Michael Steele awoke to the fragrance of an orchid-drenched, sweet lavender perfume, and all-out intoxicating femininity. The fifty-eight-year-old gave his troublesome back a good, long stretch as he inhaled the unmistakable scent of his much younger girlfriend and lover, Lindsay Anastacio. The mere thought of this chick could overwhelm Michael – or Mike, or better yet, Sammy – and cause his emotions to go berserk. Her scent was distinctive and mingled with the aroma of indulgent sex that still lingered throughout the bedroom after the wild, passionate night they’d shared together, their first in Hawaii.
Lindsay was still fast asleep with her body snuggled against Sammy’s. His eyes twitched open and a nasty, telltale grin appeared on his face. Good God, babygirl, you were so responsive and expressive when I fucked you last night – just the way I prefer it – and you were begging me to pump your ass full of cum.
And boy, oh, boy; did I ever.
Sammy growled at the memories. After several minutes of making out and feeling each other up past midnight as hot water cascaded down their bodies in the hotel shower, Sammy bent Lindsay over the bench within. She splayed both hands across the tiled wall and presented her ass to him properly. They’d fucked for hours on end throughout the suite already, but Sammy had enough in reserve to step behind Lindsay, latch on to her hips, and slide his hard, throbbing dick into her rectum.
Her ass is total perfection, tighter than all Hell.
The two lovers moaned out once they were joined. Lindsay, thankful for this surprise vacation in paradise and all the other generous gifts Sammy had bestowed on her, pressed back into him as hard as she could and begged him to use her. Within seconds, Sammy seized a fistful of hair, yanked hard, and was thrusting away. The fullness made Lindsay sob in shame and discomfort. Getting fucked in the ass hurt, but nowhere near as much as it felt good – the vigorous burning, its taboo nature, and the undeniable sense of surrender that went along with it.
Winding his hand tighter in her mane, Sammy pulled Lindsay’s head back so far that it strained her spine. He put his lips close to her ear. “You’ve been a bad girl, haven’t you? You deserve to have your ass fucked hard, like a slut, don’t you? Don’t you?”
“Yes!” she cried out. “God, yes! Make me your slut!”
Lindsay was the sexiest woman Sammy had ever seen, ever touched, ever pinned up against the wall, and the constant, overwhelming desire to bury his cock as deep as it would go inside her was too powerful to withstand. He surged ahead, his hips audibly slapping her ass as the whole of Lindsay’s body writhed and struggled against his.
Sammy decided to work a half-day this past Friday, thus beginning his two-week vacation early, yet spent all morning talking to his eldest daughter, Carolyn, in his Salt Lake City office anyway. Sammy informed Carolyn he was ready to take the next step and propose to Lindsay.
Of his four children, all adults with children of their own, Carolyn was the only one who wasn’t upset with Sammy (or flat-out condemn him) for leaving their mother and his wife of thirty-nine years in favor of eighteen-year-old Lindsay.
Carolyn told Sammy that he didn’t need permission or validation from her or anyone else. “You worry too much about what others say about you and Lindsay, Dad. You need to stop and focus on what you and her want, and what’s best for you. Not anyone else.”
Lindsay was an incredible girl and Sammy wanted to spend the rest of his life with her. He’d been so damn preoccupied with all the negativity from the rest of his kids – they were angry about what he’d done to their mother and full of doubt as well, claiming the difference in his and Lindsay’s ages was too significant for anything to last long-term between them – but he wasn’t giving what she and him had built together enough credit.
Indeed, why worry about what others (even some of his closest friends, too) thought when his relationship with Lindsay, though just five months old, was as rock-solid and stable as could be? The sky was the limit. Why did Sammy need confirmation from others when he was assured what he and Lindsay had was so right?
Even if it was vastly different than a typical relationship.
From innocent, small-town high school graduate to legalized prostitute in a Nevada brothel, all the way to submissive sugar baby for a gentleman forty years her senior, Lindsay’s life had changed dramatically since the summer months. She was living with Sammy in a sprawling penthouse loft in the East Bench district of Salt Lake City, driving a brand-new BMW 4 series 440i xDrive convertible, and had a stipend of $20,000 being deposited into and spread out over various personal savings accounts every Friday like clockwork.
