Shemales Porn Stories
Page 5

FUCKING UNCLE BOBBY

The title of this story isn't really accurate as I wasn't fucking Uncle Bobby see Uncle Bobby was fucking me! He wasn't really my uncle he was just my mother's boyfriend but he lived with us so it was kind of like he was my Dad I really like him a lot he gave me lots of attention and took me places and gave me money for doing chores for him he really was a good guy! He had a boat and it was a nice one too he kept it docked at the Marina and one weekend he asked me if I wanted to go fishing with him well I loved to fish and I loved boats so hell yes was my response and we set out to go fishi... Continue»
Posted by laceysgirl 2 years ago  |  Categories: BDSM, First Time, Shemales  |  
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My Shemale Mom and Aunt



I'm 5 feet and six inches tall I weigh 135 pounds soaking wet with long brown hair. Mom and Auntie Karen are both 6'2" with huge breasts and long legs. I walked into the Den to see them watching some shemale porn together. I sat down across the room from there with trembling knees and tears running down my cheek on the right side. Mom said come and sit down next to us, so I crossed the room and sat between them they both kissed me on the cheek and said We have a confession honey.

Timmy I'm not shocked that you wear my underwear I just wish you had told me.
You see I guess I only have m... Continue»
Posted by sissytimmy 2 years ago  |  Categories: First Time, Shemales, Taboo  |  
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Discovery

"What the hell are you doing!!?" I heard my s****r scream. My eyes snapped open, my hand flying away from its grip around my cock. With our parents away and my s****r out I'd thought I'd be alone for the evening and decided to have a wank. Now Michelle had come home unexpectedly and discovered me. It got worse. "Are those my knickers you're jerking off into?" She screamed again. I nodded shamefacedly. "You little shit. I'm telling on you."

"Please don't Michelle; I'll do anything you want." I pleaded.

She looked down at my lap where her panties were still wrapped around my now wilting ... Continue»
Posted by sparkyking 2 years ago  |  Categories: Shemales, Taboo  |  
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High School Cocksucker Outted (another story)

When I was 16 I slept over at Kyles a lot. Mostly I slept over because he'd fall asl**p while we were playing video games and watching tv. It was up to me whether I stayed and slept or went home. Kyle is black about 6'2 and has a strong build. He has a white Mother (Molly) and a black father (Wayne). He has a s****r named Jazyln who just entered high school. She has her mothers facial structure and a tight little body with breasts that seem to spring over night to about a large B cup. She was sexy and I always had to be careful when I was checking her out. Once or twice I caught her coming out... Continue»
Posted by Msgrv32 2 years ago  |  Categories: Taboo, Shemales  |  
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Back to School

Back To School
Nikkie Silk

I was so excited. This was going to be the first day at my new job. I had recently been appointed as the receptionist and administrative assistant at the local Elementary School. I set the alarm to wake me up early, so that I could get ready and make sure I would be on time. I was excited but also nervous. I had yet to meet my new boss, Mr Michaels, the Principal of the school. I had been hired by his deputy, so I would be meeting him for the first time today.

The State had just enacted an affirmative LGBT action hiring program. This meant that as a pre-op tr... Continue»
Posted by nikkiesilk 4 months ago  |  Categories: Anal, Shemales  |  
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My Big Sister

I must say I never pictured this event happening to me in my lifetime, I mean I'm a pretty well rounded k** living in a quiet suburban town. Nothing big happens here, and I'm not some guy that's always finding himself in trouble, so getting bent over and fucked in my ass was the last thing I really worried about, unless I was gay of course, which I'm not.

