Shemales Porn Stories
Page 60

Poker Night Part 4

I wake up the next morning, dried cum on my face. It was already a little later than usual. Mistress and Master come into my room. "Is my little sissy all ready for a big day today?" She said. I bounced up and down excitedly, giggling at her every word. "My goodness Craig! You couldn't even clean her up after you came all over her precious face?" "I was tired, and I'd thought it'd make her sl**p easier." He said. "Is he right sissy? Did having real man cum on your cute little face help you sl**p better?" She asked. "Yes Mistwess, having Massa's cum on my face put my fas asweep" I responded. "W... Continue»
Posted by ConvertedGirl914 1 year ago  |  Categories: Gay Male, Shemales  |  
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Tranny tricked the Postman

A true story…

I’d woken earlier than I’d wanted for a rare day off from work and decided to see if I could have a little fun.
So I did my make up and found the longest false lashes I had, touched up with the darkest mascara there is… with a touch of glitter… bright red lippy, a naughty smile, get the picture?

I put on some sexy underwear and a black lace top, little skirt with heels and hold-ups… I was on the hunt for cock but how could I trick a complete stranger into some naughty fun with a horny tranny??… I had a plan…

I was expecting a parcel in the mail that was too big for the... Continue»
Posted by JoanneCoxTV 1 year ago  |  Categories: Shemales  |  
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A Warm Cum Bath, on Sara's Hen Night

Part 1. The Meeting with Alise

No one can say that Swedish girls can't attract attention, especially on their last night of freedom, on the eve of their betrothal, some will be found d***k, and some found stripped nude, and even some having a last minute sex with old boyfriends and so on, but one, only one had the experience, most girls cream their knickers thinking about, and this is her and her e****ts account, of her wildest fantasy come alive, the night 200 men ejaculated onto her, boys and men alike, all strangers, doing what men like to do to a beautiful blond 18 year o... Continue»
Posted by MarieL 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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Russian Shemales

(Translated from the Russian)

We lived in small village, no work, nothing to do but smoke all day. Friend Serge and I sitting by road one day, when black sedan, shiny from city stop near us. The man inside wearing a expensive suit, and ask if we want jobs as models.

Serge and I think must be joke. But man introduce himself as talent scout. He speaks Russian but with accent I don't not know where from. He says he is from modeling agency and is looking for new talent to model. Introduces himself as Mr. Aronoff, and asks us to stand and turn around. Looks closely at our faces. Serge... Continue»
Posted by TransContinental 1 year ago  |  Categories: Shemales  |  
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Young sissy loses her virginity (true story)

So this is a true story about the 1st man that I ever met. I was about 13/14 years old and had been talking to a much older man over the internet. He was about 50 if I remember correctly.

I had been dressing in my mother’s underwear and dresses for a few years and found it so sexy, I had not considered myself gay or bi, I just knew I belonged in female attire, it made me happy and felt natural.

The thought of pleasing this man made me excited, terrified and scared, but very excited. I could tell from my little clitty. After chatting for a few hrs he wanted to meet me?

I had never me... Continue»
Posted by Subtvnicola 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
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Straight, to Bi, to Gay, to Trans, to Straight (Pa

I don't want you to think we simply lived happily ever after. Nothing is that simple.

We've had our ups and our downs, and our ins and outs. We've had three major hurdles, so far. The first was me freaking out over the idea of having a boyfriend. As natural as it seemed to be with him, and as mind-blowing as the sex was, it was still a huge shift in thinking for me. The second hurdle was coming out.

