Your dom had never taken things this far before. It was kind of terrifying, and it was kind of hot. He picked you up promptly at 5pm, but before taking you out he made you strip off your pants, your shirt, hell even your socks and shoes. He left you nothing but the tight little underwear he had been making you wear for months and told you to get your ass in the car. You felt his hand slap against your brief covered ass as you got into the passenger seat. He buckled you in and brushed his hand against your crotch as he let go of the seat belt. You were already hard just from being in public in your whities and he smiled knowingly. “Where are we going?”

“Don’t worry about it.”

You gulped in anticipation as your dick twitched giving a reaction of its own. At the traffic light you could feel his eyes on you and soon after his hand pulled up the back of your undies into a solid wedgie.

“Keep it in.”

You obeyed. He pulled over at your old high school. You hadn’t seen the building in nearly a decade and felt thankful it was in a more secluded location of the town.

“You always told me you regret how you never got to be treated like a nerd in high school.” He smirked. “Time to remedy that.”

You didn’t know how he had managed to get access to the building on a Saturday, let alone during the summer, but he pulled out a key as you approached the main door and let the two of you in.

“Where’s the locker room?” He asked. And for once he let you lead the way.

He opened the door and you stepped through excited to see where this would go. He gave no instruction or indication on what was going to happen, but he had you go over to your old gym locker and your excitement grew. You sat down on the bench waiting as he left you to stew for a couple of minutes while he went to “get ready” whatever that had meant. A few minutes passed and you saw him step into the row of lockers in full football gear and your dick sprang to attention.

“Oh my god. I can’t believe you still wear tighty whities. Does your mom buy them for you, dork.”

You face flushed as you tried to think of a line to respond with. “Why are you staring at my underwear? What are you gay?”

He smiled, maybe he hadn’t expected that response and couldn’t help but let the playfulness of it show on his face, but he recovered quickly and got back in character. “Don’t talk back, nerd or this is going to be a whole lot worse. I see your butt’s hungry since you already have a natural wedgie going.”

You had forgotten you still had the wedgie in place, but a retort came easily. “Or maybe one of the other jocks already beat you to it. As you can see I’ve already had my daily dosage of wedgies so you can run along and find another nerd to torture.”

“Well they didn’t do a very good job if that’s the case. Those tighties still look rather white and pristine and I don’t see any rips anywhere. If it was one of my boys I may have to give him a wedgie just to show him how he should really be doing it.” He grabbed a hold of the leg holes and pulled.

You groaned in a mixture of pain and pleasure. “You call that a wedgie.” You taunted. “I’ve woken up from with worse wedgies just from tossing and turning in bed.”

“Is that so?” He asked as he pulled harder. “Maybe your thick ass just knows how bad you crave the feeling of cotton lodged up there?”

You tried to respond, but all that came out was a cry of delight as he pulled again even harder this time.

“You like this nerd? You some kind of queer who gets off on this shit?” He pulled even harder as you both heard some tearing start and he smacked your exposed ass cheeks with his free hand. “Tell me you want this. Tell me you need to feel your own underwear lodged up your ass just to get that little dick of yours to squirt out some release?” He moved his other hand onto your whities and adjusted them both so they were grabbing the thin strand that would normally be seated underneath you if the wedgie hadn’t pulled your underwear so far out of place. “Well...” he waited.

“Please, Mr. football captain. I need the feeling of my tighty whities pulled so hard up my ass it makes me cry out in ecstasy and relief as I release some hot sticky cum all over my underwear.”

“I thought as much.” He gave one last pull as your whities ripped and you creamed the front of your briefs, as promised.