Caught by the Drawer Pt. 01

"WHOA!! What do we have here?"

I was so fucked. And not even as fucked as I was going to be.

There I was, caught frozen between the vanity mirror and the door to my bedroom, dressed from head to toe as "Meaghan". I had donned my favorite 4-inch heels with a pair of pantyhose. My little red dress was stretched to new limits over my freshly purchased breast plate. I was just putting the finishing touches on my make up with my blonde wig already on when I heard the keys in the apartment door. If it weren't for my dress catching the handle of a drawer, I would have been back in my room with ease. But instead, I had been caught frozen, within an arm's length of the safety of my bedroom, as Jack stood in the entrance into the hallway, eyes wide.

Jack was a wide receiver for our university's football team, and he was supposed to be out of town for the night. He had told me earlier that week that he was going to be visiting his girlfriend at her school a couple hours away, and from that moment on, I had been planning a fun evening for myself.

That was really the only thing I had in common with Jack; when we first met, we discovered we were both in long distance relationships with our girlfriends. He always joked that some night when we were lonely, we would go to a strip club together and have a guys' night, but that was about the extent of our proposed time together. Occasionally we'd see each other at the gym, but we were rarely doing the same thing. I spent most of my time in the squat rack and on the step machine while he and his buddies used all the plates they could find for the bench press.

Rather than address his initial question, I stammered out, "I thought you were going to your girlfriend's tonight."

"Yeah, I was supposed to, but she cancelled," he shrugged it off as he slid a step closer to me.

"What's this all about?" he asked again, gesturing to me and my make-up strewn across the counter.

I responded with the only thing I could think of that might be socially acceptable, "Oh, it's just a hobby. I've been thinking about picking up drag," my voice fast, but surprisingly confident for the circumstances.

"Drag? Really?" he cocked his head, looking me up and down, trying to decide if my appearance could justify such a response.

"Well, you look great. Like really great. I actually thought you might have been your girlfriend when I came in, but she doesn't even look this good."

I suppose I should have been offended by that, but instead I could feel my tucked cock twitch at the compliment.

He took another step down the hallway, this time placing himself slightly between myself and the bedroom door,

"Does your girlfriend know about this?" he asked inquisitively.

"No, not at all. I would be horrified," I replied, honestly, but maybe too honestly.

"Horrified? Why? Are you worried she might realize her boyfriend is prettier than she is?" he teased, brushing one of the blonde strands of hair away from my face. I'd never experienced anything like that before, I could feel my face rapidly growing red.

"Or..." he continued, his voice dropping to a whisper as he leaned in closer to me, "are you worried she might realize her boyfriend is just a sissy who would rather spend Saturday night at home playing with himself than go see her?"

"Whoa, now, watch it!" I swatted his lingering hand away from my face and took a step backwards, my butt now up against the vanity counter. "I told you, I'm only doing this because I think it might be fun to try doing drag! That's all this is."

"Riiiight," he said as he rolled his eyes, "'Drag'. You know, most guys I know that do 'drag' are pretty outgoing. They like being the center of attention, that's kind of their thing. And they sure as hell wouldn't be terrified about someone finding out about it."

I didn't know what else to say. I guess what he said was probably true, but I didn't really know much about drag, and I never had any expectation of performing in a show. The only thing I had planned was getting dressed up, snapping a few photos, and I would go from there. At this point, anything would have been better than what I was doing in that moment.

I had to say something though.

"Well, maybe that would just make me different from other drag queens. And maybe I don't want to do it anyway! Can you just move so I can go to my room please?" I tried to skirt by him.

"Hang on," he stepped in front of me, a wry smile creeping onto the corner of his lips, "why go away so soon? I feel like I'm just now getting to meet my roommate for the first time."

I tried again, growing impatient, "Now you've met me, so can you please move?" practically pleading with him at this point.

He sighed, the smile still on his face, "I guess. It's a shame though..." he stepped to the side so I could move past into my room. As I went to slink by his hand came down and smacked my ass, grabbing all that he could, "I've always wondered what that ass would look like in the right outfit. And it feels great too! Nice and tight!" he laughed as I smacked his hand away again and slammed the door.

I could hear Jack laughing to himself as he started down the hallway. Alone in my room, I was so rattled I could barely think. I was wishing I had those clothes off and the makeup off my face and that I was a thousand miles away. How could I have been so stupid to not make sure he was going to be gone? Why didn't I double-check with him that morning? Why did my dress have to get caught on that drawer? AGGGH. Was Jack going to tell anyone about what he'd seen? Oh my gosh, what if he told my girlfriend Alyssa? She'd be done with me for certain. He wouldn't tell her though. He's barely said two words to her in his life. Surely he wouldn't start up his first conversation with her to share this experience.

I felt something drip down onto the top of my foot; it was pre-cum leaking from my tucked and rock-hard cock, bound up under my thong and panty-hose. For all my embarrassment and shame in that moment, I was hornier than I'd ever been.

As I gazed down at my dripping cock, I heard Jack open his door and his footsteps move down the hallway. In my mind, all of my thoughts were begging him to move past my room and to somehow forget the last 5 minutes of his existence, but I heard him stop just outside.

He knocked and cracked the door.

"Listen, I know you're embarrassed and I didn't mean to startle you," he began, his voice softer, but ominous, "but you know, I don't think that girlfriend of yours, Ally? Alyssa? Whatever her name is, would want to find out about all of this. And you and I, we both have needs...I think we could work something out. I'll be in my room if you'd like to figure out an arrangement to make sure everyone's happy..." his voice trailed off. He lingered for a moment, and softly closed my door.

I stood there in my room, staring into space, completed dumbstruck at my situation. Not ten minutes ago I was having the perfect Saturday night, and now there I was living a sissy-infused nightmare. I could try to convince Alyssa that Jack was making things up, but why would he do that? And if I came clean to Alyssa, she'd probably dump me. Yes, she was a pretty-open minded person, but she'd told me before that she generally prefers a more "masculine" guy, and I would have to believe my "sissy side" would be a deal-breaker. No, there was no good scenario in which she found out about this.

I'd have to figure out an arrangement with Jack, but what would that even mean? Maybe Jack would just want me to clean the apartment for a little while. Or maybe a bribe? I had some cash I could pay him. But he said, "we both have needs". Why is he worried about my needs right now?

What I really needed was some dirt on him, something that would give me some leverage over him and his girlfriend. A mutual assured destruction scenario, his secret vs. my secret. Maybe he's had a girl over and she's left something behind? I don't know, I'm sure I could find something.

I was about to walk out the door when a thought stopped me: Shouldn't I change my clothes? I mean, I'd probably feel a lot better negotiating this "deal" if I wasn't dressed like a sorority girl at the club. But then I realized, he's already seen me like this, so what difference does it make? And if he really thinks I'm going to come see him to "work something out", he might be trying to pick his room up. If that's the case, the sooner I get there, the better my chances of coming across something he wouldn't want me to see.

I opened my door and stepped up to the vanity mirror. My hair was a little out of sorts, but with a touch here and there, we were back to brand new. I was loving the cherry red lip-stick to go with the bright red-dress. Combined with the boobs, it really made for that perfect brainless-bimbo look. And hopefully, that's all Jack would assume that I was while I cased his room for the perfect thing to get me out of this mess.

Ready to go, I turned from the mirror and walked to his door...