Shemales Porn Stories
Page 63

The Hotel Part 1

I knew when this started it would be like nothing I had ever done before. I drove up to the hotel early friday morning. I was checking in for seven days.
Seven Days of non stop pounding of my asshole, Strapons, Crossdressing, f***ed fem, huge dildos, and giant buttplugs are just a few of my fetishes, and I expected every fantasy to be fulfilled this week.
As I pulled up under the awning of the front enterance I was met by a woman in a French Maid uniform. I introduced myself, and said I was checking in fo rthe week. She smiled, as she opened my car door, helped me out of the car, took my ba... Continue»
Posted by NJStraponLover 2 years ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1335  |  
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Daddy's Popper Challenge

Since I've been enjoying the users’ stories here so much I thought I'd share one.
I'm a pretty good looking guy, love girls and pussy, but I am a closet tranny chasers. I love hooking up with crossdressers and transgender. I dressed a little in high school and college; I left behind the clothes but not the lust for the femme bois.

Last week when work was tough I needed a five minute distraction to clear my head so I called up Craigslist and browsed the Casual Encounters T4M. This was around 2:00 in the afternoon, a very hit and miss time. The ad that peaked my interest was "Mature Crossd... Continue»
Posted by gypsy61 1 year ago  |  Categories: Mature, Shemales  |  Views: 1334  |  
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An evening out.

I've been a particularly horny little girl for a few weeks now. When trying to just score a quick hook-up I have went all the ways of our wonderful age of civilization. Everything from dating sites, hook-up sites, and even craig's list. After a few weeks of just not being able to set anything up I decided to go hit up a club and see if i could find someone fun that might want to play.

I got dressed up in a sexy little outfit (fishnet thigh highs, black cheeky panties, black bra, fishnet shirt, little vinyl skirt and a pair of knee high boots) I did my make-up, fixed my hair nice, and jumpe... Continue»
Posted by bellaleroux 11 months ago  |  Categories: Anal, Group Sex, Shemales  |  Views: 1332  |  
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The unusual girl...and boy: part 3

Pt3:
Saturday night seemed to last for ever and I couldn't sle3p for hours since I had just found out what it felt like to play with my butt hole when I was in the shower. My loneliness continued Sunday morning until I finally called her in towards the afternoon. When Sam picked up the phone and I heard her voice say hello, the first words that came out of my mouth were, "I'm sorry for doubting you Sam! It's okay with me, now we can do things how ever you want but please don't be mad at me!" She said, "You mean...you're fine with doing it my way?" I quickly confirmed it saying, "Yes! It reall... Continue»
Posted by adblman 4 months ago  |  Categories: Anal, First Time, Shemales  |  Views: 1333  |  
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Part 1.. An Idea forms

My plan was pretty simple really… Find a fem-boi looking for a Sugar Daddy and change him to a her over a period of time… Simple in theory, Much harder then it would seem in reality. Being in my mid-40’s and rather well off from a few investments and a wealthy grand-mother I had plenty of time to indulge my more twisted desires. I got into Trans-Sexual porn a few years ago and I was hooked almost immediately. I do not think I am actually gay because the thought of ass fucking a man does nothing for me.. But on the other hand if that man had very feminine features, a small quiet voice, creamy ... Continue»
Posted by Azmodaz 1 year ago  |  Categories: Group Sex, Shemales, Taboo  |  Views: 1331  |  
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Our First Time

I take my hand a gently begin caressing the ever increasing bulge in your pants while tenderly kissing your neck. I push you onto the bed and crawl up to you and begin to unzip your pants. I take my hand and grasp your rock hard shaft and begin to stroke you. I can feel you get harder in my hand. I stroke you faster and faster until you almost can't handle it, I stop. I pull your pants off and your shorts and begin storking again. I open my mouth and wrap my juicy red lips around you and begin to play with your head with my tongue. My other hand begins playing with your sack, massaging and twi... Continue»
Posted by uatu40 2 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1330  |  
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Chrissie's High School Reunion

