Jennifer's Vacation

Story Info
A girl is blackmailed by her uncle and she grows to like it.
10.6k words
4.65
155.9k
300

Part 1 of the 6 part series

Updated 04/16/2024
Created 08/23/2022
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I enjoyed reading "Jennifer's Vacation," by Kmaf, and decided to put my own spin on his story.

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Part 1

Vacation

Vacation had finally kicked off and Jennifer's family had decided to go to sunny South Florida for a week with her uncle, his wife and their kids. They all decided to stay at a hotel near the beach near a strip crowded with stores and restaurants.

The whole family arrived at the hotel early on a sunny afternoon.

Jennifer was a young, cheerful young woman. She'd just turned 18 the week before. Her long blonde hair hung like a heavy golden curtain down to her slim waist and her bright eyes, as blue and vibrant as sapphires, sparkled with intelligence. Her tight, toned body was truly amazing. She had long golden legs and preferred snug tank tops that exposed her flat belly and tiny waist. Her incredible beauty, bubbly vivacious and humble personality, naivety, unconscious grace, stylish taste, and the fact that she was completely unaware of any of it drew people to her like moths to a flame.

She was very self-conscious of her body lately. She thought she was growing fat ever since her clothes started to fit too tight. She realized that when she started taking birth control pills a few months before, a necessity once things got serious with her boyfriend, her body had changed. Her perky breasts grew several cups and her hips widened, deepening her womanly curves.

Her Uncle Jimmy noticed the changes to her body immediately. He'd had the hots for his lovely niece for years... ever since she'd gone through puberty. Since then, he was always 'accidentally' touching her when walking by or hugging her a little too long and too tight. He always had a weird longing expression on his face when he looked at her. He gave her the creeps every time he visited, especially when she caught him trying to sneak a look down her shirt when she bent over, or "accidentally" rubbed his crotch against her butt when he thought nobody would notice.

In the past -- because of her youthful naivety - she never understood why he did what he did, but came to realize just how creepy and perverted he was as she grew older. Still, when he was around she never passed up an opportunity to tease him, to cruelly make him think he was about to see her bare charms only to snatch the opportunity away and dance off laughing. She secretly rejected the tingle and fluttery butterflies in the stomach she got when she caught him leering at her or when he "accidentally" touched her.

Jimmy was a typical perv. He was a short, overweight man with greasy, gray hair, carelessly combed over his bald head. He was an old man. At 69, a man his age should not stare at any teenage girl, let alone fixate on his own niece. Though Jennifer thought his inappropriate behavior towards her was obvious, somehow her parents and the rest of her family didn't have a clue about Uncle Jimmy's perverted tendencies. She never hid that fact that she thought he was absolutely disgusting, though for some reason she seemed to spend a lot of time with him when he was around, which is why her family was oblivious to his inappropriate behavior.

Her Aunt Linda was a great beauty just like her mother, a truly attractive woman. She was taller than Uncle Jimmy by about six inches, graceful and, most incredible to Jennifer, she was more than 30 years younger. They both referred to their courtship as a "whirlwind romance." They'd met 12 years before at her Uncle Jimmy's car dealership where she'd worked as his receptionist. They married a year later and had two children, a 10-year-old boy and an 8-year-old girl, her cousins. Jennifer couldn't understand and often wondered why her pretty Aunt Linda would marry such a disgusting and perverted old man. It was beyond reason.

Whirlwind romance my ass, she thought to herself.

When both families arrived at the hotel, Jimmy was blown away by his niece's incredible beauty. In the four months since he'd seen her she had become even more strikingly beautiful. He quickly realized her breasts had grown several cup sizes and now she carried herself with mature confidence and grace. He could tell she'd already worked on her tan because her skin was a beautiful golden color all over. When he knew only she was looking, he'd adjust himself and smile wickedly at her as she rolled her eyes and turned away with a huff.

"Hey Jennifer!" her uncle greeted her loudly, his eyes devouring her beauty behind his reflective sunglasses. He's the only one in her family who called her Jennifer, everyone else either called her Jenny or Jen.

He walked straight to her and hugged her tightly, running his large, callused hands down her lean back. He enjoyed the feel of her silky-soft skin and her slim fit body pressed tightly against his. She felt his clammy, sweat-soaked shirt and smelled the stale sweat coming off him like a noxious cloud. She gasped and forced herself to breathe through her mouth.

