Shemales Porn Stories
Page 70

My first time

This is a true account of my first time with another man.
Cruising the craigslist personals had become a common practice for me when I was bored or feeling horny. At first it was just reading ads until I got so turned on that I had to masturbate; but then it turned into actually replying to posts. Around the same time, I had become curious about wearing panties. One night when I was feeling especially horny, I tried on a pair of panties that a girl had left under my bed after a late night hook up. I fell in love with the feeling and began placing my own ads to chat with men that liked guys i... Continue»
Posted by igotoneforya 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
  |  4

The Ghetto bitch

-The Guys

4 ghetto guys was inside a porn site looking at random sissy babe pictures when they accidently found a picture of someone they know. Like every album they clicked it that specific one with a tranny dressed so girly with mouth open. The guys had such a stone hard erection by watching all the pictures, they even said "I Would bang that sissy pussy 4 sure!" and everybody agreed. It was that guy from elementary school named L****. They started to chat with him, pretending to be the perfect guy to take care of his sissy needs. After 2weeks they made this sissy want to meet eachother, ... Continue»
Posted by sissyVenessa 1 month ago  |  Categories: Shemales  |  
  |  2

Tricked by a shemale

I was out with a couple of guys from work, Brian and Dave, and we were having some drinks at a local bar. I'd never been out with them before, but they invited me and I didn't want to be rude.

While we were having our drinks I had made some negative comments about gay men at one point, you know how it is, right? Just trying to make some conversation, but they hadn't said anything back, negative or positive, but they did exchange a look that I didn't think about until later... much later.

Brian ordered us another round and I excused myself to take a leak. All I remember after that was ... Continue»
Posted by kevinj631 1 month ago  |  Categories: BDSM, Gay Male, Shemales  |  
  |  10

There Are No Limits, part one.

*This story is a work of short(ish) fiction, and despite the tribute that I would like to pay to the real people these are based off of, their names have been changed. Chicagoland area residents will recognize some of the places despite the name changes.*

Part 1:

Sheridan and I have been partners at the Wesley Avenue Police District for something like six years. We're part of a larger group of six: Me, Bonds, Martinez, Sheridan, Maurice (the only one who uses his first name) and Woodard. Officially, we're known as the patrolmen on the night shift in Lakeview, but the brass calls us the... Continue»
Posted by asphalt3 1 month ago  |  Categories: Anal, Shemales, Taboo  |  
  |  2

Tranny Dogging Experience

Not my story as i'm a proper woman lol but i just loved reading this...................

I am a 24 year old male to female transsexual, I have been dressing up as a a woman since I was 14 and had nylon led sexual fun since my early teens. Often wanking myself whilst wearing a pair of sheer stockings. The result is that today I have a very large wardrobe of clothes and shoes, I am completely smooth all over apart from a landing strip and have manicured nails and shaped eyebrows and with killer legs in high heels. I am single but I had this strong desire to go dogging. I fantasized about being... Continue»
Posted by celtic-green 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
  |  2

Poker Night Part 7

A continuation of my story. Parts 1-6 can be found on my profile page. Thank you and Enjoy!

Morning of Halloween Day was uneventful. Daddy prepared breakfast for the two of us and Mistress Claire had come by as well to join us. "Are you excited for tonight?" she asked. I said "Oh yes Mommy I can't wait to get candy!" She giggled a little and said I looked so cute and adorable and continued eating her breakfast. Daddy placed a couple pankcakes on my plate and then I noticed his rock hard cock was fully erect, he was stroking it with one hand and patting my head with the other. "Would my baby... Continue»
Posted by ConvertedGirl914 1 month ago  |  Categories: Group Sex, Shemales  |  
  |  1

Chapter 5 Derek Enjoys Chrissie to the Fullest

Chapter 5
Derek Enjoys Chrissie to the Fullest

I gathered up my clothes and shoes and silently went in search of the
bathroom to freshen up, as I was ordered to do by my wife's best friend
and my doctor, Helen. I couldn't quite believe I had just given head to
Derek, who I had only met less than an hour ago and who I suspected was
less than a reputable figure although I had to acknowledge he had a cock
worthy of worship. It was the first time I had done that in my life and I
found the experience both humiliating and deeply erotic. Truth to be
told, the humiliation factor weighed l... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  1

