Shemales Porn Stories
Page 112

My first pair

More accurately I would have to say they were the first pair I did not have to steal and try on while hidden away in my room. I am speaking of pantyhose and other sexy feminine things like panties,high heeled shoes, stockings and the occasional dress. My s****r had known for a long time that I had developed a taste for these silky lingerie. I remember the the time she caught me, or at least the the first time she let me know that I had been found out. I still very young, only about ten, but I had been secretly trying on my mom's or my s****r's pantyhose for a few years already. I must have sta... Continue»
Posted by stedehans 9 months ago  |  Categories: Fetish, First Time, Shemales  |  
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my shemale GF part 6

I love cock now just as much as I love pussy. I was eating a hotdog and it wiggled around in my mouth and my dick got hard, hahahaha. Alright, so Christy walks around the apartment naked, which is weird yet hot, her tits bouncing up and down, her cock moving side to side, her brown hair flowing oh so lusciously, it makes my cock hard, and sometimes she walks around with her mistress outfit on, and I'm the one walking around naked with a buttplug in, just in case of a suprise fuck attack. She was walking around naked as usual, well she was sitting down. doing something on the computer, it was p... Continue»
Posted by germanface 2 years ago  |  Categories: Anal, Fetish, Shemales  |  
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How I got started dressing

I was a sophomore in high school and like any teenage boy I was extremely horny. I masturbated atleast once a day usually 2 or even 3 times because I had so much time on my hands. I started off watching plain straight porn but I watched so much of it daily that I started to get bored of it. I just used sites like google or yahoo to find videos by typing in whatever I was into that day. It started out with just words like "blonde getting fucked" or "girlfriend giving blowjob." Once I started to get bored my words started to get more descriptive "Slut takes huge cock in ass."I was skimming throu... Continue»
Posted by pantyyboy 4 years ago  |  Categories: First Time, Masturbation, Shemales  |  
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Becoming wife of competitor feminized by secretary

I am Siddharth Mittal, running my own Company with USD 100 Million of Business. Everything is going on well and I am excelling in my business. I have a secretary named Sonia. She is a smart and beautiful girl with 36-32-36 size. She knows how to get her work done. She wears simple clothes and is decent in her approach. I have never looked at her in any wrong sense.

I have a strong competitor who I always suspect is on the wrong moves. His name is Rahul.

One day I was working out a business proposal when Sonia rang up to say that Rahul is here and wants to meet me. I asked her to make him... Continue»
Posted by Sissy123 3 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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Virgin Sissy learns her place in life

As with any relationship, things change. The suprising thing that happened between me and Martin was at the begining he was a bit soft and I was the dominant person. It could have been that he was new at college and a bit shy. But as the summer went on he bacame a member of the Football, Tennis and Hocky teams. All the better as far as I was concerned as he had three different kits for me to sniff and lick after he had been playing. Blue top,shorts and socks for football, white t shirt shorts and gym socks for tennis and Blue top and white socks for hockey.
One Saturday, Martin turned up at ... Continue»
Posted by igglepiggle 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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A Slut is Born

A Slut is Born
I am a bottom for sure. It has been a long time, 20 plus years, but do miss it alot. Back then, I was in my 30's and this guy I met while I was tending bar talked me into coming to his camp for some fishing. Needless to say I was the fish and did not know it. He picked me up and we went to his camp which was 1 big room with a kitchenette and a big bed, sofa and a TV. The bathroom was small with a shower only. I noticed right away he had a wall filled with VCR tapes and I am a movie buff so went over and started checking them out. HMmm, I did not recognize the titles but felt t... Continue»
Posted by iwannabeacumslut 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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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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Vegas Sissy

So me and my girl friend Michelle split up, we'd been going out for 2 and a half years but the arguments just got too much for both of us. Unfortunately we'd booked a holiday together to go to Vegas, something we'd planned for a while. After compromising with other things I ended up getting the holiday to Vegas, I was still hurting from the split but I also thought about all the hot bikini clad women that were gonna be around the pool. I thought it would be great for me and one of my mates to go and try and pull some American women but I couldn't get anyone to go. I had a free ticket but no on... Continue»
Posted by lolli27 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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my wife make me her sissy slut

I married Jen when I was a successful high earning bachelor at the age of 30. She
was 25 at that time. 5'4" same height as me, 120lbs, petite blonde with
blue eyes, a set of DD tits and an ass to die for. I was short, skinny yet she was
attracted to me when we first met in a bar down town. Later on I found out that it
was Laura her friend who had told her that the porsche parked outside was mine.
Now, after 5 years of marriage, things were quite different. Things had actually
started going down hill after the first few months when subsequently Jen had clearly
stated that my 3 inches coc... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Gay Male, Shemales  |  
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wild halloween night

WILD Halloween PARTY EVER

First sorry everyone it’s been a several month since I been here was busy with my life.
Anyway Halloween comes once a year and we all wear custom and I know personally lots of guys like to wear female custom.
I am cross-dress and love Halloween, this Halloween was wild first ever wild Halloween party I ever been too.
It was black party nothing but black guys and very few white guys but lots of white, Asian and black shemale was their and soon I walk in lots of black guys was all over few of them took me in ally make give them blowjob. One group of 4 guys tha... Continue»
Posted by shawn777 4 years ago  |  Categories: Gay Male, Group Sex, Shemales  |  
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A Wonderful Ordeal

Part 1

Don and I had met on the internet in a chat room. Over the course of a month we had gotten to know each other and had shared our fantasies. Don was very dom and enjoyed the fact that I was very sub. I had shared with Don one of my favorite fantasies in which I'm a*****ed and f***ed into sexual servitude.

