from responding, protesting, or finding out what the fuck was going on, the voice continued: "I tell you what Whitey, we're going to try a little experiment. I'm going to outline what your future could hold, and if your reaction i... Continue»
Posted by klammer 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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White sissy used by black Masters

White sissy used by black Masters


I’m booked into a London hotel and, after you text me to say you’ve arrived, I text you back the room number. It seems like ages before I hear someone attempting to open the door, followed by a firm knock and I jump up, excited but nervous about what’s about to happen. I walk over and unlock the door, careful not to meet your eyes as the door opens. I'm dressed in male clothes but I perform a very feminine curtesy as instructed, feeling both self-conscious and humiliated as I do so.

I see your dark presence enter the room out of my peripheral vision a... Continue»
Posted by NancyBerlin 1 year ago  |  Categories: BDSM, Interracial Sex, Shemales  |  
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A Very Special Lone Star

A Very Special Lone Star

My name if Jennifer and I hail from Texas – the Lone Star State. I became the woman I was meant to be so long ago, it is almost impossible for me to remember ever being that “other self.” It took a while to figure it all out of course. Most gurls know the story – discovering dad’s girly magazines, the fascination, the urge not just to look at, but to look like those beautiful women. The first foray into mom’s or s****r’s closet. The breathless thrill of slipping into your first pantyhose or bra, the first touch of lipstick, the first pair of heels, most of all... Continue»
Posted by jenn1 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
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New Rapper & Femme Bottom

Lachelle Green hung up the phone with the video producer and checked her youngest two c***dren’s math homework. The woman in her early 30s was not only a single mom & homeschool teacher, but she was also the manager for her oldest son’s increasingly successful rap career and a powerhouse negotiator. She had her first when she was s*******n. While most would have written her off, she went about arranging for daycare provided by her grandmother and graduating as her high school class’s salutatorian. From there, she had a full ride scholarship to Cal State – Fresno and obtained a degree in busine... Continue»
Posted by faggyboi 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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Mature Extreme Tranny Prostitute Part 2

"Yes, but I'm not messing about. If you would like to come then follow me now. I will explain what will happen when we get outside. "
The folder was quickly passed around the five of them, each of them looking at each other- silently asking - should we or shouldn't we?
Dave stood by his car knowing that at least some of them would come.
Eventually, one by one they emerged and started to walk over to Daves car.
I moved the sofa into the centre of the room. It was now facing directly away from the entrance door to my front room. Just as Dave had requested. Everything was in position, I j... Continue»
Posted by SexyTinaTV 1 year ago  |  Categories: Anal, Shemales, Taboo  |  
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My beginning

I have been a closet cross dresser since my early teens seeking my mother's panty hose and underwear I thought I had kept it well hidden when I turned twenty I got a place of my own I found it very hard to get my women's clothing since I didn't have the courage to go out in public which brings me to my story . a friend of moms named Sherri was bag ng problems with her old man and they had spot up she came to me and asked if she could move in and help with the rent I was all for it Sherri wes a tall red head very pretty and we'll built a couple of weeks went by she was gone one evening a pair o... Continue»
Posted by mike63bear 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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Tranny Surprise Part 2

Things were off to a good start with Dani. We have been texting each other throughout the week just talking and setting up another date. We decided to go to the local fair I picked her up around 530 and she wasnt quite ready yet so she let me in hugged me and went back to finish her hair. I sat on the couch and played with her cats for a minute, she was back in no time and she looked great!
Tranny Surprise Part 2
"Wow Dani you look really pretty in that sun dress." I said. "Thank you" she replied with a big smile.
We got to the fair and we went in we w... Continue»
Posted by Entities 1 year ago  |  Categories: Shemales  |  
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My first time. Please excuse the grammar.

The phone rang out it's message tone, shrill but welcoming at the same time. I picked it up and looked at it. It was from him. I thought about ignoring it, my nerves getting the better of me at last, as I was a nervous wreck about this whole adventure.
Several weeks ago I had met a man who suggested that I should sell my body for much needed cash. I laughed at first but the seed of the thought grew with every passing day. Should I do it? Well, I put an advert in a website specializing in e****ts from all walks of life. Shit! What was I thinking? My advert wasn't very good and I hoped nothing... Continue»
Posted by ambu99977 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Confessions of a tgirl slut


When the day started, I had no dates, no arrangements of any kind. But I was feeling horny. I needed cock. I'd gone over a week without sex and I am one cock hungry sissy slut. I'm getting on a bit but I know how to dress and do my makeup. I like to think I can embody a straight guy's fantasies and give him the sex his wife won't and dress in a way genetic women generally can't be bothered to do. So I never wear tights - always seamed stockings, generally with a Cuban heel. I'm also crazy about garter belts with multiple straps, the more, the better. Heels - no less than six inches. A corset... Continue»
Posted by NancyBerlin 1 year ago  |  Categories: BDSM, Mature, Shemales  |  
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1994 New Year's (Keela)









This a story, and no more than that!

I could not go home for the winter break due to tons of things to do about my college thesis, so I stayed in my adopted town in the Pacific North west, so Keela my running teammate. She had the same problem, she was writing her thesis as well.

Christmas went by and I spent it in my apartment by myself and tons of papers everywhere, I had chinesse take out.

New Year's eve came along and I decided to call my friend to see what she was planing to do. It was a lot of snow on the ground and I really did not want to go downtown to cele... Continue»
Posted by ilialenyc 1 year ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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Cockatoo Part 3

Maybe things could have been different, I don’t know, but I found myself
in a taxi on the way to Samui airport. I was struggling to come to terms
with what had happened and I felt physically sick at what I had heard. I
had to get the taxi driver to stop so I could retch at the side of the
road.


I managed to buy a ticket on the next flight to Bangkok and by mid
afternoon I was back in the city. I booked into a hotel close to Nana
Plaza and sent a couple of hours stewing in my room, drinking the gut
rot scotch from the mini bar. I was raging at Alex, at Kritsada and
above all at me ... Continue»
Posted by nikkiesilk 1 year ago  |  Categories: Lesbian Sex, Shemales  |  
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He doesn't fuck me like you do.

"I'm so fucking horny right now. I can't bear it..."

Those are the kind of texts I get from you throughout the week. Every now and then just to remind me what you are looking forward to. What we are both looking forward to. Thursday nights can never come soon enough, it's a shame I can only get away that one night a week. It's fine though, the anticipation and all the secrecy only makes the experience that much more satisfying when we are in the moment. We tease ourselves, it's almost like torture, until we finally get our moment.

I walk in trying to contain my eagerness and excitement ... Continue»
Posted by virg0man 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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New year eve

First of all I need to put you in situation, you could see my profile but summarizing I'm a 28 old guy who crossdressed but stopped it because i felt ugly and manly, then i consider myself between gay and a woman and i have desires over men with me as a man but mostly as a woman. many months ago I met a guy chatting online in IRC's who's much older (he 65 me 28) and he gave me confidence enough to start a relationship with him, he has changed my whole world and we started dating 2 months ago but me as a guy, and for new years eve i planned a date for me as a woman. that's it.

Well, here i a... Continue»
Posted by Lindsey_cd 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  
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