Every Schoolboy's Dream

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I didn't know if she was on the pill or not - but I wasn't about to stop to ask. I'd already dumped one load of my seed inside of her and I intended to do everything in my power to impregnate this woman.

She'd been asking - begging - for it and I was damned-well going to do my best to make it happen.

I kissed her face, nibbling her lower lip. I gnawed on those beautiful breasts, licking around her big stiff nipples and sucking them into my mouth like a hungry infant. I bit her jawline, I nibbled her ear, and went back to kissing those beautiful lips again - as I fucked her pussy.

She lay there - the whole time - watching my eyes.

Her fingertips were digging into my ass-cheeks, pulling me closer.

She wasn't letting me go until one of us climaxed - I wasn't sure if it would be her or me.

At that point, it was a race.

I was close - so close again!

She was moaning - humming?

I thrusted and drove and pounded - and finally the detonator went off. I drove my cock in deep - reaching for her womb - and growled, "Fuckkkk!"

As she felt my second batch of baby-batter blast inside of her, she pulled my face down to hers, kissed me passionately once more - and I felt the entire length of her vagina clamp down tightly.

Her eyes rolled back in her head as she hissed, "Yesssss!"

Long seconds passed before her body relaxed slightly.

Her arms wrapped around my shoulders and she pulled me to her generous chest. She held me there and whispered, "Thank you. You don't know how badly I've needed that."

I wrapped my arms around her, gave her a squeeze, licked her left nipple, and looked into those beautiful brown eyes.

"I really enjoyed our first date," I said, grinning. "I hope you won't think I'm being too forward - but I'd really like to ask you out again sometime. Could I steal a kiss before I have to say, 'Good night'?"

She looked at my face, and laughed so hard I thought her pussy would spit out my softening dick.

She glanced over at Kasey - who, I discovered, was still recording.

"So?" she asked her daughter.

"So what?"

"Is he a keeper?"

"Mom. I hardly think one good fuck is enough to make this kind of decision."

"Decision?" I asked.

Kasey looked at me, "Give us a minute."

Her eyes were serious - so I just nodded - with my cheek still resting between her mom's D-cup mammaries.

"Fine," Mrs. Williams told her. "You order while we're getting cleaned up and we'll talk about it."

"Delivery or drive-thru?"

"Drive-thru or eat-in - your pick."

"It's always better fresh .."

"Fine. We got an early start anyway. Reggie and I will go shower. Get us a table for three - for 30 minutes from now."

My former teacher looked into my eyes - and then looked back at her daughter.

"Make that 45 minutes."

"30," Kasey said. "I'm hungry and you already got off at least once - you can wait a little."

"Fine - but I have a lot of catching up to do."

"You know, it didn't have to be this way," Kasey taunted, grinning, "you could've just given into .."

"Say it!" her mom challenged, vehemently.

"Ugh! I can't," Kasey said, making a horrible face. "What a fucking creep! You know all those flowers were from him, right?"

"Can we not talk about Mr. Never Happening?" my former teacher asked. "I have a whole pussy full of the most beautiful spunk and you're doing this?"

"Sorry," Kasey said, her look reflecting her words. "You looked beautiful momma."

"Thanks, baby. It was really good."

"I kinda noticed," she said, grinning.

"Let me - us - shower real quick and we can talk on the way to dinner."

"After," Kasey demanded.

"Fine," her mother sighed.

Mrs. Williams and I lathered each other but - other than that - I enjoyed the chastest shower I've ever had with a person of the opposite sex.

We were done in 15 minutes, dressed in five more, and headed out of the drive - in my car - since it had been blocking theirs.

Mrs. Williams rode next to me - with her hand on my lap - while Kasey sat on the other side of her mother.

My car was old enough to have a bench seat in the front - instead of bucket seats. Whoever had decided that society needed a console between the driver and the passenger had obviously never had a hot female sitting - snuggled up against their side - while driving down the road.

One of my teacher's feet (and lovely long legs) was on my side of the hump in the floorboard - but - I was okay with that - very okay with that.

Mrs. Williams spent most of the trip to the Chinese place stroking the inside of my pant leg.

Kasey looked over now and then, shaking her head a little, but stayed quiet.

