The Girlfriend Experience Ch. 14

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58-year-old man pays for an 18-year-old prostitute.
25.4k words
4.66
13.7k
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Part 14 of the 35 part series

Updated 03/03/2024
Created 06/03/2023
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Jeremydcp
Jeremydcp
1,101 Followers

Chapter Fourteen

Sammy maneuvered Lindsay through the bedroom until the back of her knees touched the mattress before lifting and tossing her on it like a sack of potatoes. From where she now lay plastered, Lindsay looked up, shivers traversing her spine as Sammy removed his tie and loosened his collar. The eighteen-year-old hitched her breath, brought a hand to her chest, and measured her escalating heartbeat. Sammy was so handsome, and so experienced, his trimmed beard emphasizing his dark, demanding eyes, full of hunger, and undeniable purpose. The blue suit and classic cut Oxford shirt added to a timeless alpha appeal brimming with wisdom, assertiveness, and brash attitude.

Sammy borrowed a moment, appraising Lindsay as if she were a commodity to be auctioned off and sold to the highest bidder fortunate enough to procure her long-term services. "My Kayleigh. My submissive bed girl, my babygirl, my fuckdoll whenever I want."

Lindsay saw it in her mind - memories from last week - Sammy's hands seizing control of her hair, the bump and thrust and unbelievable friction of his cock moving inside her mouth. With her head tipped over the perimeter of the bed, she was helpless, pinned in place, his heavy balls swinging near her eyes as he fucked with ruthless aggression. Her hips squirmed with every plunge, and she was again reminded of his strength and her vulnerability. Oh, dear God; he's going to totally slay me again tonight. The hand on Lindsay's chest, without preamble, drifted toward her abdomen.

"You're my little whore, aren't you?" Sammy's tone was soft but laced with the promise of consequences. "Such a marvelous toy. One thing both you and I know, Kayleigh, is that you need a bona fide fucking. You need it very, very badly. And tonight, I promise to give you what you need."

"Yes, Sammy. Oh God, yes. I want you to fuck me." Lindsay's gaze didn't waver from his face, either, as her hand finished its journey, her fingers raising the hem of her prom dress and finding the gusset of her G-string panties, applying pressure where she needed it most.

"So naughty," Sammy said as Lindsay's fingers busied themselves between her thighs. "You are such a nasty, horny slut, Kayleigh. So ready to be fucked."

Lindsay's mouth dropped open and her opposite hand came up on its own to cover it. A nasty, horny slut? Was she really this type of girl? Her brow crinkled. Did her parents raise her to lay beneath a man forty years her senior with her legs spread and pleasure herself in plain sight? Face it - you're good for one thing, and one thing only, so you might as well get paid for it. Sammy would fuck her tonight, he'd possess her, and enjoy her on his own terms - for an exorbitant fee.

At what point did Lindsay veer from the proper path?

"Open your pussy lips, will you? Nice and wide. Yes, yes. Look at that pink, little pussy. You're dripping wet already."

Happy Ending Ranch had changed Lindsay. She had become suitable for sport fucking in a short amount of time but would be far more suitable with additional on-the-job training. Men like Sammy, Ryker, Darius, Tony, and all the others, for the most part, got their rocks off being with her.

God, this girl loved sex. Lindsay loved huge dicks and masculine hands. She loved wearing lingerie and men who would rip it off and chuck it across the room before bending her over the desk and sticking their cocks in her. Lindsay was accustomed to being ridden hard and allowed these mongers to control her body, to take ownership, so they could fuck as they pleased, fearful that if she didn't satisfy them, she'd lose her job.

Out of the corner of her eye, because she couldn't help but to look, Lindsay noticed it in the floor-to-ceiling mirror: her submissive posture and the contrast of her lacey black prom dress and Sammy's business suit, the difference between a wealthy, dominant older man and a fresh-faced girl just removed from her high school graduation beneath him, on her back, ready to serve his wicked pleasures.

It was as if Sammy had cast some strange spell on her. What was his secret, anyway? This terrible need for degradation kept evolving, kept multiplying. The desire to allow random men - mongers, and women like Becky, too - to use her. What happened? You used to go to church twice a week with your family.

"Raise your knees and take them into your hands," Ryker said to Lindsay this past Saturday morning, and like a dutiful service provider, she complied. "Very nice, sweetheart. Such a pretty cunt you have, a perfect cunt." Ryker took hold of her hips, saying, "Keep those legs open," and brought her toward him, to the edge of the bed, so he could immerse himself in her wetness.

