Shemales Porn Stories
Page 81

The Wild Isabella

This is about the woman of my dreams. That I long for. That I crave. So let me tell you about a moment of madness I will never forget.

Her name was Isabella and she looked nothing like the posts on the forum. I'd heard reports that she was over 6ft, that she was fat, that she was not for the inexperienced.

It took an age to find her apartment and when I got there she poked her head coyly round the door. She was slim and Spanish, with blonde hair and big, blue, mischievous eyes. Perky tits and an hourglass shape - she sure was fuckable; although we I never got the chance, as she was the... Continue»
Posted by waraxe13 3 months ago  |  Categories: Fetish, Shemales  |  
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Jamie's Descent Part 3

Jami’s Descent Part 3


The limousine took me to Harley Street, home of the UK's private health
industry, for the medical Vanessa had mentioned. To me it had seemed
less of a medical and more of a preparation for something. There were a
lot of the usual bl**d pressure tests and urine samples, but there had
also been a lot of measurements taken, especially around my upper body.
The doctor and nurses were efficient though and seemed satisfied with my
overall condition.

I felt the doctor spent a little too long on what he had said was a
prostate check. The doctor's finger seemed to ... Continue»
Posted by nikkiesilk 3 months ago  |  Categories: Shemales  |  
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Drink or Dare

crossdressing – threeway – first time – oral – anal – strap on

Ever since I was a c***d I had always fantasized about being a girl. Every chance I got I would sneak into my moms closet and try on her panties, slips, nylons and dresses. The feel of the sheer silks and nylons against my skin would drive me crazy. When I hit puberty and discovered the joys of masturbation these two activities seemed to combine perfectly. So much so that while jacking off dressed as a girl I would fantasize about being sexually used by men. Eventually I felt I needed a real life person to place my desire... Continue»
Posted by naughty_bi_interest 3 months ago  |  Categories: Anal, First Time, Shemales  |  
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An Interesting Friend CoCo

Hot CoCo!

Along the way I’ve had the pleasure of knowing 2 pretty nice ‘girlfriends’; one white and CoCo…hot and black. Casual, raunchy, sexy, free-spirited and just fun to be with.

CoCo was a marvel, a wonder of hormone therapy, with ‘her’ everything had gone perfect. She was about 5’ 8 “ with breasts that were well proportioned, not too big or too small, a great ass and killer legs. She was a little overweight, I’d just say a little ‘fleshy’, mildly attractive and oozed a physical glow of well being…along with a satirical sense of humor.

We met at one of those places that tried... Continue»
Posted by swat412 3 months ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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Football Mascot – Gabi

Football Mascot – Gabi

Gabi was sucking on his favorite dick stick, the one owned by the black tackle of his dad’s football team. Talon was massive all over, but especially his cock. One of Gabi’s hands was sliding up and down on it. Gabi’s other hand was stroking the massive cock of the Center on the same team. Larry was white and even heavier than Talon but his cock was slightly, but only slightly, smaller. Pedro was between Gabi’s legs using his own massive cock to gently slap back and forth against Gabi’s sweet peter. It was a game invented by Gabi. Pedro was the Latino offensive... Continue»
Posted by tankengine123 3 months ago  |  Categories: First Time, Shemales, Taboo  |  
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Picking Up a Sissy at the Grocery Store

Not my story, but very hot:

I saw you while I was walking through the grocery store. You were bent over, picking up something off the bottom shelf. At first, I thought you were a girl, because of your nicely shaped ass and the fact that your low rider jeans were riding down, exposing a lacy white thong.

I was so turned on, my cock started to get rigid right away. If I had been wearing jeans, I probably could have hid it, but as I was coming home from work, I was in a suit and tie, and the thin fabric of my suit pants did little to reveal my hard dick.

I walked up to you, expecting to ... Continue»
Posted by widendeep 3 months ago  |  Categories: Anal, Gay Male, Shemales  |  
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My first encounter with a man

As usual when I was travelling I was sitting in my hotel room working. I finished my work while drinking a beer or two, as the tingling feeling started to grow. In my suitcase I had packed my outfits and my toys ready for some hotel room action. Although; action meant myself, porn and self-satisfaction.

