KK's Quickies: Conquering Quarterback to Truck Stop Temptress (1/1)

Over the past couple years, for no reason that would be immediately apparent to an outsider, one particular gas station, situated on the loneliest stretch of highway passing through Texas, had become the most popular long-haul truck-stop in the country. Despite the filthy bathrooms, unfriendly service, and oftentimes broken-down pumps, lonely truckers prayed for the day their route would give them an excuse to stop by.

The motivating factor for this mysterious popularity could be found in the back lot of the gas station, in the form of a little beat-up trailer, unremarkable except for the fact that a makeshift clothesline, stretching from end to end, was generally hung with a dizzying variety of frilly lingerie, skimpy tops, tight dresses, and barely decent miniskirts, all in a range of bright, garish colors. Of course, it was not the trailer itself that brought truckers to the station in droves, but rather, the working girl who lived there.

“Debby Darling,” as she had come to be known, had set up shop a couple years back, and word had spread quickly that she was well worth the money: the pretty young transsexual was an absolute goddess by truck-stop standards, and not only that, she was enthusiastic to a fault. No sooner could you pull into the lot than Debby would come rushing out of her little trailer to greet you…and after a long, lonely cross-country drive, she was truly a sight for sore eyes.

Yes, nature had cursed Debby with broad shoulders, large hands, and impressive height. But it was clear she had done her very best to mitigate all of those disadvantages, likely going into debt to do so. The results of her many cosmetic surgeries were stunning: she was equipped with an enormous, gorgeous rack (clearly filled with silicone, but no less sexy for it), an incredibly tiny waist (liposuction and rib removal), and a curvy, jiggly, heart-shaped ass (the best butt implants money could buy).

Her face was still slightly on the masculine side, thanks to a wide brow and strong jaw that most male models would, ironically, have been quite jealous of. But her makeup skills were second only to her blowjob skills, and she knew exactly how to soften her harshest features. With her expert contouring and blending, plus perfectly microbladed brows, thick and fluttery black eyelash extensions, and massive, puffy, filler-plumped lips, she managed to look strikingly beautiful even in broad daylight.

Whereas most other truck-stop hookers had long since given up on looking their best for a bunch of smelly long-haul drivers, the twenty-something Debby absolutely obsessed over her appearance. Every few days she would beg a ride to the big city, and come back loaded down with facial masks, skin creams, haircare supplies, teeth-whitening strips, home waxing kits, nail kits, and everything else she needed to look her sexiest, girliest best at all times. She even took care of her body, too – one of the truckers’ favorite early morning activities, if they happened to be awake, was watching Debby bounce and flounce along to a work-out video on a little old TV she’d set up on a lawn chair outside her trailer.

The total sum of all her hard work was spectacular. Every time Debby came swishing out of her trailer on her sky-high stiletto heels, hips grinding out a sexy, whiplash-inducing strut, big boobs jiggling merrily inside the skimpy confines of whatever low-cut top she’d found to display them in, long peroxide-blonde hair bouncing around her perfectly made-up face, hearts stopped. Best of all, she did it with a sunny white smile that never once faltered.

“Hi, boys!” she would squeal, in a breathy, high-pitched falsetto that was clearly the poor thing’s best effort at the female register. “Who’s first today?”

Which would in turn, of course, immediately trigger a brief but intense competition to be that oh-so-lucky first guy. Debby would just smile vacantly while the truckers debated amongst themselves, standing with one hip cocked, often twirling a lock of long blonde hair around her glittery, claw-like fingernail. She was patient to a fault, and though most of the guys showered first out of courtesy, she didn’t even seem to mind it when they came straight to her stinking like a non-stop cross-country journey.

Furthermore, she seemed utterly oblivious to the fact that with her looks, it would be a snap to find some wealthy sugar daddy to take care of her, and probably pay off every single one of her debts…at least, they assumed she had debts, because why else would she be hooking at a truck-stop? And why else, after every satisfied customer, would she go make a little scribble in her bright pink notebook? Well, that was where things got a little funny.

If there was any drawback to screwing Debby’s pretty little brains out, it was the fact that she was always telling stories about how she used to be a star quarterback, all-state, with an arm like a bazooka. Since she only ever spoke in a breathless, high-pitched gush, and since the listener was often more than a little distracted, it took several visits for even the most attentive trucker to actually register any of it.

