Dude You Slept with My Mom?!

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This is a work of fiction that portrays people engaging in sex and sex-play. The characters are of legal age to consent (18 and over). If you're not, come back later.

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~~~ The List ~~~

I don't remember when I stopped giving a shit about the kids in my class - but it was a long time ago.

I'm sure they'll tell you it was something that I did.

My sister was four years older than me.

Dad was gone; mom worked three jobs - so sis couldn't go anywhere without dragging me along.

I'm surprised she doesn't despise me - but I knew my life depended on her - so I tried to be more of a suck-up - and less of a fuck-up - especially when her friends were around.

For that reason, I had more associates - if not necessarily friends - in her class - than in mine.

By my freshman year, of course, my sister - and her classmates - had graduated.

At that point, I had neither friends - nor associates.

I'd gone to school with these kids all of my life - but it was like I was invisible to them.

That was fine with me.

In 8

th

grade, I got a paper route - to earn some spending money.

A couple years later, one of my customers asked me if I wanted a summer job and - the next thing I knew - I was working summers, nights, and weekends at the nursery.

I was a month past my 18th birthday - on a warm spring day - helping my boss with a big landscaping job.

My shirt was glued to my body.

The lady we were working for had been standing on the deck, watching us, for a while.

"Mr. Reynolds," the woman yelled to my boss.

Since I was helping him unroll sod, I stopped working when he paused to see what she wanted us to change.

"That boy of yours ..." she asked.

He glanced at me and looked back at her.

"Yeah?"

"He 18?"

"Yup," he said, "last month."

"Could I borrow him for a minute or two? I need help moving a bed."

He looked at me - then back at her - and then turned to face me.

"Is she asking what I think she's asking?" I asked him, quietly.

"Pretty sure ..." he said, smiling. "You interested?"

I looked back at the middle-aged woman watching us intently. She wasn't ugly.

Her sleeveless white knit top fit well enough to hug her cushioned middle - but she had a really nice rack.

Most of her lower half was hidden under a flowered skirt. The fingers of her right hand had closed on one of the pleats and she was turning side to side a little - like a schoolgirl.

I swallowed the lump in my throat, "Sure - if she doesn't lose her shit when she sees my dick. The kids at school call me The Mutant."

Out of reflex, he glanced at the balloon growing down my pant leg.

My penis is a little bigger than the national average - 13 inches long and as thick as a construction worker's wrist.

He looked at me, smiled, and said, "Only one way to find out, boy. Best you go see how far you can get that bed of hers to move."

I stood to my feet and started taking off my leather gloves.

He reached out to take them.

"Wash those hands good before you touch her; scrub under the nails," he advised.

I nodded and headed towards the deck - and the woman who was now smiling broadly - and hungrily.

I was barely inside the house before she was pushing me towards the master bedroom.

She shoved me into the room and closed the door.

When I told her the advice my boss had given me, she groaned with impatience, but guided me to the bathroom, turning on the water.

As I washed my hands, she stuck her nose into the sweat-filled side of my shirt and inhaled deeply - then she started yanking my clothes off.

By the time my hands & fingernails were clean, the shirt was the only clothing I still had on.

She gasped when my semi-rigid cock sprang into view, palming my nut sack, and hurrying even faster to get me naked.

She didn't seem scared of the Mutant.

I dried my hands and turned to face her.

Her arms went around my chest and her lips attacked mine.

Since she was hugging me tightly, I reciprocated.

When she released me, she was panting.

She grabbed my shirt, whipped it over my head, tossed it aside, and led me to the bed.

In seconds, the covers were pulled back and she was naked.

"I normally like missionary," she said, "but I'm a little scared of your pecker. Lay down and I'll work it around until it fits. Once you've got me loosened up, I want you to roll me onto my back and fuck me like a dirty whore. Can you do that?"

"I'll try."

"That's the spirit!"

Her right hand gripped my shaft and she stroked it once before stealing another kiss and pointing to the middle of the mattress.

I complied.

She climbed on top of me and lined my cock up with her sex - while I drank her body in with my eyes.

She was pretty hot for a woman who looked almost old enough to be my grandmother.

"It's been a while," she moaned as she worked to wedge my cock into her pussy.

