Shemales Porn Stories
Page 119

How i became a girl

Hi my name is Mandy and this is my story..in parts. I started dressing when i was in my early teens. At first it was just panties, maybe pantyhose and masturbating with my friend B, but it soon became wearing skirts and heels, little tube tops and sexy dresses, then it was makeup and wigs, and soon we were both dressing up fully, doing our makeup and hair, and accesorizing with pocketbooks and jewelery.

We had suuuuccchh hot sex, kissing and fondling each others sexily clad bodies, our hands and lips and tounges roaming, licking, stroking and nibbling each other erogenous zones, before a ... Continue»
Posted by miniskirtmandy69 4 years ago  |  Categories: Shemales  |  
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Caught

This is how I got caught masturbating and lost my virginity to my stepmom.
I was still in High School but had just turned eighteen, and was still living with my dad and stepmom, Beverly. I was ashy kind in school and did not get many dates, this lead to lots of jacking off. I did not realize it at the time but not only had my dad married a transsexual, but Beverly liked to sl**p around. I later found out my dad, liked it and enjoy hearing her tell about a how she seduced strait guys.
So I was watching some porn on the internet when Beverly walked in on me. I quickly changed windows and made ... Continue»
Posted by raastible 3 years ago  |  Categories: Mature, Shemales, Taboo  |  
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The Bondage Whore, Chapter 10

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.


Chapter 10 - An Unwanted History Lesson


"Well, well, well... I do believe this just might be my worst student ever, little trouble-maker Rachel Wells."

"Oh no, Mr. Linebrink!" Rachel couldn't believe her horrible luck. Her old 6th grade US History teacher!

Mr. Linebrink stood there, with an ear to ear grin, looking straight down at Rachel's imprisoned face. "Yep, was I right! Wasn't I Rachel? You do remember that day in class, don't you? That day when I told you that you'd wind up a prostitute, or a stripper, or may... Continue»
Posted by thongcutoffs 4 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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I never thought I would

I was asked a Truth or Dare about my sexiest fuck. Well this is I guess one of the sexiest moments of my life as I never expected it to happen.

OK, there have been a few and my favourite changes with my mood. So one evening I was having a drink at my local. I was sitting next to a guy who was fun and we joked and laughed. As it got to closing time he asked me if we could perhaps go back to his place for a drink. There was no suggestion of anything odd, he was just an ordinary guy in an ordinary pub and I certainly didn't fancy him. Anyway we went back to his place, a small flat in town. He ... Continue»
Posted by uniqelyme57 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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Becommming Alanna - Part 4

There I was. On my knees. My lipstick smudged, my chin glazed, my belly full of semen. I didn’t know what to do. Mike just sat there and smoked, staring at me with his evil eyes… some time passed. I stayed on my knees. The silence was deafening but I was still loaded with d**gs and my spirit was limp, my will was flaccid. I fell from my knees onto the cold floor and just lay there. My face still only slightly glazed with the semen of the two 18 year old boys who had just ****d my mouth. My tongue was covered in a film, spit, ball sweat, and cum. My mouth tingled with the slightly electric tast... Continue»
Posted by KristyQuinn 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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SMALL GUY BIG SURPRISE!

It was Friday night and I had had a long week work sucked my boss is an asshole and I just wanted to go out and get laid! I got myself all dolled up brand new wig and it looked amazing with my hair flowing dark red it really brought out my green eyes I painted my all my nails ruby red and matched it with some glossy non smearing lipstick the expensive king that doesn't budge even if your sucking a huge cock and I was going to be baby if I had anything to say about it...My slinky red dress and matching fuck me pumps that were so high I needed to practice walking around a little to get my balan... Continue»
Posted by laceysgirl 6 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Paying for my own birthday present!

My wife told me that she'd arranged for us to spend a weekend in London, see a show and do a bit of shopping for my Birthday.

Great I thought.

