Shemales Porn Stories
Page 79

My New Girlfriend Turns Out to Be a Shemale.

Where do I start?
How about at the beginning. My name is Cal I am divorced and living alone. I am not a bad catch I am five foot eleven, short black hair, green eyes and no visible scars. I am a regular at the gym so I am in shape but not ripped. A seven inch uncut cock that I can use well. I dress nicely and have a good job.
My friends Don and Lisa were feeling sorry for me they knew how ugly my divorce was and how lonely I was so they invited me to their pool party last weekend. They said there would be some single women there and I might find someone I like.
Okay, I thought at... Continue»
Posted by triphammer73 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Bar trap 2

Bar Trap 2 (Part time whore)

I was supposed to put on heavy makeup. Starting with the foundation, I
applied a generous layer of a brand especially designed for the use on
stage, that did a very good job covering up any dark shadows. After I
was satisfied with the effect, I used a brush to put on powder and make
it all smooth and feminine.

Next I did my eyes, first with a black eyeliner on the lower lid, then
a white, thicker one on the upper lid. Black shadow followed, and white
towards the eyebrows. Three coats of mascara on both lashes to make me
subtly wink with them at anyone ... Continue»
Posted by trans_michelle 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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A night of passion

Will led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sarah lightly ground her ass into his crotch, rubbing herself against his hardening cock.

“Mmm,” She moaned, feeling Will’s lips kiss the nape of her neck, causing her to break out in Goosebumps.

She turned to face him, wrapping her arms around his neck, drawing him close. They kissed, tongues intertwining. Will could feel the hardening bulge ... Continue»
Posted by gellid 4 years ago  |  Categories: Shemales  |  
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Shemale snapped

(A story written by a friend) Hope you like it!

Camilla took a few steps out the door of her balcony to get a feel for the temperature. Thankfully it was cool out. It had been a hot day, which meant a cool night was welcomed.

She closed the door and pulled out a pair of gold hoop earrings. She was suffering from a mild case of the jitters. There was a date on the agenda tonight with a guy she'd been seeing for a couple months now. Camilla kicked a pair of high heels out of her closet while fastening the earrings.

A date was a big deal for Camilla. Even though she'd been out of schoo... Continue»
Posted by Ankakalle 3 years ago  |  Categories: Shemales  |  
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moms friend 2 - dressup slut

so I had been visiting Linda for about 8 weeks. Every oportunity I got. My mom was none the wiser. I'd invented a girlfriend that I was seeing. Linda had backed up this story by telling mom that she had seen me with her.

little did she know I was visiting her best friend to dress up as a whore every chance i got.

Linda had had to lay down some ground rules. I had to dress in the outfit she had picked out for me as soon as I entered her house. She would watch me dress.

Linda insisted I wear suspenders and stockings. I was fine with this as i just loved the look of my cock, framed by la... Continue»
Posted by hornyTVluvr 3 years ago  |  Categories: Fetish, Group Sex, Shemales  |  
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The real me part one

Well let me began Iam not in the closet, I grew up in small town my mom raised me cuz my dad was not around. This town was dead and in my school days there was only myself and friend of mine that were the only k**s in town. It was summer and my friend had left to go spend the summer with his grandmother in other state.
My mom was a 5'9" 130 lbs d breast woman that raised me and worked her but off doing it as only hair stlies around for a 100 miles. She always wore dress and skirts and heels dolled up everyday. So oneday I was bored around the house when she was home taken a break. We were... Continue»
Posted by cdpaula 3 years ago  |  Categories: Gay Male, Shemales  |  
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A LadyBoy For My Wife

I have been happily married to my sexy Thai wife Lisa
for three years now. My wife is Thai is petite (5'1")
with a stunning figure, a tight ass and long waist
length black hair. We had met in a bar in Thailand and
subsequently we were married back here in the UK. She
was very loving with me but not very sexually

My attractive wife and I have sex often as we watch
porno movies. Often we role play and we fantasize about
my wife fucking other guys. Since my visit to Thailand I
often dreamed of a beautiful Thai Ladyboy chick joining
us for a fuck too.

When ... Continue»
Posted by sanpeesua 3 years ago  |  Categories: Fetish, Hardcore, Shemales  |  
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Trip to LA

I was out in Los Angeles on business and as I would dress up every nite and see if there was anyone who wanted to play a bit. On Friday around 5 pm I decided to go all out and I dressed in a corset with garters, panties, bra, stockings, red heels and a black lace cocktail dress. I finished it off with a blond curly wig and some rhinestone earrings. I had taken my time with my makeup so I looked pretty hot.
I had some conversations with Tom during the week but they always ended up with just talk so I figured Friday’s conversation would be the same. I was chatting with a few guys as well and... Continue»
Posted by MichelleSEmass 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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A TV in the Shoe Store

I work at a ladies shoe store at a large metropolitan mall.
My name is Jillian, though my friends all call me Jilly.
Those same friends also say that I am blessed with a
beautiful face, and an athletic body! Pretty heady for a 30
year old woman whose ideas of athletics never got beyond
sports illustrated and Cosmo! But friends tend to flatter,
that is why we are still friends! I tend to dress with a
flare towards teasing. You see I always wear my skirts and
dresses a bit shorter than fashion demands, and I always
wear sheer reinf***ed heel and toe stockings. A habit
started by a ... Continue»
Posted by jillynylons 4 years ago  |  Categories: First Time, Shemales  |  
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I Knew Her Secret

