Shemales Porn Stories
Page 5

The Story of My Life - Part II

The story with Peter and Simon went on for several weeks. We were going at their place, dressing up there and had sex. In order to be able to shave our body hair me and Nick decided to join a swimming club. That way we could justify the shaving to our parents without raising any questions.
At the same time I was dating a girl with whom I have only reached foreplay. Usually I was seeing her on Fridays and Saturdays. As she had to be back home by 22:00 I had all my nights free for Simon.
I was now more experienced and I started to give him some really good blow jobs. But, this dressing issue... Continue»
Posted by georgette32hk 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 728  |  
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Memorable Nite Going Home

I remember it was late, I was meandering home after roaming thru a few bars downtown on a Saturday night That usually meant checking out one or two of the all nite Arcades hoping to maybe get lucky before reaching home. It seemed to be a slow night all around and I was about to give up and head out when I heard this woman say, "Are you looking for something baby?" I stopped in my tracks and looked into an open booth to the source of that voice. "Something like this?" There she was, Black wig, white fake pearl necklace, Black mini-skirt and white control top stockings, black three inch... Continue»
Posted by Keith_Walters 1 month ago  |  Categories: Gay Male, Shemales  |  Views: 2411  |  
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The Story of My Life - Part I


It must have been when I was 14 years old; masturbation was an exciting new thing for me. I was picturing myself with older women (at 40s or 50s) who guided me around sex. One day, I don’t know why, I thought of myself as a young girl who was invited in a woman’s house. Innocent and naive. For a long period this was my favorite fantasize. I never thought that it could be something out of the normal as I was imagining having sex with women.
About one year later, I was alone at home as my parents were both at work. For some reason I cannot recall I tried my mother’s underwear and stockings. ... Continue»
Posted by georgette32hk 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 2276  |  
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Undercover Angel Ch. 04

Undercover Angel Ch. 04 - Transvestite on run is finally caught & fucked.



Michele blinked as the flash went off in her eyes.

"Ok; one more photo, and this time keep your eyes open for me luv ok?" the man behind the camera said.

Mike had done some research before he had ripped off Tony Leonardo and he had located a man named Harold Brown who could produce good quality counterfeit identity documents. Harold had agreed to provide Michele with a passport and a driver's licence in the name of 'Michele Nylons' using a fake address. Michele was having her picture taken so that the docume... Continue»
Posted by bi_hengst 1 month ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 558  |  
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Undercover Angel Ch. 01

Undercover Angel Ch. 01 - Mike goes undercover as a transvestite to escape crime boss.

When Mike Harris stole two point seven million dollars in cash from his employer, he knew that his life had changed forever. It's one thing to steal that amount of money from your bosses' safe; it's quiet another to steal it from a ruthless gangster who is heavily involved in narcotics, prostitution, gambling and murder.

Mike was Tony Leonardo's bookkeeper, accountant and financial adviser. Far removed from the seedy side of Tony's business, Mike laundered the money, hid it in offshore accounts and inv... Continue»
Posted by bi_hengst 1 month ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 722  |  
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Undercover Angel Ch. 02

Undercover Angel Ch. 02 - TV on the run from the mob is f***ed to suck cock.


Tony Leonardo discovered that he had been robbed of two point seven million dollars by Mike Harris at ten o'clock on the 15th July; by then Mike Harris, in the guise of his alter ego, Michele Nylons, was sl**ping in a cheap motel a few hundred kilometres away, just over the Victorian border.

As soon as he discovered the money was missing from his safe Tony knew that Mike had stolen it. He didn't know whether he was more pissed off with Mike for stealing the money or for stealing his books. He knew that he co... Continue»
Posted by bi_hengst 1 month ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 792  |  
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Undercover Angel Ch. 03

Undercover Angel Ch. 03 - Transvestite in hiding f***ed to fuck.


Steve Marshall rolled into Wodonga and met with his contact; the manager of the Best Western Motel. The manager had spotted Michele's blue Ford and checked the guest register and discovered that the driver of the Ford, a 'Ms Mary Smith', was currently occupying room 113. The night clerk had described the woman to the manager; and then the manager had contacted Steve. By the time Steve Marshall arrived, things had taken an eventful turn.

