Chapter 5
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“Today’s the day!” is what I would have sat up and yelled, like an overzealous starfish, if I hadn’t been tragically sleep deprived by absolutely no fault of my own. By “no fault of my own” I mean, browsing weirdly relatable content on Twitter and Reddit until well past midnight. Luckily, for once I ended up not having any dreams. At least, not ones I wanted to think about. Definitely nothing about being on my knees, in a dress, while Lana gave a detailed demonstration of a high speed rail system. Nope, nothing of the sort. Just needed to get started with my day and try not to panic at the fact it was going to be my last day enduring the punishment. I was gonna try to make the most of it since there wouldn't be any more bets. Though first, I needed to finish the line work for a commission which was, and I quote, “A blood-soaked Furby, but make it sexy.”

I once again performed my Olympic feat of rolling out of bed and sluggishly putting clothes on. I paused, glaring at the fabric in my hand, realizing I had instinctively grabbed the skirt instead of my jeans. What was I doing? Sure, I had gotten in the habit of wearing it around the apartment, but it was weird how quickly I had grown accustomed to it. I reluctantly hung it back in my closet. I should probably just throw it away. I wasn’t going to need it anymore. That’s when the familiar feeling set in. Existential dread and I were no strangers, but just because you’ve experienced gut-wrenching agony before, doesn’t make it any less painful. Like eating at Taco Bell. 

I finished getting dressed and hauled my empty husk of a body into the kitchen to replenish my bloodstream with the elixir of life. And to get started on the cruel warping of a beloved kids’ toy turned sexual nightmare. But Lana was already up and…making food?

“Hey there, sleepyhead. I thought I was gonna have to call a search and rescue party to try and get you up.” Lana flipped something over in the pan on the stove.

I rubbed my eyes, still unsure of what I was looking at. “It’s not that late. It’s only…” I checked my phone. “Noon thirty. I just wanted to make sure I was rested for tonight.” 

Lana just giggled. She had been doing a lot of that lately. I set my tablet on the table and very carefully sat down. I was captivated by the other-worldly scene that was taking place in our kitchen. 

“Um, Lana? What are you doing?” I asked, intently listening to see what kind of alien, robot, or robot alien had body snatched my best friend. 

“What does it look like? I’m cooking,” she replied and slid what appeared to be a sandwich on a plate.

“Please, know I mean this in the least offensive way, but--you’re not exactly the best cook. So why?” I braced myself for the snappy comeback.

She sighed as she placed another sandwich in the pan. “I know. But I wanted to make you lunch as a way of saying thank you. Even if it’s just a shitty grilled cheese. I know how stressed you are and how hard you’ve been working. I just want to say I appreciate everything you’ve done and everything you do. I’m really happy to have you in my life and I couldn't ask for a better friend.” She set a plate down in front of me and smiled. 

I looked down at the somehow simultaneously burnt and undercooked grilled cheese on the plate, then back up at Lana, who was holding the spatula with a nervous look on her face. I fought back the welling tears as hard as I could. She was trying so hard, but I didn’t even know what I’d done for her to want to thank me. Maybe she was really nervous about tonight and was happy that I was coming along, maybe she was just thankful I accepted her for being trans. Either way I happily ate the sandwich, burnt bits and all. She was doing her best and I owed it to her to do mine. I was gonna rock the hell out of that goth club. 

 

After several hours and begrudgingly trying to figure out how to make murder Furby with legs that could and would kill, it was finally time to get ready. Lana was gathering all the makeup she had secretly purchased before coming out, and setting up on the kitchen table. I, however, was trying to quell the intensity of a thousand suns burning inside my chest. I had my bralette on; the hugging sensation was actually kind of nice. The dress adorned my body like it had been made for me. I had my matching red and black striped thigh highs and arm warmers on. My boots gave me a little bit of height and were a bit tricky to walk in at first due to the weight. But I felt powerful in them. I was a pretty goth…person. If only for a night. At least, I thought I was pretty. My outfit was on point, but I still needed to have Lana do my makeup. Plus the fact that I still couldn't muster up the courage to actually look at myself in the mirror. 

I shook the creeping thoughts out of my head and joined Lana in the kitchen where she was putting the finishing touches on her eye liner. 

“Hey, nerd!” She set her liner pen down and turned to look at me. 

Wow, did she look at me. Her eyes scanned every inch of me, with the biggest, cockiest grin on her face that I had ever seen. 

“Um, hi.” It was all I could do to keep from blurting out how gorgeous she was. Her outfit, her makeup, the way she fucking looked at me. Everything about her was dangerously, impossibly enchanting. Even if you took everything away, the clothes, the makeup, the higher-pitched voice she was using…I’d still think she was the most stunning girl I knew. 

“You look beautiful, Kenzie.” My heart stopped. She–called me by that name. Was I dreaming? No, she’d be on top of me by now if I was.

I clenched my hands around my skirt, I didn't have pockets to hide them in so I was panicking and unsure of where to hide them. You could have cooked an egg on my face, it was so hot. “Thank you. You look really pretty too.” My eyes darted furiously between random spots in the room, looking anywhere but directly at Lana. I tried my damnedest to hide my hurricane of inner thoughts and feelings.