The third was his affair. But more on that in a minute. As I want to talk first about coming out. Friends and f****y may say they support gay rights and all, and they may be fans of... Continue»
Posted by TransContinental 1 year ago  |  Categories: Gay Male, Shemales  |  
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Jeremy's School Bully

Jeremy hopped off the bus in front of his new school. He lived close enough to walk, but had decided to ride the bus instead. He wanted to see what it was like, because he'd never rode the bus at his last school, he had always walked. The school was a hulking sandstone building that loomed over the small front lawn like some mid-evil wyvern, gobbling up c***dren every morning only to puke them back out onto the lawn in the afternoon. Over the years acid rain made long dark streaks of black and brown down its façade making it look as if Mother Nature had raked it with her claws. It was a post w... Continue»
Posted by test2012 1 year ago  |  Categories: Shemales  |  
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Portuguese Summer part3

After that night with Alan and the girl back at the villa i was very nervous about going back into work the next night , i was just not sure how much he had felt while he was fucking the girl with me under her or even if he was aware of what happened. When he turned up for work at the bar about 20mins after me he pulled me to one side and just grinned at me and asked if i had enjoyed it
I sighed with relief and said "yeah it was great fun,he just grinned again and said ok ...well if we ever get the chance lets do it,ohhh and i saw her give you her thong as she was leaving and i saw you puttin... Continue»
Posted by julieanneff 1 year ago  |  Categories: Anal, Masturbation, Shemales  |  
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Portuguese Summer part2

I have been in Portugal now for 2 weeks Paul has phone to say he wont be coming out for the rest of the summer as his dad is in a bad way , His mum has asked if i will stay in the villa and look after it for them until the end of august, of course i said yes, but i was getting bored and needed to get some work as the little money i had was not going to last long.
Since Paul went back home i have discovered that i love to dress up in his s****rs clothing that she has left here , and boy has she left a lot of stuff, I have full shaved my body and have started to become quite good at putting on ... Continue»
Posted by julieanneff 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Portuguese Summer part 1

i`m not tall, in fact for a guy i am quite short at just 5ft6in and very slim for a guy as well weighing in at just over 8 stone, so girls friends have been a little hard to come by but i have had a few over the years, 2 in fact but one of those was when i was 14 the next one came 3 years later.
So now at 18 years old i am jobless and without a girlfriend and its just coming to the summer.
Paul is my best friend he is from a well off f****y and he turned up at my house one day in June and asked if i wanted to head out to Portugal with him for the summer, His parents had a 2 bedroom villa out... Continue»
Posted by julieanneff 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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First Time - Surprise Shemale

I'm an eternal masturbator. I've always like wanking and playing with myself. At a young age I worked out that I likes playing with my ass hole, sticking things in it, walking round all day with something in it. With the advent of the internet I was like a pig in shit. So much porn to be had and so many things to see and do. One day I discovered the true beauty of the shemale. Wow. Gorgeous women, with cocks. Prior to this it had been women with strapons that got my attention, but this? Perfection. Then cam the webcam. I found a couple of sites where you could interact with such beauties and c... Continue»
Posted by hungrymanx 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Poker Night Part 3

Everything was black. I couldn't see a thing, but I heard everything. ""Obey! Suck cock! You are a sissy! Worship cock! Obey your master! Obey!" over and over again. Every time 'cock' was mentioned a giant one flashed before me. And every time 'master' was said I saw an image of Craig. I didn't know what was happening, but after a while I accepted it. I woke up dizzy, my mouth open and dry. Sweat covering my body. "What was that all about?" I thought. It was morning. I got out and made breakfast for myself and Craig. "Goooooood morning" Craig said from behind me. I turned around to say good mo... Continue»
Posted by ConvertedGirl914 1 year ago  |  Categories: Gay Male, Shemales  |  
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Horse-Cock Girl Part 3

Transsexuals & CrossdressersHorse-cock Girl Ch. 03
Horse-cock Girl Ch. 03
byjoshy029©
Author's Note: This story isn't the end of Horse-cock Girl. I've got another in mind which is why this one ends rather suddenly: the next chapter will follow on directly from this one.

The new character, Scarlet is devoted to a good fiend of mine who is a huge fan of this series. She created Scarlet and everything about her, all I did was write it down and turn it into a character.

I've been toying with the idea of a Q&A session with the characters of this series. If you would like me to write it, le... Continue»
Posted by drew1207 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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S****r has a Secret part 3


Sarah was sat on her laptop, searching for something on the internet. She wanted to surprise Hope with something for her official leaving of school.

