The Girlfriend Experience Ch. 29

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Man pays to have sex with his old high school crush.
10.6k words
4.61
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Part 29 of the 35 part series

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

Chapter Twenty-Nine

Holy kamoly.

Donald Stanlick lifted his gaze and met Lindsay Anastacio's eyes as they crinkled at the corners.

"Welcome to my humble abode." She motioned toward the all-pink bedroom before shifting her focus to Donald's paunchy arms crossed tight against his chest at the entryway. "Why don't we go over to the bed, sit down, and make ourselves comfortable?"

Nineteen-year-old Donald's heartbeat was on overload and his body thrummed with energy at the reality unfolding around him. Christ and heavens almighty. Close up Lindsay was intoxicating, with a face framed by the silkiest blonde hair he'd ever seen, a mixture of sunshine and honey contrasting with strands of shimmering golden highlights. For as long as he could remember, it had been this face that dominated his imagination when he was alone at night, her voice whispering sweet nothings into his ear. It was those vermillion-red lips and the recollections of Lindsay's unrivaled beauty that made Donald so excited he couldn't help but self-satisfy the primal urges she'd stirred within him since their childhood years.

He tried to speak, but the scent of Lindsay's wildflower perfume invaded his senses yet again, sending his libido orbiting into the stratosphere, and his tongue became stuck to the roof of his mouth. His eyes raked down her body, noting she'd worn her old Citronelle Blackhawks school hoodie (per his request) over a clingy white V-neck shirt. Just like the old days. She had a wisp of a figure, a brilliant tan, and breasts larger than his memory served, not to mention greatly exaggerated for a girl of her slim stature. But I ain't complaining.

Lindsay reached out a tiny hand and extracted one wrist from his chest, projecting a smile that made the tendons in his neck stand out. Blue eyes lingered on his white polo shirt, or more specifically, the pocket protector stuffed in its front pocket, then rose to his again. "Why are you so tense? You need to loosen up."

"Umm, I..." The young man swept a shaky hand over his brow and his cheeks flushed a crimson red.

"Come on, sweetie. Don't be shy." Lindsay's voice was mellow as she flipped her long hair across her shoulder. "Come over to the bed and sit down with me, okay? I promise I won't bite."

Donald took stock of the room's interior and his jaw dropped. Was he dreaming? How could this be? This girl is the gold standard - always has been, always will be. How lucky was he to be in Lindsay's bedroom? How many guys could make such a claim? Oh, wait... never mind.

No, after reconsidering, it wasn't a bedroom - it was an oasis, her private retreat.

The aroma of burning incense - fresh flowers and herbs - filled his nostrils. Neon lights and images from a galaxy projector decorated the ceiling and walls, their vibrant colors livening up the mood and creating a warm, inviting atmosphere. Tapestry quilts lay across the rocking chair and the bed itself. Two wicker chairs were on one side while an endless array of shoes lined the other, assembled by the height of their heels. Oh lordy. I am dreaming again, no doubt. The sight of black vinyl boots which must've been thigh-high brought an itch to Donald's scruffy chin. A dresser drawer was somewhat open, too, hinting at satin and lace - sexy lingerie - hidden within.

Donald sucked in sharp breaths as he glanced around, cataloging every inch. Maybe she can wear some of those frilly things tonight and offer me a fashion show. Lindsay was in no rush, providing him time to explore, and enjoyed observing him take in every detail.

Donald envisioned his ultimate crush curled up in the rocking chair at night, wearing a bathrobe, texting her friends for hours on end. God Himself couldn't pry that phone out of her hand back in high school. Speaking of school, was she attending college now? How could someone work in a place like this and go to college at the same time? And what had become of Lindsay's life since the tragedy in Citronelle eleven months ago? Is she still dating that old millionaire from Utah? Michael... whatshisname? All her dirty laundry had been aired out in the local media. I couldn't stand the way they portrayed her, how they destroyed her reputation. It seemed unfair because he knew Lindsay and Evie were the best of friends. She never would've done anything to hurt her on purpose.

"Are you... are you s-s-sure... you don't mind if I call you... L-L-Lindsay?" Donald was so on edge that it was a massive struggle to force those words out. Stuttering and butchering the English language around girls had been an issue all his life. "I'll... I'll call you Kayleigh if... if you want me to." But this wasn't just any girl.

