Shemales Porn Stories
Page 112

Young Master Ch. 01

It was supposed to be the best day of my life...and maybe it was, but definitely not in the way I planned.

My 21st birthday...my first day as a man, as a true lord of the Manor...my first day as a Master. I was so nervous I threw up my lunch. Not very manly, I know, but just the thought of having my very own sissy to play with had me teetering between the giddy excitement of a k** right about to open the biggest present under the tree, and the stark terror of officially being a man in my step-father's eyes...how could I measure up to him? I felt destined to disappoint him...and I didn't eve... Continue»
Posted by bi_hengst 1 year ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
1845
  |  
89%
  |  2

A First Time Out

I'd always fantasized about going out to a bar or a club, dressed as a woman, and after a few drinks managed to find the courage to do so. By the end of the bottle of wine I was dressed up and ready to go, suspenders, stockings, a corset on so tight it was hard to breathe underneath a loose, knee length skirt and close fitting top. My make up was done, a touch up of lipstick after the long black wig had been smoothed down and the last of the wine polished off.

I'm always told I look gorgeous when I dress up, but I'd never been out before. Before it had just been for other people in private,... Continue»
Posted by amylee-jones 7 months ago  |  Categories: First Time, Shemales  |  
1378
  |  
89%
  |  1

I slept with Joanne, who had a dark secret

What is the weirdest sex I have had, I thought about is for all of thirty seconds, the night Joanne slipped inside me, on a f***ed stopover.
Now before you cry Lesbian or Bi-Sexual, you would be wrong, because Joanne was neither, she was a transsexual, something I did not know at the time, nor was she, him about to admit to, especially since I had offered to share my hotel room and not leave her stranded without.
We both worked for the same airline, which I shall not mention, due to legal obligations, but I knew Joanne from our first meeting her on a photo shoot, which was an advertisement a... Continue»
Posted by MarieL 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  
2207
  |  
89%
  |  9

Bar trap

Bar trap
By slut michelle

Steven was a dead-normal guy. At the age of 28, he felt very happy.
Everything had developed in the last few years like he always wanted it
to be. His job in a big insurance company was secure with an outlook of
a promotion in the next year. His partner, Nancy, was a very ambitious
lawyer. That meant some days with long working hours for her. But as
Steven was quite proud of her, being so successful in her job, and
because they still had enough time for each other left, he didn't
complain. Steven met Nancy shortly after both of them had left Uni. It
wasn't... Continue»
Posted by trans_michelle 3 years ago  |  Categories: Anal, BDSM, Shemales  |  
1267
  |  
89%
  |  5

The experiment

I'll admit that I was a little bit d***k when she sat down beside me at the hotel bar.

Another business trip, away from home, this was getting to be a drag, and sipping on some bourbon helped a little. The smell of her perfume as she sat down snapped me out of my haze, and I looked at her. She smiled, turned to the bartender and ordered a drink. Looking back at me, she said "Can I freshen your's up too, darling?" I must have looked like an idiot, staring dumbfounded at her. I looked down at my glass, then back to her and said "sure." Her voice was surprisingly deep, but she was pretty. I ... Continue»
Posted by abend 4 years ago  |  Categories: Anal, Fetish, Shemales  |  
2141
  |  
89%
  |  5

I am such a slut........7

I am such a slut........7


I couldnt believe that this was happening. I was so excited that I was shaking. I could hardly breathe. My first, my first real date dressed as a woman. I had met him over the internet on craigslist. We had talked. Exchanged pictures. And tonight, tonight was the night. I had checked into the hotel around five and began preparing. I laid my clothes out on the bed. My white panties trimmed in lace and my white thigh highs. My four inche white heels, open toed that would show off my pedicure and my pink toenail polish. A white lacy bra to push up my small breasts... Continue»
Posted by snuggle11 4 years ago  |  Categories: Fetish, Gay Male, Shemales  |  
1798
  |  
89%
  |  7

Something more to her, part 1

Something more to her, part 1


jasmine had just left the local club and was walking to her favorit street corner. jasmine had an IV league education, was extremely beautifull, having dark tanned skin, having 34 DD breasts, a perfect figure, and perfectly done honey blonde hair. she was smart, sexy, and she was one of the most charming people she knew. so why was she selling herself on a street corner? the reason was simply becuase it pleased her as much as it pleased her customers. she may have convinced herself it was becuase she couldnt find a man that would except her 10 inch "secret" t... Continue»
Posted by mj2397 3 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
805
  |  
89%
  |  1

