Every Schoolboy's Dream Ch. 02

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"Will do."

I turned to Kasey.

"Is there like a smaller version I can order, next time, so I don't feel like I'm throwing away half of your work?" she asked him.

"I gotcha, Kase," our classmate promised.

"Thanks, Cindy. We'll be back - maybe not next week - but soon."

"See you guys," she said - as we headed to the door.

"Hey, Reg," she called to me, as second later.

"Yeah?"

"You need any napkins for the car?" she said, laughing.

"Very funny," I groaned, opening the door for my overstuffed girlfriend - who was laughing just as loudly.

In the car, Kasey turned to me, "What about Cindy and Nick?"

"What happened to your cousin?"

"Plan B. I really liked Nick. I want to get him a girlfriend."

"Maybe. I don't know what Cindy's really looking for. She's so casual about everything. Nick's really serious. I don't know - it might work."

"What if we bring him here?"

"We could. Cindy's biggest problem is that her dad doesn't have anybody else to work the counter - she's almost already married - to her job."

"That's kind of sad."

"Yeah. I mean - she doesn't complain - but I've never seen her go out just to have fun."

"I'll have to think about it," she mused.

"Tell you what, I'll call Nick and we'll bring him here in two weeks. We'll see if anything sparks - but no meddling - clean room."

"Fine," she conceded, a little grumpily.

As we rode along, she took my right hand and laced her fingers through mine.

"You're right," she admitted. "Nick needs the real deal - not something I've manipulated."

"I know you're just trying to help," I told her, encouragingly.

"You're smarter than you look," she said, laughing.

