Shemales Porn Stories
Page 59

#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  |  Views: 1675  |  
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Island Fantasy

Part 1

My ship arrives off shore at about 10 in the morning local time. We drop anchor about a 1/4 mile out and busy ourselves with getting ready for some shore leave. I'm very excited because I've only been on the ship for about 3 weeks and I'm already getting to go to a new and exciting foreign country.
As I look over the sides of the ship I see a large crowd of small vessels starting to appear. They're locals, fishing boats, runabouts, and all of them loaded with people staring up at us.... at me.... I wave and they wave back. Friendly.

When its my time to depart the ... Continue»
Posted by SandyCrossdresser 1 month ago  |  Categories: First Time, Shemales  |  Views: 1674  |  
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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  |  Views: 1673  |  
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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  |  Views: 1672  |  
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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 4 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1671  |  
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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  |  Views: 1670  |  
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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  |  Views: 1670  |  
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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 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1671  |  
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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  |  Views: 1668  |  
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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 6 months ago  |  Categories: Shemales  |  Views: 1668  |  
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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 3 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1668  |  
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Becoming Aphrodite Ch 01

My wife and I have been married for 10 years. She is a beautiful brunette of 5'8" and 120 pounds. With her long hair and her cute and innocent face, she looks a lot like the porn star Cheyenne Silver. I would dare to say she's even prettier: her extraordinary green eyes are totally unforgettable and even the famous porn star I mentioned could not compete with her.

We got married very young and we were very happy for many years but Jennifer was slowly changing, discovering parts of her which could not be ignored any more. In fact, she did not have enough sexual experience before getting marr... Continue»
Posted by slutyvanessa 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1667  |  
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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  |  Views: 1667  |  
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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 5 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1666  |  
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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  |  Views: 1664  |  
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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  |  Views: 1663  |  
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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  |  Views: 1663  |  
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Wife was Away!

I hadn't been out for over a month and it was starting to bother me. Since I started dressing four years ago most of my excursions in public have been from fall till spring. Its easier to hide my shaved body in the cooler months, which makes me feel much more feminine. When I'm smooth all over I get to wear more revealing clothes and I can let the guys I meet run their hand anywere they like without them getting turned off by unwanted body hair.

My wife was about to leave town for ten days at a convention she attends every year and as soon as I dropped her off at the airport I ru... Continue»
Posted by kristygurl 4 years ago  |  Categories: Shemales  |  Views: 1660  |  
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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  |  Views: 1661  |  
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Walk his way

Just for the thrill of it all, I moisturized my freshly shaved body, combed out my long hair over my shoulders, and put on a pair of very short cut off denims, cuffed them even shorter, and a Betty Boop T shirt with the neck and sleeves cut out. I looked and felt very much on the fem side. Not really crossdressed, but without a doubt, sissified. I drove down the interstate to the nearest rest area and parked all the way at the end. I carried my little belly bag like a handbag, and walked to the rest rooms with a swish in my step and a grin on my face. Most people did a bit of a double take; a ... Continue»
Posted by dana213 4 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  Views: 1656  |  
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