My day with Maggie

I kissed my wife jumped in the car. As I turned out of the driveway I dialed in work and called in sick for the day. As I drove to Maggie's I could feel my rock hard cock beg for relief. I tried not to think about it but my cock stayed hard the entire drive. As I pulled into the hotel and walked to the room number she had text me I felt nervous, excited and so horny all at the same time. No matter how many times we have sneak off together I always feel the same. Maggie opened the door and I quickly slid into the room put my arms around her as our lips touched. The kissing turned to passion as ... Continue»
Posted by iheartm2f 10 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
3593
  |  
89%
  |  3

The Politics of Dancing

"What the fuck are we doing here. Seriously?" I growled in his ear. I was still smiling, and I doubt anyone was going to be lip reading.

We were on the dance floor, my arms around his neck, slowly swaying to a crappy Lawrence Welk-wanna be band.

"You know what we're doing here, darling." His reply was sugar coated, sappy with his big grin. And why shouldn't he be smiling. He was dancing with the most beautiful woman in the place. The men were obviously jealous of his new trophy wife, and the women were too polite and too mannered to say anything directly, but their eyes said it al... Continue»
Posted by TransContinental 7 months ago  |  Categories: Shemales  |  
1388
  |  
89%
  |  7

BBC "GIANT" David

this is for my huge ultra hung super strong friend too2badd David

It was the morning i would meet the biggest man i ever mett ,A huge hulking black man who hada huge hard on ever since we met and is as hot for me as i am for him not only is he hung bigger than a bull but is way taller than any one else nearly twice my tiny five feet zero tall and his cock goes on forever long and thicker than my fore arm.
I stood loking in the mirror as i aplied my whoreish make up and slipped on my tight white silk panties god i was having trouble already with my big throbbing hard clit in anticipation of... Continue»
Posted by huge_cock_rules 1 month ago  |  Categories: Fetish, Gay Male, Shemales  |  
2502
  |  
89%
  |  6

Little Public Stripper

I walked across the nightclub floor, two female friends either side of me. My short red dress looked perfect with my red patent heels, and my ass and g-string showed below the hemline. My skin felt alive, smooth and shaved and tingling, ready for this experience. The matte gloss of my long, black 1950’s style hair style (an expensive, convincing wig) picked up the pink and purple lights of the club, and I felt everything below my waist relax as it prepared for the sexual treat. Eyes were on me, desiring me. Girls and men alike looked my way, the women celebrating my liberation with me, the men... Continue»
Posted by CD_CutieBoi 2 years ago  |  Categories: Fetish, Shemales  |  
829
  |  
89%
  |  3

Wanted

Not really a story, more about what I want.

I am a Bi curious guy. I love pussy, but I really like cock. What I am looking for is a smooth feminine guy or tranny that would let me use him/her for an experiment... an experiment to see how far I'll go.

First, I would like to meet in a neutral place, somewhere private of course. I need to be discreet about it all.

I would like him to drop his pants and let me play with his cock. I'd kiss it, suck on it, rub it against my cock. Once he is totally hard I want him/her to lay back and let me worship at their alter. I'll lick it from ba... Continue»
Posted by siezetheday 3 years ago  |  Categories: First Time, Gay Male, Shemales  |  
720
  |  
89%
  |  2

Lilith RIDes Again

THe following event happend the night i took my profile pictures.......