"Tell mister Marshall what you saw," the manger told the night clerk.

"Dude, that c... Continue»
Posted by bi_hengst 1 month ago  |  Categories: Fetish, Mature, Shemales  |  Views: 925  |  
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Michele And The Predator Ch. 02

The Predator was satisfied with his first taste of the woman who he had bent over the kitchen table and held captive; but he was far from finished with her. The snooty bitch had been taught her first lesson for the evening; his warm issue dribbling down her stockinged legs was evidence of that. "I bet she's never been taken in the rear before," he thought to himself. He was still befuddled why she was wearing pantyhose under stockings though? Maybe she had really bad varicose veins or maybe her legs were just pale and untanned? These society bitches were all so vain about their appearances, th... Continue»
Posted by bi_hengst 1 month ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 632  |  
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Michele And The Predator Ch. 04 - The End

Michele ended up sandwiched between the Predator and the stranger who occupied the corner of the booth. She heard her subjugator murmur something about 'red' which she didn't understand. She certainly understood the implication of the next sentence that he spoke, "Look what I bought us to play with!"

Then she was f***ed to turn her face towards the Predator who kissed her and then he turned her towards the other man who also kissed her. The stranger had recently shaved and smelled of the shower he must have recently taken, and although she could taste scotch and cigarettes on his breath, sh... Continue»
Posted by bi_hengst 1 month ago  |  Categories: Fetish, Mature, Shemales  |  Views: 736  |  
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glory hole dressing

I had the night off and decided to go down the block (WeHo) to a local book/video store. I got dressed into my sexiest short skirt and slinkey top (with my latex boobs) wig,makeup and "cleaned up" below.

I walked the the store and a few jaws dropped as I slowley looked around. I picked out a small butt plug ,some lube and went to the counter and paid for my items...and asked for 5 dollars in quarters,winked at the cashier then strutted off to a booth in the back.

At first I just wanted to watch some movies,but I got so hot I placed a drop of lube on the plug and eased it in slow...POP...... Continue»
Posted by sodeep2 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 4663  |  
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Erotic Comic Orgy Series - Chapter XIV

Erotic Comic Orgy Series – Chapter XIV

“The Tranny who Banged (With) Me”, with Vic (OC) and Rory (based on a shemale art)


Rory: http://up.xhamster.com/000/029/612/654_1000.jpg


Lying on his king-sized bed, Vic tried to find something to do that Thursday night. Alone at his place, he ran around his cellphone chasing someone who could give him a good night of cuddling and fun.

He ran through his contacts, but couldn’t find someone worthy to share a bed with. Not that anyone at the list wasn’t good. It was Vic’s own reasons to find some kind of variety when bored.

“... Continue»
Posted by Victor2K 1 month ago  |  Categories: Anal, Shemales  |  Views: 437  |  
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One night I

The last time I got fucked was in may or june 2011,. in spokane, wa. I was horny and d***k in my mums apartment with no privacy,. so I got on craigslist,. and sent out a few emails to people who have posted looking for a bottom boi, or something to that extent. I got a few replies back but chose the one closest to me (just north of the fred mayer on freya) cause I didn't have a car,. and would have to hike over to meet him. luckily it was only a few blocks away.

I got to his place and waited around the back for him to come to door,. I didn't knock ,. but texted him and let him come outside ... Continue»
Posted by villelohne 1 month ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 1544  |  
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Be Careful In The Park

My God! I was going to get ****d. And the people I thought I knew, if only slightly, were going to do it. I could just make out in the dim light from the moon the members of a local street gang that were about to extend their escapades to include ****. There were six of them, a street gang I had seen around my ‘patch’.

They had never given me trouble and I thought they had me pegged as a sad old transvestite cruising for trade (which I was). They were all young, fit and no doubt full of the beer they'd obviously been drinking that evening. But I hadn't come out looking for trouble that even... Continue»
Posted by bi_hengst 1 month ago  |  Categories: Fetish, Hardcore, Shemales  |  Views: 850  |  
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Michele And The Predator

The predator peered through the bedroom window and smiled; he couldn't believe his luck. This woman was just to his taste; he felt himself begin to stiffen as his eyes devoured her; he couldn't wait until he had his hands on her. In his mind he played out the scenario that he envisaged would soon take place. His thickening member began to engorge and throb.