I tried to look like I'd been mortally wounded.

~~~ The Inspection ~~~

The door had barely closed before Kasey's mom had my pants around my ankles and was fondling my cock & balls like a TSA agent.

"Mom! Behave!" Kasey barked. "You just had that thing down your throat like two hours ago. Nothing happened - and he's still mine for another hour."

".. but, Baby.." she complained.

Kasey handed her the to-go containers.

"Try these. If you're a good girl, maybe we'll take you with us next time."

I pulled my pants up as Mrs. Williams headed to the kitchen with the leftovers.

I dropped my sandwich & drink on the table - and plopped onto the couch. Kasey snuggled in beside me.

"Sit on my lap?" I asked her.

"Why?"

"So I can see your eyes."

"You just want to rub your boner against my ass," she accused.

"Just a bonus.." I said slyly.

She stood and started to sit across my legs.

"Face me?" I begged.

"You're just trying to get me to dry hump you!"

"I promise I will not move - unless you tell me to."

From the kitchen, between bites, her mother said, "Grinding your clit against his boner is not sex - and it will seriously improve your disposition."

"Not helping," Kasey growled, over her shoulder.

She did, however, straddle my lap - with her feet by knees and her knees beside my hips on the couch.

I tucked my hand under her arms and I wrapped my arms around her.

"You said you wouldn't move," she growled.

The arm-chair quarterback, in the next room, yelled, "False start! Five yard penalty! Repeat the first down."

Kasey's frustration with her mother was the only thing that exonerated me for failing to follow directions - although - in my defense - I thought it had been obvious that I was talking about movement below the waist..

She wrapped her arms around my shoulders.

"How did I do tonight?" I asked.

"Are you this insecure? This is like the tenth time you've asked."

"I want to please you," I said, "I seriously like you - I'm not just trying to make your spreadsheet come true."

"What a dolt! I obviously missed a calculation somewhere," she said, chortling at me.

She released the hug, pulled my face in for a quick teaser-kiss, and said, "You did well. Maybe even good enough for a reward."

At that point, she made a little circle with her hips - and my boner ground around on the fly of her blue jeans.

"Fuck! Kasey!" I moaned.

"Illegal Motion! Five yards," Mrs. Williams yelled, between bites.

Kasey grabbed my shoulders and started grinding her mons around on my stiffy.

She closed her eyes. She seemed to be fixing a finish line in her mind.

"Can I hold your hips?"

"No."

"Touch your breasts?"

"No."

"Your face?"

"No."

"Can we do this with just our underwear on?"

"Definitely not."

I leaned back against the back of the couch and let her frig herself on my dick-bump.

It was stimulating me a little - but it wasn't going to get me off unless I could participate more fully.

When her moaning intensified, I looked up at her face - determined - focused - climbing her own personal mountain.

"Tease my nipples - but nothing else - through the shirt," she commanded.

Those tight little 22-calibre points where rubbing against the inside of her top.

I reached thumb & forefinger of each hand up and nipped at the tiny buds. When I finally caught one, she hissed at me.

"Enough!"

I went back to being a human sex-doll.

She was still, obviously, gorgeous - but the intense focus on her face was a little distracting.

All of a sudden, she ripped off her shirt and bra, calling out, "Suck my tits, my nipples, everything!"

I grabbed her rib-cage and started devouring her firm, delectable titties.

I licked, sucked, nipped, and nibbled her breasts, her areolas, and her nipples.

I had just started getting into it when she started yelling, "Stop! Stop! I can't stop. Fuck! Help me, Reg!"

She was still writhing on my hard-on.

"What do I need to do?" I asked - looking at her anguished face.

"Too fast. I'm losing control. Help!"

Despite every primal instinct within me, I grabbed her hips, lifted her off of my lap, turned her sideways, set her across my legs, and pulled her to my chest - hugging her.

"You're okay. I'm sorry. I shouldn't have pushed your boundaries."

She was sobbing, her breath gasping.

Her hand was between her legs - covering her sensitive sex.

I held her half-naked, trembling body and tried to do what I could to calm her.

She was doing that thing where you kind of hiccup from crying too hard.

I pulled her head to my lips and softly kissed her right temple.

"I'm sorry, Kase," I whispered.

She was still looking off, across the room.

"It was me too," she sniffled. "I want this. I want you. I love you. I hate you. I adore you. I despise you. I knew this wouldn't be easy. You make it harder cuz you're already turning into that copy of daddy that I have so desperately wanted for so long."

I hugged her closer.

Her face cleared - and I could see her brain working overtime.

"I will keep my promise," she stated finally. "I said a month. February has 28 days - which is four weeks. It's been six days; tomorrow will be seven. Three weeks from tomorrow - assuming I don't find out you're hiding something horrible from me - I will give you my virginity."

"So.." I began.

"What?" she asked, conflicted, still looking across the room.

