Every Schoolboy's Dream Ch. 05

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Sex w/MILF teacher + bachelor party + wedding rehearsal.
12.9k words
4.79
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Part 5 of the 10 part series

Updated 10/09/2023
Created 05/05/2023
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~~~

From this point forward, Reggie repeatedly refers to Mrs. Williams as his mother-in-law during sex - so I'm switching the category from Mature to Incest/Taboo - since that's not socially acceptable in real life.

~~~

~~~ Saturday ~~~

In the morning, Kasey and I straightened up the front room while the moms started on breakfast - real breakfast - not just bowls of cold cereal.

The doorbell rang and Kasey went to see who was there. I heard her gasp in alarm and ran across the front room towards the foyer - to meet Grandma Williams hurrying in - having shoved her way past her granddaughter.

"What the fuck, Grandma?" Kasey yelled, catching up to her.

I stood in her path, "What do you want?"

"Who's that hussy?" she asked, looking past me, over my shoulder.

I didn't really need to turn to look - since there was only one person in the house that she didn't know - but I did anyway. Of course she was looking at my mother - whose eyes were open wide.

"Not that it's any of your fucking business - but that happens to be my mother."

She didn't even have the decency to look chagrined at calling my mother a whore. She was peering around the front room - apparently looking for evidence of some misdeed.

"You are trespassing," I informed her. "Leave now or I will call the police."

"You wouldn't dare. I own this house."

I ignored her phishing attempt. I hadn't seen the papers but I was pretty sure the deed was in Mr. & Mrs. Williams' names - regardless of how much Kasey's grandmother had donated to the cause.

"You remember your police officer friend from the other day? I just happen to have his business card in my pocket. He specifically told me that - if I had ANY concerns - I should call him. Did you know that he confirmed that it was your number that called in that tip? He added that information to the police report that he filed."

Looking around the room and - obviously - not finding the den of iniquity that she'd expected - she stepped back.

"Fine. I'm leaving."

As she turned to go, I cleared my throat and said, "Just so you know, there will be an order of protection on this house by the end of the day. If you need to talk with Kasey or her mom in person, you can call and make an appointment to meet them at a public place."

She harrumphed but, otherwise, didn't respond. She did, however, slam the door on her way out.

I followed her - to make sure she'd actually left - and wasn't hiding somewhere in the house.

I waited until her Lincoln backed out - and then pulled away. There was a new tire on the driver-side rear.

I returned to the kitchen - where all three of the women in my life were staring at me.

I looked at mom and said, "Welcome to the Grandma Hates Me Club."

"No wonder Grandma Mitchell said bad things about her."

"What did your grandma say, Reggie?" Mrs. Williams asked me.

Kasey looked at her mom and said, "Nothing nice - and Grandma Mitchell is a lovely person - so that should be enough said. I would assume her memories of her former classmate were unembellished. The simplest response to your question would be that the woman has been this way all of her life."

Mrs. Williams nodded.

Mom stepped over and wrapped an arm around her, "I'm so sorry."

Kasey's mom sniffled, "I loved her son - and he loved me. He gave me Kasey. It was worth it."

Kasey joined the hug.

Meanwhile, I texted the police officer - making good on my threat to have an OP on the place by the end of the day.

When the sniffles had diminished, I said, "Kase?"

"Yeah?"

"Guess who had a new tire on their car?"

She started laughing so hard that she was holding her sides.

As we finished making - and then devouring - our breakfast, Kasey and I relayed the rest of the story about Grandma Williams' new tire.

When we had finished the tale about our protest against the neighborhood peeping Tom, my mother-in-law got out of her chair, walked over to me, and kissed me on the mouth, saying, "Thank you, Reggie."

My mom raised her eyebrows but said nothing.

I went to help Kasey's mom with the dirty dishes and she bent over the open dishwasher and turned to give me a wicked look.

I started belly-laughing.

Mom, of course, asked what was going on.

I told her that - the last time Mrs. Williams & I had been loading the dishwasher - there had been a mishap and Kasey's mom had ended up soaked.

"Yeah, that thing's a little sensitive," Kasey added, "you've gotta be careful about which buttons you're pushing."

Mom just smiled as the three of us giggled.

When mom & I had collected our things, Kasey & I gave Mrs. Williams hugs & kisses. I didn't make the kiss too long - but mom didn't even react this time - even though I know she noticed that I kissed Kasey's mom on the mouth again. Mom stepped up and gave her a hug as well. She suggested that Mrs. Williams keep the house locked up while the two of us were meeting with Pastor John.

