Trans Canada Highway (Story)

Sorry for the delay! Was doing NaNo, got derailed, started writing a tabletop game, you know how it goes. Hopefully this helps assure you that I am still, in fact, pretty lewd.

This story is a pretty squishy story between two good friends who become more and features some MUSHY themes but also includes a light reference to transphobia due to growing up in the sticks. It's brief and largely irrelevant but, well, verisimilitude. Just a heads up!

Also the only sex is a buttjob/handjob combo. Sorry, I have simple tastes that need to be sated.

Don't @ me over the title, I just live here ok.

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“Are we there yet?” Skylar asked, knowing full well that they weren’t. She had her legs up on the dash of Zak’s sedan, the right side of her purple hair flicking around in the blowing wind. It was an unseasonably sweltering October day, and the flow of air was the only cooling they were gonna get. Stupid climate change.

“No,” Zak replied, in the same tired tone he’d used the last five times she asked. Skyler could be smart, funny, and great in a jam. But goddamn it all to hell, she might have been the worst person on Earth to ride shotgun. Just a few more hours, he thought. A few more goddamn hairpulling hours and they were back at college. Reading week had blown by, and aside from a night at the town bar, they hadn’t hung out at all during it. Something always came up.

They’d known each other since high school, back when he was a flunking jock having to deal with a knee injury and a prospect of needing to try in academics and she was, well, a little different. It was tough being a closeted trans girl in rural Ontario. But she was smart as a whip and the perfect tutor for someone who needed to learn just about everything. And he got the bullies off her back while she dealt with her gender stuff. They’d been bonded by that, up to and including taking post-secondary offers in the same city. The only downside is that it was a 12 hour drive back and forth.

No matter how much you like someone, it was tested by half a day in the same early aughts Sonata crammed to the brim with stuff and not a single wisp of air conditioning in sight.

“Next gas station I’m pulling over,” he told her. Zak tested his grip on the steering wheel. Squeezing hard enough for his knuckles to turn white, then letting go. One of the many ways he coped with stress.

She leaned over to check the dash. “We still got half a tank left. You trying to bilk me for more gas money?”

He snorted. “No. But if I don’t stand up and walk around, I’m going to lose it. You get to tune out on your phone, I have to stare at fucking rural highway for hours on end and not fall asleep.”

Skylar nodded. “Alright, yeah, fair. I don’t want to do a header into a tractor trailer if I can avoid it. Could always use more road snacks.”

Blessed relief came ten minutes later at a town so small it barely registered as one on his phone’s GPS. It sported a single independent gas station and convenience store, and Zak almost rolled the car in his eagerness to pull to a halt. They came to a stop in one of the spaces and shut the car off. A beat. Then, it rattled, groaning like a dying ocean liner hit by a torpedo. The noises stopped, and for a moment they thought this was it, the moment where the car had finally given up the ghost. But Zak slid the key back into the ignition and, with some reluctance, it turned over again.

“Ok, we’re good,” he said, shutting the car off again. They both piled out of the car and stretched their legs.

Skylar had her usual ‘fallen through a Goodwill for weebs’ look on, with a crop top emblazoned with something in Japanese and a pair of cutoffs that were just a little too tight to possibly be easy to get into. Sweat was making her top cling a little closer than usual, revealing the outline of her bra. Zak kept his eyes firmly off her curves, though he did note that her HRT had given her another growth spurt recently. She’d always been a little heavy set, but how her weight was being redistributed around her hips and chest was doing terrible things for his composure.

He himself was dressed much less conspicuously in loose fitting jeans and a band t-shirt, comfortable clothes for the long drive they were in for. Not exactly setting hearts a’flutter, but his hair was always neat, and the black-framed glasses made him look a lot smarter than he actually was. You could get away with a lot as a dude in your early 20s.

“You want me to go in?” Zak asked. On the road, he was usually the one who went into the stores. Though she had no problems being herself, sometimes she didn’t want to deal with the snide comments from some dork from the same kind of hick town she grew up in.