Chrissie’s High School Reunion

When the announcement arrived in the mail notifying Kelly and I that our High School graduating class was organizing a ten year reunion we spent that entire evening discussing the pros and cons of attending. I was fairly certain that I wasn’t interesting in attending but Kelly insisting on listing all the reasons why she felt we should attend.
She was interested in going because she wanted to make passes at all the “stuck-up bitches” that pissed her off in high school. She said it would be fun to hit on these girls in front of their husbands or boyfriends. S... Continue»
Posted by chrissieCD 2 years ago  |  Categories: Anal, Shemales  |  Views: 1330  |  
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Xdresser Housewife Roxys daily chores while wife i

Well the best fuck I've ever had and continue to have all started when we intalled a pool in our back yard .Once the pool was in the pool shop sent over a young guy to set up the pump and show us how to use it ,as it was a Saturday my wife was home and she was in a bikini looking very hot. Well in walks this 6"5 very toned very sexy black guy ,when I say sexy he is the sexiest guy I've laid my eyes on and the body his arms were huge ,not one ounce of fat ,man the thoughts going through my head were insane but the one thing I knew is I had to have him 100% I would do everything I could to get t... Continue»
Posted by foxxiroxxi 2 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  Views: 1330  |  
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A Special Girl - Prologue

A Special Girl - Prologue

By Alhana Escher


James was nervous. Alice would be arriving soon and he had a feeling that their relationship could be moving onto the next stage that night. He and Alice had been friends for years, and he had fancied her for most of them. He could still barely believe that they had been seeing each other for the last few months. He could still remember staring at her in school. She looked so sexy in her uniform. That blue pleated knee length skirt, white blouse and blue blazer. The way her socks came to just above her knees, leaving just a littl... Continue»
Posted by AlhanaCD 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 1330  |  
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Becoming Bernard's Wife

This is somewhat a true story….

*************

I put an ad on Adult Friend Finder, thinking I'm never going to meet anyone here but was I wrong.

I am in my 30's, tall and slender, long brown hair and practically hairless everywhere else on my body. I was looking for whatever and was very curious. Just out of a relationship with a woman for 8 years. I moved to Europe and discretely started to experiment with guys and transexuals. It was one tranny who I was fucking occasionally said, next time, "I will dress you like a girl and fuck your hole." Sure enough, the next time we had a booty... Continue»
Posted by pat4tights 2 years ago  |  Categories: Shemales  |  Views: 1327  |  
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Something in my drink, the captive part 3

read part 1&2 first



So Tara had just let me fuck her..and just as we had started to catch our breath Anna, stormed in yelling "WHAT THE FUCK?" And as I turn around I see Anna standing there with another Tranny..I never caught her name, she was like 6'4 and Mexican..I never heard her speak any english..Anna walks over and slaps me in the face and locks me back in chains, and drags Tara out of the room, I assumed to chew her out.While they were out of the room, this big latin tranny pulled out her cock, and smiled at me..I gulped..this thing was over 11 inches, she walks over and start... Continue»
Posted by smonkeys32 3 years ago  |  Categories: Anal, BDSM, Shemales  |  Views: 1327  |  
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The strange day that left me beging for more

I was at work it a friday so I get to have a break from work after i go home anyways i was on my pc at in my offices and i called my secatary in for my papes it was late so there wasnt meny people there when she cam in i notesed that shewasnt my usal secatary she was beautayfull she had big tits double ds or big i mean these wure big tits an she hade a nice round booty and nice thick strong legs she had a tight skirt on and nice work shirt she said katie called in sick im here to fill in is tere any thing special u need i said im not sure she sad let me know ill give it to u any thing dont be ... Continue»
Posted by gothicslave 2 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1324  |  
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Just Another Sunday Funday

So I just got back from one of my favorite days: Sunday. Most people hate it because it's the day people go to church. But that's exactly why I like it. You see, every Sunday, one of my oldest and dearest lovers invites me to his home while his wife is at church. He also invites several of his friends…who invite their friends…and who invite their friends ;-) We call it "Sunday Funday".

While I usually travel very discretely, these men want me in full drag, in the sluttiest outfits and highest heels imaginable. This time, I was wearing a cowgirl outfit with a brown pair of boots, comp... Continue»
Posted by cdsexslut 1 year ago  |  Categories: Group Sex, Hardcore, Shemales  |  Views: 1324  |  
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The Day that Kelli Appeared.


