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Cosplay Sissy: Bonus Chapter
🕑 Added 2025-08-13 16:01:18 +0000 UTCShe would pop into my stream every day to leave some little flirtation or another. Cute little remarks. She liked to call me ‘bombshell’. I would get all warm and fuzzy inside.
Ending those streams was the hardest part. Sometimes I felt like a sort of imposter when I stayed in that makeup and costume—but then I would feel like even more of an imposted when I cleaned the makeup off and saw myself in the mirror.
It was getting harder to recognize that ‘man’.
And it was getting harder to deny that I was meant to be NightLily.
Even just the way people treated me when I was out. They were so much more kind, so much happier to see me. And… they actually noticed me.
I hit a personal record: 30,000 viewers on my Saturday night stream. The comments came in too fast to read. Most of the viewers knew that I was ‘trans’—at least that’s the label they used. I still wasn’t sure what I was, or if there was a label for it.
Most of them were supportive. Countless guys hit on me, begging me to add them on their socials. I had a fan mail account that I had to close because it just got filled with pictures of throbbing erections. I wasn’t into cocks, but I appreciated the sentiment. There really is no better way to say ‘you’re hot’.
“Bombshell,” I noticed one night—the comment popping up for a moment before being buried.
I blushed. Then, I said, “Hey Maya. Thanks for tuning in. If you want, um… you’re welcome to come over… for a bit.”
I saw her tag go offline.
Fifteen minutes later, I heard the tapping at the door. “Sorry, guys. I’m ending the stream early tonight.”
And then I saw her at my door, blushing, that cute back of freckles glowing across her nose. “I have a surprise for you,” she said. She was wearing a big coat. I thought she was going to open it to show me her perfect titties and soft little bush above her pussy. Instead, she reached into the coat and pulled out a pamphlet. It was for the upcoming City Con.
“What’s this?” I asked.
“An invite,” she said. “I got a booth. And I need some big names for some live makeovers. I thought it would be fun to really glam NightLily up on stage.”
I turned dark red. The last con we went to didn’t end well. I hadn’t forgotten about it.
“I like what I have going now,” I said softly, nervously.
“But now, you have nothing to lose,” she said. “I mean—no sponsors or contracts. You’re self-employed. And people all know you’re… well, you know.”
I nodded slowly. “I have to think about it.”
“It’s this weekend, so don’t take too long thinking. Just be there. I actually have to run now… I’m meeting a client at a thrift store to source some pieces for a costume.” She leaned in and kissed me on the nose, making me blush.
She left me with the pamphlet.
I thought hard about it that night. She was right. What did I really have to lose now?
So I showed up at the con, dressed as NightLily. But this time, I had more confidence. I knew this character so much better than I ever knew that old character, because I created this character. And because… this character was really just me.
I found Maya at her booth. Her eyes lit up when she saw me. “You came!” she said.
“Of course.”
“Right on time. We take the stage in fifteen minutes. Do you need me to run you through breathing? And your wig. Wait—is that a wig?”
“No,” I said. “It’s my hair.”
“Cute!” she said. “It grows fast!”
“Yeah,” I said.
“Perfect. That makes this even easier. No hiding lace. No glue. Just makeup. We’ll do a big glam look. We’re going to make you sexier than you’ve ever been. Oh man, this is going to be fun. Come on, let’s get backstage.”
It all happened fast. I didn’t have to do much. An interviewer came up with a mic and held it up to my lips while I kept my eyes closed so Maya could doll me up. He asked me softball questions about games I was playing. Then, near the end of the interview, he asked if I had any resentment towards the studio for dropping me.
“Not at all,” I said. “It was their character. They can do what they want with her. And now, I have my own.”
Then came the reveal. It was a reveal for me too, turning to see myself in the mirror. She made me stunning. Skintight red dress, hair pushed over to one side, dark mascara on the bottom lashes. Bright cherry red lips.
The crowd oohed hard, and I blushed. Maya got a good applause. It was good exposure for her brand—and mine. I saw my follower count tick up a few hundred over the next hour.
“Back at the booth in fifteen,” the organizer told us.
“That should be enough time,” Maya said.
“For what?”
She grabbed my wrist and led me to one of the convention green rooms. She pushed the door shut and threw herself at me, taking me by surprise. Her soft lips pressed against mine, and then I heard her mutter, “You’re so fucking sexy.”
I wrapped my hand around her. I felt her grinding against me, and then I felt wetness. I’d almost forgotten how easily she squirted. Now, she was squirting through her panties, ruining that tight dress.
And the warm wetness made me hard. My cock stood tall, stretching that thin fabric.
She dropped to her knees fast, hands trembling. She didn’t even bother pulling up the red skirt. She just started sucking my cock bulge, clad in that stretchy fabric. It felt kind of weird, like a condom that was too tight—but nice in a funny way.
“I want to fuck you,” I whispered.
“Not as badly as I want to fuck you,” she growled.
“Do you have… a strap-on?” I asked, looking around nervously. That door wasn’t locked. And we didn’t have much time.
“No,” she said, but she spun me around and bent me over anyway. She tugged the skirt of that dress up. She yanked my panties down, making me gasp. Then, I felt two of her fingers, saliva-covered, twisting into my hole.
I gasped again.
“Are you going to finger me?” I asked.
“No,” she said. “I’m going to fist you.”
And then she pushed in. I yelped. She slowed down. A third finger went in—and then a thumb, and then the tip of her final finger. Slowly, she pushed. I felt myself stretching—wider and wider and wider…
And then: a pop. I gasped.
I felt her slide in. I felt my anus clenching around her wrist.
She pumped harder and faster.
I fell forward. I could see her arm between my legs, pumping in and out like some sort of piece of a steam engine. “Oh God,” I groaned.
I felt a euphoric swelling. I felt pulses of pleasure that I didn’t know were possible. I made sounds that were loud and wet and probably embarrassing.
“I’m cumming,” I said, voice strained.
And ten I felt the gushing. One shot landed on my own face. The rest coated the floor. She pulled her fist out slowly. Another pop. Another gasp. There was a moment of pain, but the lingering pleasure was overpowering.
We kissed. Then, she gently pushed me away. “Unless you want to go back to the booth with cum on your face, we’d better clean you up.”
I nodded, blushing.