“Could you? Get the chips I like, and the flavoured water thingies. I’m gonna take a walk,” she said, pointing at a sign that indicated a picnic spot just over on the other side of the road. He nodded and fished out his wallet, hoping there was enough cash for snacks. You never know when you’re going to run into a place with a broken debit machine and no ATM for kilometers. Sure enough, all he had were a few loonies.

“You got cash?”

She leaned back into the open window of the car and pulled out her wallet.

“Catch!” she said, tossing it over the roof. He did.

“Too easy. Used to play basketball, y’know,” he said with a grin.

“Oh really?” she asked, going through the motions of their running gag. “Were you good?”

He puffed out his chest. “Couldda been pro.”

Getting the snacks in the gas station was painless save for some banter about the weather with the cantankerous cashier. It was, indeed, a hot one out there. Zak carried an armful of treats to the car and tossed them in the mostly empty cooler lodged in the back, then went back for a refill of ice. By the time everything was nice and chilled, he noticed a disturbing lack of Skylar. He looked over toward where she’d walked off, not a wisp of dyed hair. Zak sighed, locked the door, and jogged to the other side of the road.

Finding her wasn’t hard. A little scenic overlook had a collection of faded picnic benches clustered close to a chest-high stone wall. Sitting on the edge, feet dangling, she looked like she didn’t have a care in the world. He felt that tingle in his chest sometimes when he was around her. It was easier to brush it off as annoyance than to examine it. Yes. He was really ‘annoyed’ by her.

“You okay, Sky?” he asked, jerking a thumb back toward the car. “Got the goods.”

“Just enjoying the sights,” she replied. Heat aside, it was a gorgeous day. A vast panorama of green with hints of the first yellows of the upcoming fall. The occasional car speeding past and the rustle of the foliage were the only sounds he could hear.

“No kidding. It’s gorgeous.”

Zak sat down next to her. A whole world stretched out beneath them. He never liked heights, but he could sit for a while like this. With her.

“You still like me, right?”

The words hit like a bullet. “What? Of course I do!”

Skylar kept her eyes out into the middle distance, feet kicking back and forth. “It’s just that...the last year we didn’t see much of each other. We hung out once or twice during the summer, but I was feeling like you wanted to keep your distance. And during the ride, you seemed like...” She trailed off, letting the accusation go unsaid.

“Hey, look. We both got our programs to deal with. I’m buried underneath labs and assignments and you got so many readings you told me your eyes were about to pop out of their sockets. I guess I wasn’t paying attention to how little we were hanging out.” That was only partly true. He was busy, but he could have made time for them. He had been thinking about her, but he hadn’t actually sacked up and texted her. Excuses, excuses.

She nodded. “I guess I couldda been more vocal about it. I missed you.”

He placed his hand on top of her’s. The world stopped. There had been an unspoken barrier between them, one he had just crossed. This was the closest they’d gotten since before she transitioned. He didn’t want to seem like a creep. He especially didn’t want to seem like a creep to her.

“Is this okay?” he asked. Zak could barely hear his own voice for the hammering of his heart. What was going on? What was he doing?

“Yeah.” She faced him, revealing the tiny constellation of freckles under her eyes disappearing against her reddening cheeks. “I like it.”

“Okay. Because I missed you too.” He squeezed her hand. She squeezed back.

“Really?” she asked. “I thought we were, like, drifting apart.”

He was staring now. They both were. They had always been friends but the more she became the person she wanted to be, the more attractive she got. They’d always got along, but her self-confidence, her style, the way she laughed now. It was like a drug to him. Keeping his distance hadn’t worked.

“We don’t have to.” He said, his throat suddenly dry. “In fact, if you wanted…”

She kissed him so hard it nearly took them both over the edge of the scenic overlook. Adrenaline shot through him, making him grab onto the edge of the wall with one hand and her arm with another. They pulled away for a second to confirm they weren’t about to fall off, then went in to continue the kiss. By the time they broke away, he was sure this was no accident. This is what they both wanted.

“I’ve always been into you,” Skylar said as she tried to catch her breath, “I didn’t know it, but I felt it. I just never thought you’d be into me.”

Zak couldn’t quite find the words. He tried though. “I’m into girls, you know that,” he said, to a cautious nod. “But I just didn’t know you were a girl until we were friends. And then afterward...I didn’t want to fuck it up.”

