Shemales Porn Stories
Page 7

Becoming a Sissy Cocksucker (true story)

I always loved feminine things. I'd wear my s****rs panties as often as I could. I loved the way they felt, the soft fabric, the high cut legs, and especially the frilly lace edging! I graduated to bras and padding them and wondered what it'd be like to be a girl.

I always loved watching porn where a guy is sucked off by a
woman. I started to realize, what turned me on the most about it was watching his cock when it orgasmed! I LOVED watching the cum shoot out and on to her face and in her mouth! I used to watch it (and still do) dressed in panties. Well, fantasy eventually took over, I wo... Continue»
Posted by vickiebicd 4 months ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5740  |  
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The Day Lana Turned Me Into Her Daughter!

When I was much younger my neighbor, Lana, a divorcee, kept an eye on me while my folks went out of town. It was she whom formally introduced me to cross dressing and it was quite to my surprise. Back then I could actually pass for a woman due to my build. My hair was shoulder length and my body was small framed with feminine features.
I used to try on my mother's panties and clothes even though they were too big for me. Lana, on the other hand, had a great body. She was athletic and did not have a huge chest or big ass. She had great curves and was well defined. When my parents asked if ... Continue»
Posted by lovetopleaseu 1 year ago  |  Categories: Fetish, First Time, Shemales  |  Views: 5737  |  
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My sexy wife has a secret

My wife, what can I say she is tall and leggy with thick, natural wavey orange red head with beautiful porceline skin and just enough freckles to tell you she is a ginger. Add to that smokey green eyes and thin sexy lips and you can see why people refer to her as Gorgeous Gwen.
From the time we started dating my friends all expressed their envy at me landing such a smoking hot piece of ass. She is a freelance writer for fashion magazines and on-line blogs so she is pretty dressed up where ever she goes.
I got home one Friday evening from an afternoon shift. I knew she was home because ... Continue»
Posted by triphammer73 8 months ago  |  Categories: Anal, Fetish, Shemales  |  Views: 5718  |  
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Trapped and Trained Sissy Ch. 01

Trapped and Trained Ch. 01
I responded to an ad on Craigslist from some guy asking for help to move some furniture. He was paying pretty well and, after I practically laughed at him for asking if I could lift the furniture, he agreed to have me over to get it done. We moved everything around for what felt like hours, often moving the same piece of furniture to what seemed like the same place it was originally. Finally he decided he liked the new arrangement, which wasn't that drastically different than how it looked when we started. Obviously exhausted, I sat down on the couch. He asked me if... Continue»
Posted by hpm12 1 year ago  |  Categories: BDSM, Fetish, Shemales  |  Views: 5694  |  
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Sissy story

Date: Thu, 11 Aug 2011 16:42:22 -0700 (PDT)
From: Danny Smith <bobber1945@yahoo.com>
Subject: A Sissy Story Part 2

I got very excited writing the following story

I always considered myself straight. I was married and at 55 my k**s had
flown the coop. But over the last few years I began to fantasizing about
cocks and being submissive to a more masculine man. I was 6' tall fairly
trim at 175, but with a small 3.5inch cock. I never thought a lot about the
size of my cock until one evening while I was traveling I visit an adult
video arcade. When I entered one of the video booths, I s... Continue»
Posted by aimen72 1 year ago  |  Categories: Gay Male, Shemales  |  Views: 5659  |  
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First big cock.

So I'm deciding to post a story about an experience I had about a year ago. Ill start with a little background about me, I'm a bi crossdresser 22 years old 5'8" 140lbs, newly exploring bottom, very passable crossdresser. And extremely selective.