As we headed to the door, I reminded her that the wedding party was going to the waterpark for the afternoon - and that we wouldn't be back until around dinner time.

She responded that she'd have something hot for me to eat when I returned.

I started to reply but Kasey swatted me on the ass and shoved me out the front door.

My mom just looked back and forth between the three of us.

Mom drove us home.

I ran in to grab my cinch-sack for the waterpark - and my car keys. I gave her a hug - and a kiss on the cheek - on the way out the door.

Pastor John asked us how we were doing, what problems had come up, and how we'd resolved them. We mentioned that Kasey's grandma was being a pest but that, otherwise, we thought we had most everything handled.

He offered a few more topics about maintaining a happy relationship and then prayed with us. As we left, he told us to call if we had any questions but that - otherwise - he would see us Friday at the rehearsal.

We told him that he was welcome to join us for dinner at Benny's after practice and he said he might come - commenting that he really enjoyed their burgers & fries.

Kasey and I hit the taco truck for lunch and then headed to the waterpark.

When she came out of the locker room, she had on a black one-piece that had hot pink trim & spaghetti straps. She looked amazing. I felt my cock rising to greet her and I did nothing about it. Fuck - she was hot!

She smiled, shyly, at me and I noticed that her nipples were hard. I wanted to touch her so badly - but I'd already agree to be good.

Nick showed up next. He paused, briefly, looking at my fiancé and then told her she looked gorgeous. He was being completely genuine and Kasey took the compliment with a smile. We walked over and sat on the edge of the shallow pool - waiting for the others to arrive.

Cindy was, obviously, worried about her curves - and tried to hide it with a swim-dress. It was cute but she would have done her body more justice to go bold. Curves aren't my thing - but - it was pretty obvious that Paul liked what he saw. The lifeguard yelled at him to go easy with his hands.

Natalie came out in a one-piece like Kasey's - but Nat's had a printed design down the front - where Kase's was plain.

The eye-catching part of Natalie's suit, however, was the zipper - outlined in white - that ran from her neck to her navel. It was zipped all the way up - but the allure was that she could make it as sexy as she wanted - whenever she wanted.

A stream of curse words came out of Nick's mouth that would have had Pastor John worried.

I suggested we go hit the waterslides and Nick complained that he wasn't going to be able to stand up for a little while. Natalie glided over and offered him her hand - but he still wouldn't get up.

She leaned over, kissed him on the cheek, and whispered in his ear. The next thing I knew, he was leading the way to the waterslides.

When Kasey asked her what she had said to him to get him to move, she replied that she told him, "The longer it takes you to move, the lower I unzip my zipper."

Kasey laughed but then leaned closer and whispered, "Looks like Nick's packin', Cuz..." I only heard what she said because she was holding my hand as we walked through the crowds. Natalie punched her in the arm and giggled.

It's probably not very nice to admit, but, I'm proud to say my girl was getting more looks than anybody else in the place. "If they only knew ...," I thought. "Her mother is just as hot."

Kasey's cousin, Natalie, was no slouch either - and so gentle with my friend. I was ecstatic with how things seemed to be turning out for Nick.

Three hours later, we had done just about everything there was to do - and were relaxing on the lazy river - when Paul got caught trying to slide his dick into Cindy on the two-person inner-tube - and we were asked to leave.

Cindy was fairly unapologetic. She told the lifeguard this was the first time she'd had a boyfriend who was brazen enough to try to fuck her in public and she was pretty damned happy about it. The lifeguard apologized but stated that she was just following the rules. She suggested that Cindy take him to Coney Island or the zoo.

Outside, at the park entrance, Kasey talked a passerby into taking a few pictures of the wedding party. I realized, at that moment, that we didn't have anybody lined up to take photos of the ceremony. After we said our good-byes, as Kasey and I walked to the car, holding hands, I asked her about it. She said Natalie's little sister was pretty good with a camera and she'd give her a buzz.

When she turned to answer me, she caught me leaning backwards to watch her ass as we approached the car. She released my hand and reached down to stroke my hard-on through my swimsuit. I moaned.

She sprinted ahead, laid her towel on the hot hood of the car, and hopped up to sit on the edge - opening her arms for me to cuddle.

I advised her that this was not a good idea - my cock hardening even more at the sensual buffet before my eyes. She stayed put, inviting me in.

