Lately I got curious and I dressed up like a girl. I looked so good it was unbelievable, but I didn’t want people to see me so I had to go during night. There wasn’t anyone in the park and I had the place for myself. I lowered my panty and sat on bench, then started fingering my butt.
It felt so good my dick was rock hard, but at that moment I felt something grope my ass and I froze up….. I soon realized there was a man behind me touching my ass. I was shocked and couldn’t move, so I stay silent as I felt a hand grab my ass firmly. I was infuriating, how could somebody do something so horrible.
I felt his hand moving down my skirt, inside my panty. He caressed my bare ass with the palm of his hand. The situation was getting out of hand so I told him I was a boy, but he didn’t stop.
That’s when I was truly terrified.
After a couple of grabs I suddenly felt one of his fingers poking the entrance of my asshole. There is no way he would go that far in public!……………Right?
At that moment I felt his finger go in my ass. I can’t believe he just did that. He started moving his finger more and more inside me. I was paralyzed at that moment. My ass felt numb and i felt disgusted as I realized the very first time having my ass played with wasn’t by a curious and loving boyfriend but by a random pervert. He finally took his finger out my ass and out of my panty. Finally it was over ans he had his fun.
As I barely started feeling relief once gain I felt something pushing against my ass but………….but it wasn’t the feel of a hand or a finger. I couldn’t believe it, he was slowly brushing his hard cock against my ass. Then with horror I felt my panty getting lower. I had to do something, I wouldn’t let some stranger take my virginity. Before I could rethink my options he pushed his cock inside my asshole. I wanted to escape but he held my hips , he was raping me. Fucking me in the ass and all I could do it watch.
Then he slid two fingers in my butthole while pounding my previously virgin ass ,I could feel every inch of him entering and sliding out my ass. It felt so weird and dirty like a forbidden way of doing it. I couldn’t help but feel the tiniest bit of pleasure making its way inside me. Then I realize with shame that I was indeed getting hard. Unbelievable, how could I get that aroused being raped in the ass by some bastard. He fucked me harder and harder.
Then he stopped all of the sudden and with what will forever be a stab in my pride and self-esteem I, not even realizing it almost as my body had taken over my mind, pushed my ass towards his cock. I barely stopped myself from cumming having his cock and fingers inside my asshole. Then he started ejaculating ,filling my insides. My hole was leaking with cum. I got home trying my best not to let shame overcome me as I washed the cum off my legs.
Source: reddit.com/r/eroticliterature/comments/sygxnp/that_was_so_humiliating_crossdress_anal_18m