Jen's Lesson free porn video

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Jen slowly dropped to her knees next to the heavy wood door that lead outside of the home. She knew what was coming, and she knew it would be painful. Her pussy started getting wet as she thought about it. Her Master would be home soon, and he was going to punish her. She had made the mistake of disobeying one of his orders three times in a row. She had flirted shamelessly with the neighbor unknowingly that her Master was watching her. She shivered in anticipation as she wondered what her punishment would be. She knew it would not be too harsh, although secretly she craved the punishment, the harsher the better. She heard her Master's car pulling into the drive-way. She lowered her eyes to the floor, and waited.

Grayson drove as fast as the law allowed down the road. He couldn't wait to get home to his pet; to punish her. They both loved it, and he knew it. She had flirted with the neighbor and, Grayson thought, she knew what she was doing. Jen knew there were strict rules against flirting with anyone other than the people her Master had previously approved. He smirked as he thought of her now, probably kneeling next to the door, waiting for him. He knew she would be wet, as he was already semi-erect. He pulled into the driveway and slowly got out of the car.

He opened the door and looked down at his pet. She was beautiful; her long black hair was shiny and straight. She had bright blue eyes, which Grayson felt could see right to his soul. Her body was long and lean, with perfect breasts that he loved to touch. Her nipples stood out proud from her body when she was turned on and he couldn't wait to pinch them.

Jen kept her eyes on the floor as her Master entered. She let her eyes scan his shoes, not daring to raise her eyes to his face. She knew the punishment for looking at him without permission. Her pussy grew wetter as she thought of intentionally looking at him to increase her punishment. She didn't need to look at him to know how handsome he was. His face was strong, with hard edges to it that made her go weak in the knees when he smiled. His blonde hair was soft and curly, while he brown eyes were soft and held a kindness to them that she had never seen before. His body was long and heavy with muscle. His dick was 9 inches long, and Jen could almost feel it filling her cunt as she thought about it.

"Stand."

His simple command made Jen jump. She quickly stood up placing her hands behind her back. Grayson did a slow circle around her noting in his mind that she was still fully dressed. Jen took a slow, steading breath.

"Take off your shirt and bra. Fold them neatly." He stood behind her watching her tanned back sway as she obeyed him.

He continued. "You should know, pet, that during your punishment I will refer to you as cunt, or slut. You will refer to yourself as slut or cunt. Do you understand?"

"Yes Sir." Jen said quietly.

Grayson nodded his head as if in agreement and leaned back against the desk behind him.

"Now do you know what you're being punished for slut?"

"Yes Sir. This slut is being punished for flirting with the neighbor." Jen answered standing with her bare back to her Master. Her skin was rippling with the heat his gaze on her skin was causing.

"That's right. You were quite a slut weren't you cunt?"

Jen squirmed.

"Yes Sir." She answered simply.

"Good answer."

Grayson stood and pulled a pair of nipple clamps from his pocket. He walked around to the front of Jen and showed them to her. A shiver shot down her spine, as her nipples started to tingle. She loved nipple clamps, her nipples were incredibly sensitive and Grayson knew that. His warm hand engulfed her left breast, slowly caressing it. He pinched the hard nipple between his thumb and forefinger, tugging on it heavily.

Jen moaned.

He placed the first clamp on her nipple, the soft metal biting into her skin. He took the other clamp that was attached to the other by a small gold chain and clamped in onto her right nipple. She groaned softly. He tugged on the chain that connected the clamps, pulling her nipples down with it. Jen moaned, her pussy juices flowing freely now.

"Take off your pants."

He knew she wouldn't be wearing underwear, at least she wasn't supposed to be. Grayson was surprised when she tugged her pants down and was indeed wearing panties. His pet had some things to learn, he decided.

"Take off the panties too slut. You know better than to wear underwear in this house."

"But Sir..." Jen began before stopping herself.