No, this was the girl.

An hour ago, things started in a similar fashion once Lindsay emerged and greeted Donald with open arms in the parlor, hugging him as if that hug had always been inside of her, waiting to come out. I wish she acted that way toward me when we were younger. Of all the reactions he could have predicted from her once she saw him, that was the least likely. I feared she may laugh and thumb her nose at me. Donald was anxious, scared, and intimidated to the point where he experienced a paralyzing hesitation, with bumbling, half-coherent answers. It took time, but Lindsay was able to soothe his nerves.

Yet now, being in her bedroom - of all places - it was back to square one.

"Don't be silly. You don't have to do that." Lindsay shook her head in a swift arc and perfect teeth shone through her grin. "Kayleigh is my working name, but since you and I know each other, you can call me Lindsay as long as we're alone together in this room. We're friends, right? We've known each other forever." Thin, supple fingers wrapped around his hand as they moved toward the bed. "But remember what Colt said, okay? The bartender? You must call me Kayleigh anywhere else in the house."

"Okay." Curse those butterflies in his stomach!

"Us girls here value our privacy, our anonymity."

"Yeah, I understand." We're friends? Donald wondered during the drive to Flagstone if she would remember him. Let alone know who I am to begin with. Growing up, he could never summon the courage to approach her and introduce himself. Looking at Lindsay, admiring her from afar each day hurt. It physically hurt because he realized they could never be together.

So, why couldn't Donald tell Lindsay how he felt? Zack would've kicked my ass if I said anything to her. She was the unattainable ideal, sashaying into class every morning in her yoga pants and baby tees with an armful of spiral notebooks. Every eye was drawn to her, like metal to a magnet, male and female alike. But she would put the notebooks down and take a seat, oblivious to the attention.

What exactly did she see in Zack? Was it a case of this so-called "bad boy" oozing confidence with his don't-care, risk-taking attitude that appealed to Lindsay? Sorry, but I'm not a dick, nor will I ever be. Zack would strut into any room as if he owned it. He was narcissistic, obnoxious, impulsive, and cheated on her multiple times. Doesn't she want someone who would be faithful? Someone who would treat her right and love her without question? Donald was Lindsay's savior in his ongoing fantasies, rescuing her from the muscle-bound, dastardly jock. We'd run off on fun adventures every single night and marry each other.

Last December, rumors quickly became town gospel - The Citronelle Courier cited numerous sources that Evie, before her demise, made her living in this brothel and was "coerced" into the industry by Lindsay, whom they also reported was a prostitute.

Donald immediately registered on Happy Ending Ranch's website and scoured its bulletin board for reviews of "Kayleigh" (who at the time was retired (and with Sammy)). Zack posted on social media that Lindsay's working name was Kayleigh there and, judging from the comments, she was a popular attraction. That's no surprise. It took two days, but once Donald was able to find an archived copy of her biography page via the Wayback Machine website, he was on cloud nine. How many guys can say they have nude pics of their high school crush all grown up, a crush who never even knew they existed?

"So, I'm flattered you drove all the way from Citronelle to see me. And in this snow too." Lindsay settled beside Donald on the bed and wrapped her arms around him for a quick-hitting embrace. His spine went stiff as plywood and yet another lump formed within his throat. "Whoa, hey there, Donnie. Settle down, okay? Relax."

Donnie? "I... I had no idea it was supposed to snow." If he were alone, Donald would proceed with his standard route - he would gather the nearest pillow, cover his lap, and jerk off. 'Ol reliable, right? The only sexual comfort he'd ever known in life? Sweet mother of God, this girl had always done funny things to him. But Donald wasn't alone, of course, yet he still had the urge to self-satisfy. Snap out of it, man!

He drew in another deep breath... of her. "I, uhh, the snow only started about fifty miles south of Flagstone, and uhh, and since I'd come that far, I was... determined to make it the rest of the way."

"You..." Lindsay inclined her head and offered a strained smile, "... don't get out much, do you?" She eyed his crouched posture and the way his hands trembled at his belly. "Don't take that the wrong way, Donnie. There is nothing wrong with being shy, being introverted. But the one thing I remember most about you back in school was you read books... a lot. Like, all the time. Why?"

