Shemales Porn Stories
Page 10

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 2 years ago  |  Categories: Fetish, First Time, 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 5 years ago  |  Categories: Fetish, First Time, Shemales  |  
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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 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Leila Has a Big Secret

I'm an ordinary guy, nothing special about me at all. Well, maybe my choice in women could set me apart from most.

It all started one rainy afternoon in Northern California as I was driving home after a party I'd attended alone the day before.

I'd stayed over at a friend's house and after a nice leisurely breakfast I headed home so that I would be back home before dark. I had to be at work the next day and wanted plenty of rest.

I was driving along Highway 1 when I first saw her. And boy, was she a vision. It had been raining all morning and the woman who stood there beside the road w... Continue»
Posted by drew1207 1 year ago  |  Categories: Fetish, Sex Humor, Shemales  |  
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Ashley's first time pt. 1?

It all started on a sunny monday afternoon. I was 19 bored and laying in my room which was cluttered with my girlfriend at the
times clothes, she was so sexy, blonde hair which flowed down her soft 18 year old shoulders didnt weight but 110lbs standing 5 foot 4
inches off the ground. She also had great taste in style but hardly ever wanted to have sex leaving me constantly horny. She had made me mad that day and we got in a fight which led to her leaving me alone in the house for the entire day. i first went over to my laptop and started browsing through a few tube sites try... Continue»
Posted by ashleysrecret 2 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 2 years ago  |  Categories: Gay Male, Shemales  |  
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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 COCK...my 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 1 year ago  |  Categories: Hardcore, Interracial Sex, Shemales  |  
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Shemale Mom

It was a sunny day when I got home from School, My Mother asked me how my day was to which I replied that it was okay, she seemed pleased with my answer, then she said we'd have to have a talk after dinner, I went up stairs and laid down and started thinking about how I was bullied in school again, was it my fault I had a slight built and girls while nice did nothing for me.

After eating dinner I helped my was the dishes then we went into the living room to watch The Bachelor, she kept commenting on how cute the guys were. Later she said we need to clear the air son I told her okay, she sai... Continue»
Posted by sissytimmy 1 month ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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I Knew I Was A Sissy (Part 1)

I was on my early teens when I saw my first porn movie. It happened during a weekend, one Saturday afternoon. All the boys gathered at the house of one of our friends as his parents were to be away for several hours to attend a wedding. One of the bravest of the “gang” had managed to get a porn movie and we were all excited.
Movie was inserted on VCR (yes, I am that old) and the action started. Everybody was commenting on the gorgeous girls and after a few minutes (possibly seconds) we were all erected. It didn’t took long before everyone started to jerk off. Ten erected teens seeing porn fo... Continue»
Posted by georgette32hk 5 months ago  |  Categories: First Time, Gay Male, Shemales  |  
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The Making of a Sissy (Part 3: The Obsession)

As I laid in bed the next morning, I was overcome by the painful soreness and tingling sensations emanating from my tight freshly used hole. I could still feel his seed dripping out and leaking down the sides of my ass cheeks. I was lying there naked in bed, my long feminine legs spread out underneath the sheets. I felt like I had been hit by a train, but the previous night was the most satisfying experience I had ever had in my life. As I rolled near the edge of the bed, my eyes caught a glimpse of the panties I had been wearing. They were still laying on the floor by the side of my bed.... Continue»
Posted by briantid8 4 months ago  |  Categories: Gay Male, Interracial Sex, 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 1 year ago  |  Categories: Fetish, Lesbian Sex, Shemales  |  
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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 3 years ago  |  Categories: Fetish, Shemales, Taboo  |  
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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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HOW I BECAME a hollywood HOMO AND ADDICTED TO BEIN

PART 1
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 8 months ago  |  Categories: Hardcore, Shemales, Taboo  |  
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The Surprise

A divorced man finds love unexpectedly.

My wife left me a few weeks after my fortieth birthday. She ran off with a coworker, leaving me with our condo in the city. Getting dumped was a wake up call for me. I joined a gym and began working out and eating healthier. I was never fat or anything, but I got really lean and cut and began to feel confident in myself.

My friends looked out for me, inviting me out to dinner and fixing me up with friends. Maybe I wasn't ready to date yet, because there really wasn't any spark with any of the women they were introducing to me. I wondered if ... Continue»
Posted by magas911 7 months ago  |  Categories: First Time, Mature, Shemales  |  
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I'm My b*****r In Law's Wife

Bisexual male - crossdresser – bra – panties

It wasn't a typical visit to my mother's house on this particular day. We're both 22 now, and since my twin s****r and I graduated from high school we had only seen each other a few times. We never really got along because our mother always gave her special treatment. I was always being reminded that she only wanted one c***d and I was the second born, so I wasn't loved anywhere near as much. A few months ago I had received an invitation to my s****r's wedding and I was sure that I wasn't going. The 'emergency' call from my mother changed ... Continue»
Posted by naughty_bi_interest 6 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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my first black cock

One day when my mum was at work, I was laying in her bed, masturbating. I got up and rummaged through her underwear drawer. The drawer smelled like perfume and the odor made my dick stiffen. Some of her panties had stains - I think they were cum stains - on the crotch. Anyway, I don't know why, but something prompted me to try on a pair of her silky nylon hose. The material felt so good on my legs! Next I stepped into a pair of her red french cut panties. Then I caught a glimpse of myself in the full-length mirror - and was electrified.

I was about 5', 2" then, and the only body hair I had ... Continue»
Posted by allisontranny 1 year ago  |  Categories: First Time, Interracial Sex, 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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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 2 years ago  |  Categories: Anal, Gay Male, Shemales  |  
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