Shemales Porn Stories
Page 59

Married to a hot and horny redhead

My wife, what can I say she is tall and leggy with thick, natural wavey orange red head with beautiful porceline skin and just enough freckles to tell you she is a ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen.
From the time we started dating my friends all expressed their envy at me landing such a smoking hot piece of ass. She is a freelance writer for fashion magazines and on-line blogs so she is pretty dressed up where ever she goes.
I got home one Friday evening from an afternoon shift. I knew she was home because ... Continue»
Posted by triphammer73 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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my office mate screwed me up (part 2)

Early morning Aralu called me, hey where are you baby? At home coz I was in a deep pain so needed to take care of myself, I replied. Ha ha ha I hope I didn’t heart you much, but little pain adds lots of fun ya? He asked. Ya you are right. I wrapped up conversation nicely,
I was nervous whether Aralu is going to recognize me that I was the one who slept with him last night? Probably not as I was fully dressed with makeup & accessories and he was d***k. Just to give an impression to him that “keep it confidential even if you recognized me” I posted on my hookup profile “last night I had a tri... Continue»
Posted by royalraand 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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The Transformation

I woke up in a daze. It had been a night of drinking and all I could remember was everything eventually getting fuzzy. My head was spinning but that was the norm after a friday night "study night" with my friends. Most everyone was out of town but I had still gotten a ride over to my friends apartment. Anna and Heather's place, Anna is a tall redhead. She has lovely pale skin and a bigger build. Not fat just broad shoulders, massive tits, and a fitting frame. She never looked fat just healthy, always in good physical condition. Although she made me look ridiculous. I'm scrawny and 5'1... Continue»
Posted by fictiong 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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What Happens In Vegas! (copy, I wish i was able to

Hi there! I'm Ann. I would like to share a true lifestyle story with you that has been permanently embedded in my memory and makes me cum every time I think of it!
Let me begin by giving you a bit of background about my husband, (Tony), and my swinging history. Tony and I are a happily married couple living in Las Vegas and have been in the lifestyle for over 15 years now. We have certainly enjoyed our adventures over the years and have brought every fantasy we have had to reality. Living in Las Vegas, we enjoy the fact that we have a constant source of play mates in the large number of tour... Continue»
Posted by pervert76 1 year ago  |  Categories: Hardcore, Shemales, Taboo  |  
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Ladyboys: Moving to Thailand and my first Ladyboy


After living in the Netherlands for 33 years I was ready for a big change. I had been toying with
the idea of moving to another country to get away from the stress of it all for a while.
I had girlfriends in the Netherlands. Wives.
I had one nighters and 2 nighters. I wasn't doing bad for myself.
But, there was something missing on the girl side. I love variety. I think I've been with
every kind of girl I COULD be with in the Netherlands. I started thinking about other countries.
Other girls. Other types of girls...
I had seen shemales in Amsterdam. Emphasis on the boy part. And they ... Continue»
Posted by casinocock 1 year ago  |  Categories: First Time, Shemales  |  
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Shopping

I have lately come to terms that I like to cross dress and want to explore it more. Thanks to one of my friends on here who has encouraged me I am taking that next step. I have never really told anybody else about what I do. I had to go out of town for a few days on business and decided to take my clothes so I could dress and go out in public some. I figured I would do it there so in case I didn't pass well it would be in another town.

Well yesterday I got through calling on one customer and had some time to kill before a 4:00 appointment with another customer. I decided to swing by a... Continue»
Posted by KellyCost 1 year ago  |  Categories: First Time, Shemales  |  
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Karaoke With A Sexy Twist

For over 10 years I have been doing karaoke shows at local bars, restaurants and a shit load of private parties. They are usually the same scenario, set up, play karaoke music for 3-4 hours then breakdown, pack up and go home. At one bar I play at I have quite a few “regulars” who I have gotten to know. Two girls, s****rs, are in that group and they always sing duets together. They are quite good and also nice on the eyes. The shorter one isn’t as “chesty” as the tall one but she is more petite overall, which I do like. Quite honestly I’d do either one of them if I had a chance. About ... Continue»
Posted by bigsoftee 1 year ago  |  Categories: First Time, Hardcore, Shemales  |  
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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 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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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 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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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 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
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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 1 year ago  |  Categories: Anal, Shemales  |  
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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 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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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 1 year ago  |  Categories: Group Sex, Shemales  |  
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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 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 1 year ago  |  Categories: Hardcore, Masturbation, Shemales  |  
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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 1 year ago  |  Categories: Anal, BDSM, Shemales  |  
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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 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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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 1 year ago  |  Categories: BDSM, Group Sex, Shemales  |  
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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 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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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 1 year ago  |  Categories: Anal, Shemales  |  
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