Crossdressing Sissy Desires Part 1 free porn video

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I always knew that I was a submissive little sissy. Ever since I was little.
I would raid my mother's panty drawer while she was away at work. I would
always look for the pretty colored ones and ones with lace. They felt so soft
against my smooth ass and sissy clit. I would run to the bathroom with my arms
wrapped around panties of different varieties. As I locked myself in the bathroom I could feel
my sissy clit throb and drip pre cum. Quickly, the clothes of my pretend life would
find their way to the floor. My real life clothes were the panties I held onto so tightly.
One by one I would slip into them. Taking pictures of how they made my ass look.
I knew that one day I would be blessed with a cock pressing tightly against the soft
fabric that hugged my sissy waist so gently. I would practice arching my back for my
future master to enjoy. I loved bending over the bathroom sink, pretending my master
was behind me pounding away, filling me with all of himself. My sissy clit so ready to
explode with pleasure. One touch was all it took to fill my hand with cum. I forced myself
to swallow it all. Pretending it was daddy's cock juice.

As I got older, cruising through the internet to find my daddy was an everyday mission.
Hundreds of emails came and went. Pictures of cock from the emails filled my computer
and I wished so bad that I was the one being filled. Finally I worked up the courage to meet
an older gentleman who would ease me into the life of being a sissy.

It was late at night as I walked over to his house. Panties under my shorts. I couldn't stop my
sissy clit from throbbing and dripping. I knocked on the door, this was it, I could turn around and
walk away but I hungered for cock. He opened the door and with a smile he invites me in. He leads
me to a dimly lit room.
"take off your clothes" He says
I don't talk, I just do as he says.
As I stand there naked with nothing but panties on, I feel my nerves start to build.
"nice panties" he says with a smile. His shorts slip off, exposing his cock. He starts to slowly stroke
himself. My mouth begins to water.
"have a taste" he says as he looks at my lips.
Right at that moment, my nerves were calm and I dropped down to my knees.
I took his hard cock in my hands and heard him groan.
I then wrapped my lips around his head, he let out a moan.
"oh fuck, that feels so good" he groaned.
This made me happy. My sissy clit was hard and dripping. Making a wet spot on my panties.
He put his hand on the back of my head and began to fuck my mouth the way he wanted.
Shoving his cock against my throat. Making me gag.
I wanted to taste his cum right then and there. But he brought me to my feet, turned me around
and gently shoved me against the wall.
His hands on my ass, squeezing and spanking me. With each spank, my heart skipped a beat
and I would let out a tiny gasp.
He pressed his hard body against my back, pinning me against the wall. I could feel his hard hot cock
pressing against my ass. His fingers found his why to my tight hole and he danced around it until he
finally forced his finger in my sissy ass.
He fucked me with his finger, and I could feel my sissy boy pussy opening for him.
I arched my back just like I've been practicing. Pushed my sissy ass toward daddy, inviting him in for more.
He pushed my panties down, gave my ass a spank, and began to rub his cock up and down against my sissy boy pussy.
"stay right there, don't you move" he commanded. And I followed orders.
I felt cold lube fall on my ass followed by fingers massaging the lube around my tight hole.
"you're such a good girl" he said happily
The smile on my face quickly turned into a loud gasp for air when he shoved his hard cock
into my tight wet hole.
"oh baby you're so tight. you feel so fucking good" he moaned.
I pushed my sissy ass toward him and he pounded away. In and out, I could feel his cock fill me up.
With each thrust I could feel myself turning more and more into a sissy slut.
One final hard thrust and he pinned me against the wall again.
"get face down on the bed and put that sweet ass in the air for me" he commanded again
"yes daddy" I said with a whimper.
I walked over to the bed, laid down, arched my back with my sissy ass in the air for daddy.
He stood there holding his cock, glaring at my freshly pounded ass. I wiggled my ass as to wave him over to me.
He climbed on top and slowly shoved his stiff cock in me again. I grabbed on the sheets and let out another whimper.
"you like being daddy's little girl, don't you?" he asked.
"yes daddy, I love it" I managed to say.
He started to pound me some more and all I could do was grab onto those sheets and gasp for air.
It was painful at first but I lost myself in his cock. I was a complete sissy. and I enjoyed every inch
of his hard cock pounding away at my tight hole.
"Im gonna cum!" he yelled "oh fuuuck"
And I could feel his hot man load filling up my tight sissy hole. Pump after pump. Giant load of cum was
deep inside me and finally my dreams had come true. I had daddy's cum in my sissy ass and I loved it.
"that was good. next time I'll cum in your mouth" he said, catching his breath.
"I'd like that very much" I said with an ass full of cum.

I slipped my panties on, along with the rest of my clothes and started to walk home.
on my way home I took out my phone, and ordered lingerie. I was going to dress up even more
and search for another cock to have fill me up. I was on my way to being a great sissy

(I Wrote this story from home, with a face full of cum. time to lick it off and get started on part 2) ;)

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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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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

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...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - 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...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sandys Sissy Maid

Sandy's Sissy Maid By maidboy275 Mistress Sandy had given me a simple order, "When you get up Monday morning get dressed into your pink domestic maid uniform." I knew I needed to do it, I even planed on doing it. Sunday night I had added a new coat of polish to my always polished toenails and then used the deep pink nail polish on my fingernails. I had let it dry in order to be ready first thing Monday morning. I had gone over my body with a razor in the shower and made sure I...

3 years ago
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Online Sissy Training

Online Sissy Training I must admit that I was surprised, but also thrilled to get the email. "Hello Sissy Michelle;" it read. "Please excuse my impertinence in reaching out to you, but I have seen several of your posts on Craigslist, Fetlife and Adult Friend Finder. You always say that you are a sissy seeking dominant men who will train you to become a sissy cum slut. I am guessing that you have not found that man as of yet, because I keep seeing variations on the same ad week...

2 years ago
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A sissy called Jezebel

Part I - Jezebel starts her big day, serving as a sissy maid for the dominant females of hir family. We seen in depth hir morning routine, as sie gets her sisters and hirself ready for school. My alarm goes off at 5:30 in the morning. It is an old fashioned wind up alarm clock with the clapper bell ringer which would wake up the dead, or at least this sissy who had been dreaming sweet dreams of dancing in a full ball gown with hir Prince Charming. I turn on the light on my side...

2 years ago
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Curiosity Spanked the Sissy Finale

You watch Mistress Michele sway towards you provocatively her red lacy worn panties dangling from her finger. Your cock throbs painfully knowing exactly where they are going. Reaching you she takes hold of the dildo and you plead with your eyes for her to remove it. Instead she turns it until the rubber balls are resting against your chin, a wicked smile on her lips. "I never knew what a cock sucker you were..." she smirks and you blush. "I mean ten inches!.You're a pro!..perhaps I...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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I Now Own You Sissy

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his submissive tendencies by pushing back against her finger, she'd given him a good hard anal fingering and then he'd revealed the true depths of submissive tendencies, to Dr Megan Sutton, or Miss Megan as he'd begin to know her. "Then a week before the next visit you'll not be allowed to cum, if you do, you'll be punished very firmly. I'll be measuring you cum output and will know if you...

2 years ago
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My Sissy Secret

My Sissy Secret I got the text on Friday afternoon, just as I was heading home for the weekend. I glanced at my phone as I left the building and stopped dead in my tracks. I didn't recognize the number, but the text sure got my attention. "Hello Sean," it read, "or should I say "Sissy Sean." I was standing in the parking lot trying to decide whether to block this guy or just ignore the text when his next message arrived. "I don't know if you remember me," he wrote, "but I...

4 years ago
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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...

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