Free Shoes

"Lift your leg up on the sink and pull your panties down again. I like to watch you submit," the voice behind me commands. I didn't intend to go this far. It was supposed to be harmless fun. But as my throbbing cockhead rests against the cold of this stranger's bathroom sink and I can see my high heel dangling off the edge of the counter, I find myself helpless to say no.

I suppose it all started with my last business trip. Some crappy little hotel in the middle of nowhere with no Wi-Fi, no porn, and a constant business associate in a shared motel room. Back to jerking off in the bathroom twice a day like I'm a teenager again. Things internalizing, twisting, growing.

Three weeks on the road and something snapped when I finally got home. The comfort and freedom of being alone and safe in my own apartment combined with a stack of cash and nothing to do. A few celebratory drinks and a dig through the toy box for 'one last time.' Fresh ice, another pour of bourbon and I'm on CraigsList trolling through 't4m'.

The ad I placed was simple, "Free Shoes to a Willing Playmate." I kept the text of the ad short as well. "Getting away from crossdressing. If one of you gurls is willing to play with me for a short while, I'll give you my size 14, five inch stilettos, my thigh highs, dresses, etc. Not looking to top or bottom, just into a bit of safe, sane play. Email for details".

I don't know why I even bother because I always end up chickening out. It's a small town. I don't want to give away my name or face. I don't want to wake up dead in someone's trunk. I don't want to keep wearing women's clothes and whoring for cock.

But yet...

I checked my email over and over again. A reply appeared. "Would love some shoes. What kind of play?" It was signed 'Debbie'.

"Hi Debbie. Simple deal. I like the feel of a high heel in my ass. A cupped hand spanking my balls. I like my nuts squeezed hard while my ass gets toyed with my big vibrator. Not a big pain freak, just like the humiliation. I'm willing to return certain favors if it suits you... happy to degrade you if you like that or fuck you with your toys. But not looking for anything unsafe. Whadya say? Want some new shoes?"