"We have three weeks to figure out how this is going to work - the three of us."

She pulled back a little and looked at me.

"Up to now," I explained, "you've been able to consider my past girlfriends as historical. To a degree, I think you're doing the same thing with my relationship with your mom."

"Kind of," she admitted.

"You don't have to decide anything now - and I know you've thought about it - but this - three weeks from now - things get weird - or they get awkward - or uncomfortable."

From her seat, at the table, Mrs. Williams called out, "I'm all caught up. I can go another two years now."

Kasey laughed, "Like hell! I'm sure you've watched that video of your face when Reggie was fucking you. You're just gonna shut that off?"

"I can," she retorted.

Kasey turned to her and said, "I don't doubt that. You already have - and I know you're strong enough - but it wouldn't be right."

I kissed the side of her head again.

"You sound like you've already got this figured out," I chuckled.

"My brain does - but I know what you were asking me. Can my heart handle it? The answer, ultimately, is that I will make it - but - yeah - I've got a couple weeks to get myself ready for this - while still anticipating your naughty cock destroying my hymen."

"We should probably sit farther apart - if you're going to talk about my cock being inside of your pussy," I chuckled.

She gave me a light peck on the lips.

"You just make it worse when you do shit like that, you know?" she accused.

"What'd I do?" I asked.

"I think you know, Mr. Adorable. Now get your lumpy cock out of the crack of my ass."

"Speaking of ass..?" I asked, evilly.

"That's a hard 'no', buster. Get that shit out of your head right now."

I threw my hands up in surrender.

"Just playin'. You don't touch mine and I won't touch yours."

"You don't like a finger in your ass when you're cumming?" the MILFy teacher asked from the kitchen. "You don't know what you're missing."

"Mom!" Kasey complained.

"Yeah, TMI," I laughed.

I twirled a fingertip around Kasey's naked right areola.

"WTF?! Dude. Hands?"

"Sorry," I grinned, sheepishly. "You realize you're a succubus, right?"

"You should probably put some clothes on dear," her mom agreed.

"Well, he should be all primed for a little quality time with his favorite Science teacher," Kasey told her.

"I said she was the hottest; I never said she was my favorite," I retorted, grinning evilly.

Mrs. Williams crossed her arms over her chest, covering her milk-jugs, with a huff.

"You know I'm just funning, right?" I laughed, trying to extricate myself from the awkward silence that ensued.

"Right. If my finger - just accidentally - ends up in your rectum while we're having sex - I'm just 'funnin'."

My heart froze in my chest.

"Can I sleep with you tonight?" I asked Kasey.

She howled with laughter, turned to straddle my lap again, grabbed my face, and gave me a smoldering kiss - while grinding herself on me again.

When she'd finished taking my breath away, she stood up, grabbed her top from the couch, and headed upstairs, yelling, "I'm gonna turn my music waaay up, mom. Have fun!"

She cackled as she turned down the hall.

I heard the refrigerator door shut - and turned to find everything cleared from the table - while my former Anatomy teacher was removing the last of her clothes.

She laid on her back - on the dining room table - wearing nothing but a pair of white socks - with lace at the ankles - and hard leather, glossy black shoes with 1-inch heels. She raised her head to look at me. She was wearing the pair of glasses that made her look like a hot librarian.

She pulled her knees up, reached between her thighs to grab a hold of the heels on her shoes, and pulled them back - spreading her glorious sex open for the world to see.

In my hurry to get from the couch to my lover, I tripped over my feet and collided with the recliner - nearly breaking my dick in half.

Her hefty breasts were corralled by her arms, as they reached down her body. Her huge nipples were completely erect - and were pointing at her pussy.

Kasey had talked as if her mom & dad fucked all of the time - but this pussy wasn't a raggedy mess. It wasn't the perfect pink of a virgin - but it was super-attractive - especially when paired with the rest of her sexy body.

I didn't bother undressing; I just threw my pants & shorts to my ankles and - cock in hand - lined myself up to enter Heaven.

"I have an offering for you, Goddess," I proclaimed, sliding my penis into her velvety tightness.

My God! She is glorious!

Even without the little hot-secretary affectations, this woman was a vision of sexuality.

.. and, her body felt even better than it looked.

"Fuck!" I groaned, as I bottomed out inside of her.

"Yes!" she hissed, in agreement.

I paused - to savor the thrilling stimulation - and get enough air into my lungs to ask my question.

"Fucking or love-making?"

"I'm a naughty mommy, having sex with my daughter's boyfriend. I'm a slut. Fuck me like the whore I am. Punish my pussy - but I don't deserve your seed - shoot it all over me."

Her body had me rock-hard.

Her outfit had my balls aching.

Her words - the forbidden pictures she drew in my mind..

I was going to fuck the shit out of this beautiful woman.

I slowly slid my stiff cock out of her slippery channel.

She whimpered as it left.

