Every Schoolboy's Dream Ch. 02

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Sex w/MILF teacher + dating her hot cheerleader daughter.
10.3k words
4.82
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Part 2 of the 10 part series

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

I woke up in a cozy bed - in a room filled with daylight - obviously not my game-cave.

I was not alone.

I opened my eyes to see Mrs. Williams looking at my face, smiling.

"You hungry, handsome?"

"That's not the question I was hoping for," I teased, crooking an eyebrow at her, "but yes."

She started laughing - and threw the covers back to roll out of her fluffy, pillow-top bed.

I watched my sexy lover as she struggled to capture those massive mammaries - and corral them into the sports bra she'd grabbed.

She noticed me noticing.

When she bent over - to pull on the matching panties - she turned away from me, bent forward farther than was required, stepped into the leg-holes - revealing a glorious gap for me to admire - and then, slow as molasses, she slid the tight garment up her long, luxurious legs - shimmying her hips to tug them into place - finally hiding her cute kooch within.

She turned, looked me in the eyes, and bit her lower lip.

Now I knew where Kasey got that shit from.

"When I wake up from this dream, I'm going to be so, fucking, disappointed," I said. "I hope, at least, that I'm covered head-to-toe in jizz."

My former Science teacher - the Goddess of Belmont High School - started snort-laughing.

I was trying to focus on her bouncing breasts but the snorting got me - and I started laughing as well.

She put on a fluffy robe, walked around to "my side" of the bed, and threw the covers off of me - looking down at my naked body - and morning wood - that had just been bolstered by her little show.

She held out her hand, "Come, dear boy."

I took it, replying, "Yes, Beloved."

Downstairs, Kasey was sitting at the dining room table with her tablet and an empty cereal bowl.

Mrs. Williams brought the jug of milk and a couple boxes of cereal from the kitchen.

I went in search of the bowls & spoons - with a little guidance from Kasey.

As we finished our brief meal, I looked across the table, at my curvaceous lover, and raised a lusty eyebrow - checking to see if she was ready for Round 3.

"I think I need to stop before I overdo it any more - my pussy's a little sore - thanks to you."

Kasey looked up from her device, "Serves you right, acting the slut all night long!"

Her mom looked over at her - and then her mind, obviously, went sideways.

"Sorry, mom," Kasey apologized, watching her face. "I sound like grandma."

"First of all, no, you don't. Second of all, you're not wrong - and I enjoyed every minute of it," she said, briefly looking over at me to deliver that message. "I got a little carried away - trying to catch up. You just caught me off-guard and I wonder what your father would say."

"Daddy would say that you've been punished enough. 'Where's my goddess? I must supplicate.'"

Mrs. Williams started laughing, "You almost sounded like him." Her face grew a little sad. "God, I miss him!"

"Did you feel worshipped - last night," Kasey inquired, "with your twat full of Reggie's 'offering'?"

"I did," her mother admitted, replaying something in her head and smiling.

"I guarantee you - if daddy was watching from Heaven last night - he was happy for you."

"Thank you, baby. Have I told you that you're my favorite daughter?"

"Once or twice - but I won't stop you, if you want to tell me again."

Mrs. Williams got up, walked around the table, and wrapped Kasey in a hug.

"I'm not pushing you to escalate your time-table - or shortcut your analysis - but I'm seriously going to do my best to fuck your boyfriend to death before you decide you're ready for that cock of his.

"TMI, mom."

"Your father was definitely more experienced but.."

"Mother.." she growled.

Laughing, her mother said, "You know you're beautiful when your freckles all turn pink, right?"

Shaking her head in frustration, Kasey said, "If you're finished embarrassing me, I think I'll walk my boyfriend to his car."

Mrs. Williams stepped over to me, pulled my face up for a soft, sensuous kiss, and then wrapped me in a hug - squeezing my body in between my favorite twins.

She pulled back to look in my eyes, and said, "Thank you - for everything - agreeing to this crazy idea, the sex, the laughs, the sex,.."

"Mother.." Kasey warned.

The hot cheerleader - in a rose-colored, silk pajama shirt & shorts set that hid way too much - stood and extended her hand for me to take. I joined her and took the proffered hand - interlacing my fingers into hers.

On the way outside, she suggested we chat in the car - so I let her in the passenger side and went around, climbing in to join her.

"Are you busy Friday night?" I asked mischievously.

She nibbled that lower lip again - so - of course - I kissed it.