"Umm, just wanted straight-As and stuff." He fiddled with his shirt collar. Would you fuck me? Because I'd fuck you. Donald's mind replayed an explicit fantasy, perhaps his most recurring one, where Lindsay would approach him in her cheerleading uniform after yet another heated argument with Zack. From the moment I first saw you, you made my pussy so wet. I need you. Forget my loser boyfriend; I'm going to fuck you tonight.

Back in the real world, Lindsay's visage brimmed with warmth. "Relax. Relax, okay? Give me your hand again. Come on, give it to me." She exhaled and hair rustled across her forehead. "See, that's not so hard, is it?" Her smile blossomed. "So, you came here today for a reason, right? To see me, yes? Can you tell me exactly what it is you want from me?"

Instead of answering, Donald rubbed his face with both hands and when he dropped them back onto his lap with a thud, his hair was sticking up where he had ruffled it and his eyelids slammed shut.

"It's okay, baby." Lindsay flattened down a tuft of his hair, her voice a whisper, and latched on to his right hand again. "There's no need to be nervous. Take a deep breath and settle down, will you? There. Breathe, baby. Yeah, that's better. Much better."

Silence reigned between them until Lindsay was the one who broke it. "Lots of people come to brothels, you know. All kinds of people, many of whom are lonely, and need a pick-me-up. Older, younger, all types. Men, even women too. There's nothing wrong with it. Nothing wrong at all.

"In a brothel, you can escape your troubles and experience life on your own terms, your own way. I'm not going to judge you, Donnie. I won't condemn you, either, nor would I ever tell a soul back in Citronelle you came here. That's not my style - not how I do things, or how brothels operate, especially this one. Whatever happens will be discreet and only between you and me. There is no reason to be scared, okay? I want to help you. I'm here to help you." She eased nearer and gentle, seductive lips brushed his ear, reverberating deep into his soul. "So, what can I do to make this experience one you'll never forget? I want to make you happy."

Marry me. "I..." A cold shaft of fear assailed him, so intense that he again slumped downward. You're a loser. The words Donald's father told him before his junior year, in a fit of anger, rang through his mind. Always have been a loser, always will be a loser.

Fingertips massaged his neck. "Talk to me, Donnie. I can't help you unless you tell me what you want." She cupped his chin and angled it up toward her, deep blue eyes holding him captive. "Do you want to have sex with me? Is that what you want?" Lindsay stroked her thumb across his lower lip. "Do you want to fuck me, Donnie?"

"Yes," he said, surprised at the seriousness in his voice. "Yes, I do."

"Okay, then. All right." Lindsay's cheeks turned a light shade of red. "Progress. Now we're getting somewhere."

* * *

"This dude is a virgin if I ever saw one." Colt rubbed the spot above his eyes where a headache was forming. "It's as clear as day."

"You're not a fan of Lindsay doing this. I get it." Pamela stood across from Colt as they monitored the negotiating session via the surveillance system in their office. "Too many complications could arise with Donald knowing her, especially if he goes back to Citronelle and blabs about his experience to the whole town. But she's a grown adult and wants to do this. It's her decision."

"What if two, three, four, or five people suddenly show up from Citronelle and want to party with Lindsay? Or more?" Colt sighed. "That would be awesome for business, I suppose, but there'd be no discretion for her, no privacy. Lindsay doesn't need to be reminded of her old life and for the people in Citronelle to make more wild, unfair assumptions about her.

"What I ultimately want, you know, is for Lindsay to reconcile with her family, but this could impact that possibility, perhaps even destroy it. I don't know; I don't relish the income potential the way I used to." His foot dribbled the floor like a basketball. "Maybe I should just retire and become a zookeeper."

Pamela shot him a curious glance. "Random. But okay."

"I streamed a show on Animal Planet this morning."

She smirked and perched herself on the desk. "You love Lindsay the same way I do. I understand, Colt. I really do. You're concerned with this guy showing up to party with her. Donald told you even though it's been well over a year since he last saw Lindsay, he still goes to bed every single night and falls asleep fantasizing about her."

"That's not normal." Colt blew out a breath. "In fact, it's downright creepy. Maybe even obsessive."

"This is a brothel." Pamela's shoulders flinched. "We deal in the creepy, don't we? The obsessive too. I'm sure there are a ton of guys who fantasize about me every night as well."

Colt couldn't camouflage the storm raging in his eyes.