I've watched my share of porn. Sex was usually preceded by foreplay.

There was no foreplay here; she knew what she wanted and she wasn't waiting.

"Fuckkk!" she groaned as she got the head inside and then slowly relaxed to take my meat-monster deeper and deeper.

She still had about an inch left when my knob hit a wall.

"Holy shit!" she moaned. "You're fucking huge!"

She wriggled around and waited for things to loosen up.

"I'll make it fit. I want it all. Fuck! I've never had one this big!"

She ground her hips around in circles.

"Play with my titties some. I need a little more time."

I grabbed and groped her breasts; they spilled out of my hands as I kneaded them with my fingers.

She was moaning.

Her body relaxed a little more and the rest of my cock squeezed inside of her.

Her mons was resting on my pubes.

"Fuck, yes! You're halfway inside of my womb! Holy fuck!"

She started with little strokes - just easing my cock-head in and out of that last little tightness inside of her.

"Fuck! We may have to stay like this - at least this time. Can we do this again?" she asked.

"We haven't even finished the first time yet," I snickered.

She laughed.

"We will - don't you worry. A cock this big should be full of cum. I want it all. Inside."

She stared into my eyes as she said the last bit - letting me know that it was not optional.

She grabbed my wrists and started fucking herself, up and down, on my dick.

Her moans were getting louder - and longer.

The entire length of her vagina seized down on my penis - and then her body trembled - and then she was riding me again.

"Damn! Son! You still okay?"

"Yes, ma'am."

"Good. I want one more and then you can blow your load into my womb."

"You sure?" I asked.

"It'll be fine," she assured me.

Several minutes later, I was approaching the point of no return.

"I'm getting close," I warned her.

She nodded, closed her eyes, and focused - and sped up a little.

The friction - and her moaning - was getting to me.

My hands were still gripping her breasts - and hers were still hanging onto my wrists.

"Ma'am!"

My fingers tightened down on her tits - I hoped I wasn't leaving bruises - but there wasn't much I could do at this point.

"Uhhhhh," I warned, gripping even harder.

"Fuckkkk!" she screamed - her body tensing once more.

She impaled herself fully on my aching cock - just as it started spewing its load - directly into her womb.

She collapsed into my arms and I wrapped her up, holding her against my sweaty body.

There was still a drop or two leaking from my cock - so I stroked, slowly, in and out of her wonderful pussy, encouraging the last little bit to join the quest for her egg.

She shuddered, raised herself up, and kissed the life out of me.

"We're definitely doing this again," she promised, wrapping her arms around my ribs.

She held me for a couple more minutes and then climbed off.

She grabbed her clothes and headed for the bathroom.

"Sorry - but I can't let you shower with me. I took too long already and my family could be back any minute. Throw your clothes on and sneak out quick. I'll be out in a bit to talk to your boss. If you see anybody, tell them you had to use the bathroom."

Thankfully, I didn't see anyone - and quickly ducked back out to join my boss.

"You get that bed moved around the way she wanted it?" he snickered.

"Not quite. She said we might need to try again," I said, smiling ear to ear.

He grinned at me and said, "Nice!"

He handed me back my gloves - which I began putting on.

"Guess you didn't scare her too much."

"She worked it out."

"Out?" he said, snickering.

"... and in," I said, laughing.

We were finishing up the last of the sod when the lady of the house came out to talk.

"You boys almost done?" she asked, walking across the large yard.

"Yup," my boss replied - before being interrupted by a voice from the back of the house.

"Mom! Where are my car keys?" the voice yelled.

I knew that voice. My boss was between me and the house. I held very still.

"Breakfast bar," she yelled over her shoulder, in reply.

I heard the door close but stayed out of sight.

The woman I had just fucked was Brian Jenkins' mom.

"I may have another little job I need done," Mrs. Jenkins told my boss, "in a week or two."

Sounds good," he told her. "I'll send you an invoice for today."

"Perfect," she said. "Add a couple hundred dollars' worth of ... uh ... labor on there - and make sure you split it with the boy."

She glanced at me and winked.

"I can do that," he replied. "We definitely appreciate the chance to help out."

"It's been an absolute pleasure doing business with you gentlemen," she said. "I'm sure we'll be seeing more of each other."

