Shemales Porn Stories
Page 60

A Fantasy

For leannaxtsx

During the flight he had a hard time falling asl**p. He kept all her posted pics in his phone and went a few times to jerk off in the bathroom while looking at her body. When he found out he was about to go to a convention for 3 days and as it happens to be the convention was at New Orleans he arranged to stay for a few more days "to see the sites". Now he was on his way and he knew he had to wait for 3 days until he could meet her. He contacted her a week before, at first she wasn't very cooperative but he managed to convince her they should meet. He promised to... Continue»
Posted by mobi_dick 1 year ago  |  Categories: First Time, Shemales  |  Views: 1066  |  
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the real me part three

Just then the phone rang and mom handed to me it was Mike he said that he couldn't belive it was me he seen at the store.I told him yes it was,then asked if he wanted to still be friends.He asked well you going to dress like that always now?I said well do you like the new real me,he said well I love the new you.Mike told me how he got hard thinking about me that way.Well what your mom say i asked. He said it was up to us what we wanted to do.I asked did your mom say anything to you about her and my mom being lesbain lovers? Yea she did he said, ok then we are cool with them.
He then asked m... Continue»
Posted by cdpaula 2 years ago  |  Categories: Gay Male, Shemales, Taboo  |  Views: 809  |  
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Can i help you with that?

Yes being a shemale does present itself with certain unique situations for time to time, none so unique as the other day, in fact, when at the mall, i had to piss so bad, so i went into the ladies room, of course, dressed in a blouse and tight jeans. I found an empty stall, wnt in but had to go so bad, and you know what i mean, you lose track of all else, thus i left the stall door open, well it all worked out for the better! I was standing up and pissing when this hot MILF opens the door, sees my cock in my hand and asks me if i need any help! Help? I knew what she wanted so i asked her in an... Continue»
Posted by cumsquirter 3 years ago  |  Categories: Shemales  |  Views: 2589  |  
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How I Became Vanessa Chapter 2

Hello dear readers,

I strongly encourage you to read the first chapter of this story to fully grasp the sudden changes which affected my life.

I dressed up with a very tight black long sleeves top and a black mini-skirt. I added a choker necklace like the one Elena used to wear. I chose a pair of black fence net thigh highs to show my beautiful legs and stiletto high heels. I also chose to wear my shorter blonde wig (jaw-length) and some heavy make up.

I didn't know I wasn't alone. I was starting to prepare my ass with some lubricant and to squeeze my big black dildo in when Elena cam... Continue»
Posted by slutyvanessa 2 years ago  |  Categories: Shemales  |  Views: 546  |  
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Panty Boys

By Fred Gingerman

Chapter One - Nerds United
My name is Mickey Donaldson. For most of my 16 years, the k**s have called me Mickey Mouse, because of my size and because of my shyness. I was only 5'3" and at 115 pounds, very skinny. My best friend Jeremy Haskins and I were always the oddballs. Jeremy was a little bigger at 5'4" and 120, but we weren't being recruited for our high school football team. Chess team was more like it.
We were pretty much classic nerds. Shy. Picked on. Ostracized. Intelligent.
But we were still 16-year-old boys and our hormones were stirring. Boiling actually. ... Continue»
Posted by BeeJay69 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  Views: 4839  |  
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Willows transformation 2

"Now the preliminaries are over, and it's time for the entertainment part of our evening!"

That was what Fern, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Jason. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completing the transformation.

Fern had found a magazine I'd left on the bedroom floor, showing a transvestite being tortured and humiliated by a couple. Although she had always known I liked to crossdress, she had never paid any attention to that side of me. Now she had ... Continue»
Posted by stig1963 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 561  |  
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late night hotel halls

I am 46 years old and travel quite extensively for
businss. I dress in my hotel room at night when i travel.
I sometimes entertain in my room. Sometimes I get very bold and wander out to the soda machine dressed sexily. Its about as bold as I ever get. I am quite tall and do not pass in public. But i am very smoooth and try very hard to look fem.

