▲ 33 r/Sissy

Almost caught by roommate all dresses up

I live in a pretty small place with 2 other guys. Typically, guy #1 isn’t home all that often. He works for most of the day, and only comes home around night. We’ve only run into each other about handful of times, and exchanged quick conversation. Overall, I never worry about him when I’m having fun.

Guy #2 is the one that I’m more concerned with. He is usually at home 9/10 which is completely fine, but makes having sissy time more difficult. Because of this, I started planning my dress up times around guy #2 and hatched an idea. Once I would hear him leave and saw his car gone from my window, I would exit my room to prance around for a bit and take photos.

This all sounded like a good a plan, and before guy #2 left, I got everything I needed together. I put on a pink maid outfit, the petticoat, gloves that were hard to do anything with, and even some little cat ears that had bells on them. This was one of the first times wearing this new outfit, so I was feeling happy and a little giddy. With this confidence, I left my room once I heard my roommate leave. But although I felt like he was gone, I had the urge to check the living room window just to be sure. As I peeled back the blinds, I saw guy #1’s car parked in the driveway. Not only did I see his car, but I also heard his bedroom door click open.

Thankfully guy #1 lives in a room segmented from mine, so I was able to run away without bumping into him. But the big rustling petticoat, and the loud jingles of my ears did NOT do me any favors. It could have been worse though, I decided on wearing regular sandals instead of heels before I left my room, so no loud heel clicking was heard by him.

But one wrong move and I couldn’t have been completely outed. Be careful girls 😥

reddit.com
u/Deep_Direction9311 — 16 days ago