Dude, You Slept With My Mom?! Ch. 01

I'd only fucked two moms so far. One hadn't had sex in years - and the other was fairly promiscuous - at least until she met me - but most of these ladies were probably being pretty careful about their health. I mean, they're old, right?

I laughed at my own thoughts. Old or not, they knew how to fuck. Even if I caught a disease and my dick rotted off, I was in for a hell of a ride before this was over!

~~~ Week 3 - Amelia Adams (#3) ~~~

Amelia's mom, like Donny's, was another regular at Maggie's house for coffee & cards.

Maggie informed me that Mr. Adams was not keeping her happy. She didn't go into details but she assured me that the only risk with this one was that I'd have another regular customer to add to my roster.

Mrs. Jenkins and I had already talked about that concern - in addition to keeping me safe from STDs and avoiding kids.

She had bought me a truckload of condoms and - as much as I didn't want to - I had agreed to wear them religiously unless she had cleared both the woman and the window.

So far, she hadn't been wrong. I'd only been at this a couple weeks and I was already almost 2% of the way to my 5-year goal. At this rate, I'd be done in two years.

Mrs. Emily Adams didn't want to use the condom but Maggie said this was not a safe day - so I was supposed to wrap it before I tapped it.

Actually, Amelia's mom wanted to be on top - and I was free to occupy my hands however I liked while she fucked herself silly on my willy.

Her tits were a little deflated - but the nipples were hard as hell - so I rolled them between my fingers - and tugged on her ass-cheeks - as she slid her tiny body up & down on my rod.

She was both shorter and skinnier than her daughter. It was kind of weird.

I didn't even cum. She worked herself through three orgasms - the first one coming just from the head of my cock bumping her cervix - and then she climbed off my cock and thanked me.

She dressed quickly and headed out front.

We didn't get another landscaping job out of the deal but she had left a cash gratuity with Maggie on her way out, telling her friend, "Thank you," and asking when she could come back.

~~~ Week 3 - Yana Georgieva (#4) ~~~

I'm still not sure Yana's mom even spoke English.

She, obviously, knew Maggie, though - and she'd been cleared for raw sex.

She was a take-charge gal. She shoved me back, onto the bed, climbed between my legs - and sucked my beef-stick halfway down her throat. She stayed at it until her eyes were watering.

She, then, turned her back towards me, skewered her pussy with my cock like she fucked one this size all the time - and then laid (face forward) on the bed - grasping my ankles - and then slammed her stomach into the bed - pistoning my cock along the back wall of her vagina - before raising herself up - once more - to repeat the grinding strokes. The stimulation - from the head of my dick being repeatedly smashed against the walls of her vagina - set me off quickly - and I pumped a big load into her.

