Shemales Porn Stories
Page 66

My first blowjob (sirky)

I started crossdressing when I was in high school. Small things that I had found or stolen: stocking, make up, thongs... I loved to look sexy, but I didn't feel gay at all. In high school I met a boy some years older than me. He was a great friend, we used to go to his house to play videogames since I didn't have a console.

One day he started dating a girl, and we started to talk about porn and sex (I was virgin, so I was really interested in that topic). We eventually ended watching some porn. I had some magazines, but no videos, so it was awesome to go to his house, play for a while with... Continue»
Posted by sirky 11 months ago  |  Categories: Gay Male, First Time, Shemales  |  
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Who is seducing who?

One of my main fantasies involves me seducing a girl in public... in a cafe for example! I've only just met you & you are so glamorous I am absolutely captivated! We are in a 50's style diner & it's really busy but we have a table in one of those booths. We;ve ordered our food & are chatting easily all the while flirting uncontiolably,
We're sat opposite eachother at the small table & your stocking clad leg accidently brushes against mine I can feel the silkiness even through my jeans. You apologise & I tell you thats absolutely fine & I reach my hand under the table & touch you kneee.. A sm... Continue»
Posted by chrisluvsgirls 11 months ago  |  Categories: Masturbation, Mature, Shemales  |  
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helpless



Helpless[/b

He coluld do nothing to escape the lip gloss brush across his lips as he
had just started the engine to the car and done up his seat belt when she
reached over and applied it to his lips. He had thought she was going to
put it on her own lips and was caught by surprise by her sudden act.

She told him, "Pucker up your lips like you see other women do."

Having just had lip gloss put on his lips against his will why did he
obey this direct instruction? He could have refused as he wasn't a woman
was he? He felt the sticky feeling on his lips of the lip gloss she
... Continue»
Posted by klammer 11 months ago  |  Categories: Shemales  |  
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The Slithering: The Cloak and the Dagger

The Slithering: The Cloak and the Dagger



The young boy quickly wiped the large amount of sweat from his brow,
finding it very difficult to withstand the unbearable heat of the dingy
workshop as he placed the fiery, malleable blade against the flat
surface of the blacksmith's anvil. The thick, black smoke choked his
lungs and he gagged a bit while trying to maintain his composure.
Grabbing his small hammer with his left hand, the boy raised it upwards
and then f***efully brought it down against the blade with a loud
strike, as bits of heated metal spewed forth. This was a ... Continue»
Posted by klammer 11 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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cant help falling for hot sexy times with married

When i was younger i never got the pretty girls and never functioned down below well and soon became transgendered. I dont have the pressure to perform any more . I was still attracted to girls but one day saw a huge black man with 2 sexy girls and i began to wonder why so many females had black boyfriends. All of my female relationships ended with the girls going to black men so got intrigued.
One day i was out one night in Manchester and was asked by a very tall black man if he would be able to lick and kiss my feet. Instantly i thought that would be lovely. I didnt expect to see his m... Continue»
Posted by Jennifertaylor 11 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Locked In Chastity – Sissy

“Oh, dear, baby! This won’t do at all. Another two months it is!” Amelia chirped as she gazed upon her helpless husband, “You know the rules!”

John was fully aware that being caught with his hand on his straining little sissy clitty, desperately trying to stroke it through its cage for the third time, meant that his period of enf***ed chastity would now last six months. In the brief, thrilling moment of his quickening heartbeat forcing bl**d into his face, John remembered the first day he had been locked up by Amelia, and a shiver ran up his spine. They had been happily married for nearly f... Continue»
Posted by JSissy206 11 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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Sissies New Years Surprise – Part 1 –

“sissy come in here, W/we need to talk.”

“Yes Mistress, coming.”