"Hmm," he said. "A tight cunt too. I wish I could trade my wife in for you and take you home. I'd love to parade you about, show you off to all my friends and make them jealous. Maybe share you with them too." Ryker gripped her upper thighs and Lindsay cried out as he pounded away, slapping his pelvis against her prone ass so hard that the brass headboard bounced and crashed against the wall.

He fucked Lindsay for several minutes as her eyes alternated from his face to the spectacle of his cock claiming her pussy again and again.

"Oh, yes! Just like that. Fucking pussy is amazing! Fucking pussy is amazing! Only thing better than your pussy is your face!" The shame was exquisite - this total stranger, having sex with her in exchange for money, interested in her body, her physical charms, and absolutely nothing else.

Mom and Dad wouldn't be proud.

Back in the present moment with Sammy, Lindsay's face puckered, but soon her fingers slipped under the elastic and found the silken crease of her pussy, which she had given a fresh shave to Tuesday in compliance with Riley's "recommendation." Riley said I'll make more money this way. Her pussy was soaked and ached already, and thus, Lindsay came to the realization that yes, indeed, she was definitely that kind of girl.

A nasty, horny slut.

Sammy's blazer came off, followed by his dress shirt, revealing a hairy, muscular chest. Lindsay's galaxy-blue eyes were staring up at him, as big as saucers, and Sammy sprung a grin. "You and I are a perfect match, Kay-Kay, a true connection. We're gonna have lots of fun."

When Sammy lowered himself over her, Lindsay pushed up and trailed her fingertips down his bare back, enjoying the texture of his weathered flesh.

"Ahh, that's my sweet girl." The two unrighteous lovers were moving together already, legs intertwined, foregoing the required negotiating process and getting right to the hot stuff. "Those tits feel so good in my hands."

Lindsay was ready to throw caution to the wind and lose herself in this perfect moment. She kissed Sammy's jawline and reveled in his well-groomed beard bristling against her cheek. Her legs coiled around his hips. Driven by need, she was amazed at how her body responded to Sammy, easily the sexiest man she had ever met. The big, bad wolf - the leader of the pack.

"You know what to call me, Kayleigh, honey," he said in that same stern voice.

Lindsay gasped and hearkened back to their first date and all the ensuing e-mails they had shared since and whispered the one word he wanted to hear. "Daddy?"

"That's right." He moved his hand from her waist to between her thighs and she gave a cry at the sudden rush of stimulation. "How is this pussy doing?"

"Fine, Daddy." Lindsay arched her torso, thrusting her pelvis against his hand, needing more. Sammy glared at the bare furrow of her sex, satisfaction in his gaze, and she tried to ride that hand. "Fuck, Daddy. Fuck!"

"Have you been keeping your cunt full in my absence? Earning lots of money like a true whore should?"

"Yes, Daddy." Lindsay blushed a fiery red and hid her face in the sanctity of his beard. His presence alone wiped away any feelings of modesty, of independence, and of course defiance. "I'm ready to be a good girl and do what you tell me like we've discussed." Break me, Daddy. I'm begging you. Break me.

"That pleases me and I'm glad to hear it." Sammy fondled Lindsay as he spoke, and her hips jerked at the invasive rhythm of his fingers. "You're gonna be a good girl tonight, my submissive bed girl, who belongs to me because I'm going to pay a ridiculous amount of money for you." He took his hand away, but then brought it to her face with a pair of extended fingers. "Look, babygirl. Look how wet you are."

Lindsay whimpered, but also remembered that if she didn't follow protocol, Jim may start pounding on the door at any second or, even worse, burst through and put an end to their fun before it began.

"Open up, Kayleigh," Sammy said, taking precedence over her fears. "Open up and taste yourself."

Lindsay closed her eyes and took his mammoth fingers into her mouth because it would anger him if she didn't. I don't want to get spanked already. Or do I? The young prostitute suckled away, licking her juices as if his digits were ice cream cones. Sammy's smile widened as his index and middle fingers moved in and out, using a similar cadence to how his cock would put her pussy through the wringer in due time.

"What are you looking for tonight, Daddy?" she asked. "What can I do to make you happy?" Since this was a brothel, any legitimate intimacy wasn't supposed to start until they waded through the formalities of the bartering process and agreed on a price. I'm glad Colt isn't here. He would already be in here and threatening to fire me since I gave Sammy a freebie. Afterward, Sammy would have to pay for any services before they were rendered. No matter how close they had gotten in recent times, the proper procedure still had to be followed. I'm also glad Jim is so chill and is allowing us to bend the rules a little.

