Shemales Porn Stories
Page 15

High School Girls

High School Girls
A Rings of the Oni Story

by Jaana


"Three teenage boys find their simple lives completely overturned, and
their friendship put to the test, when an unexpected find grants them
both nightmare and gift beyond price."

*** WARNING: The following story contains graphic depictions of sex,
female transformation and female arousal. You have been warned! ***





"Accept the things to which fate binds you, and love the people with
whom fate brings you together, but do so with all your heart."
- Marcus Aurelius, 'Meditations'

"For I have been a traveler in a... Continue»
Posted by lana100 2 months ago  |  Categories: Masturbation, Shemales  |  
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S****r has a Secret

Sarah was rummaging through her bedside drawers, turning them out and messing up the room she shared with her younger s****r, Hope. She was looking for her ipod. She had no idea where she'd put it when she'd gotten home the night before.

It was when she reached her bottom drawer than she found something interesting. Pulling out the stack of photographs that she hadn't known was there, she became furious. They were nude photographs of her, in the shower and masturbating.

Sarah was a transsexual. She'd had a sex-change when she was 18 because she'd always felt wrong in her male body, thoug... Continue»
Posted by drew1207 9 months ago  |  Categories: First Time, Shemales, Taboo  |  
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the surprise I loved

I never had never heard the term shemale or transexual. Didn't know anything about it. I joined the military right out of high school. Ended up in the far east and started out on the town. I saw a great looking girl in a bar and started to chat her up. I bought a few drinks and we were both starting to loosen up. Then out of the blue she asked if I wanted to get out of there and sme place more private. Now I had a few girlfriends in high school and had sex with a few of them but i had never had anyone address me like this. I wasn't she what her intentions were but I knew I wanted to fuck her. ... Continue»
Posted by gayswitch 3 years ago  |  Categories: Anal, Shemales  |  
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My Transformed Wife Part 2

"Absolutely," I said, rising to my feet and offering her my hand. She took hold and I pulled her to her feet. Her knees wobbled and I caught her by the waist before she could collapse again. "Woah, easy there."

"I'm not used to using those muscles like that," she said, grinning.

"Yeah, I'll probably be walking funny for a while myself." I helped her into the shower and she sat down on the built in bench next to the shampoo and soap bottles. I pointed the shower head at the wall, turned on the hot water, and waited as steam began to fill our little alcove and condense on the glass door. M... Continue»
Posted by drew1207 8 months ago  |  Categories: Anal, Fetish, Shemales  |  
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Shemale Summer

Once again, this is not a story written by me! It was stored in my computer for ages and decided to share it with you. Hope you like it!


One hot summer day, my friend Sam and I were scoping out the babes at our local beach, as usual. I saw this really hot, busty blonde a few towels down giving me the eye.
"Hey, check her out!" I said to Sam. He peeked up from beneath his Ray Bans and shook his head.
"Forget that one," he said. "She's not your type."
"What do you mean?" I said. This girl would be anybody's type—even blind men!
"Just take my word... Continue»
Posted by freegre 7 months ago  |  Categories: Anal, First Time, Shemales  |  
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My one and only experience with a tranny/shemale

One Friday night I decided to take a ride to Hollywood to check out adult theaters as i had always gotten my cock sucked at different adult movie theaters. As I parked my car on a side street i walked to this one particular movie theater I found myself at entrance and paid the 5 bucks to enter. as you all know, when you go into any movie house, its always dark and you wait for a few minutes for your eyes to adjust to the surroundings. i was standing near the entrance and looked around to find an empty seat. i always look to find one in the back near the isle, but they were taken, so i went... Continue»
Posted by 1superhornyguy 2 years ago  |  Categories: First Time, Mature, Shemales  |  
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On the road

Dannielle had decided to finish work at dinner time and go for a drive the long way home seeing as the day was so nice. As she got into her car she thought "i will put the soft top down and get a tan". As she got in the car she looked at herself in the mirror and checked her make up, hair and her top. She had noticed how the boys in the office had been looking her up and down during the day, well she had dressed for the attention. Her tight white top that showed her black bra off really well and her short black skirt that was so tight that you could notice the outline the suspender belt she wa... Continue»
Posted by danni1 4 years ago  |  Categories: Group Sex, Hardcore, Shemales  |  
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Dad uses me for his wife