I had almost given up all hope of finding a man online in time before my girlfriend and k** came home the next day. Finally at 4am a reply, his name was Todd. HE was on his way, one hour later he arrived. I got really dolled up for him this time; makeup, my favorite pink mini skirt and thigh highs on my smooth legs. When i let him in and disrobed he smiled and said "YOu are beautiful arent you?" I blushed a little as we sat down next to each other. HE put his hand on my thigh and i looked at him " DO yo... Continue»
Posted by witdacandy09 4 years ago  |  Categories: Shemales  |  
1460
  |  
89%

The Slut on the Balcony

A night away from home on business always meant a night of crossdressing and exhibitionism. I loved to get a room with a balcony so I could easily be seen by men walking around the motel grounds. This night I'd dolled in in a black lace corset; heels, hose, and g-string. I slipped on a leopard print short spaghetti strapped dress over; poured some wine and strolled out onto the balcony. My red wig flowed over my shoulders and my make up was just a bit slutty. I put on a choker that spelled out cumslut in rhinestones around my neck. I just knew that I would get lucky this night. Another mo... Continue»
Posted by dana213 4 years ago  |  Categories: Group Sex, Shemales, Voyeur  |  
1663
  |  
89%
  |  15

Cleaning up

It was my first time working late alone at the office; no managers and no day shift colleagues. Yeah, we have an evening shift, but not in my part of the building. I didn't want to work late, but I was way behind on my time.
I spoke with the security guard when he came past. I'd never had much to do with him, but to be honest I was desperate for some conversation. We talked sport for a few minutes before he moved on. He would be back two hours later. If I was still there he'd show me out, as the building closed up then.
About twenty minutes later I'm going stir crazy. I'm rarely alone and ... Continue»
Posted by sinnedbad69 1 year ago  |  Categories: First Time, Masturbation, Shemales  |  
2550
  |  
89%
  |  1

car fun!

Some years ago, I had overnight business travel and I cross-dressed in my motel rooms after hours. I had some married men that I met online that would come see me when I was in their towns, and get some sweet head from me on their way home from work or whatever. One of my regular hookups, named Frank, pulled into the motel parking lot late one afternoon and looked up and saw me on the balcony. I was in a mini dress; heels and all dolled up, waiting for him, but was just getting a little "exposure" time in, as I waited. When Frank came in he said that he could tell that I was into being seen an... Continue»
Posted by dana213 3 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
1091
  |  
89%
  |  6

Taken to be a Shemale Lover

I had went to work at the burger joint, when the manager informed me that 'I have too many people on payroll today, I need you to clock out and leave.' This is what happens when you work for a fast food joint, all the k**s that go to school and can get a permit flock to the fast food places. At least you get some training in how to be on time and understand job responsibility.

As I was working towards the park a coral blue car passed by, it pulled into the lot across the street and came speeding back. The driver was a familiar face, Joliet, one of the she-males that enjoyed my restraine... Continue»
Posted by d4david 3 years ago  |  Categories: Anal, Shemales  |  
1580
  |  
89%
  |  5

Panty Corset Pleasure.

So ive caught you. I spun around and there was my wife. I was wearing black lace panties a Black Bra and a Red silk dress. I knew you was doing this, thats why my best knickers are getting stretched. Get changed and I will wait in the car for you. We went shopping and I tried to talk but was shushed and ignored. Wait in the car!! The shop took her longer than normal and I was desperate to explain it was just fun.

We arrived home in silence and she went in the bedroom. A while later I was called in. Shower shave and put these on she ordered. I looked at the pile of clothes on the bed. I sho... Continue»
Posted by davanamx 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
1302
  |  
88%
  |  4

Male to Female Transformation

Male to Female Transformation

Genre : TG SOS or Surgery/Transformation Male to Female
Story : Cristine Carter
CH - 1

The last thing I could remember was walking out of the Bank
and crossing the road to my car. I had just been to see my
bank manager to discuss transferring some money from one of
my accounts into a high interest savings account.

I had won quite a bit of money on the Lottery, enough to
change my life. I was unaware just how much my life was
going to change.

I had just reached my car door when I felt someone bump
into me. Then everything went blank...
... Continue»
Posted by cristinestone7575 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
6035
  |  
88%
  |  10

Clara Bow's Academy For would-be Ladies Part

The new sissy stood barefoot; naked but for the soft white gown. Though bewildered and a little scared, her little cock poked forward in the gown, partly through fear and partly through excitement as she felt the eyes of the stern woman upon her. Clara Bow rose slowly from the leather chair she sat in, cane in one hand, she wagged a finger summoning Pepper forward. She was accompanied by the buxom Nurse Wykett; her ample buttocks and breast bulging in her white uniform, her black stockings and stilettos a far cry from the usual sensible shoe preferred by most in her profession. Mistress Bow... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
767
  |  
88%
  |  4