Caught Wearing My Roommate's Shoes and Secrets in Her Trunk

It was a Friday evening. My roommate Diana had just headed over to her parents’ place, leaving me all by myself in the house. We are both students sharing this home. The property belonged to my folks; it was their old house that they hadn’t managed to sell yet. Diana and I paid rent to them so we could live there.

Naturally, when Diana went out, I did what I always do: I went into the laundry room to search for one of her thongs. I took off my jeans and underwear and slipped on a pair of red thongs. It might seem odd for a guy, but girl’s underwear have always had an appeal to me. They just look sexier than men’s versions somehow. Since Diana was living with me, it gave me the chance to try them out.

Next, I went downstairs into the hallway and checked out the shoes. Alongside her lingerie drawer, women in high heels also get my attention. Diana owned a few pairs of heels, though none were extremely tall—none taller than 3 inches. I selected some red pumps and put them on. Diana is only an inch shorter than me, and we wear the same shoe size, so they fit without issue.

I sat on the couch watching TV. It had been a hot day, so I decided to open some windows. I walked into my bedroom and opened mine first, feeling the fresh evening air against my skin. Then I went to Diana’s room and opened her window too. As I turned to leave, I spotted her large trunk again. I’d always wondered what was inside because she kept it locked.

That seemed odd this time. I walked over for a closer look and noticed it wasn’t latched shut. She must have forgotten to lock it.

Being curious by nature, I opened the lid. Inside were just some clothes, nothing particularly special at first glance. I wondered why she kept it locked then. Then I realized I could see down into the bottom already, even though there didn’t seem to be much left in there after removing the top layer of clothing. It turned out there was a false floor underneath. I lifted that panel aside and peered inside.

I was amazed by what lay beneath: latex dresses, some handcuffs, a ball on a strap, ropes, and several pairs of very high heels. I picked up some items. I never knew Diana had such an interest in these kinds of fetish gear. She’d kept everything well hidden. A bit guilty about discovering her secret, but intrigued too—perhaps even aroused by finding out without her knowing.

So she liked bondage stuff. I wondered what it felt like to wear them myself. I picked up a small box and opened it to find lots of keys, likely for the various items from the trunk. Then I held the ball gag in my hands, wondering if I should put it on myself. Oh, forget about cleaning it later—I’ll deal with that later. I placed the ball in my mouth and fastened the strap behind my head. My mouth was wide open due to the ball size. I tried speaking but realized I couldn’t get any words out clearly.

Then I moved toward one of the high heels, picking it up to examine it closely. These were black with what looked like a 5-inch heel. They featured ankle straps secured by double padlocks, which allowed them to be locked shut. The locks themselves hung open on the shoes; their keys weren’t inside the locks but stored in that small box.

Feeling quite turned on by these sexy shoes, I took off my red pumps and slipped into the 5-inch heels instead. I clicked the padlocks closed so the ankle straps wouldn’t dangle loosely. Trying to stand up, I noticed how much more difficult it became balancing in them. Walking a few steps proved challenging as well.

After a short while, I decided to take off the shoes since walking was becoming cumbersome. Grabbing the keys from the small box, I started trying them one by one into the padlocks on my feet. But none of them fit correctly! That was strange—surely one must work? I tried again slowly, but a nagging doubt began growing in my stomach. The correct keys for the shoe padlocks weren’t actually inside that little box!

My mind raced: Where could they be?

Just then, I heard the front door open and my heart skipped several beats—Diana was back already! “Hello!” her voice called out.

I pondered what to do next when I remembered I still had the ball gag in place. Panicking slightly as footsteps came up the stairs, I attempted to pull it free just before she entered the room.

Before I could fully remove the gag, Diana walked in. Instead of looking shocked or surprised, an evil grin spread across her face. “Ha! I knew you’d be caught wearing my shoes,” she said. “I set this trap specifically for that moment. Knowing your curiosity, I left the trunk open expecting exactly this outcome—a gamble that you’d put on the heels and lock them without checking if the keys were inside—and it paid off!”,

She paused. “Now… what shall we do with you?”

I sat there frozen, staring at her…