The days after Jackson’s return to Europe were some of the most boring of Hailey’s life. She went about her days as she usually did – gym, shopping, drinks with friends, and other leisure activities that filled her days since the end of high school – but much of what she used to like had lost its flavor.
Hailey caught herself fantasizing about blowing Jackson in a nightclub or maybe welcoming him naked at the door the next time he came over, only to remember that her fantasies were a month away, at the minimum. She visited lingerie stores and bought the sexiest pieces she could find, all to stave off boredom and convince herself she’d make up for lost time when Jackson returned.
It hardly seemed to make a difference. Hailey’s lust for sex flooded her brain, all she could think about was cock, and it didn’t take more than two days for her to start noticing the gazes of other men, even welcoming them.
Hailey had rarely dressed provocatively in the past, but that all changed as she started showing up to the gym in booty shorts, going shopping in nothing but a mini skirt, or going out for drinks in scandalously revealing cocktail dresses. The men around her seemed to appreciate it. Her trainer at the gym eyed her appreciatively, and Hailey didn’t discourage his looks. She arched her back and shook her ass at him every chance she got, asked him to correct her form more times than was necessary, and had to bite her tongue four times to stop herself from inviting him to shower with her after their session.
The shopping sprees and girls’ night out went about the same way. A rich-looking man in his forties asked her for his help in a Victoria’s Secret store. The man claimed he was shopping for his wife and needed advice, but it seemed to Hailey like he was in the market for a mistress. That didn’t mean she didn’t help him, though. Hailey laughed at all his flirty jokes and even agreed to model the lingerie for him when he asked. Unfortunately, his wife chose that moment to call him, which dimmed his enthusiasm and brought Hailey back to the real world as well. She escaped that store as quickly as she could, trying to ignore how wet the flirting alone had made her. What would’ve happened if I’d let him fuck me in the changing rooms? Hailey wondered. She guessed it would have involved a lot of screams, moans, and scandalized buyers. And me creaming on his cock, it would’ve involved that, too.
Terrified of her sudden desire for cock, Hailey returned home that night and brought herself to orgasm three times before she finally scratched that itch. It was back the next morning, though, so Hailey canceled her gym session and locked herself in the house for the rest of the day, trying to figure out what to do. Getting a new boyfriend would be optimal, but that would take time, and then she’d have to dump him the second Jackson returned, because it was that bastard she wanted to spread her legs for more than anyone.
Finding a friend with benefits was another option, but again, what would she do when Jackson returned? Keep fucking them both? Hailey groaned at the thought, that would be so hot, but then Jackson didn’t look like the type of guy who liked to share. And while Hailey did enjoy taking dick more than she had ever thought she would, she wasn’t an outright slut. She wouldn’t let men pass her around like that.
But what am I supposed to do then? That thought went through her mind a hundred times over the course of that Tuesday. She also told herself she’d just have to stop acting like such a slut a hundred times, but it didn’t make much of a difference. Not when the picture she’d posted specifically to get Jackson’s attention was still drawing guys into her DMs. At least thirty men had messaged her, some of them asking her out directly, some of them sending cheesy pick-up lines, but it was obvious they all wanted the same thing – to get in Hailey’s panties.
The only one Hailey responded to was Vincent, the millionaire father of one of Hailey’s former classmates. Vincent kept messaging her, and Hailey kept replying, mainly because she was bored and because fucking a man who was so much older than her seemed like the least likely scenario.
Vincent didn’t know that, of course, and if he had, he probably wouldn’t have seen it that way. An outrageous flirt, he kept offering to take her out shopping and then to dinner, kept asking her which brands she liked best so he could send her the most expensive pieces, and wouldn’t believe her when she said she didn’t have a boyfriend, as though that was the only possible explanation for her reluctance.
Hailey kept him at bay by pretending as though she didn’t take his offers seriously, as though all of it was one big joke, but the pictures Vincent painted in her mind became more vivid by the day. Hailey didn’t lie when she told him about her favorite brands, and she didn’t lie when she told him she liked the various dresses, necklaces, and shoes Vincent said he wanted to buy her. They were gorgeous, expensive, rare – Hailey could picture herself wearing them the second she saw the pictures he sent – and the thought of giving Vincent head in exchange seemed more appealing by the day. I’m craving cock anyway, so why wouldn’t I get a Chanel purse in exchange? And Vincent was pretty hot as well. Tall and strong, he was in good shape, even if he was bald. Hailey wouldn’t mind pleasuring him at all, or so she kept telling herself.