We ordered, chatted, stuffed ourselves, and then grabbed the fortune cookies.

As we read our fortunes to each other, we added the obligatory ".. in bed" to the end.

Mine was: "You will make someone's day .. in bed."

We laughed.

Mrs. Williams was: "Be ready for a new experience .. in bed."

She cooed.

Kasey's was: "The past cannot harm you .. in bed."

She looked pensive but nodded.

Mrs. Williams stayed quiet but squeezed Kasey's hand; under the table, her other hand squeezed my dick.

I stuffed the last Crab Rangoon in my mouth as we stood to leave.

Mrs. Williams leaned in and tried to nibble my lips - like she wanted to share it.

Kasey just shook her head - but took her mom's hand in hers as we headed to the door.

Since I was holding her other one, I'm sure the two of us looked odd "escorting" her mother to the car.

I opened the passenger door and Mrs. Williams shoved Kasey in first.

I let them both climb in, and then closed the door.

When I slid behind the wheel, I leaned into Kasey a little, to put on my seatbelt.

I looked into her eyes and said, "Hi."

She bit her lip again. I couldn't stand it anymore.

"I don't mean to scare you but every time you do that, I have this overwhelming urge to kiss you right in the spot where you're nibbling."

She stopped - looked me dead in the eye - and did it again.

I placed my thumb and the forefinger of my right hand under her chin, holding her gently, leaned into her, and said, "You are so beautiful it hurts."

I kissed her softly - just a little peck - at the point where her top teeth were biting on her lower lip.

I looked up, into her eyes, and felt like my soul was sucked into the void.

I cleared my throat, turned back to face the front, and started the car.

As I pulled out of the parking lot and headed for their house, Kasey laid her left arm across the seat, behind me, and lay her head on my right shoulder.

I looked over to see that her mother was holding her right hand.

None of us said a word - all the way back to the house.

We walked into the living room - but - I wasn't sure what was next, so I slowed down to follow their lead.

Kasey returned to her seat at the little four-person dinette.

Her mother and I sat on the couch - holding hands - sitting in the same spot where we'd fucked just an hour or so before.

"Kasey?" her mom started.

"Wait," she replied, solemnly , holding up a finger.

Mrs. Williams nodded.

