Your life started when you admitted to me that you love cross-dressing panty play.
Well, it’s not like you really had a choice to admit that you liked cross-dressing panty play. I walked in on you playing a dress-up princess in my closet. A couple of my panties were thrown around the room. You just stood there, shocked. You had on my black stockings, a black lacey corset, and matching shiny black high heels. A living doll is exactly what you looked like.
I stood in the doorway at first. I didn’t want to stop you from whatever you were clearly very into. Your dick was rock hard and I could see the bulge in the satin panties you had chosen and matched with the rest of your outfit. You looked like something straight out of one of those gay porno magazines. I never knew that my roommate was a sissy bitch or into cross-dressing panty play.
You always acted so masculine. You had a great job as the head of a big company but here you were dressing up in my closet. My first thought was to snap a few pictures so that you couldn’t deny it later. I didn’t want to blackmail you, but I did need some kind of insurance so that you couldn’t deny it if you tried. So, after I took about ten photos, and a minute-long video, I hit my hand against the wall. I wanted you to become aware that I was there.
The look on your face was priceless.
You looked so stunned that you had gotten caught in the middle of your cross-dressing panty play. I hated to ruin all the fun you were having. But I felt compelled to know how long you had been a sissy! You had certainly done a great job of hiding it. Then, you started muttering excuses. I didn’t really listen to them all but one, in particular, involved trying on the lingerie for your girlfriend.
Your excuses just made me laugh at you even more. They were truly pathetic. Especially since you were standing in front of me looking like a high-class escort. Your cock was still a nice bulge in your panties. The fact that I caught you just turned you on more.
You must like panty boy domination, you couldn’t even hide it.
That’s when I told you that I would have to punish you for many things. I mean first, you dressed up in my lingerie! How invasive is that? Also, you clearly lied to me. I doubt your girlfriend would take an interest in the same sultry corsets I like. She seems much more vanilla than that, she’s a girl that’s easy to read.
I left the room and you waited impatiently. When I came back, I had a hand full of clothespins. “These are going to be the perfect accessories to your outfit! You can’t wear something like that without an accessory!” I whispered in your ear, as I ran the clothespins on your neck. Then, I pulled down your corset, exposing your nipples. Quickly, I snapped two clothespins on each nipple.
They quickly turned a bright shade of pink.
I stepped back so I could admire how red they were becoming while you couldn’t stop moaning in agony. I sighed. Your pain tolerance has always been horrible. We’d have to fix that if you wanted to keep doing cross-dressing panty play in my clothes. I wanted you to dedicate yourself to be my plaything. Which it seemed you were quite desperate to do. Unexpectedly, I yanked all four clothespins off at once which made you send out a howl that echoed throughout the whole house. I couldn’t help but giggle.
We would have a long way to go to fully train you, but I knew it would be worth it. I told you to bend over, and I disappeared again. I came back with a wooden paddle and told you to spread your legs. “Just today I’ll let you keep your panties on”, I told you teasingly. “You may need the extra padding”. Those were the last words you remembered before I brought the paddle down on your ass countless times. It sent you to a level of pain and pleasure that you had never felt before. And this was only the beginning.
Call your favorite phone sex operator and let’s see how much fun we can have!
