Sissy Maid Blackmail! - Sex Stories

Sissy Maid Blackmail!

I published this story under another Literotica ID: MonkeyWrench00. I'm sharing it here too. (I use this ID for a more feminine persona when I chat. If you see me in the CD chat room here, hmu!)

This story was inspired by a chat between myself and ashleycdgurl. In essence, it's a collaboration. Without her, this story wouldn't exist. Thank you for being a muse!

Also, I hate proofreading, so, if anything is weird or doesn't make sense, apologies. I just wanted to get this out there.

It began several weeks ago when new tenant moved in directly above me. I'd seen him moving his stuff, struggling with boxes up the stairs with no one to help him. Wanting to be a good neighbor, I offered to help. He was a short, slim young man, with a clean, fresh-looking face. Not a hair, or bit of stubble on it. He must've been right out of college or near to it.

I offered my hand and introduced myself. He said his name was Ashton.

I helped him lug all his stuff up to his apartment. Fortunately, there was little furniture. Getting the bed up, was a bitch. It was a firm, king sized mattress and weighed a ton. I opined, "You must get tons of pussy to have a bed like this!"

He grimaced. "Something like that." His face flushed. He was a good looking dude. I'm sure he got tons of trim.

I went to grab one of the last boxes, and he shouted "No!" I froze in place as all the blood drained out of his face. Whatever. Take your own fuckin' box bro!

I pointed to another box, and ...

... laughed, "How about that one?"

"That's fine." he said, taking his prized possession. He grabbed it out of the truck, took a step, and went flying ass over teakettle on some black ice. The poorly taped old box hit the ground, and a couple items spilled out. The box itself obscured my vision, but he scrambled to get on his knees and shovel his secret possessions back in. I caught a glimpse of a pink dog collar and leash.

"You got a dog?" I inquired.

"Uhm..." he stuttered. "I used to...They uh, don't allow dogs in here, so I had to get rid of her. I guess I forgot to get rid of the leash."

"Mm." I grunted in acknowledgement, then I put the incident out of my mind.

We got him moved in, and then I rarely if ever saw him. Our schedules were different enough we often missed each other. I suppose he'd leave after I did in the morning and came back a couple hours after I'd get home from the gym at night. Our sub-unit only had four apartments, so it was easy to tell who was coming in and which apartment they went to....You could also tell how many people would come in.

As it turns out, one of my workout buddies was his boss. He didn't have a strong opinion about him. Ashton was competent and worked hard, but he also kept to himself. He'd join the boys for wings and beer on occasion but was generally abstemious. "I've got to keep my figure for swimsuit season." he'd laugh.

--

Now, at this time in my life I was having what you'd call, "girl problems". The problem being, ...