Shemales Porn Stories
Page 60

Virgin Sissy learns her place in life

As with any relationship, things change. The suprising thing that happened between me and Martin was at the begining he was a bit soft and I was the dominant person. It could have been that he was new at college and a bit shy. But as the summer went on he bacame a member of the Football, Tennis and Hocky teams. All the better as far as I was concerned as he had three different kits for me to sniff and lick after he had been playing. Blue top,shorts and socks for football, white t shirt shorts and gym socks for tennis and Blue top and white socks for hockey.
One Saturday, Martin turned up at ... Continue»
Posted by igglepiggle 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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Riverbank Tranny Fucktoy

Hello to all of you that read my first true story about outdoor sex. This is another account of a meeting I had in the middle of a city near a river.

It was late one summers evening when I met up with this sexy young Portugese stud I had been messaging on a gay dogging site.

I had been chatting to Fillipe for a couple of hours, and we were both getting hornier and hornier with each new message that we sent. It was me that asked if he would like to meet that night, and he of course said yes. There are a few cruising areas near around the closest city to me and we arranged to meet at one... Continue»
Posted by donnamarie09 7 months ago  |  Categories: Anal, Shemales, Voyeur  |  
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Crossdresser's Rough Sex

To start things off there is something you need to understand. I am bi sexual, but when I am with a guy I am a submissive bottom. I love to pleasure other guys. That's how this experience came about.

I was out for a drink with a girlfriend, catching up on the latest gossip when a voice whispered in my ear

"I can see your knickers."

I spun round and saw a moun5ain of a man, he looked like a chubby lumberjack, all man and really butch. I blushed and panic as no one knew I was wearing panties or stockings. It turned out that when I sat down my pink panties were visible over the top of my... Continue»
Posted by MacDaddy714 1 year ago  |  Categories: Anal, Shemales  |  
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A New Dawn Arises






A New Dawn Arises


-


Chapter 1

The Arising

To celebrate my transformation and to increase the effect of my
feminization, Mistress Lynn decided a name change was in order.

"What's a good name for a useless, slut French Maid," she asked herself
aloud. "I shall call you Dawn. I think it's appropriate because you are
at the dawn of a new way of life."

Another belt was strapped around my waist. It had a number of loops. My
mistress attached my wrist restraints to the strap.

This allowed me lim... Continue»
Posted by klammer 1 year ago  |  Categories: Fetish, Shemales  |  
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A Black Tranny Fantasy

It was only when she emerged from the bedroom in a purple silk nightie that not only clung to her full breasts, but also betrayed the hint of a bulge between her legs, that I realised that it was actually going to happen: my fantasy of sl**ping with a black shemale was about to come true. She paused at the bedroom door and smiled at me.

'You like what you see?'

I did indeed, but my mouth was too dry for me to say anything, so I just smiled back and nodded. Sasha looked as good as in the picture I'd seen online on the e****t site. Chocolate brown skin, soft, generous lips, a cute smile, b... Continue»
Posted by amylee-jones 9 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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My sissy son,by his dad and lover. Part 2

Hi,thought it was about time i let you know about my son and me.

This is Part 2.

So...there i was,on my knees staring at my son's beautifull cock. Not big,only 4" long..but sweet with a nice head and completely shaved..(or waxed). "Oh Jack...suck me please...pleeease...been ages since a handsome older gentleman touched me there." Pre-cum was leaking from it...and i licked the end...and gently took him into my mouth! He moaned and slowly made his hips go forward and back...gentle movements like he was fucking my mouth.I was sooo horny at this point i would have done anything...so i did...... Continue»
Posted by chocandres 4 years ago  |  Categories: Anal, Shemales, Taboo  |  
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The Surprise Visit

I had been chatting for some time online with a guy who said he liked crossdressers and loved getting his cock sucked. we chatted numerous nights, roleplayed online. i guess, i don't remember, but i guess i gave him my address. but i worked long changing hours. one thursdau night about 2 am i was coming home from worked, turned onto my street when i saw a strange car parked there. as i drove by its headlights came on and it pulled out following me. i parked in my driveway and watched as it slowly drove past me. i was in the house about 3-5 minutes when i heard a car door shut then footste... Continue»
Posted by cdamanda 4 years ago  |  Categories: First Time, Hardcore, Shemales  |  
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#1 - Nikki's First Experience

