Caught Cross Dressing

As Friday afternoon rolled around, my heart started to race. My roommate, Mark, was headed out of town for the weekend and I'd finally have the apartment to myself. I mean, don't get me wrong, Mark is a great guy, but we spend a lot of time together - we live together, we work together, we commute to work together, we get drinks after work together - it's just a lot. And everyone loves Mark, he's tall and well built, in his late twenties and already a senior manager. I guess I'm just lucky to hang around with the guy, and to live with him. Even my girlfriend , Kayla, always talks about how he's so handsome and funny.

Mark left mid-day and I could hardly wait for 5:00pm to roll around and head to the apartment. I had my night all planned out: I'd take a long hot bath, shave my legs, paint my toenails, and get all dressed up in my girlfriend's clothes. I hadn't had the chance to cross dress for many months and the thought of my night made me squirm inside. After getting all dolled up, id make myself a stiff drink. Then I'd jump online and get on cam and hopefully chat with some guys and play with myself till I passed out. I'd already told Kayla I wasn't feeling well and needed the night off, so my plans were locked in!

I left five minutes early and raced home. My hand was actually shaking as I unlocked the apartment door. I quickly poured myself a bourbon and slugged it down, feeling the warm liquid hit my belly relaxed me and I took a deep breath. I then went to my room, stripped off all my clothes and ran my bath. While the tub filled, I pulled out all my secret sissy stuff - my make up, two wigs, a black fishnet body suit, three pair of sky high strappy stilettos - I laid everything out on my bed. I then went to my dresser and pulled out one of Kayla's black lace thongs and matching bra and laid them on the bed. Feeling warmed by the bourbon, I got into the hot bath and proceeded to shave my legs, making them silky and smooth. I sighed as I ran my hands along my skin, feeling so happy to have my night alone to be the sissy cross dresser I am deep inside.

I hopped out of the tub, excited to shave my face. Kayla likes me to have a little stubble, but I didn't care and lathered up and shaved till my face was silky smooth. Next, I laid out my make up and gleefully applied my foundation, then added slutty blue eyeshadow and black eyeliner, with fire engine red lipstick and gloss. I smacked my lips to spread the lip gloss and smiled at myself in the mirror. Men had told me I was passable based on my photos, but I think they were just being nice.

I put on a long black wig and then Kayla's panties and bra; my tiny uncut cock stiffening as I padded the bra. I then put on a pair of black fishnet thigh highs and black patent open toe stilettos. My toenails were painted red to match my lipstick. I walked to the mirror, my heart pounding, to take a good look at myself. It was a wonder how much I transformed from a wimpy skinny Asian guy into a sexy sissy gurl. I smiled and then walked to the living room and grabbed my laptop.

I settled down on the couch, laying on my stomach, and cracked open my laptop. I logged into my favorite site and turned on my webcam, so excited to show off as my sissy self. It was a little slow, so I poured myself another bourbon. Then I got a message from a guy named MasterM; we flirted and he seemed very interested in me, I was quite flattered and showed him every inch of me on my webcam, teasing him and stroking my lil sissy clit. We exchanged email info and I soon got a message from him saying I would pay for being such a sissy slut tease, but I didn't think much of it. I played on cam for hours and hours with a bunch of guys watching me, until I finally came a huge load and sprayed cum all the way onto my own neck and chest... I fell into a drunken sleep quickly on the couch.

I woke the next morning on the couch, still dressed like a slut with my own dried cum all over me. I felt like such a sissy whore that I quickly stroked myself off again before stripping off my outfit and taking a hot shower. I texted Kayla to let her know I still wasn't feeling well, then I laid in bed naked and fell fast asleep. It was dark when I woke, and I couldn't help but get all dressed up again and play on cam... it was much of the same as the night before, but still thrilling to tease and show off for sissy admirers; I just felt so sexy in front of them, totally different than I feel as a 5'8" 140 pound asian male. I was disappointed to not hear from Master M, but still came hard and then licked it all off my fingers on cam. I then took a shot of vodka to wash down my cum, crawled into bed, and passed out.

I woke Sunday morning with a start. I was still dressed like a sissy cumslut and my sissy stuff seemed to be everywhere and my make up was all over the bathroom. It was already 10:00am and I knew Mark was coming home by noon.

I got to my feet and went to the kitchen to take a shot of vodka to calm my nerves. But to my absolute horror and disbelief, Mark was sitting at the kitchen counter, with an evil grin on his handsome face.

"Hi Sissy," he said casually, still grinning. "Take a look at this," he said, opening his laptop. I gasped as I saw two screens playing videos of myself dressed up from the past two nights. One of the views was a taken by a webcam; the other view was of me on the couch. I gasped for air and leaned on the counter, so dizzy and flush.

Mark poured me a shot and said, "cheer up sissy, this can be our little secret - and from now on, call me Master M."