Shemales Porn Stories
Page 110

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 3 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 3 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 3 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 3 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 3 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 3 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 3 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 3 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 3 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 3 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 3 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 3 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 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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foxxiroxxi gets fucked by a black bull at a costum

I was invited to a costume party by a good friend of mine named lexi , she has been my friend since we were k**s and knows i love to dress up as a women from time to time so she invited me and i accepted . The theme of the party was tight and short so unless you had the dress code on you dont get in . Lexi and i had to go shopping for new outfits to wear , we head straight to this dress shop that only has sexy club wear and dresses that only just cover your privates which was exactly what we wanted . Now both us were going to this party looking like two girls that wanted nothing more than cock... Continue»
Posted by foxxiroxxi 3 years ago  |  Categories: Fetish, Interracial Sex, Shemales  |  
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Weekend i will never forget(Part 1)

I hadn’t seen Cindy for nearly 2 years, other than a quick lunch as She passed through town last year. We text or IM almost every day and talk on the phone every few weeks. We had been coworkers for many years and remained very good friends to this day. I would say that She is my best friend as I have been able to confide in Her about things I have never told anyone. In addition to being a very trusted and loyal friend, Cindy is beautiful and very desirable. I still can’t figure out why some man hasn’t swept Her off Her feet and married Her. She is truly amazing.
As I said earlier, I ... Continue»
Posted by wannabesubformt 3 years ago  |  Categories: BDSM, Fetish, Shemales  |  
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Sometimes, mistakes do happen but they can be real

A few weeks ago I was wandering round some of the nice tv/gay sites for this area of France when I got a message from a guy asking me if I would like to meet. Well, I was very horny at the time, so nothing new there, was aching to do something to somebody or have them do something to me, you know the feeling, when you ache to feel something nice and long in your mouth or being slipped in your pussy.

I thought to myself why ever not, he seemed like a nice guy, he wanted to meet on his way home from work so we arranged to meet in a quite well known gay rest area between his destination and t... Continue»
Posted by antoniaf 3 years ago  |  Categories: Masturbation, 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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Flowers For Pansy

Daffodils were Pansy's favorite. To this day she is still a silly little flower gurl wanting, waiting, craving for another man to bring a fresh bouquet. But today was not an ordinary day. With the vacuum grinding and sucking and growling the knock on the door was just slightly audible. The little sissy . . . excuse me, pansy (she just loved being called a pansy) flamboyantly sashayed her way with little itty bitty tiny steps. She swung the door open and presented a lush bright smile. "Yessss?" She said with a lisp.

"Flowers for pansy." The delivery boy read off his note.

Pansy gasped wit... Continue»
Posted by amberfemxd 3 years ago  |  Categories: Anal, Shemales  |  
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in public

here are the usual disclaimers this story is for adults only if you are viewing this and
are not 18 years of age or older please close this page immediatly.

there is no cross dressing in the story but this is how I began my transformation from
regular boy into cock suckking teenage crossdresser.

we were having a really hot heat wave here in philadelphia; my mom wanted me to get out
of the house and off the computer so she suggested a movie. I felt wierd going to the
movies by myself but I really did want to see that inception movie. I looked up when they
the theater opens up ... Continue»
Posted by kellyblue66abc 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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first time with a strap on

I think I can trace my new addiction back to a short fling I had with a girl a few months
back; I'm 22 years old slim; about 6', and fairly good looking. Not trying to be conceaded
but simply stating girls would be atracted to me however it would be difficult for me to
progress with them because I am so shy. Well back to the story; I Kristen at a local college
bar; very pretty but a bit on the rocker chic side. I lived on campus in a converted
victorian house with several room mates. We had several sexual encounters which were great
but on the last 2 occasions kristen let me fuck her ... Continue»
Posted by kellyblue66abc 3 years ago  |  Categories: BDSM, Gay Male, Shemales  |  
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