"Don't second-guess Lindsay or overthink this, okay? The fact you have a heart and you're not concerned with making maximum money is a secret that's safe with me. I promise not to tell the other girls."

"Gee, thanks."

"And I'm overjoyed with the way you and Lindsay have gotten closer since the summertime, the way your relationship with her has grown. You've been killing yourself for so long with this place, Colt, worried so much about reducing turnover and improving our profit margin." Pamela reached for her coffee and a smile tugged at her lips. "I've enjoyed watching you and Lindsay evolve and take shape as a couple."

Colt inclined his head. "What's with that look?"

"What look?"

"The smirk. The same smirk you always give me when you're hiding something but refuse to say what it is."

She passed him another glance. "Stop being silly. I was in love with Lindsay from the start, and I'm just happy you finally smartened up and allowed her into our lives because she's such an awesome girl."

"She is an awesome girl. I cannot argue with that." Slowly, Colt rose to his feet and proceeded to the window with both hands clasped behind his back. "But I have a bad feeling about this party."

* * *

"Yeah." Donald's eyes misted up. "Yeah, I am."

"Wow, I'm so honored to be your first." Lindsay couldn't help but grin at the reality unfolding around her as well. Despite servicing 152 clients over the past sixteen months, she had yet to be with a virgin. To pop a cherry! This was something she'd been looking forward to for quite some time too. And Donald wasn't a forty-year-old either. No, he was her age and, even better, Lindsay had a history with him. "Don't you worry, I will take perfect care of you." Knowing him would make things cumbersome, for sure, but at the end of the day it was a job, and Lindsay planned on treating Donald the same as any other client. I want him to look back fifty years from now and say being with me was the best sex he's ever had. "So, what are you into?" Then again, this may be the only sex he ever has. "What gets you off, baby?"

"Well, uhh, passion."

Lindsay moaned and her eyebrows wagged.

"I don't know. Maybe we could, umm, try some of the stuff we talked about earlier, the things I fantasized about. And maybe you could wear something... s-s-sexy for me. I've read all your reviews on the website, and... you know, I'm really excited. I'm sorry, but I'm a little stumbling over myself right now."

"Hey, that's okay." Damn, he loved the sound of her voice. "It just means you're going to enjoy it."

"Uhh, yeah. I will. I know I will." Hell, just the sound of her breathing too.

"You will, trust me. So, is there anything else you want this evening?" Lindsay tilted her chin upward, exposing her neck. "What are your priorities, your needs? Your desires?"

Sweat erupted on Donald's forehead and he shuddered, gripping the blanket in hopes of stabilizing his emotions. "I've waited for this moment for a long, long time, but I'm not into anything crazy. Just a standard treatment."

"Okay."

"Whatever you think is nice."

"So, you want a Girlfriend Experience, huh?" She pinned him with a feral gaze. "You want the Kayleigh slash Lindsay Experience? Lots of people do. It's my most common party request." She glided her fingers up and down his back. "Hugging and kissing? Oral both ways? Sex in different positions? Lots of cuddling?"

"Yeah." He bit his lip.

"And you have a thousand-dollar budget, am I right?" Considering this was Donald's first time in a brothel (and his massive crush on her), Lindsay could fleece him if she wanted to. He's not going to say "no" to any time frame I offer him. Did Lindsay have it in her to claim Donald's money would only be enough for a ninety-minute party? Or would she play dirty - lowball him - and say her rate was a thousand bucks for sixty minutes? Scarlett and Mariko wouldn't have a hint of remorse. They'd rob this kid blind.

"I'm willing to do a two-hour GFE for a thousand dollars."

"Two hours?" A smile parted Donald's lips. "Are you serious? That's more than I..."

"Yeah, two hours, but no more." Lindsay couldn't jack her rates up like the others. Donald is a virgin and I want to take things slow and let him enjoy himself. Younger guys always pay the house minimum with me. Most of all, Lindsay wanted the experience to be monumentally epic, one he would always hold dear. If he's truly been in love with me forever, I don't need to be stealing his life's savings to shave off twenty, thirty, or sixty minutes. I may be a whore, but I'm not a greedy whore. Besides, with this snowstorm, the house wasn't brimming with customers. Being with Donald will keep me busy until nine or ten o'clock tonight.

Jeremydcp
Jeremydcp
1,101 Followers