“You won’t. You can’t.” They kissed again, this time mutually meeting in the middle before Skylar let Zak take the lead. She wrapped her arms around him, the gesture inspiring just about every protective instinct in his body...among other things. He still needed to keep her safe, but he also wanted more from her. More than he’d ever dared to. Her perky breasts, her rounded ass, she was so fucking hot. Suddenly, his loose fitting jeans didn’t feel so loose anymore.

She pulled him away from the edge and over to one of the picnic tables. Pushing him into the bench seat, she gave him a flirty wink. “Took ya long enough to get the hint, Jeez. Was worrying I was gonna have to dress even sluttier.”

“You were dressing slutty just for me?” he asked, genuinely surprised.

“Well, I also like dressing slutty. But if you’re liking it…and it seems you are~” She gripped his stiff bulge through his jeans. He shuddered. Fuck. Having a woman who wanted you felt fucking good.

“You wanna do it here?” he asked, nodding out on the forest below. There was nobody visible through the thick canopy, but they’d surely be exposed to any curious onlookers down below.

“You got a problem with it?” she asked.

He could get his pants down soon enough. Cock out moments later, he pulled her down into a kiss before asking the Million Dollar Question.

“Can I…y’know…” he asked, looking down at her cutoffs.

She shook her head. “Not without prep. Buuuut.” She turned her back to him and worked at shimmying out of her cutoffs down to her panties. “What if I got you off with my ass?”

“But I though-” he began, then, with an eyebrow raise, “Oooh. Huh. Didn’t think of that.”

“Ugh, I bet your browser history is really boring.” She took her time taking off her panties, bending over to really give him a good look at her disproportionately enormous ass. His cock looked like it could settle down and make a home there between her cheeks. As if reading his mind, she sat down on his lap. She slid back, riding up against his dick.

“Nnf. Fuck, careful,” he warned.

“Oh? What are you gonna do about it?” she taunted, pulling back onto to push further against his dick. He got the idea and grabbed her hands with his. Skylar gasped.

“You want me in charge, is that it?” he asked, squeezing her wrists.

“Please,” she admitted, a little more shaky than usual. He took that as free license to use her as he saw fit. He put his hands on her waist and raised her up, only to gently let her go, keeping his thick cock pressed up against her ass. Practically jerking himself off with her rear end. Strangely, or perhaps not so strangely, it felt fantastic.

Zak squeezed her ass cheeks together to keep a tight grip around his shaft, then got to thrusting. Each inch of drag tortured him ever so beautifully. He kept her close, kissing at her back while he used her. It wasn’t enough goddamnit. He wanted her wound up tight.

“You do this with all the guys you know?” he asked, testing the waters for some dirty talk on his end. Sure enough, she gave an exaggerated huff.

“No! Just the ones I like. I’m not some kind of, y’know, buttslut.” Her words trailed off at the end there, almost like she was embarrassed by the entire concept. Or because she wanted to be called that.

“I bet you are. I bet you get all kinds of people off with this fat ass of yours,” he said, slapping her cheek for emphasis. The spank made her flesh quiver and an adorable yelp escape. “Shh, don’t make so much noise! Everyone down there’s gonna see you. Gonna watch you make me cum like a good little buttslut.”

He kept her still while he used her, listening to the gasps and sighs and using them as a roadmap for his own motions. He didn’t need to do a damn thing more to drive him closer to orgasm, but she was another matter.

His hand slid around the side to her cock. It wasn’t large, maybe three inches stiff. It was only half-hard at the moment, though not for lack of excitement from what he could tell. He gripped the sensitive stick between his fingers and started stroking, making the chubby cutie moan with delight.

“What’s this little thing then?” Zak hissed into his eat before giving it a nip. “You call this a cock?”

“Y-yeah…”

“Wrong. This is a fat, drippy clit, nothing more.”

Skylar exhaled hard as his words struck home, humping into his questing fingers. Zak temporarily reduced the pace of his thrusts to tease his friend turned lover, dancing his touch along her length only to rub the little sensitive place where her foreskin met the head. She was dribbling precum like a busted fountain, much to his amusement.