After a long and unstable marrage of 20 years, the divorce papers finally came. My wife and I only had one c***d, William, and he is very gay. My wife was too much of a homophobic bitch to support him. Even when he was younger we knew he would turn out gay. Always wanting to wear girl's clothing, dress differently, speak differently, even walk differently. I always supported him as a dad and as his friend. I never understood and I still don't understand my wife and how she could just leave her only c***d and I. I remember it was his 18th birthday, about five months ago. She came home from work... Continue»
Posted by nicoleinberlin 2 years ago  |  Categories: Gay Male, Shemales  |  
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Schoolgirl Sissy Crossdresser and Her Black Daddy

WARNING: This fictional story contains graphic sexual/profane terms and scenes. This is a work of fiction, a fantasy, and is meant to be enjoyed by horny fucking perverts like myself.


I can't believe this is happening right now. Here I am, a 16 year old white boy dressed in the sluttiest schoolgirl costume and makeup I have ever seen, being barebacked by an older, married black man. How'd I get so lucky?! Let me start at the beginning...

It was summer time. As always I spent my summers hanging out and occasionally mowing neighbors lawns for some extra cash. Although I wasn't exactly th... Continue»
Posted by AllisonCumms 2 years ago  |  Categories: Anal, Interracial Sex, Shemales  |  
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My First BBC

It was not long before I told my wife about who I really am, that I was having serious desires to be taken by a real man. I have / had no true preference, but something about getting pounded by a cocky and arrogant black guy really turned me on. But I wasn't looking for some thug or prick to just have me. I wanted a man!!! A black man.....a BBC man!!! One who had a hot bod, aggressive demeanor, and of course a huge cock. So I had my expectations, and I was anxious for this experience.

I had been dressing in full for a while at this point, but my wife wasn't actually aware. Porn was... Continue»
Posted by Ivygurl86 3 months ago  |  Categories: Anal, First Time, Shemales  |  
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First time giving a blow job.

I was a bit younger than I am now when I met a boy a bit older than I was who just caught my attention. He was a closet gay, I was bi-curious. He was so attractive. 6'1", 80kg, tan, short hair, brown eyes with a great fashion sense. For now, we can call him, Joey.

My friends and I were out clubbing one night when we stumbled upon Joey on his own at the bar. My friends were more interested in dancing, but I wanted to sit with him and see what was up.
We chatted about minor things like school, parents and our sexuality. He was the first person I told that I was curious and I was the first to... Continue»
Posted by ShulaV 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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My First Night of Being a Sissy Cumdump

Well I first started dressing when I was about 14. One thing that I always noticed is that putting on slutty clothes makes me an absolute whore for cock and cum. Throughout High School I dressed in my alone time but never acted on my slutty urges from fear of being caught by my parents. When I moved to college that all changed though. As soon as I got settled into my private dorm room, I thought it would be nice to spend the evening dressed like a little slut. I decided to wear my schoolgirl outfit that night. So I took a nice hot shower and shaved myself smooth from the neck down. I went back... Continue»
Posted by cumslutchloe 1 year ago  |  Categories: Anal, Hardcore, Shemales  |  
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My New "Girlfriend"

Let me introduce myself. My name is Kevin, I'm 23, I live alone in a two bedroom apartment and I work full time as a store manager. My last relationship lasted 3 years and we were together since high school but both of us split about a year ago. 

It was a long day at work today so I went to a local bar to hang out and meet hot single women. Once I arrived at the bar, I could see three hot looking women glancing at me, checking out my slim, somewhat muscular body. I walked over to one of the prettier looking ones and I said, "Hey beautiful, can i get you a drink? She replied, "I don't know..... Continue»
Posted by adblman 9 months ago  |  Categories: First Time, Masturbation, Shemales  |  
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Dirty TS Supprise

