Connor stared at the pull-up in his duffle bag, his heart pounding. Eighteen years old and still needing protection at night - it was his most humiliating secret. But this was different. After dodging every sleepover invite for years, he couldn't skip this last summer night before college.

The moment felt so unreal - the scratchy carpet of Dave's office against my back, his weight on top of me, both of us stripped down to just our briefs. His chest hair tickled my nipples as he ground against me, that perfect dad bod radiating heat.

I'm dreaming of a tight and white Christmas 🎶

Masterpost for the stories I've written.
All are linked with hashtags in the replies 🧵

I can barely breathe with Joel behind me, my heart pounding as I strain behind me for his kisses. My briefs already feel damp where my cock presses up inside them, desperate for his touch.

"Pin me if you can!" Travis taunted, a dangerous glint in his eye. We'd been hanging out in the dorm lounge when Travis and I started horsing around. Before long, it turned into a full-on wrestling match. Our friends formed a circle, cheering and laughing as we grappled on the carpet.

This little story heavily inspired by my office... err, bluesky crush @tryundies.bsky.social

Every time Dave bent down to get something from the bottom drawer, that little strip of white elastic would peek out above his khakis. It was driving me absolutely fucking insane having to sit across from him all day, pretending I wasn't obsessing over what was underneath his clothes.

Tim's heart stopped when he felt the soft, rectangular package in his lap - that unmistakable department store underwear box shape. Around him, six male cousins watched eagerly, already snickering. He prayed he was wrong about what was inside.

Jake shifted uncomfortably at his buddy Mike's barbecue while the guys reminisced on their teen years. The sun beat down as the group lounged around the pool, slugging beers, and sharing stories.

"Remember how Jake ALWAYS wore tighty whities? He made it all the way to graduation in those things!"

"Alright, Truth or Dare?" Jake leaned forward, his eyes glinting mischievously at the host, Matt, who was sitting cross-legged on the floor of his finished basement.

Matt shifted uncomfortably under the stares of his four friends. "Truth, I guess."