Anyway, very recently i wandered into the hotel halls about 3 am at a business hotel I was staying in outside of
Indianapolis. The soda machine was at the end of the
hallway. I looked up and down and when i thought the coast was clear I... Continue»
Posted by cherylfabrizio 2 years ago  |  Categories: Shemales  |  Views: 1543  |  
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She tricked me & am I glad

My most frequent fantasy is to be dressed like a slut for black men. I think about it at least 3 times a day. The most recurring fantasy is when I meet this black woman that turns me on. We talk for awhile and it seems like we are hitting it off pretty good. Then out of the blue she asks me if I want to continue this conversation at her place. Could I be this lucky? This fine black woman was inviting me to her house? Yes I told her smiling from ear to ear. She smiled back and told me to follow her. We get to her house and she tells me to have a seat while she gets more comfortable. I am sittin... Continue»
Posted by iwannabeacumslut 1 year ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 1586  |  
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My New Whore

Disclaimer: All characters portrayed are over the age of 18. Any similarities between persons living or dead is entirely coincidental and unintentional. These characters are entirely of my own creation, and thus don't belong to you. Don't use them or this story for your own purposes. There's a reason they belong to me.

Justin's body trembled, as he sat in his chair, his eyes glued to the floor. It was obvious from his reaction that he hadn't expected me, or anybody for that matter, to walk into his apartment that night. We had been friends for several years now, and though it ... Continue»
Posted by BigStevieAwesome 3 years ago  |  Categories: Anal, Shemales  |  Views: 702  |  
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A night of passion

Will led Sarah by the hand into his bedroom. He closed the door as they entered and pulled her towards him. He placed his hands around her, caressing her toned stomach as he slightly nibbled on her earlobe. He could feel her trembling in his arms. Sarah lightly ground her ass into his crotch, rubbing herself against his hardening cock.

“Mmm,” She moaned, feeling Will’s lips kiss the nape of her neck, causing her to break out in Goosebumps.

She turned to face him, wrapping her arms around his neck, drawing him close. They kissed, tongues intertwining. Will could feel the hardening bulge ... Continue»
Posted by gellid 3 years ago  |  Categories: Shemales  |  Views: 2549  |  
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becoming Rachel 2 - A night out at a fetish party

So I had been Rogers trans-mistress for about 2 years. as he was also a p/t Tranny he had taken me on as his little teen (19 year old) apprentice tranny.

he was in his mid-40's, he taught me how to walk, how to sit, how to talk, how to suck cock and deepthroat, how to fuck. lately he had me taking some estrogen tablets which had made my skin softer, changed my voice and given me little cheery nipples. I liked all these changes and Roger told me that we would eb going to a 'party' i was very excited by this, as I hadnt been out dressed much and really liked it when I did. Roger bought me a h... Continue»
Posted by rachel_cd 1 year ago  |  Categories: BDSM, Group Sex, Shemales  |  Views: 1064  |  
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Caught in the act

After my first encounter with John’s dick, I couldn’t get it out of my mind. Two weeks later we met at a friend’s party and we talked about it. He was worried his girl friend might find out. I told him he had noting to worry about as I had as much to lose as he had. But I also said it was the best sex I ever had & wanted a repeat performance. He agreed it was fun but felt to do it again would be risky. I said all we needed was an excuse to go away for the weekend. I told him to leave it to me.

I happen to mention to his girlfriend later that John & I were thinking of going away to see a ba... Continue»
Posted by monkeynuts0 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1388  |  
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The real me part one

Well let me began Iam not in the closet, I grew up in small town my mom raised me cuz my dad was not around. This town was dead and in my school days there was only myself and friend of mine that were the only k**s in town. It was summer and my friend had left to go spend the summer with his grandmother in other state.
My mom was a 5'9" 130 lbs d breast woman that raised me and worked her but off doing it as only hair stlies around for a 100 miles. She always wore dress and skirts and heels dolled up everyday. So oneday I was bored around the house when she was home taken a break. We were... Continue»
Posted by cdpaula 2 years ago  |  Categories: Gay Male, Shemales  |  Views: 1530  |  
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My CD friend

