Practice Outing: An Impulsive Dare To Myself

I think this... sort of counts as the first kinky thing I've done? That said, not counting things I've tried without leaving home.

Anyway, qualifiers aside, let's build the scene. Normally, as an asexual guy (bi was the closest option as I probably might if certain someones asked; more for their enjoyment than mine), it's not so much the sex part of porn that does it for me as much as it is the scenario; imagining myself in it. Even then, watching it largely doesn't inspire much beyond jacking it; either right then and there or later.

This time was different. The video was of a fem-masked sissy exhibitionist strolling the streets at night, with either her rubber tits hanging out or making it clear there's no panties under that cheerleader skirt. Minus the occasional bit of fondling (and the payoff at the end), I guess some would think it boring.

But I got ideas in my head. Maybe it was the rubber? Or the slutty outfit. Or both? Who knows. I just got the notion that, even if only once, I wanted it to be me. I had no fem-mask of my own (yet) and the only rubber tits I have are cheap things mounted to transparent bra straps, but I had ingenuity and a raging boner so... y'know. Had to get creative.

But I cobbled shit together and went for it anyway. Some of the things - heels, stockings, a skirt (cropped to a more 'mini' length), make-up (though my efforts on that front are fucking horrendous, sometimes) and a wig - I already had.

With no fem-mask, I used a masquerade mask instead. To hide the straps holding my tits in place, I wore a dark t-shirt with a hastily-made boob window to make 'em flashable. To cover THAT up (temporarily), I found a bright orange long-sleeve t-shirt, turned it into a elbow-sleeved croptop and literally used a Sharpie to put the word "WHORE" in big block letters across the front.

After a bit of research, I found the perfect, relatively quiet spot; a hundred meters or so away from a freeway on-ramp. Newbie's gotta start somewhere, right? With a secluded path bridging the road to a nearby canal, there was at least a chance of pulling this off. Hiding the ensemble under regular clothes, and thankful of winter making the nights come up earlier, I headed out there.

Halfway down the path, wooden fences and a hinged gate acted as a passing bay for dismounted cyclists. Perfect. Using a backpack to stow my jeans and hoodie and switch my regular boots out for a pair of black heels, I got changed, placing the stuff I couldn't temporarily abandon in a purple purse hanging from my shoulder.

And, after a near-miss from a pedestrian who I REALLY hoped wouldn't head down towards me, I went back up to the freeway-adjacent road. Deciding to save the act of doing a lap around the roundabout that houses the on-ramps for another time, I settled for the road I was on.

There was a hundred yards or so in either direction where the road was surrounded by mostly nothing, but still had passing cars rolling by. Until, that was, what I like to imagine people could only describe as a short-skirted hooker who'd left a New Year's party started strolling along.

My heart was fucking pounding. Cars passing from behind me weren't so bad... but then cars came down the oncoming lane. There was no hiding my short skirt - only just long enough to stop my cock from flopping into view (unless I saw fit to change it) - and DEFINITELY no hiding the traffic-cone coloured, "WHORE"-fronted croptop struggling to hide my tits.

The fact I still had to head back home as if nothing was amiss was probably the only thing stopping me from cumming before I hid my outfit again. Do I wanna do this again? Damn right, I do; especially if I ever get a fem-mask and a set of decent tits of my own (bigger ones, definitely!).

Do I have any fucking idea what would've happened - and what I'd've done - if one of those cars had stopped? Nope.

Am I thinking and fantasising about precisely that right now? Fuck, yes.