I gave her a second to appreciate the absence.

The air - in the room - was cool on my slick penis.

I took my cock in my hand - and used it like a flyswatter - to punish her slit & clit.

She closed her eyes and bit her lower lip.

Worried I'd cum too fast if I used my cock, I slid two fingers into her quim - fucking them in & out of her - as my other hand rubbed little circles around on her clit.

When she seemed to be approaching an orgasm, I stopped, removing all stimulation for a few seconds, and then swatted her sex with my cock a few more times.

I took another break - and then repeated the process - bringing her back to the edge - causing her whimpers to intensify - and then spanking her pussy, again, with my danger noodle.

After the third time - I stopped completely.

Dick still in my hand - I lined up with her entrance - millimeters from her soft folds - no contact - so she wouldn't know what I was planning.

I reached my left hand around her raised leg & thigh, grabbed on, and drove my penis into her pussy - burying myself to the root - and throwing my right hand around the other leg to make sure I had a firm grip.

The air was forced from her lungs by the unexpected intrusion.

I did not give her time to recover.

Holding tightly to her legs, I started plowing my cock in & out of her clenching cunt.

I slid my hands lower - to where her legs met her hips - to strengthen my hold - driving in - each time - as hard & fast & deep as I could go.

"Whose cock is this?" I demanded, continuing to fuck her mercilessly.

"Kasey's," she moaned.

"Whose?"

"Kasey's."

I was getting close.

"Do you want my seed?"

"Yes!"

"Why?"

"I want your children. Breed me!"

"Did you ask Kasey?"

"No," she frowned, sadly - her emotions raw - I couldn't tell if we were still role-playing.

I felt my ball-sack whither and yanked my fuck-meat out of my lover - to shotgun my spunk back & forth across her body.

She convulsed each time my hot jizz splashed onto her gorgeous figure.

Her eyes were open - watching the jets of semen shoot from my dick.

She looked happy & sad - all at the same time.

She'd gotten what she'd asked for - but she looked disappointed just the same.

When my AK-47 ran out of ammo, I asked her, "Did you cum yet?"

"A little one - but I'm close," she admitted.

I leaned forward and captured her amazing ass in my hands, burying my face in her spicy sex.

She cooed at me.

I followed all of the instructions she'd given me in our previous lessons - the things to help both of us enjoy the act even more - licking, nipping, nibbling, and sucking.

I used my tongue to visit every part of her that I could reach - to stimulate every erogenous zone - cleaning her - adoring her - making oral love to my beautiful partner.

I looked up across her jizz-covered body to see her staring straight into my eyes.

I flicked her clit with the tip of my tongue.

Her fingers were slowly rubbing my seed into her ripe melons - swirling it around her areolas and nipples.

I could sense - and hear - her climax approaching.

Her body was tensing - her pussy was clasping - her clit was rigid.

I licked, rapidly, from the top of her perineum to her clit - sucked on the stiff bud for a second - and dropped back down to do it again.

Her body tensed and she moaned.

A second later, a short burst of her juices splashed onto my tongue as she screamed, "Fuck!"

I stayed there - tongue pressed against her pearly gate - to enjoy her sexy writhing - and reduce the amount of cleanup we'd have to do.

When she let go of her heels - and her legs flopped down on either side of me - I stood to help her rise.

She grinned, evilly, as she hugged her body to mine - smearing my spend all over the front of my outfit.

I laughed into her mouth as she captured my face to give me a wicked kiss.

"Oh, look," she said, grinning, as we separated. "Your clothes are dirty. I guess we'll just have to sleep naked."

I wanted to be mad at her.

I really did.

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51 Comments
L0vatL0vat26 days ago

Holy shit. Mack is awesome. Everyone deserves such a good boss.

KnightofmindKnightofmindabout 1 month ago

Still loved the story, truly. But: cock snot? Gross B. F'n gross.

kylady76kylady763 months ago

still loving it thanks

SilvermireSilvermire3 months ago

The premise IS weird, but baring that I'm enjoying the story.

AnonymousAnonymous4 months ago

The story does not make sense. There is no doubt that the boy is living his fantasy. He is having sex with the most beautiful woman he has ever seen and masterbating with her daughter who is simply a younger version of herself. The only way it gets better for him is to have full on sex with the daughter too. However, Cindy's dad exposed the elephant in the room when he told the boy to say hi to his mother. How does this kid just go off on a date and not come home for the weekend without any questions? How does he leave his car parked outside the Mill's house all night and most of the next day without the prying spying grandmother finding out? Also, the idea that the sexually experienced very horny MILF has no clue about birth control and has remained celibate after the death of her husband is laughable. The fantasy is Grand but the details of the story are terrible.

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