One Step Further Ch. 01

DISCLAIMER: Nothing in this story is real or should be considered as such. This story is very odd and is based on a strange fantasy I concocted that brings together some fetishes I'm into. This first chapter introduces the characters, sets up a little bit of where the story will be going, and yes, features hardcore sex between consenting adults. I do know where the story is going to be headed and have the future chapters mapped out in my head. However, I welcome any feedback and I'm always excited to discuss the story and characters, and chatting/bouncing around ideas for future stories. I hope you enjoy delving into my insane mind.

NOTE: This story features characters that appear in my other stories. They do not take place in the same continuity. Each series can be considered its own universe of sorts, with difference events, relationships, and couplings.

ONE STEP FURTHER CHAPTER 1

Tiffany checked her reflection in her bedroom's standing mirror, quirking her mouth as she debated her outfit. Too casual, she eventually decided and pulled off her t-shirt. She figured she'd keep the jeans, not wanting to go the opposite way and come off too dressy. She just needed to find the right top.

"Remind me again how this isn't a date," came Kyle's voice from speaker phone. Stuffing the shirt into a drawer and pushing it shut with her hip, she grabbed her cell from the dresser and made her way over to the closet. She flipped through the tops hanging inside with one hand while holding her phone with the other. "Cause it feels a little like a date."

"Mainly because I'm dating you," she said matter-of-factly. "For, like, the past month."

"Yeah, I know, it's just..."

Kyle trailed off as Tiffany found the perfect top and tugged it off the hanger. It was loose and oversized with a wide neck that would reveal her collarbones almost all the way to her shoulders but the cotton knit was the perfect style, right between casual and formal, and the heather gray went well with the light blue of her tight jeans. She laid the top onto the bed and placed her phone next to it, freeing both her hands. She unhooked her bra, releasing her modest breasts, and removed the straps, which would have been clearly visible and just too suggestive in her mind.

"It's just dinner with a friend," she reassured him, slipping her bra back on and pulling the top over her head. "I'll come over right after, I swear."

"Okay," Kyle relented. "I'll see you later tonight then. Bye."

"Bye."

Tiffany hung up and sat down her bed with a sigh. She brushed her thick, wavy hair straight and then started tying it into a loose braid.

She had heard the insecurity in her boyfriend's voice, but that was nothing new for Kyle. It was one of his defining characteristics. Not that Tiffany was much different. She possessed her own set of timidities and a lack of self-confidence that came from being a rather late bloomer. In fact, it was only this past year that she finally filled out, although admittedly not by much. Even still, she'd gone from awkward and gangly to long and lean, a taper in her waist and a little more in her chest and butt doing wonders for her figure. And she always had a very pretty face, with thick lips, dimples when she smiled, and a perfectly proportioned nose. However, she did have brown eyes, brown hair, and glasses, so a lot of guys still saw her as a touch plain.

Not Kyle though. Kyle always had a thing for Tiffany, even before she hit her prime, and a month ago he finally worked up the courage to ask her out, much to, well, almost everyone's surprise, including Tiffany herself. However, the two had always enjoyed each other's company, so they slipped into dating rather easily. They liked the same movies, books, and tv shows, and felt very comfortable talking and spending time together. Their relationship was strong, but Tiffany knew exactly where Kyle's nervousness was coming from.

While the emotional part of the relationship came easily, the physical part had barely progressed since day three.

Sure, they'd held hands and kissed, and on more than one occasion, their make-out sessions had gotten rather hot and heavy: tongues entwining, lips smacking, breaths panting. But the furthest Kyle had gone in terms of touching her had been hands on her hips, neck and back. Tiffany certainly wanted them to go further, god did she want it and so much more, but her own insecurity kept her from initiating things. Neither her nor Kyle had ever dated anyone else, and that inexperience seemed to be holding back both of them.

She did wish he was a little more assertive, that he would demand from her the types of things her mind and body longed to do, things she thought about at home when releasing some built up... energy. But she was willing to go at his pace and would do whatever he wanted whenever he was ready to ask for it.

But she understood why her going to dinner with another guy might set off some of his insecurity alarms. If she was being honest with herself, Tiffany also found the whole situation just a little strange, but she had already accepted the invitation and the Midwestern sensibilities in her would have been mortified at rescinding.

