The Loophole...?

Authors note: you shouldn't read this if you don't like it. Anonymous commenters will big ignored. Likely no sequel anytime soon. Other, unrelated, stories forthcoming.

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Auto-pilot. That was what I was – it's also the dream I sold that filled up my fat wallet.

You've seen the commercials, the videos – they hype is real. We're going to put your lazy, ADHD ass in a car and we're going to drive you around because you can't figure out how to respect each other on the road. Your blood curdles when people don't use their blinkers. You're too distracted on the road, checking update after update in your social feeds.

So we're going to lock you in a car, let you speak to it and you can sit down and drink your little latte and watch your choice of 'good morning' shows or take earlier meetings for the over-achievers out there.

And you'll pay for it and then you won't be able to live without it. Then we'll create easier traffic patterns... if you're willing to pay more. But right now, we're mostly proto-types and nicely edited videos backed up by someone who works 80 hours a week and can turn the ability to charm on and off for clients.

It was easy to work. The market segment spoke to me. Auto-pilot. That's what I was.

Approaching four years of just work and no-burnout. It was the only way I could survive. Function. Work was my goddamn breath. Didn't look at anyone, didn't try. I was in dead-end marriage – woke up every day to a woman who wouldn't touch me; we had a pre-nup but it was a bad one (for me) that her father (a lawyer) wrote; that should have been my only sign needed –but I was young, dumb and chasing the only pussy I knew and when she shut down emotionally, physically and slowly ignored me I learned to live autonomously; I was locked in and I had too much to lose with what I had earned in my career. I learned to go through the motions and live with zero expectations.

It changed for me this year, this week – just a couple of days ago.

Stuck in traffic. Road construction and road mergers in Connecticut – what a surprise. I stopped at one of those little Subway's off of the Merritt. Held the door open out of courtesy. I don't usually do double-takes but I knew my dick would get me in trouble. One can only masturbate so much before the need takes over.

Maybe 5'7", curvy in all the right places but it was the eyes –powerful, fun, curious dark brown eyes that were fucking magnetic – it just happened that she was one of the hottest women I'd ever seen, dressed up in a power business jacket and skirt but with high boots. Just a peek of skin, nothing slutty – all class and power. I'm sure she caught men and women looking all the time. Fuck, anyone with a blood pulse – and it was nice to feel I still had one. She did say thank you, as she half spun and caught me gawking but kept moving to her car. I blushed, waved and uttered something like 'no problem' but made my way back in for a nice, stale sandwich.

I made my way back to the car, eating as I made my way down to the Stamford Marriott. They knew me by name, I got all kinds of perks and frequently met CEO's and hedge fund managers there.

I eventually did make it there and made it with about 30 minutes to spare before drinks with a big investor. I was checking in and caught from the corner of my eye but the one woman who had made my heart flutter in about 1400 days.

She winked at me. I tried to wave her down but heard 'next' and I was checking in. I dropped my stuff off, cleaned up and made my way to the bar. Checking my watch, I ordered two Weller's – straight up – and waited for my investor.

"What's the celebration for?" He said once he had arrived and took the first sip.

"The good news you're about to share with me." I lightly joked.

"What makes you think that is the case, Barry? We haven't committed anything, the buy-in is quite high."

I knew where I could go to, what I needed and when he drew his line in the sand, I knew I had him. The number he said he couldn't go beyond was way higher than my low – I did everything I could to look beaten.

I rolled my eyes, "Okay, okay, okay – Steve – I'll get my ass chewed on this one –"

"Sounds good to me." My mysterious woman said as she walked briskly by.

"Ha! Did she say what I think she said?" Steve chided.

My game was thrown off – I was envisioning her bent over the supple leather couch in my suite and me worshiping that rough coffee-ice-cream colored ass. My pants were tightening.

"Tune-in Tokyo. Barry, you okay?" Steve added after a moment.