I had recently started my transformation and was just past 18. I was at the stage where I was just starting to dress as a female in public and friends convinced me to go out. At the local pub over the course of the night my friends all found someone and I had resigned to the fact that I probably wouldnt find anyone until a young guy in his mid 20’s approached me. He said my friends has told him about my change and he was very complementary saying I looked pretty convincing. Over the next hour or so we spoke in the pub about everything from jobs, hobbies and eventually if we were both single wh... Continue»
Posted by Nikki_93 3 years ago  |  Categories: First Time, Shemales  |  
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Cindy Growing Up

My first memories are of my mommy playing dolls with me in my
crib, and singing softly as she nursed me. I grew quickly, and I
was a chatty little k**, and by four Mom would take me out to
play with the other little girls. I remember always being dressed
in skirts and layer after layer of soft, frilly underwear.

I was treated like a little princess, and by five I was told that
my father had died just after I was born, leaving Mom enough
money to raise me without worry. I also learned I was different
from the other little girls. Mom explained that some people are
born without parts, ... Continue»
Posted by alex_wd 2 years ago  |  Categories: Fetish, Shemales  |  
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Gina C

A number of years later, after my first shemale expereince, I still had a penchant for a hot shemale or a slender sissyboy who was passable. That's when I met Gina, who fit the mold of a slender sissyboy who was much more than passable, she was gorgeous.

The first time we got together was on a rainy Sunday afternoon. My wife was out of town and I was cruising aroind on AOL in the SoCal Shemales chatroom. I came across her screenname and we started to chat. We traded writen descriptions of one another and she sounded very hot. She was white, in her late 30's and was married like me. Sh... Continue»
Posted by Blackpapi65 8 months ago  |  Categories: Shemales  |  
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Mt tranny story

I've been dressing like a girl for the past three years. I've been a girl my whole life though. I always knew I wasn't the same as the other boys. I tried desperately to blend in and be a normal boy but couldn't. Behind the scenes, at home, I'd raid the laundry basket at night and grab some of my older s****rs clothes and underwear, rush back to my room, lock the door and indulge. I don't know right but even from a young age something about wearing woman's clothes was very liberating for me. From the age of 12, every night without fail I slept in a pair of French knickers. I had a set of girly... Continue»
Posted by stevolayton 5 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Babysitter

A K little s****r Alyssia


Babysitter

I had been watching Paul and Nicole's two c***dren for a while. She was
very pretty, about 5'8", nice legs and loved to show them off. She towered
over my 5'6' in her heels, Paul was about 6'1 or so, clean shaven and a
trim wide shoulder athletic build, they made a very good looking couple.
They would go out, she in a sexy dress and heels, and he in nice pants and
shirt, or a suit sometimes dancing or parties I guess, I never really
cared. It was a cool gig, the k**s were young, and went to bed around 8 or
so, so I had lots of time to mys... Continue»
Posted by jayymie 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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Shemale Cam Girl Sample

Sample from "The Shemale Cam Girl" available on Amazon (http://www.amazon.com/dp/B00R0BADB8).

“Yes,” she pushed him down onto the couch. “Look, if you are going to suck my cock you are going to have to get better at it. I don’t just let anyone suck my cock, you know,” she shook her head and laughed. “I mean, you saw it? That’s not the kind of cock you just let anyone suck on and Joel, hon, that was not a very good blowjob.”

“I’m sorry,” he hung his head, not sure how to respond.

“No, it’s okay,” she lifted his chin up, leaning in and planting a kiss on his lips. “It was your first tim... Continue»
Posted by rehumanize 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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Cross dressed slavery

Oh just try it on, don’t act so…stereotypical.”

I started to protest again, I mean I was not trying to be a jerk, but I did not feel like serving as Leena’s dress dummy all afternoon. I felt uncomfortable enough around her and her clothes. The way she dressed made me crazy and I knew she would tease me all afternoon if I let her. It was my own fault really, I approached her at her last ‘fashion show’ and offered to take some pictures. I really did like her designs, but mostly because of my own peculiar fetishes. Leena worked a lot with sweaters and wool, knit creations she called them, ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Horse Cock Girl Part 5

Author's note:

I got a fair bit of feedback on Chapter 5, stating that the chapter were too short and that the description had been lacking.

