Shemales Porn Stories
Page 66

''What's a man to do''...

After a long week in work I didn't really feel like going to the party we'd been invited to.
My wife said ''We have to go and you never know who might be there''.
I agreed reluctantly and showered and changed and we headed off to the party.

Now at this stage I must tell you these are no ordinary parties we attend. We're part of a group of people that like to play. Yes it involves swapping and doing kinky things with other naked people.

We arrived a bit late and so some of the guests had already shed their some of their clothing.
A few topless women sipping wine with men with bulges ... Continue»
Posted by guru6969 3 months ago  |  Categories: Anal, Fetish, Shemales  |  
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Helping a gurl out

Just to explain a few things, we live on an island in the irish sea between Britain and Ireland. T-gurls are rarely heard from, nevermind seen for fear of negative comments.

Vikki was a t-gurl that my wife (K)and i met via a swinging site and had played with on a number of occasions. She would visit the island with work and when done for the day would indulge in meeting anyone who wanted to fuck her.

Vikki arrived on the island on the Wed and we met her on the Saturday. As this was our 3rd meet with her we had all got quite familiar with each other and enjoyed a very sexy evening togethe... Continue»
Posted by ManxTightslovers 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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My Parents Had Gone Away on Vacation

My parents had gone away on vacation for a week. I was thrilled!

On my own for a whole week, free to do whatever I liked. And truth be told, what I liked was being nude, as well as dressing in women’s clothes. The first day they were away, I began enjoying my newfound freedom.

I am very slight of build, feminine really. My body is hairless save for in my crotch.

After dinner, I decided I wanted to enjoy myself nude. I turned off all the bright lights in the house, and left on a few lights that were dim. All the blinds in the house were open. I stripped off all my clothes and walke... Continue»
Posted by ssup28 3 months ago  |  Categories: Shemales, Voyeur  |  
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My Fucking f****y 2

My s****r had just come out of the closet with a handful of clothes and told me to take off the swimsuit. She laid out a pair of white cotton panties with cherries on them and a matching bra. A short pleated plaid skirt and a white button down shirt. She also laid out some white thigh high stockings and some black Mary Jane platform shoes. She said this one was mine.

She laid out a nearly identical one except that her plaid skirt was green whereas mine was red. She told me to get dressed but that she would help me with the stockings. "You know I have always wanted another s****r. "Someone t... Continue»
Posted by 6270daniel 3 months ago  |  Categories: Anal, Shemales, Taboo  |  
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Pai-chan’s long walk home

School-gurl Pai-chan took the short-cut home from school, through the Sakura sweet smelling woods one Friday after class. The trail went past an old hut and as she approached it, a masked man jumped out from behind her, grabbed her by the arms and slipping a ball-gag into her mouth, d**g the sexy gurl into the hut.

There was a dirty, stained mat in the hut and her a*****or threw Pai-chan onto it. He lit a cigarette, his eyes glinting through the mask as he watched her struggle uselessly against the bonds.

“No... Continue»
Posted by tuckpussypeachpie 3 months ago  |  Categories: Fetish, First Time, Shemales  |  
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Deflowered at 17...Part 1 (ENGLISH VERSION)

Many friends, some of them curious and excited by my (recently discovered) Polaroid pictures made at the seaside (with stockings) when I was 17 years old, asked me to tell the story associated to them. Someone also pointed out, "but if in one of your stories you talk about your first man -see story “my first man”- after having been “initiated” by a trans, then who was actually your first man? "
First of all, let me say that I can assure you that my stories are not fancy, they are absolutely true. I can change some details, names, situations, ... but I do not not invent anything. Anyone who... Continue»
Posted by AngelicaTrav 3 months ago  |  Categories: Fetish, First Time, Shemales  |  
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Jake and sexy Tgirl Amanda were next on our "

So after we went out with Pete and Becky all day
Jet Ski's, Diving, and sneaking off for some impromptu blowjobs or a quicky, Alex and I decided that we'd ask Pete and Becky if they'd mind if we brought Jake and Amanda into our group. We described them to them, and they were hooked.