"If you're like the other guys I dated," she began, "you will quickly become tired of my frigidity."

"Frigid? Because you're not ready to fuck? You've already got me, sitting here, salivating, waiting for your little lip-nibble Pavlov's Bell.. just so I have an excuse to kiss you."

Her soft giggle was intoxicating.

".. and I hate to mention my other lovers - but I'm pretty sure any blue-balls you manage to give me - will be graciously evacuated by your nymphomaniac mother."

She laughed this time.

"She might actually only fuck you twice next week - I was really surprised when she didn't want to go another round this morning. She and daddy weren't very quiet with their love-making and the sound carries in that house late at night."

I nodded.

"Would you think I was weird if I admitted to rubbing myself, listening to them?"

"Well, I kind of wondered how you were.. um.. taking care of business. That makes more sense, kind of."

"You don't think it's weird?"

"Most guys I know are turned on by every one of their five senses - and jerk off more than once a day. I don't know that many girls but you don't seem abnormal to me."

"I really like you. I hope this works out."

"I've already told you I think every part of you is hot - including your oversized cranium - but I can repeat it if you need to hear it again."

She nibbled that lip once more.

"Seriously? You keep this shit up and you'll be riding my cock within days," I teased, as I sat back up from delivering her requested kiss.

"I will, huh?"

"Yup."

"Pretty cocky."

"Very cocky. Very cocky up your koochie."

She laughed, "You're horrible."

"You're beautiful. Can I kiss you?"

She nibbled the lip again.

I turned sideways in my seat, took her face in my palms, and looked into those crystal-blue eyes.

"You give my brain a hard-on."

She started laughing, "That's the dumbest.."

I silenced her with a kiss.

I simply pressed my lips to hers and waited for her to quit trying to talk past the contact.

When she relaxed, I kissed her - trying to pour all of my feelings into it. No tongue. No games. No dramatics. Just 'I love you' as a kiss.

I finally ended it - but still held her face - watching to see if she approved.

"That was nice," she admitted. "I guarantee it'll be at least a month before you see my pussy - and you're still a dork - but that was nice."

"I'm a very patient man. Methodical even."

"Man?"

"I'll let you decide, when you're ready."

She giggled.

I released her face.

"You definitely like to play with my head, don't you?" she grinned.

I opened my mouth to spin her words back as a double-entendre..

"Don't even!" she laughed, throwing the palm of her hand onto my face & mouth to stop what she knew was coming.

I just laughed into her hand.

When she dropped it - but took my hand in hers - I asked, "So, can I see you Friday night?"

"Is four too early?" she asked, grinning.

"I'll make it work," I replied.

"Okay. Pick me up at four. Take me to do something fun - then we'll go to dinner - then we'll come home and 'Netflix & chill'," she said, smirking.

"Food?"

"Surprise me."

"No help. Fine. You want a surprise.."

"Nothing living!" she countered.

"Damn! Foiled again!" I said, dramatically.

She didn't take the bait but smirked.

"If you leave the parameters wide-open, it's hard to say what you might get.." I offered.

"I'll chance it," she said, grinning.

I held my thumb & forefinger to my chin, and crinkled an eyebrow, as if I were plotting.

She ignored my play-acting.

"Something fun? Any specifics or constraints for that part of the evening?" I asked.

"Not really?"

"Putt-putt?"

"Less competitive - more mentally stimulating.."

"Hmm, okay. I'll have to work on that. Do I get bonus points for creativity?"

She laughed - but gave me a quick peck on the lips - before releasing my hand, scooting to the door.

"See you Friday at four," she said, climbing out.

As she headed into the garage, she turned to look at me. I blew her a kiss.

She returned one of her own.

