Forced: Babysitter Turned Fucktoy

Story Info
21-year-old babysitter is blackmailed into the Dad's fucktoy.
7.7k words
4.49
285.1k
338

Part 1 of the 2 part series

Updated 06/13/2023
Created 02/05/2023
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Chloe Moore was having a pretty mundane birthday. It was 5pm which meant she had officially just turned 21 years old fifteen minutes prior, but she had yet to be in a celebratory mood all day. Although it was the first day of summer, none of her friends were available; some were still trudging through exam week(s), some had already started summer courses in order to inch closer to graduation, and one had even been whisked away to Bali by her doting boyfriend of a year and a half. All Chloe had wanted to do was go out in the flashiest outfit she could think of consisting of the smallest garments she owned in order to finally present a legal ID to a bouncer, but this plan sounded neither fun nor wise without several partners-in-flirt.

It seemed as though she and her friends had lived out their craziest party days when they were well below the drinking age; they had gotten fake IDs in sophomore year of Catholic high school and developed quite the reputation amongst students, teachers, and nuns alike. They had been known to show up to school dances with a fifth of vodka in each of their coat pockets, host parties at which many a girl lost some aspect of her virginity, and sometimes get wasted in throngs of a dozen up on a rock in Riverside Park while the sun set behind them. But since they had accomplished so much debauchery so early in their partying careers, Chloe and her friends had matured quickly and moved on to more adult pursuits before some people her age had taken their first sip. So here she was, on the first day she was legally allowed to make horrible, drunk decisions, without anyone to do it with.

She had known this would be the case for a few days, though, so when her next-door neighbors had asked her to babysit on the night of her birthday, she accepted the job. Chloe was in her third year of college at Marymount Manhattan but still lived in the downtown apartment her parents had left her when they died; it was certainly home to many bittersweet memories, but she couldn't bring herself to move.

Besides, living on a block with so many families that had 2+ kids each was a built-in babysitting business that was too valuable to give up. It especially sweetened the deal that most of the dads she worked for were incredibly attractive, tall, and friendly, making her feel as if she were part of their families and giving her ample opportunity to sneak lots of thorough glances their way.

Chloe began to get dressed for work. She opened her closet and giggled to herself, not for the first time, about how her wardrobe was not prepared to make her look family friendly. On the contrary, her drawers were full of cropped t-shirts, tight tank tops, and obscene logos, while her hangers were dripping with miniskirts, short shorts, and flimsy sundresses.

The undergarments weren't much help; Chloe didn't even own a bra that wasn't transparent mesh, and her underwear consisted of strings, lace, or more transparent mesh (for when she wanted to match, of course). But it was her birthday and she didn't put much thought into looking "appropriate," or whatever that meant, so she chose her current favorite high-waisted jean shorts with six buttons instead of a zipper and a white, v-neck crop top with strings for straps that looked like they were about to snap any second.

Which is not to say that Chloe had the substantial, voluminous breasts that she always envied of her friends'. She had so much fun splaying her hands out on each of her friends' boobs when they were all happily tipsy, marveling at how even her not-tiny hands couldn't get a solid handful of them because there was just too much to grasp. There had been many a night those handfuls had led to tongues in bar bathrooms, but those are stories for another time...

Even so, Chloe had always been proud of her smaller, perky, ski-sloped boobs. They were the perfect size to bounce mesmerizingly under her tiny shirts without actually hurting too much when she jogged up and down the subway steps. They were the perfect complement to Chloe's long, lean legs that flared out slightly at the thighs, offering some jiggle to match her boobs and leading up to a full butt that had been her most-catcalled feature for years. Her waist tapered in for an elongated hourglass figure that had prompted both strangers and family friends to ask, "Why have you never gone into modeling? You're putting this body to waste," her whole life, to which she always responded, "Thank you, but I'd like to maintain my self-esteem if I can help it."

