Sissy Maid Blackmail! - Sex Stories

Sissy Maid Blackmail!

... nearly dropped my beer. I stood and watched her for a minute, my dick stiffening in my pants. I don't know where Ashton was, but holy shit...even if he is here, a slut like that would probably want to give me a BJ! (Drunk logic. I know.)

I slowly eased myself into the apartment, careful not to make any noise. There was only one dim light on so it was easy to stay hidden. Besides, the music was covering any sound I was making with my feet. This girl had her eyes screwed tight and was chugging a White Claw while she danced, obliviously.

I took it all in. Shiny black latex maid's outfit. The white fringed skirt barely covered her ass. Her red panties were a pop of color as they revealed themselves with the gyrations of her hips. Garters and black seamed stockings clad a pair of coltish, well-shaped legs, which ended in a ridiculously high pair of shiny black stripper heels.

Still obscured by the dark, I kept watching as she spun around mouthing the lyrics ("Fuck the pain away...fuck the pain away...") and I was starting to think about those bright red lips around my cock. She had very small, budding, perky tits inside her corset. Her hair, capped off with an old school French maid's headpiece, and tasteful bangs offset Ashton's smoky eyeshadow -

- Wait a minute.

"ASHTON!?!!!!??"

His eyes went wide and he screamed "AHHHHHH!" so abruptly, it startled me...

"Your door...you fucking door was open..."

Once again, the color drained out of his face. I could ...

... guess what was in that mystery box now.

"Holy shit! Is that YOU!?" I started laughing. I was having a shitty night, so I was feeling cruel. "Holy fucking shit. It is you!" I started to really bawl with laughter.

He was mortified and stood as still as a statue.

"Holy fuck. Wait 'til your boss hears about this..." Still laughing, I took out my phone and snapped a picture. The flash seemed to shake him out of his reverie.

"WAIT." He said. His voice was so authoritative, that it made me stop. Then his body regained its composure. His feminine composure, I should say. A smile lit up his face, and he slinked over to me. Her. A smile lit up *her* face. She got into my personal space and traced a finger from right below my collar bone, down my sternum towards my belt. My head was swimming, my heart was pounding. What the fuck was happening.

"Maybe," she cooed, "Maybe we can strike a deal..."

Like my ex said, I'm a little homophobic, but my dick had other ideas. My Meat Log was starting to become tumescent. Months and months of frustration was welling up inside me. I could feel myself break out in a sweat...Through the haze of alcohol, I squinted...Was it gay if the person you were fucking was dressed like a girl? Of course not. Drunk logic.

My composure returned, and I affected a sneer on my face. She was going to have to work for this. I looked her up and down dismissively.

"Maybe." I said. I turned my back on her and sat down on the couch. "Turn that fucking ...