Don was a cross country trucker and came through my city very often. We had talked about meeting and living out our fantasy. He was married but was interested in being with a sub TV. He made arrangements for a long stay over in my city so that we could be together for the we... Continue»
Posted by celeste_tv_2000 3 years ago  |  Categories: BDSM, Shemales  |  
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cumsquirter and teen girl

What an experience i recently had, meeting a 18 year old girl at an adult bookstore! We hit up a conversation, and i told her that i would be upfront, that i am a shemale, at which she said to me, "No fucking way, you are so cute"! Nice to hear that, she was beautiful, about my height 5'7'', long blond hair, cute face , long sexy legs and nive tits and waht a great ass! she told me that she was straight, but always thought about what it would be like to have sex with a shemale, so i asked her why she was at the adult store. She said she was looking for a vibrator or dildo, and she told me she ... Continue»
Posted by cumsquirter 4 years ago  |  Categories: Shemales  |  
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One of my favourite experiences.

I don't know if anyone will read this or even enjoy it but I've not told it before and it gets me really... excited :P
This took place before I discovered my love for crossdressing and I suppose could also be the reason I started!

A few weeks after I turned 18 I got a girlfriend. She was bisexual but she didn't know that I was also bisexual. Her name was Lisa and she was also 18. After a few days of seeing each other we ended up having sex. It was your average, nothing exciting, foreplay followed by sex.
After a few weeks of our relationship we were getting on great... We'd learned so muc... Continue»
Posted by matttay 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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The way i like to be treated...

One night, You call me on my phone and ask me to come to Your place. i feel excited, because every time i see You, i have a hell of a good time :-) So, i hurry to come to Your place as soon as i can.
Once at Your door, i knock. I can hear You say "come in", so i come. Without any other word, You say "Naked!". So i undress. "Quickly" You add. I undress as fast as i can. "Seems like you're horny. Good boy. Turn around" You say. So i turn around and my back is facing You. i can hear You come closer. Then, You firmly squeeze my ass cheeks. "I'm gonna have some fun these, you know? Very soon. But ... Continue»
Posted by mouth2fill 2 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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The Bondage Whore, Chapter 1

The Bondage Whore, by Rachel St. Clair, All Rights Reserved.


Chapter 1 - Job Interview

It was around 4:30AM and Rachel St.Clair was beat. Walking the streets for such a small amount of money really sucked!!.. And no pun intended, Rachel wryly smiled. The streets were now deserted, no more money to be made tonight. Rachel started to head towards the seedy hotel where she barely managed a one bedroom fleabag. "I've got to find a way to make some better money", she sighed to herself.

Rachel was now 24 years old, and had been walking the streets since she was 16, after an abusive sugar... Continue»
Posted by thongcutoffs 4 years ago  |  Categories: BDSM, Fetish, 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 2 years ago  |  Categories: BDSM, Gay Male, Shemales  |  
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my BBC adventure at the adult theater

My bbc adventure at the adult theater
Gurls, you have no idea. I think I'm in luv. Omg he was amazing.

No pics, but I was in my 6 inch cum fuck me pumps, had on an opaque black body stocking with red fishnet thigh highs on top of it, a frilly lacey black ultra miniskirt, black Lacey top with my corset underneath tied real tight to give me a little bit of waist, my best padded push up, short red Bobb wig, red lips, blue eyshadow etc. gotta say,I was looking pretty hott and all the guys said so.

One white guy followed me into the theater and sat next to me, the two black guys who were th... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Interracial Sex, Shemales  |  
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Margret beach suprise

John and I have recently returned from a trip to a naturist beach in Spain which has one or two swingers clubs near by.

But there was no action due to the floods southern Spain has been having.

We were on the naturist beach when I spotted a blonde beauty she was very attractive beautiful breast great nipples, but she was wearing bikini bottoms so I could not see all of her. I felt my pussy getting wet.

John had gone for a walk, so I went over and she said that she like my tattoo's she had a strange accent. She said her name was Eva from Austria and that her boyfriend Juan had come dow... Continue»
Posted by manfed 2 years ago  |  Categories: Shemales, Taboo  |  
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working hard

My name is Micheal my birth. But I am known as Michelle As a c***d I had began cross dressing at around ten years age. I had actually been allowed to pick out and wear anything from my mother's closets and drawers. I was a very feminine boy and was often mistaken for being a little girl.My mother understood that to f***e me into a gender that was not really part of me would affect me badly for the rest of my life. My mother understood this because she herself was a lesbian and had divorced my biological father before I was five. She had been living with a very pretty lady Samantha. My Mother ... Continue»
Posted by christinefan 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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made me a slut.

I spent my time online since I was 18 watching tranny porn and crossdresser porn I really enjoy a mix of both especially with a big black cock in between I found a movie with a ebony tranny with a big cock and a white sissy gurl with a nice sized cock also... They got dolled up together and all of a sudden they were smearing each others make up on each others cocks... The things I saw that happened to that sissy was some of the hottest things I have ever seen... After this video I couldn't just go back to regular porn or continue searching online to watch videos, none matched up... So I starte... Continue»
Posted by reefermcrevolver 3 years ago  |  Categories: Group Sex, Interracial Sex, Shemales  |  
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