Shemales Porn Stories
Page 16

Tropical Escort Pt. 1: Monday

So, this is a series of stories that are 100% true. I went through a separation from my ex a few years ago. This is when I really gave into my desires to dress and be with men. And as a gift to myself, I decided to go on vacation! To San Juan Puerto Rico at that. Needless to say, my shopping trips leading up to the vacation were rather fun and expensive, but who cares! This is a once in a lifetime chance, and I wasn’t going to let it pass me by. Besides the obvious thrill of being able to dress when I want, go out when I want…. I also wanted a man for my vacation. At least one. So, a few weeks... Continue»
Posted by elpaulito 5 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 2446  |  
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Tranny teacher

Hi Al, how is your house sitting summer going ? Pretty good Tim a little boring but the beach is nice. By the way, I didn't mean to but I saw you last night through my window... you were wearing woman's underwear. OH I hope I didn't disturb you Al. Actually I was totally turned on, especially when you pulled out your hard cock.

Really, if you like I can arrange for a private show ... interested ? I don't know I have never seen a man up close before. Ah.. well if you pretend I'm a lady I can walk you through some fun. So you will put on your stockings and the silky things. OH yes and a wig ... Continue»
Posted by TenderLoins 5 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 6012  |  
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Tgirl dominated by school Mistress part 2

This is the second part of “Dominant Female Teacher Makes Cross dresser Student”. It explains why I am what I am.
I got called to see Miss Jones, the teacher in charge of discipline at my school.
"So you are back are you? What do you expect? Well you are wrong for I demand so much more. Understand me about that."
"Yes Miss Jones, I understand" I was back in her school office again. Again I was nervous and excited.
She put down the file and looked at me. "It’s not a game it’s for real"
I nodded.
Miss Jones, head of year, came from behind the desk, her black stilettoes tip tapping lik... Continue»
Posted by SapphireSomeday 5 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 2204  |  
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Tgirl dominated by school Mistress

Mistress said I should tell how I first became sub so here goes.
While I was still at school I was very thin, hairless body, high pitched voice and long hair in the most girly look I could get away with. I had started wearing panties under my trousers and I thought nobody knew. Well one day I was told to see the head of year immediately. She was terrifying to us boys, in her 30's, tall, thin, long brown hair in a severe style, she would wear heels with metal tips to announce she was coming from a distance. Very sharp manner and uncompromising.
In her office in front of her desk I stood ... Continue»
Posted by SapphireSomeday 5 months ago  |  Categories: Anal, Shemales  |  Views: 1868  |  
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ROCKY YOUR MY GIANTESS

I have been having this wild hot dream of a friend that lives close to me a great tall CD I know on here and have been fantasizing of him getting much taller :

I see Rocky walking up the walk my huge breasts are heaving in my tight dress as I rub my big long gurl cock in my tight silk panties ,a knock at the door tells me he is here as I open the door he even with out his heels on is much taller by almost six inches his eyes are wide as he takes in my huge swelling chest that looms just below him my big clit is rock hard by now as I watch my friend get dressed he already has his long legs e... Continue»
Posted by rachels_pimp 5 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 284  |  
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Wife Fucked By Shemale

This is the story of me Rittu married to a guy named Harvinder in 1996. We had 2 k**s from our marriage .Harvinder was very fond of girls and even before my marriage he use to fuck prostitutes right from young girls to middle aged women. He used to get his cock sucked and even used to fuck these prostitutes in their ass. After getting married to him he used to apply all the tricks on me. He made me watch blue films and he get his cock sucked as women in bluefilm. He even used to make me drink his cum. He tried all the filthy things on me and now I feel like a big whore. Harvinder even used to ... Continue»
Posted by neo7x 5 months ago  |  Categories: Group Sex, Shemales  |  Views: 828  |  
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The Studio and the Shemale

When the company I worked decided to relocate to the north of England, it was made clear to me that there would not be a job for me there and so the decision whether to move woth or leave was decided for me. The redundancypayment was extremely generous, as it should be, I had been with them since I left school. So now I had to find a new job and the decision was whether to stay in the line I was in or change careers, but With the redundancy payment as it was there was no rush.
Quite by chance I discovered that a photographic studio, which was literally a 5 minute walk away was looking for an ... Continue»
Posted by dasilva1672 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 3210  |  
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The Cubicle

