Shemales Porn Stories
Page 10

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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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 2 months ago  |  Categories: Gay Male, Interracial Sex, 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 3 months ago  |  Categories: First Time, Gay Male, 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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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 10 months ago  |  Categories: Fetish, Lesbian Sex, 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 6 months ago  |  Categories: Hardcore, Shemales, Taboo  |  
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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 24 days ago  |  Categories: First Time, Gay Male, Shemales  |  
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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 5 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 4 months ago  |  Categories: Fetish, Gay Male, 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 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 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 1 year 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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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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Kitty's emergency service

A friend of mine once told me that he knew a great guy and gave him my number. Soon I received a message. It was from a 23 year old college student named Mohit. He was going to college in the next town, said he was packed just over 7 inches, and sent a pic that made it look like he had a telephone pole sticking out of his groin. We traded a few emails and next thing I knew I was over to his apartment. I was kinda nervous when I knocked on his door but that went away when a good looking guy opened the door. He introduced himself as Mohit and invited me in.

"You want a beer or something?" Mo... Continue»
Posted by CumLovingKitty 2 months ago  |  Categories: Gay Male, Hardcore, Shemales  |  
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The Surprise Vacation



The Surprise Vacation


by an unknown author and Tristmegistus

1. Chapter - Innocent Beginnings

"Did you take your vitamin, dear?" Ellen called from the bathroom.

I rubbed sl**p from my eyes and picked up the pill bottle, rolling a big
tablet into my palm. "My horse pill? I'm doing it now."

"Have you noticed any difference yet?"

"Nah. Vitamins are pretty much all alike." She'd gone on a minor health
kick a month before, insisting that I needed to lose a little weight and
take better care of myself. I hadn't actually made it to the gym to wor... Continue»
Posted by klammer 2 years ago  |  Categories: Anal, BDSM, 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 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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We all shared the rent, and they shared me!

It was my Junior year of college, at that point I was mostly a closet cross dresser, with the exception of Halloween, and a few select occasions. I had been sharing a house with two other guys, and I they both knew I would dress, but we didn't speak of it, well until tonight. I was sitting around doing shots and watching tv with my two roomies, let's call them Jon, and Barry. Jon was a small skinny Korean k**, who was very much influenced by Barry, the all American boy, tall, blonde athletic. Back to our story, the three of us started talking girls, and fucking, and moved onto "would you if ... Continue»
Posted by smonkeys32 3 months ago  |  Categories: Gay Male, Group Sex, 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 7 months ago  |  Categories: Fetish, Gay Male, Shemales  |  
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