Chapter Two — Callum
I spent a while crafting this challenge.
I wanted to do something different after all of the bar games we played — darts, pool, poker.
I wanted to mix it up and do something a bit more fair, because even I have to admit the push-up challenge we did definitely advantaged me, although I let Alex do push-ups on her knees.
For this challenge, we’re starting fires. Which I have zero experience doing. You could say it’s pretty stupid of me to pick this as a challenge, but I wanted to be fair. So I chose a game that would be new for both of us.
As much as I should hate Alex — for seeing my cofounder Trent behind my back and lying about it — I can’t bring myself to. Because, except for that betrayal, everything else about her is positive. Alex is sweet, kind, and the smartest girl I’ve met. She’s fascinating.
Which makes her betrayal all the more confusing.
No matter how I think about it, she just doesn’t seem like the type of girl who would do this.
I wondered at first if there were some major signs I missed, but after thinking about it for a long time, I’ve come up with nothing.
It still makes absolutely zero sense to me.
Still, I saw her phone light up like the 4th of July the other night with Trent’s name. And she told me, plainly to my face, that it was her mom. There’s just no getting around that.
I have to keep reminding myself about what she did, because it would be easy to forget and slip back into the way things were. The way they were before that night.
A large part of me wishes I could. But I can’t. So I need to do the next best thing, and that’s getting her to quit these games.
Which is going to be tough. Alex is smart and resilient.
She’s resourceful. I really should be picking games I know I can crush her at, but I just can’t bring myself to do that.
Yeah, she betrayed me, but that doesn’t mean I should tilt the games in my favour.
I’m going to beat her fair and square. It’s only right.
Although, I wonder if part of me is just being soft, trying to prolong this because I’m not ready to say goodbye. It’s something I’ve been asking myself all week.
Oh well. No time to think about that now.
I head off towards Alex’s place. I offered to drive her there, since it’s in the middle of nowhere. Most men in my shoes would have forced her to find her own way there, but I would never do that. She’s still a lady, and I would never leave her to fend for herself.
She’s three minutes late, which I promptly inform her of when she slides into the car.
“You’re late,” I say.
“Sorry,” she says, shrugging.
I try to suppress my smile, but I can’t help it.
“You know the drill,” I say, nodding towards the driver’s console.
She pops it open as if this is a routine we’ve been through a million times, when in fact it isn’t, really.
But then again, I’m sure she isn’t surprised that there are consequences for being late.
There’s always consequences with me. She knows that.
She looks in the console and pulls out a new box. She’s probably expecting a vibrator, which is why there isn’t one; I’m a man of surprises. She opens the box, and slips out a silver butt plug with an emerald jewel at the center.
She blushes, and I feel my cock stir.
“Did you have this planned?” she asks.
“Only if you planned to be late,” I say.
She laughs.
“There’s lube, too,” I say.
She blushes again.
“It’s so cute when you blush,” I say.
She lets her hair fall in front of her face.
“You can’t hide from me, sweetheart. You know that, right?” I say, grabbing her chin and turning it towards me.
She tries to move her head, but I don’t let her look away. I stare into her eyes, forcing her to be uncomfortable for one or two more seconds. That’s the sadism in me. Then I release her.
I bet she’s wet. The thought pops into my head.
“Before putting that in,” I say, as I start up the car, “show me how wet you are.”
She looks at me. I raise my eyebrows.
“Yes, sir,” she grumbles, before slipping a finger down her black Lycra pants.
She pulls it out and it’s glistening. She tries to lower it out of sight, and I say, “Hey. Don’t shy away now. You can’t hide from me. Now lick it clean, you dirty girl.”
Her cheeks turn bright red as she puts the finger in her mouth and sucks.
“Good girl,” I say. “Now insert that toy and be a good girl for the rest of the ride.”
I let her wait until we’re on a highway in a relatively remote area.
“Aren’t you glad I let you wait until we were out of the city?” I say.
She rolls her eyes. “Oh wow, yeah. What a privilege.”
“Are you trying to get me to pull over right now and punish you on the side of the road?” I ask. “Because I will, if you roll your eyes one more time.”
She smirks.
“Don’t push it,” I say.
She slips her pants down and tries to rub the lube in. She’s squirming, trying to maneuver. Obviously, it’s difficult in a car.
“Do you want help?” I ask.
“No,” she mumbles.
“Fine,” I say. “Have it your way.”
After a few more minutes of struggling, she sighs.
“Fine.”
“Fine what?” I ask.
“Fine, you can help me,” she grumbles.
“Can help you?”
She looks at me.
“No, no, no,” I say. “I want you to ask me. In fact, beg me to help you.”
She rolls her eyes.
“Oh, there we go. Rolling your eyes again. You know what that means,” I say.
