I dressed up as a girl and let a stranger with a girlfriend and a [m]assive cock fuck [m]e raw for my first time.

[Picture from the night](https://imgur.com/a/ktlqweH)

This is a long one but I promise you, it’s worth it.

So bit of background: I am, for the most part, a straight man. I’ve never really liked gay porn and have only ever had heterosexual relationships – all of which have been really healthy.

However, ever since I was young, I have had a fascination with woman’s clothes. I’m not sure why, but it started out as sneaking into my sisters room and wearing her underwear and liking the way it made me feel. The strange thing though was that when I dressed up I started to feel like a woman, which in turn made me think sexually as a woman. So naturally, it wasn’t long before the whole thing snowballed into me being a full time closet crossdresser whose favourite thing in the world was his sisters dildo that he discovered in one of her drawers. I also discovered crossdresser, sissy and trap porn which basically became my staple. My ultimate fantasy was to be fucked senseless while dressed like a slut by a big strong man. Of course I have never told a single person any of this out of fear of what they’d think.