As Tiffany gave herself one last look in the mirror, pleased with the result, her phone dinged. Dylan was here. Running out the door, she hopped into the passenger seat of his car with a smile, glad to see he was dressed in a pair of jeans and a polo. Her choice of attire was perfectly on point.

"Hey!" she said brightly, clicking her seatbelt into place. "Thanks for picking me up."

"Of course," he said casually, backing out of her driveway and heading out. "You look great, by the way. I'm used to seeing you in your work clothes, and well, yeah. You look great."

"Thanks," Tiffany said with a slight blush. She stayed quiet for a moment, watching as they turned a few familiar roads. "Where are we going, anyway?"

"Oh, the Parlor."

Tiffany spun to look at him in disbelief. Dylan tried to hold a straight face, but he burst into a laugh almost immediately. She rolled her eyes behind her glasses.

"Can you imagine?"

"Well, you come in there enough."

"Yeah but my reason for that is right next to me," he said, again turning on the charm. Tiffany opened her mouth to respond, with what she didn't quite know even as her lips began to part, but before she could say anything, he continued, "Well, second most reason. I really do enjoy their salted caramel swirl. But ice cream isn't exactly ideal dinner."

"Uh huh," Tiffany said sarcastically, deciding to let his comment go. It actually felt nice to receive compliments like this. After going so long being mostly ignored, the sudden influx of attention was a welcome and enticing change of pace. "Just drive."

Dylan had been visiting Tiffany regularly at the local ice cream shop where she worked for the past few months. He nearly always waited for her to serve him and she always appreciated his easy-going and charming attitude whenever they interacted. He tended to tip generously and was by far her favorite customer. It didn't hurt that he was rather attractive, tall with sandy blonde hair, hazel green eyes, and a strong jawline. Her coworkers teased her mercilessly about him, constantly saying that if they were her, they'd have taken him to the break room and gotten their own creamy treat already. They even offered to cover for her if she ever wanted to.

Tiffany had never entertained that particular thought. Well, that wasn't true. She sort of did once.

Late at night, at home in bed, hand down her pajama pants and under her panties, slowly playing with herself, she had imagined doing something that kinky. She tried thinking about Dylan coming in, her biting her lip and leading him toward the breakroom, locking the door behind them. But she wasn't feeling it... until she turned back around, and it wasn't a naked Dylan standing in front of her when she dropped to her knees. It was a faceless man whose prick stood at attention inches from her face. As she imagined parting her lips and taking him in her mouth, Tiffany grew wetter and stroked her clit faster. It wasn't the person that started to turn her on but the act itself, the sheer naughtiness of it.

As she continued to rub herself, eyes clenched and writhing on her bed, she pictured sucking someone off in that backroom, hurriedly bobbing her head so they wouldn't get caught. She was getting closer but not quite reaching her climax when in her mind, she looked up and Kyle took the place of the faceless man she was blowing. Her orgasm hit her like a train, a confluence of ideas slamming into her and rocking her body. Her slutty behavior, the taboo nature of the act, and the new idea that Kyle had asked her to do it, pulled her into the backroom and pushed her to her knees so she could suck his cock while on the job. It all came together and made her explode in pleasure.

That night had helped solidify Tiffany's feelings for Kyle and revealed a few other hidden desires of her own. It also let her know that despite his attractiveness, Tiffany wasn't actually that interested in Dylan, which made her acceptance of his invitation to dinner that much easier.

When he had asked her out earlier that day, she was flustered at first. Stumbling as she rang him up, she told him that while she appreciated the offer, she couldn't go on a date with him; she had a boyfriend. However, unshakeable as ever, Dylan had laughed it off and said that it wasn't a date. He just wanted to treat his favorite ice cream scooper to a well-deserved night out. Rationalizing that since she didn't have feelings for him and that it wouldn't be a date, she had decided to go for it and agreed.

She hoped the night wouldn't end with things blowing up in her face.

"Oh my god," Tiffany said excitedly, staring out the window as they pulled up to Rocket Reds, a '50s themed drive-in diner. Tiffany loved this place. The atmosphere, the waitresses on roller skates, the food. "How did you know?"

"I saw that you post about this place often," Dylan said sheepishly, putting the car into park and turning to her. "Sorry for stalking your social."

