Shemales Porn Stories
Page 74

Caught in the act

After my first encounter with John’s dick, I couldn’t get it out of my mind. Two weeks later we met at a friend’s party and we talked about it. He was worried his girl friend might find out. I told him he had noting to worry about as I had as much to lose as he had. But I also said it was the best sex I ever had & wanted a repeat performance. He agreed it was fun but felt to do it again would be risky. I said all we needed was an excuse to go away for the weekend. I told him to leave it to me.

I happen to mention to his girlfriend later that John & I were thinking of going away to see a ba... Continue»
Posted by monkeynuts0 4 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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My CD friend

This story is fiction.

~~~~~~~~~~~~~~~~~~~~~~~

I had been chatting to people on a ts chat room as I had recently become accustomed to do, when I received a private message from a local cross dresser. She asked me where I was from, how old I was etc and we found out we lived a few towns away from each other, both young guys and both really loved wearing women's clothes.

Admittedly she was much more experienced at it than me, having access to girlfriends, s****rs and mothers clothes and had even ventured out fully dressed once!

Eventually after some light chat, swapping dressing up s... Continue»
Posted by shyadam89 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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My New Whore

Disclaimer: All characters portrayed are over the age of 18. Any similarities between persons living or dead is entirely coincidental and unintentional. These characters are entirely of my own creation, and thus don't belong to you. Don't use them or this story for your own purposes. There's a reason they belong to me.

Justin's body trembled, as he sat in his chair, his eyes glued to the floor. It was obvious from his reaction that he hadn't expected me, or anybody for that matter, to walk into his apartment that night. We had been friends for several years now, and though it ... Continue»
Posted by BigStevieAwesome 4 years ago  |  Categories: Anal, 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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The wrong bus, Part 2

This is part two of the story. Please remember I did not write this story I love it so much that I want to post it and share it with the rest of you. If you want to show some appreciation please give it to the original author her email is at the bottom of the story.

The wrong bus, Part 2
By Sissy Trisha

I woke up with my alarm ringing in my ear and jumped out of bed realizing
I was still wearing my bra and panties from yesterday. Suddenly the
entire day flashed back in my head, being caught by Master Harold and
blackmailed into being his sissy slut at his house. The humi... Continue»
Posted by curiouscuck 4 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
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My first time with a shemale(True Story)

This is a true story about my first experience with a shemale.

I was sitting around the house the other day horny as fuck. My usual girl that i call on when i get that way had f****y in town for christmas so she couldn't meet me. So i decided that i would look on craigslist and see if i couldn't find someone that wanted to fuck as much as i did. As i was looking through the ads and as usual not finding any women that were real on there i clicked on the T4M section. I had always been a bit curious about being with a shemale and decided that i would respond to a couple of the ads. The fir... Continue»
Posted by wild_wolf_03 6 months ago  |  Categories: Anal, First Time, Shemales  |  
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Chatroom tricks part2

Mary got up and left the room, closing the door behind her. Well it was supposed to be a midday call, have sex and go home, but as my tied body looked out of the window I saw night drawing in. Then to my horror car headlights reflecting into the room, someone had just pulled up on the driveway and I remembered Mary was married…

What the hell was I going to do? Mary had always been honest with me and I knew what I was getting into, I don’t know what this man, her husband was like but what the hell would he think of. Here lay on his marital bed was a young guy, probably young enough to be his... Continue»
Posted by stig1963 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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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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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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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 2 years ago  |  Categories: Fetish, Group Sex, 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
adventurous.

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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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 2 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 4 years ago  |  Categories: Mature, 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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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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"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 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Beginnings

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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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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"Call Me" (a Chrissie Conway story)

"Call Me" (a Chrissie Conway story)

Shortly after I'd finished college I had a job with an import-export business whose main office was located
near the cultural center. This area of the city was home to a small arts college, a large public library, several bookstores
a small upscale hotel and a couple museums. I often spent my lunch hour in the tea room of the art museum. The tea room
was actually an open air courtyard located in the center of the museum building. Besides providing a peaceful setting
where you could enjoy a light lunch, the place always seemed to be a good place for... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Shemales  |  
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