Still, Lindsay wasn't about to push her luck too far.

After the initial shock of finding Sammy in the parlor earlier, she spent thirty minutes reminiscing with him about their evening together from last week. Since Jim was also present, conversation was kept light and general.

Thus, Sammy didn't dare call her "Lindsay" - her name was "Kayleigh" tonight. Being a turnout, Lindsay would lose her job if Colt caught wind of all the sensitive information she had given him. Real name, private e-mail, cell phone number, and her mailing address back in Citronelle. Plus, they had plans to meet up eleven days from now in Utah. There was no mention of that either.

Colt wouldn't tolerate any employee going into business on her own, fearful the local authorities, particularly the Sulaco County sheriff, would find out and revoke his business license because of it.

"I know I promised to come back to the ranch and party with you again in September," Sammy said to Lindsay as Jim tidied up behind the counter, "but I couldn't wait. Last time was too much fun." He winked an eye and grinned mischievously. "Rest assured, though, I still want to see you in September too."

In the bedroom, Sammy's hands slid up Lindsay's legs and underneath the hem of her skirt, past her ass, and came to rest on her waist. He held on as she initiated another slow rhythm and ground her hips across his pelvis. The friction made him tighten his grip.

Please, please, please, get three or four hours with me, Daddy. Sammy showing up unannounced like this was a wonderful surprise and Lindsay wanted to enjoy herself without having to keep an eye on the clock. She dry-humped his dick through his slacks. He now had one hand on the waistband of her G-string and the other clutching a breast through the fabric of her dress.

"Tell you what, darlin'. Here's what I want." First, Sammy captured her mouth in a deep, soul-crushing kiss, reminding her that between the two of them, he would always be the one in charge. The fire in Lindsay's loins burned hotter. Their tongues met in a frenzy. Sammy explored her teeth, the roof of her mouth, the hollow of her cheek. She again thrust her hips upward, wanting more, but he used both hands to keep her in place this time. "I'd like to purchase twenty-four hours with you."

Her eyes bulged. What the ...?

"A full day." Sammy used his right hand to brush a lock of long hair away from her face. "I'm offering you eighteen thousand dollars if you'll give me the honor of spending the next twenty-four hours with you, sweet Kayleigh." The pulse point on her neck jumped, but Sammy was right there to kiss it and soothe the anxiety away. "From right now - six-thirty tonight until six-thirty tomorrow night, or whatever. Whenever we start - twenty-four hours." Lindsay worked her tongue over concrete lips as he said, "I'll pay for it in cash. You can do the math on your smartphone if you want, sweetheart, but that's seven hundred and fifty dollars an hour, and I never pay more than six hundred here, at least for a one-on-one party."

"No, no, it's not that. I trust you." Lindsay blinked several times to process the generous offer. Twenty-four hours? She was with Sammy for a measly three hours last week and still wasn't convinced her body had recovered from the hardcore fucking he gave her. Sure, she had been passing lots of jokes the past couple of days about wearing him out, but how could she last twenty-four hours with a man this experienced? This skilled, this dominant? He'll be fucking me nonstop!

"I'm offering you a higher hourly premium because at certain points, I'd like to invite other girls to join us and make it a threesome or a foursome. I'll pay them separate rates. C'mon, say yes. It'll be fun." Lindsay enjoyed licking pussy and had yet to sample all the other whores throughout the house, but that would change tonight and tomorrow.

She would fuck every single one of them - while Sammy watched.

And join in, too, of course.

Twenty-four hours!

Lindsay wanted to rekindle their magic from a week ago, but what was too much? Was there a limit? Again, Pamela's words of wisdom popped into her mind. Never agree to do anything with a client if it's outside your comfort zone.

Another voice in Lindsay's brain disagreed.

Think of the money you'll make! More than that, she languished in bed every night hot, needy, and bothered, and when she fell asleep, often dreamed about Sammy. He's here now and I'm back where I belong - with him. How could Lindsay allow this opportunity to slip away?

"We could spend two or three hours alone together, then invite Elisabeth in, and I'll make an offer for her to join us for an hour. A short time later, after Elisabeth leaves, we'll invite Mariko in, and she can party with us for an hour too." Sammy backed away. "Doesn't have to be any specific order. Sahara, Riley, Kenzie, Nicolette, we'll cycle through them all." Sammy's chin tightened. "It's too bad Pamela is out of town. I know you and her are close and I was looking forward to partying with her again too. Haven't done so since Christmas."