"Worth it," Tiffany said. If this was a date, she thought to herself, she'd have already been impressed.

Dinner itself ended up going really well. They chatted the entire time, naturally and easily, while dining down on burgers and fries, sharing their meal and picking from each other's trays, before splitting a shake between them to round out the night. While Dylan took care of the check, Tiffany finished up the shake. Out of the corner of his eyes, he watched her mouth encircling the straw and her cheeks hollowing out as she sucked up the last of the thick creamy liquid. She tossed the cup when finished and gave her lips a lick.

"I know I said just dinner, but I thought we could go somewhere to chill for a bit before heading back," Dylan said, starting the car. "If you're up for it."

"Sure," Tiffany said with a satisfied sigh. "After a meal that good, I'm tempted to let you take me wherever you want."

A short time later, Dylan pulled off the road and onto an open field just outside of town. From their parked position, they could see the water tower off in the distance and had a clear view of the night sky, stars shining brightly. It was one heck of a view. Tiffany turned to Dylan with a skeptical look. "So is this where you take girls after a date to make a move on them?"

"Maybe," Dylan said with a grin. "Or I just like it here and wanted to share it with you. One of the two but I'll never say which."

"It's too bad this wasn't a date," Tiffany admitted, taking in the sight outside the windshield while Dylan took in the view of Tiffany's profile. "You'd have done really well."

"Just because it isn't a date doesn't mean it can't end like one."

Tiffany heard a shuffling from beside her and the sound of a zipper. She turned to Dylan, meeting his eyes with a questioning look before drifting her gaze downward toward his crotch, where his semi-erect cock emerged from out of his undone pants. Tiffany's eyes went wide and her heart started pounding in her chest. She'd seen pictures, she'd watched videos, but this was the first dick she'd ever seen in real life, and as much as she knew she should turn away, she stared at it with rapt fascination. It fully hardened under her gaze, thickening and growing longer. Dylan seemed decently sized, maybe two or three inches past the width of her palm. He was a little thinner near the base, girthier toward the bulbous head, the tip of which glistened in the low light.

"Wha... What are you..." Tiffany looked up just in time to see Dylan lean toward her, reaching his arm out to the back of her neck. Realizing he was going to try and kiss her, she turned her face at the last second, dodging his lips. Undeterred, Dylan pulled her closer so he could kiss her long neck, right where it met her ear. She braced her hand on top of the console between them for balance as he gave her earlobe a lick, sending a shiver through her.

"It's just, I took you out to a great place you love, paid for dinner," he whispered into her ear. "If it was a date, I know how I'd have liked it to end, but even if it isn't one, it'd be nice if my efforts meant something."

"Is that what he assumed she was like?" Tiffany thought to herself. "That just because they had a nice dinner she would just, what, beat him off on the first date? God that would so, so... naughty." Thoughts and images flooded Tiffany's brain: going on a first date with a guy, having a nice dinner, and then afterward, pulling over to the side of the road so she could repay him. She'd thank him for taking her out as she unbuckled his pants, grabbing his cock and pumping it in her hand, willfully serving as his cum-pump... all because he bought her a nice dinner.

"Come on. After we had such a great—ahh!" Dylan gasped as Tiffany's fingers wrapped around his erect prick. He looked down to take in the erotic sight of his cock in her hand before lying back into his seat and lowering it down a few inches to make himself more prone. A groan escaped his lips when the usually timid girl began to slowly slide her hand up and down his length. "Ooohh fuck, Tiff. Shit that feels good."

For her part, Tiffany wasn't really paying attention to him. It wasn't even Dylan she was doing this to in her head, just a random stranger she'd gone out with for the first time. And now she was jerking him off. Continuing to stroke him slowly, she adjusted her position to get a better look at what she was doing. Pulling her legs up onto the cushion and tucking her feet under her, she turned her body to fully face him, kneeling in the passenger seat and placing her free hand on the console.

The feel of his cock was so new to her, stiff and hard, yet pliable. She ran all the way up his length to the tip and then back down again to the base before repeating the process, picking up speed, adding a little bit of a twist to her hand. It seemed the right thing to do as Dylan continued to moan and pant above her and the tip of his cock leaked a small bit of precum. Tiffany captured the slick slime in her palm, using it to lubricate her ever increasing pumps up and down his shaft. Her breaths came fast and shallow, her eyes concentrating on the arousing sight of her hand flying up and down her first cock, the rapid wet slaps of skin again skin beating a steady rhythm.

