Shemales Porn Stories
Page 122

Planet of the Gigantic Schlongs

Planet of the Gigantic schlongs

By The Iceman

It all began in a place not too long ago but in a faraway
place. There was a planet way out of the galaxy
that no researcher ever discovered and most likely
never will be. The story begins on a planet called
Weenus. Nobody knows how the planet got
its name. Perhaps we’ll never know…..

Although not very much is known about the history of the planet Weenus, there was something very unique about it. There was no war, pollution, crime or poverty that existed in any form. The inhabitants lived peacefully. But what was so unique about t... Continue»
Posted by icemanrisen 4 years ago  |  Categories: Sex Humor, Shemales  |  
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A night with Rebecca

My heart was beating fast as Rebecca answered the door and invited me in. After months of swapping photos and chatting the moment had arrived. I was floored by how much more sexier she was than the photos we had been exchanging. My cock instantly became enraged as I stared at her. Rebecca had the cutest cheeks and eyes and she new how to do her makeup to accentuate her beauty. She wore a nice shoulder length brown wig. She had on a nice layer of foundation, her eyebrows painted dark. Eye lashes thick and full with eyeliner and sexy eye shadow under and around her eyes. Her full lips painted ... Continue»
Posted by Zeffer1 4 years ago  |  Categories: Shemales  |  
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Awakened by Candy

It was a Saturday and I was just strolling down the High Street, going nowhere in particular, when I noticed a commotion down a side alley. A largish male was pushing two girls around; they both looked pretty distressed. I grabbed the bloke as he slammed one of the girls into a door, and he went arse-over into the road, got up and took a swing at me. I dodged, and gifted him a right hook; his nose took the brunt and spurted bl**d instantaneously. He thought about coming again, but the bl**d was pouring from his nostrils; he staggered off, thinking better of it.

The two girls were a litt... Continue»
Posted by midsummerman 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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T-Girl University

Not my story, author is unknown to me, but sharing it for all to enjoy.

T-Girl University

Jason was apprehensive about starting college, as any freshman would be. His high school girlfriend, Becky, whom he loved dearly, was going to a different college on the opposite side of the country. They had to promised to stay together but Jason was worried; there would be a lot of temptation for her from all those west-coast surfer dudes. He hoped she wouldn’t forget him and made a vow to himself to stay faithful no matter what. But there would plenty of temptation for him as well: Jason was goi... Continue»
Posted by eurotarzan 1 year ago  |  Categories: Anal, Group Sex, Shemales  |  
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First Encounter With A Ladyboy

A couple weeks ago I met this fine girl walking down the beach. Looked a little asian, but maybe she was one of those latina aztec chicks that just look asian. I go up and talk to her, shes got a really sweet voice, tells me her name is Jazz. I start talking with her about where she lives. Tells me she lives a couple blocks away and she tans all day long next to her pool. I look at her.. and damn shes right, cuz she has a really nice golden tan. I ask her "well why are you at the beach? "Cuz Im tired of tanning and not showing off my body to anyone!" I say, "oh well that definitely makes sense... Continue»
Posted by bnrslyr 3 years ago  |  Categories: Anal, Shemales  |  
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My firs time as a crossdrese

Hi,i am 19 and i have always liked wearing womens clothes.While wearin them i always imagined there was a nice older guy fucking me and cumming on my face. After a while i decided to try my fantasy for real. I got in contact with an older men and we decided to met. He said that he would come for me in a car and that we will go to his house and have a lot of fun. I was so nervous and could hardly wait to meet him. The next day i was waiting for him at a spot where we arranged to meet. He came in his big black suv and opened the door and said to get in. I got in and sat next to him. He had dark... Continue»
Posted by nikoletakurva 5 years ago  |  Categories: First Time, Mature, Shemales  |  
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Teen Cross dressers First Man.

This is a true story that happened to me only a few monthe ago.

I just moved to a new town, I was an average 18yo male about 5'8 lean and athletic with a few female relationships before. I started to do a little bit of discreet cross dressing in my house about a year ago and thought about how great it would be to hook up with a shemale. I never thought it would happen of course, I didn't know where that stuff happened and I was always really shy.

