Shemales Porn Stories
Page 16

Dude Looks Like a Lady

Last night I was at a bar for a few drinks with the guys after hockey. We were joking, drinking and playing some pool. On the table next to us was a beautiful woman in her late 20's playing against her boyfriend. She had huge boobs that were spilling out of her tight tank top. I was having a very hard time concentrating on my game because every time she bend over to take her shot I got a huge glimpse of her wonderful rack. Her Boyfriend noticed I was staring and didn't look to pleased. He was also twice the size of me. After I finished my beer I told the guys I was tired and left. As... Continue»
Posted by niagaraguy72 5 months ago  |  Categories: Anal, Shemales, Taboo  |  
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My wife introduces me to submission and cuckoldry.

It took me a while to come clean to my wife about my time before we met. In that time i had been a submissive to a Professional Mistress in the Midlands and it was from her that i developed an interest in both servitude and crossdressing. Mistress/Madam had always insisted that i should be dressed as a woman whenever i was in her presence. After Mistress/Madam and i had gone our separate ways after many years of being together i had to admit to feeling a little alone and deserted and with no direction in my life. i had several relationships and none of them had any idea about what i had been ... Continue»
Posted by oldognewtrix 5 months ago  |  Categories: BDSM, Mature, Shemales  |  
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I Knew I Was A Sissy (Part III)

The following months were pretty stressful. I was afraid that Nick may talk to somebody about me and then my secret would be exposed. At the same time I had to find a way to avoid hanging with those guys without raising any suspicions. I managed that by focusing on my classes and taking several extra ones. Nick didn’t talk so I calmed down. After Christmas I was relieved when my parents told us that we had to move in another neighborhood, that meant new school, new friends and, most importantly, long distance from the old ones.
I kept dressing at every chance; that means each one of the few ... Continue»
Posted by georgette32hk 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Making of

THE MAKING OF JANE

Jason H. was a small boy who had suffered from heart problems as a
c***d and had not been permitted to play the "rough games" other boys
his age played. At age 11 he was finally given a clean bill of health
and allowed to be a normal boy, but he was shunned by the other boys
because he didn't know how to play football or baseball or basketball
or any other active sports. Whenever, the other boys had to pick
teams, Jason was always the last one picked due to his lack of skill
and small size. This hurt him greatly, and he always avoided being
put in the position... Continue»
Posted by klammer 5 months ago  |  Categories: Gay Male, Shemales  |  
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14 Days to Gay - a sissy Training Guide

i wrote this as a guide for sissies to finally shed the inhibitions and go gay - for real - like they know they should. Be a gay little sissy like you were meant to be.......

14 Days to Gay
1. Wear panties all day. Listen to Permanent Princess as you fall asl**p.

2. Wear a thong all day. Watch Bimbo Blessing before bed. Listen to Permanent Princess as you fall asl**p.

3. Wear a thong all day. Use lip gloss throughout the day. Buy a women’s magazine (like Cosmopolitan) from the local grocer. Watch Bimbo Blessing before bed. Listen to Permanent Princess as you fall asl**p.

4.... Continue»
Posted by jamie_anne 5 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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how i got my start as a sissy

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Growing up was tough . I spent a lot of my younger years trying to figure out if I was normal or not . Had many girl friends but still I had an attraction to cock . This all started at a very early age and abuse continued till upper ages from both sexes . I really started exploring my sexuality after I joined the army and got away from home . There I was used by other army high ranking men who knew what they were looking for . I had a command sgt. major for my first dom who took me out one night , Made me dress for him and then proceeded to **** me . I found that this turned me on deeply ... Continue»
Posted by klammer 5 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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hook up with transsexual.


Another great tape and another great yank of the crank. Yea, she-males were pretty hot, Tom thought as he hit the eject bottom on the tape deck, but where on earth would he really find one? He had little doubt that if he did find a place where they hung out that there would be more than a few with a serious case of ugly. The chances of finding one like the ones in the video taped he had just been watching was pretty slim. But, he knew if he never went looking, he would never find one. He knew they preferred to be called transsexuals and not she-males as they regarded she-male as a rather der... Continue»
Posted by klammer 5 months ago  |  Categories: Fetish, Shemales  |  
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Equalized




It was hard not to let the client see the nausea inducing fear that I
felt at that moment as the courier interrupted our meeting to handed me
the small pink envelope. I didn't even need to open it right away, I
just tucked it into my desk drawer and tried to keep my focus on the
details of Mr. Robinson's proposed business loan.

I told him we would need to review his proposition in order to get the
loan approved and would get in touch with him soon, but in reality I
just wanted to get him out of my office as quickly as I could. As soon
as the door closed I was at my desk pulli... Continue»
Posted by klammer 5 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Behaviour Modification and Sissy Trainin


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 movements with graceful and fluid actions


... Continue»
Posted by klammer 5 months ago  |  Categories: Fetish, Shemales  |  
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Dressed



I could never pass as a woman. I am clearly a sissy put into woman’s close. Love being sent out like that. Exposed. Knowing whoever sees me knows just what I am. I have only done that at adult bookstores and at adult theaters. When openly dressed there, either in nothing but lingerie and stockings and panties, or if I go in a skirt, stockings, blouse, bra and breast forms, it is not only clear what I am, but most men who enjoy sissies see it as an open invitation to use me. When dressed like that men will walk up and reach under my skirt or into my panties to grope and fondle me, o... Continue»
Posted by klammer 5 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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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 5 months 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 5 months 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 5 months 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 5 months 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 5 months 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 5 months ago  |  Categories: First Time, Shemales, Voyeur  |  
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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 5 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
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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 5 months 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 5 months 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 5 months ago  |  Categories: First Time, Shemales, Taboo  |  
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