“Ah!~ My...my clit...fuck…” she wheezed, unable to contain her voice. Every little degrading word and low treatment was driving her rebellious heart wild.

“That’s right. Clits like this squirt whenever they get even a little excited. I bet you just love the feeling of soaking your shorts, don’t you?”

Her head snapped up and down. “Yes, god yes…”

Zak laughed. “I fucking bet. Would you like it if I added to that, then? Shot a huge, thick load of cum all over your pretty panties, made you walk around in them? This little dicklet spending all day swimming in my seed, marked as mine. My toy to play with.”

She twitched in his lap, trying to keep still so the pleasure could keep coming but Zak made sure it was impossible. Her moving around only drove more sensation to his cock, which only made him more invested in teasing her til she popped. Wet little slapping noises could be heard as his fingers slid along skin slickened by her helpless spurts of precum.

“You’re gonna cum to this, aren’t you?” he pressed, squeezing her tip with thumb and forefinger as if to emphasize the point. “You’re gonna cum your brains out to a little bit of foreplay and having your ass humped. Maybe we need to lock this little thing up so you can focus on your real sexual organ: your slutty hole.”

Skylar shuddered, little squirts of seed splashed onto Zak’s fingers. He milked her to completion, making sure to thrust forward and get every bit of joy out of her involuntary quivers.

“Good girl! You made such a mess, though. You know where this goes, don’t you?” he asked, raising the cum covered fingers to her mouth.

She nodded, opening her plush lips wide. Zak pressed each sticky digit inside her in turn, letting her fellate his fingers to get every last drop. Afterward, he wrapped her in a hug and redoubled his thrusting, using her ass like a cheap fucktoy. All while she swirled and gurgled her own spunk. She swallowed with an audible gulp.

“Mmm~ I’m your cumrag. Give me more, please. I need it!”

“And are you a buttslut too?” he asked, reaching his breaking point.

“I’m a buttslut! My hole needs your cum! Oh god, give me all of it!”

It was all he needed to hear. He pulled back, squeezed her cheeks together, shoved his cock against her hole, and finished himself with a few quick strokes. Thick gushes of seed splashed against her backdoor, a small river rolling down her ass and pooling between her chubby thighs. She moaned shamelessly, feeling the sticky seed slide down and drizzle down her legs.

As the endorphins faded and the blood rushed back to where it ought to be, they broke away from one another. It was like a spell had been broken and they remembered their history, their journey together.

“Whoa…holy shit,” Zak said, working to catch his breath.

“This was okay, right Sky? Didn’t mean to make this weird,” Zak began. She put a finger to his mouth.

“This thing...it can be just today, or more, or whatever. Just promise we’ll stay friends. I mean, not like…” Her normally blithe confidence flagged as she struggled for the right words. “I mean we can be friends, or we can be more, but promise you won’t get weirded out or drift away. You’re the only thing ‘sides my folks that I kept. I don’t want to lose you.”

He let go of her hips, letting her spin around to face him. “You won’t. This was...unexpected, but I liked it. Did you?”

Her head nearly flew off her neck from the force of her nod. “Fucking duh, dummy, of course I liked it! I haven’t cum like that in...ever, maybe. We made a bit of a mess, though.”

He laughed. “Yeah, well, I won’t tell if you won’t. We smell a little bit like a teenager’s sock drawer though.”

“Ew, gross,” she said, tossing her shorts at him. He snatched them out of the air and underhanded them back. She missed the catch. “Fuck. Forgot, you used to play basketball.”

“Couldda been pro,” he recited. “Alright, well, we ain’t making it to the city by nightfall at this rate. Vote to stay at a chintzy roadside motel?”

“No AirB&Bs around here?”

“You kidding? Round here they’re either out of our price range or booked up by bougie fucks from Hogtown to see the leaves change. No it’s a motel or we rough it in a parking lot.”

“Fuck that, true crime it is. Least we’ll have a shower.”

He nodded. Then, with a grin, he added: “And a bed.”

She tilted her head and gave him her best ‘are you fucking kidding’ look, but it melted into giggles. “So I guess that answers my original question. People next door better hope the walls are thicker than cardboard.”

They piled back into the car and set off down the road, toward the future. Together.