I think she expected a kiss - but I dove into her arms and started nibbling the rigid bumps on the front of her suit. Her fingers twined into my hair as she gasped and then started giggling.

I hugged her tight body and chewed and sucked her breasts through the cloth. I leaned back and then looked down - spying one more bump that needed attention.

As I leaned into her arms - pressing my lips (finally) to hers, I teased my middle finger up the little camel-toe in her suit and lightly stroked that other bump.

Kasey hissed, "Fuck, Reggie!"

I wrapped my arms around her, pulled her from the car-hood and held her to myself. Her legs went around my waist - ankles locking behind my ass. My hard-on was very close to its happy place. I kissed her hard - and she returned every bit of it.

"Damn, Kase! I don't know if I can wait a week!"

She giggled, "Play nice, or you're going into time-out, mister."

"Fuck, Kasey! I'm starving here and you're a damned buffet!"

She hung from my body - her arms and legs locked around me. My cock was trapped - pressed up against her kooch. The urge to rip her thin swimsuit off of her and pound my cock into her virgin pussy was threatening to usurp control.

She giggled and kissed me - her fingers working through my hair - turning me on more - making my stiffy worse.

"Kasey ..." I growled.

"Poor, poor, Reggie ..." she teased, nibbling the edge of my jaw.

"Unless you want to lose your virginity in the parking lot of Wacky Waves, we need to stop."

She giggled, but - after claiming one more kiss - released her hold on me - and slid down to stand on her own.

I picked up her towel, folded it twice, handed it to her, and opened her door. Once she was in, I went around to my side.

I slid behind the wheel - into an arm around my shoulder, a kiss on my cheek, and a little thigh-stroking that was turning into a hand-job.

"Girl - you are playing with fire," I warned.

She giggled, released me, and slid clear over to lean against her door.

I'd been in trouble - but now I was missing her touch. As I made my way through to the exit, I looked over to see that her suit was half-way off. She was tweaking a nipple with her left hand as her right was rubbing up and down the crotch of her suit.

"Fuck! Kasey! You're gonna kill us!" I complained.

"Eyes on the road, big boy," she laughed.

I pulled over to the shoulder, put the car in park and turned to face her.

"You cannot expect me not to watch you, vixen. Fuck! You're lucky I haven't already jammed my cock into that pussy of yours."

She must've finally seen the flames in my eyes. She laid the towel on her lap, rubbed her forefingers around her nipples one last time, and then pulled the suit back up. Her one act of rebellion was to leave the hot-pink spaghetti straps dangling under her armpits.

"I'm horny, Reg," she moaned.

"I can definitely appreciate that, Kase, but you cannot expect me to control myself while I watch you do that. I either need to be able to take care of myself while you are - or I need to help you."

"You could jack off while you drive us home," she offered, a wicked look on her face.

"I'd be watching you rub yourself off and wreck us, baby."

"Fine. Drive us home. I'm sure mom can keep you busy while I get myself off."

Looking at my crotch, she said, "Did your dick just get bigger?"

"Probably," I admitted. "You and your mother do bad things to me."

Kasey giggled, "... and you love it."

I nodded, dropped the car into drive, and headed for Mulberry Street - trying not to think about how I could physically get my dick into my wife and my mother-in-law at the same time. I failed.

"Kase?" I asked, as I spotted the Pedo-Van, parked directly across the street from #24.

"Don't know. We'll ask mom if she's talked to Mrs. Jordan."

We both looked at the vehicle as I pulled in. Kasey waited on the sidewalk; I headed over to see if anybody was in it.

I couldn't find any people in or around it. There were a couple small holes on each side - much like the camera lens on my Google Glass knock-offs. There was a dash-cam above the rear-view mirror - but I couldn't tell if it was on or not. I didn't see anything in the back - but assumed there was another one there.

I was guessing that Grandma Williams had finally hired that private investigator - or was just making her actions more overt - while carefully skirting my rules of engagement.

Mrs. Williams was standing there, buck-assed naked, when we closed the door.

"Kasey," she started to ask.

"Hold a sec, mom. Have you asked Mrs. Jordan about the van?"

"What van?"

"There's a surveillance van, sitting in front of her house. Probably Grandma's PI," she said.

"I'll call her after Reggie fucks me. I promise!"

Kasey turned to me, "Couch. Naked. Sitting."