“Oh gosh, I completely forgot when we were out shopping. We’ll have to get you some panties on the way there. Boxers are definitely not going to feel comfortable in that dress. Plus they’ll show if you move around too much.” Lana said, thankfully changing the subject. Unfortunately for me, it meant I had to admit something I had never planned on telling anyone.

“Well--you see. About that…” I rubbed my legs together. How was I even supposed to explain it? Though if anyone would understand, it would be Lana. “I might um--already be wearing panties. I actually haven't worn guys' underwear in about a year.” It was true, I was currently wearing my best pair, the lace and satin fabric hugged everything in just the right way. Panties were just more comfortable than boxers. It’s not like there was any other reason. 

Lana stared at me, or rather through me. Her gaze was thousands of yards beyond me. She was in an almost trance-like state. Not unlike the look she gave me after she came out. After a few awkward moments of silence, she finally snapped out of her daze. “Kenzie--I really think that you should…” She paused then let out a deep sigh. “Sit down so I can get your makeup started. You’re absolutely adorable and I can’t wait to have fun with you tonight.” 

I obliged and she started applying what she called primer and foundation. The brush against my skin was odd. I had made sure to get as close a shave as I could so I would receive the full effect of the magical paint. But still, having something on my face was going to take a little getting used to. Lana was laser focused, her hands were nice and steady. If only I could say the same about my face. When she applied the blush it tickled and flinched a bit, causing her to have to correct and reapply it. 

“Hey, Kenzie? It’s okay to be nervous. I sure was my first time with makeup. But you get used to it after a while.” Her dark winged eyes could soar as close to the sun as she wanted, and they could pierce the densest of materials. But in that moment all they carried was compassion. 

I took a deep breath to calm down yet still failed at steadying my body.

She leaned back, “Hmm, I have an idea. I need to do your eyes, but I don’t want to poke them out trying to apply liner or shadow. I like looking in them too much for that to happen. Come with me.” Lana stood up, grabbed a few things and took my hand.

I was led into the living room when she gestured for me to get on the couch. 

“Down.” 

“I--what?” I stammered, while instantly obeying and sitting down. Where was this going?

Lana smiled ever so softly at me, and slowly directed my body further down until I was lying on the sofa looking up at her. 

“Good girl. I need to make sure you stay still and this is the best way to make sure you don’t pull away or flinch too hard,” she said surprisingly plainly as she eased herself on top of me and straddled my hips. “Is this okay? We don’t have to do this if you’re not comfortable.” 

What was it like to breathe? I had forgotten how in the span of mere seconds. All I could do was lay there, like an unfortunate soul who had wandered into the gorgon's lair. I was nothing more than a marble statue for her to decorate how she pleased. 

She gazed deep into my eyes. “You doing alright, Kenzie?”

"Heh, heh, heh." I let out a nervous chuckle and nodded my head. I'm in danger.

“Good, now hold still.” She adjusted herself on top of me. 

Oh no. If she kept moving, things were going to…too late. The last shred of dignity I had managed to cling onto shattered as I felt the tightness in my panties and my member stiffened. Damn my literal dreams coming true.

Lana stopped, her eyes peered downwards towards our midsections, then her gaze locked back with mine. She shot me a smirk, then started preparing the pens and brush. With great care and precision, she started to apply shadow and liner to my eyes. I did my absolute best to lay as still as possible to avoid any more awkward situations. The last thing I wanted to do was make her uncomfortable. Though our situation was interesting. A girl sitting on top of another girl and doing her makeup. I felt like I had seen something like this before. But I wasn't sure where.

Wait, did I just refer to myself as a girl? I mean, I was pretending to be one for the night. I guess it was okay to think that way. But was it problematic for me to do that? I didn't want to invalidate or appropriate anyone’s culture or identity. Why was everything so complicated? I needed to get out of my head. Just enjoy the night. There I was, in the cutest outfit I had ever seen, with the prettiest girl in the entire world literally on top of me.

Fuck it, I was going to be Kenzie for the night. It was my last night to dress up like a girl, so damn it, I was gonna have fun for a change. 

“Okay, I think that should do it. Damn, I’m good. You look cute as hell.” Lana giggled and slowly eased off of me. “Why don’t you put your wig on so you can look in the mirror and admire, then praise my expert makeup skills.” She winked and then twirled around in her skirt. 

Okay, I was starting to understand the whole, “dress go spinny” meme I had kept seeing. It looked like a lot of fun and Lana was so damn cute doing it. I could stare at her for hours on end just being so happy and confident in herself. She was always fun and outgoing, but this was different. It’s like she wasn’t holding anything back anymore. I had to admit, I was a little jealous. 

But tonight was my night. I was going to stop holding back too. I stood up, grabbed my wig and affixed it to my head. I then decided I was going to do something I hadn't done in a very long time. With great hesitation I walked into the bathroom. My body was trembling, and my chest had ascended beyond the mortal realm as I looked at my reflection in the mirror. 

 

Sorry for the cliffhanger. (I'm really not but you know, lol) Thank you so much for reading! The story is now finished and completely out on my Patreon, There are 8 chapters total. But I will be releasing the chapters here weekly and begin on other projects very soon. I hope you enjoy.

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