That evening at dinner Alex took it upon herself to make the first move. She sent over some drinks, and they came over to our table and that's where this story begins.


Amanda asked if we were swingers, when I spoke up and told her that even better than that, we're all bi swingers. Her jaw dropped and he... Continue»
Posted by SpicySide69 3 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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Male to female transgender. Had no idea!

This is a true story. This was a time in my life where I was sort of a bitter person. This story is geared more about the things that led up to my encounter. This was a result of a series of events led up to this point in my life. Let's begin with the basics. I was in the military. I enlisted because I had one full time job and two part time jobs and still had trouble making ends meet. I was seriously overworked and my wife refused to get a job. So logically, I weighed out my options and decided to enlist into the military. It would be one full time job with a slew of benefits. Once I graduate... Continue»
Posted by fortworthfitness 3 months ago  |  Categories: Anal, Shemales, Taboo  |  
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Vicky's Pink Diary 03

So here I am waiting for my Uncle to come home for his tea, wearing Donna's knickers! Vicky's wardrobe is quite sparse, due to having just one locked suitcase hidden under my bed. I'm lucky that my stepmother is roughly the same size as me, and a total slut! Probably the only thing I like about Jenny is her clothes, she dresses like a girl half her age, and I know for a fact she shags around. I know my friend Sean has had a few narrow escapes from my stepmother. Then one day when I ask him about the way they smile at each other, he owned up. So I now know that they have fucked, I finally got i... Continue»
Posted by sparkyking 3 months ago  |  Categories: Gay Male, Shemales, Taboo  |  
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Vicky's Pink Diary 04

My head is spinning now, and as my uncle slowly pulls my panties down, I close my eyes dreading my fate!

I watch as he pulls my case out from under the bed. He takes a key out of his trouser pocket and unlocks the padlock.

"My god, how long have you had a key?!"

"Vicky, surely you remember losing a key a little while ago. It fell out of your jeans when your stepmother pulled them out of the washing machine. She didn't notice, but I did. Now I don't want to bring the other you up, but I did wonder why you would have a key in your jeans."

I knew I'd lost one of the keys, but I ne... Continue»
Posted by sparkyking 3 months ago  |  Categories: Gay Male, Shemales, Taboo  |  
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Old man fantasy

I have always been aroused by horny old men,I always wanted to be exploited by a group of old horny men until one day when i got this job that required me to take care of a 66 y.o gentleman.
He seemed so nice and since it has been my passion to serve other men i accepted the job without thinking twice.Things went well and we got along just fine..he was really funny and we became close friends very fast.
One day he called me and told me that he must speak with me face to face so that he can share a problem that he had for years with me,I rushed over to his place worried that something may hav... Continue»
Posted by cutecdkiss 3 months ago  |  Categories: First Time, Mature, Shemales  |  
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The last time I was a slut for cock

This is an account from my diary about the last time that I was a total slut for cock, before I realised that there was power in being dominant.

Went over to see Peter yesterday, it was about 8pm when I left his house but I didn’t have to worry about rushing home.
It was nice being with Peter again, he’s taught me so much the past year and he loves me in feminine clothes but he wouldn’t let me take the dress that I’d worn for him home. He let me go home wearing the bra, pants, stockings and suspenders though, it felt lovely wearing them when riding my bike. I felt so happy having spent th... Continue»
Posted by angelatvdom 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Gary's Dressup Sissy

When I was a teenager I lived next door to a guy named Gary. We were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls I didn’t see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games.

One day we were watching a movie, when Gary suggested watching some of his dad’s pornos. I eagerly said yes. So for a few days we would watch porno from about 10 am till 4 pm when his mom came home. His dad seemed to have hundreds of movies. One mov... Continue»
Posted by palmorr 3 months ago  |  Categories: Anal, First Time, Shemales  |  
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Caught and made into a sissy slut

It was for real this time. No fantasy. Reality. I was dressed up in red: fishnet stockings, g-string, and a babydoll. I was wearing a metal chastity cage that was pulling my clit down, and it was a clit, it only half filled the cage. I had a new cock too - a black face dildo which was double-ended. In my new role, I had to jerk it as I was fucked in my pussy and I was being fucked. She had fucked me so hard that I was completely submissive to her, sucking on my gag with wild abandon, a true sissy slut.

