Shemales Porn Stories
Page 65

Mistress sissy slut

Waking up, sometimes, can be rather difficult to do, especially when you know that you were d**gged the night before. Or, at least you HOPE it was only the night before. And this time, it was far worse than the first times. So many things have changed about me from the first time I was d**gged, unwittingly and unwillingly, though as I look back, I can’t really say that I am upset about the outcome of each of these times. Well, I have to admit that I was, kind of, pissed off the first time, as I never really expected something like that. But that was quite some time ago and now, well, I gues... Continue»
Posted by Latexslav3 7 months ago  |  Categories: Shemales  |  
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Born to Be a Girl: M***rs' Choice

DISCLAIMER: This story is solely a work of fiction. Any similarities between people living or dead is purely coincidental. No a****ls were harmed in the writing of this story.

Are you familiar with those stories where the f***r raises his daughter as his son, because he is desperate for at least the appearance of a male heir? This is one of those stories, only, it isn't.

My m***r had already raised a son, birth to adulthood, when she became pregnant with me. She was determined to have a girl, come hell or high water. My m***r, by the way, essentially ruled our household. When I was b... Continue»
Posted by seityn 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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My New Need

Hello Doctor, I hope you're doing well. I’ve got good news. My doctor submitted her approval for the first SRS (sexual reassignment surgery). Since I'm not responding very well to HRT I'll be castrated so that my breasts will hopefully respond. I'm thinking of trying to have it done online. I think I would be able to get a lot of people to watch and pay $100. to watch.

I know that this is kind of long but I’ve been writing it for a few days now, and it is as much for me to kind of work things out in my head. I hope you don’t mind me using you as a listener.

I was just going to tell you... Continue»
Posted by subjaye 7 months ago  |  Categories: BDSM, Fetish, Shemales  |  
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CD Experimenting with bear

I've been wanting to try cross dressing for a while now.
I've been hooking up with this bearish guy I met on grindr, and after one of our later fucks he told me he wanted me to dress up for him. I was shy in accepting at first, but I knew I wanted it. I got some clothes for the next time I'd be seeing him. I'm pretty average in terms of body, but I have a nice ass, so I got these red and white striped leggings to show it off.The bends in the lines once it gets to my ass really show off how tight and perky it is. His house is close to mine, and I walk there once it's dark.
I've got a... Continue»
Posted by bottom1418 7 months ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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The degradation and the extasy part 1

I started the same as anyone else dressing up in private, i soon moved on to make up and wigs and within a few months i was just so turned on i joined a swinging site it was for guys and tv/cds and it was fab!
I got message after message telling me i was beautiful and how much they wanted me how id made there cocks hard etc, I loved the attention i wasnt going to meet i always said and they would beg but i never did.
After a week i got an email unlike any other " you are just a filthy fucking whore" was all it said i looked at the profile and went weak at the knees his profile picture was on... Continue»
Posted by jtrapperj 7 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Daughter Makes Dad her Sissy

It had been a difficult past three years for Steve since his wife Amy had left him. She had left without warning. She just picked up one day and took off without even a final goodbye. And she left their daughter Jen with him to raise.

Well, that wasn't exactly the story. There had been hints of Amy's frustration for years. At some point, she must have cared for him, but for so long she had lost all feeling for him.

After their marriage, Steve had become boring. He gradually didn't want to do anything fun, especially in the bedroom. He would go to work, come home and watch TV, and then ... Continue»
Posted by drew1207 7 months ago  |  Categories: Fetish, Shemales, Taboo  |  

Tables are turned.........

I had dressed casually for my trip to the spa, nothing fancy, plain soft cup bra, lace matching panties and a 4 inch beige sling backs, I had only lightly made up and put on a little perfume. With a loose fitting floral dress and my hair tied back I was ready for a treatment day.
As I was about to leave the house two things happened that would change the scenario. The first was I received 2 separate bouquets. The first was plain red roses with a note saying plainly "I owe you, thanks" Alistair and a single kiss. The other was from Mistress and was large and exuberant display of early summer b... Continue»
Posted by LaceTops4U 7 months ago  |  Categories: Fetish, Mature, Shemales  |  
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Tables are turned......