I shook my head but didn't comment on the vixen. "As I was saying, Steve, they're not going to like this –but I'll stick my neck out there and guarantee your firm will have the contract with the numbers ready for your counter signature on your desk in the morning."

"One day you'll win out, Barry, but great doing business. We have high hopes for this one."

He stood and we shook hands, firmly and he was off. I texted my secretary and legal teams and they got it to his office that night. I loosened my tie, undid my top button and plopped back in the seat lifting my drink to my mouth and sipping the smooth bliss. I craned my neck looking for her but couldn't find her. I finished, tipped well and took off for my room. I ordered room service and updated the executives. Prematurely calculated my commission and prepped for the next day.

It was late by my standards, 10:30pm, but I was awake – distracted – thinking of things other than work. Thinking of events that would leave me panting, hopefully her panting – but I couldn't. If my wife found out, she'd get everything. I couldn't afford everything. I swear it was her plan to drive me away. To make me end it and walk away and kick her feet up until she could find another victim. Part of me knew I needed to end it early, cut my losses and move on –but I was stubborn. I needed grounds for divorce to maintain the nest-egg I had built and I didn't have any grounds.

I went to the gym. My one hobby. I wasn't ripped like I was fifteen years ago but I did okay. I took the elevator down and went to the glass room. It was sprawling with different areas cornered off –like it had once been all conference rooms but blown out for a big gym with some privacy.

I had my headphones in, jamming out to some old-school Beasties and hit the weight bench, working up one heck of a sweat. I went to get some water and a towel to wipe down my bench. As I turned, she was there – had been for who knows how long –watching me.

"We have to stop meeting like this." She said huskily – beads of sweat on her gorgeous, oh-so-soft looking skin – eyeing me up and down.

I laughed, enough anxiety worked out of my system to extend my hand and introduce myself as I eyed her back. I tried looking in the mirrors to get a better look at her grey-leggings covered ass – it was thick, bubble butt - not spilling over – not cartoonish. But I was a little perplexed at what I saw. There was, right where he butt-cheeks where coming together a little, barely noticeable bulge.

"Do you get lost often?" She said with a sheepish smile.

I recovered quickly, with a little laugh, "Oh, I see you were spying on my earlier at the bar?"

"What can I say, I have a type." She flashed her eyelashes.

Laughing, I said, "What, a walking, talking average-joe?"

"No, I like ones that try so hard to not notice me that they can't help themselves."

"Are you telling me it wasn't chance?"

"Once I saw you checking in, I wanted to ensure I solidified the impression I had left when you held the door open for me."

"Well, you are hard to miss."

She winked. "I know, just like how I know you haven't missed anything about me, either."

"What, what do you mean?"

"Look, let's level –it's 2018 – you're an adult, you've checked me out in the mirror, noticed my luscious ass and that I have an extra bulge back there."

"What? Firstly, I ..."

She cut me off and walked closer... a finger to my lips to silence me. "Your wife isn't here." Her other hand grabbed my left hand and fingered my ring.

"I can't."

"But you want to."

"I don't know what I want."

"Well, I do. I know what you want. What you need." She stopped, let go of my hand and then rearranged her 'package' "And I know what I need," with more emphasis and her brown eyes staring me down and then whispering in my ear, "what I want." My eyes were closed, enjoying the moment, nervous, getting hard and slightly confused about my reactions and lack of them.

She kissed me on the cheek.

"Room 2141. I'm here all week." She slipped a business card from out of nowhere into my pocket. "Text me when you realize you want it." She said while rubbing herself, lewdly, I blushed crimson and stood motionless except for my hardening package.

She turned and walked out of the room. He globes bouncing from side to side. Her skin was smooth, silky and like coffee; she smelled sweet and with a hint of musk. Her dark hair in a ponytail, athletic and fit with a top to match –devilish, deep eyes and smile to match; my senses were on overdrive. I'm lucky I didn't faint and fall down straight on my erection.

