Shemales Porn Stories
Page 66

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 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
197
  |  
100%
  |  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 9 months ago  |  Categories: Fetish, Shemales  |  
581
  |  
100%

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 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
105
  |  
100%

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 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
161
  |  
100%

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 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
226
  |  
100%
  |  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 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
742
  |  
100%
  |  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 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
163
  |  
100%

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 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
143
  |  
100%

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 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
372
  |  
100%

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 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
137
  |  
100%

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 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
597
  |  
100%
  |  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 9 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
4115
  |  
100%
  |  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 9 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
856
  |  
100%

Following on from the signing of the contract ...

I lay on the table, my erection had disappeared and my limp cock still smeared with maids lipstick lay on my thigh. The restraints were so tight that i was already noticing that my feet and hands were without feeling and i could imagine them biting into my flesh much as they had done with maids when she was strapped onto this same table moments before. I waited looking around me and taking in more of the surroundings, i noticed just how many fixing points were around the room, there were O rings and O bolts screwed or fixed into the walls and ceiling wherever i looked and i could only begin to... Continue»
Posted by oldognewtrix 9 months ago  |  Categories: BDSM, Mature, Shemales  |  
543
  |  
100%
  |  1

The new "Girl" On the Boat, Part 2

A recap: My career was spent as the Captain of a 100' high-end charter boat in Alaska. I had a crew member leave the boat on an emergency, and my office sent up a new crew member for me. Normally I interview a potential employee before hiring them, but in this case I needed another crew member fast, so he was hired sight unseen by me. His name was Louie, and he was a short, slight of build young man in his 20's. It turned out that he was also a cross dresser, and when a 'woman' her name was Louise.

The first night we had sex was while we were at anchor waiting for a storm to end. Loui... Continue»
Posted by 1kaaboom2 9 months ago  |  Categories: Fetish, Shemales, Taboo  |  
1354
  |  
100%
  |  2

tv sex

4 week I was in a well known high street shop that sells men and ladies clothes..i was looking at jeans I went to try them on in cubicals men to the right ladys to left .as I shut main door it caused a draft and blew a curtain open I see this guy with good size cock in suspenders belt black stockings with his cock and balls on show he was clean shaven.i didn't bother buying any think as all I could think of was his little arse and cock I wanted to fuck him as its been about 14 months since my last had tv sex.i waited out side for him to come out wen he did he was dressed in the black stocking... Continue»
Posted by feormale 9 months ago  |  Categories: Anal, Group Sex, Shemales  |  
3371
  |  
100%
  |  1

Daddy's Little Slut

Here I am, surfing on my favorite porn site. My dirty little urge has taken hold of me again. After a long period of deniying myself the need to dress up, i relapsed again. I bathed and thought of trimming my pubes a bit, but ended up shaving myself completley again. I tend to do it in my urge to cam and show off my sexy body and after cumming i regret it instantly. It makes my life difficult because i have to hide my hair free body from all my workmates and friends. So here i am, shaved, smelling really good from my favorite gucci scent, wearing my dark hair wig, my sexy stockings and lingeri... Continue»
Posted by ignitron 9 months ago  |  Categories: Fetish, Masturbation, Shemales  |  
3281
  |  
100%
  |  4

Dragon's Hole Part 2

On the long trek back to the room, something else catches your eye, another sign. This one says Dragon’s Persuasion. Just the name on the sign is enough to pique your curiosity, so you turn and head down this hallway. Unlike all of the other halls that are adorned in medieval decorations, this one has various colors running horizontally down the hall. The colors, you notice, are the colors of the rainbow, but very faint. You wonder what could be down this hallway and continue along until you reach a heavy oak door. You push this door open and right away, you hear moans. Not the same moan... Continue»
Posted by sabre72 9 months ago  |  Categories: BDSM, Fetish, Shemales  |  
1150
  |  
100%
  |  2

First meeting with Dom sissy mistress

I was a longtime secret panty sissy who played in private and only dared dream of finally meeting someone face to face when I met Miss Jamie on xhamster. We had an immediate rapport online and before long she suggested meeting. Of course, with her long experience as a sissy, and with me being an obviously natural submissive, she would take the role of teaching me my proper place as a submissive sissy. This is the account of that first meeting.

Miss Jamie's logistics were simple:
I was to park at a nearby shopping center and wait for her.
When she arrived, I was to get in her car.
She wou... Continue»
Posted by Shelleyisasissy 9 months ago  |  Categories: Fetish, First Time, Shemales  |  
1884
  |  
100%
  |  1

Brittany The Cheerleader

It was my second year as an assistant counselor at River High School. I was young, in my mid twenties. Everything was typical in the small town school. I would help students with scheduling issues, direct them towards colleges, and help them with different scholarships and programs that would benefit them. It was entirely unremarkable and nothing out of the ordinary happened until I met Brittany.

One day a woman walked into my office. She was tall for a woman of her age, yet very slender and petite, with an almost non-existent chest, gorgeous round bottom, tanned skin, and long deep brown... Continue»
Posted by wedgietime 9 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
7296
  |  
100%
  |  1