Thing is, Pauly's not trans, just gay. He chimped out when his bisexual boyfriend left him for a woman so in a drooling spedcow level move, he decided that instead of finding another gay freak in the body mod scene (lord knows there's no shortage of them) he'd get his penis cut off and larp as a woman if his partner "loved women so much". It's the biggest "the loser is you" move I've ever seen. Even without knowing he has body dysmorphia, the erratic tattoo/blackout/remove/pierce cycle that screams some sort of personality disorder left to run wild, I'm not surprised he'd make a life ruining decision on a whim, and out of short sighted spite, no less.
Pauly, you can't get a date or get people to look at your nudes because not only do you look like an ogre, but because everything about you screams "psychotic lunatic", like the type who's going to burn down your apartment complex with you inside because you broke up with them. So you do fit one stereotype of a woman: the psychotic dangerhair.