Every Schoolboy's Dream

~~~ The Proposition ~~~

I was standing on the front stoop of #24 Mulberry Street, holding a large pizza box, when the door opened to reveal a milf in a candy-apple red, form-fitting cocktail dress.

The lower hem of the eye-grabbing outfit went about halfway to her knees.

Her slender waist and long legs accentuated her lovely hips, which were not overly curvy, but told every male who saw her, "This is where babies are made."

She had on a pair of tan pumps that made her gazelle-like legs seem even longer - while not taking the viewer's eyes away from any of the more important parts.

The dress' top was strapless and sleeveless, which left her tanned arms and shoulders bare to the wandering eye - causing the mind to wonder if there were any tan-lines at all.

The full breasts, trapped within the tight bodice, looked like they were trying to escape.

Her dark brown hair had a little natural curl and hung down her back to her shoulder blades.

A thin gold chain, draped around her neck, enticed the eye to pause on her slender, scrumptious throat.

She wore no makeup; it was unnecessary.

Unlike so many, her eyebrows had not been manipulated into anything weird or unnatural.

She was, simply, beautiful.

I finished eye-fucking her gorgeous body and looked up at those intelligent brown eyes - which appeared to be waiting for my honest assessment.

You may ask yourself, "How do you know she's a MILF - just by looking at her?"

The answer, dear friends, is that - just two weeks ago - this absolute knockout was my high school Science teacher.

"Oh! Hello, Mrs. Williams. I've got your pizza here."

"Reggie! What a nice surprise!"

"Mom," Kasey groaned. "You specifically asked for him - by name - when you called in the order.."

"Hush," the woman told the teenager behind her, never looking away from me.

The girl - a younger version of the vision in front of me - was standing in the foyer.

This dazzling beauty was the woman's daughter - and my former classmate - Kasey.

Either of these women - could easily have served as the subject of a Luo Li Rong sculpture.

"So .. Reggie .. I have a personal question for you," the woman informed me.

"Um. Okay?"

My mind started analyzing this conversation - to figure out where we were going - and I had to reign my brain back in to focus on her words.

"Would you go out with me?"

I was tempted to look behind me - to see if somebody else had walked up. I hadn't heard anybody approach - and she had, specifically, said my name. She was, obviously, talking to me.

Was she really asking me out?

"On a date?"

"Yes.

Within nanoseconds, my brain analyzed all of the data I had available at this point.

So far, I had: hot MILF + me + some sort of activity that normally included only two people and had the possibility - however remote - of becoming intimate - but - at a minimum - meant walking around in public with the aforementioned MILF - likely giving me an excuse to hold her hand - and maybe even beg a kiss

"Um. Yes?"

"Just to be clear, I will have you come pick me up. We will go out for dinner - my treat. Afterwards, we'll come home, rent a movie, and end up in my bed for the night. In the morning, I will fix you breakfast and we may, or may not, have sex again before you go home."

Sex. I was sure that was the word. Pretty sure.

No. She had said it.

She'd suggested it when talking about her bed. Her. Bed. And then she had definitely said the word - and stated that there might be a repeat of the bed thing.

Not a bed thing where you lie there and read a book. Not sleeping. Not relaxing. Not talking about Science. Intercourse. Fucking.

She had said "sex" - and "again". Her bed. Sex. Me. Her. Sex.

Pretty sure I'm not confusing any of the details. I should still probably check though.

"You - and me?"

"Yes."

"In your bed?"

"Yes."

I stared at her in absolute disbelief.

She was still waiting for an answer.

"Just to confirm: The hottest teacher in school is going to feed me for free - and we might have sex once or twice?"

"Yes," she replied, a light grin curling the corner of her mouth and showing me dimples that I'd never realized she had.

"That's a hard 'yes', ma'am."

She grinned. I thought it might have been at the double-entendre with the word "hard" - but I didn't really care. She had said we would have sex - and she was smiling.

"Can Kasey watch?"

I, immediately, looked around at her daughter's face.

Kasey - hearing her name - and seeing my head spin her direction - cast her eyes to the tiled floor.

A couple of her teeth were worrying her lower lip.

She refused to look up at me.

Was she reluctant? Embarrassed? Afraid?

She hadn't run off.

She was waiting.

Waiting to hear my answer?

Sex with a total milf, while her hot daughter was in the room - and, possibly, watching?

"That would be her choice, but that's definitely not a problem for me."

"Splendid! Are you available next Friday - oh - and Saturday?"

At that moment, I had no clue if there was anything on my calendar.

Meeting with the President? Cancelled.

Ceremony for me to receive the Nobel Peace Prize? Fuck that noise.

"I am now."

"Good. How much do I owe you for the pizza?"

I looked down. There was a pizza in my hands.

Where did that come from?

I passed it over to the hot-ass teacher in the sexy dress and smiled.

"It's on me," I said. "See you next Friday!"

Mrs. Williams winked at me, and closed the door.

As I walked - well - actually - skipped - to the car, I could hear Kasey scolding her mother.

Kasey and I were two of the 87 kids that had graduated from Belmont High School two weeks ago.

Our senior class had three cheerleaders on the squad.

I'm probably a little biased but our three girls were hotter than all of the others put together - and Kasey was the hottest of them all.

Naturally-blonde hair - with just enough curl to hover between cute and hot, crystal-blue eyes, and a Baywatch body - she was a 10 on anybody's scale.

She had hardly talked to me during our four years together.

She was no prude - she didn't ignore me - nor I her - we just didn't operate in the same circles.

I was in the Computer Club; she was in the School Play. I was in Spanish; she was in French. I went to Scholastic Bowl practice; she went to Cheerleading practice.

Mrs. Williams was - as I had just told her to her face - absolutely, without question, THE hottest teacher at our school.

