Prank the Boss

2.5K 16 1
                                    

Part 1

I can remember it like it was yesterday, it was my first day at my new job. I had just graduated from college a few months ago and was lucky enough to get hired on the spot. The job was to oversee and supervise the workers at Norman's Tighty Whitie emporium. I couldn't wait to begin! I love Tighty whites and the way they just hug your body in all the right ways, but I didn't let anyone know that. If anyone would have found out I would have been branded as a nerd and probably got wedgied. I was too buff and popular for something like that to happen, so I kept it my little secret.

The day had arrived for me to meet my team and start the best days of my life. I had to make sure I looked amazing, so I wore my tight black dress pants that showed off my ass and muscular thighs nicely. On top of that I wore a nice grey shirt that showed off my defined chest very nicely and my black blazer. Underneath my pants I wore my lucky Tighty whities. I wore them for all big occasions. I've had them for at least 4.5 years now. They have seen better days, but a few little holes and terrible elastic won't stop them from being lucky.

When I arrived at norman's, I couldn't believe I was chosen to supervise this mega store. As I strolled in the door, I noticed a couple of the workers didn't look too friendly. A big tall lanky guy was vacuuming and staring me up and down. I tired to avoid his gaze, so I turned to look in the opposite direction, that's when I noticed a few sales associates staring at me. It was majorly creepy, but I kept going until I met Norman himself. He called an all store meeting and introduced me to the staff. It wasn't the warmest of welcomes, but I was still excited to work in a Tighty whities store. I had a huge employee discount that I was going to take advantage of.

The first couple of weeks were fine and the employees still didn't seem to like me very much, especially because I didn't take any of their excuses and actually made them work. One day while I was looking through storage for some rejected and old Tighty whitie models for my collection I felt two big hands grab my underwear and yank them up. I was shocked and confused, while being dangled off of the ground. I struggled to get free, but it only made the wedgie go deeper up my ass. I warned whoever it was to let me go or I'd kick their ass and have them fired. I heard him and what sounded like two others laugh.

I was swung around and bounced up and down for what seemed like hours. My ass was so sore and my balls felt like they had been pushed back inside of me. I thought it would never end, but they dropped me on the ground.  I fell on my stomach and immediately grabbed my poor ass cheeks. I heard some clicking noises, like a phone taking pictures and was about to turn around to see who the jerk was that ripped me a new asshole. Before I was able to I see, two sets of hands flew over my head and brought my Tighty whites with them. They hooked them under my chin and locked me in place. I couldn't help but yelp at the sudden pain from the atomic. More pictures were taken and I heard more laughing.

Each of the guys spanked my ass as hard as they could before leaving me there bound in an atomic. I eventually regained my strength and released my ripped Tighty whities from my head. They were so stretched out and torn badly now. I stuffed them into my pants and pulled out the wedgie before heading back to my office. When got back there was an email with an attachment. When I opened it, there were tons of pictures and a couple videos of me getting wedgied from earlier. Underneath was a message saying, beware the Tighty whitie bandits, do as we say and your undies will live to see another day. What have I gotten myself into?

To be continued...

You've reached the end of published parts.

⏰ Last updated: Oct 28, 2020 ⏰

Add this story to your Library to get notified about new parts!

Toms New Job at the Tighty Whities Emporium Where stories live. Discover now