Sissy Punishment - Chapter 2 free porn video

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Sissy Punishment Chapter 2 By Sarah James squirmed as he walked back to the classroom after his trip over Principal Julie's lap. Ms. Owens and Principal Julie had dressed James up in one of the girl's school uniforms after they had found him rummaging in the lost and found, and now he was going to face his classmates for the first time as Janet, the name Ms. Owens had given him. Janet's bottom still was sore, and he knew he was going to squirm for the rest of the day. But thankfully it was only one more class. Janet paused at the classroom door, and braced himself before pushing it open. The gasps and giggles and snickering started almost as soon as his classmates saw him. Their teacher also had to hide her smirk behind her hand. Janet turned beat red as the entire class started laughing and pointing, and all he could do was to walk slowing to his seat, and hang his head. Ms. Owens and Principal Julie had discreetly followed Janet up to the classroom, and could hear the smirks and giggles from within as Janet made her entrance. Principal Julie allowed a moment, before entering the classroom. "Students, I would like you to welcome Janet to your class. Some of you may think you see your old friend James in Janet, but rest assured, Janet is here now and James is not. Anyone caught physically or emotionally harassing Janet will suffer a similar punishment, so don't even think of it. Girls, Janet is new to our school, so one of you might want to befriend her, and help her with makeup and other things during the weekend. Boys, if you so much as try to flip her skirt up, you will find yourselves in a skirt before the hour is up. Now, get back to studying, and enjoy the last class of the day." Principal Julie and Ms. Owens maintained a minimal distance from the classroom, listening as the teacher resumed her lesson, and the class settled down into taking notes. The two women, satisfied that Principal Julie's warning had carried the weight needed to ensure Janet's safe departure to his house when school ended, returned to Principal Julie's office. "Well Sarah, it seems that little Janet is in for a long month, or more. Your idea of putting him into the girls uniform was inventive, and ingenious, to say the least. But, you and I have some business to attend to this weekend too, don't we?" Sarah Ownes, the school guidance councilor and submissive of Principal Julie, bowed her head and nodded. "Yes Mom, we do. Shall I ride home with you, or take my car there?" "Oh, I think I will give you a ride today, little Sarah. When we get home, you go right up to your room, and put your little school uniform on. I saw the way you were squirming as Janet got her bottom spanked, and I think it is time you got yours spanked too." Sarah and Principal Julie continued to discuss their weekend of fun, while Janet squirmed in his class on his sore butt. He knew his parents would be upset when they picked him up, but little did he know just how much trouble he was going to be in when he returned home. Upon hearing of their son's discovery yet again in the lost and found, and what Principal Julie had decreed should happen, Janet's parents had removed from his room all his boy clothes and anything themed for a boy's room, and had replaced everything with girl themed room and clothes. Their only exception was the dresses that Janet would be wearing, which his mother had decided that they would purchase after school. As the final bell rang, Janet gathered his things, and went out to the pickup area. The rest of the students all were laughing and pointing, or trying not to draw the gazes of the watching teachers, or were rushing to get tot heir cars and busses. Janet saw his mother waiting at her car, and rushed over, blushing crimson and ready to sob. He couldn't even look her in the face as he crawled into the back seat of the car. Janet's mom smiled as her humiliated son scampered into the car, giving her a nice peek up his school uniform jumper at his white panties and around the cloth, the red tinge showing his spanked bottom. She knew that one spanking wouldn't be all he received today. As she started the car, she looked in the rearview mirror as her son squirmed and blushed in the back seat. "So James, or is it Janet now? I see you got yourself in trouble again, and this time, it looks like the school is going to make you wear the girls uniform to go to school. Well, your father and I also got told, and your father was in a blind rage when he heard. I managed to calm him down, but the next month at least is going to be hell for you, little missy. We are going to the mall now, to get you some proper clothes to wear for when you're not in school. Oh, and don't think your punishment is going to end, just because your not at school. Oh no. Your father has made it clear. If you want to be a girl so much, then you are going to be a girl for a month at least." Janet went white upon hearing of his home punishment. It would be bad enough going to school in the girls' jumper uniform, despite wanting to do it all his life. Now he was going to be treated like a girl all the time for the next month at least. Janet was close to breaking down, at how quickly his life had changed. But he knew if he quit, he would be expelled, and none of the schools around the city would take him, if they found out he liked to steal and wear girls' uniforms. Janet and his mom left the school parking lot and drove off to the local dress maker's shop. Janet's mother had phoned and made an appointment with the owner of the shop to make sure Janet would be fitted properly, and to make sure his special circumstances were known so there was no problem. The owner smiled as she listened to the boy's punishment, and readily agreed to make sure that Janet would be fitted properly for a sissy little girl. Principal Julie and Sarah drove to their shared house on the edge of town from the school. Both knew that the weekend promised to have a lot of interesting fun for them both, and they were eager to begin. Sarah arrived first, and made sure the house was clean before going to her room, and changing into her own schoolgirl uniform. She took the time to make sure everything was authentic, and sized to fit her, but make her look like she was a student in Principal Julie's school. She slipped on the same cotton panties, the same knee socks, the same blouse and jumper, and even put her hair up into a ponytail with