Standing tall at six feet, three of which being her frequently bare legs, Chloe was a confident girl used to feeling men's eyes all over her. She had gotten used to it from an early age when, despite the fact that she was in a Catholic school girl uniform (not the sexy kind- she hadn't yet learned to roll her skirt waistband three times to show off more leg, or to only slide on the sheerest of stockings), men on the street three and four-times her age had begun to ask for her number ("I could be such a good mentor to you"), invite her to their apartments ("it's only a block away, I swear!"), and even suggest she meet them at a club later ("I know the bouncer, getting in will be a breeze") before she turned even fourteen. Chloe had quickly figured out that being a kind, friendly person would waste a lot of her time at best and potentially cost her life at worst. Her "don't mess with me" face became her default mask as soon as left her front door every morning, and her mischievous smile was now reserved for the men she already felt comfortable with and knew well-enough to customize their teasing. In short, she was a subtle seductress.

With her revealing birthday babysitting outfit in place, Chloe spent a little extra time moisturizing her long legs and putting on some mascara, blush, and lip tint. She loved to resemble a blushing, naïve girl when she encountered the Clarkes; on Oliver, the effect was to hopefully make him wonder if her other set of lips matched the ones on her face, and on his wife, it was to nudge her towards assuming Chloe was innocent and nonthreatening to her marriage. Chloe's lips had always been full and pouty, often called DSLs in middle school (she'd had to look that one up on Urban Dictionary) and her mouth was more expressive than she liked.

Everyone could always tell how she was feeling based on the shape of her mouth and Chloe hated to be that transparent. If she was biting her bottom lip, she was anxious. If her lips were sucked together and in, she was thinking. If her lower lip was pushed out, she wanted something. And when her lips were ever-so-slightly separated, she was incredibly turned on. Luckily, she didn't think anyone had paid enough attention to her facial expressions to learn the key to that puzzle.

Chloe grabbed her bag, slipped on her sandals, and left her apartment just in time to walk the two minutes to her neighbor's front door by her booked time, 6pm. She knocked on the door but quickly let herself in as was the norm for everyone on the block. They were all friendly enough to know that if the door was unlocked, their friends were welcome to walk in as long as they announced themselves. Chloe could hear the clinking of plates and silverware, indicating the kids' dinner was underway, so she called out, "It's Chloe!" so as not to sneak up on anyone. She hung her bag on a hook in the entryway before strolling into the kitchen to join the family. The kids jumped up to hug her, yelling "HAPPY BIRTHDAY" right into her face enthusiastically even though she was mere inches away. Chloe laughed and scooped up the 6-year-old while hugging the 12-year-old with her other arm.

"Thanks, guys! There's no one I would rather spend my birthday night with," Chloe lied, but not completely. These kids were some of her favorites and did constitute a close second to going out drinking with friends.

Mrs. Clarke smiled knowingly, appreciating the white lie that made her kids feel special. She was dressed in a black velvet floor-length gown, her perfectly blown-out platinum blonde hair a stark contrast to the textured dark fabric. Although the gown was too long to see them, Chloe knew she was wearing impressively high heels, likely 5 inchers, based on the fact that Mrs. Clarke was a couple of inches taller than Chloe for a change.

"Happy birthday, Chloe. I really appreciate you coming over tonight, I know there are probably other ways you could be celebrating. My firm sprung an important event on me last minute so I won't be home until well past 2am," she sighed, already exhausted by a full day with the kids.

"It's no problem! I'm glad I could help out, and it'll feel good to ring in 21 by earning some money," Chloe said while glancing around. "Is Oliver joining you?"

Mrs. Clarke rolled her eyes just subtly enough that the kids wouldn't notice. "No, he's on a short trip out of town to visit his brother. He should be back at some point tonight but isn't sure what traffic will be like. He'll be the one to relieve you, and of course we'll pay for the whole night if he gets home early. Do you need anything before I head out?"

Chloe shook her head, knowing the kids' bedtime routine well. "Nope, we're all set. Have a good time tonight, we'll just be here throwing a rager in your apartment! Right, kids?"

The kids giggled and nodded, used to Chloe's jokes. Mrs. Clarke smiled and walked towards the door, her unseen heels click-clacking on the hardwood floors. "Oh, and feel free to have a glass of wine once the kids are in bed! You're legal now, after all," she said with a wink, then pulled a faux fur coat off of the coat rack and shrugged it on.

The door opened, clicked closed, and Chloe snapped into babysitting mode, prompting the kids to finish their dinner, brush their teeth, watch one show each, and climb into bed. Maybe because they knew it was her birthday and didn't want to give her a hard time, the kids didn't protest a single time and were asleep in their beds by 8:30. Chloe immediately found the bottle of sweet white wine she had seen in the fridge earlier, unscrewed the top, and poured herself a very generous glass. She was determined to enjoy her first legal drink with or without her friends' help, and now that she had permission from her boss, there was nothing stopping her.