… Just for being my personal sex puppet. My toy.
Sammy chuckled at the thought. Lindsay takes care of me and I take care of her. It was mutually beneficial, and Sammy saw nothing wrong with it. This type of steady, long-term arrangement with a working girl was what he’d always wanted, right? I may have lost my wife and marriage because of it – the mother of my children, too – but it was a small price to pay.
Lindsay insisted the $20,000 Sammy wired into those accounts every week wasn’t necessary. In fact, she hadn’t even touched – let alone used – any of that money yet.
What a doll. She claimed the two credit cards Sammy gave her and said to buy whatever she wanted with them, no matter the cost, was plenty more than enough. But I insisted on the weekly allowance. Just let that balance pile up and earn interest. Even amid a messy divorce, Sammy had money to burn, and nothing made him happier than showering luscious, exotic prostitutes like Lindsay Anastacio with his riches. I’ve spoiled her rotten already but am far from done.
The ongoing compensation was inconsequential to Sammy, a byproduct of their relationship and how they met. I see no reason – if and when we get married – for it to stop. Sammy was intent on keeping the deposits going. She’ll need them one day when I’m gone.
Carolyn had another valid point. Sammy had to follow his heart and do what felt right to him. “I know things haven’t been the best between you and Mom these past couple of years, Dad, so I’m not going to hold this against you like Scott, Cassandra, and Marcus do. I have no reason to and, quite frankly, neither should they. You’re my father and I want you to be happy. You deserve it. You’re their father, too, and I wish they’d see things the way I do.”
Of course, Carolyn didn’t know – nor did any of Sammy’s other children – that Lindsay was once a prostitute and that’s how he’d met her.
By paying her for sex.
She technically still is a prostitute.
Carolyn had always been Sammy’s favorite child and she’d supported him no matter what. Thus, the reason why she wasn’t upset he’d left her mom in favor of another woman. Growing up, Carolyn had been level-headed and wise beyond her years. Full of compassion and understanding, she realized there were two sides to every story.
But if Carolyn knew the truth about Sammy’s relationship with Lindsay – specifically how they met – Sammy feared he may lose her too.
I can’t lose Carolyn, so she can never find out. Everyone, even her, has their limits. Besides, none of the kids need to know about my whore addiction.
“If being with Lindsay is what you want, Dad, and she makes you happy, I can’t speak for the others. But me, personally? I’m all for it.”
Sammy was inching closer, but he wasn’t going to propose to Lindsay. Not yet, but soon. Very, very soon.
Her nineteenth birthday was two weeks ago and Sammy surprised her with a pair of airline tickets and the promise of a week-and-a-half in Hawaii at perhaps its most luxurious resort, Four Seasons Resort Lanai, on the small, secluded island of Lanai. Perhaps during their tropical excursion, Sammy would ask Lindsay to be his bride and he’d finally get to put the expensive ring he’d purchased back in October on her finger.
Truth be told, she’s evolved into a hell of a lot more than a whore to me.
Sammy closed his eyes and images of Lindsay flooded his mind. They’d shared and done so much together since moving into the penthouse this past August. I abandoned everything for this girl and it’s the best decision I’ve ever made.
Sammy went out with Lindsay five or six nights a week and always had a great time. The fact that I’ve been able to keep up with her and not wear myself out is fantastic and makes me feel young again.
There was the September afternoon they went ziplining through a 143-acre park in downtown Salt Lake City. Sammy will never forget the haunted house they visited on Halloween night either. Lindsay was terrified and clung to him for dear life! They tried indoor and outdoor golfing, sport fishing at Strawberry Reservoir, and spent an entire day in Big Cottonwood Canyon. Sammy held Lindsay’s hand and offered encouragement as she got her first-ever tattoo, a tastefully done butterfly spreading its wings (signifying Lindsay’s newfound sense of freedom) on her lower left abdomen.
They’d already been on another trip together too.