The worst of Hailey’s crisis finally ended when her mother returned from her vacation at the spa. Hailey could make as many plans for sex as she wanted, but it was a bit harder to pull them off with her mother in residence, even if the woman was more relaxed about her daughter’s sex life than most parents.
Her name was Victoria. She was in her mid-forties, and she essentially looked like Hailey’s older clone – she had the same auburn hair, the same slim build and long legs, and the same big tits and full lips. Where the two women differed was that Victoria was a gold-digger, plain and simple. She’d been married three times to extremely wealthy men, each time she took half their net worth when she divorced them, and she never tried to hide the truth that she’d married those men for the money, Hailey’s father included.
Since her third divorce, however, Victoria seemed to have concluded that she had enough money to fund her lifestyle until eternity, so instead of chasing down another investment banker, she started fucking younger men. Hailey caught her blowing her yoga instructor in their gym one morning and heard her fucking the pool boy when she thought Hailey wasn’t home. That’s why it didn’t come as a surprise to Hailey when Victoria returned from her spa vacation with a brown-haired man in his twenties, whose bulky arms, strong shoulders, and penetrating blue eyes had undoubtedly spread her mother’s legs without him having to say a word.
“Darling!” Victoria cried out when she stepped through the door and went to hug Hailey, her arms full of shopping bags.
“Hey, mum,” Hailey said as she hugged her back. “How was your trip?” That’s when Hailey noticed the young man come through the door, carrying the bags.
“It was amazing!” Victoria said.
Hailey wanted to roll her eyes. Everything her mother ever did was ‘amazing’, and everywhere she went and everyone she met, those people and places were amazing, too. Hailey suspected that at some point in her life, her mother had gotten used to telling every story as if she was telling it to one of her envious friends. As a result, Hailey spent her childhood listening to her mother’s stories and wondering vaguely why her mother sounded as though she was trying to make Hailey jealous.
“I swam every day, and then we had champagne and strawberries in the jacuzzi, and afterward we went to get a massage. You know how tense my shoulders get, and that’s where I met Philip.” Victoria took the young man’s hand. “We hit it off, so I invited him to stay with us for a couple of days.” As an afterthought, Victoria added, “I hope you don’t mind.”
By ‘hit it off’, Hailey assumed her mother meant that Philip had fucked her right there on the massage table, and she liked his cock so much, she’d decided to keep him. “Of course not,” Hailey said, conscious of the fact that she wasn’t wearing a bra as she shook hands with Philip. “Nice to meet you, Philip.”
“Nice to meet you, too.” Philip had a nice enough smile, and Hailey didn’t mind that his gaze lingered on her tits, either.
Victoria herded them both toward the kitchen, poured them all a glass of wine, and settled down to tell Hailey all about her time at the spa. Hailey was more interested in Philip’s muscles, rippling under his tight shirt, and the package that his grey sweatpants didn’t hide very well. He only had to shift once in his seat for Hailey to see exactly why his mother liked him so much. She nodded along at all the right moments as her mother told her story, but her mind kept going back to the pipe in Philip’s pants. Hailey saw her lips wrapped around it, slowly sliding up and down, leaving a trail of her saliva in their wake. She saw her skilled tongue working the tip, then licking it all over, lavishing his balls generously before she took him back in her mouth. When he got hard as a rock, Hailey would look him right in the eyes, and then she’d open her throat and let his shaft disappear into her mouth like a magic trick.
“Hailey?”
Hailey blinked. “Huh, what?”
“You with us?” her mother said with a smile.
“Sorry, I drifted away for a moment,” Hailey replied, smiling in embarrassment. “Actually, I need to go check something on my computer, we’ll talk later.” She ran up the stairs to her room and jumped on the bed. After fishing out her biggest dildo from the drawer, Hailey throat-fucked herself while she played with her pussy until she screamed around the fake dick as another orgasm wrecked her body.
*****
If Hailey thought that her mother’s return would put an end to the worst of her horniness, the next couple of days proved her wrong. Victoria’s presence did put an end to any plans Hailey might’ve had about bringing boys over, which would’ve been a good thing if Victoria’s slutty escapades around the house hadn’t increased Hailey’s desire to bring boys over.
Acting a like a randy teenager, Victoria let Philip fuck her whenever his heart desired, and it seemed his heart desired to have her in places where Hailey could easily see them. The first morning after their arrival, Hailey woke up and lifted the blinds on her winds, only to be met with the sight of her mother, riding Philip by the edge of the pool. They were both turned away from her, with no hope of noticing her watching them, so Hailey had plenty of time to examine the giant cock. Philip had to have a couple of inches on Jackson’s, and if her mother’s moans were anything to go by, they made a difference.
