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, I had no girl. My ex had just left me, and although I was getting a lot of first dates, I wasn't getting much more. You see...I have...a big cock. It's about 9 inches, and thick as a Coke can. I know what you're thinking, "Gee, I wish I had that problem!" But let me tell you...even though it's better than the opposite problem, it's difficult finding a girl who'll fuck it. Really, really fuck it. My ex was physically built to accommodate it, and we had a fulfilling sex life up to a point. Women like her were very hard to come by.

We broke up, because - according to her - I'm a misogynist and a bit of a homophobe. Give me a fucking break. I like to talk dirty during sex. I make the occasional homophobic slur during road rage incidents. Whatever. I think what really happened is that I wanted anal and kinkier sex - whips, chains, piss...I just wanted to cross that stuff off my bucket list...and she wasn't into it. Maybe I pressured her too much. She left me for some nerdy-looking, fucking book reader.

So there I was, at home late on a Saturday night, drowning my sorrows after getting tossed out of a date's apartment. We were going for it, and I pulled my rod out. "No WAY am I putting that THING inside me!" I got pissed...we were so close... I asked for a blowjob. (I was drunk, and maybe "demanded" is a better way to put it.) She told me to take a fucking hike. I guess I have to work on my delivery.

I was pounding away my beer, and starting to stroke myself, and I heard music turn on upstairs. Then I heard someone dancing...in high heels...Now...that's a very distinct sound. Sometimes men's shoes can sound like that of course...but it really sounded like someone was sauntering around in heels...Did Ashton get lucky? Was there a chick up there? I didn't hear an accompanying pair of footsteps. Click click click...

Normally, I try to be cool when it comes to noise complaints, but it was late, I was smashed, and extremely frustrated. I just wanted to beat off and go to bed. I debated pounding on the ceiling - which would've worked - but I decided to go up instead. Good neighbor, y'know.

The music was pounding. Some 90's techno beat with a sexy voice taunting and challenging the listener, "...suckin' on my titties like you wanna be callin' me all the time..."

I was steaming as I reached his door. The beer had made me surly, and I was ready to be aggressive. Normally, I didn't have to be. I'm 6'5, and built like a linebacker. I can stare at a motherfucker, and they're going to back down. On this occasion though, I felt adding a little intensity into the conversation would solve this problem once and for all.

Gripping my beer bottle, I was about to knock on the door when a breeze seemed to blow it open a little. The aperture was wide enough that I got a decent look inside, and what I saw rooted me to the spot.

There, in Ashton's living room, was an extremely hot chick in a tight maid's uniform, sinuously writhing to the music.

I 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 music down a little bit." She did. "Come over here and give me a fucking lap dance."

She started walking towards me, one foot in front of the other. She could really walk in those fucking heels. I took a pull off my beer and spread my legs wide. My cock was straining at my jeans. She put her arms on either side of my head and started swaying with the music. She put her lips within a fraction of mine and breathed out a sweet wisp of air. She turned around and lightly rubbed her ass on my crotch in a slow, circular motion in rhythm with the music. For a moment, I contemplated those the dichotomy between those silk panties and my duck canvas jeans. Rough against smooth.

I reached down and pulled her thighs apart...they were so smooth...like a woman's...what am I saying...she was a woman...

I moved my large, calloused hands all over her, and clasped her ass. I dipped one hand inside her panties and felt her cock...it was small, and I gripped it roughly...rolling her balls in my hand... Still with her back to me, she rested her head on the hollow of my shoulder and moaned softly...Whatever perfume she was wearing smelled delicious...I closed my eyes and wallowed in the moment...

Then I reached back and pull her hands apart from behind my neck. I firmly pushed her down on her knees and grabbing a tuft of hair under her wig turned her until she was facing me. She looked up at me, unafraid.

"Suck my dick." I commanded.

She smiled and stroked my bulge through my pants. Squeezing it, running her lips over the rough fabric.

"Take it out. Now."

She went to work unfastening my belt, unzipping my pants, and struggled to pull it free. When she finally orchestrated its release, she let out a gasp. It stood there towering like a monolith.

"Oh my god."

"Do you think you can handle it?"

Her eyes widened briefly, and a hand went up to her mouth.