I tried an online dating site and eventually met a white guy in his 40s well built professional that likes to top. I told him that I was a beginner at being a bottom and that I thought he was really handsome but his cock was just way too big for me to have sex. We became friends and chatted all the time. Until one weekend he got a hotel room and sa... Continue»
Posted by Cutiecdny22 18 days ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 5657  |  
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sissy blackmailed by teamviewer and exposed


my fantasy about being blackmailed and totally ruined

watch out this could happen to you

im a sissy faggot I live in st Louis mo im in the closet no one knows i dress in femine clothes I was married when I was 20 and straight after a year I caught her cheating on me , we only had sexy 3 times I couldn't get hard with her , I was allways thinking of men, masters, tops, at home I stole her panties bras high heels lip stick, and would dress around the house, after the divorse I got the house and I started to wear panties to work everyday and shave my legs smooth , somedays i wear stocking... Continue»
Posted by sissypattie 12 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  Views: 5636  |  
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Tranny tricked the Postman

A true story…

I’d woken earlier than I’d wanted for a rare day off from work and decided to see if I could have a little fun.
So I did my make up and found the longest false lashes I had, touched up with the darkest mascara there is… with a touch of glitter… bright red lippy, a naughty smile, get the picture?

I put on some sexy underwear and a black lace top, little skirt with heels and hold-ups… I was on the hunt for cock but how could I trick a complete stranger into some naughty fun with a horny tranny??… I had a plan…

I was expecting a parcel in the mail that was too big for the... Continue»
Posted by JoanneCoxTV 6 months ago  |  Categories: Shemales  |  Views: 5623  |  
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more than expected teaching a neighbour to drive

It was a glorious summers day and I was chatting with my neighbour. he asked could i give her husband some driving lessons. Well I've met him but he is very quiet and so I thought this would be a good way to get to know him, so
"yes, when is the best time for him to go out" I asked
"He's home now if you've got the time" she said.
"Yes i'm not doing anything. Give him a call and i'll take him now"
So out he comes and I introduce myself and ask if he's driven before. "yes" he said so I gave him the keys and off we set.
His driving wasn't the best and I had to help him out quiet a bit. We... Continue»
Posted by xdrespauline 9 months ago  |  Categories: Anal, Gay Male, Shemales  |  Views: 5553  |  
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Cruising The Drive In

It was a Friday night and all of my friends were at home with f****y. I was really bored and I asked my dad if I could take the van and go to the movies. He said it was ok and told me to be home by midnight.

The van was a 1977 Chevy van, it was brown in color and had the moon windows cut into the side. It had the typical "Captain' s chairs" up front and in the back had what you'd expect from a '77 van. It had a couch that turned into a bed.

Around 7:00pm I grab the keys and tell my parents that I was leaving and that I would be home by midnight. I walk out to the driveway, get in the v... Continue»
Posted by cockwhore_4u 7 months ago  |  Categories: Fetish, Gay Male, Shemales  |  Views: 5549  |  
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My first time with a shemale

This is a true story, probably the wildest thing that ever happened to me. It happened when I was about 19 years old and lived in Hamburg, Germany. At the time I was one of those willowy, thin guys, little body hair and a healthy appetite for sex but not much experience yet. At a young age I discovered how exciting it is when I fondled and fingered my ass while masturbating and I developed a real fascination with anal sex.

At the time I used to visit a club ("disco" in those days) somewhere off the Reeperbahn, the famous red light district in Hamburg. One such Saturday I left the club in ... Continue»
Posted by HOLY-SMOKE 3 years ago  |  Categories: Anal, First Time, Shemales  |  Views: 5489  |  
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Crossdressers First Time

I was in my mid 40's and divorced and living a great life. I ran my own successful business from home and lived in a large house in its own grounds at least 5 miles from my nearest neighbour.
Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet up for sex or go away for a break all no strings attached. They all knew of each other and I was aware they saw other men or ladies if they wished.
Debi was 50 a successful lawyer and very dirty. Helen was 60 a retired busin... Continue»
Posted by maninnylons 18 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5479  |  
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My Neighbor and I first time!

Recently I had a college student move into the apartment next to mine. He was small, shaggy blonde hair, without any facial hair, looks like ever. Skinny with little muscle tone. We started talking while he was taking a break. I told him the normal neighborly bs. Then I went on about my day. Seen him and talked to him every now and then. I found out he just turned 18 and was on his own for the first time. We both enjoy sports beer and junk food.

One day I was walking by his window, I just happened to look in and saw a skinny ass in panties. Pink boy shorts, my first thought was good for hi... Continue»
Posted by thetodd83 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5434  |  
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My first cock-turned me bi

Most of my life I have been extremely hetero. I mean, absolutely no interest whatsoever in men. I have always loved everything about women, their scent, their soft bodies, their boobs, their muffs, everything. I could go on and on about how much I love women. I never, ever saw myself being with a guy. It just didn't ever interest me.