She looked down at my lazy cock, back up to my eyes, and then turned to head to the house.

My boss started picking up tools and supplies.

I helped him clean everything up and get it back in the truck.

"Damn, son!" he said, as we pulled away. "You must've done alright."

"I'm in trouble," I told him.

"You came inside of her?" he asked.

"Yeah - but that ain't it - that kid - her kid - he's in my class at school."

He started laughing so hard he had to pull over to the side of the road.

"I'll talk to her when she calls," he assured me - when he could breathe again.

I nodded. My boss was smart. He'd figure something out.

"She will, obviously, be calling back. I'll give her the info and we'll find a way to make it work. I'm assuming you boys don't get along?"

"Nobody at school likes me," I admitted.

"He's gonna like you even less if he finds out you just knocked his mother up," he said, laughing out loud once more.

I was quiet the rest of the way back to the nursery. I was thinking about what had just happened. That was the moment my Fuck It list was born.

There were 105 of us in my class. We would be graduating from high school in just over a month.

When I walked across that stage - to get my diploma - Brian Jenkins' mom would know my name - and what it felt like when I blew my load in her gripping twat.

There wasn't enough time to get it done before graduation - but - it had just become my personal mission in life - before we got to our five-year class reunion - to nut inside of every mom of every one of my classmates.

~~~ The Plan ~~~

Mrs. Jenkins called back two days later, saying that she couldn't stop thinking about my cock - and asking when we could meet again.

After Mr. Reynolds talked to her, he said he thought she might be a willing accomplice in my scheme.

He and I had worked together for more than a couple years, at this point, and he had become my closest friend and confidante.

I didn't think of him as my dad. My dad had ditched us so long ago that I didn't even remember him - but Mr. Reynolds didn't act like any father I knew. He was more like that favorite older cousin that did all the things your mom forbade you to even think about.

He was the best negotiator and a shrewd businessman. I strived to learn as much from him as I could.

By the next time I arrived at the Jenkins home, I had a company phone and was driving the old landscaping truck - with the company logo emblazoned on the side. It was loaded with bags of mulch - and all the tools I would need to make my visit as inconspicuous as needed.

Mr. Reynolds had told me to wait until I had her panting and then give her all of the details. He assured me that he was confident that she would engineer whatever needed to be constructed to set up a long-term partnership between me & her - with the nursery as a cover.

He was already anticipating that my side of the business - as he called it - would be expanding. He had placed a Help Wanted ad - to replace me at the nursery - and had worked out how I would bill for services.

He warned me to make sure I did enough real landscape work to keep the cover-story believable.

~~~ The Accomplice ~~~

Mrs. Jenkins was in heat. Whatever state she had been in - when we first fucked - must have just been a passing fancy.

This time, she was in need.

I had already given her two small orgasms and she was working on a good one for her third.

Thinking about what I needed to say - and how to go about it - I was barely turned-on - even though her cunt was squeezing the shit out of my dick - and her moans and pleas were music to my ears.

I'd watched my boss operate - and I knew his advice was sound. Show them what you can do, let them start thinking about the possibilities, deliver, and they'll come back every time - with bigger and bigger ideas. Guaranteed success. But. You HAVE to deliver.

I had delivered the first time - and she'd already gotten a taste of what was coming. It was time to set the hook.

"You didn't tell your son about us, did you?"

"You know Brian?" she guessed.

I nodded.

"No, I didn't tell him - but I don't think he would say anything."

"He wouldn't?"

"He knows his father is sleeping with his boss - taking it up the ass - for both business and pleasure - and he knows I'm a vengeful bitch that spreads my legs for any man who'll fuck me."

"Vengeful?" I asked, wanting clarification.

"His father doesn't care - I don't think - but I get my pussy filled as often as I can - preferably in the master bedroom. It's my petty one-fingered-salute to our fictional marriage."

"One-fingered-salute?"

"Yes," she said.

She pulled my lips to hers and kissed me - as I continued to slide my stiff pole in & out of her twat.

"I have an agenda that sounds similar to yours," I told her.

"Which is?"

"I want to cum in the cunt, mouth, or ass of the mother of every one of my classmates."

She looked into my eyes, examining my soul.