But no, here I am at eighteen years old, a grown man feeling his ass burning as I try my best to sit comfortably at my desk. As the instructor goes on and on I find my eyes darting back and forth around the room, making sure no one looked... Continue»
Posted by sparkyking 2 years ago  |  Categories: Shemales  |  
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Shemale massage

It has been one of those long and stressful weeks. I’m in desperate need of relaxation and relief so I head over to an Asian massage parlor for a typical happy ending massage.
The girl who usually massages me isn’t available so another girl is suggested which I accept. I think to myself that she can’t be much different than my usual so I don’t care much. I just need a massage badly.
She comes out of the back from another massage and introduces herself as Jessica. I smirk a bit knowing there is no way her name is Jessica but I go with the bit and am happy as she is quite attractive and alread... Continue»
Posted by malesub01 2 years ago  |  Categories: Shemales  |  
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Young sissy loses her virginity (true story)

So this is a true story about the 1st man that I ever met. I was about 13/14 years old and had been talking to a much older man over the internet. He was about 50 if I remember correctly.

I had been dressing in my mother’s underwear and dresses for a few years and found it so sexy, I had not considered myself gay or bi, I just knew I belonged in female attire, it made me happy and felt natural.

The thought of pleasing this man made me excited, terrified and scared, but very excited. I could tell from my little clitty. After chatting for a few hrs he wanted to meet me?

I had never me... Continue»
Posted by Subtvnicola 1 year ago  |  Categories: First Time, Shemales, Taboo  |  
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my friend's new roommate and her surprise

So my friend Rebecca and I were planning on going to this bar for the evening but she called me and said she was running a bit late and that I should wait at her place and that her new roommate Shawna should be there to open the door for me. Rather, than wait in my car I went upstairs to her apartment like she suggested. The door was slightly open so I walked in saying hello; to see if anyone was home. I heard some noise in the kitchen so I walked over to check it out. It was Shawna cooking. She was actually a pretty cute girl. She was wearing a white tee shirt that just about covered her ass ... Continue»
Posted by pleasurenfun 3 years ago  |  Categories: Anal, First Time, Shemales  |  
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Summer transformation Part 1

My jaw hit the floor as I read the first email I ever received from John. My mind twisted, heart raised, and my pussy pulsed repeatedly.

A week earlier I had posted an ad on craigslist... One of those late night d***ken fantasy ads where you spill your darkest desires, wake up the next morning and think "wow... I really am a pervert!" My ad was placed M4M, M4MM, M4MW, and T4M. I wrote:

" 18 year old looking to experiment. 5'5", 170, naturally smooth. School is out so I have lots of free time, super horny all the time, looking to learn. Discretion is a must, can`t host, love mature ... Continue»
Posted by archerfan88 4 months ago  |  Categories: First Time, Shemales, Taboo  |  
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My First Time Dressed as a Girl (PT 3) (Consequenc

Well. I had written a follow up to ‘My First Time as a Crossdresser, PT 2” but Microsoft decided that the moment I attempted to upload was the perfect moment to update and erased the whole story, which means I had to rewrite the whole thing. So...

After I dressed in the schoolgirl outfit that Gunther had put out for me, I pulled my hair into a high ponytail and put on makeup emphasizing my eyes and lips without going overboard. I walked out into the living room to discover that Tracey had left and Gunther was dressed in a pair of slacks and a very expensive looking Cashmere cardigan. He s... Continue»
Posted by sbobbi66 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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First Blowjob

I pulled into the reststop needing to pee badly. As I walked into the restroom, I spoke briefly to a trucker, and went about my business. While I stood there peeing, he took a peek at my dick. At the time, I hardly even noticed it.

As we went to leave, he said he was going the same way as I was and would be monitoring his CB radio for reports on where cops might be. He then invited me to follow him. I agreed since I wanted to make good time. We drove for about an hour when he pulled over. I thought maybe something was wrong so I pulled over too.

He got out and walked back to my truc... Continue»
Posted by KaylaCD15 1 year ago  |  Categories: First Time, Gay Male, Shemales  |  
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Caught by the Neighbor Crossdressing While Home Al

Do you know a crossdresser who got caught in the act?

This is a real life story of a crossdresser caught in the act!

This happened around when I was 15 yrs. old.

As my s****rs were off at college and it was just my mom and I at our apt. I was home from school as we didn’t have any school that day. But my mom was still at work. So I got myself all dressed up looking pretty. As I thought I will make it a girl’s day in. I decided to wear a pair of my mom’s dark navy pantyhose with one of my s****r’s jean skirts and a blue and white sweater with some black 3 1/2 heels.