Even more than fucking his mother, Philip seemed to enjoy her blowing him. Or maybe it’s the other way around, and she likes blowing him, Hailey thought as she walked into the living room and saw Victoria kneeling between Philip’s legs while he watched a game. The latter option was probably true since it would also explain where Hailey’s oral fixation originated from.
Then, as if being surrounded by sex on all sides wasn’t bad enough, Philip started flirting with her. It wasn’t anything outrageous – he’d shoot her looks during shared meals, and he always seemed to know when she was watching him as he came out of the pool, and would grin at her and wink. It didn’t help that the man seemed to spend his every waking moment sweaty. Whenever he wasn’t pounding Hailey’s mother, he was in the gym, working out, so Hailey kept running into him drenched in sweat, his t-shirt clinging to his muscles, or on the way out of the shower, with nothing but a small towel to cover his cock (one time, she could’ve sworn she saw the tip dangling beneath the hem).
Hailey did her best to discourage his advances, but it didn’t exactly help that no matter how many times she practiced rejecting him in the mirror, she only managed two responses in real life: fleeing the room or trying to form a sentence as her eyes inspected every inch of his strapping body.
By the time Thursday rolled around, Hailey couldn’t take it anymore. It had become clear to her that Philip was using her mother the same way she had used countless men, and it was also obvious that Victoria was blind to this reality because Philip had fucked the common sense right out of her. Hailey frankly didn’t have any problem with any of that, feeling that both of them were getting exactly what they wanted out of the arrangement. That didn’t mean she was going to fuck Philip herself, though!
Her decision to keep her legs crossed came with consequences. The way Hailey saw it, she either had to spread her legs for someone over the next couple of days, or the last of her willpower would evaporate and she’d end up servicing Philip as happily as her mother did. Hailey thought long and hard about who to choose, and in the end, one message from Vincent answered her question.
Thursday evening, he was flirting with her again, and Hailey kept responding because she had nothing better to do, other than sharing a dinner with her mother and Philip. Vincent had spent the past week overcoming one obstacle after another on his path to persuading Hailey to go out with him, and as she lay in bed, they’d finally come to the elephant in the room.
Hailey bit her lip and wrote: But aren’t you married?
Vincent: Yes. But you know what’s the best part about going out with a married man, right?
Hailey felt her heart rate spike. She wrote back: What?
Vincent: You can trust us to never tell anyone what happened on the date.
Hailey’s pussy seemed to pulse when she read those words. She pressed her phone to her chest, squealing as she rolled on the bed, but then she got herself together and wrote back: So when are you picking me up?
*****
On Friday evening, Hailey stood at the end of her driveway, wearing high heels, a form-fitting white dress with long sleeves, a light jacket over it, and a crystal clutch purse. She put her hair in an intricate bun and did her make up to perfection – Hailey looked like a million bucks, and the expression on Philip’s face when he saw her walk out of the house was all the confirmation she needed.
Checking the time, Hailey looked up and down the block, wondering if any of the cars driving by belonged to Vincent. It might’ve been better to have him pick her up in front of the house, but Hailey didn’t want her mother seeing the car Vincent drove up in, in case it turned out to be some luxury brand. Victoria would never let Hailey hear the end of it, since she’d been forced to listen to her daughter’s accusing looks and derisive comments about her love for rich men for years.
Hailey’s concerns turned out to be well-founded because a minute later, a black Rolls Royce pulled up in front of her. The driver got out of the car, smiled at Hailey, and went to open the door for her. Hailey thanked him and offered a polite smile, and as the door opened she found Vincent sitting inside, wearing a tailored business suit, a glass of champagne in his hand. He seemed as tall as he looked in his pictures, though it was hard to tell with him sitting down, but he was as well-built as Hailey had assumed.
“Hello,” he said, smiling genially as he gestured for her to get inside.
“Hi,” Hailey replied, a bit shy as the chauffeur closed the door behind her.
Vincent looked her over and made no attempt to hide it. “My God, you are stunning.”
Hailey averted her eyes to hide her blush. “Thank you.”
Vincent reached out, put his fingers under her chin, and gently forced her to look him in the eye. “We’re going to have a great time tonight, you know that, right?” Hailey nodded and he scooted a little closer. His eyes went to her lips, and the next thing Hailey knew, he was kissing her. Her lips seemed to open for him without Hailey’s approval, and she moaned, vaguely aware that the chauffeur had gotten back into the car and driven off.
“You taste amazing,” Vincent said, his eyes alight. Hailey felt like a little lamb in his presence, but she loved every second of it, which is why she didn’t fight him when he grabbed her hand and pressed it against his crotch.