I spot a place to pull off the side, and I do. As soon as I do, I say, “Turn to me. On your knees.”
She swivels in the car seat, shifts onto her knees, and I pull down her pants. Cars are whizzing by us. If anyone saw, they’d see her thong-clad ass up in the air.
“Quick,” she says.
“You wish sweetheart. No, I’m going to take my sweet time here.”
I cup her perfect ass cheeks and slowly peel down her thong.
“Hurry,” she says.
“Oh, hurry, you said? Wait, I didn’t hear you. Can you say that again?”
“Oh my God. Are you fucking serious?” she says. “I’ll just do it myself.”
She reaches to grab the plug, but I grab her wrist. She turns, and we’re locked for a second, me grabbing her wrists, looking into her eyes. For a second, I feel like I can’t breathe.
Then I release her. I spin her around, push her neck down so that she’s kneeling.
“Quiet,” I say, “or I’ll spank you right here, right now. And you know I will.”
She’s quiet. She knows I mean it.
I grab the lube, squirt it, and liberally spread it around her asshole.
I can just imagine how embarrassed she is, which makes me relish this all the more.
Then I take the toy and slowly insert it into her, watching her squirm as it expands.
I got a medium-large size. Just big enough to be slightly uncomfortable without hurting too much.
I want her to feel it, to be constantly reminded of what a bad girl she’s been.
I take a second longer than I need to, then pull up her panties. She sits back down and does up her seatbelt.
“What do you think you’re doing?” I ask.
She looks at me. “What do you mean? We’re done.”
I laugh. “Oh, no we’re not. Have you forgotten about how you rolled your eyes after I explicitly told you what would happen if you did?”
Her eyes open wide as it dawns on her.
“You know I don’t joke about things like that,” I say. “I mean, if I did, you wouldn’t take me seriously. In fact, I’m doing you a service by following through on my word here. I’m teaching you that your actions have consequences.”
She rolls her eyes again.
“Oh, what, now I’m supposed to thank you for what you’re about to do?”
I laugh. “Oh, there you are, rolling your eyes again. Wow. You’re in a bratty mood today, aren’t you?”
I pull her face towards me and stick my thumb inside her mouth.
“You won’t be for long,” I say. “Now out.”
She undoes her seatbelt and grumbles as she gets out of the car.
“Hands on the side of the car,” I say. “Now, I don’t want to hear a peep out of you or I’ll punish you on the other side of the car, so everyone driving by can see you getting spanked. Got it?”
Her eyes widen in horror. “You wouldn’t.”
“Oh, you know I would. Ass out.”
She bends.
“More,” I say. “More.”
She bends even more, until she’s almost at ninety degrees.
“Good girl,” I say. “Now, I would normally just spank you like this. But there’s two things we have to deal with here. You were late. And you rolled your eyes twice. So I think that warrants a bare-bottom punishment. Don’t you think?”
“No,” she grumbles.
“Oh, but you know it does, don’t you, baby girl? Do you want to do the honors, or should I?”
“You do it,” she mumbles.
I roll down her black leggings and thong. I grab her cheeks and spread them for a second, marveling at the green glint.
“This is so much more fun with that pretty little toy in your behind,” I say. “Alright. How many do you think you deserve?”
“One,” she says.
“Twenty,” I say.
“Twenty,” she exclaims.
I just smile.
I want her to get nervous as she waits. I bet she’s wondering what I’m about to use. In fact, I haven’t quite decided myself. And then it hits me.
“Stay like that. I’ll be back soon,” I say.
I wander into the woods alongside the road and look for a branch. Once I find one that’s smooth and won’t snag, I grab it. I’m not going to hit her hard, because I don’t want to break her skin. Just give her a few quick stings.
I come back with the branch.
“Alright, sweetheart. I’m actually going to give you ten. These will be sharp and stingy. Are you ready?”
“Yes,” she mumbles. “Okay.”
“And I want you to thank me after each,” I add.
I can almost imagine her rolling her eyes.
I hit her right cheek. “Thank you,” she mumbles.
“Good girl,” I say.
I hit the other cheek. “Thank you.”
I hit the third and watch her pale, creamy skin redden. She’s so fucking beautiful. It almost hurts sometimes.
“Thank you.”
I keep landing them. Not enough to hurt her, just to embarrass her slightly and make her uncomfortable for the next few hours. When I’m done, I throw the stick away.
“You can pull up your pants and get back in the car now,” I say.
She does as I say, and I walk to her, cupping her face in my hands. As angry as I still am at her for her betrayal, I can’t help that she turns me on. Tanning her ass like that just made me want her more. It takes everything in me not to pull down her pants and bury my cock in her right now.
I need to be composed. So instead, I climb back into the car, turn it on, and drive the rest of the way in silence.