He quickly slapped her ass. It was a hard slap that made Jen snap to attention.

“You do not talk out of turn cunt, nor do you wear underwear in my home! Put them in your mouth.”

Jen obeyed. She felt ashamed that she had broken yet another rule. She put the small panties into her mouth, she could taste herself on them and she only grew wetter.

"Bend over the chair."

He produced a low back chair which Jen could lean over the back of and hold on to the seat. Jen knew what was coming now and her pussy clenched. She was going to get spanked and she couldn't wait. She bent over the chair and grasped the sides.

"Spread your legs cunt."

"Yes Sir."

She opened her legs and arched her back seductively giving him a view of her glistening pussy.

"Spread them wider. Show me how much of a slut you are."

She spread her legs wider giving her Master a perfect view of her asshole and cunt hole. Grayson’s cock twitched. God he was going to enjoy this so much. He turned to the large oak desk behind him and opened the long glass door. He pulled out a thick wooden paddle. He turned his attention back to his pet. He walked up behind her and slowly slid his hand down her soft ass cheek. He squeezed it before letting his hand slid lower. He skirted his hand over pussy lips, flicking her enlarged clit with his finger. Jen jumped and moaned around the panties in her mouth.

He snapped the paddle against his hand letting her hear it. She knew this was going to hurt. Without warning Grayson brought the hard paddle down on her right ass cheek. Her body was pushed forward as she tried not to yell.

He pulled the panties out of her mouth and placed them on the chair in front of her face.

“With each swat I want you to count them and say “Thank you Sir, may this cunt have another?” “

When Jen didn’t answer him he slapped her hot, dripping pussy with his open palm, quite hard. She jerked and cried out.

“Yes Sir. Sorry Sir!”

He didn’t say a word and brought the paddle down hard on her right ass cheek again. Jen cried out.

“Ohhhhh! Two. Thank you Sir. May this cunt have another?” She cried softly.

He switched to the other side of her ass and brought the paddle down harder.

“Three. Thank you Sir…”

He brought the paddle down again before she had time to ask for another.

“Four. Thank you Sir. May this cunt…OWWWW!!”

He brought the paddle down again on the same spot, before His pet had time to ask for another.

“Fuck. Five. Thank you Sir. May I…I mean this cunt have another?”

He slapped her ass with his hand hard. She was turning a nice shade of red.

“No you worthless cunt you may not have another!”

She was crying harder now, but her body had other ideas. Her cunt was dripping wet; she could feel the juices running down her leg. He went back to the desk and opened the cabinet. He placed the paddle inside and grabbed his favorite cane. He hadn’t had to use it on his pet yet. He had watched her look at it as she cleaned the home; he knew she was curious about how it would feel against her naked flesh. It was thick and Grayson couldn’t wait to use it. He let it slice through the air, and Jen squirmed when she heard it. She knew exactly what it was.

“Cunt, you’re going to get ten swats with this cane. The same rules apply. Count and ask me if you may have another. Understand?”

Jen swallowed hard.

“Yes Master.”

Grayson slapped her ass twice pulling a yelp from his pet’s throat. He positioned himself on her left and tapped the cane against her ass. She shivered, knowing this was going to be the most painful punishment she had received. She felt the cane leave her skin and suddenly felt a searing pain shoot through her ass cheeks.

“Uhhhhhhh. Thank you Sir. May this cunt have another?”

He brought the cane down on her skin lower than the first strike. It bounced against her skin making her flesh ripple.

“FUCK! Two. Thank…you Sir. May this cunt have another?”

She was beginning to cry again, the pain was unbelievable.

He brought the cane down again in the same spot the first swat landed.

“God damn! Three. Thank you Sir. May this cunt have another?”

Grayson slapped her pussy hard with his open hand. The pain shot through her body making her clit grow in length.

“Watch your mouth bitch!”

Jen fought the incredible urge to rub her ass with her hands.

“This slut is sorry Sir.”