I pinched my arm - just to check - and then started the car, backed out, waved at the neighbor working on her flowers, and headed home.

~~~ The Inquisition ~~~

Sunday night, I got a text from a former classmate, "You seeing anyone?"

I responded with, "Yes."

"Who?"

I texted Kasey.

She informed me that she'd already gotten tagged by a different classmate - who had asked her if she was going to be busy Friday night.

Based on who the two people were, she quickly figured out that it was Grandma Williams, and her card-playing cronies, collaborating to nose around for information.

We each blocked the people who had texted us.

Wednesday night, I got to work and my boss laughed when he saw me.

"You're going to have a special delivery tonight."

"Why's that?" I asked.

"Some old lady called for you on Monday night."

"We're not open on Mondays," I laughed.

"She didn't realize she was on voicemail and was trying to get us to send you to her house with a pizza."

"What address?" I asked.

Mack grabbed a piece of paper and rattled it off.

"She called back, again, last night and I told her you didn't come in until tonight. Who is it?"

I'd just finished Googling the address.

"My girlfriend's grandmother."

"Dude! You're fucked. Anybody trying that hard to track your ass down.."

"Do I make the delivery - or go home sick?"

He thought for a minute.

I realized calling off would just be a stall-tactic and wouldn't work.

"You still have those smart-glasses - those GoPro goggle things you were trying out?"

"Yeah. At home."

"Run and grab 'em. I'll ride shotgun when you take the pizza. Hit record when you get out of the car and chat the old bag up and see what she spills. Give me a hand-signal if I need to rescue you."

I looked at his face and he was dead-serious - so I headed back out to my car, ran home, grabbed the glasses from my shelf, and cruised back to Pop's - still on time for my shift.

Two hours later, I was hurrying back from a delivery run when he met me at the door, grinning, with a pizza in his hands, "It's time."

My hands were sweating, as I drove to the address. I wiped them on my pants.

"Dude. How bad is this bitch?"

"Kasey says she's Hitler."

"Just play it cool. I want to see this video."

We pulled in front of the house. I hopped out, walked around the car - hitting record on the glasses - and took the pizza from Mack.

I knocked on the door. I could hear footsteps - not shuffling - so she wasn't that old.

The door opened.

"Pop's Pizza delivery," I said, falling into my usual speech.

"Are you Reginald Mitchell?"

I gave her a dramatic pause.

"Yes?"

"Are you dating my granddaughter, Kasey Williams?"

"I don't kiss & tell, ma'am," I said, giving away nothing.

"Yes or no?"

"If you want to know who your granddaughter is dating, you might want to pick somebody closer to the source, ma'am."

"I didn't ask for smart-mouth."

"I'm delivering a pizza, ma'am. That'll be $22.50, please."

"I don't want the pizza. It's not what I ordered. I'm cancelling the order."

I turned back to the car.

"Call the cops. We got a stiffy."

Mack stuck his thumb in the air and got on his phone.

"What?! What are you doing?"

"Standard procedure, ma'am. Happens a lot. The cops even gave us a special number to call. That's my boss in the car. His name is Mack. He's the one you talked to three different times to see when I was working - so you could bring me over here to interrogate me - and now you've got the balls to try to skip out on paying for the pizza. You may want to go ahead and find your driver's license. The cops normally ask for that while we go through the whole routine. It usually takes a couple hours - but I find it somewhat fulfilling. It pisses Mack off, though, so I hope you never want to order from us again - which kind of sucks - cuz we have the best pizza in town."

"You don't need to involve the police. I'll get my wallet. I was just messing with you."

"Right.. You may want to do that - cuz like you ordered a pizza - but you aren't holding any money - which kind of tells me you were planning this the whole time."

"Wait right here!"

She moved pretty quickly for a heartless hag.

I didn't bother to signal Mack. He hadn't called anybody. Although - I knew without looking that he still had the phone to his ear - and was nodding - and moving his lips.

"How much was it?" she asked, digging through her bills.

"$22.50"

She handed me a twenty and a five. I stared at her.

I knew - for certain - that the words, "Keep the change," had never come out of this bitch's mouth.

"We don't carry change. They tell you that when you order."

She held out her hand. I returned the bills.

It took her another five minutes of digging - but she came up with the exact amount.

While she was fucking around, I did think about asking for a tip - just to poke the bear.

I handed over the pie and turned to leave.

"I'll give you a hundred dollars to break up with my granddaughter," she offered.

I turned back to face her.

"First of all, you're a bitch for even suggesting that I could be bought off. Secondly, you're a cheap bitch for thinking $100 is worth more than your granddaughter. And, lastly, your granddaughter is hotter than 99% of the women on the entire planet, smarter than most - male or female, and one of the nicest people I've ever met. But - I get the feeling you're not trying to save her from horny young men - you're just a stingy controlling hag who probably abuses their husband mentally and emotionally - if not physically - on a regular basis. You really need to find professional help."