Chloe carefully carried her glass of wine to the couch and turned on the TV. She took a few sips as she flipped through the channels, finally landing on an old episode of The Walking Dead. She had always thought Negan looked a lot like Oliver and smirked knowingly when, sure enough, Jeffrey Dean Morgan sauntered onto the screen. Her sips were turning more into gulps at this point and she realized she hadn't eaten much in the mad dash to get the kids to bed. The familiar warmth that came from drinking on an empty stomach started to descend over her brain as she chugged the last of her glass. She started to lean back against the couch pillows when she had a brilliant idea.

Chloe HATED being vertical. Laying down was always her preferred position, during sex and in general, but drinking wine while lounging on the Clarke's white couch was out of the question. So Chloe sped excitedly to the kitchen and opened the cabinet she knew from experience housed the youngest Clarke's sippy cups! Mrs. Clarke was very adamant that nothing ever damage her carefully curated, mostly white furniture, so even the 12-year-old was asked to drink from sippy cups when sitting on the precious couch. Chloe picked a cute pink sippy cup with a repeating cherry design and poured more white wine to the brim. She popped the cover on tightly and skipped over to the couch, satisfied by her own genius.

For the next two hours, Chloe lazily sipped at her juvenile wine cup while watching hot men defeat zombies on TV. Every time she stood up to pee (which was often- thanks, alcohol) she felt dizzier and dizzier, and soon her trip for another refill proved fruitless when not even a drop poured out of the bottle. She sighed grumpily and spun around the kitchen looking for another bottle, but didn't see one. Not one to give up, Chloe's drunkenly illogical brain decided to search the rest of the house for more wine. Maybe the Clarkes had a stash hidden away from the kids!

Her first instinct was to check the basement, but she didn't find anything there. All there was of any interest was a trunk full of thick, black fabric along with a riding crop and whip. Chloe vaguely remembered Mrs. Clarke mentioning that she had ridden horses growing up, but nothing about horseback riding indicated a wine stash, so Chloe returned upstairs.

She next explored Mr. and Mrs. Clarkes' bedroom, which she had been in briefly once or twice before just to shoo the kids away from it when they wanted to bother their getting-ready parents. She checked their closets and under their bed for an errant case of wine, but quickly forgot her mission when she found a strap hanging from the corner of the four-poster bed.

In her drunken curiosity, Chloe pulled at it which dislodged an identical strap in the corner at the foot of the bed. She followed the seatbelt-like material and saw that it disappeared into the gap between the mattress and the headboard only to return to view under the pillows. At the end of each strap was a leather cuff with double-buckles, and Chloe found a matching set at the foot of the bed frame.

It was then that Chloe became acutely aware of her clit rubbing against the middle seam of her denim shorts. She sat back on her heels which tightened the seam around her mound until it wedged in between her pussy lips. She could clearly feel that her pussy had unleashed some excited wetness at the thought of not only this very attractive couple being kinky, but of Oliver being adept at restraining and cuffing a woman to his bed. She had always loved imagining him above her, peering down at her with a stern face and a hungry look in his eye. In fact, she usually made an effort to sink into the couch or sit on the floor with his kids when he was around, going breathless at the sight of him towering over her and having to literally look down at her with a sense of authority.

In her tipsy state, Chloe's impulse control had flown out the window. She needed to get herself off and she needed to do so now. Eyeing a clothes hanger dripping with Oliver's ties, Chloe grabbed a silky black one and settled it around her neck before opening the bedside drawer where she suspected she'd find at least a vibrator. She hadn't quite been prepared for the assortment that rattled around as she pulled the drawer wider, but she didn't have the patience to inspect each toy so she grabbed a simple cordless wand and flung herself across her bosses' bed. Chloe parted her legs and pulled the tie taut around her neck, softly moaning at the simulated feeling of having her breath slightly restricted as she turned on the wand and brought it directly to her clit. Her hips bucked suddenly at the initial contact but she was soon writing fluidly against the buzzing toy in one hand and the smooth, tightening tie in the other.