I took a shower and washed away all the dullness of a day on travel. I was stroking my cock and balls gently feeling the hairless skin glowing, and my cock started to grow. Since I was eager to save up for a massive load I finished the shower and started to get dressed.

The black panties ... Continue»
Posted by theevilothertwin 3 months ago  |  Categories: Anal, First Time, Shemales  |  
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A Dream Cum True

As part of the national sales f***e for my company I travel quite a bit for my job. As a result I have a lot of time to explore my sexual proclivities. I have taken to collecting panties, bras, nylons, a few wigs and a little bit of makeup that I often bring with me because I travel regionally and drive a lot. I like to meet up with strange men in my hotel room where I get dressed up, get on my knees and suck cock. At first it was just other gurls who like to dress. While they remain my favorite I soon discovered I just like sucking cock. If I’m dressed and feeling girly I’ll suck a man’s coc... Continue»
Posted by smilinwillie2001 3 months ago  |  Categories: Shemales  |  
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Daddy's Girl








Daddy's Girl

The Hitchhiker

It had been snowing all day. A wet, heavy incessant snow that was covering everything including the highway. Combined with a wind-chill factor in the teens, Christopher was almost frozen stiff. He was elated when the huge semi pulled over to pick him up. He climbed up into the cab and smiled thankfully at the driver.

"Thanks a lot mister. I was just about frozen out there."

"No problem, son." The driver smiled at him. "Name's Zeke," the driver said and extended his hand.

Christopher took the offered hand and shook it. His hand seem... Continue»
Posted by sissirandi 3 months ago  |  Categories: Anal, BDSM, Shemales  |  
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Jamie's Descent Part 5

Chapter 5


Fiona loosened the ball gag from my mouth and I gulped in lungfuls of
air. My jaw hurt like hell and my arse felt like it was on fire and I
slumped straight to the floor. Immediately, I felt tears spring from my
eyes as I began to realise what had just happened to me. I am not sure I
could tell you what I felt at that moment; physical pain for sure, and
burning humiliation. Mixed somewhere in there was also the memory that
at some point I had stated to enjoy what Fiona was doing to me. In some
dark corner of my psyche I began to feel that I had taken another step
into fu... Continue»
Posted by nikkiesilk 3 months ago  |  Categories: Shemales  |  
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Turned my Mistress

I woke up, groggy, in a world of bright lights and fuzzy shapes. I couldn't move properly, my arms slopping about like sticks. I turned my head, trying to focus on the world, but it just slumped to the side.

'Good, you're awake,' Came a sultry voice.

I heard loud clicking and out of the corner of my eye I saw a hazy black shadow tower above me. My mind wanted to say, 'who are you?' But all that came out was a few slurred noises.

A hand ran its way along my body until it held my face, tilting it upwards. 'Don't worry sissy. We are nearly there; one injection to go.' With that, My le... Continue»
Posted by waraxe13 2 months ago  |  Categories: Fetish, Shemales  |  
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Jamie's Descent Part 6


Chapter 6


Fiona leaned forwards, wrapped her arms around me and drew me into a
passionate kiss. My eyes closed instinctively and I swear I could my
heart pounding as her tongue snaked into my mouth. My knees almost
buckled, and I felt myself surrender to her lock, stock and barrel. I had
never felt this way before; my emotions had gone into freefall as my
head began to spin, and I almost fainted.

Fiona sensed this and caught me as I began to drop.

'Come on baby, let’s get you to bed. I think you’ve had enough
excitement for one day.' She whispered tenderly in my ear as she ... Continue»
Posted by nikkiesilk 2 months ago  |  Categories: Shemales  |  
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The Fire Alarm


I have a recurring nightmare. A fire alarm has sounded in my apartment building in the middle of the night. I've evacuated with the rest of the residents and am standing out on the sidewalk as firefighters rush into the building. There's no sign of smoke. It's cool out; a light drizzle is falling. I don't mind however; it's refreshing.

What bothers me is my gradual self-discovery that I've left my bed wearing pantyhose and panties. The red lacquer on my toenails is visible through tan hose's reinf***e... Continue»
Posted by Batman_112 2 months ago  |  Categories: Taboo, Shemales  |  
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L Is for Lucy

This was it. IT! THE chance of a lifetime. The sort of evening I'd been waiting so long for. A couple of times I'd thought my chance had come but each time something had gone wrong, someone had changed their mind. Either Mum, or Dad, or Stephanie, someone had decided to stay in. Or decided that I should go out with them. But this time it was going to be OK, it was going to work.

