Shemales Porn Stories
Page 75

Natural Ingredients for a crossdresser

It was still snowing outside and I wasn't going to be recieving any visitors today so I decided to treat myself and while the day dressed how I wanted.... I had set the heating up high at my place, so I could wear one of my sexy side tie bikinis which show off my sweet little ass so well. Having enjoyed the view in a full length mirror and got some self shot snaps, I found myself sitting at my dressing table wondering how to amuse myself next....
Looking at my face in the mirror I noted a little dryness (no doubt from my earlier shave, god how I hate that ritual, you girls don't know how luc... Continue»
Posted by MagicCarpet 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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A Cross-Dresser's tale

You may think of me as Fiona, and I am a cross-dresser.
A story by Erica inspired me to pen my saga of cross-dressing.

I am also a recovering alcoholic, with a few days over 19 years without a drink as I write this, and I suppose the two tales are intertwined to some extent.

Not that I am a saint by any means, a lot of people with a lot less time have a better sobriety than I. But I learned that alcohol is a poison to me, so I avoid it. I just do irrational things when I add alcohol to my system.

For a while, I blamed my cross-dressing on the booze. But I discovered that feelin... Continue»
Posted by prairieFreak13 2 years ago  |  Categories: Shemales  |  
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A wonderful experience


When I was 20 years I was a wonderful thing happened as I remember all my life.

With my best friend Dani and friend, we agreed that we are going to our dull and went around the city a bit. This was a great opportunity for me to be dressed as a woman and such a walk around town for all to see. From what I can remember is I enjoy women's clothes and the role of women. Although I had all the things women I asked a friend if I could borrow her things and be with her disguise, that would not be too suspicious that I'm a transvestite since time immemorial.
Dani and I have come to friend Suzi w... Continue»
Posted by maximatv 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Clara Bow's Academy For Would-Be Ladies Part

Pepper returned to the room and sat on her new bed as she unpacked her things; Marie helped her stow things in a wardrobe and chest of draws allocated to her. The blonde smirked at the new girl as she blew on the brunettes nails she’d just completed; she would enjoy painting Pepper’s nails. Pepper bounced softly on the large double bed; the plug felt so nice now, and she loved the way it teased her anus.

“Why such big beds? I’ve never had a double before and it feels so comfy.” The three girls glanced at each-other knowingly, and then giggled; Pepper’s jaw dropped as Marie let her fluff... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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Going out as Leslie

A Short Story...

There was an unmistakable feeling of acute anticipation in my stomach leading out to my trembling hands. I knew where I was going tonight and the probable outcome.

Shaved, made-up sexy, dressed in a 3in heeled mini boot, fishnet stockings with a garter, black pleated short skirt, a white blouse with ¾ length arms exposing fishnet arm warmers to a stunning black straight haired wig, didn’t help the situation any.

Going dressed like this to a man’s lair and offering myself to him…I was quite apprehensive to say the least. Will he accept me? Will he go arm in arm with me... Continue»
Posted by LeslieStone 2 years ago  |  Categories: BDSM, First Time, Shemales  |  
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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  |  
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Pia's T-girl adventure

I met Pia a couple of years ago when I was out with friends at a transgendered night club in London. Originally she was born in Finland but she has lived in London now for several years. Her looks are typically Scandinavian with platinum blonde hair and a beautiful, friendly smile. Although I had never had sex with her or seen her naked, I could tell that she has a lovely, shapely body. After chatting with her I discovered that she is bisexual and really only interested in meeting other woman or couples after enduring, what she calls, too much ‘vanilla sex’ with straight men. I also discovered... Continue»
Posted by lightwave40 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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Clara Bow's Academy For Would-Be Ladies: Part

Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his anus tingled and gripped the soft rubber plug she’d also chosen for his first day. His stepmother had allowed his soft ginger hair to grow to shoulder length already, and his dosage of hormones had been already been increased. He had been suitably attired in a gingham dress with pink socks and red... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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My first time

I sat in the car outside the address and to say I was nervous is a understatement. This was the first time I had ever done anything like this and I was half thinking of just driving away.

I had got messaging to Sara a month ago after liking the pictures they had posted. I was really in to clothed sex and the pictures showing Sara in a selection of boots whether they be leather or pvc, knee high or thigh high I didn't care as long as they have a stiletto heel l love them.

As for clothes I get hard for the slutty secretary look, a nice tight pencil skirt with some stockings and high heel... Continue»
Posted by big_rob49 2 years ago  |  Categories: Anal, First Time, Shemales  |  
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The Slave and the Sissy Part Nine

Ayesha was not to be denied; slave was rampant after witnessing the erotic antics of the maids, and was anxious to please Ayesha quickly, so that he may watch over Pepper; she was so soft and vulnerable. Slave’s cock rose quickly as he sniffed at the gloriously rich scent of the dusky beauty’s thong. She smiled with a sense of admiration as he licked and lapped at the savoury gusset without faltering in any way; she watched over him, whip in hand as he lovingly licked at the tangy brown streaks to the rear of the gusset as readily as he had dealt with the yellowy stains to the front, where h... Continue»
Posted by midsummerman 2 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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My shemale boss part 2

Friday 12pm was here, I nervously knocked at my bosses door part excitement part apprehension ran through my body.

A clear come in could be heard from within by my boss Miss Jones so I went in. Ahh Rob right on time, take a seat and I'll be with you in a minute, she said.