It didn’t help that the story was absolutely ridiculous: apparently, before she went by “Debby,” the pretty young transsexual had been “Dash,” a handsome, talented athlete whose two primary activities were destroying opponents on the grid-iron and screwing cheerleaders in the bleachers. Listening to her babble about deflowering the prom queen, while she herself had her waxed-smooth legs up in the air, high-heels resting on her partner’s shoulders, was slightly surreal…some of the truckers found it weirdly titillating, while others thought it disturbing.

Either way, everyone could agree it was strange that a girl who had worked so hard to shed every possible vestige of her born gender would keep nattering on about her “pre-transition” life. Even stranger, she didn’t seem to consider herself transsexual at all. When one of the more thoughtful truckers broached the subject after his session, lounging on Debby’s tiny bed as she scurried about hunting for her discarded bra, the ditzy blonde bimbo seemed almost affronted.

“Of course I’m not trans!” she chirped, with her perfectly groomed brows moving as close as they ever got to a frown. “And I’m not gay either! I’m just as straight as you are!”

Then, in utter contrast to her words, she hinged forward at the waist to retrieve her fallen bra, giving her customer a perfect view of the tight little ass he’d just so thoroughly enjoyed. Things got even more perplexing when she spoke about the circumstances surrounding her transition: the truckers had figured her “star quarterback” cockamamie had a grain of truth to it, and that Debby had probably been deeply closeted in some small Texas town, and had then moved away to become her true self away from scrutiny.

But that wasn’t the story Debby told. Rather, she said it all came down to one single, fateful night: the night “Dash” led “his” football team to victory in the state championship. The beers had begun to flow immediately afterward, and at the wild party that followed, the quarterback had his pick of the cheerleader litter…but since he’d been riding such an adrenaline high, feeling utterly invincible and unstoppable, he’d decided to warm up by forcing himself on a mousy little sophomore girl, assuring her afterwards that nobody, in one million and one years, would ever believe her if she tried to press charges.

“She totally wanted it,” Debby would say, blinking her pretty blue eyes innocently. “I mean, I had just won us the championship! Come on!”

Hearing a blatant confession of assault would have been a definite mood-killer, if not for the fact that the truckers considered it to be total nonsense. It had to be, since Debby’s story only got more fantastical from there: apparently, just a few weeks after “Dash” committed his crime, the football program’s newfangled sports psychologist had recommended him guided meditation sessions. The downloadable audio files were designed to improve his focus…but they had other effects, as well.

The truckers had to admit that the mental images produced by this part of the story were, at the very least, entertaining. Debby would describe, wide-eyed, how strange, uncontrollable behaviors had begun creeping into her manly, macho lifestyle: instead of swaggering through the school hallways, the quarterback would find himself mincing, swaying his hips and tucking his elbows, wrists flared as if to display a non-existent manicure.

In the middle of class, lounging in the back row with his buddies, he would suddenly cross his blue-jean-clad legs at the thigh and tap his pencil pensively against his pouted lips. In the cafeteria, where he normally loaded up on burgers and fries, free of charge for the school’s big football star, he would suddenly squeak out a high-pitched request for salad, with dressing on the side. As much as he tried to play off these odd tics as humor – mocking the school’s few gay students was one of his favorite pastimes – it soon got even worse.

Before long he was asking the cheerleaders to help him clean up his “gross, bushy eyebrows,” and swinging past the department store to search for the biggest size of high heels he could find. His bizarre behavior had thrown everyone for a loop, but his tough guy reputation, and the fact that he’d just won them the championship, extended their good will. When their star quarterback showed up to school with freshly shaved legs, displayed by indecently short denim cut-offs, they assured each other he was cutting down wind resistance.

When he started carrying his books in a bright pink handbag, and applying lip gloss between classes, they assured each other there was an elaborate prank in the works. When he asked his baffled parents to buy him a make-up table, they assured each other he just wanted to practice applying the eye black that cut down glare during sunny games.

