Momma's Sissy Boy free porn video

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My name’s Sam but you can call me Samantha, that’s what my mom calls me. When I ask her why she says because she loves me like I’m her little princess, regardless of me being a guy... Well the most manly thing about me is my penis and that’s not that big.

I was born with a severe case of Kleinfelter's syndrome meaning I have very pronounced female features. I have large, round juicy hips and thighs, my ass is big round and perky like a bubblebutt, my boobs are a cup B size and my face looks like my mom’s. She also has the same size hips, ass and thighs but her boobs are larger, 2 cups larger than mine.

All my life I’ve been inside. Mom always said “the world is not ready to see how beautiful you are jus t yet” I’d still go out to the nearest corner shop but no further or for too long.

Most of my clothes are made up of loose silky shirts that my mom said are made especially for me and all of my pants are tight fit. My wardrobe looks about the same as hers except for the dresses.

My mom says “underwear doesn’t fit me like normal boys” so, to save herself the expense, me and her share panty drawers. Other underwear that I see some of the guys wear in movies would never slide up my thighs like girly ones will, that’s what mom says too. Our panty drawer consists of different shapes and colours ranging from normal panties to thongs and G-strings in all girly colours because my mom picks then out.

To hide my boobs my mom gets me sports bras that are all pink. She also brought me normal bras that girls wear but I want to draw a line somewhere with all the girly stuff. I wear mostly the pink sports bras so the other, large pile of normal bras are folded nicely in my wardrobe.

Me and my mom are same height and foot size so we share shoes. When I’m at home which is always, she makes me wear high heels. She says they look pretty on me and she loves it when I look pretty.

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Crowd Sourced Sissy 2

PREVIOUSLY ON CROWD SOURCED SISSY: A man meets 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. The guy decides that he wants to/needs to join her as a willing-to-do- anything sissy, so he starts his own website. He will become a perfect sissy by doing whatever his online fans demand. Crowd Sourced Sissy 2 My trip...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm 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 Doctor Shirley Williams. 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 Jamie Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen 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...

2 years ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told...

1 year ago
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A New Sissy Maid

Chapter 1 It was a sunny, summer’s day as he walked up the front path to the unknown house, pulling a rolling suitcase behind him. It was really too warm to be wearing a turtleneck sweater, but bearing in mind what was under it, he really knew he did not have a choice. His heart was beating furiously, he was sweating, his palms were moist and his mouth was getting drier by the second. He had never done anything like this before. Well, he had come this far. No turning back now, he told himself,...

3 years ago
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The Sissy Diaries My Two Mistresses

Dear Diary, Things were going so good for me. I got promoted at work, even though I know most people there don't like me because I'm quiet and reclusive. It's just that I can't get too close to anyone there and risk exposing that I'm a closeted crossdressing sissy. Still, I do my work and go home to my apartment and escape into my sissy world. Still, I decided that with my promotion and my increase in salary, I could afford a better apartment in a better neighborhood and that's where...

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