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Sissy Queen: Bonus Chapter
🕑 Added 2025-10-06 16:35:33 +0000 UTCThe apartment smelled faintly of candle wax and something sweet—vanilla, maybe. Sybil’s idea. She said every ‘experiment’ deserved the right atmosphere.
An experiment. That’s what this was supposed to be… but it didn’t feel like an experiment. It felt like we were playing around with something we already knew.
I sat on the edge of the bed while she circled me like a stylist preparing a client, teasing me with a half-smile.
“Relax,” she said. “You already looked great in pink once, remember?”
I laughed under my breath, tugging at the hem of the silk skirt she’d handed me. “That was a parade costume.”
“This is just for fun.”
The fabric slid cool against my skin. Sybil adjusted the collar, her fingers lingering. “You always underestimate how good you look when you let yourself play a little,” she whispered.
I met her eyes in the mirror. They were bright, mischievous, but soft too—no mockery, just curiosity and affection. She brushed a bit of gloss across my lips, then stepped back to admire her work.
“Perfect,” she said.
I felt my cheeks warm. “You think so?”
“I know so.”
The way she said it—low and certain—made my pulse skip. The room seemed smaller, the air thicker.
I turned toward her, and she was already close. My hand found hers, fingers interlacing, the light from the candles catching on the faint shimmer of the gloss she’d applied. I kept looking over at the mirror, but only for a moment, because I wanted to look at her. She was so beautiful.
“Still nervous?” she asked.
“Not exactly,” I murmured.
For a heartbeat we just looked at each other, the silence humming between us.
Then Sybil smiled, tilted her head toward me, and said softly, “Good. Then let’s stop pretending either of us wants to talk.”
The candles flickered, shadows merging as she leaned in.
I still felt a bit silly in the little dress. It was so cute—and the way it felt against my skin was so nice, but I still didn’t really know how the world felt about it. People were nice. At the parade, nobody knew a thing until I ran up to Sybil and outed myself. And yeah, there were blushing glances and compliments—but even with all that, you never really know.
But maybe it didn’t matter. Maybe I didn’t care about what anyone thought about me—anyone who wasn’t her. I only cared what she thought. And unless this was all performance, she was happy.
The way her eyes clung to me, moving up and down. The way her lips pouted and she whimpered at the sight of my thighs under the short skirt. The way her fingers grabbed at me as if she couldn’t help herself. That wasn’t fake.
We kissed. She let me undress her, but she insisted I stay dressed. She liked the feeling of the lace and satin rubbing against her. She was grinding hard against my erection, which was stretching out the tiny panties she’d given me. I could feel her wetness.
“I want to fuck you so badly,” I whispered.
“Not before I fuck you,” she said. I felt her grin against my lips. Then, I saw that she had the strap-on nearby—ready. She giggled, grabbing it quickly, as if I was going to grab it first so she couldn’t touch it.
We’d used it before. It was fun before. But it was all so new. That was such a blur. Now, I felt ready. I felt like I was in a place to really experience this.
And it seemed so important—like a huge determining factor in whether I wanted to go down this route of being a girl.
She strapped it on slowly. Her cheeks turned dark pink. I held my breath.
“Hands and knees,” she said, pointing at the bed.
My cock was so hard. It was stretching out the panties, tenting the skirt—almost comically. It was leaking. How could I help it? She came up behind me and grabbed my butt cheeks with both hands. Carefully, she pulled my cheeks open, looking at my hole. “It’s so cute,” she said.
I bit my tongue. She spat—good aim. The spit trickled over my hole. She used the tip of the big toy to smear it around the hole. I puckered, which made her giggle. Then, she put her finger in to test me. I gasped.
“You’re tight,” she said.
“You’re… manicured.”
She wiggled her finger in me, making me gasp again.
“You’re going to like it,” she said.
“I know.”
She put the tip in, stretching me—and then pausing. She was being nice—but her niceness was about to run out. I let out a soft sigh. She pushed deeper. I gasped louder, clutching bed sheets.
She let go of the cock; my asshole was holding it firmly in place now. So she was able to use both hands to grip my hips. I let my face fall to the mattress. She slowly slithered into me—deeper and deeper. One inch at a time. God, it was so big. I was so tight.
I felt so full. “Is it… all in?” I asked, when I felt her started to gently thrust.
She giggled. “Not even close!” she said. “I’d say… halfway!”
I bit hard on my tongue. I felt her adding an extra quarter of an inch with each slow thrust. I couldn’t believe how much was in me—and how much was still left!
I gripped the bed sheets tighter. I tried not to let out a little squeal, but it came out anyway—and it made her giggle. She decided to give me a spank on the ass, which made me clench hard.
Then, she bent over me. I felt her breasts against my back. She reached around and found my cock with her fingers. She didn’t take it out of the panties; she didn’t have to. She gripped it through the undies and began to massage it.
“Does that feel good?” she asked.
“Y—Yeah,” I said, barely able to speak.
She was thrusting a bit harder now. A bit faster.
I stammered. I felt weak. Submissive. I couldn’t believe what was happening. I couldn’t believe how… good it felt.
She pushed deeper. Now, I could feel her pelvis. She was totally inside of me now. Ten inches or so—all in my body. I gasped.
She spanked me again. She played with my cock more. I didn’t last long. I began to gush and spill cum into the tight panties. The panties couldn’t hold my seed. It spilled out, left and right, dripping down onto the mattress, dribbling warmly down my thighs. “Fuck!” I cried out.
“You like it!” she cheered, but she didn’t stop. She was having too much fun. The strap-on straps had a space: an opening where her pussy was. She had two fingers down there now, rubbing her clit, gently fingering her wet hole. I couldn’t see it, but I could hear it. She was wet enough that it made sloppy, loud noises: gushing and queefing. She was fingering herself hard.
“I came,” I said, out of breath.
“I know,” she said, but she didn’t stop. “But I’m still cumming. Oh… God.”
She kept going. Fingering herself while thrusting. She didn’t stop. After a few minutes, I was hard again—and I didn’t want her to stop. Sweat dripped from her forehead onto my back. We were both slippery with sweat. Cum was still dribbling down my thighs—and now, she was playing with my cock again. She couldn’t help herself. It was hard and sticky and throbbing in what must have been a very satisfying way in her hand.
She made me cum again. More white goo spilling out the panties.
“Fuck!” she screamed, and I heard the wet splashing on the bed sheets. She was squirting.
She froze, deep inside of me. I could feel her trembling all over. Then, she pulled out slowly. The cock came out with a pop, which made me gasp loudly.
She fell down beside me, spent, blushing. She grinned and I laughed.
She started laughing. “Give me ten minutes,” she said. “And then you can fuck me. But… only if you stay dressed like that.” She bit her bottom lip.
“Deal,” I said.
It didn’t quite take ten minutes.
