Shemales Porn Stories
Page 75

A sissy cannot sl**p alone

English is not my primary-language, so be gentle with me. But wanted to share the story of my fantasy. 

As I lay here in my own bed with cum on my back sliding down in between my ass, I think to myself.. How did I get here? I'm now officially a fucktoy, a worthless sissy that lives only to serve cock. The first cock has conquered me.
However the crave of cock started already when I was young. When I was drawing dicks on a paper thinking to myself that is looks so marvelous, so big.. so tasty. I would spend nights jerking of thinking of cocks and taste my precum. And each time I saw a porn... Continue»
Posted by sirington 3 months ago  |  Categories: 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 3 months ago  |  Categories: Anal, 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 3 months ago  |  Categories: Anal, 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 3 months ago  |  Categories: BDSM, Interracial Sex, 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 3 months ago  |  Categories: Anal, First Time, 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 3 months ago  |  Categories: BDSM, Fetish, 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 3 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 3 months ago  |  Categories: BDSM, 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 3 months ago  |  Categories: BDSM, Fetish, 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 3 months ago  |  Categories: BDSM, Gay Male, Shemales  |  
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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 3 months ago  |  Categories: Fetish, First Time, 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 3 months ago  |  Categories: Fetish, 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 3 months ago  |  Categories: Fetish, 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 3 months ago  |  Categories: Gay Male, 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 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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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 3 months ago  |  Categories: Anal, Shemales, Taboo  |  
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Hitch Hiking across Europe

I wanted to go visit my cousin in Germany but couldn't afford it really, but on a whim I decided to go for it, just pack a few essentials and hit the motorway with my thumb out. Anyway to cut a long story short I finally got a lift from a couple in a nice big Mercedes, and started chatting, like you do about everything and nothing, when we came to a service station and they had to fill up with petrol and have a bite to eat, explaining i was kinda broke, the wife says that is okay, we will buy your lunch in return for a favour, and nothing else ......we sat have a meal and coffee, and the... Continue»
Posted by gkaye1954 3 months ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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sissy blackmailed, gang banged, then ruined.

*This is my first story ever, I have no writing background whatsoever, in fact I failed every English class I ever took.. This is simply my fantasy, with a little bit of my real life experiences mixed in here and there. Parts of this story may be sadistic and extreme.
My apologies if the story is a little s**ttered.. You will just have to deal with it! :)

Please be kind, but honest and let me know what you think.


Chapter 1
The beginning.


Buzzzzz, buzzzzzz... My cellphone vibrated on the night stand beside my bed. I groggily felt around in the dark until I got... Continue»
Posted by submissive_boy1990 3 months ago  |  Categories: BDSM, Group Sex, Shemales  |  
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Paw-Paw and His Sub

“When you gone let Paw-Paw back in that ass, baby boi,” the sixty-six year old man asked.
“You tell me when you want, Paw-Paw,” cooed the short caramel-skinned twink.
“Aww, you know I want it now!”
“Come get it.”
“I can be on my way in thirty minutes.”
“Okay, baby!”

Rufus Clark went into the bathroom. He washed up. He put on a two-tone blue and cream long-sleeve walking suit, a pair of brown leather Stacy Adams slip-on loafers, and a brown Fedora hat. As he walked out of the house, he yelled to his aging mother, who lived with him, that he would be back late.

Rufus got in his green... Continue»
Posted by faggyboi 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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The Pill - part 3

This is the third chapter in the story of my adventures in London, on the day when I took a small pink pill and my face and body transformed into that of a beautiful young woman. However, I knew that I only had 24 hours before the effects wore off and so determined not to miss any opportunity as I had a day of sexual adventures, some planned, some on the spur of the moment. The story so far: I had started my day in the back of a van, in a multi-storey car park, choosing the outfits I would wear during the day, and discovering the wonders of my new female body. I had then greatly improved the d... Continue»
Posted by mallenwc 3 months ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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