We got to London, from Wales, early evening on the Friday. Checked into a quite nice hotel in the west end and headed up to our room. When we got up there, my wife headed for the bathroom and told me to come with her. Knowing what to expect, I stripped off and laid in the bath. She climbed in, pulled up her skirt, moved her g-string to one side and pissed straight into my mouth. We'd been in the car for about 5 hours, so what I got was stale and b... Continue»
Posted by garyw 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Fist visit to my sexy new female doctor

Yesterday I went to the doctor because i felt like i was peeing too much, i'm sitting in the waiting room and the doctor calls me, and she is the hottest woman i have ever seen. Late 20s/early 30s, gorgeous middle-eastern face, nice curvy lips, big dark eyes. She's very friendly with a thick Persian accent which i find very sexy. i explained to her my situation, and then she asked if i was sexually active, and i said no a bit too quickly, and she looked surprised for a second. She got me to pee in a jar, dipped the testing strip, and came over to show me the results. She got me to hold one end... Continue»
Posted by wet20 2 years ago  |  Categories: Sex Humor, Shemales  |  
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Wife and Sissy invited to a party

My wife and I were invited to some friends’ house on a beautiful estate in TX for a weekend party. While we were both well aware of the debauchery that could occur at the event, we had no idea how much participation we would both play. We were just getting off the plane to meet our driver when my wife handed me a slutty little maid outfit, and told me to go into the bathroom in the airport and change before we got out of the terminal. I did as she asked and then tried to walk out without anyone noticing but too many people in the airport to hide from as I only attracted more attention.

When... Continue»
Posted by moeclitty 8 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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Delilah and the Deep Blue Sea. (Part One.)



This story has taken me forty years to tell and I only finally relate it now in the firm conviction that nobody will believe a single word of it. In many respects that doesn’t concern me. I have other motives than those of persuading the reader of the veracity of my tale. I write it more to exorcise a ghost that has haunted me for most of my adult life and will doubtless continue to do so for the rest of my days. It is a story, the memory of which, has been my constant companion these past forty years and has dominated my life in the sense that everything I am today has been shaped by tho... Continue»
Posted by Mikebasil 3 years ago  |  Categories: BDSM, Lesbian Sex, Shemales  |  
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The girl inside me.

The Girl inside me...
I with my dolls outside the yard with Amber. What the fuck are you doing you little sissy? Screamed my daddy as he grabbed the doll out of hand and pulled me into the house. That day I learned what boys do and what girls do... but daddy I am a girl I said. Daddy looked at me just shook his head boys he said have dicks like this and girl have a pussy.
Daddy made sure I did all the manly thing like football working out...I had a killer body 6 foot 1in... I was totally ripped. My cock was above 10in and 3 in thick the girls loved it. Every girl in my high school had rode ... Continue»
Posted by mykitty08 3 years ago  |  Categories: First Time, Shemales, Taboo  |  
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First time hooking up with a shemale

Well the first time I hooked up with a shemale was an e****t visit (night out, massage and the rest :)), this was when I just started to gain interest in shemales (about 2 years ago), so I became curious and wanted to know what it was like to spend a night with one, after all they say its having the best of both worlds. I looked up a Brazilian shemale online and when I saw the pictures, I couldn't resist a visit. I mean her femininity was beyond this world, stunning from head to toe. I gave the e****t a call and asked to see if she was available for night out and it must have been my lucky day... Continue»
Posted by mensah9 4 months ago  |  Categories: Fetish, First Time, Shemales  |  
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Working late

This story follows on from my last story “On the Road”

Working Late.

Dannielle had been woken by a call from Paul asking her to come into work early as they had some figures to go over. She knew what that meant, a quick fuck before work. As she was getting ready she remembered what those builders had said yesterday, the photos they had taken and the note they had left. “Wonder if they where actually going to come to her work and find her if she did’t get in touch” she thought as she got ready. It wouldn’t be that bad, she had fun with them and she loved Johns cock. “Bet they where just p... Continue»
Posted by danni1 5 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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olderman and mature crossdresser part 1

It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all.
As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a couple bending over shots and eye contact.I made my way to the check out an seen him in other line.I finshed checking out when I got outside to load my bags in my car he was parked next to me.He spoke to me and said that he was sorry for following me around that he was not some kind of crazy killer but ... Continue»
Posted by cdpaula 3 years ago  |  Categories: Gay Male, Mature, Shemales  |  
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Becoming the girl i really am....