Sissy enters the room and curtseys, with sissy’s eyes downcast she sees Mistresses finger pointing towards the floor. Sissy hobbles over to Mistress and kneels at Her feet. Today, Mistress has sissy in her black satin maids uniform with pink lace trim and a pink apron. Sissy also has on a matching pink hair bow, pink petticoat, matching pink ruffled panties, black hose with matching garter, a black bra, and black 4’’ locking pumps. This morning at breakfast Mistress had told sissy that today sissy was to clean the house ... Continue»
Posted by JSissy206 11 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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Sissies New Years Surprise – Part 2 –

Chapter 2

Sissies Opportunity Blown

Sissy was dead tired. It had been a long and tiring day. Mistress was very picky today at inspection and sissy had to redo some of her work several times. Sissy would admit that some of her work was sloppy, but sissy could not concentrate. Mistress had just told her the biggest news and she still couldn’t wrap her head around it; no wonder her work was messy. As a result sissy had to spend an hour in the corner tonight and was sent right to bed following her chores and Mistresses dinner. Yet as tired as sissy was and as much as her feet ached she ... Continue»
Posted by JSissy206 11 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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Sissies New Years Surprise – Part 3 –

Chapter 3

The Decision

Sissy got out of bed at her usual time and went about her morning routine of shaving, showering, and getting dressed. Sissy thought maybe she got an hour of restless sl**p. After not being able to perform last night she had pretty much laid in bed all night crying and pondering how she became to be such a sissy. To her own surprise she didn’t put much thought into what decision she would make b/c deep down she knew the answer already. If she couldn’t perform with her current girlfriend how would she ever be able to perform with another Woman, after all Mistr... Continue»
Posted by JSissy206 11 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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CHAPTER FIVE

CHAPTER FIVE
One really bad thing about a last minute airline reservation is that you take what you can get. This meant a six hour layover on the way home. I got in at 9:30 local time. I claimed my two empty suitcases and retrieved my car from the parking garage.
Once on the road I drove to my townhouse with the moon roof open. I felt good to be in my own car again, the smell of leather instead of plastic, my body held snuggly by the bucket seat, the sound of the wind rushing over the open space above my head. I cranked up the stereo’s volume in order to compete with the wind noise. It was ... Continue»
Posted by justluvtrans 11 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
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nylondaddy

I went through forty-five years of my life as a single man, no one to answer to but myself. I watched my friends marry, have c***dren, and get divorced. I kept hearing the same old stories, 'money problems', 'she wasn't the same in bed after the k**s came', 'we are too tired because of the k**s', and the best of all 'we fight too much over money and the k**s'. I would just listen and laugh in my head at them. Then I met ellen. Ellenwas just your average sized woman on the outside, size 12 full figured, but she carried it well. It was her big boned body frame rather than just added weight. She ... Continue»
Posted by satinexinhose 11 months ago  |  Categories: Anal, Fetish, Shemales  |  
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Sarah Collaring Julie

Sarah: *slides her hand under your shirt*

Julie: *Guides your hand up to the middle of her chest then scrunches her shoulders, gently squeezing your hand between her tits*

Sarah: *Gently squeezes at your breast as your soft mounds press around her hand. Slowly pushing her thigh up under yours, making your leg lift up around her hip*

Julie: *Moves over top of you, sliding up onto your lap, quietly purring as she looks down, watching your hand between her tits*

Sarah: *Purring up at you quietly, moving her other hand up under your shirt, both cupping your mounds now, squeezing them s... Continue»
Posted by noin007 11 months ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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On the side.

Being in chastity constantly starts to make me extremely horny. After several days of being alone I just couldn't help myself. A dildo wasn't going to do it. Due to the kind of parties we have had I knew there was a gay couple down the street. I was dressed as a French maid when I first met them. Chris was the younger one, my age. Mark was a little older, they were slim and in good shape. Chris was a little taller and more blonde. Mark commented on my outfit, heels, stockings, chastity cage, short skirt and bottom of my ass hanging out.