She'd been looking up the cheapest, quality flights she could get to take them both on holiday for a week or two, but she'd been hampered a lot by Hope wanting to hang out together. Hanging out normally involved sex, after which Sarah had little energy left to search.

Luckily, Sarah had the day off work while Hope was sitting her final exams for the year. She was looking through the normal travel agent websites while also looking on other ... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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Sheena

by Jennifer Lorissa-Leigh


"I tell you, Arnie, something's going on in there." Jeremy spoke as he and his friend looked upon the university's Institute for Human Sexual Studies. "I know Jerry went in there, and never came out."

"Maybe he just quit school and went home to Nebraska, like they said," Arnie suggested. "What could possibly be in there that would cause someone to disappear?"

"I don't know. Some kind of foul play's going on... maybe one of the professors is a serial killer, or something like that. I gotta get in there. I'm getting to the bottom of this."

"Why don't you c... Continue»
Posted by PaRiaH236 1 year ago  |  Categories: Sex Humor, Shemales, Taboo  |  
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The Transformation part IV

Mistress Anna woke me from my nap. Her hand was gently brushing my cheek and she was telling me, "what a good girl you are! You even crawled here and licked up your mess! This dried spunk on your face just won't do though. Go to the bathroom and wash it off then shower and we'll get you dressed and put your make-up on."

I rose from the floor, thankful that they had set me free of handcuffs. I still was locked away in my metal chastity cage so I suppose they didn't figure the handcuffs were necessary. Mistress Anna slapped my ass as I walked into the hallway. I could hear Mistress Heat... Continue»
Posted by fictiong 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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The neighborhood sex slaves Part 2

Jack and the girls had gone home about an hour ago and I was in the gym working out when I heard the front door open. Kelly came bounding in calling out my name.

I told her I was in the gym working out.

Kelly sauntered into the gym wearing my favorite little black skirt and red tube top with a "cheshire cat" grin on her face. My cock stiffened a little when I saw her. She came over to the bench where I was now sitting up, straddling my legs and sat down. She looked at me in my eyes and said "I've missed you honey", "Did you miss me?"

Wrapping my arms around her waist, smiling, I said ... Continue»
Posted by Bigrodtaz 1 year ago  |  Categories: Anal, Shemales  |  
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Appointment By Card Only. part six

His landlord was not best pleased when Bruce announced his immediate departure, but was happy to hand him a bill requesting three months rent in lieu of his vacation without notice. He packed his laptop and the few items of decent clothing and sparse possessions into a sports bag and slung it into his car, then drove back to the house, his mind racing; he could not believe what he was doing, his rational thinking telling him to turn away, but the draw of the magnificent controlling woman and a life which consisted of perpetual sexual excitement drew him to her. The plug teased his anus, remi... Continue»
Posted by midsummerman 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  
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My fucking f****y

I'm really proud of this would love some feedback


Why was I on all fours with my dad's cock in my ass and my s****r's pussy in my face? Well little did I know that my mom knew about my secret. She knew that I had been wearing her and my s****r's lingerie.

It started when one day I was home alone and wandered down to the garage to play around on the air hockey table. I got bored and looked around as we had a lot of stuff down there. Boxes were piled up on one side and I looked in a few of them and found something that made eyes pop open.

I saw a naked girl on the cover of a magazine... Continue»
Posted by 6270daniel 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
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my first encounter

i had been with my girlfriend for over a year now, and our sex life was amazing, but i wanted to try something new. i wanted to try role reversal. i had never mentioned this to her, and i wasnt sure on how she would take it. one night, i decided to bring it up to her.


" ummm, hunni..can i ask you something?' i said.


" sure, babe, what is it?" she replied.


"well, i wanna try something different. i want to try role reversal, where i dress up as a girl, you wear a strapon, and you fuck me in the ass. what do you think?:


: wow, really?...you know, i think i could be fun..umm... Continue»
Posted by SashaCD 1 year ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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