Holly's Story - Day 01

INTRODUCTION

It was the first day Uncle Jack was taking care of his niece. He wasn't her parents first choice for the job but they were in a bind. Their biggest customer was redesigning a product line and they absolutely had be on site with him for the next two weeks. Unfortunately their regular babysitter had gotten in an accident and was in the hospital.

Her parents were timid and scared. They were sure something bad was waiting just around every figurative corner. That made them very conservative and very protective of their only child. They had strict rules about everything: foods, books, TV shows, movies, play dates, friends. But they were especially strict about how she dressed.

Clothes were the first step on a slippery slope to something bad. Clothes defined what kind of person you were. They didn't want their daughter to be the kind of person who tempted fate by being too flashy, too trendy, too sexy, too unique.

Unfortunately for them Jack was the exact opposite, a man who constantly tempted fate. The books he wrote were too trashy; his clothes were too tailored; his dates were too pretty, too tattooed and wore too little clothing; he traveled to places that were too foreign; his car was too fancy. Certainly terrible things would happen to Jack someday and they didn't want their daughter nearby when that happened.

If they had known of Jack's private activities they never would have called. Jack belonged to a social group that indulged in a wide variety of sexual desires. He was one of the most respected members of the group, largely because he was an omnivore. He participated in everything.

But they didn't know and they were out of options. They called. Jack agreed.

The parents hoped fate was busy watching someone else. They trusted their daughter was a prim and proper young lady, following all the rules. At school, she played field hockey, was on the debate team, and was an honor student. At home, she was modest and respectful. What could happen in just two weeks?

Appearances were deceiving. Although she was naive in many ways, particularly about sex, their daughter secretly rebelled against the rigid protections her parents decreed. She read forbidden books at the library; she watched forbidden movies at her BFF Emma's house; she ate forbidden food on field trips. If somebody was going to have their skirt a little too short or blouse a little too unbuttoned at school, it was their daughter.

When her parents weren't home, she walked around naked or wearing a skimpy bra and panty set she kept hidden in her closet. The older she got, and she was now 18, the more she craved a great exciting adventure.

And now Uncle Jack was coming for two whole weeks. Their daughter had adored Uncle Jack her entire life. He was her role model. Finally she might get her adventure.

Uncle Jack knew about the rebellions and the desire for adventure. "Someday" he thought "she's going to explode like a rocket with some lucky guy."

Her name was Holly.

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DAY 1 - WEDNESDAY

Holly's parents had left in the morning before she went to school. After school, she and Jack chatted a bit before she went to her room to do homework. Now dinner was almost ready.

Jack went down the hall and looked in Holly's door. His niece was attractive but not stunning. Her narrow face with it's strong nose and chin made her look older than 18 but the rest of her looked younger. She was a late bloomer.

Her cheeks retained a certain baby like roundness that would disappear in a few years. She was barely 5 feet tall, slim with wavy dirty blond hair. Her breasts were almost a B cup and her hips had only just begun to widen.

Holly was laying across the bed watching a movie. She was wearing a cut down tee shirt exposing her tummy and the bottom of her bra. Regular shorts had been reduced to short shorts that barely covered her panties. Jack smiled. It had taken her no time at all to create an outfit her parents would thoroughly disapprove of.

"Dinner's almost ready" he said "What are you watching?"

"Mean Girls. Emma loaned it to me. Want to watch the end with me?"

"Are you allowed to watch that? Isn't it too mature for a 18 year old" he teased. Holly rolled her eyes and moved up on the bed to give him room.

Jack flopped down behind Holly. The mattress bounced her back into him. Holly wiggled to get comfortable. Almost instinctively Jack adjusted his position so his cock nestled in the crack of her ass. It began to harden.

Holly gasped a little but held still. Jack thought a minute. He knew his niece felt stifled by her parents. He knew she had been flirty with him since he arrived two days earlier. He knew she had cut down her tee shirt and shorts as soon as they were alone together. He concluded she was looking for an adventure and hoping it was sexual. He also knew she was naive and almost anything would qualify.

