His Drag Debut

I was so nervous, standing up on that stage. It had been a whole day of trying to hype myself up, but I had no idea how I even mustered up the courage to do something like this. I breathed out a sigh of relief, there was no helping it now. The only thing I could do was do my best, and hope all the friends I made along the way on this journey would be there for me, cheering me on, telling me how great of a job I did.

It all started a few weeks ago. No, it started years ago when I began to realize that I wanted to start trying makeup. I went to stores and got cheap makeup that I left in my room, hiding it from everyone, and never had the courage to actually put it on my face. I watched tutorials on facebook, but all the queens were so beautiful, I could never compare to them. Not when I looked like this.

It was when I started university that I became more and more confident. There were many like minded people in the LGBTQ club at school, and they all encouraged me, along with putting on drag races. I sat there, watching the queens work as they pranced around the stage, laughing away. It was stunning. I wished I could be like them. A friend or two taught me how to put on makeup, and I sat there as they worked me up for the first time. When I saw myself in the mirror, I almost started crying. This was everything I've ever wanted.

That was when I tried myself. It was hard at first, my hands shook as I brought the brush close to my face, every stroke making me feel like I was doing something deviant. And then I did it, in my free time, when I wasn't bombarded with exams; I did it. I tried over and over again and I posted pictures on the internet with an anonymous name. I was so scared of what they would say, but they were all positive remarks. I wasn't perfect at first, but the people who tried to help me didn't say it with a snarky attitude. They told me how to match the colour of my concealer with my face, how to make my eyelashes as long as humanly possible. I mastered the makeup, but still felt empty inside. There was clearly something more I needed.

That was when I snuck out from school and purchased breast fillers and ass cushions to form my body. It was so difficult at first, trying to adjust it properly. But people from the club and online helped me, and I was filled with so much happiness when I saw myself for the first time. I ordered a dress in my size in the mail, hoping no one would see it. When I opened it, I almost cried. It was stunning. I couldn't wait to see it on my body. I was finally who I wanted to be, a queen just like any of the others.

Though... I still had no idea how to perform. That was something I had no courage to ask about. I hid in my room, and when I had free time, I started to dance to an invisible audience by tiktok tutorials, and tried to move as much as possible. The trick was to not be shy, which made me feel like I was very bad at it. I also had to work on my attitude. No matter how much I wanted to be fabulous, I was used to being a straight dude in my day-to-day life, a serious nerd in front of people who didn't know me at all. How could I transform so much like that?

I gave up for a while, I couldn't bring myself to actually go anywhere with my outfits. That was when I met one of my best friends online. A transexual woman who couldn't stop spurring me on. After a while, we started to talk to each other on the webcam, and she gave me so much confidence I thought I was going to burst. She lived on the other side of the country, but said that she would try to visit me as fast as possible. One day, she informed me that she would be able to visit the week of the biggest drag event in the city, which people from the college attended. I was so excited to see her, and was counting down the days, my smile not able to leave my face.

I picked her up from the airport, taking an uber there to make her as comfortable as possible. She put her arms around me and giggled, telling me I looked just like how I looked on the webcam. I couldn't stop smiling around her. I didn't know if this was anything more than friendship, but the way she touched my arm and laughed at all my jokes... I was hoping for something more.

On the night of the event, I sat in front of the mirror, gulping slightly. This would be my first drag debut. People had seen me in outfits on and off, but no one had seen me in my full drag apparel. Well, only my friend, Tiffany, through her computer screen. She watched and gave me suggestions as I caked the makeup on my face. I put on multiple layers of foundation, covered it in powder. I then glued my eyebrows down, and drew them much higher on my face. Then came the fake eyelashes, which I glued on with precision. I've done it many times, after all. I was an expert now. I then used three different mascaras and extended my lashes, making them fuller and more plump. Beautiful. I then put on a shit ton of glitter. Layers and layers of holographic glitter and black glitter that made my eyelids shine in the night, Tiffany nodded in appreciation. I loved how into it she was as well. The final touch was the lipstick. I needed something that stood out against the other queens, who would be bringing their A game tonight. I put on a lipliner, and then a dark red lipstick that was almost black, and Tiffany whistled in appreciation. "What are you going to wear?" She asked in awe.

I winked at her, telling her that it was a surprise. I left her in the living room for a few seconds while I walked to my bedroom, looking down at the dress in front of me. It had a huge slit to the side, all the way up to the side of my crotch. My breasts were showing off a significant amount of cleavage, and the glitter on the dress itself matched my eye makeup perfectly. It would be a fabulous first debut, I just knew it.

We linked arms as we headed to the theatre, already filled with the hustle and bustle in people dressed in all kinds of apparel. I felt my chest tighten, a little intimidated, but all I got was compliments, and I felt confidence growing in the place of anxiety.

"Yasssss queen! Look at that dress, I just want to bend you over and push it up and fuck you!" One queen said, smiling at me. I was used to this kind of vulgar language, and it made me a little hot when they treated me like that. I wish she would just do it!

"You shouldn't be saying that when you're slaying tonight!" I winked, and gave her a huge hug. Our breasts bounced against each other as we did.

"No, you're the ultimate queen tonight. I'm going to introduce you to everyone!" She said, and started to drag me along, announcing her new prodigy to everyone. "This is Cherry Pie, it's her first time coming out in drag!" She grinned ear to ear.

