Roommate Romance

Flashback: First Wedgie

Kayla at the time was 6 years old, and Matt was 8. During the summers, they spent nearly every second of daylight playing together outside with the other neighborhood kids. This was a time before smartphones after all, so the two forms of entertainment for kids not on vacation are finding something to watch on tv, or playing outside.

Kayla was over at Matt's house as they all played in the backyard. She occupied herself picking dandelions from the yard as Matt and another boy from the street were kicking around a soccer ball.

It was a hot day, so both of the boys were shirtless with basketball shorts on, and Kayla was wearing a pink tank top with matching denim shorts.

Matt and his friend, Bradley, take a break from passing the ball and sit on the patio chairs.

"I was at my aunts house this weekend, and you won't believe what happened." Bradley says.

"Oh? What happened?" Matt replied, trying to bounce the soccer ball.

"Well, I was playing with my cousins in the basement, and my older cousin Ryan gave his brother a wedgie! It was so funny!" He says laughing.

Matt laughs. "Really? What a dork!"

Bradley laughs and looks at Matt. "Have you ever given a wedgie before?"

Matt shakes his head. "I don't have siblings, and all my cousins live out of town. Never had an opportunity to. Have you?"

Bradley nods. "I've given my cousin a wedgie one time. And I've gotten wedgied a few times by the two of them. It's embarrassing, but fun to give them!"

Matt chuckles. "Man, I wish I was able to give a wedgie."

They both look over at Kayla, on her knees in the yard still picking dandelions. "I dare you to give Kayla a wedgie." Bradley says.

"What? Wouldn't that be mean? What do I get out of it?"

"Well, obviously the fun of giving a wedgie for the first time!"

"Yeah but, what if she gets mad at me?"

"What if I gave you $2?"

Matt thinks. He would like to have $2. "Okay deal. But how do I do it?"

Bradley stands up. "You just gotta sneak behind her, pull back her pants and find her underwear, like this." He demonstrates by reaching into the back of his shorts, showing the back of his fruit of the loom waistband. "And you pull as hard as you can!"

Matt smiles. "Well your underwear is already out, why don't I just give you a wedgie?"

Bradley gives him a mean look, adjusting his shorts to cover his underwear and tightens his drawstring. "If you try, I'll punch you so hard in the balls."

Matt laughs. "Okay okay. I'll try it. Wish me luck."

Bradley sits back down as Matt gets up. She starts to walk behind Kayla, who's paying no mind as she's picking flowers and singing a Taylor Swift song to herself. Matt can already see her shirt is slightly raised, the purple waistband of her underwear sticking out ever so slightly. "Perfect" he thinks to himself.

He creeps up closer, grabbing the back of her shorts and pulls them back.

Kayla notices her shorts being pulled on and turns around, but it's too late. Matt got a fist full of her panties, pulling them up hard. "EEEEE" Kayla cries out as she gets wedgied.

Both Matt and Bradley laugh, seeing her white panties with purple trim and Disney princess print being pulled up.

The force of the wedgie causes Kayla to fall forward, nearly face palming into the grass, only being saved by Matt yanking on her undies. "Owiiee! Let go!" She cries out in pain and embarrassment.

Matt lets go of her panties, snapping them against her back. "Haha you were right Brad! That was funny!" He starts walking back to the patio.

Kayla, laying face first in the grass and bottom up, starts to cry with embarrassment. "Waaahh! That wasn't funny!" She stands up, pulling her undies out of her bottom. "I'm going to tell on you."

Matt's eyes get wide and he rushes to her. "No no! Don't tell on me! I'm sorry!"

"No!" Kayla barks. "I'm telling! You hurt me!"

"No please don't tell!" Matt pleads. "Look, I'll let you give me a wedgie too. It'll be payback!"

Kayla sniffles, looking at him and up and Bradley who was still laughing on the patio. "I want to wedgie you both!"

Bradley quickly stops laughing. "What?! That's not fair! I didn't even do anything to you!"

"You're the one who told me to give her a wedgie! Just get it over with, you've gotten them before." Matt tells him.

Kayla nods her head. "Let me give you a wedgie or I'll tattle on both of you!"

Brad sighs. "Fine! Whatever!"

Kayla's crying quickly turns into giggling as she rushes to the patio, her panties not fully stuffed down her shorts. "You first!" She tells Brad.

Brad groans as he stands up. He turns his back to Kayla with his hands at his sides. "Just get it over with."

Kayla giggles. Her hands get a little grabby as she accidentally grabs Bradley's shorts and underwear pulling them back, getting full view of the moon.

"Hey! Don't look at my butt! Just grab my underwear and pull!" Bradley says, pulling his clothes free from her grip. He pulls his waistband out for Kayla to grab.

Kayla grabs his underwear with both hands, and pulls as high as she can, revealing that he's wearing tighty whities.

Bradley groans in embarrassment. "Fine! You wedgied me! Now it's Matt's turn!"

Matt is laughing at the sight of seeing Bradley get wedgied by a younger girl. "Hahaha okay fine fine." He turns his back, pulling his waistband out slightly.

Kayla releases Bradley's underwear and rushes to Matt. Bradley stuffs his underwear down his shorts as he watches Matt get a taste of his own medicine.

Kayla grabs Matt's fruit of the loom waistband with both hands, still super giggly and giddy. She quickly pulls them up, revealing the red fabric of his briefs.

Matt winces at the feeling of the wedgie, it being a pretty new experience for him. It felt uncomfortable, but not as bad as it could be since he's receiving it from a 6 year old.

Kayla laughs uncontrollably, beginning to repeatedly pull Matt's underwear up and down to wedgie him over and over.

Bradley laughs. "Nice butt crack Matt!"

Matt blushes, reaching back to stop Kayla. "Okay okay that's good! You got your fun." He turns to face Kayla, stuffing his underwear into his shorts. "I'm sorry I wedgied you by surprise Kayla."

She smiles. "It's okay! I got to give you a wedgie so we're even!"

They all laughed and joked about the experience they shared together, each being cautious of who they turn their back on to not receive more humiliation.

~~~~

Current day Kayla envisions this experience as she drifts off to sleep, a smile softly spread across her face as she remembers the embarrassing, yet fun experience she got to have with her friends.