Jack was an adventurer and risk taker. So he took a risk. He put his arm around her, casually draped over her bare stomach. She scooted down until his thumb rested on the bottom of her bra and froze. He waited a moment and began to rub her belly in a circle. At first it was just on the exposed flesh. She sighed. He widened the circle to push under her tee shirt and slide along the bottom of her bra cups. A gasp but she didn't move. He circled down to the top of her pants. After a couple more circles her breathing quickened.

He thought about what to do next. Did she really want him to touch her in a sexual way? Or did she just want the appearance of doing that? Faux sex.

Holly mind was also swirling with thoughts. Her upbringing said this 'adventure' had already gone too far and needed to end before disaster struck. Her true self said this adventure had just begun and others awaited. With her parents gone, she should seize the moment. Carpe diem! and all that stuff. Holly couldn't decide which path to follow.

Holly's true self cheated and made the decision for her. Without conscious thought, Holly clenched her ass, squeezing Jack's cock. He felt it and decided to press on.

With the next circle his hand reached the bottom of her bra and pushed it up on her breasts. Holly raised her arm a little. Jack moved under her bra and cupped her bare breast in his hand. She gasped and raised both hands over her head. The hem of the tee shirt lifted, giving him greater access. He pushed the bra higher fully exposing both breasts.

He fondled her breasts, first one then the other. Rolled a nipple between his fingers. It grew as it hardened. "Big nipples" he thought. Holly was squirming but not trying to get away. She was quietly moaning.

"In for a penny, in for a pound" he decided. Jack moved down and slid between her shorts and her panties. He went down until he could feel pubic hair under the panties. She froze. Her breath stopped.

Holly decided. She had wanted an adventure, her uncle was offering an adventure, and she was going to take advantage of the offer, consequences be damned. She thrust her pelvis forward just has his hand slid back toward her stomach. Holly grasped his hand and pushed down.

Jack followed her lead. He unsnapped her shorts and pulled down the zipper. Holly was lost. She couldn't think straight. Random thoughts swirled through her mind. Her body reacted by instinct - she began opening her legs. Jack slid his hand under the panties to the top of her slit. Holly moaned louder. "Yes! No! Oooh!" She was scissoring her legs. Her uncle took her clit between his fingers and began to massage it. She thrashed around, pressing his hand into her crotch. It only took a few moments until she shuddered a little, let out a moan/gasp, and slumped back. "Not bad for her first time" Jack thought.

It wasn't really an orgasm but Holly didn't know that. It was the sexiest and most adventurous thing she had ever done. She lay still on the bed enjoying the after glow and reliving how her uncle had touched her.

The movie ended. Jack stood up. Holly's bra was pushed up exposing her small breasts. She had light colored areolas and both nipples were still long and hard. Her pants were open. He could see her striped cotton panties and just a bit of blond pubic hair sticking out. One leg was raised revealing a small wet spot on her crotch. He smiled again. "Dinner will be ready in five minutes".

Ten minutes later Holly came out of her room. Jack was already seated at the table with a plate ready for her. Her now braless nipples poked at the white tee shirt. He hoped she was also pantyless. She was still a little shaky walking to the table. "Is your homework done?" Jack asked. The banal conversation calmed her down to the point where she became embarrassed about her braless condition. But she couldn't cover her breasts and eat without looking like an idiot.

She was startled out of her reverie by her uncle. "Was it as good as you thought?" he asked slyly.

Without thinking, she sighed "Better."

"I meant dinner" he grinned.

She blushed furiously but retorted "Dinner's not as good".

The meal done, Holly cleared her plate and turned toward her room. With her back to him she asked "Can we do that again sometime?".

Jack thought about his answer. With his preferences it was important that the partner freely and fully commit. Usually his partners were older and experienced. Holly was different. She was not only inexperienced, she was sheltered, naive. When her parents returned she might regret it and confess all. There was a long pause while he considered the situation.