When he started staring longingly at his teammates' crotches in the locker room after practice, biting his lip and blushing…well, that was a bridge too far. Not only was the sports psychologist brought in, but so was the local preacher, just in case an exorcism was required. The football coach rightly pointed out that Dash’s bizarre behavior had started not long after he began listening to the psychologist’s audio files, but she assured him that the guided meditations were completely harmless, and played a few to prove it.

She suggested that what was really going on was far more simple: Dash had been suppressing his true nature for a very long time, but he, or rather “she,” was now ready to come out of the closet as a loud, proud, pretty young transwoman. Dash had stared at her in utter horror, and opened his mouth to tell her to go screw herself, but somehow, for some reason, in a breathy, girly voice he’d never used before in his life, his sentence came out sounding more like…

“Oh my god, yes, totally!” Debby would say, repeating the fateful words years later with an almost rueful look on her pretty face. “And then after that, it was all downhill! I got kicked off the football team, kicked out of my house, I had to change towns…” She gave a theatrical sniff. “That bitch of a psychologist ruined my life! But no matter how hard I tried, I couldn’t tell anybody I knew. Like, I can barely tell you boys now, and I haven’t listened to one of her audio files in years!”

But that was the closest to angry Debby ever got: soon after, she would be all smiles again. Later, she confirmed what the more astute truckers had already guessed: the sports psychologist who had implanted Dash’s mind with overwhelming hypnotic suggestions was also the mother of the sophomore girl he’d forced himself on.

“Oh my god, talk about petty, you know?” Debby would pout. “And the worst part is, there’s only one, um, “release condition” programmed in. Oh, hey, did you want to finish on my boobies? I don’t mind.”

As the truckers grew increasingly fond of Debby, they began to grow uneasy paying for it with a girl who clearly had mental issues. Some of them would discuss the whole thing, long into the night, on their radios…but it was a tough nut to crack. She claimed that she was saving up money to get her breast and butt implants removed, and go on testosterone supplements, so that the instant she met the “release condition” she could go back to being a macho, manly young stud named Dash.

But it seemed like Debby spent almost every cent she earned on makeup and lingerie. In fact, when the truckers pooled their money to buy her an expensive pair of heels or earrings, she would squeal in delight and shower them in kisses. Furthermore, she was all too happy to wear whatever sort of sexy outfit or costume her customers provided, and her moans of pleasure during seemed awfully realistic, even for a seasoned pro. The smile on her face and bounce in her step contradicted her story of woe, as well – and when one of the truckers hinted she might benefit from seeing a therapist, she huffily refused.

It was hard to remain concerned for someone who seemed so happy with her lot in life, so the truckers mostly decided to just treat Debby kindly, and enjoy the benefits. As they watched her wiggle her way around the parking lot, high heels clopping noisily and jewelry flashing in the sunlight, casually tossing her peroxide-blonde mane over one shoulder, her story seemed more unbelievable than ever.

There was no way a swishy, bubbly girly-girl like Debby could be the product of a couple hypnotic suggestions – instead, it had to be some strange fantasy of hers, possibly just as gratifying as the fantasies she fulfilled for her customers. As her latest benefactor splayed back on the sheets with a contented groan, he was treated to a sultry over-the-shoulder smile.

“One thousand!” she chirped. “Hooray!”

The trucker blinked in confusion. “What’s that, honey?”

“You’re number one thousand,” Debby explained, mincing over to her little pink notebook. “Remember what I said about the, like, “release condition” for the hypnosis?” She made a little tally mark, then held the page up for him to see. “All I gotta do is have sex with a few more guys,” she beamed. “And then I get to go back to screwing cheerleaders and winning football games!”

Her customer stared at the page, eyebrow raised. “A few more, huh?” he asked, puzzled.

“Yep!” Debby said proudly. “The psychologist said I had to get to one million and one, and you’re number one thousand, so I’m, like…” She bit her puffy, gloss-coated lower lip. “Definitely over halfway there?” she said hesitantly.

The trucker gave a weak smile. “Well, you’re definitely making progress, honey,” he said.

Debby giggled in delight, bending down to give him a peck on the cheek. “You’re so sweet,” she chirped. “Go tell your friend I’ll be ready for him in five! I just have to redo my makeup, okay?”

The End