He brought the cane down harder on her ass lower this time almost at the spot where her legs connected to her ass.

“OWWWWWWWWWW!!! Four. Thank you Sir…” Was all Jen could say before her Master brought the cane down another time on her ass in the same spot the last one landed.

“Five. Please Sir! I’ve learned my lesson!”

He slapped her ass with the cane again harder in the exact same spot for the third time.

“You’ve just earned a pussy spanking for that cunt. I’m the only one who knows when you’ve learned your lesson.”

Jen moaned.

“Sorry Sir!”

He brought the cane down again on her ass.

She was crying unabashed now.

“Seven. Thank you Sir may this cunt have another?”

The urge to caress her ass was unbearable. She clutched the side of the chair and held on her dear life.

Grayson brought the cane between her legs and slapped her open pussy with it.

“Fuck!!!!” The tears started coming down her cheeks in crowds.

“Eight. Thank you Sir. May this cunt have another?”

“That one didn’t count cunt. Your pussy was just begging for it.”

He snapped the cane against her ass and watched as the welts were rising nicely on her smooth skin.

“OWWWWWWWWWWWWWWW!!!!! Eight. Thank you Sir. May this cunt have another?”

“What will you not do anymore slut?”

“I….this cunt..” Hiccup. “Will not flirt with the neighbor anymore.”

“The next two will be the hardest yet.”

He stood back and used his large arm to bring the cane forward to slap her ass with it. He watched her skin ripple from the crash and moaned softly, as he grabbed his crotch.

“OUUUUCHHHHHHHHHHHH!!!!!!!!!!! Nine. Thank you Sir. May this cunt have….have another?”

“Don’t mind if I do!”

True to his promise the last one was harder than all the rest. He found a piece of skin that was untouched and Jen cried loudly as the searing pain ripped through her body.

“FUCK!! Thank you Sir. May this cunt have another?”

He slapped her ass with his large warm palm. The pain was intense.

“No bitch. You aren’t worthy of anymore.”

Jen didn’t dare move. She heard his zipper being pulled down and heard his pants hit the floor. He was going to fuck her. God she was so turned on. Grayson stepped toward her and roughly shoved a finger into her dripping cunt. Jen moaned loudly.

“Spread those whore legs of yours. I’m going to fuck you so I can spank that pussy without the distraction of this raging hard on.”

“Yes Sir.” Came Jens reply.

She spread her legs and moaned as her Masters beautiful cock sank into her sopping pussy. He slammed into her, extremely turned on by having spanked her. He grabbed her full ass cheeks in his hands and squeezed them. He reached down and suddenly unclasped the nipple clamps that Jen had all but forgotten. The pain was intense as the feeling quickly came back in her sore nipples. Grayson could tell his orgasm wasn’t far off and He knew Jens was already on the edge.

“Don’t you dare cum until I give you permission. Your punishment isn’t over yet.”

He pumped into her faster, reaching around her body to flick her clit. Jen moaned. Grayson’s balls tightened he knew he was about to cum.

“Please Sir. May this slut cum?”

Grayson groaned loudly grasping her fire hot ass cheeks in his hands and pulling them apart. He sank he thumb into her ass hole and pumped harder.

“Cum slut.”

Jen heard the words and started to come before he could finish the short sentence. Her orgasm made his own crash over the edge. She squeezed her pussy muscles around his cock as he pumped her full of his sperm. They both came hard, as Grayson slowed his movements keeping his softening cock in her tight pussy. He kissed the back of her neck and pulled out of her. Her pussy contracted around the empty space.

“Oh thank you Master. I love you.”

Grayson smiled.

“I love you too pet. But your punishment isn’t over yet. Stand and go lay on the kitchen table. Your pussy spanking is next.”

Jen shivered. She stood, wiped her face of her tears and walked quickly to the table.

