Shemales Porn Stories
Page 9

Sissy for BBC use and a b u s e

My Dear little sissy s****r, lezzie lover and slutty confidant...

Thanksgiving saw me full of BIG BLACK mouth, my sissy pussy and my belly were full of so much BBC and SPERM from Big Black Daddy Dick (s) annnnd I was good little bitch in the Doggy position for the Black Daddys' and their DAWG POUND(ING). I finally hooked up with my own BBC GANGBANG SQUAD from the adult bookstore. They used me for well over 24 hours of serious sissy-slut abuse, degradation, domination, humiliation and more, much, much more! I can't wait to tell you about it. I wish you were with me so w... Continue»
Posted by santtxx 12 months ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
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My first time with another crossdresser.

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my b*****r and s****r. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer to waist with reinf***ed toe suntan wolford pantyhose. They were incredibly silky and soft. i rubbed t... Continue»
Posted by sissypantyhoseboy90 4 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Dinner with Brooke

Brooke texted me on my way home from work, “I’m making dinner, come down when you get home.” I replied back, “Sure, I’ll stop and get some beer.” “No bother,” she said, “I already grabbed some. Just you is all we need.” This was always nice to hear, and it was always nice to see Brooke. I felt so comfortable with her especially since the many last encounters. But I never think any more than what it is. Just dinner.
When I got home, I went upstairs, dropped my bag and headed down the front stairs to her apartment. Her door was cracked open a bit so I knocked, saying hello and opened the door.... Continue»
Posted by ahsleymills 5 months ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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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 1 year ago  |  Categories: Shemales  |  
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I was 18 high and d***k when i stumbled onto a tranny hooker neighborhood and i stupidly picked up a sexy girl not realizing she had a huge 9in uncut cock and was almost twice my age!! I'm 18 thin great body lots of girlfriends and this night changed it all!!!!!

i went back to her place and we got naked and started smoking and parting and listning to house music and thats when i realized that i wasn't the top in this situation!!i was gonna bottom !!!! she dressed me up and shaved my ass and legs and head, put a wig and fishnets and a skirt that was really 2 short and black t... Continue»
Posted by LosAngelesSissy33 1 month ago  |  Categories: Hardcore, Shemales, Taboo  |  
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Panty Boys

By Fred Gingerman

Chapter One - Nerds United
My name is Mickey Donaldson. For most of my 16 years, the k**s have called me Mickey Mouse, because of my size and because of my shyness. I was only 5'3" and at 115 pounds, very skinny. My best friend Jeremy Haskins and I were always the oddballs. Jeremy was a little bigger at 5'4" and 120, but we weren't being recruited for our high school football team. Chess team was more like it.
We were pretty much classic nerds. Shy. Picked on. Ostracized. Intelligent.
But we were still 16-year-old boys and our hormones were stirring. Boiling actually. ... Continue»
Posted by BeeJay69 2 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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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 1 year ago  |  Categories: Anal, Gay Male, Shemales  |  
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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 1 year ago  |  Categories: Fetish, Gay Male, Shemales  |  
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My Aunt Gave Me A New Life

My Aunt Gave Me A New Life

As i already wrote, my Mistress has threated to turn me into a gay
shemale slut -- and i'm terrified. Last night i began thinking about how
this whole thing began.

We've lived next door to one another for years, and i've always admired
Her from a distance. She is beautiful! She has a small frame, 5'2",
dark hair, beautiful eyes, a dynamite little body with good size breasts,
beautiful legs. i guess You can say that She was my fantasy. A number
of years ago, when they first moved in next door, She came over with her
daughter to introduce... Continue»
Posted by klammer 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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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 2 years ago  |  Categories: Fetish, Shemales  |  
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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 8 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 4 years ago  |  Categories: Anal, First Time, Shemales  |  
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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 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Kitty's Weekend for a Huge Cock

I have to tell about an experience that I recently had with an old school friend. His name is Avik. I had moved far when I turned 15. We accidentally met one day at a mall. He was not able to recognize me at all and of course he was surprised to see me as a female because he had last seen me when I was 13-14 yr old boy. He was here for some work issues. We exchanged numbers and I got to know that he still stayed at our old town. It was good to know that he was bi and really interested in me too. After some days’ chatting we got the pleasantries out of the way, he sent me some pictures of his h... Continue»
Posted by CumLovingKitty 2 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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Sissy Jenny abused in the woods

Submissive Sissy Jennifer - taken in the Woods part 1

I stared at my screen - "Be at the entrance to Dutch Common at 12.30. Don't be late, and wear your sexiest sissy gear". 12.30! That was only 30 minutes! I could do it, just. But did I want to? Was it wise? I had never met my correspondent, a local bisexual man, but we had corresponded for some time. Meetings had been discussed, but they had never materialised. This would be the start of a very slippery slope, I knew.

My cock made the decision for me. I rushed upstairs, and slipped into me sexiest outfit. Truth to tell, I didn't ha... Continue»
Posted by sissy_jenny 2 months ago  |  Categories: BDSM, First Time, Shemales  |  
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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 1 year ago  |  Categories: Anal, Shemales  |  
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dressup sissy introduced to cock

When i was a teenager i lived next door to a guy named Gary. we were friends for years but drifted apart as he was 3 or 4 years older than me, so when he discovered girls i didnt see him for a while. However, one summer he and his then girlfriend had a fight, so being at a loose end he would invite me over to watch movies and play video games.
one day we were watching a movie, when Gary suggested watching some of his dads pornos. i eagerly said yes. so for a few days we would watch porno from about 10 am till 4 pm when his mom came home. his dad seemed to have hundreds of movies. one movie w... Continue»
Posted by hornyTVluvr 8 months ago  |  Categories: Fetish, First Time, Shemales  |  
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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 3 years ago  |  Categories: First Time, Shemales, Taboo  |  
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This is some of True incidents happen in my life when i take an office trip at last 2 years. After a long flight, I departed, and made arrangements for my luggage to be sent to the hotel, and then went to a restaurant / bar to get a meal and a drink. I am not a good flyer, and get real nervous during a flight, so I needed a drink to calm my nerves. I sat at the bar and ordered my meal and drink. After a few drinks were gone, I noticed this stunningly beautiful lady enter the bar. She sat a few stools away from me at the bar, and I couldn't take my eyes off of her. She was a raving beauty, with... Continue»
Posted by fukkerguy 2 years ago  |  Categories: First Time, Shemales  |  
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”I like cock” she said in that strange nasal tone of voice. I looked at her askance.
”Cock. I love it.”
”Thats what I thought you said” I said. Why was she telling me this?
Irena had asked if I could take Bela up to the hills and I’d agreed readily enough. Who wouldn’t want the company of a pretty young girl on a hike in the Upper Vidalen National Park? The sheer beauty of Norway laid out before our eyes.
I reached back and grabbed the thermos. I needed a moment to gather my thoughts.
”Tea... Continue»
Posted by Ijhel 7 months ago  |  Categories: First Time, Shemales  |  
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