"Hey, Uncle Jimmy," she said gasped reluctantly, hugging him back briefly then tried to squirm out of his embrace, though she didn't try too hard. She was half-a-head taller than him, and she could feel his hot foul breath on her neck, chest and the top of her breasts. A jumble of emotions made her body quiver in his arms... disgust, confusion, embarrassment, impatience and others even more confusing.

"Well look at you, definitely becoming a grownup I see," he said with an admiring smile on his bloated face as he released her.

Bringing his large hairy hands up to her shoulders, he held her at arm's length and let his eyes trail slowly down to her large breasts and let them rest on her smooth cleavage. She regretted not buttoning up her shirt all the way before getting out of the car. She saw his eyes roll down her flat belly, long shapely legs to her dainty feet and then back up again. She was as tall as her aunt... five ten ... which put her proud breasts nearly at his eye level since he was only about five four.

She might have known he would gawk at her like this. The disgusting old pervert! She felt a shiver down her spine as her ugly uncle's small deep-set eyes devoured her. The host of confusing and conflicting emotions continued to go through her and she felt her nipples harden inexplicably and strain against her lacy bra.

As he tried to discreetly admire his teenage niece's large round breasts through his sunglasses, he noticed the outlines of her nipples pressing hard against her bra and shirt and her breasts seemed to swell as she took several deep breaths. She seemed to be breathing very hard for some reason. The tip of his thick pink tongue came and licked his lips at that wonderful sight.

After the members of her family greeted each other, they moved into the hotel to check in. Jennifer's parents were in a discussion with her aunt and uncle while she stayed with the kids in the lobby, her younger brother and sister and her two cousins. Uncle Jimmy appeared to lead the conversation. After the group broke, Jimmy headed to the front desk while her mother approached her.

"Jennifer, we arranged it so you don't have to sleep with the kids," she said.

Jennifer was overcome with relief and joy. She really wanted to experience a vacation without having to babysit the kids or go to sleep early, and she let her parents know as much on the drive there. It had always been tradition for all the kids to have slumber parties on vacation, but now that Jennifer was for all effects and purposes an adult, it didn't seem fair to foist the responsibility of watching the kids on her.

"Instead..." her mom continued, "your aunt will stay with them, and you can stay in the room with your uncle. That way you can stay up as late as you want and have a more quiet room. Sounds good right?"

Jennifer's eyes widened and her mind went numb. Was this really happening? In a room with her perverted uncle? No way! Once again she pushed down the heat and tingle deep in her core and fluttery butterflies in the stomach at the thought of being alone with her uncle.

"Can't I stay with Dad and you?" she asked pleadingly.

As she said this, out of the corner of her eye she noticed her uncle hand something to the desk clerk.

"Hon, your dad and I... well we never get alone time any more... so...we were hoping...," her mom said expectantly.

She didn't have to finish, and Jennifer cringed at the thought of what her parents might be doing in their room. Gross! So she huffed and looked at the floor. She didn't want to disappoint her mother, and without any other solutions in mind she reluctantly agreed. She didn't really put up much of a fight. Besides, she wouldn't have to babysit the kids, so that was a huge relief.

Once again, she felt a tingle down deep in her core and got butterflies in her stomach at the thought of sharing a room with her uncle. She told herself she was grossed out and furious about spending every night with her disgusting old uncle. She was convinced that was it, absolutely convinced.

Jimmy was a man of few words, and he usually went to bed late and woke up late in the morning; perfect for her rhythm as well. So maybe it wouldn't be so bad after all. Her uncle handed her a key card and told her he'd be up soon. He was probably hoping to catch her with her clothes off.

Uncle Jimmy couldn't believe her parents had bought his suggestion to have Jennifer swap places with his wife. He'd had some resistance, but he used his considerable skills as a car-salesman to get them to see things his way.

When she opened the hotel room and stepped inside with her bags, she got the second shock of the vacation. It had only a king-size and not two queen size beds. 'Damn it' she thought in frustration. While the bed was pretty big, the thought of laying on it with her old, dirt bag uncle made her skin crawl. At least she thought it did. Once again, a shiver went down her spine.

