Beginner Femboy Ruined

First day out as a femboy takes a very dark turn

To start, this is a fully fictional fantasy of mine. I have not yet become a femboy but very much want to.

Three weeks ago I went shopping for women’s clothing for the first time. I picked up a few skirts, some thongs and other panties, plus some sports bras and tank tops. I felt so horny trying them on, I came multiple times in different dressing rooms. I still live with my parents so I had to sneak all of this inside. When my parents were out, I would parade around the house in knee high socks, a thong, and bra with my cock sticking out of the thong. I bought myself a dildo kit that I’m working my asshole up to the mighty, 8 inch dick. I’m currently at four and it feels so good. I have the best orgasms.

My parents were gone for a weekend and I thought it would be a great time for me to finally go in public with my favorite outfit on. A red bra, my tiny black tank top, a bright red thong, and a light blue skirt. I decided to go get some food at a local restaurant. I ate my meal there but noticed I was being checked out by a big, strong man. He had to have been 20 at least, but not much older. I finish my food and walk out and he gets up at the same time. Right outside of my car, he puts his hand on my door.

“Where do you think you’re going?” He asks. “Umm home.”
“I don’t think so.” He picks me up and carries me behind the restaurant. It’s dark so no one sees and he’s covering mouth so I can’t scream. He sets me down and pins me against the wall. “Why are you dressed like that boy?” He asks. “I- I just thought it would be fun.” I’m scared and acting innocent. “You should know if you dress like a bitch you’ll get treated like one”

He forces me onto my knees and quickly whips out his cock. I had only ever taken four, and his had to be ten inches. It was so big but he forced it in my mouth. I was crying and gagging and almost threw up but he kept fucking my throat. Finally he threw me on the pavement, lifted up my skirt, and said “that’s what I like to see.” He slid my tiny thong to the side and started licking my asshole. God it felt so good but I wanted to get away from this stranger. I was helpless.

I tried standing up but he was around me; holding me down. He got up, put his hands on my shoulders and whispered “this might hurt.” He slid his huge dick into my tight asshole and it took everything in me to not scream. It hurt but felt so good at the same time. He started slowly fucking me. I started taking it better and asked how much was in. He said only half and I started to freak out. He pushed it all in in one quick thrust and I fell onto the ground. I was crying. He picked me back up into doggy and rammed my asshole, all ten inches. I was sobbing and my dick was pulsing at the same time. I exploded my cum onto the ground letting out a loud, girly moan.

He flipped me over onto my back and stroked me while he pounded into me. I couldn’t do anything but watch as he continued to rape me. I came a second time onto my tank top and he came all inside my asshole. I loved the feeling of getting filled up but everything else of me hurt. He picked me up and carried me back to my car. Last thing he said before he drove off was “Hope I’ll see you around.”

Now every time I dress like this, I fantasize of him taking advantage of me. Next, I want multiple guys to have their way with me and make me their fucktoy