In the school yearbook, if there had been a category titled, "Teacher Most Jerked-Off-To by Students and Coworkers Alike", Mrs. Williams' picture would have appeared there - probably in that red dress.

Fuck!

Old man Jenkins, the janitor, disappeared into the mop closet - and locked the door for a half-hour - anytime he passed Mrs. Williams in the hall.

Word was that Mr. Sanderson - the principal - had been trying to cozy up to her ever since her husband passed away two years ago.

The people, I had talked to, claimed he'd even hit on her at the funeral.

Kasey absolutely hated the guy's guts - everybody knew that - so I had always kind of believed that rumor.

Mrs. Williams taught Biology, Physiology, and Anatomy.

She knew her shit. You were guaranteed to be ready for your college courses - if you survived her classes - but she didn't put up with any nonsense. She was as serious as Death itself.

Fuck around in her class and - if you were lucky - she'd just get pissed and send you to the principal's office. If you weren't lucky, she'd assign a paper to the whole class - due the next day - and, then, spend the rest of the period making you race to scribble down lecture notes before she erased the board and pushed on to the next chapter.

I had just been propositioned by Mrs. Doesn't-Fuck-Around herself!

I honestly couldn't tell you what happened the rest of the night.

Fridays are always big delivery nights - and I know - when I got home - I had a wad of cash in my pocket - but I had no recollection of how it got there - or anything else - after being told I was going to have sex with the world's hottest teacher - with the bonus possibility that her super-hot daughter might watch.

Holy. Fuck.

Needless to say, I didn't have to use much imagination while jerking off before I went to bed that night - or the next night - or the next.

I was enrolled in fall classes at the local community college - but didn't have any big plans for the summer.

Actually, my plan was to work as many hours as possible at Pop's Pizza, and save everything I could for a new laptop.

My desktop PC wasn't that old - but I was pretty sure I was going to want a portable - to be able to take it to classes with me.

If I got enough money to buy the laptop, and still had something left, the crap-mobile I was driving could really use some new tires.

Wednesday afternoon came, and I had a delivery down the street from Kasey's house.

I suddenly realized that I didn't know what time I was supposed to show up on Friday.

There was also a big chunk of my brain that wondered if Mrs. Williams had been drunk - or pranking me.

I decided that I'd better check.

I rang the bell and waited.

Kasey answered the door.

"Hey," I said, sheepishly.

"Hey," she responded, just as quietly.

"Um. So.. Friday..?" I started, nervously.

"It's okay," she gushed. "You don't have to. I'll tell her."

"What?! No! I.."

My eyes dropped. My brain went sideways. I looked back at her.

"Are you okay with this?" I asked.

She was back to staring at the floor again, biting that lip - so cute!

"Seriously," I said. "You say the word and I'll just go have sex with somebody else's mom Friday night."

Her eyes shot up to my face.

I grinned and winked.

Her tension evaporated, and she broke into a belly-laugh.

"Thanks .. thank you," she said. "I needed that. No. She's serious. You probably know that from having her in class. Fuck, this is so weird! .. but, no, she's been giddy all week."

"What time should I be here?"

"Oh. I think she expected you between five and six - she's not real picky about that part - more worried about later on."

"What time do you think?"

"Five. If you wait until six she'll start freaking out, thinking you're not coming."

"Okay."

I started to turn to leave.

"Hey?" she called.

"Yeah?"

"Are you seriously okay with me .. uh .. watching?"

"Other than me wondering if I can handle the pressure? No problem. Fuck. I'm so anxious about this that I probably won't even be able to get it up!"

I could feel my face flushing a little as I looked into her eyes.

"You know you have a huge hard-on right now, right?" she asked, grinning.

I looked down at the tent in my pants - which I hadn't even realized was there.

"Right.. Well. I MAY be looking forward to this a little."

"I should probably admit that I'm looking forward to it as well," she said, chuckling. "It's just harder for you to tell."

I looked down at her crotch which - obviously - didn't look like mine did but - as my eyes moved back up her body to her face - I noticed that her nipples (as tiny as they were) were rock-hard against the material of the T-shirt she was wearing.

My eyes lingered on those tiny, stiff teats a little too long.

22-calibre nipples, standing proudly, on top of those firm B-cup breasts .. almost C's ..

I suddenly realized I'd been staring, directly at her chest, for far longer than was socially acceptable.

I bit my lower lip and looked into her eyes.

"Hi," I said sheepishly.

She started laughing again.

"You should have been in Drama Club - that was very well done!"

I bowed with a flourish and said, "Why thank you, m'lady!"

She smothered a giggle and said, "I need to go but I'm .. er .. we .. we are .. looking forward to seeing you around five on Friday."

Not knowing how to finish my little act, I took her hand, kissed the back of it, and said, "Five on Friday - be still, my beating heart."

Halfway to the car, I yelled, "How should I dress?"

"Nothing fancy. A shirt and jeans should be fine, I think."

I waved my thanks.

In a repeat of Friday night, I finished the rest of my shift in a lust-induced fog.

My Wednesday night - and Thursday night - jerk-sessions were just as violent as the weekend's had been.

Thinking about Kasey's eyes on me - as I buried my prick in her willing-mother - was the stuff of fantasies.

Friday, I was up early - staring at the clock - which wasn't moving.

I'm pretty sure I showered three times.

Was the clock dead? No. The second hand was still moving .. slowly.

I was a wreck.

I had jerked off at least twice in the shower - but - as I drove to Kasey's house - I was already rock-hard again.

Why do I only see it as being HER house?

I had brought a duffle bag - with a change of clothes - but left it in the car so I wouldn't look like a dweeb.

