Crossdressing dream comes true...

Part 1

Heyyy, I'm Olivia, and thank you so much for checking out my story! This is Part 1, let me know if you'd like to see any more. (I have 6 total parts finished, lol, I got a bit carried away...).

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My name is Leo, I'm 16, and I'm a sissy boy. I'm 5'5", skinny, and have blond hair just past my ears. I watch sissy hypno, look at sissy captions, and dream of wearing sissy clothes. Although I'd worn my mum's bras a few times, she never wore dresses or skirts, so I could only dream of fulfilling my sissy life.

It was lunchtime at school - I was in Year 11. Heidi walked up to me. She had beautiful red hair, and was very pretty, yet really smart and confident. She was a bit taller than me, and seemed very dominant. I had a huge sissy crush on her. I wanked to pictures of her on her socials, imagining her feminising or pegging me.

She leant towards me and whispered in my ear seductively.

"I know you've got a crush on me. You've been wanking to pictures of me as well as gigabytes of sissy porn. Do as I say, or I'll tell everyone what a sissy you are!"

I stuttered, my tiny dick readjusting in my underwear,

"What are you talking about!?"

"Why else would you be looking at sissy captions and small dick humiliation!" She said, "After school, we will both go to my house to sort out any confusion, yes?". She leant in, "Or do you want me to send the sissy captions of yourself that you made to the whole school?"

"What!? How do you know... I'll come! Please, don't!" I stammered, panicked. She giggled and walked away.

Throughout the next lesson, she kept glancing over at me, smirking. I had no idea what she had planned. After the lesson, we walked home together, I was really nervous. We arrived at her house, and walked up the stairs, into her room.

"Take off your clothes!" She demanded.

"What! Why!" I stuttered.

"Do it, or I'll tell everyone what a sissy you are!" She shouted. I took off my blazer and tie. Keep going, Leo!". I took off my shirt and trousers. I was standing in my underwear in front of a hot girl. My tiny dick got rock hard, and a small bulge appeared in my underwear. She looked down and saw it.

Suddenly, I was on her bed, and she was on top of me. She burst into laughter.

"Leo, your cock is so tiny! Can I touch it?". Before I could say anything, she lifted up her grey school skirt and put her white pantied bottom on my face. I felt my underwear being removed, and my little dick spring up. She took hold of it with two fingers and rubbed it. Her skirt brushed along my hair as she reached forward. Her pantied ass was so soft against my face, and she sat in a way that meant I could talk and breathe. My dick became harder than it ever had been, still nowhere near 2 inches, but it was pulsing and hurting. Heidi noticed, and stopped stroking it. She was edging me.

"So, I've been monitoring your activity online ever since you accidently sent me that sissy caption of yourself, which was pathetic, by the way." She said, calmly, and started stroking my dick with her finger and thumb again. The caption that I accidently sent her was a full body picture of me naked, my tiny dick erect, surrounded by pink text.

"I thought I deleted that before you saw it!" I cried, muffled by her panties.

"Nope, I saw it alright. I screenshotted it too..." she explained, taking her hand away from my dick to take her phone out, "Let's see if I can find it... oh here it is!" She said, laughing, "Sissy boys don't have dicks, they just have sissy clits." She read out, "Your dick looks smaller in real life than in that picture, and that's saying something!"