Her moans intensified as the rolled her hips rhythmically against the combined efforts of the rumbling vibrator and rough seam still causing delicious friction against her throbbing clit, and she cried out one final time as she came violently then promptly fell asleep.

~~~

Oliver quietly let himself into his dark house, not wanting to wake his kids or startle Chloe. There had been nights when he and his wife had gotten home late to find her napping on their couch and the sight had always made him smile, but not for the same reason it made his wife smile; he smiled at the scene playing through his mind of him gently spreading her legs so as not to wake her up, slowly pulling her shorts down her impossibly long legs, and positioning his hard cock between her pussy lips before SLAMMING his pelvis against hers so that her first conscious sensation would be his throbbing member invading her tight, wet, warm, most personal of spaces.

Oliver was not what he would consider a "sane" man, and it didn't bother him in the slightest. He was very comfortable in his perversions and had no qualms about acting on them whenever the opportunity to do so presented itself. He wasn't reckless, though, and had been able to build an exceedingly "normal" life thanks to his intellect, charm, and, quite frankly, lack of conscience.

Oliver walked further into the house, hearing faint sounds of a TV show but not finding Chloe in her usual spot on the couch. He glanced over to the ajar bathroom door, which meant she wasn't in there either. Confused, he walked through the house and noticed the empty wine bottle on the counter with an open sippy cup next to it. "Those two things don't go together..." he thought as he continued on to check the rest of the rooms. He quietly opened the doors to his kids' bedrooms, finding only darkness and soft snores, then quickly closed them to retreat to his own bedroom. Besides the basement, it was the only room left.

As he walked closer his room, he could make out a long, sprawled out leg towards the edge of his still-made bed. For a moment, he wondered if his wife had gotten home early from her event, but he hadn't seen the telltale heels and extravagant coat hanging on the coat rack when he'd walked in. Besides, he knew his wife to neatly tuck herself in, never sprawl. Oliver kept his footsteps quiet as he crossed the threshold of his bedroom and smiled wickedly at the sight before him.

There, asleep on his bed, was the freshly 21-year-old girl he had just been fantasizing about fucking awake seconds before. Her tinted lips were parted, her tank top was pulled up to expose her soft, perky tits, and her hands were both still in the positions that gave away exactly what she had been up to before she fell asleep. One hand had his favorite black tie wrapped around her fist, the sturdy fabric leading up to where it looped tightly around her long neck, and the other still held his wife's vibrating wand that had fallen closely enough to its original position to give it away. His very young, very sexy, very much of a tease neighbor had fallen asleep tipsy and satiated on the bed he shared with his wife while she was supposed to be watching his children. This was unacceptable and perfect. Perfectly unacceptable.

Oliver, still moving slowly and without a sound, decided to make his fantasy come true. How could he not? He had been presented with the exact circumstances that had played through his twisted mind so many times, and they had even been enhanced for him considering she had clearly behaved in a very irresponsible manner that was drenched with sex. He didn't believe in signs, but Chloe practically had a glowing neon one above her softly tempting body flashing, "FUCK ME NOW." And how could a self-proclaimed predator like him resist that?

Without jostling his sleeping prey, Oliver reached around his pillows and fished blindly for the cuffs he knew were there. His hands ran into them and he pulled them into view before buckling a cuff to each of Chloe's wrists, waiting to pull the straps taut until he had her ankles cuffed as well. To accomplish that, he had to carefully pull her feet along the bed to reach the footboard's counterparts, stopping several times when he thought he felt her stirring.

Before long, he had successfully buckled her into all four cuffs and, despite the fact that Chloe had missed the small padlocks on each buckle during her drunken snooping, locked her into the restraints using a small key he kept on his dresser. He tightened the straps under each corner of the bed and voila! He had before him a sleeping, adorable, utterly trapped young woman.

Oliver couldn't believe his luck that she hadn't woken up yet. This allowed him the time he needed to take a pair of scissors and cut her out of her denim shorts. It was just as well; they bore an infuriating number of buttons instead of a simple zipper. She was even a tease in the little details. He hadn't necessarily expected her to be wearing any panties underneath them, considering all of the times she had "accidentally" flashed her pussy at him even when wearing skirts, but he still felt his cock twitch at the sight of her pink, already swollen pussy lips completely bare under her irreparable shorts.