One day when I was still at School (6th form), my Mum and Dad said they
we're going to my aunties for a long Weekend. Leaving on Thursday and
returning Sunday and I would be left at home.

Suddenly in a moment of brilliance an idea flashed through my head I
could spend the whole weekend Dressed (I had been cross-dressing as long
as I could remember)

Thursday couldn't come fast enough, I raced home from School in
anticipation. After having Dinner My parents asked if I was sure I would
be ok, I said yeah no problem as I have lots of home work.

After about 10 mins off they went, a... Continue»
Posted by kellianntv 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 1324  |  
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Tgirls

Shemale, tranny or as some like calling them t-girls, I like them. Im not talking cross dressers, I'm talking about the ones with titties, curves and sound like a woman. Being a bi male, to me its the best of both worlds. I like watching porn of them and honestly I prefer the ones of them doing a strip tease, ending with them stroking their cock and cumming all over themselves. 
I met one, unknowingly, once while playing around on a chat site. I was cruising thru the members "online" when I came across her profile where she had a good  picture of herself.  I sent her an Instant message and af... Continue»
Posted by rogue-1966 3 years ago  |  Categories: Fetish, Mature, Shemales  |  Views: 1321  |  
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Charlie s****r-Boy seduced by Old Fisherman

Hi, Dee. We have similar turn-ons.

I was very young, when I opened up a dresser drawer and saw a small pair of white panties laying on top of everything!

My Dads work friend and His daughter had just stayed the night. She was My age. It was Her panties! Daddy, His friend and the girl slept in one bed and Sharlee and Me slept together, in another room. The Men tried to keep the girl quiet, but She was Young and Willing to be taught 'special' things when Her Daddy shared Her with each of His friends on the weekends. She liked to giggle, I know that!

Anyway, I looked up and down the hal... Continue»
Posted by sharleesisterboy 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 1321  |  
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My girlie fantasy part 2

A few days passed since my heavenly Halloween night with the wondrous morning after & I was so excited at the possibility of meeting up with the stud that took me like a woman again. Since I knew Halloween wasn't for another year I invested in a new outfit so to meet him in. I returned to the bar one week afterwards but he never showed, though several men hit on me I never entertained them at all. The bartender wasn't the same so I never asked if they knew my hunk or not. Disappointed I went home but was motivated to keep trying. Realizing I only had one new outfit I went shopping the ne... Continue»
Posted by multiplierx 9 days ago  |  Categories: Anal, Fetish, Shemales  |  Views: 1331  |  
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The unexpected always happens

I came into school wearing a pair of my s****r’s panties in the morning under my school uniform purely because it felt great. Plus I knew I was getting away with something, wearing soft female underwear when all the rest of the boys at school had no idea. I slipped on the white lacy tangas as soon as I got out of the shower, and it felt so good as I moved them up my shaved legs and over my ass. I made sure they were tight and snug as could be before sighing in pleasure. I checked my bubble butt out in the mirror, raising my arms and doing a little shake. I laughed at myself, slapping a butt ch... Continue»
Posted by cocksucker1966 8 months ago  |  Categories: Shemales  |  Views: 1322  |  
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Becomming a Sissy Slut

Sandy's Life
My name is Sandy Johnson. I chose that name 35 years ago because I like Sandy and I knew a hot female with the last name Johnson. I first remember finding my mothers underclothes in the bathroom closet. We she and my Dad would go out I could go in the bathroom and put her slip on and find a pair of dirty panties in the dirty clothes hamper. I still love the feeling of an old fashion girdle!

I dated in HS and went to college, married, went to war, had c***dren, divorced, married again and divorced again. All this time I kept buying women's clothes and... Continue»
Posted by sandynccd 3 years ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 1317  |  
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Friends

Another story off the web. Enjoy

i have been friends with my next door neighbor for about 5 years now. he recently divorced his wife, but somehow managed to keep the house. So, we have been doing the bachelor thing together for the last few months... beer and cookouts on sundays while watching football, getting d***k, fixing cars, etc. my wife complains a little about this, but all in all, she puts up with it. she uses the weekends to visit her s****r (who is ill) and go out with the girls. i definitely make it up to her, above and beyond.

yesterday, our typical group of friends was una... Continue»
Posted by BeeJay69 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 1316  |  
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