Sammy had a couple of vacation days back in August that allowed the perfect opportunity to divert from their emerging routine and do something fun and unique as a couple. It took some convincing on her part, but Lindsay suggested they go someplace for a few days. Work had been rough on Sammy, as had the drama with Barbara, and Lindsay wanted him to have a chance to step away, so to speak, and recharge his batteries.
He had mounds upon mounds of unused credit card reward points, so they had their choice to go anywhere they wanted, free of charge. Airfare, lodging, and rental car costs would all be taken care of.
Lindsay suggested they hop on a plane and travel to Washington, D.C. to tour the Smithsonian National Air & Space Museum. It was a tempting idea for Sammy as he was an aviation buff and had always wanted to visit the nation’s capital. This particular museum, a sprawling mecca featuring one of his greatest hobbies and interests, was number one on his bucket list too.
They almost decided to go there, but Sammy asked Lindsay what the one place was she’d most like to visit. Her answer? Hawaii, naturally, but such a trip was out of the question since they only had a five-day window for their vacation. If they were to go to Hawaii, Sammy would want to spend at least ten days there, if not a whole two weeks (their current trip would comprise eleven days).
Lindsay’s second choice? Kalispell, Montana.
Sammy had never even heard of Kalispell, Montana. It’s a small community located seventy-five miles south of the U.S.-Canadian border with a population of 22,000. Browsing a map, nearby town names include Whitefish, Lost Trail, and Lonepine. At initial glance, it seems desolate.
Yet, Kalispell has an international airport nearby and, what attracted Lindsay, is it’s considered the gateway to Glacier National Park. She loved the outdoors – hiking, boating, camping, all things nature – and had forever dreamed of one day visiting Glacier National Park. Sammy enjoyed the outdoors as well, so told Lindsay the Smithsonian and Washington, D.C. could wait for another time. They’d spend their first vacation together in Kalispell.
Back in the present moment, the rawness of Lindsay’s beauty caused Sammy’s heart to sputter as she continued to snooze oh-so-peacefully next to him. Her golden hair was a disheveled mess and her face was all-natural, free of any mascara. Her lips were moist and gave Sammy a familiar desire: to put his dick between them. Her lacey pink chemise was riding high – its hem bunched around her abdomen – and the matching G-string she wore to bed last evening was long gone.
But he didn’t reach for Lindsay and pull her closer, though he wanted to. The urge was so intense that his fingers were twitching. He maintained his composure and kept still, and his mind began to drift.
Sammy thought back to that August week and a delighted, full-blown smile overtook his face. The lone reason he agreed to go to Big Sky Country was because Lindsay seemed enthralled by Glacier National Park and everything about it. It was high on her own bucket list.
Sammy was expecting to spend those five days in the middle of nowhere but learned Kalispell was the coolest place he’d ever been to. It featured mountains laced with hiking trails through lush ecosystems, torrid rivers for rafting and kayaking, vast lakes ideal for boating, an endless choice of quality restaurants, and the friendliest, most downhome locals he’d ever met.
Every single day they went hiking and exploring – be it along Highline Trail, Piegan Pass, Iceberg Lake, Virginia Falls, or Herron Park – then they’d spend the evenings enjoying local cuisine and later fucking next to the fireplace in their chalet. The whole experience solidified Sammy’s feelings for Lindsay and made him realize that for the first time in his life, he was legitimately happy.
All thanks to her.
Sammy thought about that word for a moment. Before Lindsay popped into his life and knocked him off his feet, Sammy thought he was happy. He had a job he enjoyed, made great money, and spent plenty of time with the grandkids.
Yet, Sammy now understood he’d never been happy. At best, he’d been content, treading water. His life had been on autopilot for the past three decades because of his soon-to-be ex-wife. Realizing this and doing something about it was a long, grueling process.
Sammy didn’t miss Barbara and felt no remorse about leaving her. She’ll get a huge settlement – tens of millions – in the divorce and will be set up for life. The monotony of thirty-nine years of marriage, doing the same boring things day after day, week after week, year after year, had stripped away any remaining positive aspects of their union. It got to the point where I didn’t like being with Barbara anymore. She was never willing to compromise on anything. In the end, we had little in common.
