Adventures of a crossdressing sissy punished for stealing.
A crossdressing sissy punished for stealing my favorite pair of panties. The little thief thought he could get away with it since he had just started getting curious about sissyfication. Now, he felt super-confident that he could steal my favorite pair of pink panties and run off with them, but no. Unfortunately for him, he had the worst timing in the world! See, let’s start this story off from the beginning. This little sissy’s name is Jake. When I met him, I thought he was a completely normal boy-toy for me to flirt with. He dressed nicely and groomed himself carefully as well. I didn’t realize he did all this because it was his version of primping and prepping himself.
Everything he did, he did it to feel more feminine and groomed. He liked feeling well-kept. His shirt was always ironed nicely, no wrinkles in sight. He always smelled terrific, his hair still smelled like raspberries, and I thought I recognized the shampoo he used but didn’t want to ask if he used women’s shampoo. His skin, when I got close, smelled like a fruity coconut shower gel that I thought I recognized from Ulta, as well. I didn’t realize it then, but everything about this guy was well-kept, and it screamed out, “faggot!”
It took me a while to realize it!
He acted like any other guy. He spent a couple of nights at my place after we went drinking with some mutual friends, and the party ended here. It was business as usual. He stayed completely normal until he decided to get a little handsy, and not in the way you’d expect, either. I didn’t catch him stealing a quick grope or grab. Instead, I walked past my bathroom to see him taking a pair of my pink panties from the hamper. The dirty boy slipped a hand into my dirty clothes hamper and yanked out my delicate magenta-pink lace thong. I didn’t think he’d try to wear them, so why the hell did he have them? I pondered and watched him, expecting him to sniff them to get his kinky little rocks off.
That’s when he yanked his pants down; boxers included and pulled the little pink thong up. He stretched it a little to fit them over his hips, though his cock wasn’t much of a problem. It was small enough while it was soft that every inch fit snugly under the front of the thong. The pink lace hugged him deliciously, and he was enjoying it. The sissy showed off in the mirror, like no one’s business. He arched his back, shook his ass, and did everything he could to show off how sexy and feminine he looked in my lingerie. That’s when I decided I’d make him pay for it. He’d just be another crossdressing sissy punished for stealing my panties.
It was time to make him my bitch.
He thought he could get away with acting out his fetish phone sex dreams. He danced around in the mirror for a little while before I finally barged in. I swept the door open, tapping my heels impatiently as I watched him. He knew he was in trouble. There wasn’t a single way out of that. He simply couldn’t come up with a creative, reasonable explanation for wearing my panties and dancing around in them. I caught him red-handed, and it was time for him to be another crossdressing sissy punished for stealing lingerie. I shut the door behind me and locked it. He thought he was safe. He believed I’d keep his secret between us, but he didn’t realize that I’d make him work for it.
I told him to take his shirt off. He obeyed instantly, and I took my phone out. The fun began with me taking several pictures, ordering him into all kinds of positions. I made him suck on his fingers for the camera and bend over and shake his ass for it as well. He twisted around in all kinds of positions for me. Once he was on the floor, I got to really have my fun. His back arched, and he stuck his ass in the air, and that’s when I went looking through my ‘fun’ drawer. I plucked one little bottle of lube and my favorite strap-on out. I made sure to hold them up so that he could see the reflection in the mirror, and he instantly knew what his punishment would entail…
But I will keep those deliciously-dirty details for another time.