Her mind drifted back to her fantasy turned semi-reality. They were mimicking their real-life positions, Tiffany leaning on the console rapidly pistoning her hand on her mystery man's cock. Except it wasn't a mystery man anymore. It was Kyle.

Tiffany moaned and she heard a voice say, "Yeah, you like it as much as I do."

"Yes," she breathed out heavily. "I love jerking your fat cock."

Kyle had taken her out. He had pulled over. Said he wanted her to stroke his dick. She was pumping him just like this. Then he reached up, put his hand on the back of her head and pushed down.

Without any hesitation, Tiffany brushed a few loose strands of her hair behind her ear and then bent over, taking Dylan cock into her mouth.

"Holy fucking shit," Dylan said, instinctively thrusting his hip upward to sink more of his shaft into Tiffany's warm, wet hole. Her hand was still wrapped around him and it prevented him from getting much deeper, but as he dropped back into his seat, he looked down with wide, lust-filled eyes to see almost three inches of his cock inside of Tiffany's mouth. Her cheeks hollowed as she sucked hard and slowly lifted her head up, revealing more and more of his spit-covered member, before dropping back down again. "JeeeeeeeeeSUS!"

Tiffany's mind swam in a sea of arousal, spinning at the strange new sensation of a man's cock inside of her mouth. She reveled in the new feel of it, of her lips surrounding its girth, of its thickness filling the space and running along her tongue. She bounced her face up and down, letting saliva pool and swish around Dylan's cock, breathing out her nose. Getting a rhythm going, she bobbed her head faster and faster, her lips colliding with her encircled thumb and index finger. Below her, Dylan bucked and humped, wanting to force more of his cock into her gullet. She slid her hand a little lower, allowing him in another inch, the tip almost but not quite reaching the back of her throat.

"Oh, fuck yes!" Dylan watched Tiffany's pretty face rhythmically rising and lowering, the sight of his dick appearing and disappearing past her lips pushing him closer and closer to the edge. He tossed his head back as her tongue began to twirl around his tip, the pleasure proving too much for him. "I had no idea you were so good at this. Damn I'm close. Ah fuck. Ahhhh!"

As the first jet of Dylan's cum shot up his shaft, Tiffany halted her motion, stopping her bobbing with the edge of his mushroom tip just past her lips. Pulse after pulse of hot, sticky cum shot into her, coating her tongue, splattering against the roof of her mouth, as Dylan emptied himself into her formerly virgin hole. Once she felt his cock stop twitching and start to deflate, Tiffany sucked the rest of her way free. Holding his cum in her mouth, she leaned further over, pushing the driver's side door open, and spat the gooey mess onto the grass. Giving her lips a lick, she shut the door and relaxed back into her seat with a sigh.

A panting Dylan tucked himself back into his pants and raised his seat back up. "That was—"

"I'm ready to go home now," Tiffany said cutting him off and staring out the window.

"Oh, yeah, sure. That was just... wow."

He complimented her a few more times during the drive, telling her how incredible she was and how sexy she looked going down on him like that, but Tiffany didn't really listen to most of it, instead lost in her own thoughts. There was no doubt in her mind that what just happened—the twisted naughtiness of blowing a guy as a thank you for dinner—turned her on. In her mind, that guy was Kyle, but she knew that in reality it wasn't her boyfriend's cock that she had sucked, it wasn't his cum that she had taken in her mouth. She wanted it to have been Kyle, she wished it was him that she had that insanely arousing and kinky experience with, but it wasn't. And all those thoughts left her with a mix of guilt and want and horniness.

Even after Dylan dropped her off and she thanked him for taking her out, even as she got into her own car and started the drive to her boyfriend's place as promised, she had no idea what she was going to do. She didn't care about Dylan. It didn't matter to her in the slightest it was him. The entire thing was purely sexual and she truly was thinking of Kyle. In fact, imagining it was her boyfriend is what ended up turning her on the most. She had to tell him. She couldn't keep something like this a secret, not if she liked Kyle as much as she did.