I know this will end up being under a page on here, but it is the second-longest chapter yet. I hope you all enjoy the work I put into it.

It's not been easy to keep this story going for so long, so I think I'll likely only write one or two more chapters to wrap it up. I'm not sure how it'll end, so please, don't ask me.

Once again, thanks you too everyone that reads the story. I hope you enjoy it and I welcome constructive feedback.

***
... Continue»
Posted by drew1207 4 months ago  |  Categories: Fetish, First Time, Shemales  |  
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Cumming for Christina

I love you and will see you Friday night I told my wife as I hung up the phone. My heart began pumping big time as I hung up from my nightly call and the familiar ring of a new text sounded off. My cock stirred just seeing it was from Christina. The message read that the rendezvous was on for 10:00 with a room number and hotel. I cleaned up nice and fresh grabbed the condoms and lube and headed out.

My stomach was in knots as Christina answered the door. I quickly entered and stood frozen staring at her beauty. After months of exchanges on Xhamster we were together. Within seconds our lip... Continue»
Posted by iheartm2f 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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The Slut on the Balcony

A night away from home on business always meant a night of crossdressing and exhibitionism. I loved to get a room with a balcony so I could easily be seen by men walking around the motel grounds. This night I'd dolled in in a black lace corset; heels, hose, and g-string. I slipped on a leopard print short spaghetti strapped dress over; poured some wine and strolled out onto the balcony. My red wig flowed over my shoulders and my make up was just a bit slutty. I put on a choker that spelled out cumslut in rhinestones around my neck. I just knew that I would get lucky this night. Another mo... Continue»
Posted by dana213 4 years ago  |  Categories: Group Sex, Shemales, Voyeur  |  
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Tabby Cat: Sex KItten

This story was posted under my old profile, sluttycdprincess, and I'm reposting it.

OK. So, this is my first story on any site, and I'm finally pleased enough with it to post. Hopefully people will enjoy it and if so I will definitely be writing more. Leave me comments or PM me about it if you want, I would love the feedback. I plan on making this a series, with all of the characters making more appearances and being fleshed out more. I also would like to write the story of my character leading up to this point. Her Origin story so to speak. Obviously the main character is transgendered as... Continue»
Posted by summer_angel_cd 6 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Last night I drank my own cum

Once upon a time...

There was a regular boy, who was always fascinated by women, but one day (casually) discovered the dirty and horny world of the "third way" of sex, the fantastic shemale-ladyboy-tranny universe, and it was like a shock for him, a very sweet shock, he never believed or thought in exciting himself by watching a girl with a cock, but instead that new world electrified him, and made himself very curious about these she-males, widening his love above women and becoming a real sex pig and an orgasm addict.


Well, that regular boy was me. I consider myself as ... Continue»
Posted by Porcellone 3 years ago  |  Categories: Masturbation, Shemales  |  
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IT WAS SO WRONG BUT SO NICE WE WAS JUST HAVEING FU

IT WAS WHEN I WAS 17 NEARLY 18 MY MOTHER AND FATHER SPLITT UP WHEN I WAS ABOUT 12--13 AND I LIVED WITH ME DAD IT WAS ALL GOOD WHEN I WAS 15 ME DAD MEET A NEW GIRL FRIEND CAFFE SHE WAS YOUNGER THEN DAD HE WAS IN HIS LATE 40,S SHE WAS IN HER ERLY 30,S THEY WAS WITH EACH OTHER FOR A WHILE THEN CAFF WAS MOVEING IN OWR HOUSE IT WAS COOL I WAS WITH A GIRL AT THIS I LOOK,T AT CAFF AS ME STEP MUM WE USE,T TO JOKE ABOUT HOW DAD WAS 17 YEARS OLDER THEN HER AN I,D SAY THERS THE SAME AGE GAP BETWEN U AND DAD AND ME AN U SHE WOULD SAY NO IM AN ADULT SO IS YOUR DAD U R STILL A TEENAGER WELL ATHTTER 2 OR 3 Y... Continue»
Posted by needyboy 4 years ago  |  Categories: Shemales  |  
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