I had dressed casually for my trip to the spa, nothing fancy, plain soft cup bra, lace matching panties and a 4 inch beige sling backs, I had only lightly made up and put on a little perfume. With a loose fitting floral dress and my hair tied back I was ready for a treatment day.
As I was about to leave the house two things happened that would change the scenario. The first was I received 2 separate bouquets. The first was plain red roses with a note saying plainly "I owe you, thanks" Alistair and a single kiss. The other was from Mistress and was large and exuberant display of early summer b... Continue»
Posted by LaceTops4U 7 months ago  |  Categories: Fetish, Mature, Shemales  |  

Becoming Macy Ch. 01

My continued exploits with Steve, The middle aged bodybuilder. I began my transition publically while with Steve. . . . only seems right to start with him. In this chapter of my life I had just began transitioning. . . . .

. . . . . . . . . . Steve and I had been together for close to a year. In that time we had spent a lot of time together quickly. We practically lived together now. Either his apartment or mine, we were always together. We had been experimenting and exploring each other’s fantasies little by little, little more daring here and there. Steve wanted to pl... Continue»
Posted by MaskedBottomBoy 7 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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Chapter 3 - Cotton Candy


Hee hee hee! Baby we're only just getting acquainted!


I thought I just did?


Ha ha Haa!... I LOVE YOU, BABY!

I thought... you said.... we were just... getting acquainted?

Well, is it working?


. . <much more heavy breathing> . .

So... You were a pervert right from the beginning, huh!

Well it's kinda hard NOT to be when ya got tits AND a cock! Back when I first started showing my femininity I was my own wet dream. All I had to do was look at myself ... Continue»
Posted by ejax 7 months ago  |  Categories: Masturbation, Shemales  |  
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Sissy Patti - My Toy, My Lover Ch3

Sissy Patti - My Toy, My Lover, Ch 3

By CDJackie

When I got to my bedroom I fluffed my pillows, pulled the bed spread and blanket back then crawled on the bed to lie on the nice cool sheets, leaned back against my pillows and stretched out. “Phew,” I exhaled long and slow. It had been a pretty tiring afternoon but the results were quite satisfactory. I had fully laid out our relationship and exactly where she stood, my immediate plans for her continued sissy girlie-boi transformation and we had then had a hot fuck session.

It felt so relaxing just laying back, my mind cleared of ... Continue»
Posted by CDJackie 7 months ago  |  Categories: Fetish, Shemales  |  
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My First Trick

It Was my first trick. I had been living with Adam for over 2 months and he was getting real upset with me using so much. I was shooting twice a day and it was getting Adam mad. So he told me that if I wanted to shoot twice a day that I had to start paying my way. What the fuck did he care, I mean I was cleaning the house, and cleaning up after his friends. I shared his bed, and he wanted for nothing sexual because I was there for him no matter what he wanted, and bitch or gripe when he wanted a 3 way with that skinny bucked tooth Bobbi.
“So how do I do this?” I asked him after he brought it... Continue»
Posted by subjaye 6 months ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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Josh's surprise...........

The next morning I was awake with the larks, that what an early night does for a girl. After showering I quickly dressed, nothing fancy, a soft cup pale pink bra, with lace trim, a matching pair of panties, as much as I like thongs, when I don't have an erection I find my cock finds it's way out the side and leaves an unsightly cock bulge. I choose a simple blue and white stripped cotton stretch shirt, a darker blue stretch pencil skirt and 3 inch kitten heeled sling back sandals. I put on a small gold chain and hoop earrings, the sl**pers and done their job and my pierced lobes were healed. I... Continue»
Posted by LaceTops4U 6 months ago  |  Categories: Fetish, Mature, Shemales  |  
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Chapter 5 - Eat At Joe's

Hey, that guy over there just bought you a drink.

Yeah, and his wife just bought us dinner.


Yeah, she just paid me a hundred bucks to cum on her in the ladies room.