One Friday after a grueling 4 hour study session at school one of my classmates, who I didn't know very well, invited me to have a few drinks... Continue»
Posted by ClaireCD 5 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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old tom part 2

part one of this story was how I was introduced to my new dressing friend by an of chance meeting at another friends house who as I am aware at this time does not know of mine or old toms sexual preferances.

As I ventured into the room to my right there was an airer on the left wall a dressing table just past that with various array of make up items, to the right as you go in there was a bed made up with an eiderdown over the top, but on the far away wall was a wardrobe which was the object of my desire I hope.

On opening the wardrobe the items of female atire was fantastic with slips,kn... Continue»
Posted by natasha1975 3 years ago  |  Categories: Gay Male, Shemales  |  
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she had a COCK bigger than mine ..oh my !

this is no B.S ,no fantasy, no make belief, no fairy tale,.. this is a TRUE STORY and an ACTUAL EVENT.

iv always been a very observant k** growing up always trying to find the unseen and overlooked things in life i guess you can say curious....how curious ??:] well...

there was this older lady who il call Ms.Auburn who lived in the neighborhood that everybody knew,especially the men because she was a tall long legged brazilian chick with a pair of double D's that you couldnt possibly overlook and she would always come out on her steps with a short tight satin auburn coloured housecoat a... Continue»
Posted by jerkme 4 years ago  |  Categories: Fetish, First Time, Shemales  |  
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My wife introduces me to submission and cuckoldry.

It took me a while to come clean to my wife about my time before we met. In that time i had been a submissive to a Professional Mistress in the Midlands and it was from her that i developed an interest in both servitude and crossdressing. Mistress/Madam had always insisted that i should be dressed as a woman whenever i was in her presence. After Mistress/Madam and i had gone our separate ways after many years of being together i had to admit to feeling a little alone and deserted and with no direction in my life. i had several relationships and none of them had any idea about what i had been ... Continue»
Posted by oldognewtrix 6 months ago  |  Categories: BDSM, Mature, Shemales  |  
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Trapped and Trained Sissy Ch. 05

Trapped and Trained Ch. 05
There I was, Saturday morning, back in the driveway of my quote/unquote "Master", as he liked to call himself. I turned off the key to the ignition of my car and prepared to step out. He had sent me an email the previous night telling me to show up in the outfit that I had left in during our last session.

I looked down at myself and shivered as I saw the short edge of my form fitting black dress riding up to where I could already see the tip of my black chastity belt peaking out from underneath. That belt had been absolute hell for me the past 36 hours or so. It... Continue»
Posted by hpm12 2 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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First time in Bangkok

If you have read my story about the first time I was with a TS girl then you know my experience was limited to just a few times. So about 4 years ago I went to Thailand to visit my buddy who was working there in a high profile job with the Thai government. We stayed in his apartment on the 40th floor of a 5 star hotel in Bangkok, which was pretty nice. I had just turned 39 and was looking forward to my first visit to Thailand and seeing my friend I had not seen in 4 years.

Now, I have travelled very much in Asia: PI, Hong Kong, Tokyo, Singapore, pacific islands, and Hawaii, but not Thai... Continue»
Posted by mahuluvr 5 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Theater gangbang of cockslut Kitty


I drove to the old-and-rotten-unofficially-turned-adult-theater that I had been too before, parked and headed in. I walked in, went to the counter to pay and the clerk gave me a once over.

"Ladies are free on Friday nights," he said.

Did I really pull off the appearance of a girl? "Oh, I'm not really a girl," I said, not wanting to cheat the establishment out of revenue.

"Hot stuff, you are close enough for my tastes," he said with a dashing smile. "Have fun up there." He then winked at me.