"'Cuz if you can't, me and your boss are gonna have a conversation."

She smiled again and licked her lips. "I'm sure gonna try daddy..." When she said the word "daddy", a jolt of electricity went through me. I was going to fuck her brains out.

"Lick it."

She smiled and went to work. She ran her tongue up and down my cock, taking time to lick and suck my balls when she got to the bottom. Finally, she positioned herself across my lap and began to swallow. Or rather, attempt to swallow. She put in a good effort. I could her slurp, gag, and gasp as she tried to work my dick down her throat. I decided to help her.

I forced her back on her knees again and got up slowly. I started pushing my cock into her mouth, and just when I felt like she couldn't do anymore, I pinched her nose shut - her mouth opened up a fraction wider and I was able to force the rest in.

"Mmmph mmmm mmmph!" she wasn't frantically struggling or anything, so I figured she was ok. Drool started pouring out of her mouth and her nose was blowing bubbles. I kept fucking her windpipe. Ahhh. This was what I needed. Sweet, sweet relief. I kept sawing away, and then I felt my balls tighten. I stopped. No, no. I wanted that ass.

I slowly extracted myself, and she collapsed to the floor. She was breathing hard. Her lipstick was a bit smeared, and her face was shining with drool.

"Was that too much?"

"NO daddy. NO. I LIKED it." She grinned, and with a finger wiped off the drool from her chin and licked it off seductively, all the while, maintaining eye-contact.

Goddamn. What a little whore.

My next thought naturally, was the bedroom. This little bitch obviously liked it rough, and now the firm king-sized bed made sense. It was an arena for sex. And just as the thought of that bed crossed through my mind, another image appeared in my mind's eye.

"Hey."

"Yeah?"

"You never had a fucking dog, did you?"

"Huh?"

"The leash. Get that fucking pink leash! And the collar!"

She started to stand, and I firmly said, "NOPE. Crawl. Crawl and get it."

She gave me a seductive look and turned on her hands and knees. As she crawled towards the bedroom, she wiggled her ass. God, I wanted to pop that thing.

Eventually she returned, with the leash and collar in her mouth. What a fucking slut. I took the leash and collar from her and secured them around her neck.

"Alright. Good girl. Take me into the bedroom."

God, what a scene. Me leading a beautiful chick, dressed in a leash and collar, on her knees. The fact that she had a little dick swinging between her legs, made it all the hotter. (That thought poked out at me for a second, but I pushed it down.)

"Get on the bed." She crawled up onto the bed, and still on all fours, turned her head around to look at me... "Daddy? Fuck me in my pussy...please..." I shucked off the rest of my clothes and knelt behind her. I gave her a resounding smack on the ass and grabbed her little clit. I gave it a little squeeze, and she gave a little yelp.

"You're not sounding convincing you little whore. You think you can prance around like a slut with your tiny clitty, and expect me to give you the gift of my cock?" I pulled my cock back and let it slap down on her raw ass cheek. "If you want my dick. You need to beg me."

"Daddy pleeeeeeeease...give me your cock...I need your hot dick inside my pussy..."

I shook my head. "I'm still not feeling it."

"Please daddy!" She moaned this time, with real feeling. "I really need that dick in my guts daddy...I need you to fuck me!" Her voice rose to a whine. "Pleaaaase......daddy pleaaase..."

If I was going to fuck this bitch, I needed some lube. She was one step ahead of me, and from the bedside table she produced a large pump bottle. As my eyes adjusted to the light, I noticed her bedstand held an array of butt plugs, from large to very large. I filed that away.

I pulled her panties down to her mid-thighs. I wanted her to feel a little restrained as I fucked her. I let a dribble of lube cascade down the cleft of her ass towards her hole. When it touched her skin, she jumped from the cold liquid. I worked a finger in, then two, massaging in the lube. That wasn't going to do it. I pumped some more and added a third finger. She moaned with pleasure...

"Alright."

I smacked her ass again and roughly pulled her cheeks apart. You could tell her pussy had been used - whether by her own hand or someone else's, I couldn't tell.