I moved to obey - struggling to get my pants off with my cock & balls inflating at the thought of fucking the hot MILF who was standing there, watching me undress, and salivating.

Kasey started to tell her mother to go get her phone but realized the cougar had already targeted its prey and was moving to attack.

I was barely seated before the sexy Science teacher had straddled me - stuffing her breasts into my mouth at the same time she was stuffing my cock into her quim.

She seemed to be managing the pace of things downstairs - so I contented myself with nursing on her fabulous fun-bags.

"It's ringing," Kasey said, as she handed her mother the phone.

"What? No!" she said, as her hand reflexively wrapped around the device.

Staring daggers at her daughter, she put the phone to her ear.

I continued feasting on her breasts as I used my hips to thrust my anxious cock in & out of her vagina as she talked to the neighbor.

"Mrs. Jordan? Kelsey Williams. <pause> Yes, yes. A week from today. Yes. They're just inviting family. <pause> He's very nice. You've probably seen him. <pause> Yes. They've known each other forever and just started dating a few weeks ago. <pause> That's sweet of you to say! Yes. Kasey, obviously, is head-over-heels ..."

She looked into my eyes and I darted forward to give her a peck on the lips.

"He's a sweetie! Yeah. He's actually helping me with something right now."

Peeling the top of her swimsuit down and dropping onto the couch next to us, my beautiful bride-to-be giggled, "Yeah. Clearing out more cobwebs..."

Kasey massaged her tight breasts and squeezed her nipples between her thumbs and forefingers. My cock got bigger, watching her titillate herself.

Kasey reached over and pinched her mother's nipples until she had her attention. "Van," she said.

"Hey, Deloris? Does that van in front of your house belong to a guest? <pause> No. It's not ours either. <pause> I'm not sure how long ... <pause> Sure. <pause> Yeah. The kids noticed it when they got back from the waterpark. <pause> Yeah. I think I would call them too."

Her first orgasm took her. She reached to put her hand on my shoulder - to steady herself - and missed - shoving my head back as she palmed my face - and held on.

"Oh! <pause> Fuck! <pause> Sorry, Deloris! <pause> Got a little light-headed there. <pause> Yeah. Stood up too fast. <pause> Yeah. <pause> I'm gonna lie on the couch a sec. I'll talk to you later. <pause> Yeah. Let me know what you find out. <pause> Thanks. You too. Bye."

She threw the phone towards the arm of the couch and it slid into the corner. Her hand on my face wrapped around my jaw - and the other one clamped onto the other side. She kissed me hard and started fucking herself on my pulsing pole, growling.

My mouth and cock were busy - but my hands were free. I ravaged her breasts for a couple minutes - until I felt her next orgasm coming - whereupon I grabbed her ass and started forcefully pounding her tight body down onto my lap - stuffing her slippery pussy with my aching member - over & over again.

"Fuck! Kasey! Go find your own husband. I'm keeping this one."

I glanced over at my fiancé - a little worried about her response - but she just laughed. "He's my husband, bitch - but if you're a good mommy, I'll share him."

"Fuckkkk, Kasey! I'm cumming again!" she cried out.

I had to release her ass and grab her ribs. She was getting a little loose in the saddle and I was worried she was going to topple.

"Don't cum yet," Kasey ordered me - just as I was getting ready to flip her mother around and fuck her senseless. "Finger me."

She grabbed my right arm, slid her ass in next to her mother's leg, and leaned back into me, shoving my hand down the front of her swimsuit - which was bunched up around her waist.

"Oh! Yes!" her mother cooed - as my cock lurched inside of her - as my palm slid across my fiancé's mons - and onto her silky-smooth labia. I could feel her thin landing strip tickle my wrist.

"Kasey ..." I warned.

"Mom, ride Reggie's cock while he fingers my cunt. I'm so horny!"

Mrs. Williams took her daughter's jaw in her left hand, leaned forward, and gave her a tender kiss on the cheek.

My face was up against Kasey's neck. My left hand was holding her body to mine. My right was exploring her forbidden realms. My nose was buried in her hair - just behind her right ear - filled with the scent of her shampoo, a little chlorine, and a little sweat.

"Kasey ..." I moaned, as I rubbed my palm and fingers across her smoothly-shaven entrance.

"I'm already wet," she said. "Just slide a finger in. No peeking! You still can't see it - but I need a little of you inside of me. You've got me all worked up and I don't want to take care of it myself this time."

"Oh, baby ..." I moaned. "This is a bad idea!"