Sammy found excitement at the Nevada brothels – they were a refuge of sorts – and it was a major reason why he kept going back for more. He was fascinated by the young women who worked at them and eventually found his soulmate at Happy Ending Ranch.
Being with Lindsay these past several months offered Sammy a glimpse of what happiness truly was. He learned that he was never in love with Barbara to begin with. Hell, I thought I was in love with Alana back in the day, too, but now realize I wasn’t.
I’ve never been in love until I met Lindsay, period.
Having her as his live-in girlfriend (and an unabashed plaything, too, to be honest) taught Sammy what true love was. She was a part of him now and he wanted to devote every waking moment to her from this point forward.
Despite all their many differences and the challenges that awaited, Sammy wanted to marry Lindsay, care and provide for her, and help create and raise babies with her. Spend the rest of eternity alongside her.
Was that too much to ask for?
Our sex life is fantastic too.
A strict, no-nonsense CEO and chairman of a pharmaceutical juggernaut worth $200 billion, Sammy found himself addicted to the infinite pleasures of being with a tight, hard-bodied teenager whom he could spank, fuck, bind, and whip at his leisure. Sammy’s ongoing guidance and discipline had morphed Lindsay into the perfect submissive princess.
Best of all, Lindsay swears up and down that she’s never been happier and more fulfilled in her whole, entire life. I’m a lucky guy, huh? Says she wouldn’t trade what she has now for anything.
… A small price to pay, indeed.
But certain sacrifices had to be made in order for this idyllic fairytale to become a reality. I know Lindsay feels guilty for quitting Happy Ending Ranch without any notice after a mere three weeks of working there. She claimed Pamela was good to her from the start and in quitting so suddenly, Lindsay realized she hurt Pamela something fierce.
Did I leave her any choice? Sammy offered Lindsay the world on a silver platter if she’d move to Utah and live with him. He’d separated from Barbara days earlier and relocated into a sprawling penthouse in the shadows of the Wasatch Range, a gorgeous preserve where Lindsay could hike and explore to her heart’s content. Sammy chose this specific area, in fact, because Lindsay loved everything to do with the outdoors.
Thus, their trip to Kalispell. I’d go back to Montana with her in a heartbeat too. No doubt. All she had to do was ask.
If you’re anything like Sammy and enjoy stumbling out into the wilderness with no rhyme or reason, certainly no particular destination or even a map, you’d love Kalispell as well. Glacier National Park is abundant with wildflowers and pines, striking landscapes, and outstanding, panoramic views. It’s an amazing spectacle.
There were many more sacrifices too.
Poor baby; her mom and dad all but disowned her once she told them that she was in a serious relationship with a fifty-eight-year-old man. Lindsay’s father, who was forty-six, couldn’t wrap his head around the concept. It was the straw that broke the camel’s back, too, because her mother threatened Evie a few days prior and she promptly fessed up about Lindsay working at the brothel. Her mom blew a gasket and Lindsay hasn’t had any contact with her family since.
The forced separation was catastrophic to her psyche.
Again in the current moment, Lindsay awoke, startled. Sammy had a hand between her thighs, but she couldn’t see him at first because she was facing the opposite way. The bedsheet had been pulled down, her chemise pulled further up, and those thick, familiar fingers played her clitoris like a violin.
“Good morning, babygirl.” At the sound of Sammy’s deep, authoritative voice, Lindsay glanced back over her shoulder and whimpered. Rugged and handsome in an arrogant, worldly way, Sammy was naked and ready to indulge in his selfish pleasures again.
I want you.
The feeling was mutual. The one thing Lindsay craved more than anything was riding Sammy’s cock with her favorite butt-plug stuffed in her rectum, not just to three orgasms, but to as many as Sammy would allow.
Half-awake, she kept her eyes on his hard cock.
“Turn all the way over on your tummy, sweetheart. It’s time for your morning fucking.”
“Yes, Daddy.” Her wrists bound in fuzzy pink cuffs to the pink collar around her neck, Lindsay cleared the morning gravel from her throat and obeyed. The cuffs weren’t uncomfortable anymore – she was accustomed to them by now – though they forbid her the range of motion that a regular person has. Sammy generally kept her restrained overnight because he believed it helped provide a stern reminder of her place in their relationship.