Kasey looked from her mother - over to me.

~~~ The Rules ~~~

"Over the last year or so, mom and I have talked about our options. This experiment is the culmination of numerous brainstorming sessions.

Neither of us is certain that this will end up being the ultimate solution - but it's the closest we can work out at this time.

Part of the impetus for this approach was when mom and I were watching the 'Sister Wives' TV series.

I argued that the entire idea was ludicrous; mom countered that - if two or more females could come up with the correct set of ground-rules - they could make the relationship work.

So here we are. "

"Where is here?" I asked.

"I need to start with a little history lesson first," she stated.

"Okay," I agreed.

"Both of my parents were experienced lovers by the time they graduated high school.

In college, they were even more casual with their relationships. However, the day the two of them met, that all changed. Dad told me that he saw mom walk in the front door of his frat-house - for their regular weekend drinking party - and he couldn't stop staring at her. Within minutes, he had forced his way through the crowd, introduced himself, and pledged his undying love. Mom was intrigued but didn't know him - so promised him nothing - except to agree to start dating.

From that night forward, all other love-interests were pushed to the side. For mom, it was the logical thing to do - to give the experiment a true clean-room environment. For dad, it was his only chance to prove that his love was true.

Like any normal person would, mom started falling in love with this strange man who told her she was the center of the universe - and treated her like a goddess.

They were married six months later. Neither set of parents approved, thinking the relationship was doomed to fail. The ceremony was performed at the hall where the college's Christian Fellowship of Athletes held their meetings - by the resident minister. A handful of friends were the only witnesses.

Over time, mom's parents realized that the relationship was real - and gave mom & dad their blessing. Grandma Williams was, as is her nature, resolute. Grandpa, as you have probably already realized, has no self-will.

Grandma has never believed that mom was good enough for her son. To this day, she persists in treating my mother like she's some kind of cheap whore."

I glanced over at Mrs. Williams - who had turned many a clueless student into a success - by teaching them the value of learning for themselves.

"My parents finished their degrees. Mom completed her certifications and both of them started applying for jobs.

As most new graduates - and newlywed couples do - they struggled. Each time there was a need, Grandma Williams made sure she was there - with cash in hand - but - always - with strings attached.

When mom got pregnant with me, things, of course, got tighter - and grandma collected more IOUs."

I shook my head.

"Sixteen years later, when my dad passed away, Grandma Williams was more concerned about making sure her foot was squarely placed on my mother's neck than she was about grieving for her son.

Dad's will states that his estate will only continue to pay his portion of the bills as long as Grandma Williams signs-off on it.

Grandma has already promised that - the moment she finds out mom is dating - dad's money is gone."

"That's .." I began.

"Oh, it gets worse .." she declared.

I just waited.

"Grandma's tentacles don't just wrap around mom; they bind me as well.

Mom & dad had set up a savings plan to pay for my college but that money is under grandma's control as well.

I was only allowed to apply to the colleges and universities that grandma approved. I had to pick the cheapest one, regardless of any other criteria.

For the first two years, I will be attending the community college - here in town - and living at home - so that I'm not taking any more of Grandma's money than necessary.

After that, I will attend Eastern State - just down the road - and continue to live in this house."

I nodded.

"I really want to keep cheering in college. I can't do my classes - and cheer - and hold a job that would pay for everything I need.

Mom's job pays enough for her to get by - but not well enough to do that - and cover college.

Even if you can't see the bars on the windows - or the locks on the doors - we live in grandma's prison - and will continue to do so for the next four years.

Once I have my degree, we're cut off. Grandma tells me that I have five years, tops, to graduate."

"Wow," I said, shaking my head again.

She nodded.

"So - Sister Wives - the solution mom & I came up with was - to find an acceptable guy - and share him.

We needed a male - appropriately aged to pretend to be my suitor - so I created a spreadsheet, added the names of every person who I considered to be a realistic possibility.

We created a rubric and scored each of the potential candidates.

You scored the highest - so - here you are."

"A spreadsheet?" I asked, incredulously.

She nodded, her expression as serious as a heart-attack.

"Assuming you are willing, you and I will date for the next four years.

Grandma's spies will report that you visit me often.

Obviously, you will only visit when I am here."

I nodded.

"Again, assuming this works for you, mom will use you to take care of her sexual needs."

"So far, so good," I chuckled, glancing at my former teacher and back again.

Kasey gave a nervous laugh.

"At this time, I am still a virgin. Mom has, repeatedly, told me that she thinks I'm a little too old-fashioned in my approach to relationships.

Call it what you will, I want what mom & dad had - and I want it on my own terms.

Grandma seems to control everything else in our lives; this is one thing I control.

Part of the criteria I included in the spreadsheet was my calculation for the possibility of finding someone that I believed I could spend the rest of my life with.

Again, here you are."

She appeared to have a little more to say - so I just waited.

"I will not have sex with you - or any other man - until our wedding night.

You are free to fuck my mother - with no guilt from me - for the next four years.

I am interested in seeing if we're right for each other - but that is up to you as well.

Any questions?"

"You picked me?"

