The Becumming Of A Sissy - Part 1 free porn video

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Tonight is the school play of Moulin Rouge!, and i get to dress up as a beautiful woman. Make-up. Dress. Stockings. The lot.

Drama was never the most popular class for the final year, so they needed the extra woman character to be filled by one of the boys. Me. It's not a big role, i don't have many words because my acting sucks. But its going to be a great chance to explore that little more. My mum and her brother (Uncle Gareth) and sister (Aunt Carol) will be coming to watch so i got to look my best. My cock is all tucked in, i have my black lacy thong and bra on, my stockings pulled up, and my hot red short dress fitted nicely around my slim body, and my hair wrapped in cute pigtails. One of the girls did my makeup for me, its one thing that i still really practice with. Lips red, eyes dark and I'm ready. I looked hot!

The play had ended, and I decided to keep in my outfit for the ride home. I felt great. My blood was pumping and i felt alive.

Mum was sat in the front with auntie, and Uncle Gareth rode in the back with me.

The music was on and Mum and Carol were talking amongst themselves.

Uncle leaned over to me and whispered "You were fantastic tonight, I honestly didn't know that was even you for half the show"

"Thank you my love" i replied, playfully keeping in character "what was you favourite part?"

"All of it, you make a pretty good looking girl" he chuckled.

"You think? all these clothes are pretty comfy, even the thong and stockings" I laughed.

His eyebrows raised "Thong and stockings?"

I laughed and lifted my frock a little higher to show him the stockings, I could feel his interest, and i honestly wanted to show him.

"Wow....those. Are pretty hot, are they yours?" He nervously asked.

"Yup....I bought them especially for the play" I could feel his eyes searching. I looked back, i could see him getting a little raised in the crotch area and my heart jumped.

I opened my mouth in surprise when i saw the bulge. My eyes were focused on it.

He saw that I saw and placed his hand on my thigh, he looked at me "Its ok" he said "Take it as a compliment"

I looked back and smiled "Ok Uncle Gareth" and bit my lip. I've never thought of anyone this way before, sexually.

He gave my thigh a firm squeeze, and looked to see if the two in the front was paying any attention. He leaned a little closer.

I could feel his breath on my ear. "Maybe i could get a private show in that outfit sometime"

I didn't say anything, just looked back at his intensity.

We arrived home. In all the excitement I'd forgotten my phone.

"Damnit......I forgot my phone Mum"

"Oh dear, Carol can you drive us...?"

Uncle Gareth interrupted "I can take him back, you guys catch up we'll be back in no time"

He looked at me and smiled, and nodded his head for me to jump in the truck.

We began the drive back. Just the two of us. We didn't say a word, he was stroking my leg lightly along the way and i could feel myself getting hard.

Before i knew it we stopped. It was dark but i could tell we were not at school. He looked at me.

Gareth was a well built guy, about 6ft and strong looking. He placed his huge hands on my chin, gripping me lightly, rubbing his thumb across my red lips.

I took a deep nervous breath. He place his massive thumb inside my mouth, and i instinctively sucked and he welcomed the action by pushing it in and out.

"Fuck, i'm so hard" He grunted, and pulled his massive cock out of his jeans. It was huge, probably about 10-11 inches and really thick.

His hand placed on the back of my neck, "Come on, put those lips to good use you slut"

I couldn't believe he called me that, and before i knew it his hand pushed my head down to his lap, and my mouth landed on his cock.

I didn't know what to do with myself but his hand sure helped me along, gripping the back of my hair and forcing my head down. The cock going into my mouth reaching the back of my throat.

Before i knew it, his hand was no longer there, i was pushing it down myself. I couldn't believe what i was doing.

"You're a natural, you done this before you fucking slut?"

I tried to reply, but i couldn't stop myself. So it just came out as multiple gagging noises.

I assumed he loved the sound of me gagging as he soon shot his load straight into my mouth. I swallowed the first load, and then the second, with the third one then streaming down my chin.

"Good girl" He whispered. I smiled, with his load visible on my chin. That was incredible. I couldn't imagine ever doing anything like this. And with my uncle all the same.

I felt his hand touch my crotch. As he brought his hand up, more cum. He pushed his cum covered fingers into my mouth. It tasted a little sweeter, not his.....but mine.

"Such a dirty whore" He grunted, this time he got out of the car. He came to my passenger side, opened and pulled me out.

He placed me at the front of him, hidden out of sight, on my knees.

His cock was rock hard again.

He grabbed my pigtails and began to force his massive cock in my mouth. I didn't stop him.

He quickly picked up the pace. Forcing deeper and deeper each time. Thrusting harder.

My throat was now being aggressively fucked. and i loved it.

I was gagging constantly, getting in my breath when i could. I threw up a little on his cock which only made him go harder.

He pulled out "Stick out your tongue sissy slut", and i gladly did what he said.

He then unleashed the thickest load I've ever seen. One stream went across my noise all the way to my hair. A second landed in my mouth half dripping off my tongue. And the rest covering my eyes.

I was in heaven.

He gripped my throat and whispered "You're mine", I came on the floor at that moment.

He pushed my head to the ground and made me lick it up like a dog when his finger pressed into my ass.

I like where this is going.

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SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Slumber Party

Sissy Slumber Party I was on my way to the slumber party and I was so excited that my panties were getting wet. As I felt the moisture between my legs I blushed and giggled. My high heels clicked on the sidewalk as I went and my full skirts and petticoats swooshed around my baby smooth nyloned legs. I wiggled down the street and my long curly hair and bangle earrings swung from side to side as I walked. Some men in a passing car whistled at me and I just smiled. But my panties...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

3 years ago
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The Reawakening of Sissy Jackson

The Reawakening of Sissy Jackson By Cassandra Morgan The memories came at night, when his consciousness was not on guard to stop them. A little boy, rushing across the playground to his mother. She laughs and picked him up, kisses him on his lips. He is a small boy, frail, too weak to play ball sports with the other kids. He plays on the swings...but not too high. He plays hopscotch. He plays jump rope. The mommy does not care. She likes having her little boy close to him, and if...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

3 years ago
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The Farm School Sissy

INTRO (Skip this bit and get on with the story if you want) Like most of my writing projects this is unfinished. I seem to always get obsessed with small details to the detriment of ever finishing the work. Feel free to take over this story yourself and make it what you will. This particular story is set in a world perhaps just slightly off centre to our own. The location is a boy's only orphan farm school run mostly by strong and independent women. The world has changed in so much...

2 years ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

2 years ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

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