She moaned - and then fucked herself on me a few more times - before climbing off and getting dressed.

~~~ Week 4 - Emily Hall (#5) ~~~

Maggie told me that we were still working our way through her "inner circle". She said that my exploits were now the main topic of conversation for their get-togethers.

When I walked into the front office she smiled and said, "You won't need the mask today - but - I will warn you now - today's client will know who you are whenever she's close enough to hear your voice or smell your scent.

That last part seemed weird - but I was definitely intrigued. I eased into my bedroom to find a woman with sightless eyes reclining on the bed. I paused.

"I'm so excited to meet you, Augie," she said. "I've heard such good things. I want to warn you that, if you choose to speak during our time together, I will know who you are - no matter where we meet again. Also, if you get close enough for me to smell you, I can identify you that way. I already have a sense of you - earthy and hard-working - my mouth is salivating even now. I have been looking forward to our time together since Maggie told me that I would be included. I will guard your secret. If that is too risky for you, I understand. You are under no obligation to share your bed with me; I will honor the secrets the others have shared."

I watched her eyebrows rise as I started shucking my clothing off.

She wasn't ugly - although her eyes kind of freaked me out - and - fuck it - she was on the list.

"I will warn you," she said, laughing, "I will try to get you to talk. I like a challenge. My name is Sue, by the way."

I decided that I was going to make her work to hear my voice. I liked the idea of the challenge as well. I was going to see if I could make this woman scream my name without me saying a word.

I crawled up next to her, cupped her chin, and softly set my lips against hers - turning the peck into a kiss.

She quickly turned the kiss into necking and we were out of the gate.

Her right hand searched out my stiffening rod and she spread her legs to scoot closer to me - straddling me like a stick-pony - kissing me madly the whole time.

When she paused to breathe, she stammered out, "This is a really nice dick. The girls weren't kidding. I have a dildo that's almost this big - but don't tell the others. You'll fit just fine."

She paused - trying to see if I would promise not to break her trust. She smiled wickedly when I stayed quiet.

"I DO love a challenge," she giggled.

She wedged my penis up against her slit and slowly rocked back & forth as our mouths & tongues danced together.

Finally, she put her hand on my chest and said, "I'm ready, sweet boy, please make love to me."

I leaned back, pulling my rod from her gap.

She rolled onto her back and eased her knees apart.

I climbed across her left leg and she gasped as my fuck-meat slapped against her thigh.

"Fuck, yes!" she cooed.

As I nudged the sensitive head - sticky with pre-cum - against the mouth of her vagina - which was just as slick with her own juices, she purred - and opened her arms to me.

I sheathed my flesh-sword in her fiery channel and leaned down to embrace my lover.

She continued purring - nuzzling her forehead against my neck and jaw - as I slowly slid my penis in & out of her grasping muscle-lined tunnel.

"Oh .. I'm cumming sweet boy. Keep it going. Don't stop. I'll love you forever if you can give me two more."

Her pussy got wetter and I sped up a little - to keep the stimulation going.

"Hold that speed, if you can, handsome. I want to drag this out a little. I promise to suck you off if my pussy doesn't do it for you. Give me two more and I'll make it worth your while."

It took several more minutes, but she eventually got those orgasms she'd requested.

When she'd finished the second, she said, "Pussy or mouth?"

I pulled her knees together, pushed them down, onto her chest, and started speeding up my thrusting.

She laughed, "Pussy it is. Fuck me like a whore and see if you can give me number four."

I did - and I did.

I rolled off of her when I had finished blowing my load inside of her; she climbed back on and stuffed her talented twat down onto my rod again.

"Sweet, sweet, boy," she cooed, "I enjoyed that a lot. I know you're going to have a ton of women lined up to spread their legs for you when you're finished with this little quest of yours - but this old hag would love the chance to spend a little time with you - anytime you are in the mood."

Her hand found my lips and she kissed me like we were newlyweds.

I squeezed her tight ass, ran my coarse hands up & down her slender body, and groped her breasts a little, as my mouth battled hers.

"Sweet boy! I don't know how much of that you learned before Maggie got to you - but you're going to be the talk of the town - no matter how well we try to keep you a secret."

"Help me get dressed, handsome. I was in a hurry to get naked and I'm not sure how far away I've thrown my clothes."

Her clothes were in a neat stack by the bed. I wondered why she was lying. Once we were both dressed, she slipped a bill into my pants pocket.

"No," I said.

"Gotcha!" she said, with glee.

I moaned.

She laid her hand on my pocket - preventing me from pulling the money out.

"That's not mine anyway; it's yours. I found it on the floor when I came in here," she said. "I'm just returning it."

She used her hands to find my face once more - leaning up for another kiss.

I wrapped her in a hug and returned the kiss - with all of the heat she'd put into it.

When she'd gotten her fill, I took her by the hand and walked her back out to the front office.

"Sue!" Maggie called, when she saw us, from her seat in the conference room. "How was it?"

"Now, Maggie, you're going to give the boy a big head when we stand here and talk about how we enjoyed that cock of his."

"... and when his head gets big ..." Maggie began.

"... we fuck him again!" Sue finished, laughing.

"Did you get him to talk?" my pimp inquired.

"One word - so far," she said.

Turning back to me, she said, "Good night, my prince."

I stepped in and gave her another kiss.

She looked at Maggie and said, "I tried."

The two of them laughed together as Maggie helped her out the front door.

I motioned that I would lock up when she turned back - and the two of them were on their way.

I stuck my hand in my pocket and pulled out a crisp hundred-dollar bill.

I put my shoes on, grabbed my keys, and headed to the store to buy a small safe.

I figured this wouldn't be the last time someone gave me money that I had "lost" - and I wanted to keep it in a special place.

When I got the safe home, I secured it to the cabinet in the bathroom, to the left of the sink.

I grabbed a Post-It note, wrote "Emily Hall (Sue)" with the date, and stuck my ill-gotten gains inside.

I pulled the $20 bill that Emily Adams had left with Maggie from where I'd stuck it in my wallet, labeled it, and added it as well.