I sat down opposite her desk whilst she continued to study her paperwork. Her black rimmed glasses were on the tip of her nose and with her finger, she curled her long black shoulder length hair. Through her glass desk I could see her tight black leather trousers she had on and black 5" heals. She had walked through my... Continue»
Posted by big_rob49 2 years ago  |  Categories: Shemales  |  
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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 2 years ago  |  Categories: Group Sex, Shemales, Taboo  |  
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My shemale boss part 1

I knocked at my bosses door and on her reply went in. She was standing with her back to me looking out of the window and talking on the phone.

She failed to agknowledge me so I just sat down in one of the leather chairs opposite her desk. I looked at her as she stood by the window and perved over her black stiletto leather knee high boots and tight black leather skirt which covered her ass beautifully.

After about five minutes she turned to me, her black hair to her shoulders and her black shirt partly Unbuttoned showing off her cleavage, it has hard not to get a semi hard on as she move... Continue»
Posted by big_rob49 2 years ago  |  Categories: First Time, Shemales  |  
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Three's a Crowd

It was 8 pm and the guests were about to show up. My tight little bunghole was not virgin anymore and I felt like walking on clouds. I felt very feminine and quite demure. I had helped Carlos set up the table with snacks and put sodas and beers in the fridge. I looked in the hallway mirror and everything was still in place.
"You look adorable sweet cheeks", Carlos murmured in my ear and squeezed my ass. He went to answer the door as his guests arrived. A short plump blonde boy went past Carlos and to the guest bathroom to change. As he went past me, the guy winked at me. I could not imagi... Continue»
Posted by latinCharm 2 years ago  |  Categories: Anal, Group Sex, Shemales  |  
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Becoming a Princess Part I

Well, I figured since I havent posted a story yet it was about time I did. This story is for the most part fiction. But has some fact in it about me as well as partly being based on an experience I once had. Some parts that are fiction will be slightly obvious. But I know some of it could work in reality even if its a little out there. I may write an “extended version” in the future. Or maybe “directors cut” would be a better term. I will be compressing the story because I think if I were to go into exact detail with every part, writing the whole thing would take me several days. And I just do... Continue»
Posted by want2bespoiledutcd 2 years ago  |  Categories: Mature, Shemales, Taboo  |  
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Wealthy Sissy Surrender Station

Fire immediately engulfed the house just next door after an earth shaking explosion rocked the neighborhood. Fear was setting in. The rebels were getting closer and closer, Inch by inch. Relentlessly. Terror crept in as silhouettes and shadows extended deeper into the darkness with sudden flashes of light exposing their footsteps. I held my breath and cowered in the corner of the room. Shock waves riddled the streets. Please, let this end. Another bombardment shook the ground pushing me around and tossing loose paper in the air. I started to cry and that's when the pamphlet slowly fell into my... Continue»
Posted by amberfemxd 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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Master's Surprise For Me

Master called and told me to be ready at 5:00. He instructed me on what to wear, a blouse and skirt, and to wear my long hair in a ponytail. He told me to make sure my pussy was shaved and may nails done. He often likes to give instruction on my appearance when in his presence. I always love my time with Master and so it was with great anticipation I began to get ready. I was a little surprised that we were going out, since we usually play at my house. He told me this would be a very special evening, one i would not soon forget.

My pussy was getting wet thinking about his words...he... Continue»
Posted by ThyMastersBitch 2 years ago  |  Categories: Anal, BDSM, Shemales  |  
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An Evening With A Beautiful Woman And Her Cock

An older man finds an older woman and her cock at a Spanish class.

With winter coming to an end I was taking a class in conversational Spanish at the senior citizens centre because I planned to travel to Spain or Mexico next year. The people in the class were about my age, 60 to 70. I was fortunate enough to sit beside possibly the most attractive woman in the class. Unlike the others she dyed her hair a bright red and, come snow or sleet, she always wore a dress. For a number of classes we worked together trying out our poor Spanish until we could both ask where the toilet was, or order a... Continue»
Posted by smallfurrycreature 2 years ago  |  Categories: First Time, Mature, Shemales  |  
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Their First Adult Book Store. Part 4

Albert actually falls asl**p for a few seconds, before Gary opens the door to his booth. "Hey stud, thought ya might like some company over here."
Gary's cock is big and hard and right in Albert's face.
Albert's first thought is, 'I'm bigger than that'. He looks at Gary's face with its countenance of anxious, lustful anticipation. "Hey stud, to you too." Albert takes hold of Gary's dick. He starts to stoke it a little. "Wow, that is a nice dick you got there, Gary." Albert rubs up and down on Gary's cock awhile.
Gary asks “So Albert, do you and Joe…. you know… fool around with each other?”... Continue»
Posted by Michelle_Satin 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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A weekend in the Lifestyle Part II

When I was a teenager, I could get it back up and ready to fuck again just minutes after a huge orgasm, but now that I am in my thirties, it takes a while longer. Also, before I bust a nut, almost anything can make me hard, and I am willing to try new and kinky stuff. But, after I cum, my dick gets really picky about turn-ons and turn-offs. Before I exploded, Biff rubbing my cock and putting our cock heads together was a turn on, but now that I had shot my load, it was less exciting. Even his name bothered me, now that I had cum.

Biff and April went back to fucking and Buffy stroked my c... Continue»
Posted by Tgood10 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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