On her knees before him and ready to please at all times.
Lindsay propped herself up on her elbows with both hands close to her face. She raised her ass as high as it would go and gave it a tiny, little shake, silently taunting her owner.
Oh, she was going to pay for that. Naughty, little brat. Passion surged throughout Sammy’s veins at the sight of his concubine so vulnerable and inflamed, trying to gift him her charms properly.
“Please fuck me, Daddy. Please, please fuck me.”
Without a word, Sammy presented the head of his cock to Lindsay’s pussy, grasped her thighs, and spread them to allow the best angle to enter. Lindsay raised her head and again turned her face to gaze back his way. “Oh, Daddy. Make me your whore.”
Sammy pushed inward and began to thump her hard over the bed. “Oh, fuck. Oh, yeah, right there. You’re my good girl. Such a sweet little pussy … good girl. Hmm, that fuckin’ pussy. Oh, yeah.”
Sammy offered a series of powerful thrusts that caught Lindsay’s clitoris in all the right ways. He rocked her body as well as her senses. She was tight but took every inch of him regardless. He’d made sure of it. “Oh, yes. Oh, so good. Look at you. Yes, you’re a little whore. A good, little whore who knows her rightful place.” He gripped the back of her neck with his left hand, drew back with his right, and delivered a sound, solid smack to her upturned backside.
“Oh, Daddy! Daddy!” The heat flared and her body bounced with the forceful slap of his hand.
“You like being spanked?”
“Yes! Yes, I do! Please, do it again.”
He followed with three additional swats, each harsher than the one before it. Her foot kicked up involuntarily and walloped his side. Lindsay gasped, grunted, cried out, and pushed her ass into his pelvis yet again, but none of this was done because she wanted her fucking to end. Lindsay knew that Sammy preferred she take her punishments without any resistance – like a good girl should – but right now, how was that possible? His hand felt like a hot brand each time it spanked her.
“This little pussy of yours constantly cries out for my cock, doesn’t it?”
Lindsay again nodded, her face now buried in the bedding as he tormented her.
“Oh, you’re such a greedy cunt. So needy too. And entitled. Always been that way, haven’t you? An insatiable, little cunt who tends to pout when she doesn’t get what she thinks she deserves.”
The nineteen-year-old flinched as Sammy peppered her ass with another heavy-handed swat before landing one on the opposite cheek. “Oh, babygirl. I’m gonna put some sperm in your pussy to start our day off right. I know you have an IUD implanted to make sure you won’t get pregnant. But at some point – maybe soon – we’ll have it removed by the doctor and I’ll put a baby in your tummy. I’m not sure exactly when, but the decision will be mine.”
“Oh, yes! Yes! I’d love that.” Lindsay was grunting now, thrashing, as he pumped away. “That feels so good, Daddy! Please, please, spank and fuck me harder!”
“This little cunt has had twenty-seven different cocks in it since the first time I fucked it back in July at the whorehouse. My, oh, my; you were quite a promiscuous dick-taker while in Nevada. Weren’t you, babygirl?” Sammy delivered yet another painful slap to tender flesh and it was already turning red. Lindsay tried to roll her hips away – again on instinct – but the conqueror’s grip he had on her neck anchored her in place.
“I opened your pussy up during our first party, didn’t I? The first night you ever took dick in exchange for money, hmm? Yes, indeed, I opened it more than ever before and it was so tight I came quicker than I wanted to. Little, virtually untouched eighteen-year-old pussies tend to have such an effect to men my age, don’t they? You’re a bit looser now, honey, thanks to all the dick you took over those three weeks, but it’s still like velvet in there. Sweet, incredible, tight velvet. Feels like fucking Heaven.”
Lindsay continued to cry out as she was ridden hard. Sammy knew his words were having a profound effect and increasing the ache of her growing arousal. It was why he wouldn’t shut up. She genuinely got off on him talking down to her like this.
That, and the spanking. Lindsay loved being spanked. Sammy had watched her achieve multiple orgasms from simply being punished in the past.
