When I was 18 (I’m 26 now) I was on the beginning of my home phase as a bottom sissy type of guy. I already had a decent body count and I was hungry for more experience.
One of my regular guys suggested to me that we take a weekend trip to a resort nearby. He would bring a friend or two and I am to be the only bottom. We would take a house with a pool, enjoy for the weekend and go back.
So I come to my dad with the grand LIE that I would like to take this girl out for the weekend and I’m really in love and etc..
So I got some bucks and the car.
I spent the money on panties, stockings, lube, and a pair of high heel knee high black leather boots.
I arrived last and it was 4 of them in the house but that’s a different story.
Once it was all over I drove back home. My mouth hurting, my ass gaped a bit ( I think I was leaking some cum even) wearing thigh highs and panties under my male clothes.
I handed my dad the keys and told him it was wild and thanked him alot.
He winked at me and said “glad you had fun, it was about time you get active with some girls”.
I made up a story that we broke up a week later which I told him and he bought it 100%
So my dad doesn’t have Reddit but if this somehow gets to him
THANKS DAD ! 💗❤️❤️🔥