True Story I'd been out drinking with a few mates first the pub then we hit the clubs. It was late and I had work then next day so left my mates and went to get a taxi home. walking up the street for a taxi I noticed a woman standing on the corner. The girl was facing away from me but looked hot from behind short skirt, fishnet stockings and high heels looked like a total slut my kinda girl. As I passed by she asked if I had the time of course I stopped and used the oppertunity to chat her up. She was stunning long dark hair brown eyes and tanned skinned after chatting for a few minutes she as... Continue»
Posted by crbigboy 3 years ago  |  Categories: Anal, Hardcore, Shemales  |  
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My first time-an unexpected pleasure

I spent the summer of 1983 in New York with my dad and stepmom. I was 18 and was in between my freshman and sophomore year of college. I had a cool job as a bank messenger on Wall Street and plenty of time on my hands. I used that time to hang out in Times Square which, at that time, was porn heaven. Many hours were spent looking at all kinds of loops in the peep booths. Everything from guy/girl, lesbians licking and sucking sweet pussies to shemales and crossdressers. I had seen my first shemale photo spread a couple years before in an issue of Hustler and was instantly intrigued and turned ... Continue»
Posted by Blackpapi65 8 months ago  |  Categories: Anal, First Time, Shemales  |  
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MY FIRST SHEMALE ENCOUNTER

I remember the first time I found myself in bed with a shemale. I had just broken up with my girlfriend. I was lonely, I was horny, and
I had zero intention of finding myself in another relationship with a woman. When I told my buddy, Bob, he told me he knew just where to take me to solve this. So he took me to this club over in West Hollywood. The place was FULL of gorgeous women. My head was swimming - they were almost all slender and dressed in very sexy attire. Short skirts and sheer nylons everywhere.
"Wow!" I told Bob. "These chicks are all drop-dead gorgeous. What's the catch? Are the... Continue»
Posted by madnessx 3 years ago  |  Categories: Anal, Masturbation, Shemales  |  
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my aunt made me a transvestite

My aunt and uncle lived two doors down from me when I was growing up. They had a son one year younger than me. We played together all the time and I was at his house or him at mine all during the summer months. My aunt was a big woman, she was 6ft. tall and weighed around 165. She was even taller in her 3 inch heels. She had long auburn hair with beautiful waves in it. She wore a 9 1/2 shoe. Her hands and feet were large, but so sexy looking with nail polish on. Her blue eyes would melt you. She had a great mirrored vanity she would sit at for hours and try different combinations of makeup. Sh... Continue»
Posted by momandboys 1 year ago  |  Categories: Fetish, Shemales, Taboo  |  
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Moms sissy becomes a young slut for a black man

I have always loved the feeling of something lacy or sexy on my body. I call it a passion of some sorts, wearing these things made me feel very special and desirable. I was raised by my mom and the closest f****y we had was my Aunt Trish and her two daughters. To start my collection of these things to wear, I would take things they left lying around the house and later claimed as my own since I assumed they were things that were lost. My mom was always working or going to my aunt's house on the beach for the weekend. I never was a problem k** and always made good grades in school. Mom never re... Continue»
Posted by momandboys 1 year ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Sweet and salty

I was very down after my divorce, I started thinking of ways to subside the heartache. Talking wasn't enough, I needed something more. While I was waiting for a friend to get off work at his bar a lady approached and asked to buy me a drink. She was about 5'9", long red hair, and smelled so sweet with a smile that eased my heart; how could I say no. We sat at the bar long after closing several drinks in and a few laughs; she ask if I wanted to back to her place. Once again, how could I say no.
I told my friend I'd talk to him later and followed her back to her place. We arrived this nice li... Continue»
Posted by jimwinslow1982 18 days ago  |  Categories: Fetish, Shemales, Taboo  |  
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He caught me in his wife's cloths

I do odd job's and I was about to do one for my wife's best friend Tina and her Husband Phillip. I went over and looked at the job. I told her it would take several days and that I could do the work while her and her husband were at work. That way I wouldn't be in anyones way. Well the first day of the job I showed up just before Tina left for work. Pillip was already gone. We chatted a while the she left for work. Tina is really very hot and I have wanted to fuck her for a long time. Sense i knew that was not going to happen I thought I would do the next best thing. I went stra... Continue»
Posted by firstknightd 4 years ago  |  Categories: Shemales  |  
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