Chapter 6 Mommy Returns

Chapter 6
Mommy Returns

So much had happened in the last few days. My wife's best friend had
confided in me that my wife of five years, Heidi, was three months
pregnant with her lover's baby and was planning on serving me with
divorce papers when she returns from holiday next week. That same woman,
who just happened to be my doctor and was the person who had administered
my three year course of oestrogen treatment, had now declared her
interest in me, not so much as a prospective spouse but as a benevolent
owner who was soon to reap the coming rewards from my upcoming career. In
... Continue»
Posted by klammer 1 month ago  |  Categories: Fetish, Shemales  |  

Chapter 7 Chrissie Recovers

Chapter 7
Chrissie Recovers

I couldn't really move off the sofa for the next few days as the recovery
from the breast implant surgery required me to sl**p in a sitting
position so mommy laid a sheet on the sofa and propped pillows behind me
and for the next four days I just wore a satin dressing gown and kept my
movement to a minimum. My new breasts ached and I was too scared to even
look at them. Mother was used to me taking care of her every whim so,
when the tables were turned, she tried to be the best 'Nurse Nancy' she
could but her wonderfully wicked nature wouldn't allow her... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  

Chapter 8 Chrissie Learns to Serve

Chapter 8
Chrissie Learns to Serve

The weekend was a blur as the overdose of hormones rushed through my
body. The nurse in the clinic I visit every week obviously had a big envy
thing going on with Helen, my doctor and the woman I have devoted myself
to. Instead of my normal dose of oestrogen she took advantage of Helen's
absence and hiked up the treatment considerably, threatening to report
her to the medical board if I ever revealed what she had done to me. I
had no choice but to accept my fate and go through even more hot flashes
than I had ever experienced. I mostly stayed in ... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  

Chapter 9 Chrissie gets her fix

Chapter 9
Chrissie gets her fix

I woke up drenched with sweat as a rush of hormones heated my body to
what felt like a boiling point. The sun was up and I could sense it was
relatively early. I checked my phone for the time and saw it was 7:00 am.
I lay in bed for a few minutes thinking of the events that happened
yesterday: my first day as a t-girl prostitute at Derek's brothel in
Mayfair and the package of my new maid's outfits that I picked up from
John Lewis and the new rules that had been laid down by my new owner,
Helen. Just a few days ago I had just been a cuckolded husban... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  1

Chapter 10 Chrissie licks mommy clean again and ag

Chapter 10
Chrissie licks mommy clean again and again

My mother called out to me as she entered Helen's apartment through the
front door, which I was not allowed to use. I was consigned to the
service entrance at the back of the apartment, as most servants were in
Victorian England. In the 21st century it was rare to have a maid in
London, let alone an indentured sissy maid that, not only waited on her
mistress hand and foot, but worked during the daytime as a t-girl
prostitute for the sole financial benefit of his owner. It was a fate I
was led into over three years ago when my w... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  1

Chapter 13 Chrissie gets spunked

Chapter 13
Chrissie gets spunked

As mommy and I walked down the street, arm in arm, on a sunny August
Saturday afternoon in London I felt happier than I had been in years. I
was 30 years old, had a pair of tits to rival my mother and we were both
dressed to kill; in above the knee skirts, heels and silk blouses.
Underneath we had matching bras and panties and natural coloured hold
ups. We caught the glances of virtually every alpha male on the streets.