Hee hee hee hee!! ... Hey, you'll never guess who I saw over at the blackjack tables....


JOEY!! You remember Joey...?

How could I forget?!

Well, c'mon, I'll introduce ya!


Well, why not?

Posted by ejax 6 months ago  |  Categories: Masturbation, Shemales  |  
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Manchester Tranny Outdoor Fuck

I thought i’d tell about a meet I had a few years ago with guy from Manchester. We had been chatting on Squirt and we agreed to meet one Sunday night in a car park out past hyde.
He requested that I wear boots, stockings and a dress and that I was fully made up. This was no problem as I kept myself shaved all over and I was used to going out on the Manchester TV scene. He also instructed me not to wear any panties.
It was dark by the time we had arrange to meet and I drove into the car park, it seemed empty and large and as I hadn’t been there before I was unsure of its layout. I got out of ... Continue»
Posted by nnickk 6 months ago  |  Categories: Anal, Fetish, Shemales  |  
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When I got home after meeting with "Ken" and "Karen" and was unpacking and storing my stuff I found a piece of paper that I didn't pack. I unfolded it and it was a note from "Karen". Apparently she had written it when I had went to the bathroom to clean up and "Ken" had gone to the kitchen.
It said:
Hey. Had fun tonight. Would love to meet with you again, just the 2 of us this time.
Call or text me. K
I put just her name with the cell number in my phone and then flushed the note telling myself that I would DEFINITELY be getting in touch with her as soo... Continue»
Posted by Thaumaturge 6 months ago  |  Categories: Anal, Shemales, Taboo  |  
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A Plaything For the Guys (Part 1)

“So, Ronnie, how about another drink?” George asked me.

“Oh, George, I’m so d***k, but what the hell, sure, I’ll have another.”

“Thassa boy,” said George.

“Let me hit the head, George,” I said and slid out of the tavern booth, then staggered to the bathroom.

Once inside, I locked the door long enough to take off my pants, then my jockey briefs. and stuff them in my pants pocket after I’d put my pants back on. I looked at my swaying image in the old mirror over the sink. I smirked and pulled down my fly, and pulled out my hard cock. Then I almost fell over, and decided to stick my ... Continue»
Posted by ssup28 6 months ago  |  Categories: Shemales  |  
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Bobbi - New Girl in Town
(TV, Transsexual, Prostitution, Gay & lesbian sex, Anal, Oral)

[Note: the original author of these stories prefers to remain

Margo sat next to me in the coffee shop late that Saturday afternoon.
His real name was Mark, but he was one of the loveliest Drag Queens in
New York City. I had been dressing secretly at home in my mother's and
s****r's clothes for just over three years, but at 18 years old, I had
never been in public as a woman. Margo lived now as a female, and could
pass anywhere. I complimented "her" on it, and "she" said,... Continue»
Posted by klammer 6 months ago  |  Categories: Gay Male, Shemales  |  
  |  4


(Transvestite, Hetero sex, Spanking)

This story contains elements of cross-dressing, a somewhat dominant
female, and a rather submissive and effeminate male. If such things
make you want to toss cookies, don't read it, eh?

This story also contains one fairly graphic scene of eroticism between
two consenting adults. If *that* squicks you, what the hell are you
doing on this group? Grow up and get a life.

Part 1: The File on Lee

I was pretty tired when I got to Nancy's. Long day with the little
darlings (that's undergraduates to the uninitiated), inc... Continue»
Posted by klammer 6 months ago  |  Categories: BDSM, Shemales  |  

]Aunt Karen and Her Niece Andy

Aunt Karen and Her Niece Andy

My name was Andy now it's Amy. This is my story.

When I was twelve, I became fascinated by women and their clothes. I
still don't know what caused my fascination. I do know that my
interest increased with each passing day. Maybe it was puberty, or an
imbalance of hormones or as I've recently come to believe, I was a
person born genetically different. All I'm really sure of is ... I'm
glad it happened.

The initial stages of my quest for feminine knowledge took the form of
comparing women when they weren't conscious of my appr... Continue»
Posted by klammer 6 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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