She immediately went to the phone and called the front desk.

"Hi, can you please send a sleeping cot to my room?" she asked politely.

She heard the clerk type away at a keyboard and waited anxiously for his response.

"I'm sorry, miss, we're all out of sleeping cots this week," the desk clerk said. "The hotel is full and we're packed with guests."

She sighed and hung up the phone resignedly. Little did she know that her uncle had handed the hotel clerk a thick wad of cash. He had told the man to feed her that line, knowing she might try to request a cot. He wasn't going to leave anything to chance on this once in a lifetime opportunity.

She put her stuff on the bed and decided to let it go and head to the beach. She could smell the sea and sand from the room. While the rest of her family was getting settled she decided to put on her bikini, grab a towel, a book and head of for the beach.

She slipped into the bathroom and locked the door, something she should not forget to do this week. It wouldn't be the first time her uncle "accidentally" walked in on her. He had never seen her naked, but he'd come close.

She put on her bikini top and realized she forgot to buy a new one... one that fit better on her recently-grown breasts. As she tied the small string behind her back she noticed how her breasts seemed to overflow her small bikini, creating what she knew would be very eye-catching cleavage. Again, she thought of her hideous uncle and a shiver went down her spine, making her tits quiver dramatically.

Shaking the unwelcome thoughts away, she admired her body. She was truly proud of her flawless tanned skin, long legs and tight firm body. Now that her breasts had grown she had nothing else to wish for, and she noticed most guys seemed to think the same thing. Even girls noticed, including her best friends, who all were super jealous of their ridiculously hot friend. Maybe she would try to convince her boyfriend to make the six-hour drive down to spend a few days with her.

All she had left to do was put on a summer dress or drape her towel around her and she was off to the beach. The last thing she wanted was to let her uncle leer and drool at her body. As she opened the door to get her dress, she was surprised to see her uncle sitting on the bed waiting for her to come out of the bathroom. Obviously startled and not amused, she hastily searched for her dress or towel, making every second count as her uncle sat there bug-eyed and practically drooling at the sight of his lovely niece in a white bikini two sizes too small. Ogling his beautiful niece's ample breasts bulging out of her tight bikini, her wide rounded hips and tiny waist made his cock grow with excitement.

This is going to be a wonderful week, thought the ugly old man.

She quickly pulled a dress over her head, visibly dissatisfying her uncle who still leered at her beautiful body.

"So, Jennifer, going to the beach I see? Good idea, I'll join you in a few minutes," he said delightedly.

Jennifer gave him a fake smile, rolled her eyes and walked out of the room, trying not to imagine what he would look like in a bathing suit. She didn't realize she put an extra sway to her hips as she walked out knowing his eyes were plastered to her perfect ass. She didn't know why she did it, but when she got to the beach, she laid out her towel, lay down and waited on the hot sand for him to join her.

As her uncle got ready to head down to the beach, he noticed Jennifer's discarded clothes on the bathroom floor. In her haste to leave the room, she forgot pick them up after changing into her bikini. Uncle Jimmy eagerly picked up her wadded panties.

"Ooohh, yes, yes, yes," he said, holding up the cute white panties printed with little teddy bears to his nose. He sniffed and kissed them, went to the bed, and dropped his pants. He then went into her suitcase and grabbed up more of her cute panties. She'd even packed a thong! It blew his mind that his sexy little niece would wear a thong. He laid the panties on the bed and wrapped the thong around his thickly-veined cock. He put her dirty panties up to his nose and inhaled his teenage niece's sweet scent as he stroked himself with her thong wrapped around his thick dirty cock.

"Mmmm... oh yes... you little tease... oh, your panties smell so good... oh, ugh, argh" he moaned as his cock exploded, shooting spunk on a wash towel he'd taken from the bathroom. He was careful not to soil her panties with his seed.

"Oh fucking hell," he said as he stroked his erupting cock, in what was certainly the best orgasm he's had in a long time. But he couldn't bask in it for long... his sexy niece was waiting for him on the beach.

