Embarrassed delivery driver

For a few months during college, I worked as a delivery driver for a local pizza restaurant to make some extra money. The job was generally pretty relaxing--I got to keep to myself and just drive around for most of the evening. I even got to listen to my own music and wear comfy clothes.

We had a "30-minutes guarantee" policy, which means if I don't deliver within 30 minutes, then they get the pizza for free. This usually isn't an issue, but on the rare occasion I do get there late I get a pretty relentless telling-off from my boss. I hadn't made that mistake for a few months, but last weekend there was a large local sporting event and we were getting tons of orders. The kitchen was backed up, and traffic was horrible, so we were running behind across the board. I got assigned a delivery to a fraternity house on the college campus I studied at. This was great, actually, since it was only about 10 minutes away and I knew my way around the area pretty well.

Unfortunately, the traffic was worse than I expected. What should have been a 10 minute drive turned into almost 20. In addition to the delays in the kitchen, this meant I arrived at their house with just a minute or two to spare. As I got closer, the sound of music and rowdy laughter grew. I hurriedly stepped up to the front door and knocked, pizzas balanced along one arm, and announced myself:

"Delivery!", I yelled, multiple pizza boxes filling both my hands. After a few seconds of waiting, I heard a pair of footsteps approach the door. The door flung open revealing two 20-something year old students, dressed casually and seemingly tipsy. "Your total comes to $45.96," I squeaked out, lifting my face to make it visible over the stack of pizza boxes. The first boy reached for his wallet before the other boy stops him.

"Woah woah bro, hasn't it been more than 30 minutes? That means you totally owe us those pizzas for free dude," he stated confidently. The first student began to put his wallet back.

"Wow, bro you're right, hey we ain't paying for these," the first boy declared, now facing me directly. I rotate the pizzas enough to get a better view of their receipt.

"Umm, sorry gentlemen it says here the order was placed... 28 minutes ago. You're still gonna have to pay for these," I remarked timidly. Admittedly, both of these frat bros were much larger and stronger than me, and I was nervous they might respond with force if provoked.

"That's **!", shouted the second student aggressively. I winced a little. He brings up his phone and continues. "Look! The call was made 31 minutes ago! That means we aren't paying for this, punk!" He declares, shoving his phone in my face.

"W-well, you may have made the call 31 minutes ago, ummm... but we may have not placed the order until a few minutes after," I muttered nervously. "I-is it possible you spent a few minutes placing the order?"

"Ooohh, this geek wants to get smart with us!", asserted the first student, tauntingly. At this point a passing group of girls in a neighbouring sorority house had stopped to observe the altercation. Impishly, he wandered around behind me while the other boy stood at the doorway, staring at me with a wicked smirk.

"Let's show this scum what we do to losers like this," announced the boy in the doorway. A few more boys in the fraternity house began gathering at the door to see what the commotion was about. Immediately, I cowered in fear, closing my eyes and thinking of all the ways they could inflict pain on me. However, after about two seconds, I was greeted with something far worse.

I felt a swoop below my waist, and the cool air reach my legs. A sickening feeling churned in my stomach. Frozen in shock, I quickly realized what had happened. The student who made his way behind had not intended to hurt me, only to humiliate me by pantsing me while my hands were full. Both frat bros, as well as the small audience in the doorway roared with laughter as my pants settled at my ankles.

"Check out the briefs on this geek!", exclaimed the student loudly, who had yanked my pants down. Anxiously, I peered down and was reminded with horror what pair of underwear I had chosen for today. I was greeted with the sight of some remarkably dorky briefs: tighty-whities with a heart print pattern. My nerdy briefs were tight, clinging to my body, leaving little to the imagination. I wanted to pull my pants back up, but I couldn't risk throwing the pizzas to the ground, as that might get me in more trouble with my boss than I already am. My only solution, I thought, was to squeeze my thighs together in an attempt to hide my bulge.

My face turned scarlet red in embarrassment as I stood there helplessly, the laughter growing louder. The group of sorority girls were keeled over, giggling with amusement. Both crowds cracked up further at my humiliating state, snapping pictures of me and my dorky heart-printed briefs. I stood there, mortified, hoping all of this could just disappear, when I felt another unpleasant sensation.

Without warning, I felt cotton shoot up through my ** crack, delivering a sharp, burning pain between my cheeks. It turns out the student behind me wasn’t satisfied with just pantsing me--he decided I also deserved to be wedgied relentlessly in front of everyone. With a single, forceful yank, my cotton briefs invaded my ** crack, lifting me onto my toes. The burning feeling engulfed my rear, distracting me briefly from the humiliation. Another wave of uproarious laughter swiftly, yet cruelly, let me remember the humiliating position I was in.

The boy yanked harder on my waistband, bouncing me softly as the threads of my tighty-whities began to pop. The fabric clasped my ** snugly, squeezing my package as my underwear was thrusted higher and higher. An agonizing pain burned vigorously throughout my groin and **, forcing a small whimper of pain out of me. The sensation was harsh and uncomfortable, and my ** crack was almost as hot as my face, now beet red with embarrassment.

He tugged my waistband once more, and I let out a pained gasp as he raised me a few inches off the ground. My pants now fell completely off my legs, sitting unattended on the ground. At this point the scorching pain in my ** crack was too much to handle, and I dropped the pizzas from my hands, using my now free hands to hold my crammed bulge, losing room with each second. The backside of my briefs almost completely disappeared between the soft cheeks of my **, leaving my ** nearly entirely exposed.

Abruptly, I was released from my excruciating hanging wedgie, falling to the ground to my hands and knees. The boy who administered my humiliation gave me a quick slap to my ** before grabbing the dropped boxes of pizza, along with my pants. He rushed inside, laughing excitedly with his newfound spoils. The remaining frat bros closed the door behind him, cheering and giggling at my dismay, while the group of sorority girls began to giddily disperse, but not before taking a few last photos.

Defeated, humiliated and in pain, I took a few seconds to collect myself. It was now that the realization hit that I was no longer in possession of the pants I had arrived in. While still covering my **, I picked my stretched briefs out of my ** crack and stood up. I hurriedly made my way to my car, using my shirt to shield my tighty-whities from anyone left still watching my pathetic display. When I finally sat down in my car, I wiped the tears from my eyes and decided right then and there to quit. Whatever reprimand I would face from my boss was not worth the poor wage I was making.

As if it couldn't get worse, I was still also a student at this school, and on rare occasions would see some of my tormenters from that day. I would be pantsed while walking between classes numerous times throughout my degree, always drawing laughter with my dorky briefs. The humiliation eventually subsided near the end of my degree but I can still remember walking to class on high alert for a few years just in case.