I put my ma... Continue»
Posted by sparkyking 9 months ago  |  Categories: First Time, Shemales, Taboo  |  
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My Ex-Girlfriend's Mom

My name is Bobby. Before I tell this story, let me set it up by telling a short story first.

At the end of my senior year in high school and into the beginning of the summer, I dated a girl for a few weeks but never got past making out with her. Her name was Jill. One weekend Jill and her mom, Lana needed to leave town and asked if I would check in on things at their house. I did as they asked and once, while I was there, I got on the computer and watched some porn, shemale porn.

A few days after they got back, Jill and I got into an arguement and I broke it off with her. She tried calli... Continue»
Posted by naughty_bi_interest 4 months ago  |  Categories: First Time, Shemales  |  
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Going to the Gym

“I’m headed to the gym, baby,” the six-foot-three-inch two-hundred-sixty-pound Black man said to his wife of seven years.
“Ok,” she replied barely looking up at her beefy, brown-skinned husband. “I’ll be at the hairdresser by the time you get back.”
“Alright. See you later,” Darius Woodham smiled.

The former Division One linebacker started his black metallic 2012 Ford Expedition and backed out of the driveway. At the end of the street, he stopped at the intersection and pulled out his phone. He sent a message to the person he was heading to see.

Three months prior, Darius was watching ... Continue»
Posted by faggyboi 7 months ago  |  Categories: Gay Male, Interracial Sex, Shemales  |  
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Brittany The Cheerleader

It was my second year as an assistant counselor at River High School. I was young, in my mid twenties. Everything was typical in the small town school. I would help students with scheduling issues, direct them towards colleges, and help them with different scholarships and programs that would benefit them. It was entirely unremarkable and nothing out of the ordinary happened until I met Brittany.

One day a woman walked into my office. She was tall for a woman of her age, yet very slender and petite, with an almost non-existent chest, gorgeous round bottom, tanned skin, and long deep brown... Continue»
Posted by wedgietime 8 months ago  |  Categories: Fetish, Hardcore, Shemales  |  
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Becoming the neighbourhood slut

The following is a fictional story but mixed up with some real experiences and a few of my actual desires :)



The first real days of spring were finally upon us. This was extra cool since I would be alone for a week or so. I took a few days off of work too, so I can spend the time dressing up at home and possibly try to find some real fun too.

When I got a few free days I always did the needed grocery shopping in the morning so I have the rest of the day completely free to dress up and stay dressed up. I usually went to a shop nearby, grab the needed stuff quickly and go home.

I di... Continue»
Posted by analhottie 1 year ago  |  Categories: Anal, Fetish, Shemales  |  
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Fun with the Mechanic

Last weekend, I had a date to go out to a bar with some other CDs in another state and a 2 hour drive. I would get dressed when I got to the motel. On the way I had car trouble, but kept driving to the motel. Told the girls who were already dressed that I couldn’t go to the bar or play because I could not relax knowing my car was having problems. I was so horny because we had set this date up a few weeks ago and I had spent the day trying on my new sexy short black dress and getting ready.

I left the girls at the motel and headed home with the car having transmission problems. On the ... Continue»
Posted by hotcdsub 1 year ago  |  Categories: Fetish, Hardcore, 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 1 year ago  |  Categories: Gay Male, Mature, Shemales  |  
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mommy's new girl

It's true that I had become accustomed to drama in my f****y. My father was loud and mean, especially when he was d***k, which was most evenings and every weekend. He would back my poor mother into a corner of the kitchen and berate her, towering over her in that threatening way that I knew so well, telling her she was fat and ugly and stupid and spending too much money on me. He would get louder and louder until she finally began to tremble and sob – then he would storm out of the house in disgust, as if her crying gave him the right to leave his "silly emotional wife" and visit his drinking ... Continue»
Posted by momandboys 2 years ago  |  Categories: Fetish, Mature, Shemales  |  
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