Holly was frozen in place. Terrified. The question had seemed so easy to ask when she rehearsed it in her room. So much harder in front of her uncle. Now there was just silence. Was he going to freak out? Tell her parents? Call the police? The possibilities raced through her mind and most were not good.

She gathered her courage and turned to face him.

He didn't seem angry. He wasn't freaking out. It seemed like he was considering his answer. That was encouraging. How to convince him? Holly did the only thing she could think of. She reached down and pulled her tee shirt over her head. He looked at her small breasts and erect nipples. His cock twitched in his pants. "I hope that's a good sign" she thought and pulled her shorts down. No panties. She stepped away from the shorts and stood there completely naked.

Jack slowly looked her over from head to toe. She was short, barely five feet tall, athletic, with a slight build. There was still some baby fat clinging to her face and waist. Her wavy hair was shoulder length.

Though she was a senior in high school, she was still developing. The blond public hair was little more than peach fuzz and wasn't shaved. Her tight pussy hung low between her legs. The outer lips were still plump and pressed tight together. The inner lips couldn't be seen at all. Jack imagined the camel toe she would have dressed in tight pants.

Holly's breasts were small - you could suck the whole thing into your mouth - but they thrust out from her chest. The last third of her tit was puffy and entirely covered by her light colored areolas. The nipples were over half an inch long and thick. Exposed to the cold A/C they were growing longer and thicker.

He nodded. Walked over, took a nipple in each hand, and squeezed hard. The pain almost overwhelmed her. But underneath was pleasure - great pleasure.

"If we do this, it will be rough. Do you understand?" Jack demanded. Holly nodded. Jack twisted her nipples. "Do you understand?"

She began to tremble all over, her legs almost giving way. She grabbed his arms for support. A musky aroma rose from her crotch. She couldn't speak or move. All she could focus on was the painful pleasure in her nipples and the warmth in her pussy. Then she heard herself say "Yes, I understand."

Jack released her nipples. The pain stopped and the pleasure exploded. She felt a stream of liquid run down her leg just before she collapsed on the floor. She lay there as wave after wave of pleasure spasmed throughout her body. Before she finished her uncle picked her up and held her up like a rag doll.

"This is just between us until your parents return. Then it will stop. Completely. There will be rules and some of them you may not like but you WILL obey them. Do you understand?"

Holly babbled something incoherent. Jack squeezed her nipple hard. "Yes, I understand."

"First rule is that you will always be naked in the house unless we have visitors. As soon as you return from school, you will get naked. Second rule is that I will use you whenever I want and however I want."

"Agreed" she whispered again. As he twisted her nipple, she had a flash of exactly what this adventure would be like. It excited her, she wanted it. "Yes, I understand."

Jack had seen the pleasure she got from the pain. He marveled that one so young and inexperienced could feel that. "This is going to be interesting." he thought. Out loud he said "Clean up your mess." As Holly turned to get the mop he continued "Lick it up."

Holly looked at him like he was crazy. Lick it up? She didn't even know what 'it' was. It might be pee. Jack's face got stern. "Lick. It. Up."

Holly inhaled, about to argue. Paused. "Some of the rules I may not like but ...". She got on all fours and began to lick up the puddle. Whatever it was it tasted pretty good. Jack ran his hand over her upturned ass. One finger slid slightly into her pussy hole, Holly pushed back, and Jack withdrew the finger.

He had an idea. He needed to be sure she wasn't going to change her mind. He needed to test her resolve. Now. One indiscretion made public could be explained away; two weeks of indiscretions couldn't. He bent down, picked her up around the waist, and carried her to her room. He dumped her face down on the bed, rolled her over, and spread her arms and legs far apart like a 5 foot tall X. Holly said nothing but she smiled from ear to ear. She wiggled around getting comfortable for whatever happened next.