"You're mine now bitch." I smeared my cock with more lube and positioned it on her cunt-hole. I rubbed it around and around, until finally, I started to ease it in. I was about 25% of the way in, when her breathing got a little deeper. 50%, and that deep breathing got a little more ragged. 75%, and she was breathing in short, sharp panting.

"How does it feel cunt?"

"Oh.... ohh...daddy...it's so big...I.... I...I feel so full...so, so, full."

With that, I slid the rest in.

"UNNNNHHHHH!!!!" She was convulsing now...I let her acclimate for a couple seconds, then I started pumping. It was a little rough going at first...remember, I'm a big guy, and this is even a lot for a pussy...not to mention some slut's asshole...

"You're so fucking tight..." It felt like I was fucking a rubber band around my dick, but that would change with time...It was different than a pussy...but a hole is a hole, meat is meat...and sure as fuck, my ex would never dress up in a maid's outfit for me...

The lube was sufficient, it was hot and wet and as my balls slapped against her, I could hear her balls slapping in motion too...her thighs were dripping with lube, and our mingled sweat...

I grabbed both corners of her mouth in a fishhook as I plowed into her. We were in a powerful riding rhythm now...I thought I was going to tear her mouth apart, but I needed something to grab onto. My dick felt so good sliding back and forth inside her. She was loosening up for sure. "Jerk off for me!" I shouted.

She reached down and started pulling on her clit. She started jerking furiously as I pounded away at her.

"How does it feel to jerk off while I fuck you!?"

She couldn't really talk, but she let out some animal-like grunts.

"Good girl. Good bitch." I managed.

"Unnnnhhhhh!!!!" She was starting to come. I must've been massacring her prostate. I could hear spurts of cum jet out of her clit, and her walls flexed convulsively around my cock. "Daddy.... Daddyyyyy.... I'm cummmmiinnnnnnngUNNHHHHHHHHHHAAAAAHHHHHH!!!!!"

She came, and started shuddering, the action was so hot, that months and months of pent-up frustration exploded out of my cock head...I could feel torrents of cum bursting into her pussy...She kept moaning too, and I roared. I clutched her ass tight against me, until there was no come left, and I was convulsing too. Finally, I slumped over her.

I started laughing. She was still wearing that fucking pink leash.

I pulled out and marveled at the gaping wreck of her cunt. It was a bit prolapsed and seemed like it was breathing and drooling out cum. That, and lube slid down her thighs and made a deep, rich puddle on her bed. She was panting, and staring at me...

"Was I good daddy?"

I pulled her up by her leash and shoved her face down into the puddle. I scooped up some cum and rubbed it on her cheek. "Yes, cunt...you were fantastic..." I scooped some more cum into her mouth, and she eagerly licked it from my palm...My eyes settled on her butt plugs...I stood and took the largest one.

"I think you can handle this one now." It didn't take much effort to secure it into her pussy. "Keep that in there until tomorrow. Send me a video tomorrow morning of you removing it, and all that cum sliding out. I'll know if you cheat."

"Yes daddy." I yanked the leash towards the floor, and she came with it.

"Walk me to your toilet." We set off in a leisurely pace towards her bathroom. God, did I have to piss. Mountains of piss inside of me from all the beer. She guided me to the toilet and sat back on her knees, looking at me expectantly. "I need to take a piss. So, you can hold me and aim for me, or you can let me use your mouth as a toilet."

Her eyes brightened, and she smiled again. God, what a little prize this one was. She took my flaccid cock in her hand and gently guided it towards her mouth. She opened it.

"Ahhhhhh!"

I pissed into her face. Some of it went gurgling into her mouth, running out of the corners down her face. Sometimes the stream wavered as I doused her pretty face with it.

It was an Austin Powers piss, and felt like it went on forever. When I was finished, I reflexively went to wipe it off with some toilet paper. "No!" she cried and took me into her mouth again. Lord, I have no idea where my restorative powers came from, but she coaxed the last bits of cum from my body, leaving my legs trembling, and feeling like I didn't have an ounce of fluid left inside me. I pulled her up by the leash to stand in front of me. I held her tiny body close against me and swirled my tongue inside her mouth. I could taste cum, and piss and a hint of sweetness. I wanted to fuck her again, and again, and again. I could feel her start to stiffen again...