~~~ The Revelation ~~~

The door opened and I stepped inside - to find Mrs. Williams in a sexy nightie - a red baby-doll that was nearly transparent - hiding behind the door - so that nobody outside (or across the street) could see her.

When this goddess had clothes on, she was gorgeous; when you could just make out her areolas - which were the size of silver dollars - through the material of the lingerie she was wearing ..

I just about jizzed.

She eased the door shut.

"I hope delivery is okay. I know I promised we'd go out but I can't wait any longer."

I raised my right hand to the side of my face - and clawed my fingernails into my cheek and ear hard - hard enough to make my eyes water.

"Reggie! What are you doing?!"

"Pinching myself," I replied, "to make sure I'm not dreaming."

Two motherly arms wrapped around me and drew my face in - to smother it between a pair of the most beautiful breasts I've ever seen in my life.

It felt like heaven. She smelled nice - and naughty - all at the same time.

My breath caught in my throat - and I must have passed out.

I woke up - lying on the couch - with my head on Mrs. Williams' lingerie-covered lap.

Kasey was sitting on a kitchen chair, next to us, fanning me gently.

When she saw my eyes open - and I looked over at her, she yelled at me, "You scared us to death! And you weigh a ton!"

"Okay, Kase! He's awake. Now can I fuck him?"

"Mom!"

"Kase! Baby! Mommy's SO horny. It's been two fucking years. I need a dick so bad!"

"Knock that shit off!" she growled, sternly.

I looked from daughter to mother (well, actually, I couldn't see her mom's face - my vision was filled with two gorgeous breasts) and back to the daughter.