He’s hard already? Hailey thought as she started rubbing him through his pants. He seemed to like that, because he grinned and said, “You know, I thought about waiting until after dinner, but…” He unbuckled his belt with one hand and put the other on top of Hailey’s head. “I think I want to feel those lips around my cock before we even get there.”
Hailey froze, equal parts outraged that he’d dare to suggest such a thing and turned on by his daring. “But—But what about…” Hailey glanced at the chauffeur.
“Don’t mind him,” Vincent said as he pushed her head onto his lap. “He’s seen everything, nothing shocks him anymore.”
“But—mmph!” Before Hailey could finish the sentence, she had his cock in her mouth.
Moaning in spite of herself, Hailey started blowing him. She could taste his sweat on her tongue, but to her surprise, it only added to her enjoyment as she felt the pressure of his hand on the top of her head. Vincent’s cock was around five or six inches and not too thick, which made it perfect for a blowjob. She thought about the driver, watching her through the rear view mirror, and that spurred her to try a little harder, put on a proper show.
Vincent filled her mouth again and again, and she thrilled at his moans and groans. He must’ve fucked hundreds of women if he was so forward with Hailey, so she assumed impressing him was no small task. Hailey swirled her tongue, she sucked as hard as she could, but it was all teasing in the end – she had no intention of earning a load before they reached the restaurant, and Vincent didn’t seem to have any intention of giving her one, or he would’ve started fucking her face on the spot.
A few minutes later, after Hailey had become very well acquainted with every ridge and vein on his dick, she heard Vincent’s driver say, “We’re almost there.”
The pressure at the back of her head disappeared and Vincent helped her sit up straight again. Hailey looked at him, not knowing what to say since she’d blown him before they exchanged ten words, but Vincent pulled her into another kiss and then said, “Fuck, you are amazing.”
“Thank you.” Hailey smiled, and as the car approached the restaurant, she pulled a mirror from her purse and adjusted her make up and her hair a little, just to make it a little less obvious about what had been in her mouth a few moments earlier, while Vincent tucked himself back into his pants. The restaurant valet opened the door of the car just as the two became fully presentable again. Hailey had to wonder how many women had blown Vincent on the way to dinner for him and his driver to have mastered the timing so well.
The valet held out a hand and Hailey took it as she stepped out of the car, looking like a perfect rich lady as far as anyone was concerned. As she stepped out onto the sidewalk, she felt the eyes of the people waiting in line in front of the restaurant on her skin and had to suppress a shiver of delight. Hailey waited for Vincent to join her without turning to him, and when she felt his hand on the small of her back, she let him guide her forward. The security guards stepped aside, the velvet rope opened, and Vincent led her through the glass door into the restaurant.
The main room was poorly lit to allow for privacy, with round tables spread across the floor, every one of them occupied with as many people as it could host. The waiters speed-walked among them, their trays nearly bending under the weight of all the glasses of wine and scotch.
The second the maitre d’ saw Vincent, he stepped out from behind his little desk and smiled brightly. “Mr. Lynn, welcome!”
“Luke, how’ve you been?” Vincent replied as the two shook hands.
When the maitre d’ looked at Hailey, she merely offered a smile and a slight nod of acknowledgment, but kept her distance as all women who are spoken for should. “Please, let me lead you to your table.”
Vincent had her walk in front of him and Hailey made sure enjoyed the view as they walked among the tables, doing her best impersonation of a model on a catwalk. She didn’t mind attracting the gazes of the other guests of the restaurant, either, though for a different reason. Hailey looked like a prim and proper lady, one who wouldn’t be caught dead giving head in the back of a Rolls Royce, and the sense of deception added a whole new layer of pleasure to her experience.
The maitre d’ guided them through the main restaurant floor, but he didn’t take them to any of the available tables. A staircase hugged the second floor, and Hailey followed it up to the top where she found a few VIP booths on a balcony overlooking the main floor, with curtains in case the guests needed some extra privacy.
The three of them went up the stairs, and the man showed them to a booth at the very end of the balcony, the most private table in the restaurant. When Hailey saw it, she shot Vincent a knowing look, and the bastard grinned back at her as they took their seats.
Hailey continued to play the part of the quiet beauty when the waiter came to ask their orders, but when the wine arrived and the waiter shut the curtains, she raised an eyebrow and said, “How many women have you fucked in this booth?”
Vincent didn’t look up from the menu as he shrugged and said, “I don’t know, you’d have to ask Luke, he’s probably keeping count.”
Smiling in spite of herself, Hailey shook her head as she grabbed the menu as well. “Are you always so forward?”