It had started earlier that day when I had been caught jerking off to a mixture of cuck... Continue»
Posted by andygone 2 months ago  |  Categories: Anal, Fetish, Shemales  |  
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The Lady Inside by loyalsock

I looked at the sinuous curves of her body. The long legs, the curling hair. She was built like my fantasy, every inch of her in pale ivory and inky black. Her pumps hugged the delicate curve of her feet—the arch and the heel. Her dress matched in deep crimson and swung light and silky around her narrow hips and broad back. I stared, unsure if what I was seeing was real or just Hollywood smoke and mirrors. When she turned to me and smiled—lovely white teeth glistening behind her red, red lips—I almost fell backward. I was beginning to think she was a mirage brought on by the heat of the Mexica... Continue»
Posted by loyalsock 2 months ago  |  Categories: Anal, First Time, Shemales  |  
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Nothing Else Matters 1 by loyalsock

About a week had passed since the incident with Casey coming by my work place, trying to blackmail me, by telling my friends I was dating a transsexual. I had talked with Christina about the whole situation, and she had been able to calm me down and help me relax. I had been so pissed off at first, that I couldn't even think clearly at the time. But with Christina's help, I was now seeing things a little more clearly than before, and I had even come to a decision of how I thought I could solve the problem without being f***ed to sl**p with Casey as she was demanding.

I would let everyone I... Continue»
Posted by loyalsock 2 months ago  |  Categories: Anal, Hardcore, Shemales  |  
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Becoming his girl (Sissy story by GirlyGay)

In the summer after my eighteenth birthday, I met Nick. He was a thirty-something who lived in our building. My parents had gone for their yearly European trip, and I had been left behind this year because I had college orientation during what would have been the last week of their trip.

Mooning and alone, with nothing to do for four whole weeks until my flight up west, I took to the pool to catch some sun. I had not bought new trunks in a while, and so my old ones were riding high on my legs.

Nick was already at pool, beer in hand, sitting back in a barca-lounger. His broad, smooth che... Continue»
Posted by sissyAlyna 2 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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The Rendezvous Pt1 (Sissy Story by CassidyCaine)

Nick looked at the email he'd received from his wife at lunch again as he got ready to leave work. It had been a month since he'd confessed to her his love of dressing up in women's clothing after he'd kept it hidden since they first met. But, Nikki was insistent so he had tried to share that part of him. She had worried he was gay or didn't want her anymore but he'd assured her that wasn't the case. Yet after all that worry, she had emailed him to tell him that tonight she wanted to play with his fantasy and role play a little to see if she could get into it. She had rented a motel room and w... Continue»
Posted by sissyAlyna 2 months ago  |  Categories: Fetish, Shemales, Taboo  |  
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A Night at the Metro

Before the inevitability of gentrification set in, Toronto's Metro Theatre stood for many years as the city's last full-screen porn cinema. And while more recent innovations in pornography (such as home video and later, the internet) had taken their toll, the Metro had things to offer which could not be had elsewhere. Living on the other side of town, I was an infrequent visitor to this one-time temple to sleazy entertainment, but on the occasions that I did, I'd usually have myself a good time. This story is about one such occasion.

Exiting the subway at Christie station, I could feel the ... Continue»
Posted by sissymaidjanine 2 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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A young man's summer [full story]

MY BEGINNING

My name is Jason, and I am a typical teenaged young man; lean, horny all the time and really happy that I have reached the age where I can get a job that pays better than mowing lawns or delivering papers. My parents work all the time and me and my older b*****r John, have had the house to ourselves since I was 8 and he was 13, which meant no more getting up at 5:30 to go to a sitter who would either keep us all day or make sure we got on the bus for school.

I discovered the concept of sex early on; John would jerk off constantly if he thought no one was watching, this sta... Continue»
Posted by serious58 2 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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