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Girlfriends Lesson

Introduction: She always teased me…she needed a lesson! My poor Girlfriend&hellip,. Fran we will call her was always a little bit of a tease. She would dress really provocatively and loved the attention for doing this. The cat calls, whistles, spanks on the ass. It kind of ticked me off a little, but I was also happy I had such a hot girlfriend. I repeatedly told her not to dress the way she did in the summer. Little jean shorts with the pockets sticking out the bottoms and a tight tee shirt...

4 years ago
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Brats Incestuous Lesson Chapter 1 Nubile Girls Incestuous Lesson

Chapter One: Nubile Girl's Incestuous Lesson By mypenname3000 Copyright 2020 Kat The moans of my mother bled through my bedroom wall. I groaned as I lay in bed, hearing their passion. The bed creaked at the sounds my mother made. The passion. Twenty years of marriage and my parents were still going at it. A shiver ran through my virgin body. I shuddered at hearing the sounds. They were so loud. “Yes!” I heard my mother gasp audibly. I shifted on my bed. I suddenly felt my pajamas over...

2 years ago
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Late for the Lesson

She was late. Again. Alex looked down at his standardized testing books sprawled across his desk and sighed. Zoe was smart, and he enjoyed teaching her, but punctuality was not a strong point. He could never really stay upset when she arrived, though, flashing that smile that made him melt. He also couldn’t get enough of her cute, innocent face framed by long strawberry blond hair, and a toned, tight body that he tried to keep himself from staring at during their lessons. She probably noticed...

Straight Sex
4 years ago
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Teaching my daughter a valuable lesson

While driving home, I saw that the weather outside was nice, so I planned to take a jog through my neighborhood when I got home. Plus, I had a new sexy jogging outfit that I was sure was going to turn a lot of heads. I made it home at exactly 1:00 PM. Exactly two and a half hours before my daughter Erica would be arriving home from school. As I stood in front of my full-length mirror, checking out the way my new pink and white outfit hugged my slim/thick 6', 190 lbs, 38-D's, and 48-inch...

4 years ago
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Girlfriends Lesson

Fran we will call her was always a little bit of a tease. She would dress really provocatively and loved the attention for doing this. The cat calls, whistles, spanks on the ass. It kind of ticked me off a little, but I was also happy I had such a hot girlfriend. I repeatedly told her not to dress the way she did in the summer. Little jean shorts with the pockets sticking out the bottoms and a tight tee shirt that showed her well formed mid drift. I said if it turned me on the way...

3 years ago
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A woman gets a special reading lesson

It’d been a good week. Tips were good, the bar had a new DJ and a football camp was in town. The boys liked to watch her dance after a ‘hard’ practice. On the couch, they held her against their washboard bellies stuffed money down her g-string and told her she was nothing like the girls back home. The only down side was her damn Thursday class. She just wasn’t getting the writing. It bored her. But then HE called. The first time they met, here at the club, he...

3 years ago
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Teacher gives pupil an extracurricular lesson

Bill, aka Mr Brown the Maths teacher, meets Suzy at her mum’s house for some naughty role play but gets the surprise of his life. Suzy then makes Bill an offer he can’t refuse. I’ve not posted for a while. You might want to first read Chapter 1 - ‘Let the Sunshine In’ posted 3 months ago.The next day Suzy came into my office to tell me that her mum was jetting off on holiday for 2 weeks on the coming Monday. ‘Are you still up for meeting at my mum’s place Bill’?‘Definitely I’ve thought about...

3 years ago
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A Good Hard Lesson

THIS IS A WORK OF FICTION.Mr Collins hated Mondays. It's well known that most people hate Mondays but Antony Collins loathed them; it meant the start of another week teaching rebellious, ignorant, hormonal teenage girls. Everyone had told him that teaching at a Catholic school would be a dream, but clearly they'd never taught at St Anita's. He was sure they were worst than any public school girls. On this particular Monday it was raining, not uncommon for December but it meant all the girls...