The mobile number I had been given I tried to ignore but the pull was too strong and I phoned it eventually. No real surprise there. A female voice seemed uninterested but perked up at hearing the names of the couple I had sex with for an audience. She invited me for an audition and gave me an address which turned out to be for an old converted bonded warehouse now offices. "Wear something sexy" she said.
The place was half empty and quiet judging by the carpark. The receptionist barely gave a very tall girl in a trench coat with 5 in heels and too much makeup a second glance so I suspect... Continue»
Posted by SapphireSomeday 5 months ago  |  Categories: Hardcore, Masturbation, Shemales  |  Views: 749  |  
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Elamehs night out Pt 2

so Now it was Sat morning as i had my encounter with my first shemale as i woke up and heard some noise in the apt..i hear Nancy talking on the phone. i assume it was her by the way her heels were clicking against the floor. i just laied in the bed. and then the door opend up and ther she was, standing there with black latex boots with 8in heels and a black latex top with her breasts fully errect. long blonde hair that was stunning. all i could do was look at her. she stood there talking on the phone and talking to someone,,{i think it was Jenny] about what she did to me last night. then sen ... Continue»
Posted by elamehs699 5 months ago  |  Categories: Anal, BDSM, Shemales  |  Views: 353  |  
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Elamehs night out

I Finally Got A Chance To Dress Up And Go Out My Wife Dosent Know Bout This She Went Away For The Weekend To Connecticut So I Dressed Up In One Of her Dresses And Finally Went To A gay bar Called The Cubby Hole In Manhattan NY


http://xhamster.com/photos/view/2889342-47848481.html



It Was A Nice Spring Night. So Off i Went To Finally Find A She Male. Oh By the Way I Have A Thong On And A 8in Butt plug Up My Mancunt.So I Hopped On The train To West 12st, And Let me Tell You It Was Great To See All those People Looking At Me On That train. So As I Got off And Started To Walk Down The... Continue»
Posted by elamehs699 5 months ago  |  Categories: Fetish, First Time, Shemales  |  Views: 1133  |  
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Elamehs night out

finaly i had time for myself..my fiancé finally went away to Conn for the weekend friday
morning. so i had all day to prepare.i started that eve to get dressed in her clothes.http://xhamster.com/photos/view/2889342-47848480.html#imgTop
this is what i wore..i have my 12 in butplug up my mancunt.. it was about 12 am
so i left to go to to A Gay Club In Lower Manhattan. i slipped out the back door so no one could see me and caught a cab. then i hopped on the train to the city. i felt so free that no one knew me.i loved the way i was walking in my heels as my butplug was in my hole..so i final... Continue»
Posted by elamehs699 5 months ago  |  Categories: BDSM, Group Sex, Shemales  |  Views: 262  |  
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Mexican Boy Meets American Boy

My name is Enrique and I am from Chihuahua Mexico. Since a c***d I never really liked girls, but I didn’t seem to like boys either. That was true until I first went to visit the USA. I fell in love when I met a white American boy. His beautiful blue eyes, his pretty smile, his perfect body, and his tall frame attracted me to him. I never met a man like that in my life. I was 18 and he was about 23 years old. I didn’t know much English so it was hard to talk to him. But he knew I wanted him.

He lived in a Mexican neighborhood in San Antonio, Texas, and was dating my cousin Maria at the time... Continue»
Posted by wdl88 5 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 1855  |  
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My Neighbours surprise

It had been too long, far too long since I last dressed up. I am a cross dresser with Sub and Dom tendencies but unfortunately my partner does not like me being a Gurl and so I have to when I can sneak in a dressing up session to fulfil my needs.
I hadn't dressed up for over a year and was itching to feel the touch of my nylons next to my skin. My partner was going out to meet up with a friend which was to be an overnight visit which meant I was to be on my own.... "What should I do" I thought to myself, "watch a film, play on my Xbox?"
No I thought "I'm going to pamper myself and get doll... Continue»
Posted by maria2904 5 months ago  |  Categories: Anal, Shemales  |  Views: 3044  |  
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My sexy filipino tgirl slut


A story about how a sexy crossdressing filipino slut slowly seduced a straight guy..........