“I’ve always wanted a twenty-four/seven bed girl like you to do with as I please.” Lost in his own pleasure, Sammy spoke his mind. “I deserve this. Someone who knows I control their mouth and cunt, and especially their ass, and respects me because of it.” Sammy began to blast Lindsay with brutal force as both hands landed a flurry of slaps across her backside. “You’re a living, breathing sex doll who I can’t get enough of, babygirl. I’m going to keep fucking you every day. Make you suck my dick. Use your incredible, little body for my own pleasure. And you’ll enjoy every minute of it as much as I do, if not more.”
Lindsay nodded, wailed out thunderous and loud, and the degradation – not to mention the physical sensations – made her pussy implode, and she reveled in the sweet, intense pleasure. She came, crying out, her face looking brighter than the sun.
The thought of the freedoms he had with Lindsay’s body brought Sammy’s passion to its conclusion as well. He gave a grunt as his cock pulsed away inside her and she couldn’t help but to suppress a listless sob at the feeling.
Sammy withdrew, walked to the side, and wrapped a towel around his hips. They had a fun and eventful day ahead of them, their first full day in Hawaii, and he knew it. Lindsay, her ass twitching, clung to the headboard and gasped in deep, uneasy breaths.
She heard a click from underneath her chin.
Lindsay bit her lip as a cool, silver chain brushed along her cheek. It was her BDSM leash. Sammy held the metal and gave it a moderate tug. “You’ll go on your hands and knees with me to the washroom and give me a full scrub down and shower massage. If you do a good job, I may reward you, and eat out your pussy afterward.” He pulled on the leash again and arched his eyebrows. “C’mon, down you go, girl. Down.”
“Yes, Daddy,” she responded in a barely audible tone. Indeed, Lindsay was light years away from her old life in Citronelle and everyone she’d ever known and loved. A year ago, she would’ve never imagined that one day she’d be living in Utah – but on vacation in Hawaii, of all places – and kneeling in skimpy lingerie, much less crawling in skimpy lingerie, and being led around on a leash by a wealthy fifty-eight-year-old man.
Her Daddy Dom.
Though exhausted after their vigorous morning ritual and in need of a break, Lindsay’s blush darkened as she slid from the bed to her knees, bent forward, and put her hands on the carpet. She felt the constant friction that the cuffs offered, but relaxed, and went docile. “I’m ready, Daddy.”
“Oh, you’re my good girl. Such a good girl.” Sammy’s voice was full of praise as he led his obedient, faithful pet to the adjacent bathroom. “I think I may have an eight-inch snack for you.”
Little did she know, however, but Lindsay had a rather ominous e-mail waiting. Once she and Sammy emerged from their “sexy time” and he permitted her the opportunity to check her phone, Lindsay would be in for quite a shock.
From: Bancroft, Evelyn
To: Anastacio, Lindsay
Sent: December 18, 2018, 8:58am HST
Subject: My best friend
Lindsay –
I quit the brothel last night and am back in Citronelle. I couldn’t stand things there and feel like a failure. The constant sex with strangers, the ridicule from other girls, the demand to always look perfect, to be perfect. I just couldn’t deal with it. I know I let you down. My mind is in a bad, bad place right now too. I learned today that Clancy and Zack saw my photos on Happy Ending Ranch’s website and informed my parents that I’d become a brothel whore. Needless to say, they didn’t take the news well. I was kicked out of my house, told never to come back, and am typing this from the fairgrounds. It’s so cold out and I feel so lonely.
I know that you and I have gone through a hell of a lot together, but I cannot take this meaningless existence anymore. I’ve been a constant disappointment and that trend is bound to continue. I’m going to end this hurt for good.
I love you more than you could ever imagine, however I can’t keep bothering you with my crap.
You will be okay. You have Mike and friends like Pamela and Mariko to get you through, and everyone will forget about me pretty fast anyway.
I wish I could’ve kept working at the brothel and built the life you wanted me to have, but I failed, and Mom, Dad, my brother, all hate me now.
I’m sorry I couldn’t be stronger like you. I’m sorry I couldn’t make you proud. Just know, this isn’t your fault as you’re the only family I have left and I will always love you so, so much.
-Evie
(End of Chapter Seventeen – to be continued)