"Stay there" he commanded and left. He returned with a rope. He tied her ankles and wrists to each corner of the bed frame. Her legs were stretched wide, barely able to move. Her pussy was exposed with the lips nicely parted.

Jack went to work. He fondled each breast with his hand, rolling her nipples between his fingers until they were hard and and over an inch long. He bent down and sucked her left breast into his mouth, twirling his tongue around the nipple until it was even harder. Then he bit her nipple. Holly screamed and her arms and legs thrashed around. A few drops of pee oozed out of her pussy.

He bent down again and sucked on her right breast. Played with her nipple. Got it very hard. Holly tensed for the bite that was coming. Jack used his hand to play with her other breast. She relaxed and began to moan. Her uncle bit her nipple. Again Holly screamed and thrashed. Another little leak dripped onto the sheet.

Jack began working on her breasts for the third time. He played with both breasts with his hands. He played with her nipples. He sucked each breast in turn. When her body began to respond, he slowly slid his hand down her belly rubbing gentle circles from one side to the other. She tried to rub her thighs together but the rope prevented it.

Holly began to moan and writhe in anticipation. An unbidden thought came to her. "Mom and dad wouldn't like this." Her true nature that had been repressed so long came out and stomped the thought to dust. "But I like this. I really like this." She almost said something but didn't for fear her uncle would stop. Her uncle began lightly slapping her tits as one hand slowly moved downward.

He skirted the peach fuzz that guarded her pussy and slid his hand down the inside of her thigh. Came up the inside of the other thigh. The moaning got louder.

Her uncle had one hand at the top of her leg - between her pussy and thigh. She bit her lip to stop from screaming in frustration. He slapped her tits hard. She screamed and moaned. A little stream of pee dribbled down her ass. She twisted her hips trying to get his hand on her pussy.

A finger touched her slit and gently rubbed from top to bottom. There was a long pause. His niece was panting "fuckmefuckmefuckme". Two fingers opened her lips while another pushed further inside. Jack tapped the end of her clit. He pulled the sheath back and used two fingers like he was giving it a hand job.

Holly shuddered, moaned, screamed, and lost control of her bladder. Jack didn't stop as her urine struck him in the stomach. One finger went in her pussy. It pushed hard against all sides, stretching it out. Two fingers went in. Holly was small and two fingers barely fit. Cum dripped from her hole.

Jack slowly finger fucked her going deeper with each thrust. When he broke her hymen, she whimpered but her pussy opened a little more. He forced a third finger in. Jack began thrusting his fingers in faster and faster. She wasn't sure if this was pain or pleasure but she didn't want it to stop.

Holly continuously quivered. She babbled, her head thrashing back and forth, her arms and legs trying to piston up and down but stopped by the ropes. She had her first real orgasm, the liquid running down her ass. Jack kept going. "It's too intense" she thought "I'm going to die". She tried to say "No". She didn't have the strength. At the second orgasm Holly blacked out. Her uncle pulled his hand out of her pussy until she regained consciousness Her vagina felt stretched and sore and rubbery and wonderful.

He knelt down, her pussy facing him, and began to lick her clit. Holly couldn't say "No", didn't want to say "No" as her body convulsed with another orgasm. She couldn't see or hear anything except the pleasure that kept building until it became painful. Then the pain built until it became pleasure. Finally Jack stopped, straddled his niece, and undid his pants. He pulled out his cock - the first cock she had ever seen - and raised her head. "Suck it" he ordered. She tried but could barely get her mouth open.

Jack did most of the work. He stuck a pillow behind her head and put his cock in her open mouth. He jerked off, at the end spraying his cum on her face and hair. "Go to sleep now and we'll talk in the morning." He untied the ropes from the bed but left them tied to her arms and legs.

Holly was exhausted. She could barely roll over and curl up. Her eyes closed and she realized she had to go to the bathroom. She was too weak to get up so she peed on herself as she drifted off to sleep.