The predator had been terrorising the city for months; always preying on attractive, middle-aged women who lived alone. He would break into their houses and spend the night ravishing his prey until he was sated; then leave the women boun... Continue»
Posted by bi_hengst 1 month ago  |  Categories: Fetish, Shemales  |  Views: 961  |  
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Four Guys And A Shemale

My big br0ther enjoyed humiliating me when I was young.
There was this guy in school that picked on me all the
time, calling me "tits" and groping me in the hallways.
I couldn't complain because I was a known freak and
slut so I just tried to avoid him and his asshole
buddies. I was terrified of Donald and his three friends.
One Saturday morning when m0m was visiting grandma I
showered, blow dried and came down the stairs naked
because that was one of my b*****r Johnny's rules:
whenever m0m wasn't home I had to go naked or put on sheer
black stay-up nylons if he told me so that he
... Continue»
Posted by yutubeslut 1 month ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 3248  |  
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Mickie

The storm door banged. She was home and I bet she was already investigating the wonderful aromas coming from the kitchen. I was just finished the first chapter of my next book. I chuckled to myself when I felt her hands on my shoulders and the kiss on the back of my neck.

"Oh, you're off to a good start, Baby!" She purred in my ear.

My arm slipped around her waist as I turned.

"First chapter all done my love. Only twenty five more to go,"

"Well if it does as well as the last book, are you still going to take me on that vacation you promised?"

"Of course I will, my reason fo... Continue»
Posted by vosmou_vrot 1 month ago  |  Categories: First Time, Shemales  |  Views: 809  |  
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a quick story..

it was yesterday night and i was out with the lads and it was getting late and i was deciding should i stay out or go home. i then noticed a girl looking at me but in a good way. i decided to walk past and say hi,she said she had noticed me all night and she thought i was sexy..hahaha bl**dy hell that's a 1st. No don't say that you are. So i asked her why was she on her own she said her husband was away and she wanted to have a night out but nobody would go out with me so i decided to pop out and have a wine on my own.

i asked her what her name was and if she wanted another,her name was Jan... Continue»
Posted by naughtydarksecret 1 month ago  |  Categories: Anal, First Time, Shemales  |  Views: 2446  |  
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First Halloween

I have always been a skinny boy and not much muscle tone. Very feminine and so my older s****r started dressing me when we were alone at the house. I didn’t mind and most of the time I liked it because it allowed me be free. I felt more comfortable dressed as girl. Last Halloween I decided that I would let her dress me up as a girl and take me to a party of a friend of hers.
She did my makeup and fixed the wig I wore. I chose a white button up shirt and a black pleated skirt. I wore white stockings and white platform heels. The heels made butt stick out just a little. The wig I wore was red ... Continue»
Posted by CB1996 1 month ago  |  Categories: Shemales, Taboo, Voyeur  |  Views: 8254  |  
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My sister, my first, the tranny

A little something different to spice up your lives

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It was the first week of June and school was out for the summer, I was 18 and had just finished my senior year. One night while we were eating dinner, My Mom and step dad informed me that they were going away for two weeks. When they got married they did not go on a honeymoon, so they wanted to take one now. Jack, my stepdad, told me they were going to... Continue»
Posted by 6270daniel 1 month ago  |  Categories: First Time, Shemales, Taboo  |  Views: 10779  |  
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Meeting a young white guy from online (Andy) Pt.1

I had been talking to a young guy from online for about 6 months he was 23 and with me being 39 I never thought we would actually meet, he was fun to chat with and we exchange several pictures and even had ciber video sex on another sight together.
Anyway in March we both had birthdays the same month within a few days of another and he kept asking if we could finally meet and celebrate our birhdays together he was willing to come the 3 hours to meet me and after a little prodding I decided to let him after all I figured I could handle him if anything went the wrong way.
We decided to meet... Continue»
Posted by MonicaBond 1 month ago  |  Categories: Gay Male, Shemales  |  Views: 2849  |  
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