Straight Sex
2 years ago
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Millis Second Lesson

Milli's Second Lesson Janice entered the kitchen next morning and sat across from Elaine, drinking coffee. "Where is our sweet Milli? Shouldn't she be here making breakfast?" "I don't think she quite knows her place here yet." "Well go get her, there's no time like now to start showing her." Elaine went up to Milli's room. Milli was naked about to take a shower. "No need for a shower right now sweetie. We need you down stairs at breakfast, get...

4 years ago
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Mom teaches me a lesson

It all started when my friend came over my house. We were surfing the web for mature porn and reading stories with mature ladies. See Nate got me into the idea of fucking mature ladies, how they have experience, and have bigger boobs and big asses than the girls our age. We are both 18 years old, I am of Indian descent. Nate is black and looks a bit older than me, he a bit taller and built for his age. We met at the basketball courts about 4 months ago. He comes over my house not so often cause...

Incest
2 years ago
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I love to learn sex lesson

Hi to all ISS readers, this is Ahmed Kabeer (not real name) from Hyderabad. Before going for story I would like to my self my name is Ahmed age 24 years 65 kgs weight color fair height 5’5” tool size 6”+, I completed my Mech engg in 2004 from 2004 I am working as a design engineer (mech), so friend this is my short and sweet introduction.When I was a student of 9th standard I was unknown of sex, a girl name Saba (name change) started my new version of life the information of sex, before...

4 years ago
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Brats Incestuous Lesson Chapter 3 Brats Final Taboo Lesson

Chapter Three: Brat's Final Taboo Lesson By mypenname3000 Copyright 2020 Kat Fear rushed through me at my mother's fury. I ripped my pussy off Daddy's cock and threw myself from straddling him on his recliner. Mother stood at the entrance of the living room, wearing her gardening clothes. She was supposed to be out in the backyard. She wasn't supposed to come into the house and catch me with Daddy. I fled. I raced out of the living room, tears spilling down my cheeks. I felt the cum...

1 year ago
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Mom Teaches Me A Lesson

Note : This story is completely fictional! It all started when my friend Nate came over my house. We were surfing the web for mature porn and reading stories with mature ladies. See Nate got me into the idea of fucking mature ladies, how they have experience, and have bigger boobs and big asses than the girls our age. We are both 18 years old, I am of indian descent. Nate is black and looks a bit older than me, he a bit taller and built for his age. We met at the basketball courts about 4...

Incest
1 year ago
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The Guitar Lesson

I hated working in these “gated” communities, but lately times had been harder with lesson requests coming less frequently. My band was working a regular gig at a club in Fort Lauderdale, but the revenue from this wasn’t much of a living by the time we divided the money three ways. I knew that if things didn’t start improving soon financially, I would have to get a regular day job. This thought made me cringe, so I left no request for lessons unanswered, as frustrating as they could be. I had...

Erotic
4 years ago
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The Futa Fairy Futa Fairies Naughty Game Chapter 2 Ms Marcies Kimmies Naughty Lesson

Chapter Two: Ms. Marcie's & Kimmie's Naughty Lesson By mypenname3000 Copyright 2017 Mrs. Fatima Samara I clutched my harem to me as the clock struck midnight. The year ended. A new one begin. My daughters, niece, and sister were naked, smeared in my cum. I tried to love all my pregnant women before I had to repay my debt to the futa-fairy. To Leanan Sidhe. Despite the spurting futa-jizz and the gasping orgasms, dread had permeated me all day. Now a warmth billowed through me,...

2 years ago
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A Sexy Subject Part 2 A Lesson

I walked upstairs to my bathroom and stripped off my clothes. As I ran hot water into the tub, I started thinking what I had let Mr. Burkle do to me. I remember him pushing his thick fingers in and out of my pussy and I unconsciously let my hand wander down between my legs. I found my clit and rubbed it back and forth. It started to swell and the feeling inside my pussy became more intense. I rubbed harder and I felt my knees almost buckle from the explosive orgasm I had. I braced one hand...