The first day on the beach was exactly how Jennifer imagined it would be. He was wearing sunglasses but she knew her uncle's eyes were practically glued to her body as she sunbathed on her towel or romped in the water with brother and sister and their cousins. Mostly she crossed her arms over her chest to hide her scantily-clad breasts from his leering eyes, though her round, tight butt was nothing short of astonishing as well. While her uncle ogled her young body, other men also stared. Uncle Jimmy considered himself lucky since he was the one actually sharing a room with the young beauty.

Jennifer was tired that night and wanted to avoid her uncle at all costs, so she hurried to the room while he was with his wife and her parents. Since she hadn't expected to bunk with her perverted uncle, she hadn't packed more appropriate sleepwear. Her only nightgown was very thin and you could see right through it. Since she was slightly sunburned, there was no way she was going to sleep with a bra on, and her gown was way too revealing.

She decided to put on her largest t-shirt with a fresh pair of panties and nothing else. She pulled down on the bottom of the shirt to make sure it covered as much of her body as it could before she climbed under the sheets. Since she was sunburned it was too hot to use a blanket so she stripped it off the bed. Little did she know her uncle had turned up the thermostat to make the room uncomfortably hot.

By the time Jimmy got back to the room she was on her side pretending to sleep, hoping he would leave her alone. He did, he simply climbed under the sheets next to her and turned on the television with the volume very low. Eventually she did fall into an uneasy asleep.

Uncle Jimmy couldn't sleep because he was so excited sharing the bed with his lovely niece. He stayed up late with the television on and softly stroked his smelly cock. He looked at his niece breathing deeply with her back to him and decided to push his luck.

"Jen," he called in a soft hush. "Jen, wake up."

Her breathing was deep and regular and he knew she was sound asleep; he slowly peeled the bed sheet down her toned legs, careful not to disturb her. His next move was to softly pull the bottom of her t-shirt up the back of her taught tanned thighs.

"Oh... yes, yes..." he mumbled as he carefully pulled her shirt up to the waistband of her panties, exposing her round, perfect bum. She wore soft pink panties that accentuated her buttocks' perfect shape. The light illumination from the television offered him a great view of her perfection.

"Mmmm... such a succulent little tush" he said as he began to stoke his throbbing cock.

Uncle Jimmy started to lose control as he ogled her sexy ass. He wanted so much to pull her panties down, but he knew she would scream and he would be in a heap of trouble if she awoke. Instead he beat his cock harder.

The sound of his fist pumping up and down his fat prick made a 'thwap thwap thwap' sound and the bed started to shake with the force of his enthusiastic masturbation.

It was at this point that Jennifer woke up. There was an odd repetitive sound and shaking coming from her uncle's side of the bed. She was too mortified and disgusted to turn around, so she closed her eyes and prayed that whatever was causing the sound and shaking the bed would be over soon.

She knew he was masturbating. She told herself she was grossed out and shouldn't do anything that would alert him or make a scene. The vacation would be ruined for everyone if she fussed and she didn't want it to end before it got started. So she kept her eyes closed and tried to fall back to sleep. She inexplicably felt her body flush hot, her nipples turned hard as pebbles, and her pussy moisten at the thought of what her uncle was doing only a foot away from her. It was all she could do to keep herself from turning over to catch a glimpse. She'd never seen a man masturbate. She was curious, but not that curious.

Little did the hot young girl know her dirty uncle had lifted up her t-shirt and was staring at her panty-covered teenage ass. She shut her eyes as hard as she could and tried to think pleasant thoughts, instead of listening to her disgusting fat old uncle masturbate, though she was hyper-focused on the sounds he was making. Finally she heard him hold his breath then grunt and groan and she knew he was coming. It seemed to last a long time, she listened to his muffled grunting moans and the slopping, squelching sound of his cum-covered hand on his nasty cock and felt the bed shake even harder.

Mortified, she tried to fall back to sleep after the old man's eruption ended, but she was in shock and, though she'd never admit it to anyone, she was dripping wet and so aroused that her mind was a jumble at the eroticism of the moment. She heard her Uncle Jimmy clean himself up, settle down, roll over and start to snore loudly. She drew her pillows over her head and closed her eyes... trying to think of her boyfriend, the beach, and other happy thoughts... she drifted off to sleep to the "thwap, thwap, thwap" sound of her uncle's fist pumping his cock and the groans of his pleasure as he came.