Mommy is 55 and looks a decade younger and is every young man's fantasy
of a hot mature woman. I look more like her younger s****r... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  

Chapter 14 Chrissie Gets Some Payback

Chapter 14
Chrissie Gets Some Payback

It was late Saturday afternoon when we finally arrived home. Mommy was in
a wicked state of sexual bliss brought on by the humiliating session she
had f***ed me to go through with a professional mistress. Her beautiful
face was flushed with desire. Mommy had grown to love putting me through
degrading experience after experience but this time she had gone way over
the edge. I had been f***ed to service over two dozen faceless men in a
filthy glory hole in a sex shop off a narrow alley in Soho, spending more
than two hours on my knees under the ... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  

Chapter 16 Chrissie & Kate

Chapter 16
Chrissie & Kate

It was the end of our first day of the working week and mommy and I
sneaked into one of the empty rooms, locked the door and climbed on the
bed. She lewdly spread her legs allowing me to lick her pussy clean,
savouring the scent of her juices and the remnants of the many men who
had been inside her. She let me tease her clit briefly but was too
sensitive to let me carry her to a climax. After I was finished I wiped
my lips with my hand and looked down at my mother's beautiful body.

"I'm leaking like crazy, as usual," I said with an embarrassed laugh.
... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  

Chapter 17 Chrissie sees Magic Mike again

Chapter 17
Chrissie sees Magic Mike again

It's difficult making polite conversation with a guy whose wife is quite
obviously getting drilled by someone else in the room directly above but
I've got firsthand experience being cuckolded and it's happened right
before my eyes a few times. Furthermore, the Australian I was sharing a
sofa with had married my mother and any man who did that with his eyes
wide open would know how unlikely it would be that she would remain
faithful. Nevertheless, I did have some sympathy for him. He had, after
all, been in a plane for over 20 hours and tho... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  

Chapter 18 Chrissie looks forward to getting debal

Chapter 18
Chrissie looks forward to getting deballed

Kate and I watched the video of Magic Mike in bed later that night or to
be more accurate, Kate watched the video on her laptop while I licked her
well used pussy. I could sense that she was having a hormonal rush at the
same time my careful attention brought her to an orgasm.

It is strange having a relationship with a woman I'll never be able to
have sex with, particularly when sex is her livelihood. I know Kate has
been a hooker for ten years and simple mathematics tells me that she's
had sex with thousands of real men duri... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  

Chapter 20 Chrissie hears wedding bells

Chapter 20

Chrissie hears wedding bells

It's been six months after I first started working in the brothel with
Kate and mommy and I've made friends with most of the girls who work
there and, more importantly, they are starting to think of me as a she
instead of a he. I think getting castrated was the best thing for me. It
boosted my confidence in my appearance and took away all vestiges of my
manhood. I do have a little penis but I don't think it detracts from my
appearance at all. It is easily hidden in clothes as it lies flat when
pressed against tight knickers. It's just a bare... Continue»
Posted by klammer 1 month ago  |  Categories: BDSM, Fetish, Shemales  |  
  |  1

True Story - about Fucking my Mouth.

We walked into his apartment and he said we can be comfortable here in the living room. He started to remove his pants, so I did also. He was down to his bikini panties and after he took off his shirt, he pulled his panties down and off. He was now nude and I got my first look at his cock. He looked large, long that is and he was cut. I finished removing my shirt and stood there in my garter belt, black stockings and black bikini panties.

He said, “Nice.” I had told him over the phone what I was going to wear.

He sat on one end of the couch and I sat on the other and looked at his... Continue»
Posted by guycd 1 month ago  |  Categories: Gay Male, Hardcore, Shemales  |  
  |  4

Mon nom est Angie [1]

J'ai 18 ans et j'habite dans une petite ville du Vaucluse. Comme tous les adolescents de mon âge je me branlais devant des pornos après les cours ou lorsque mes parents n'étaient pas là. De nature curieux, j'ai voulu savoir ce que ça faisait d’être une femme. Pourquoi? Je pensais que c'était mieux que d’être un homme. Depuis que je me suis mis cette question en tête, j'ai essayer de trouver un moyen de se sentir femme au moins une journée. Le seul moyen que j'ai trouvé était de me travestir, alors je me suis mis en quête de féminité.

Je me suis préparé pour aller a une soirée chez des amis ... Continue»
Posted by AngieTv 1 month ago  |  Categories: Fetish, Masturbation, Shemales  |