2 years ago
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Millis First Lesson

Milli's First Lesson Janice pulled the Lexus into the driveway, and noticed her bedroom light on. She was positive she turned it off before she left this morning. If her wayward Nephew was nosing around in her room there would be hell to pay. She was already extremely ticked off at having to attend a meeting with his Principal this morning. A meeting which ran on too long, causing her to miss her flight to Chicago. Thank goodness she was able to assure the Principal that Bill...

4 years ago
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The Rogues Harem Book 2 Chapter 15 Princesss Naughty Lesson

Book Two: Rogue's Wicked Harem Part Fifteen: Princess's Naughty Lesson By mypenname3000 Copyright 2018 Note: Thanks to WRC 264 for beta reading this. Chapter Forty-Three: Princess's Naughty Lesson Princess Ava – Az, Princedom of Kivoneth, The Strifelands of Zeutch I stared with loathing at the shelves of leather-bound tomes and tightly wrapped scrolls stacked before me. The receptacle of lore contained within the University of Az's library. The air smelled of musty sheepskin and dry...

3 years ago
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Mr Dentons Next Lesson

I got the note on the top of my paper. It said simply, “Delilah, see me after school. It is time for a new lesson.” I didn’t know what to make of it. I hadn’t done anything wrong this time. I hadn’t been whoring around, or fucking other boys. I had no idea why Mr. Denton would want to teach me a new lesson. My nipples hardened in anticipation, and I smiled at him. His face gave nothing away. I tried to flirt with him and he studiously ignored me through the entire class period. After the last...

2 years ago
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Savage Lesson

SAVAGE LESSON It is one of the unalterable facts of life that women are mysterious. There is no point in trying to rationalise, trying to account for or predict every facet of their behaviour because whatever you think you know is liable to flip over on you revealing a truth you never guessed at. Let me put it another way: You know in those naff horror films where someone looks at their reflection in a mirror? Then they put their hand out to touch the mirror and it turns out to be a pool of...

3 years ago
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Teacher teaches me a lesson

My name is Jonathan and I am seventeen years old, it was my last day of school for this year and our last lesson was Geography. I am normally a very well behaved pupil, a bit boisterous at times and a bit of a rebel when I have my friends around me, but then I do have friends that would encourage and lead me on. But underneath the brave façade lies quite a shy boy for my age. My friends and I have all bragged about the things we have done to try and outsmart each other, as all boys do at that...

4 years ago
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Teacher teaches me a lesson

My name is Jonathan and I am seventeen years old, it was my last day of school for this year and our last lesson was Geography. I am normally a very well behaved pupil; a bit boisterous at times and a bit of a rebel when I have my friends around me, but then I do have friends that would encourage and lead me on. But underneath the brave façade lies quite a shy boy for my age. My friends and I have all bragged about the things we have done to try and outsmart each other; as all boys do at that...

Seduction
2 years ago
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Another Good Hard Lesson

For the prequel to this story go to:  You can do this… You can do this…You can do this… Teacher, Antony Collins had been thinking this all day, over and over again as he prepared for his English class later that afternoon with the sixth formers. With Alex. Unbidden, the memories of what they’d done a couple of days before came flooding back to him yet again, her soft, pert breasts under his hands, her wicked mouth around his cock, her tight pussy gushing cum all over him…. The sharp ring of...

Straight Sex
3 years ago
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The Lesson

The Lesson By GSElvis Jeff was happy with his life--almost. He was a mechanic at a new car dealership, and was good at what he did. His job gave him a comfortable life. He lived in a good apartment in a large apartment complex. His assigned parking spaces contained a shiny, new pickup truck and a big, powerful motorcycle that he enjoyed driving on weekends. The people he worked with liked him. But he was unmarried, childless and alone, and that ate away at him. He had no...

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