[M4F] Everything my best friend's mom could ever need to blackmail me was now on her computer
TLDR: A guy sneaks into his crush's room during her son's party, plants files containing his own blackmail material onto her computer.
The air is warm, almost too warm as we celebrate Caleb, your son and my best friend for most of my life. We had always been inseparable during our time together, until my parents decided their perfect genius needed a better start and forced me to go to a stuffy private school. It did wonders for my grades, I even graduated early, but I would have rather spent those years with him, my best friend, and with you, my crush for years now. But as it always did, different schools meant less time together, and soon enough we were drifting apart. The one thing that never changed, however, was my feelings for you, Caleb's mother.
Having excused myself to use the bathroom, fueled by my first tastes of alcohol, I snuck back into your house. The laughs and happy voices from the party grew quieter as I ventured deeper, down a hall, up a staircase. Halfway up, I froze, questioning myself as I had countless times whether this was really a good idea. The little USB stick in my pocket felt like it was burning against my thigh as my pulse quickened. Closing my eyes, I took a couple deep breaths, remembering my favorite quote: "Life without risk is more bland than oatmeal." With steely resolve, I pushed through, making my way the last few steps until I saw your bedroom. The door was closed, of course, no one should be up here.
Each step made my heart beat harder. As I reached for the handle, the sounds of the party downstairs were all but gone, hidden behind the pounding of my own heart. Pushing down the handle and letting the door swing open, I was met with a wall of your scent. My knees went weak, and I had to reach for the door frame to keep from falling. Each subsequent breath breathed more and more strength into me, as you always have, until within half a minute I was back to full strength. I took a few careful steps to make sure my knees would hold my weight as I made my way inside your room, heading straight for your computer. Pulling the tiny USB from my pocket, my fingers trembled so badly it took me a second try to get it out. I prayed as I pushed it into your computer that you still had the same password as years ago. My hands shaking made it hard and time-consuming to type, but eventually I got it right. My heart skipped a beat as I pressed enter and it started to load. Each second before confirming the password was valid felt like a lifetime, but finally the computer screen lit up, I was in. A couple clicks of the mouse later, and the files I had prepared on the USB were on your computer. Pulling the USB from the computer, I swallowed as some sort of finality washed over me, calming my nerves for the first time in weeks. All the blackmail material on me was now on your computer.
With steps light as a feather, I walked around your bed and headed for your door, stopping mid-step as I saw your hamper. My pulse quickened again, back to thumping in my ears. Reaching out, I lifted the lid, revealing your dirty clothes. Leaning my head out the door, I tried to listen for anyone in the house, but all I could hear was my heart. I couldn't see anyone, and so with one final moment of bravery, I reached down and grabbed a pair of your panties. Telling myself it was a fair trade for all the blackmail you now had on me.
Posted Jun 8, 2026, 4:59 AM UTC