Wedgies Upon Wedgies

Jackson's wedgie

For Jackson, today was not expected to be anything interesting. There was not much to do this weekend and it wasn't like he had plans to go out partying with peers. Jackson understands he's far from being part of any kind of popular clique ever since middle school. Constant bullying, wedgies, nutshots, and swirlies later, Jackson accepted that he would never part of any cool group. In all honesty, he was fine with that. Yet, he never expected to go through much of his youthful mishaps again because there was Drew.

Drew is a fairly handsome young man and now Jackson's roommate. They got along fairly well for the most part. It was not until one day that Drew happened to stumble upon Jackson's clean laundry. Piles of underwear were scattered all over Jackson's bed that Drew noticed all the assortment of undies this roommate had. Yet, none of them appeared to be boxers. They mostly ranged from tighty whities to other colorful briefs. It was humorous to Drew, and from that day, the wedgies started.

Jackson would never admit to Drew that he enjoys the underwear tearing from him. Yet, there seemed to be an unspoken notice that Jackson actually found pleasure in the wedgies and humiliation. In all fairness, Drew finds himself also finding it humorous. Tugging at a nerd's undies feels right and is a perfect laugh for him. Today ended being an unexpected day for Jackson. He actually did not expect to see Drew all day, as the other male was fairly social. So Jackson decided to take a nap in the middle of the day.

As he napped, he did not hear Drew walk in through the door. The first thing that catches Drew's eyes is the band of the underwear sticking out just slightly from Jackson's pants. However, what really catches Drew's attention is the pattern just barely poking out. Butterflies. How pathetic. No real man would ever wear something so ridiculous. It only makes it more tempting for Drew to reach forward and yank those underwear right off. In fact, he does so. Drew's cool hands run just the edge of Jackson's back. It happens far too quick that by the time Jackson can even wake up, the green underwear shoots up his ass without any mercy. The familiar feeling of pain and embarrassment rushes through Jackson quickly. The minor laughter from Drew does not help him the slightest.

"What's this? Butterflies? Why would you wear this," Drew questions and keeps tugging at Jackson's underwear. Jackson by now is fully awake and aware of his surroundings. Though he still finds himself lost for words by the action. He forgot he was even wearing those underwear.

"They're comfortable," Jackson tries to explain with Drew still nearly holding him off the ground. His ass is pointed to the sky and the dangling from Drew's hands honestly half turns Jackson on. It makes his face start to turn into a flush of red as he starts to squirm in discomfort. Drew notices and yanks the underwear higher.

"Ah!" Jackson makes a minor face of pain from the pull. Drew grins and suddenly released Jackson's underwear and causes him to fall back on the bed. Before Jackson could do anything, he feels Drew yank harshly at his pants this time. His loose fitting jeans slide off completely. His stretched butterfly underwear are completely exposed to Drew now. Jackson fumbles to try and reach down and pick up his pants in shame. Drew is much faster though. He grabs Jackson's arms to prevent him picking up his own pants and uses his other hand to pull up Jackson's underwear higher. The underwear stretches far and causes him to land face first in his own bed. A sound of fabric starting to tear can be heard. He starts to feel his underwear still riding all the way to his shoulder blades.

Jackson is slightly grateful as he could kind of hide his face in shame. "Stop. Please," Jackson tries to call through the folds of his bed sheets. Drew rolls his eyes at the comment and continues to keep pulling at Jackson's undies. He purposely keeps them high to keep Jackson from doing much else other than to just accept the nut crushing pain. Drew gets a clear view of Jackson's butt as it remains pointed upwards. Drew laughs at the sight and quickly pulls out his cellphone to take a few quick pictures. After satisfied with the many photos, Drew returns to yanking at Jackson's underwear to the back of Jackson's neck. The sound of ripping continues once more. Drew does not show mercy and in fact Jackson is more than sure that he started pulling even harder as the burning sensation cuts through his balls and penis. He can only pray now that they would drop again in the near future. The band is nearly ripped from the rest of his underwear as Drew grabs Jackson's hair and forces his head back. It is just enough for Drew to attach the torn green undies to the edge of Jackson's head. It is painful to say the least and way too humiliating for him. Drew laughs for a few minutes at Jackson's awkward position until he decides to show mercy and releases Jackson from the atomic wedgie.

There is a quick sense of relief at the thought this being all done and over with. Jackson lays there, dazed with his underwear completely bunches up at his hips. His pants still remain off of him with his ass still completely showing off to the world. He hears Drew shuffling around the room and he turns his head slightly to see what the other man is doing. Drew pulls open Jackson's underwear drawer and casually glances inside with far too many colorful underwears lay. Everything from tighty whities to childish briefs. There is that almost sinister grin on Drew's face as he picks up a random brightly colored pair of briefs. "Oh, you thought we were finished? Oh, no! We're just getting started buddy."

As quick as the relief came, it left for Jackson. "Wha-?"

Drew tosses a pair to Jackson, cutting him off. "I said we are just getting started. Now put those on. Now. I don't like to be kept waiting."