~~~ Week 4 - Lucas Russell (#6) ~~~

Two days later, I was pounding my cock into Angela Russell's ass as she buried her face in my pillow to stifle the stream of cuss words she was screaming.

This was my first time fucking somebody's shit-hole and I had been apprehensive. It had looked and smelled clean, however, so I had given in.

Apparently, Mrs. Russell liked anal a lot - but it was also not a good day for vaginal - and she was adamant that she wanted no latex between my cock and her body - so here we were.

Her first climax had been loud - but the unending stream of profanity - screamed at the top of her lungs - had started when she reached down and fingered her clit & vulva as I continued pounding her ass.

A geyser of ejaculate erupted from her finally, and she collapsed in my hands.

Still holding her up by her hips, I pulled my pulsing member out of her sphincter and rolled her to her side - so I could check her face.

In a minute or so, she regained consciousness.

"That was nice, big boy! Did you cum?"

"No. I was worried about you."

"Such a gentleman!" she gushed.

She rolled back on her stomach and knees - presenting her wonderful ass to me once more.

"I'll leave my clit alone, this time. Fill me up, Buttercup."

I grasped her hips, as before, and started pounding my cock into her ass again - focusing on my own orgasm this time.

In a couple minutes, I was grunting.

"Yes!" she cooed. "Fuck my dirty ass! Fill me up, stud. Flood my body with your seed. You're definitely fucking my pussy the next time we do this!"

I started dumping load after load of cock-snot into her shitter. She had been super-tight when we'd started but now her asshole looked like an exhaust-pipe.

When I pulled out of her, she rolled to her back, and pulled me on top of her - my slick cock sandwiched between us.

She kissed me and complimented me - and told me how much she was looking forward to our next time.

We showered together - cleaning and playing. She stroked my cock until it was hard again - and I rubbed my hands all over her saline-filled breast implants. I usually prefer natural titties - but these were definitely eye-catching - and fun to play with.

~~~ Week 4 - Grace Ramirez (#7) ~~~

Mrs. Maria Ramirez spoke very little English - not that we needed to engage in a lengthy conversation before she sucked on the head of my cock - as I ate her juicy pussy.

I tried not to snicker as I thought about eating my first real Mexican taco.

This woman was all curves. I usually preferred yoga moms - but this woman was the essence of fertility.

Maggie promised me that we were safe and - once we'd warmed each other up - and I squeezed my entire length inside of her clasping cunt - I prayed that I didn't fuck a baby into this woman. If I did, though - assuming that baby was a girl - she was bound to be as beautiful as her mother.

We kissed as I got started fucking her but - soon enough - all manner of Spanish curse words were streaming from her mouth as she mauled every part of both of our bodies that either (or both) of her hands could reach.

Meanwhile, her ankles were locked behind my ass - pulling me in - hampering my movements - but guaranteeing that my cock-head bounced off of her cervix on every thrust.

She squealed and screamed and cussed - and I was in heaven. I have no clue what the woman was yelling but - apparently - my testicles understood every word - because they were working on a hell of a load to pump into this woman.

She only came once - but when she did, she went off like a tornado siren - and my body automatically started blasting seed at her womb.

I was sure I'd just knocked Grace's mom up - and - honestly - I was pretty damned proud of myself.

When I finally pulled out of her, she grabbed my cock and licked & sucked me clean - then she wanted a kiss.

I was a little grossed-out - but - I couldn't tell the sexy MILF "no".

Her kiss didn't taste like my spunk though - it just tasted like she was winding up for Round 2.

She eventually released me and I headed to shower.

She got dressed and then slid the shower-door open long enough to get one last kiss before she headed out front.

Maggie texted me to say that Mrs. Ramirez had a big landscaping job she wanted done and that the two of them would work out the details. Maria had already made an appointment - 28 days ahead - on her next safe day - to come to the office to "finalize" the contract. My phone dinged with the notification that a new item had been added to my calendar.