About 3 years ago, I was on a business trip that took me to Chicago. I was by myself in the evenings for a week. Anyone who has been on a business trip should know that after the work is done during the day, at night there is something about being alone and out... Continue»
Posted by Dionysus2 9 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5306  |  
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The Body Shaper

My wife was always ragging on me about my posture. She said I slouched
and needed to stand up straighter and pull my shoulders back. I tried
to do that, but as soon as I stopped thinking about it I guess my
posture reverted back to what, for me, was 'normal' and then she would
get on me again about it.

We had been married for five years and I think her good cooking got the
best of me as I had gained about 20 pounds since the wedding. My
weight was her other pet peeve. If she wasn't nagging me about my poor
posture, she was on my ass about needing to diet and to start
exercising.... Continue»
Posted by kynthia77 1 year ago  |  Categories: Fetish, Shemales  |  Views: 5285  |  
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Lodgers Surprise

I had started my first job after leaving university. Having moved to a small town where I knew no one I had taken lodgings with a couple who had a large house a short walk from my office.
The couple were called Jenny and Mike. They were both in their fifties and had retired early and took in the occasional lodger. Jenny was about 5 foot 2 and was plump and sexy. She had good tits and fine legs which I often admired when I thought she wasn’t looking. To my joy she always wore nylons either stockings (I could see the garter bumps) or tights when she was wearing tighter clothes.
Mike was 5’11” ... Continue»
Posted by maninnylons 5 days ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5338  |  
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Seducing Daddy

I had started crossdressing when I was 5 years old when I went trick or treating as Princess Leia for Halloween. The first time I pulled on a pair of pantyhose, I was eight years old. I could not understand how a piece of clothing that I could crumple into the palm of my hand could cover my mother's legs from her toes all the way up to her waist. So I decided to try on a pair...and it was the most exhilarating thing I had ever experienced!

I began experimenting sexually with friends shortly after my twelfth birthday. It was 1984 and my father had recently purchased and brand new piece o... Continue»
Posted by cdsexslut 2 years ago  |  Categories: First Time, Shemales, Taboo  |  Views: 5271  |  
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The neighborhood sex slaves Part 2

Jack and the girls had gone home about an hour ago and I was in the gym working out when I heard the front door open. Kelly came bounding in calling out my name.

I told her I was in the gym working out.

Kelly sauntered into the gym wearing my favorite little black skirt and red tube top with a "cheshire cat" grin on her face. My cock stiffened a little when I saw her. She came over to the bench where I was now sitting up, straddling my legs and sat down. She looked at me in my eyes and said "I've missed you honey", "Did you miss me?"

Wrapping my arms around her waist, smiling, I said ... Continue»
Posted by Bigrodtaz 6 months ago  |  Categories: Anal, Shemales  |  Views: 5254  |  
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"When I became a girl..." Pt 1

My name is Gabriella. Let me start by saying that I always felt like I was different growing up.  I was raised by a single mom because my dad left the country before I was even born and we never found out where he went or if he was even still alive. I was actually born a boy and I was known to be a very cute baby boy throughout my first two years of life. Even though I couldn't remember their first two years of life, as it usually happens to most people, I had still seen pictures of me from back then. In a few of them I was dressed in light blue and one of the pictures even showed my uncircumc... Continue»
Posted by adblman 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  Views: 5228  |  
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My son got seriously hot

Well, life sucked after divorcing my little sheboy, he was everything to me, but I had to let him go see the world, he went to college, after leaving his job as a freelance babysitter to find himself, he was very good at his job, he worked as a babysitter for a filthy rich f****y, he used to make over £400 in 6 hours spread over a whole week, sometimes he takes overtime, however this overtime was more like parentsitting than else.

He would stay for a further hour to take care of the parents by getting into naughty games together, the couple were rather young, the man was just midway through... Continue»
Posted by starlight8998 1 year ago  |  Categories: Fetish, Masturbation, Shemales  |  Views: 5209  |  
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