Shemales Porn Stories
Page 15

becoming a slut

It all started when I was 13 and discovered the joys of wearing women's clothing. It started with my older s****rs panties then my highschool girlfriends things by the time I was 18 I had a pretty good collection of womens clothing even with never having the nerve to purchase any of them myself. Then came the urge for more when dressing up and masturbating wasnt enough I wanted more. I always considered myself straight despite my crossdressing but when dress would get the urge to please a man. So one day I got my s****rs 7 inc dildo. I got dressed up in some sexy thong panties some nylons and ... Continue»
Posted by RenoBoi 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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The Truckers Reststop

I had to work yesterday, it was Saturday,I had made plans to spend the day being the slutty little whore for the whole day, but work got in the way. I came home felt tried so I soaked in the tub, shaving my legs and puss yass and gurly clit. The weather was bad all day, when I finally decided to Fem myself up it was already 8pm, so I thought what the heck I'll drive up the Interstate just north of Seattle to a truckers rest stop I have gone too before. The weather had cleared up a bit, so I was hoping for some fun. I dressed in my short wrap around skirt, red thong panties, red Bra, and a shea... Continue»
Posted by cd_lorretta 4 years ago  |  Categories: Gay Male, Shemales, Voyeur  |  
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Sex with teacher(sissy)

I was the 2 year of high school back then. My grades werent going realy well moastly becuse i spent most of my freetime blowing guys,and sticking thing in my ass,then studying.My parents one day decided that i need some extra classes,so they hired a tutor. I wasn't realy up for that idea,but they somehow talked me into it. After a while it was the time for me to have my first class. My parents left for work,and i was home alone waiting my teacher.Then the dorbell rang , i felt so nervous as i opened the door. In walked a handsome 25-6 year old man,fresh out from college,in a very nice suit. We... Continue»
Posted by sissygirl1988 1 year ago  |  Categories: Anal, 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 8 months ago  |  Categories: Anal, First Time, Shemales  |  
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My first time being taken dressed as a woman

I'm a 42 year old married bisexual guy, slim built, average height and shaved below. Ive had a few encounters with other men but none dressed as a Woman.
Ive had fantasies for years about wearing women's clothes and make up. Unfortunately I haven't had much opportunity for either, that was until a few months ago.
As it turned out my wife would be away for 3 weeks and opportunity presented itself. I quickly got down to planning and slowly but surely a plan came together, well sort of anyway.

I went online and ordered some womens lingerie, wigs, panties, make up and a few slutty costumes, ... Continue»
Posted by jimbo70xyz 2 years ago  |  Categories: BDSM, First Time, Shemales  |  
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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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she trained me

I was sent to Aunt Fergie when my parents were killed. She is about 5'7"
and 200 lbs she was your stereotypical aunt with some fat and wide hips and
big breast. She picked me up at the bus station in her car.

She said," My household is different and special I have girls who you
will find are very unique. I too am unique and I will show you what I mean
when we go home."

We rode for a half-hour and we arrived to her big old which I would find
was an old Victorian with a widow's roost on top of the roof.

She e****ted me to the bedroom that would be mine and told me," Put your
... Continue»
Posted by pcarter 3 years ago  |  Categories: Anal, Fetish, Shemales  |  
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SOMETHING ABOUT DANNY

What was it about my daughter's boyfriend that turned me on so much? No one characteristic comes to mind. I suppose it was a combination of things. And perhaps a certain time in my life also. I was 52, divorced, alone and quite bored.

I had been divorced from my husband Jerry for 12 years and didn't really have a steady boyfriend. Jerry and I remained friends but he seemed to be turning into an old man. I was still young at heart, or so I felt. But the more men I met the more disappointed I became. It had been getting to the point where I would rather stay in my apartment and read than go o... Continue»
Posted by couple_kinky 2 years ago  |  Categories: Fetish, First Time, Shemales  |  
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Frank's Friend

Frank is a buddy of mine. We grew up and went to college together. While we were in college Frank and I went on a road trip from Lubbock to Dallas. We got to Dallas went to a few strip clubs and then finally found ourselves on Harry Hines Blvd. It was about 1 in the morning we were both horny and a little d***k. Frank pulls up to this leggy blonde in a short skirt and fishnet hose and asks how much. She told us she would do us for free for a ride home. We said fuck yes. Frank had me drive to her house while he had her in his lap, kissing and groping her. We got to her house and went i... Continue»
Posted by biguy52x 2 years ago  |  Categories: Gay Male, Group 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 4 months ago  |  Categories: Anal, First Time, Shemales  |  
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The Tgirl Hooker

All my stories are based on real life experiences.

I spent a few weeks looking at e****t sites, reading reviews, services, likes & dislikes, pictures... until Emma caught my eye.

Emma was Eastern European, had a tight slim body, blond hair, very fem and a nice cock. I wasted no time and contacted her to set up a visit and within a few hours she replied and we discussed what I wanted.

The day soon arrived and I was quite nervous through excitement. I had visited e****ts before but never a Tgirl. I pulled up to this house in a normal road and knocked on the door, and there stood Emma i... Continue»
Posted by dirtydisco99 1 year ago  |  Categories: Anal, BDSM, 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 10 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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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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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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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 9 months ago  |  Categories: Anal, Fetish, Shemales  |  
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True story of an old man in the woods

I was just a young lad the first time i did any thing with another guy, i was still living with mom in the house she inherited from her father after he died in a small village that mainly had elderly people living in it.
There certainly wasn't any one my age about so contact with other youth's was limited to school.
Most of my time was spent playing alone or helping mom about the house, then some thing happened that was to change me for ever.
It was a Sunday morning and mom was home doing some house work, i was watching cartoons on the TV when she called to me to help her get the washing in... Continue»
Posted by fun_boy_fan 3 months ago  |  Categories: Gay Male, Mature, Shemales  |  
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My "special" employee

I am recently retired from a profession that has to be one of the best in the world: I was the owner and operator of a 100' charter vessel that worked in Alaska. It was a high end operation that never took more than 12 passengers, there was a crew of 15, and we would spend 7-15 days exploring some of the most beautiful areas in the world. My passengers were typically 50 years and older and wealthy. Occasionally I would get much younger people as well, and they would be m/f couples, m/m, and f/f.

I traveled the waters of Alaska for over 20 years, and had many exciting and satisfying exp... Continue»
Posted by 1kaboom1 29 days ago  |  Categories: Fetish, Shemales, Taboo  |  
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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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