Sissy In Prison free porn video

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The guard came to get me at 6pm. The sun was low in the sky and it would be
getting dark soon. He led me down to the showers, and turned them on.

"Razors and soap are in the corner" he said.

I knew what he meant. I set about shaving off all the hair on my body. I
closed my eyes as the razor traced up and down my legs. I parted my cheeks
and ran the razor on the inside of my buttocks until they were clean.

Finished, I grabbed the soap which was scented with a delicious citrus
smell. I lathered it all over my body, rubbing in the smooth suds.

The guard cut the showers and through me a towel. It wasn't the average
prison towel, it was egyption cotton and very soft. I took great pleasure
in drying myself off.

I went into the next room. There were my clothes that the guards kept for
me. A black basque with rose-shaped stitching, which I squeezed into.
Having closed all the clapsed, I looked at the guard as I twisted the basque
around to the correct orientation.

I picked up the black lace-topped stockings, fed my smooth legs into them
and clipped them into the holdups on my basque. I plumped up my basque with
fake breasts. Finally I slipped on my black lacy knickers, over my garters.

Settling down in front of a large, dressing-room stle mirror, I set about
putting on my make-up. Dark whorish lipstick, foundation and blush. I
plumped up my eyelashes to give me a sultry look. The final touch was the
blonde wig I clasped to my hair.

Slipping my feet into high-heels and donning a sheer, see-through dark gown,
I looked at the guard and told him I was ready. He nodded.

=================

I walked down the gantry ahead of the guard. It was dark, after lights out,
so walking in my heels was especially difficult. I got to my destination
and the guard told me to stop.

"Lights on cell A24!" shouted the guard, and the lights inside the cell
burst on. Inside, the inmate - known as the b**st - growled as the bright
light hurt his eyes. He cursed until his eyes adjusted and he spotted me. I
expected a smile, but his face remained cold and emotionless.

The other inmates were attracted to the light, and when they saw me they
started cat-calling, howling and hurling abuse. I turned toward the b**st,
putting my ass to the baying mob and gave it a sexy wiggle. The mob went
wild.

The cell door opened and the guard prodded me in the back. The b**st rolled
onto his feet.

I strolled forward, dropping each hip as I walked in the style of a catwalk
model. I dropped to my knees and looked up at my lover. He looked down at
me and grunted. I reached up with my manicured hands and undid his zipper.
Reaching in to his prison overalls, I grabbed his stiffening cock and
pointed it at my face.

Looking up at my lover and staring into his eyes, I took his large cock into
my mouth and sucked. I sucked as hard as I could, all the time looking up
at this dominating tower of muscle. He hadn't shown any sign of pleasure
yet, and I was scared.

I began rolling my tongue over his cock and he sighed. If I hadn't had his
stiff member between my red lips, I would have breathed a sigh of relief
myself. Now relaxing a bit more, I set about working on his cock. I shot
my head back and forth, collapsing my hand as my mouth went forward and then
stiffening it back up as drew back. The b**st groaned, then shot his hips
forward, jamming his dick in the back of my throat. I gagged. The crowd
loved it.

"You like that, don't you bitch?" he boomed above me. "A full length of the
b**st's cock!".

I was so aroused by this whole thing. I was being dominated by a strong
man, dressed in the sexiest of clothes and had a crowd watching. My little
cock was rigid.

The b**st grabbed the back of my head in one hand, and his 9" cock in the
other, and began slapping me in the face so hard I thought it would bruise.
The mob jeered as I tried to chase his weapon with my open mouth, my tongue
rolled out.

After I was totally humiliated, the b**st growled "Up, bend over".

I stood and slipped off my sheer gown. I heard the other inmates gasp as
they saw me - the sexiest woman some of them have seen in years, and that
most of them will see in years. I turned away from the b**st, sideways to
the front bars of the cell, walked over to the desk in the cell and bent
over it.

The b**st walked up behind me. His strong, calloused hands slipped down my
delicate panties. He ran his hands down the black seams of my stockings and
grunted with excitement.