~~~ Week 5 - Lisa & Logan Carter (#8) ~~~

Lisa & Logan were the only twins in our class. They were inseparable. They were jocks - but only competed in the sports that allowed them to be together - cross country, track, and bass-fishing.

Lisa had tried out for the boys' basketball team but some of the other players had thrown a fit - probably because she did well enough to take their place on the roster - so the Carter twins had bowed out.

I walked to my bedroom to find two women - mirror images of one another - standing - naked - side-by-side.

They were identical in every way.

Not only did they have matching faces and bodies - but every birthmark, mole, blemish, and scar - was exactly the same. It was freaky.

I knew Cindy was the twins' mom. I later learned - from Maggie - that her sister's name was Mindy. I'm still not sure whose pussy I filled - but I fucked (and ate) both of them to orgasm - multiple times - before they were done with me.

I was exhausted - and exhilarated.

When I stepped into the room, the two women wordlessly started undressing me.

I admired the small tuft of blonde pubic hair - shaped somewhat like a heart - that crowned their tight slits.

Every body part, every motion, every word, every giggle - it was like making love to clones.

One rode my face as the other rode my cock.

Without a word, they would switch places and start in again.

I did my best to give the twin on my face as much enjoyment as the one on my cock seemed to be getting.

When I got a chance to look up at their bodies, the two of them were kissing, rubbing, pinching, and groping one another. My cock twitched inside of whichever pussy it was buried in at that moment.

I waited and waited - hoping they would call out the other's name - but it never happened.

Trapped beneath their beautiful bodies, I started writhing when my climax got close.

I think they both knew, but the one on my dick whispered, "He's cumming sister," as I pumped her pussy full of my love-juice.

As soon as the last round fired, she rolled to her back - beside me - and her sister took her place - to see if she could wring any more out of me. If she did, it wasn't much.

"We'll tell Maggie to give you the rest of the night off," they laughed as they eased out of my room - leaving me exhausted and naked - sprawled out on the mattress - still trying to catch my breath.

A couple minutes later, my pimp-lover peeked in and started laughing when she looked at me.

"Poor, poor, Augie," she giggled, coming over to give me a naughty kiss.

She rubbed my wilted cock - but it wasn't coming back to life any time soon.

~~~ Staff Meeting ~~~

The following morning, "Monthly Staff Meeting" appeared on my calendar, set for 5:00pm.

At the end of the day, Mr. Reynolds pulled up to the RR Landscaping office just behind me.

I waited for him at the steps and we both headed inside.

This time, she had the boss lie down first. She climbed on, stuffed his swollen cock into her snatch, and then swatted her ass, telling me to climb on - telling me to give her the Russell treatment.

By the time I dumped my load of semen into her ass, Mr. Reynolds had filled her pussy, and she had drenched the poor man in her seemingly-unending chain of squirting climaxes.

They hopped in the shower while I removed & replaced the bed linens. Mr. Reynolds was toweling off when I got to the bathroom - but Maggie was waiting for a little more one-on-one time before she was ready to call it a night.

We kissed & cuddled, soaped and rinsed, until I was hard again - and I bent her over and gave her two more orgasms before swatting her on the ass and pulling her up for more kisses.

"I wanted you to cum in my pussy, lover," she moaned.

"I'm dried up, sweet lady," I replied. "Your tight ass wrung me out."

She giggled and pulled me in for a few more naked kisses before we climbed out and dried off.

"I've got two more moms for you from my coffee & cards group - and then we'll have to start widening the circle. The girls have already offered to help with the prep-work to get everybody on the list in here."

"At what price?" I asked, laughing.

"Why, sweetheart, out of the goodness of their little ol' hearts, of course!" she giggled, trying to affect a southern accent.

"Right," I said, smirking.

"We've got quite the pyramid scheme going here - lover - and I say we use it to its fullest potential."

"The twins?" I asked.

"They're on-board as well," she said, laughing.

"They?"

"Yes, you little horn-dog - the matched-set. They seem to have had a pretty good time."

"I've never been so tired in my life!" I complained.

She gave me a sympathy kiss, we threw our towels in the hamper, and she went to find her clothes.

The next day, I pulled into the office/house, to find a car that I hadn't been warned about. I headed for the rear entrance, peeled off my clothes, and turned on the TV - flipping to the channel that let me watch the cameras.