"The data did."

".. and you're okay with that?"

"You're here, aren't you" she asked, the right edge of her lip curling up a little."

I nodded, finding all of this a little difficult to process.

"The video ..?"

"As you have just learned, my mother has had to live under the constant malignant scrutiny of my paternal grandmother for nearly half of her life.

When she and I started talking over the details of this arrangement, I saw my mother's eyes light up with the first glimmer of hope since my dad passed away.

My father would have never forced my mother to give up sex. They committed their lives - and love - to each other and kept their wedding vows throughout their time together.

My mother deserves to be free to love and be loved - again - and to fuck if & when she feels like it.

She's been looking forward to her time with you since before you even agreed to participate in this experiment.

That video is for her - so she can remember what freedom looks like."

I reached over and squeezed Mrs. Williams' fingers.

"I gotta say, this is the weirdest conversation I thought I'd never have," I said. "I am concerned that it looks like you're trapped into having a relationship with me - just so that your mother can taste the freedoms that every other person already enjoys."

"Your analytical mind is part of what bumped your score above the others - that - and the fact that you never fucked around in school."

"I had three different girlfriends .."

"Who left you, regretted their decisions almost immediately, and tried to come back to you."

"Geez. How much data do you have?"

"My mom teaches Scientific Method .."

"Gotcha."

".. and you - never - not once - made a statement to anybody else about what happened in those relationships - even when they were throwing around all sorts of crap about you."

I knew which girl she was referring to.

"She was a slut. I never even fucked her. I think that was what made her the angriest. She was in such a hurry to have sex that I started seeing red-flags - so I just threw the brakes on the relationship."

"You were together less than a week."

"Yup."

"She spewed venom about you across the next three boyfriends - I'm not even sure she remembers dating them."

"Nick - from my Pascal class - was one of those three. She had him drive her to the city park. He said she held her hands over his face, so she wouldn't have to look at him, fucked him until she got off, and flagged down a passing car to hitchhike home. He was still pulling his pants up - climbing out of the backseat of the car - trying to figure out what happened - when she disappeared. He said she was fucking him so hard that he couldn't even get turned on - and two minutes later, she was gone."

"You cared about him?"

"He was always straight with me. He didn't deserve that - but nobody else had ever paid him any attention - so he jumped when she offered. I should probably get him a hooker when he turns 18 - so he can at least have one positive sexual experience."

"He's not 18? I thought he was in our class!"

"He is - was - he's just got a summer birthday."

She gnawed on that lip again.

I got up from the couch, squatted down in front of her, and kissed that same spot.

"So .. you seeing anyone?" I asked her.

She giggled.

I held out my right hand - and she placed hers in it. I brought it to my lips - kissed the back of it - looked into her eyes - and said, "You are the most beautiful woman I have ever known. You are smart, you are sexy, you are talented, you are strong - and I would like the chance to get to know you better."

She took my hands in hers and said, "I would like that."

"Speaking of fucking," Mrs. Williams called out.

I glanced, behind me, at my former teacher - and back to the young woman holding my hands.

"She's insatiable," Kasey said, rolling her eyes.

"Gotta keep my possible future mother-in-law happy, though, am I right?" I said, with an evil grin.

Her face got a little clouded - but she nodded.

"Hey," I said, pulling her chin up - so I could see her eyes, "I'm serious about getting to know you. Your mom is a terrific fuck - and a total hottie - but - if - I'm understanding what you're saying - this only works if you and I mesh, right?"

Kasey nodded, "Which is why she's anxious to fuck you again - because she's worried about how long it'll be before I find Mr. Right - and regardless of how she's acting like a total slut right now - she's terrified that Grandma will see through this whole sham and fuck us all."

"Grandma has spies?" I asked.

"She's suborned at least one neighbor and we believe she hired a private investigator. I don't know if you've looked around - but all of the curtains and blinds are closed - nobody will ever know what happened in here but the three of us - and - regardless of how you and I end up - mom needed this."

I did look around - and then back into those gorgeous eyes - those deadly serious eyes.

"Listen," I said. "I need to take care of an elderly friend of mine - but maybe I could stop and see you later and we could just talk?"

I leaned in and kissed her bottom lip again.

As I leaned back again, Kasey nodded at me, smiling a little.

"Elderly?!"

Kasey grinned and we looked over at her mother - as she was getting up off of the couch.

"Come with me, child, and I'll show you what this old hag is capable of. Let's go violate my marriage bed."

"Don't forget to shut down the laptop first," Kasey called to her mother, as I stood, "in case Grandma has figured out how to hijack it."

I had started to follow Mrs. Williams but turned back to look at Kasey - who was nodding - as she shooed me off to follow her mother.

"When she's done with you, I'll be down here, reading. Come visit for a while."

"As you wish .." I said.

She smirked, "Be careful, Dread Pirate Roberts .. She killed my father. Prepare to die!"

My head spun back to her - to see if she was being serious - but her mother grabbed my hand and pulled me up the stairs.

Kasey sat there, cackling with laughter, at the scared look on my face.

~~~ Round Two ~~~

Mrs. Williams and I entered the dark room - lit only by the nightlight in the bathroom.

My lover closed the screen on the laptop computer, left a trail of clothing on her way to the bed, pulled back the covers and laid down with arms open for me.