I had a serious crush on the postal lady, I would wait on her until I saw that she was coming and then I would either make up some reason to go outside and exchange words with her or I would watch naked from inside of my house. I know it sounds perverted but I just couldn’t get enough of her. Her name was Marla. Obviously, she wore the whole postal get-up with the blue shorter than usual shorts on a daily basis. Usually the post ladies when they wore shorts they would come to the knee, Marla’s came to the mid thigh and were very tight and revealing. She was African-American and had sugar brown... Continue»
Posted by 1234spence 3 years ago  |  Categories: Gay Male, Shemales  |  
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crossdressers first time

i first started to wear tights when i was 18,i was shocked when i first realised i loved tight panties and sheer tights. i was staying with my friends mother who was 65 at the time,she wore the sexiest lingerie i had ever seen,especially on a woman that age,but i felt drawn to the sheer stockings. the next day i was taking a bath when i noticed them on the wash basket,i had an urge to wear them,i was very shocked by this desire but had to!i slipped them on taking care not to rip them,they were hold ups and as soon as they were on my cock stood to attention like never before. to my horror my fr... Continue»
Posted by nylonfiona 5 years ago  |  Categories: Mature, Shemales  |  
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How I became a GURL

So how did you become a gurl?

That's the question almost everyone I meet or chat with asks me... how did you become such a sexy transvestite, when did you figure it out, when did you learn you liked cock.

I actually love the question, because it turns me on to answer it.

When I was 15 or 16 I used to sneak into my parents room, find my dad's stash of Playboys and jack off to them. The girls were sooooo beauitful, I just couldn't believe it. I wanted to see and touch one, which led -- I guess this is common among us gurls -- to digging into my Mom's stuff.

When I was left alone I w... Continue»
Posted by jenn1 4 years ago  |  Categories: First Time, Lesbian Sex, Shemales  |  
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Sissy Emma is Turned Chapter 4

I couldn't go outside dressed like that could I?

Here I was f***ed to dress like a slut in locked on heels, barely black stockings, mini skirt, frilly white blouse with which could clearly see my black bra and 38d breastforms and heavily made up face. I would have looked like a reasonable vision of a woman, albeit a very slutty woman other than the fact that my new Master and my ex-wife had failed to give me a wig. So to anyone seeing me it would be clear that I was in fact a feminised male. This was going to be humiliating.

But I couldn't think of a way out. At the least it was going to... Continue»
Posted by emmahighheels 2 years ago  |  Categories: Shemales  |  
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Slutty Sissy Used in a Cheap Motel Part 2

After being fucked and bred by the first 2 strangers and watching my sissy hypnosis videos I was definitely ready for at least one more deep fucking. It was around 10 p.m. when the next guy knocked on my door. I opened the door to find a very large black man about 6'8" and a smaller black man who was about 6 feet even. I invited them both in and was very excited that I was going to be tag teamed by 2 black cocks. These two guys were very demanding and knew exactly what they wanted. I knew that I would do whatever they told me to do, because every ounce of my male thought process was gone and m... Continue»
Posted by cumslutchloe 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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What If My Mom Part 2

Peggy and Me

We all lay together for a while until Mom told us she had to get up, it was lunch time. We had not heard from Bobby or Dad and I was getting hungry. "You two just stay here, I will make some sandwiches. Back in a minute"

Just as Mom left Peggy rolled onto her side facing me, "That was so nice kissing your Mom.........., will you kiss me, down there?".

My feelings were still mixed up, but I did want to. I could show her what Mom had taught me. When I moved to get between her legs she stopped me. "No together, I want to suck your cock at the same time, you know".

Peggy p... Continue»
Posted by chchboy 3 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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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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"Not MY Type?"

I’d known Kelly for most of my life. Growing up I spent most of my time at her mother’s house. It was a way to escape and avoid my parents constant arguing and fighting. It was a pretty well established fact that Kelly was lesbian early in Junior High School. Her mom and I became quite close as I was rapidly replacing the little girlie daughter she was losing to an ever increasing “butch-ness”.
By twelve years old I essentially become like a member of their f****y. Over the next few years they had the opportunity to watch me morph from a small frail Christopher into a pretty, petite and... Continue»
Posted by chrissieCD 3 years ago  |  Categories: Anal, Shemales, Taboo  |  
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CD dream too cum true?making plans True storie

This has always been a dream of mine to do bare back with a few guys same night. Plans are in progress for this fall to make it happen. Have list of contacts from craigs list that i've been posting to contact when I come up with a date and place at a motel close to my home town. September is usualy when I start shaving my body hair again thru spring being all my summer activities are over.

MY PLANS IN PROGRESS-will post movie and story after event.
I have around 30 guys on list and still adding letting them know ALMOST exactly what I'm looking for if we meet, I know only a few guys w... Continue»
Posted by sarahcd_legs 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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The Intimate Liaison
You would think being at home all day while the wife works would give me all the time in the world to indulge myself as Michaella but not so. Being a closet crossdresser with a f****y and home to look after is OK but a great number of friends and f****y call in knowing I’m at home and always good for a cup of coffee and a chat. Take this morning for instance my friend Steve phoned and warned me that he may be calling in on his way home from the town, but he did ask if I was busy. It is always good to see him, we go back a long way and even if I were busy I would always fi... Continue»
Posted by michaella_cd 3 years ago  |  Categories: Shemales  |  
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markie dunlap Kansas city sissy for all black Mast

I am a Sissy Faggot! I have been programed by hypnosis to write (beg) to be owned and femenized by a black Master in Kansas City Mo. For months I have watched repetedly sissy hypnoses videos and black cock worship videos. My girl freind set it all in play when she found me dressed in her panties bra and stockings. She has comanded me to tell all who read this that the phrase (black cock sissy) will in fact make me your sissy cock slave to dress me and use me as you wish. She has also instruced me to make it more intresting and let you know I live in Lees Summit and that Since I will not rememb... Continue»
Posted by markie2269 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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