Taking my hip in one hand, and his cock in the other, he began to feed
himself into me. I'd lubed up and stretched my ass out in preparation, but
his cock-girth made me squeel in pain. The mob roared when they heard my
girlish yelp, and this turned the b**st on. He began vigorously pumping my
ass, battering his way in until it was up to the hilt. It hurt my sphincter
so bad, but with each thrust the pain eased and the pleasure increased.
After 3 or more minutes of torture, I began to groan like a porn star.

"Fuck me, fuck me. Oh yes, come on big daddy. Fuck me. Ahhhhh - don't
stop. It's so big".

The inmate in the next cell was trying to reach out and touch me through the
bars, but he couldn't reach. I stared into his eyes for a moment, then
closed them as the b**st's member plundered my delicate hole. The whole
prison was erupting with noise, a deafening din.

The b**st grabbed both of my hips and lifted them. He was so strong that he
lifted my heels off the floor. I held on to the table with all my strength
as he used this new angle to penetrate me to his full depth.

Mercifully, the b**st began to yell as his cock slammed into my ass. His
warm seed pumped deep inside me. He held me in place for a second, then
snorted derisively. Instead of withdrawing from my, he threw me forward,
off his cock. I flew over the desk and banged into the bars at the side of
the cell. The b**st turned and walked back to his bed.

The prison was now quiet. The audience had been sated. As I was led by the
guard back to my cell, imagine all of those prisoners cumming over my
performance. Cocks in hand, shooting their load. Some inmates had bitches
in their cells, and I imagined them forcing their prey to suck their cock
while they watched and imagined it was me. All the way back, the b**st's
sperm worked it's way out between my femimine buttocks.

This was the way it would work from now on - if the rougher prisoners
behaved, they'd get a visit from me at the end of the month. I'll need more
outfits.

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Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

2 years ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - 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 Jamie, ...

2 years ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
2 years ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

4 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

4 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

3 years ago
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Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

3 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine 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...

2 years ago
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Sissy Gets A Black Master

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

2 years ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

3 years ago
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Sissy Stepson Part 6 Carolines Sissification

Part 6 - Caroline's Sissification Mrs. Monet was now going to really put the spurs to her sissy stepson and force him to live a life of sissified faggot. With Carl still lying on the floor with sissy cream stains all over his pantyhose and panties she began taking pictures of sissy stepson. "What are you doing, I want to change," said Carl. "Oh, no just because you popped your cookies doesn't mean its over, you pathetic faggot. I now have evidence what a pervert you are and I...

3 years ago
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Sissy Therapy

Sissy Therapy by Kate "Great practice, guys! If we keep working hard, we have a real shot at the conference title," Coach Jones addressed the thirty or so high school boys gathered around him. The boys were sweaty and tired, but the coach's praise momentarily raised their spirits. "Smith nice passing out there. Keep up the good work." Fifteen year old Billy Smith grinned cockily. "Sure, Coach. After all, I am the greatest!" The other boys moaned at Billy's arrogance. Coach...

4 years ago
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Sissy Stepson 8 Carolines Milking

Part 8 - Milking Caroline "Our sissy is going to get ready for milking, I have enough knee highs for everyone to participate" said Mrs. Monet excitedly. She gave everyone three knee high's, sissy Caroline was going to get the milking of her life! Caroline came back to the group with here outfit on and was instructed to sit next to Regina for milking. Regina encased the Caroline's sissy stick with the nylon and instead of using her hand. She took off her high heel and stuck the toe...

2 years ago
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Sissy hypno The beginnings

The beginnings of cock lust – Sissy Hypno pornFOR THOSE NOT INTO STORY OR BUILD UP, SCROLL DOWN TO THE ******** MARKER FOR EROTIC ACTION!Felicity heard Billy come rushing down the stairs from his home quarters above the pub, he swung around the doorframe and appeared behind the bar area calling out to the Indian beauty who was sat looking out the window for a moment.Felicity stood in an empty pub window looking out at the welsh countryside. As far as her Indian eyes could see, were blankets of...

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