[M4A] Date Night
I am 18+ and all participants and characters must be 18+ only
I checked myself in the mirror. After two hours of youtube videos, more money than I would have wanted spent on make up and countless attempts, I had done it. I had applied make-up. My face was shaved and I had to admit I was surprisingly attractive. My skin was smooth, I had shaved and waxed. My skin was shiny. I wasn’t sure why that was important but it was. The process was done. Now I needed to put on the clothes.
I still couldn’t believe I had been convinced to do this. That I had agreed to crossdress and go on a date. It was insane. The money I had been offered did help. It was enough to deal with my loans. It was enough to buy a house. It was enough to deal with all my immediate issues. I just needed to make sure nothing happened. I would sacrifice a weekend and a few errant questions, but then I would be done. I finished packing my bag and checked my phone. The car would arrive in thirty minutes. That left me plenty of time to get down to the street and outside. It would give me enough time to put the chastity cage on. That was by far the worst part of the outfit.
It was also needed. I couldn’t afford to have any bulges or anything beneath the dress. As it was tighter than I wanted. It was comfortable, but it wasn’t designed to hide my package. I placed the key in a drawer and grabbed my bag. Two days and I would be free of all this madness.
Details
Genre:Modern | Dark Romance | Crossdressing | Sissification | Blackmail | Slow Burn | M/F | Literate/Advanced
\\\*\\\*Themes:\\\*\\\* Conditioning and Habituation, Identity Loss, Entrapment, Coercion
\\\*\\\*Looking For:\\\*\\\* 21+ writer willing to play a character along side my crossdresser.
DM me with “Date Night” at the start of your message to let me know you made it this far down.
Posted Jul 25, 2026, 11:30 PM UTC