"If it's all the same," I told my former classmate, "I'm not feeling that hungry right now."

Kasey stopped fanning me, and punched me in the arm.

"Yes!" Mrs. Williams yelled - as she bounced out from under me - and started unbuckling and unzipping my blue-jeans.

"Mom! At least take his shoes off first. For fuck's sake! Are you doing this right here?"

"Yes! I can't wait any longer. I'm so damned horny! I need him inside of me."

"Mom. He just passed out. You expect him to jump on top of you and start ramming his cock in? We don't even know if he's okay. Slow the hell down! Besides, you should probably start out on top - to give us time to see if he's alright - and time for him to get used to you. You're, seriously, a little too excited right now."

"Oh! Kase! You're probably right! Let me finish undressing him."

My shoes were yanked off - they went who-knows-where - and then my pants followed.

For an instant, she hesitated - looking at my tented briefs - I couldn't tell if she was savoring the moment - or having second thoughts - and then she whipped those to my knees and climbed onto the couch - to straddle my waist - without any further delay.

I briefly glanced to the floor - where the sexy negligee had been discarded - suddenly realizing that she had never been wearing panties.

"Oh! Yes.." she moaned, taking my dick into her hand, slowly starting to stroke it, apparently assessing the length and girth. "Momma needs a nice, strong cock. This cock will do nicely."

Kasey got up from where she'd been watching, grabbed the waistband of my underwear from where they were binding my knees, and pulled them the rest of the way off - throwing them on top of my jeans. Then she dug her phone out of her back pocket.

I completely lost track of what Kasey was doing when her mother - my former teacher - lined my stiffy up with her magnificent fuck-hole, and slid - so slowly - down onto me.

I looked into the eyes of the legendary Mrs. Williams as her quim swallowed my manhood.

Her weight settled onto my groin and I felt my balls brush against her ass.

I was - literally - balls-deep - inside of this woman!

The vagina - gently gripping my cock - flexing up and down the entire length of my penis - was unlike any I had experienced before.

The pussy I'd had before was scared and hesitant; this pussy was confident and powerful.

The other pussies had been cautious and uncertain; this pussy knew what it wanted and it knew how to get it.

"Mrs. Williams?"

"Yes, dear boy?"

"I love you."

"That's the cock talking," she chuckled, "but I'm okay with that. This old pussy has a reply for you."

I swear she never moved - her body didn't anyway - but it felt like four different people had grabbed my cock with their fingertips - and they were all massaging it at the same time - and somebody was teasing the bulbous head.

My eyes had to have been as big as saucers.

Mrs. Williams leaned forward, held my face in her hands, and kissed me like it was our wedding day.

She started slowly fucking, fucking, fucking, fucking, fucking, fucking, fucking..

I couldn't breathe.

Her lips were still locked onto mine, her pussy was dragging, grinding, gliding, sliding, pumping, pulsing, pulling, sucking, slurping, ..

Oh, shit!

"Mrs. Williams!"

My words were strained - there wasn't really enough air in my lungs to get them out - to warn her..!

Her mouth was still locked to mine - the words were trapped inside between us.

Her lips released mine, moved to my left ear, and she growled, "Do. It."

My balls erupted - like a water balloon - left too long on the garden hose.

I swear I whimpered as I felt my seed explode from my testes - race through my cock - and jet into her perfect pussy.

She was holding me tightly - my dick buried as deeply as it would reach inside of her incredible tension. The tip of my penis tingled as it just, barely, brushed up against the entrance to her womb.

I don't think I've ever cum so hard in my life!

She waited until I was done, and then went back to riding me.

She wasn't as gentle this time - a little more needy - but it was still love-making, rather than fucking.

This was not going to be a one-night stand - I could already tell.

Her eyes, her body, her moans - she intended for this to be a regular occurrence.

My poor penis had just started to soften inside of her when she seemed to be getting close to cumming.

Her excitement rubbed off on me and my dick started hardening again.

Her love-making was turning into fucking; her groaning had turned to growling - and I was suddenly ready to answer the call.

I wrapped my arms around her thin waist, spun us sideways - and then continued rolling until her body was lying where mine had just been - and then I started pumping my cock in & out of her creamy cunt.

"Fuck, yes!" she moaned. "Breed me."

There is no way I should've been ready to go again that fast - except that my hot-ass MILF teacher was moaning and calling my name and begging me to knock her up.