Stephanie - well, no problem. She was away at college now. She was a year older than me. I was heading off on my own soon, just hoping to end up in some sort of accommodation which would allow - you-know-what.

Mu... Continue»
Posted by Batman_112 2 months ago  |  Categories: Taboo, Shemales, Gay Male  |  
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RENT BOY: FEMINIZATION

RENT BOY: FEMINIZATION







Hey. My name is Lyosha. And this is my story. Enough fun, read, can enjoy. Maybe you want ...

I have not enough years to call myself a boy in the fourth ten years. But, as I said Ostap Bender, let him first cast a stone at me, who's to say it's a girl.

Although, although now I would so clearly himself did not speak. And then we can get the stone. And all that's why.

Yes, I have long been fond of the theme of trance. He liked me in all sorts of role-playing games, the image of the ... Continue»
Posted by Aleshka 2 months ago  |  Categories: BDSM, Shemales  |  
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Used by my daddy and his friends

After meeting Tel for the first time and being fucked by him i kept in touch with him online,

and he popped in to the chatroom some nights to watch me on cam.He said he enjoyed

watching me show off my cock and tight ass all dressed up and that i was his little slut

and he had a surprise for me at the weekend if i could come round his place. I said that

would be no problem and what did he have planned for me.He said not to worry its just

my next lesson and i would enjoy it.I wondered what he had in store for me and hoped

he was going to fuck me again maybe a little more gentle... Continue»
Posted by tanyacd65 2 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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f***ed to be Female Pt2

Back in my room I lay on the bed trying to come to terms with the fact that I was being f***ed to become a woman. I kept looking at where my testicles had been, trying to see what they had done to me.
My penis had been pulled back into the space where my testicles had been and then they had stitched it flat. I soon found that I had to sit in order to go to the toilet.
I felt my face and arms. They were so smooth and free of hair. My chest was bare and smooth too and I looked at my nipples for any tell tale signs that might suggest that I was growing breasts. My nipples felt sensitive and I c... Continue»
Posted by PaRiaH236 2 months ago  |  Categories: BDSM, Shemales, Taboo  |  
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f***ed to be Female Pt3

I woke up the next morning to find Ann in my room. She waited while I showered and put on some mascara and lipstick. Ann told me to wear my aerobics kit and watched me as I dressed.
"You know Susan, your boobs are starting to show" she said as I put on the leotard.
I felt my chest and it was true. My breast were beginning to develop enough to see and feel them.
"In a few weeks you will be able to wear a bra without any padding, Susan" said Ann and then added, "And by then we should be able to notice your hips and bum getting bigger. You should be able to try stockings and suspenders then"
... Continue»
Posted by PaRiaH236 2 months ago  |  Categories: BDSM, Shemales, Taboo  |  
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gangbang sissy

Back in the eighties I used to frequent an Adult Theater in DC. This was one of the places I frequented where I could dress openly as the woman I had always known I was as far back as I can remember but ever so tried to live in my pretend world as a man. They had a huge theater with a runway down the center for the many drag performers as well as the guy strippers. The movies were always decent and the performances awesome. So over the years I had enjoyed both the movies as well as the many sexual encounters I had with those that came and sat close and showed an interest in me. I also enjoyed ... Continue»
Posted by tanyacd65 2 months ago  |  Categories: Anal, Group Sex, Shemales  |  
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My Friends House Part 8

I felt so pretty, walking around in my outfit, all dolled up. As I was finishing the coffees, she came into the kitchen. I saw that she still had the white stockings on, white lace panties and no bra, and on top of that, a see-through bathrobe. She took the camera and placed it on the table, sat down and took a sip of her coffee.
“Sit down, Jennifer. I'm going to edit a video together to show how good a classy sissy whore like you, can be. And teach my son a lesson!”
I sat down and drank my coffee. I could see my lipstick sticking to the cup. I liked that very much. I felt very much like a g... Continue»
Posted by HosieryQueen 2 months ago  |  Categories: Fetish, Shemales  |  
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