"Brian's in your class?" she guessed.

"Yes," I admitted.

She stared at me a little longer, thinking.

"You know what?" she finally said. "I don't need to know the why."

I gave her a quick peck.

She looked at my lips for a full minute before continuing.

"You are the sweetest man who's ever said 'yes' to my request - and I think I'm addicted to this massive cock. Furthermore, I know several of the moms you're talking about - and I'm certain that they would pay money for the chance for you to ring their bell the way you did mine."

She reached between my legs and felt my scrotum. It was stretched full.

"If I'm reading you right, you need help - tracking these moms down - and you'd be really grateful to whoever can facilitate that."

I nodded, studying her face.

"Why don't you dump that load you've been saving inside of me and we'll sit down and talk. I'm pretty sure I have 90% of the contacts to make your scheme a reality. Assuming, we can come to terms, I'll have you fuck me full of your cock-snot one more time before you go - as the down-payment on our contract."

I lifted her ankles, one by one, and set them on my shoulders, next to my ears. Her pussy had been tight before - but now it was even tighter.

She moaned and grabbed her breasts, massaging them.

I grabbed her calves in my coarse hands and started powering my cock in & out of her - driving in hard & fast - pulling out soft & slow.

"Fuck me!" she yelled, urging me to go faster.

I continued what I was doing a half-dozen more times - and then just started fucking the shit out of her.

She screamed my name as her channel started spasming - and I released the cotter-pin that had been holding the flood-gates closed. My fire-hose started gushing inside of my lover.

~~~ The Contract ~~~

Mrs. Jenkins had been the president of the PTO when we'd been younger. She still had all of the names - and most of the addresses - for the parents.

Our quiet, little community had more than its share of broken marriages - but she had records for all of that as well.

We sat at the dining room table and worked together to fill in the missing names. We were, both, still completely naked and she reached over, every few minutes, to stroke my cock - to see if I was ready to give her another fucking.

At her request, I called Mr. Reynolds - who - after a brief negotiation - agreed to bring her into the company as an office coordinator - with a mediocre base-salary - and a 5% commission on every job she secured, once completed. She would handle the billing and the books - and match-up the invoices that went out with the payments that came in.

Up to this point, Mr. Reynolds had been managing the landscaping business as a side-venture to the nursery.

This would establish it as more of a standalone company - but still feeding income back into the parent.

He had just bought a one-bedroom cottage, adjacent to the nursery - mostly to get the sheds and the parking space that came with it.

My next task would be to convert the front rooms into the business space that Mrs. Jenkins would need. The rest of the house would be my living quarters - and the area for my new business partner & I to hammer out the finer details of her commissions - one orgasm at a time.

Brian's mom hugged & kissed me, pinched her nipples, and then leaned down, onto, the massive table, spreading her legs, waiting for me to mount her. This was the same table they ate their Thanksgiving dinner on.

The huge front window allowed the neighbors - and any passing vehicle - to watch - as I lined my reawakened cock up with her slippery cunt - and plunged it inside of her.

"Oh, fuck. Yes! Every time, yes!" she gasped.

I didn't bother with any foreplay, I just fucked her hard until she had climaxed twice - and then flooded her already-saturated twat with even more of my spunk. It oozed out around my cock.

I slid the fingers of my right hand through it and reached under her gap to massage it into her clit. I stuck the thumb of my left hand in the foamy splooge and smeared it across the mouth of her shithole at the same time.

She shrieked and jumped - and then started spasming - as her third orgasm overtook her.

I continued to piston my softening sex-organ in & out of her sloppy pussy until her breathing returned to normal and she yelled at me to stop.

When I pulled out of her, a huge glob of semen gushed out of her quim and splattered on the dining room floor. She ignored it. She turned and took me into her arms - her beautiful mammaries smashed against my bare chest as she kissed the air out of my lungs.

~~~ The Office ~~~

It took me a week - interrupted by a couple more visits to Mrs. Perkins' house - to get the new office looking the way Mr. Reynolds wanted it.

It had a desk, a computer (loaded with all of the software she would need), massive pictures of some of our previous landscaping work - mostly from the house that I'd spent the majority of the last month at - and all of the furniture and equipment our new office coordinator would require.