I guess I'll start from the beginning, I was in my early teens and my parents had friends in town who we did everything with, travelling, camping, holidays, the works. They had a daughter who was a couple years older, and a son who was my age who was pretty much my best friend.

We started masturbating together in our very early teens, and since we were such good friends we were together a lot. One night i was sl**ping ove rhis house and while we were masturbating he asked "have you ever gotten a blow job?" "No" i said, giggling nervously as he slid right up against me in bedand slowly r... Continue»
Posted by dirtygurl4u 4 years ago  |  Categories: First Time, Shemales  |  
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The dream

I just finished my shower and stepped in to my bedroom wearing nothing but my boxers. I felt something behind me and turned to find a red headed goddess walking in to my bedroom. I’d never seen this beauty before and had no idea who she was, but she slowly walked toward me, wearing this black silky long dress, her nipples visibly poking through the fabric. Even though confused at who this was and what was happening, my male responses kicked in and I immediately started getting hard. She noticed the rising bulge in my boxers as she got so close to me that the front of her body was touching mine... Continue»
Posted by Wargods 3 years ago  |  Categories: Anal, Fetish, Shemales  |  
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sissy lola gets a treat1

Last night was my first night as a sissy maid for my beautiful goddess maureen and i have been instructed to tell you what a dirty little cock sucking whore i have been.

I have known goddess maureen for a while now, she has been giving me instructions via webcam. She would make me flog myself or fuck my ass with a huge black dildo untill she was amused. So last night, i received a set of instructions telling me that i must prepare for a very special night. I was to lock my cock in a chasity device a week before. I then had to post the key through goddess maureens door. She said i had to get... Continue»
Posted by sissy_bitch 4 years ago  |  Categories: BDSM, Gay Male, Shemales  |  
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bad gurl in town

I love business trips. New towns are so exciting. Whenever I enter a new town I check online to see where the local cruising spots are. This time it was in Vancouver, BC Canada.

Vancouver is a wonderful city with an active GLBT community. If you have never been there I highly recommend it.

Now I look pretty andro so I generally don't have a problem as a man or a woman. Tonight I was putting on my favorite skirt and cruising the town.

I went to the hottest gay night club but there was a huge lineup. Damn, I thought, no luck there. I decided to walk down the street a bit further and... Continue»
Posted by zaria_ts 2 years ago  |  Categories: First Time, Shemales  |  
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blew him away

recently i met a frustrated 32 year old married man who was not getting sex from his older wife,he told me he was straight. I met him in holiday inn in town,i arrived in reception and met him.My hair was very long,i had lots of make up on,was wearing 8 inch black heels,black stockings,suspenders,g string,black bra,body jewellry,belly button stud,on top i was wearing a red tight dress,my nails were painted,had thick red lipstick.

He gave me a kiss and said i looked beautiful and i followed him too his room, i look embarassed as everyone looked at me,i felt like a prostitute becasue of the wa... Continue»
Posted by ladyboyslut 3 years ago  |  Categories: Anal, Shemales  |  
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sissy caught by daddy

I was so scared ,Dad had caught me several times dressed up in my s****rs clothes but the last time he told me that the next time he caught me the punishment would make me never disobey him ever again,and that was less than a week ago.Now here I sit on the foot of my bed wearring my s****rs satin lace panties and bra,her stockings,heels and her favorite slutty skirt and top.I had skipped school just so I could dress up and had just finished putting on my lipstick when dad walked in and caught me.He laughed and told me that the school called him because they didnt believe the lame story I told ... Continue»
Posted by sparkyking 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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