Aware from his ongoing correspondences with Lindsay that Pamela was injured, Sammy still expected her to be here, and his original plan was to offer Lindsay and Pamela $20,000 apiece for a twenty-four-hour threesome. As the part-owner, there was no way Pamela would turn down such a payday, bad back or not, and Lindsay, well, no way she would either. These were his two favorite girls in LPIN, bar none, and he considered Colt to be a lucky bastard to be married to such a fine woman.

But since Pamela wasn't here, Sammy had some ideas that would make his party with Lindsay all the more memorable. Involving all the other girls, yes, but something far, far kinkier. With any luck, he'd be able to make it happen once Jim's shift ended at nine o'clock and Mindy was running the house for the remainder of the evening. Sammy had struck a handful of hush-hush deals with Mindy in the past and didn't anticipate any resistance.

$18,000 was a lot of money. In all honesty, Sammy believed he was owed a discount by asking for twenty-four hours. The max, he thought, should be $12,000. But since it was Lindsay, he didn't mind. He wanted her to have the money. To him, Lindsay would deserve it, she'd earn it, especially after involving the other girls and pushing her limits into the stratosphere tonight and tomorrow.

"Babygirl, talk to me. Why are you crying?"

"That's going to cost you a fortune." Lindsay pressed a palm across her lips to help stifle her emotions. "Sammy, Daddy, I don't ... I don't ..." Want you to blow all your money on me. Lindsay wanted to get paid like any working girl, of course, but wasn't greedy and uncaring like the overwhelming majority. I love you, Sammy! She didn't want to create any sort of financial burden for him (or his family) either.

A lone tear streaked down her cheek, but she was quick to wipe it away. Beyond the money thing, I'm fine being with you for twenty-four hours. I'm a big girl and can handle it - I hope? - if you can. But she didn't want to eradicate his savings. You're a good man and I don't want to cause you any trouble.

"Don't worry about it." Sammy understood the issue. Lindsay's body twitched against his as if she were a toddler needing encouragement. "The money is a drop in the bucket to me, sweetheart." Sammy had already told Lindsay multiple times that he was the CEO of Gradiph Pharmaceuticals and made over $37,000,000 last year alone, with a net worth four times that amount. He hadn't worried about his finances in decades.

Was there another prostitute on the face of the planet who'd balk at accepting $18,000 like this? Scarlett would be falling over herself if she were here, Sammy thought, and already have him balls-deep in her mouth.

Without a condom.

Yet, Lindsay was worried about bleeding him dry. Indeed, this girl was rare. A genuine, kind, selfless whore. So extraordinary. Sammy needed to snatch Lindsay up and make her his private property before the industry warped and corrupted her like it had so many others.

His reason for showing up tonight was simple: Sammy couldn't wait another eleven days to have sex with Lindsay again. No way, no how. He worked a half-day this morning and told his wife he had to travel to Chicago for a business meeting and wouldn't be home until after midnight tomorrow evening. Sammy had no choice - he flat-out lied to Barbara this time, fearing she may obliterate him if she knew he planned on being at the brothel for twenty-four hours (thus, his insistence on paying with cash instead of credit). And though he wouldn't get the threesome with Lindsay and Pamela he wanted, Sammy figured he'd wind up spending over $40,000 here anyway.

Aside from including all the other girls, Lindsay would deserve a generous tip, right?

"I'm going to take care of you and treat you the way you need to be treated, Kayleigh. Please, agree. Let me do this for you." Sammy tried to hide a sly, wicked grin, but failed. He had visions of some introductory BDSM play and a host of spankings. She had begged for it in her e-mails, through texts, and tonight, tomorrow, she was going to get it. Daddy is finally home, Sammy said to himself, and he's none too happy his little princess has been fucking the entire school, including the teachers and the janitor!

"I'll have Jim or Mindy, or whomever, deliver us food from any restaurant in Flagstone you want whenever you're hungry. Give me the word, darlin', and it's yours. I'll pay for it." Sammy kissed her harder this time - so hard that for a moment she struggled against the suddenness of it, and that gave him a jolt of arousal. "We'll stop and take breaks whenever you want. We can get a full seven or eight hours of sleep too." He kissed her again. "I want to fall asleep with you in my arms and wake up in the morning to your sweet, sexy face." Perhaps with his cum caked all over it too? "It would be a dream come true." And then he'd fuck her again. Maybe with his dick plowing into her from behind. I love waking up whores by giving them a hard fucking.

Jeremydcp
Jeremydcp
1,101 Followers
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