I didn't know how to act, react; didn't know why my erection wouldn't abate. I was battling, called my workout short and ran the stairs up to my room, room 2142. I was exhausted and breaking out in sweat again, breathing hard.

I must have starred at the door for five minutes. My room, her room, my room, her room. The decision shouldn't have been that difficult. I heard the elevator ding and to not look like a creeper, I slid to move my key to the door. It buzzed open with my hand on the handle, pulling it down and ready to step in.

"Barry, you're my neighbor? How convenient." She said teasingly as she made her way to her door. She eyed me up and down and I watched her. Her smile coquettish and me flabbergast.

30 minutes later, after a cold shower where my dick wouldn't shrivel up and my thoughts couldn't escape and my balls reminded me that I hadn't ejaculated in a hole for literally years, I found myself knocking on 2141.

"Can we talk?" I asked, for the first time recognizing I wasn't making consistent eye contact and trying to correct it.

"Sure, Bear." She opened the door.

I cracked. Laughing, "Did you just give me a nickname?"

She was out of her gym clothes in just a long tee, smiling.

"Look, I..."

"You don't owe me anything Barry. I can tell you're a sweet guy going through something."

"It's rather not complicated – I just can't give Satan – i.e. The Wife – and ammunition. I'm trying to get out of a long-term disaster and I can't have her knowing I've slept with a woman –let alone a beautiful one."

"You know I have a dick, right?"

"I, I don't care what you have. I just know I'm thoroughly attracted to you and that I want to get to know you better."

She was silent, she stood and hemmed up her shirt. My eyes naturally progressed down to her crotch and there was a sizeable dong. She watched my face as I gulped realizing the sheer girth of it that it wasn't going to me average like me.

She raised an eyebrow.

"I don't care what you have." I repeated. "You're obviously intelligent, just the right amount of devilish, funny and damn I want to kiss you - but I've got a wild pre-nup that says if I have an affair with a woman I lose it all."

She pulled her panties down. Revealing a half-hard and thickly growing uncircumcised dark cock, she stroked it slowly.

"For a smart guy, you're certainly missing the loophole, here." She said referring to her cock. She took a pace towards me. Maybe she was right and had a great point; the document only stated woman –inferring vagina, not necessarily cheating. Maybe my confusion was getting in my own way. Maybe I just needed her to take charge and she knew it. Maybe the money didn't fucking matter whatsoever. Love is all you need. What the fuck was the Beatles doing in my head?

She kissed me. Soft, supple but firm. I melted and she moaned and then I moaned. She snaked her tongue deep into my mouth and grabbed the back of my head.

"Enjoy it."

She pushed me on the bed and kissed me, I was putty in her hands as she crawled atop me. I could feel her heavy cock pressed up against my left, slowly grinding into me. She unzipped me, snaking my pants to the ground she slowly enveloped my cock, taking the whole thing in one swoop – not gagging or complaining – she was tight and warm and I'm after a few minutes I told her I was going to cum. She didn't stop – bobbing and I couldn't hold back.

"Fuuuucckkk," I screamed as I ejaculated a torrent of cum down her willing throat.

She crawled up my body, I lie there, panting as she started snowballing me. As a complete square, this was another new experience for me. The taste, the texture – it really wasn't all that bad.

"My turn." Huskily, matter-of-fact. No second guessing what I needed to do. Usually, once I come, I'm done - ready for bed. Not so.

I stared up at those urging eyes and obeyed. It was easy to obey. To just do what she said. I kissed down her neck, and removed her shirt - her tits firm, filling up my palms and stopping at the nipples to tug with my teeth gently, licking the wide nipples. Her tummy was taut as I kissed my way down, still a little salty from the gym - she hadn't showered. I loved the taste as I mouthed her navel. Her hand on my shoulder, insistently but slowly, nudging me down. I was at her panty line - nothing racy, just some white cotton boy-shorts - they accentuated her hips and my hands moved down to cup and kneed them. My teeth on her panty line - and grabbed my head and smeared it onto her panty-covered cock.

