Daily Free-Write August 13, 2020

Well this is a fine mess you've gotten yourself into. Diapered, and stuck in your girlfriend's closet while she lies in bed. You were just coming by to check up on her and let yourself in. You saw the house was empty, so you were going to leave, but then you decided to try something different. 

You snuck into her little sister's room first. You know she wet the bed at night, and she had some Ninjama pull-ups that you'd been eyeing for weeks. This was your chance! You grabbed one and ducked into your girlfriend's room. There  you got undressed and tried it on. It was incredible. Like nothing you'd ever felt before. You knew it was wrong but you couldn't resist. You also wanted to try on something of your girlfriend's. You tried on her cute nightie - the sheer one with the fuzzy fringe that left fluff everywhere. It was perfect. You felt so hot in this getup. You took a look at yourself in her full length mirror and you were hooked. Lost in your fantasies and staring at yourself in the mirror, you lost track of the time, and as you heard the door open, you scrambled to get dressed, but there was no time. 

You kicked your clothes under the bed and dove into the closet to hide. That's when she came in. And she wasn't alone! She had another guy from your school with her! He was one of the popular guys on the football team, and your biggest rival. You wanted to burst in on them and tell them what for, but you were dressed like a sissy and you would never live it down if they saw you like that! You just had to hold your breath and wait. You watched as he pounded your girl over and over, and she moaned. 

You were starting to get hard watching it happen. You couldn't help it. You started rubbing yourself through the pullup, and it felt amazing! Your heart was beating hard, the sensation of the pullup against your penis was so intense, you let out a moan. You quickly covered your mouth. Suddenly the stopped.

"Did you hear something?" He asked her, in a low whisper. 

You held your breath, as he cautiously got up and looked your way. He was getting closer. Closer. And then he flung open the closet doors to reveal you in just a pullup and a nightie, and he burst out laughing.

"Ohhhhhh my godddd, Casssssiiie! Your boyfriend is.... He's...." He couldn't finish the sentence, he was on the floor laughing too hard.

"Mikey! What are you doing here? A-and why are you wearing my nightie...and...one of my sister's pull-ups?" She looked totally confused for a second, but then the humor of the situation hit her, and she started cracking up as well. 

"T-this isn't funny, guys!" You yelled, your face getting hot with anger and embarrassment all at once. 

"Yeah, dude! It's hilarious!" said Chet. "What a wussy! No wonder your girlfriend needed a real man to fuck her, right babe?"

"Sorry, Mikey. You just don't measure up. I think you look better like this. You can keep the nightie - it looks better on you anyway." She started laughing again. 

"Look! I think he likes watching! He's even got an erection! Do you like watching your girl get plowed by a real man, sissy boy?"

You found yourself blushing and nodding despite yourself. 

"Well, fuck," He said, turning to your girlfriend. "I'm game if you are. Should we let the little sissy watch while we finish?"

She laughed and nodded. "Sure, this oughtta spice things up a bit!" 

They resumed their fucking and Chet made a point of keeping eye contact with you as he finished her off, making her cum multiple times - a feat you'd never accomplished. As she came for the final time he mouthed "You're next," to you, and you came in your pull-ups. He meant it too, because the next day, you got a text message from Chet.

"Had a lot of fun watching you squirm yesterday, sissy. Come to the football field tonight at midnight and wear that cute nightie. I'm going to show you how a real man fucks."