“Yes.” He looked up from the menu. “Do you always suck dick so well?”
“No.” Hailey smiled coyly. “Usually I’m better.”
Vincent laughed out loud as he put the menu back on the table. “I have to admit, I’ve never seen a woman go from blowing me to being the classiest lady in the room so quickly.”
“What can I say, it’s a gift.” To underscore her point, Hailey extended her leg under the table, trailed up his thigh, and straight to his crotch.
Vincent shifted in his seat and regarded her with a mischievous look. “I see.” He raised his glass of wine in a toast.
Hailey mirrored him, working over his cock with her shoes as she said, “So what’s the craziest thing you’ve ever done here?”
Vincent tilted his head, thinking, and then said, “This one chick sucked me off while before we got our orders. When the waiter came with the food, she was under the table, giving me head.”
Hailey stifled a moan. She’d been barely holding on for the entire week, and the ride in the Rolls Royce pushed her over the edge. “Yeah?” she asked him. Then she set the napkin on the table, raised the tablecloth, and said, “Tell the waiter I’ll have the pot roast when he asks.”
Hailey only caught a glimpse of the shock on Vincent’s face before she slid under the table and crawled between his legs, grateful for the carpet that took it easy on her knees. Vincent spread his knees for her and her hands immediately went to work on his zipper. Hailey had it down in no time, and then she shimmied his pants down his legs. She’d only gotten to suck on his cock in the car, so she wanted full access this time.
When she had his pants around his ankles, Hailey leaned forward and pepper light kisses up and down his cock. The table meant she had to tilt her head to the side to find the space, but Hailey managed, and soon Vincent had her lipstick marks all over his shaft and balls.
Feeling that she’d teased him enough, Hailey decided to show him she had the most talented mouth he’d ever experienced. She wrapped her lips around his cock, hollowed out her cheeks from the suction, and started taking him into her mouth again and again with a hunger that surprised even her. What was it about kneeling for men and servicing them with her mouth that she found so irresistible?
Vincent’s cock was just to the size for a blowjob, not so big to make her jaw lock up or resize her throat, so she could swallow it without ruining her mascara. She did it over and over again and could feel him clench up beneath her every time. When the waiter came to get the order, she pressed her nose against his pelvic bone and stayed there, wondering if he’d crack.
“I’ll have the steak, and the lady will have the pot roast,” Vincent said, his voice a little strained. “That’ll be all, thanks.”
The second she heard the curtains close behind the waiter, Vincent pulled out of her mouth as he slid his chair back from the table. He grabbed her by the hair, pulled to her feet, and pressed her to the wall. Hailey was still wiping away some of the slobber that escaped her lips with her hand when Vincent had already pulled her dress past her hips and pushed her panties to the side. Then he grabbed her by the neck, pressed her face to the wall, and said, “Arch that back, slut.”
Hailey arched it as much as she could, even wiggled her butt for him, and felt him run his cock between her pussy lips before he slammed himself inside her. Covering her mouth to muffle the sound of her gasp, Hailey felt his cock fill her up, and then he started thrusting. Her cheek rubbed against the cold wall, but her ass rippled with his every thrust, her pussy so wet she feared she was dripping all over the floor.
“Yes, yes, yes,” Hailey chanted in a strained whisper. Why did she deny herself this pleasure for an entire week?
“You like that?” Vincent whispered in her ear, breathing deeply as he fucked her. “You’re addicted to cock, aren’t you?”
“Yes,” Hailey whined, nodding weakly. “Give it to me, please.”
“Fuck, you haven’t even spread your legs for me and you got me on the edge.”
Hailey had a naughty idea at that. Since Vincent had pushed her dress up to her hips, it was easy for her to lift one leg in the air. Vincent quickly caught on and shifted a little, so her ankle rested on his shoulder as Hailey did a standing split, years of ballet and cheerleading practice paying off.
“Oh, fuck,” he said and started fucking her with all he had.
Hailey would’ve screamed, but he started choking her. Trying to inhale but failing, Vincent’s cock hitting all the right spots, Hailey’s vision exploded in white. She felt her legs start to shake, and then the pressure on her neck disappeared, and her climax rolled over her like a runaway train.
Vincent’s strong arms kept her on her feet and pinned to the wall as he emptied his balls inside her, both of them trying desperately to keep their voices low. They stood nose-to-nose as they came down from their high, their eyes locked. Then Vincent smiled and shook his head in disbelief, while Hailey giggled as she took her ankle off his shoulder. Quickly putting her panties back in place and pushing her dress down to her thighs, she was back in her seat, sipping wine, when the waiter returned with her pot roast, looking none the wiser.