"You want it, don't you. Enjoy the feeling of my hardness."

I was getting butterflies - I don't know why but I was yearning for it so bad. If I had a twat I'd be creaming my panties in anticipation.

She kicked off the panties and pulled out her dong. Thick, uncut and shaved. Not too veiny.

She slapped me in the face with it and then pulled my head and nose to the base.

"Smell it." I inhaled deeply, smelling her musk - she was still a bit moist from sweat.

"Good boy. Now, get to work." It wasn't an option, the decision was made for me.

I started off by kissing where I was already positioned - at the base of her cock. Her nutsack was loose and I pivoted down there to first gently kiss, then tongue and then suck on her nuts - something I had already appreciated. Then I wrapped my left hand around her shaft as I continued to lap at her balls.

"You must have done this before." I shook my head 'no' and she was surprised. "Make love to it."

I positioned my mouth at the tip, pushing back her foreskin and licking the pink tip. I took her in my mouth and bobbed up and down, up and down, jut a few short inches - adjusting to her size, to her sticky salty taste and slowly working my way down, a quater-inch at time. I was bobbing. Up. Down. Up and down. Feeling the weight of her ballsack as it slowly tightened. I knew she was building a load for me. I knew she wanted to cum. Her hands were insistent, forceful but it was relieving to have the guidance as she used my face. Humping me back as I made my way down her thick shaft. Her moans grew louder. She was getting urgent but I still couldn't get more than three quarters in.

She started taunting me.

"If you can't get it in... I'm just going to have to find a deeper hole to put it in."

I moaned My asshole clenched. I looked up at her, my mouth full of cock. I stroked her base harder and then lapped at her nuts, trying to make her cum. I wanted her to cum and cum hard and spurt her white seed.

She pushed me off, smacked me again with her cock.

"Bend over the bed." A demand, an expectation.

I won't lie, I'd been known to finger myself in hotel showers - being able to get two fingers in - but never anything like this. She departed for a bit and then returned with a small tub, unscrewed the cap and dipped her fingers in generously. Applying it to my anus, she worked it in.

"You know what's coming, right? You know this is going to change you. Make you mine. When we're done, you'll complain about being empty - you'll beg for me to shove it in there again so you can feel full. So you can feel complete."

My cock was drooling on the hotel bed as she started teasing my hole.

"I knew you'd be compliant," she said as she worked her thick head into me. "I can't wait to breed your little ass." She spanked me. I was looking over my shoulder, my arms back, spreading my cheeks without her even asking. Hot, cute - snickering at me a little. Her left hand on my hip, her right hand at the base of her swelling cock, slowly pushing into me. There was some burning, and unintended clenching, which she spanked me for. She pushed in, then pulled out, maybe an inch at a time - deeper and deeper - I was moaning.

"Bitch is in heat. Bitch wants my seed. I'm not even halfway in, Bear." She pinched my ass and I yelped but somehow relaxed my anus and she slid deep. To the base. Her big balls rested up against mine. A little pain, a flood of pleasure. Her cockhead on a button I didn't know I had. My cock making she sheets wet.

"Oh, fuck, you tight little whore. You dumb little cocksucker. Your wife knew this would work."

"Wha- what?" I mumbled.

"She set this up. She knew you couldn't resist me."

I could see she was filming this with her phone.

"Now she gets half your money and I get your ass. How do you feel about that?"

I should have been mad. I should have felt exposed.

Between breaths, "Don't stop... don't stop fucking... fucking me."

"I wont'." After a pause. "You're mine. Your boi-cunt is mine."

She sped up, slapping my ass and slammed in deep. I felt her hot cum jettison deep up my anus. I was panting, sweating, tired.

"I don't care... just... just don't pull out."

Her softening cock pushed in deeper and we cuddled up on the bed.

There are worse ways to lose a fortune.