Tiffany followed me with a drink in her hand, having a great time as well. I had never been the centre of attention like this before, and I loved it. I became more and more involved, screaming words like 'bae', 'queen', and 'slay' at every queen I could find. They screamed it back at me, their asses jiggling away as they bounced up and down.

Soon, it was time for the show. I was invited backstage, and watched from the side as they came up on stage, lip syncing perfectly to their favourite songs. The crowd went wild, laughing and cheering them on, or whistling when they made a particularly risque move. Tiffany whispered in my ear, and I tensed up when I felt her lips against me, "I have a surprise for you."

I turned to face her. "What is it?"

"You're going up on stage tonight! I had it arranged this whole time!" She laughed.

I looked at her in shock, my pupils completely dilated. "No fucking way, I'm not going up there!"

"I believe in you." She said, pressing her hand on my biceps. "I've seen you dance multiple times, and I know you're meant to do this."

I shook my head, not letting her words soak in. She pressed her mouth on mine, and fluttered her lashes at me. "I believe in you." She said again. My heart swelled a few sizes. The song was over at that instant, and she pushed me onto the stage while I was distracted.

I stood there in the centre, looking at the bright light that was shining at me. I had practiced dancing on high stilettos for months now, but my legs were shaking as I stared at the audience. "You can do it!" I heard her voice scream from behind me. I nodded, and I heard it - my favourite song from Beyonce came on. My body started to move without me realizing it, it seemed I had danced to this song so many times now that I knew everything by heart.

The audience started to cheer for me, chanting my name over and over again. "CHERRY PIE, CHERRY PIE, CHERRY PIE!" It spurred me on, and sweat dripped down my body as I panted, showing off all my moves, but I didn't care. I just wanted to keep going and going. I almost felt disappointed when the song finally ended, and I stepped off the stage as they cheered even louder, some people even standing up for me to clap.

It was everything... everything I could ever ask for.

I felt tears running down my eyes... I couldn't thank Tiffany enough for doing something like this for me. I had to thank her... show her how much I appreciated her. And I knew the perfect way to do it.

That night, after an evening of celebration and drinking our asses off, we stumbled into my apartment, holding each other steady. She pushed me against the wall and started to kiss me, twirling her tongue against my mouth as I moaned out loud. I was very inexperienced, but I hoped I knew what I was doing. I kissed her back, letting my body do the work. I shook my head. "No, this is for you. I shouldn't be enjoying this, I want to give you a gift for all you've done for me." I said seriously.

She looked at me in surprise. "What kind of gift?" She asked.

That was when I dropped to the floor, kneeling in front of her. I pulled her pants down, and her dick sprang up, a thick girthy one that almost hit me in the face. "Are you sure?" She asked, cautious.

I nodded. "I've been wanting to do this for a while now, though I'm inexperienced, so let me know if I'm doing anything wrong." She nodded, agreeing with my request.

I put her dick in my mouth, sucking hard at the tip. She groaned, and thrusted into me, letting her dick take over her mind. I swirled my tongue against it, tasting her as I breathed in, smelling the thick smell of her balls and cock. It was addicting. I bobbed up and down, doing my best to maintain my composure and not touch my gag reflex as I worked my way down, trying to get as much of her inside my mouth as possible. She loved it, and grabbed my head to help me along. She moaned and groaned my drag name, which I loved. It spurred me on, and I almost wished I could touch my own dick. It was throbbing in my pants, asking me to please, please play with it. But I couldn't, not when my job was to satisfy her for the night.

"You're such a little slut, Cherry." She said as she thrusted into me. I moaned into her dick, loving the dirty words that had come out. "You love having a big fat dick in your mouth after a show, don't you?" I nodded, and tried to talk, but she shoved me back in. "Good girls don't talk when dick in their mouth." This was so different from how she usually was, and I was shocked, but it turned me on so fucking much I didn't care at all.

She was thrusting so hard that she was hitting the back of my throat and bending in it. My gag reflex took over, and I started to cough and gag at the feel of her dick. "Yeah, gag for me, bitch. Take dick over air." I was indeed taking her dick over breathing, and I had to wonder how long I could hold my breath for. It didn't matter though, I wanted to make her as hard as possible. It felt like she was expanding in my mouth, becoming even larger and larger, and I wondered how much I could take. It was so fucking good. I wanted to do this every night, to be treated like the whore that I was. I was glad I was doing a good job as well, because she had no complaints about what I was doing at all. I let her thrust into my throat at her pace, and used my tongue to swirl against her and lick as much as possible. She grunted, and I could taste the precum in my mouth. She was clearly close.

I could feel the tears down my eyes as I choked on her thick cock, and she smeared the makeup all over my face, and the running mascara on my eyes made me look like the whore I really was. It was so fucking hot. I wished I could see myself while I took her down like that. It seemed that I was doing a great job, because she moaned my name over and over as I fondled her balls, and finally, it was too much for her to handle. I felt her balls tighten as she groaned a guttural sound, and she came inside of my mouth. It was the first time I've ever tasted someone else's cum, and it was salty and bitter as it slid down my throat. Just like what I expected.

She let go of me when she was done, and I grinned, wiping the cum off my face. "You're so fucking good at that." She said.

I laughed. "Thank you."

"Go look at yourself in the mirror." I listened, and walked to the bathroom. My mouth shot open in shock. It was worse than what I imagined. All of my makeup was smeared, and the three coats of mascara were now dripping down my face. "That's what a whore should look like." She whispered in my ear as she put her arms around me from behind.

I closed my eyes, enjoying the feel of her against me, and thought about all the exciting things that life had in store for me.