He was a cute boy, maybe mid-twenties, tattoos, and hoop piercings in his ears that stretc... Continue»
Posted by CumLovingKitty 9 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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Back to the shitty date which ended up not so shit

I straddled Ron, the black hung stallion and impaled myself on that huge cock. I slid the whole length of that massive shaft swallowed that shit up, til I felt it in my lungs. It must have felt good because his eyes got all googly watching me take that black dick all the up inside me! It felt soo deep pulsating inside me!

then WTF? Andre, starts to straddle his face and get rimmed by Ron! I knew these fuckers were fags, and that really fucking turn me on! Not because I'm into gay sex or anything. Just into the possibilities it presents!!!! I start to grab his balls and stroke dre's ... Continue»
Posted by sataori_fukame 3 years ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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How I Became a Tranny Whore

First time as a Tranny whore!

When I was 30 with c***dren at home I would get dressed in the bedroom. When it was time to leave the wife would take the c***dren off for ice cream and as soon as they were out of the drive way I would head for my car. Of course when I returned home the c***dren would be a sl**p. The plan worked for years. The wife had it much easier. She would get dressed for a night out with the girls, and then meet her boy toys for a night of fucking.
On this night I wore a black lacy bra, black rubber thong panties (they always hide my package so well), tan thigh hi... Continue»
Posted by littleoralvee 4 years ago  |  Categories: Shemales  |  
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Thailand Part 2

I woke up after the wank session hearing somebody in the apartment making coffee, I got up in my underpants and found my friends wife in her Brazilian type bikini behind the counter making coffee. This bikini did not cover up much and her heavy tits were just covered while her arse and cunt was split by a string. I could see her pussy lips spread by the string and I had the starting of a boner.

After coffee we went down to the pool and managed to get a couple of sun beds by the pool, she asked if I would rub lotion on her back and I worked my way from her shoulders, down her back to her bum... Continue»
Posted by daveaverage 1 year ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Mel and me in rochester!!

The musical orchestra Mel and i are in had a performance in Rochester ,New York and i needed someone to share a room with at hotel. Mel was the first person who came to mind,and since blowing him last time i thought i would ask him. Mel told me his wife wouldn"t be going and he would love to share a room with me!! Friday morning we had to meet bus in Burlington,Ontario early so when i got up i showered and gave myself an enema so i would be so clean for Mel.My toes were painted bright red and i was shaven clean except for groin region and man-pussy!When i arrived at bus Mel had saved me a seat... Continue»
Posted by bashunia 4 years ago  |  Categories: Fetish, Mature, Shemales  |  
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My First Time With Paul

Paul & I had been chatting on a very popular web site's chat room. He was in Glasgow on business and was one of the rather more fit looking guys who wasn't embarrased to show his face on his profile. I was later to find, his body & manhood were equally as yummy.

We arranged for him to pop round to my comfortable flat in the city centre, confirmed by text & then phone so it was off to get ready for my sexy date.

I showered, got dressed in some nice black lingerie - bra, panties & suspender belt I opened a pack of new sheer black stockings & slid them up each smooth leg, clipped onto the 6... Continue»
Posted by Caz_TGirl 3 years ago  |  Categories: Anal, Shemales  |  
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Sweet Charity

You may have heard of the phrase sweet charity, well in my case it was certainly sweet to me. I have built up a large part of my CD wardrobe through judicious visits to charity shops wherever I may be in the country. In one of my local charity shops there's an assistant called Wendy who I would judge is in her mid fifties but looking well on it. She's always well turned out in neat blouses, always a just above the knee skirt, never bare legs and 3 to 4 inch heels of various kinds. I must admit that my fairly frequent visits to this particular shop engender a feeling of hornyness on two counts.... Continue»
Posted by MichaelaCD 4 years ago  |  Categories: Shemales  |  
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Curiosity Part I

“Alright, Jason, that concludes your orientation. You can go ahead and get started,” said the chic manager of the retail clothing store that catered to juniors.
“Thanks, Melanie! I’ll talk to you soon.”

Shortly after she disappeared Jason was walking the perimeter of the store performing his security detail. Standing at just under six-feet-four-inches and weighing about two hundred forty pounds Jason Pitts, caught the attention of one of the sales associates.

“You gonna keep us safe from all the project chicks,” quizzed the short and slender chocolate employee.
“Yeah I guess. I doubt t... Continue»
Posted by faggyboi 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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