Bumpy Ride

Jamil often wondered what he had gotten himself into by dating Leona. His mother, in grief from him quitting the Asim’s and joining Leona in travelling the world, joining explorations of ancient magic sites, called it 'him quitting to become a stranger's floozy'. Which Jamil stood firm that he wasn’t, it’s just. They were both really good at getting the other to do things. That’s part of how he was finally able to quit the Asims, with the understanding they’d both finally start doing what they wanted. But Leona also liked seeing him fucked out of his mind, unable to do anything but succumb to the pleasure, Leona also had a lot more cash than Jamil.

It wasn’t that Leona would flash cash or gifts to get Jamil to drop his pants and act like a slut. Jamil refused to do that, and Leona knew that, which is why he leaned into Jamil’s suppressed competitive side, making bets around them instead. Jamil had a love hate relationship with that, he hated how close it took him to being a floozy like his mother accused, but it also left him satisfactorily ‘fucked stupid’ and occasionally with a new expensive piece he’d never be able to afford on his own. And Leona was so good at knowing what he wanted and how to make him cum.

Which brought him to his boyfriend and the new toy he had gotten for him. They were going on an eight-hour car ride to the next location, much of which was on bumpy, unpaved roads. Leona initially wanted to hire a driver, but Jamil wanted to take turns driving, just because he had money didn’t mean he had to throw it around all the time. Leona, however, got a devious grin and suggested he do all the driving in exchange for Jamil doing another challenge, and he threw in the prize of an expensive & highly accurate replica of the Sorcerer of the Sands’ Staff.

The challenge was simple, Jamil just had to get through the eight hours without cumming. Jamil set some strict rules about it too. Leona wasn’t allowed to touch him, else the challenge was void; only one toy, nothing with batteries or any kind of remote. He should have known Leona had a trick up his sleeve.

It was tall and thick with swirling colours covering it, the shape was odd, more animalistic, though Jamil couldn’t name what animal. More damning was the hole at the top, which peering in showed something in the tube. The bastard found a way around his one-toy rule.

“Is it even going to fit?...” Jamil wanted a reason to back out, but he wanted that sceptre.

“I brought your favourite lube, and I know you’ve had thicker things inside you~” Leona teases, giving him one last kiss.

Jamil, with a groan, dropped his pants and braced himself against the nightstand with one hand, using the other to prep himself further. That staff better be worth it.

It took effort to get it in, Leona offering no help, to ‘honour’ the rules, of course. Jamil, once the top of it was in, turned around, making himself slowly sit on it until it was firmly in place. Taking a moment, he gets his underwear and pants on, and Leona, to his credit, hands him a couple of blankets to take to the car, covering his erection.

In the car, Jamil sits in the front seat, noticing the large plush bird in the footwell.

“If we get drive thru you’re going to want something to cover it, and I won’t be available if you need something to squeeze~” he teases in that thoughtful way Jamil fell in love with.

For the first couple of hours, things weren’t so bad. Leona still avoided potholes, and the slight rumble didn’t do much; his boner was even starting to go down.

Then Leona let the car slip just slightly, and onto the rumble strip, causing his side of the car to quake, and the dildo to vibrate. Jamil sputtered, squeezing the plush macaw tightly as his toes curled and something slipped out inside him.

Leona laughed, going back to driving properly, getting as much of a glare as Jamil could muster through his lust.

Leona smirked, “Whoops.” There was no way Jamil was winning this, or Leona letting him back out of this. Not that Jamil really wanted to…

Hour four, and Jamil was going insane. The three ‘eggs’ were loose inside him, rubbing him deeply in places he hadn’t had touched before. They were no longer on a paved road, and were now on a rouch, packed-down path, a low rumble vibrating the car and by extension the toy. His body was trembling as he threw his head back over a surprise bump.

“Lost yet?~ The road gets much bumpier in a bit, the location is very remote~” Leona teases, watching him squirm in the corner of his eye.

“Not- yet!” Jamil pants, trying to find an angle that didn’t jostle the toy with every bump. He wasn’t having any luck; each angle just caused it to move in a different way.

“Just give in, it’ll feel so good~” Leona purrs from the driver’s seat.

Jamil really wanted to give in, even if it meant losing the bet. There’s no way he was lasting another four hours of this, not when the road was getting bumpier and bumpier. He wasn’t able to hold it in, staining the front of his pants.

He whimpered as the car ride and subsequent rubbing continued. He knew that Leona wasn’t going to help him get it out until they arrived; it was the common penalty of their games.

But despite how overwhelmed his body was, and how Leona would probably fuck him once their tent was set up tonight. He couldn’t help but look forward to it. Leona really did know how to get him to do the things he didn’t want to admit to wanting.