the school approved hair bow. Julie arrived home half an hour later, and smiled to see Sarah already in her uniform, doing her homework. Julie knew Sarah liked to act like a schoolgirl when she was doing the reports the county asked, and so Julie allowed her to do her work. But Julie also took time to punish the naughty schoolgirl when she found Sarah out of uniform. Julie also had been working on something truly special for Sarah, and was finally ready to reveal it to her excited slave, as the weekend progressed. Sarah had heard Julie arrive, of course, and made sure she was hard at work, but the feeling in her belly was always there when she knew she was going to be getting her own bottom spanked. Many times the girls who were spanked would come into her office after their spanking, and Sarah would hug them and comfort them till they were ready to return to class. And all those times, Sarah knew she would love to be in their shoes, getting her bottom spanked by Julie. Janet and his mother arrived at the dress makers shop, and Janet felt his stomach drop as his mother led him inside. He could smell the perfume and hear rustle of fabric as his mother led the way up the aisles around the brightly colored and frilly dresses. Janet had, of course, walked by the shop numerous times and dreamed of entering, but he never had plucked up the courage. Now he was in here with his mother, and he knew she was going to be forcing him into any number of the dresses, and there was nothing he could do to stop it. The dressmaker smiled as she watched the young boy walk up the aisle in his schoolgirl uniform. She had seen other boys being forced into dresses by the local city juvenile judge, mostly because the boys stole panties or lifted the backs of girls' dresses. But this was only one of a handful of times that the boy arrived in a uniform, and didn't seem totally out of control. Janet's mom smiled and hugged the dressmaker, and then pointed to Janet. "This is Janet, and he needs some nice new dresses. According to the school, the jumpers he keeps taking would put him in the 3rd grade, so his father and I have decided to dress him like a pretty 6 yr old. We want him in petticoats, nice bowed and fluffy dresses, and of course, all the trimmings to go with his age." The dressmaker smiled, and turned to Janet, and took out a tape measure. She was surprised that the uniform had fit him so well, but she knew Sarah was a good judge of figures, and probably had pre-measured the boy for his uniform. She made a mental note to check with Julie and Sarah, and see how they were doing. Turning her mind back to Janet, she began measuring the nervous boy. Janet was dumbstruck by some of the measurements the dressmaker took, but unconcerned about the regular ones he expected. It seemed that she knew what she was doing, and in no time, Janet was being led to the section where the little girl dressers were arranged and displayed. "Rachel, as I told you on the phone, we need to custom make the dresses for Janet, but I think we have a few of the larger ones in stock, which should fit him nicely. We keep a nice selection here, because Judge Lumus likes to send the boys here and force them to serve time in the outfits the girls they humiliated were in. Let me take Janet's sizes to the back, while you and he pick out some other outfits that Janet likes." Janet, the dressmaker, and his mom spent the better part of 3 hours pulling out dresses, forcing Janet into the ones that would fit, and making the marks necessary to alter the ones Janet couldn't fit into. Janet knew his wardrobe would full by the time everything was collected and hung up. Janet also sported new panties, some to match dresses, others to humiliate him if his dress should fly or be taken up. Socks, hair bows, and the rest all were purchased to make sure Janet knew that there wasn't any escape after school. By the time they left the shop, Janet had enough dresses to last the week, and 3 more school uniforms for next week. Sarah and Julie also were nearing the end of their normal post day duties. Sarah had finished drafting a report to the city school district on Janet's petticoating and planned time being treated as a girl. She made notes on the punishments recommended, what his parents were expected to add on, and what the final prognosis was likely to be. She also had written up her staff evaluation reports on the plan, reactions from students around Janet, and the plan the school had, in case the prognosis was proven true or false. Sarah leaned back in her chair, and stretched. Julie came around her slave's back, and began rubbing her shoulders, Sarah always loved the care Julie gave her, and smiled and purred at her housemate's attention. She knew eventually Julie would pull her over her lap, and raise her skirt, and warm her bottom, but right now, it was more than enjoyable to get her neck rubbed. Julie also enjoyed putting Sarah into a relaxed mood, before they played their games. It made the anticipation build, and when it finally began, it made it all the sweeter to hear the whimpers and moans that inevitably came from Sarah. Soon, Julie thought to herself, it would be time to begin with her slave housemate. For now, the weekend was just starting.

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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

2 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - 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...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

1 year ago
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Sissy Crissi Chapter 2 Facing Erika

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...

4 years ago
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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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  • 37
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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...

1 year 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, ...

1 year 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
1 year 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....

3 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....

3 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...

2 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...

2 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...

1 year 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...

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