Sorry this story is quite long
But true

Well it was about 2 years ago now i was living in london, im 30 yrs old and normal straight guy , love football and sexy girls, love working out and am very muscular. I was looking for a new place to live as i had found a new job in a different area of london, it was quite stressfull i went and saw many properties , flats, houses,u name it i went and checked out so many but either i couldnt afford the rent or i didnt like the place. Anyway i finally d... Continue»
Posted by Daddybeefy 5 months ago  |  Categories: Shemales  |  Views: 1613  |  
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Not a sex story, just one bad experience (would lo

As i am a crossdresser on the closet, the most common place to look for sex meetings is on internet sites and forums. One of the main problems on that type of "researh" has to do with the posted pictures. Most of them are fake resulting not so happy experiences. Usually i do not judge people from their looks and i consider attractive most of them. Some have nice bodies, others are funny and/or clever. But when you chat with someone and arrange to meet you expect that the data he is providing you would be the real ones, after all what's the point of hiding them one day before meeting?
Imagine... Continue»
Posted by georgette32hk 5 months ago  |  Categories: Gay Male, Shemales  |  Views: 706  |  
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FUCKING UNCLE BOBBY

The title of this story isn't really accurate as I wasn't fucking Uncle Bobby see Uncle Bobby was fucking me! He wasn't really my uncle he was just my mother's boyfriend but he lived with us so it was kind of like he was my Dad I really like him a lot he gave me lots of attention and took me places and gave me money for doing chores for him he really was a good guy! He had a boat and it was a nice one too he kept it docked at the Marina and one weekend he asked me if I wanted to go fishing with him well I loved to fish and I loved boats so hell yes was my response and we set out to go fishi... Continue»
Posted by laceysgirl 5 months ago  |  Categories: BDSM, First Time, Shemales  |  Views: 6707  |  
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Tranny Attack Ch. 02


"You'll be hearing from me again, sweety!" With those words Julia had kicked me out of her apartment.

I dragged by bruised and ass-fucked body home. Thankfully, Jane was not back as yet. All through the journey back to my house images of the previous night kept playing through my head. Discovering Julia's cock, of being tied up and buggered, of sucking her cock, and of having Julia piss on me. And it was all on camera! And who had she sent the videos to? If she blackmailed me, what would I do. I could pay her off quietly, since we were a traditional household and Jane never said anything ... Continue»
Posted by bi_hengst 5 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  Views: 1577  |  
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My Shemale Stepmother

My parents split up when I was eighteen, I was a little distressed by it but we had never been as close as some. Still, I didn't really see what had driven them apart so quickly and so thoroughly that they never even spoke any more. I guessed maybe one of them must have had an affair and that was really all that I thought about it. I went off to college and life went on. That following summer, when I was nineteen, I moved in to live with my dad for the summer. He had bounced back quickly following the divorce and had already found someone new and I had to say, he had done pretty well for himse... Continue»
Posted by bi_hengst 5 months ago  |  Categories: Shemales  |  Views: 4805  |  
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Tranny Attack

Tears of pain pricked my eyes as Julia drove her huge black cock into my ass. In my wildest dreams I had never expected myself, an all-American straight white male to be in this situation, beaten, bound, and being ass-fucked by a transsexual with a huge cock.

I am a normal sort of person, happily married, with two k**s, and with normal middle-class values and behaviour. I don't hate gays or blacks or anything like that but I don't want them in my neighbourhood. My only fault is that I cheat on my wife a lot, but heck, I'm a normal guy and have needs. However, I would be really mad if Jane e... Continue»
Posted by bi_hengst 5 months ago  |  Categories: First Time, Shemales  |  Views: 877  |  
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Career Path

“Welcome, Jordan,” smiled the middle-aged white man. “We’re real excited to have you on the team here at Wyatt Motors.”
“Thank you, Mr. Phillips! I’m happy to be here too.”
“Please…Call me Jim,” the finance manager informed him.
“Alright, Jim!”
“Let me show you to your desk so you can put your things down and then I’ll introduce you to everyone.”

Jordan sat down and dug a four photo frames out of his messenger bag. He set them up to his liking. He was the new senior accounting clerk for the successful used-car dealership. He adjusted his Stafford brand charcoal and red gingham tie as he... Continue»
Posted by faggyboi 5 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  Views: 1694  |  
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