"Well! I never.."

"Obviously, you did at least once - cuz that's how Kasey's dad was born - am I right? Was he like a horrible person or something? Is that why you hate everybody? Kasey says he was awesome, though, so maybe his entire DNA came from her grandpa."

She goldfished.

She was standing in the doorway, holding the pizza box, with her mouth opening & closing - like an oxygen-starved guppy - gasping for breath.

I made sure I was facing her straight-on - so the glasses were getting her reaction full-frame.

The devil whispered in my ear - and I grinned - yelling loudly through the open doorway, "Mr. Williams! If you need help, just call Pop's Pizza - and order the Triple Olive Special. We'll send the police."

I turned and headed for the car.

Once I was belted in, I hit the button on the glasses to send the video to my phone, and dropped the car into gear.

Grandma Williams was still standing there, with the door hanging open.

I was pretty sure that - if the bitch had had pyrokinesis - my car would have exploded.

Mack was holding my phone.

"I had a pretty good angle - and don't really need to see the video - but your girlfriend is going to shit herself. What a bitch! I'll bet the old bag re-gifts her used underwear for Christmas presents."

That was a pretty good one - even for Mack. I was laughing so hard I had tears in my eyes. I could still barely see by the time we got back to the shop.

For the next half-hour, work came to a stand-still, at Pop's, as Mack Chromecast'd my phone to the lobby TV and all of the employees stood there to watch the replay.

I'd already had my fill of Mrs. Williams, so I took over babysitting the pies that were in the oven - and covering the phone.

The guys pretty much all high-fived me.

The girls were quieter - some of them knew Kasey - the others were just thinking about how big of a bitch this woman was.

I got a couple pats on the shoulder from one or two of them.

I asked the "mom" of the bunch if I should show the video to Kase.

"She, obviously, already knows what her grandmother is like - and I think she'll want to see it - but there's like nothing of redeeming value there," she lamented. "Sad."

I nodded.

She looked in my eyes.

"I'd almost feel sorry for her," she said, "but she's soo obviously mental. I'm really actually worried we might get an order for the Triple Olive Special."

I started to smile but realized she was serious.

I texted Kasey and told her that I had a video of a face-to-face confrontation with her grandmother. I asked her if she wanted me to save it until Friday - or get it over with now so - that it wouldn't spoil our time together.

Ten minutes later, she walked into Pop's.

We didn't even get to talk until fifteen minutes after that. Absolutely every employee in the place queued up to give her a hug and offer their condolences.

She was pretty floored by the outpouring of emotions.

Mack shuffled my deliveries to others and - by the time Kasey was free - I was off the clock.

We went out to my car.

"How bad is it?" she laughed. "Half of those people don't even know me."

I opened the door and she slid in. I nudged her to scoot over and I dropped in beside her, handing her the phone.

"Just to be clear, I didn't show it to them. Mack grabbed my phone. However, I didn't stop him."

She started the video, quiet through the whole thing.

When it ended, she hit the power-button to put it to sleep - and handed my phone back - turning to face me.

She grabbed the bottom of my chin between her thumb & forefinger and pulled my face towards her - delivering a soft kiss directly to my anxious lips.

"You really are trying to get into my pants, aren't you Mr. Mitchell?"

"I would love nothing better," I admitted.

"It wasn't perfect - and you may have just launched the Crusades - but you did good."

"We need to find a way to cut these puppet-strings of hers," I said.

"I've thought about it. I admit I got a little distracted with my Sister Wives scheme - but I've already spent several nights trying to work out a solution. Part of the problem is, I don't even know where all of the tendrils reach."

I looked into those sad, captivating eyes.

"Could I get one more of those kisses? Your grandmother stiffed me on the tip and.."

"You're horrible!" she accused, laughing.

She clenched her fists and pounded my chest.

"Hello? Pop's Pizza?", I laughed, "I'd like to order the Triple Olive Special."

"Oh..!" she growled, grabbing my head in her hands, pulling me into a fierce kiss.

I melted in the heat of the passion she was pouring into me.

The kiss got longer and longer - and turned a little feral. It reminded me a lot of the one her mother had given me, while I was tilling her garden - to get ready to deliver some seed.

When she released me, we were both gasping for air.

"Damn, girl! I can't wait until Friday!"

She reached down and grabbed my stiff cock through my jeans. I was turned on and scared - all at the same time.

"I promised you that you wouldn't get to see my pussy for a month - and - dammit! I keep my promises. Unfortunately, that means I will have to leave this car without giving you my virginity. I hope you have something special planned for Friday - because you'll have a tough time topping this."