Since then, they have always invited me to come 'dirty... Continue»
Posted by bisubtaylor92 11 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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The college fantasy part 1 (Futanari)

As a junior in college I was overwhelmingly lucky to have a girlfriend that was a freak in bed. Her brown hair cascaded down over her D cup tits that would bounce beautifully whenever we fucked. The only description of our sex life that even came close to describing reality was a porn movie. By the time we had been dating several months I had learned many of her kinks. She loved being tied up, even having her tits slapped. There was no limit to the degrading names I could call her or where I could blast my load whenever we were fucking. Over the span of the whole time we knew one another... Continue»
Posted by fictiong 11 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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Fucked by a ladyboy

A couple of months a had sex with a ladyboy for the first time. I met her on the internet, after chatting for a couple of weeks she was visiting my country for vacation (she's from Thailand).

We met in Amsterdam on a sunny afternoom. After walking through the city and showing her the touristical highlights, I asked her if she would like to come to my house. She agreed. On the way to my house we were holding hands constantly, and in the bus she rested her head on my shoulder. At my house we started kissing en making out. Then she asked my if I wanted to go to the bedroom. I showed her the wa... Continue»
Posted by gogolo999 11 months ago  |  Categories: Anal, Shemales  |  
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Feminized by My Father

I opened my eyes, blinked, yawned, closed them again.

I felt confused, disoriented in a way that was... strange. It wasn't like waking up was supposed to be, I wasn't half asl**p. I can't remember getting in the bed, in fact I can't remember the last thing I remember. Where did consciousness end last? I was clueless.

I tired to move my body and I found it difficult. I could move though, I rolled over onto my stomach and opened my eyes, I was on the guest bed in the basement. Blinking didn't clear the fuzz from the world, so I went ahead and tried to get out of bed. As I stood I felt an i... Continue»
Posted by AssLover1992 11 months ago  |  Categories: Shemales  |  
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MY first time with a TS

Actually it was not intended that I should visit Fransheska.

I had in fact been looking at Iris Baby... her profile I had seen on e****t Guide a few weeks ago. When I finally decided me and got it all in place, it turned out that Iris was not in the country. But then (the other day) she showed up here on the wiki.

And THEN finally I got a dial tone! But after three calls without answer I stood there with my 1,500 burning in the pocket - and a bulge in my pants - and still no deal. Now what?

Got my mobile out of the pocket and then scrolled down... Fransheska... the two Tayras... Lore... Continue»
Posted by mazis2003 11 months ago  |  Categories: Anal, First Time, Shemales  |  
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A tribute to Joy

I had always loved women’s clothing. Well truth be told, I had always wanted to wear women’s clothing. I envied women’s ability to change their look with just a little effort, a tight skirt; that was so sexy in one way to a pair of jeans that was sexy in an entirely different way. Then there was the hair thing. I thought that it was so cool the way that women could change their entire look, even their personality by just wearing their hair differently. I really like women. If it wasn’t for that monthly thing I would want to be a woman. I would be a lesbian if I had my final sexual preference. ... Continue»
Posted by justluvtrans 11 months ago  |  Categories: Anal, First Time, Shemales  |  
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Becoming sissy Jenny Part one

Hi, my name is Jonas and I´m 25 years old. This is the Story of how I became a sissy. So actually my name is Jenny now. But lets not get ahead of ourselves. The story has a slow build up, I hope it´s interesting for someone. Thats part one, I will continue the story from time to time. Everything sexual in this story happens to people over the age of 18.

I guess it all started whit my mom being a gold digger. One of those women who have a pretty face and a nice body and try to make a living out of it. After a few years of being an e****t, getting to know people, sucking the right dicks, gett... Continue»
Posted by jenny42 11 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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Trip to the mall

So here I was again on a trip the the local mall. My wife the finest shopper of them all was in need of some new makeup, so the good guy i am decided to open my wallet and take her. (NOW before we go any further, I am a closet shemale and now even crossdresser fan for years) So upon arriving at the mall weake our usual rounds and eventually stop at her favorite chain makeup store, yes I've been there before. Today though as my wife was doing her thing with a female sales person, I noticed a very interesting young lad working. Now there is always what considered the "gay guy" working in these ... Continue»
Posted by Fnumo38 11 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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