This story is fiction.

~~~~~~~~~~~~~~~~~~~~~~~

I had been chatting to people on a ts chat room as I had recently become accustomed to do, when I received a private message from a local cross dresser. She asked me where I was from, how old I was etc and we found out we lived a few towns away from each other, both young guys and both really loved wearing women's clothes.

Admittedly she was much more experienced at it than me, having access to girlfriends, s****rs and mothers clothes and had even ventured out fully dressed once!

Eventually after some light chat, swapping dressing up s... Continue»
Posted by shyadam89 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 547  |  
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A true story: me and a transvestite man - part 3

This is the last part of my true story. I had expected it only to need two parts, but it seems that I'm quite a wordy writer, so it now spans 3 parts.

Where did I leave off last time? Oh yes; Toni, the gorgeous Brazilian TV was leaning forwards, dressed in her black lingerie, her firm arse towards me, ready for me to enter her. Read on...

I wasn't expecting this to go well, as I'd only had a little anal sex before, with a woman, and this had been on a bed, where I could jockey around for best position. However, thanks to my extra height (6'3" against Toni's 5'10" or so) we seemed a p... Continue»
Posted by LookingForSomething 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 670  |  
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Sissy Emma is Turned Chapter 4

I couldn't go outside dressed like that could I?

Here I was f***ed to dress like a slut in locked on heels, barely black stockings, mini skirt, frilly white blouse with which could clearly see my black bra and 38d breastforms and heavily made up face. I would have looked like a reasonable vision of a woman, albeit a very slutty woman other than the fact that my new Master and my ex-wife had failed to give me a wig. So to anyone seeing me it would be clear that I was in fact a feminised male. This was going to be humiliating.

But I couldn't think of a way out. At the least it was going to... Continue»
Posted by emmahighheels 1 year ago  |  Categories: Shemales  |  Views: 1224  |  
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My New Girlfriend Turns Out to Be a Shemale.

Where do I start?
How about at the beginning. My name is Cal I am divorced and living alone. I am not a bad catch I am five foot eleven, short black hair, green eyes and no visible scars. I am a regular at the gym so I am in shape but not ripped. A seven inch uncut cock that I can use well. I dress nicely and have a good job.
My friends Don and Lisa were feeling sorry for me they knew how ugly my divorce was and how lonely I was so they invited me to their pool party last weekend. They said there would be some single women there and I might find someone I like.
Okay, I thought at... Continue»
Posted by triphammer73 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 3620  |  
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The Bondage Whore, Chapter 6

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.



Chapter 6 - A Visit from Randy


"Randy!"

Rachel was thrilled to see her friend and old streetwalking regular from days past, step around the stock. He immediately popped out the gag, and gave Rachel a friendly kiss. Rachel melted.

"So glad to see you Randy! Although I feel a little embarrassed to have you see me like this."

"Hey sweetie, c'mon, I know what you do. And I must say, WOW, what a view." Randy took a step back and around the stock, enjoying and taking in the entire picture. "Yup, wow! Don't know quite ... Continue»
Posted by thongcutoffs 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 695  |  
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A TV in the Shoe Store



I work at a ladies shoe store at a large metropolitan mall.
My name is Jillian, though my friends all call me Jilly.
Those same friends also say that I am blessed with a
beautiful face, and an athletic body! Pretty heady for a 30
year old woman whose ideas of athletics never got beyond
sports illustrated and Cosmo! But friends tend to flatter,
that is why we are still friends! I tend to dress with a
flare towards teasing. You see I always wear my skirts and
dresses a bit shorter than fashion demands, and I always
wear sheer reinf***ed heel and toe stockings. A habit
started by a ... Continue»
Posted by jillynylons 3 years ago  |  Categories: First Time, Shemales  |  Views: 1939  |  
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"Not MY Type?"

I’d known Kelly for most of my life. Growing up I spent most of my time at her mother’s house. It was a way to escape and avoid my parents constant arguing and fighting. It was a pretty well established fact that Kelly was lesbian early in Junior High School. Her mom and I became quite close as I was rapidly replacing the little girlie daughter she was losing to an ever increasing “butch-ness”.
By twelve years old I essentially become like a member of their f****y. Over the next few years they had the opportunity to watch me morph from a small frail Christopher into a pretty, petite and... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Shemales, Taboo  |  Views: 1334  |  
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