DDP - Jake Comes of Age

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A boy's first time should be with his Mom.
12.3k words
4.61
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110

Part 1 of the 3 part series

Updated 01/07/2024
Created 03/17/2023
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Cast of Characters:

Jake -- Our hero

Judy -- His loving mother

Janet, AKA "Aunt Janet"-- His loving stepmom, indisputable matriarch of the family

Jenny -- His half-sister and only child of Janet - a stunning beauty. Jake's protector

Steve -- His father, known for his inability to pull out

And the following list of ravishing women from whom Steve also did not pull:

Emma - Steve's older sister. Known for her hot temper and incredible bedroom skills

Deanna, AKA "Dee Dee"- Emma's oldest, and prettiest daughter

Gina, AKA "Fertile Myrtle" - Emma's middle daughter. Easily impregnated.

Sara -- Emma's youngest daughter, runt of the litter and all-around sex maniac

Laura -- Steve's younger sister, said to have the best tits in the family

April -- Laura's daughter and Jenny's best friend.

~~~

"Jake! JAKE! Get your ass out of bed!" Judy hollered up the stairs. Normally she'd just call his name up the stairs, but this was her third attempt.

Her son sure had been getting lazy lately. She wondered if it were just because he was 18 now, although a more likely explanation, to Judy anyway, was that group of low rent friends he had been hanging out with.

"Jake! NOW!!" Finally, she heard his feet hitting the floor.

~~~

The fact that Jake had the hottest mom of all his friends was indisputable. And the hottest sister. It just wasn't even close.

So, it was understandable that all of his friends were hot for his mom, whom we know as Judy. She stood five foot seven, with thick curly jet black hair, large liquid brown eyes, truly massive tits with perpetually erect upturned nipples, a narrow waist, and taut firm ass all rolled in to a package that looked much younger than her 36 years.

As if it wasn't bad enough that all of his friends wanted to fuck his mom, they all wanted to fuck his big sister Jenny too.

Jenny, his half-sister, was some 13 years older than Jake. She had a different mom, whom Jake had always known as "Aunt Janet", who was smoking hot herself.

Jenny was around five foot one, with thick luxurious nut brown hair that she kept tightly permed, striking hazel eyes, and perfect gleaming white teeth that shone from behind thick soft lips. She stuffed her firm perky tits and their pink puffy nipples into a C cup every day, although a D was probably a better fit. As if that were not enough, she was also gifted with a flat abdomen covered with rippling muscles, a remnant of her days as an elite gymnast.

But what really made all of his friends obsess over Jenny was her ass. Her absolutely perfect in every way ass. Oh, and her legs. Those were perfect too.

He was aware of it, and more than a little irritated with them.

Our story begins a few days before his high school graduation ceremony as he was hanging out by the local convenience store with a few of his friends, who, truth be told, his mother and sister found a bit objectionable.

Out of the corner of his eye, he spotted a woman from behind. His head snapped around, focused on the hottest butt he had seen all day. In his pants, his cock began to stir, until she turned around and he saw her face.

It was his mom!

She waved and began to walk toward him, her large firm breasts jiggling slightly with each step. His face flushed red with embarrassment at the thought that had flashed through his head. None of his friends noticed however, as all of his friend's eyes were riveted to his mom's tits.

"There you are Jake; Jenny and I have been looking all over for you!" she said as Jenny came into view from around the side of his mom's car.

"We're going to the Stars game tonight, if you want to go, you need to be home in one hour." she said as Jenny walked up and stood by her side.

"And here, carry your phone once in a while, will you, doofus?" said Jenny, handing him his phone.

Jake wanted very much to go to the game, and told them so, promising to be home within the hour.

Satisfied, Judy and Jenny turned and walked the short distance back to the car, all of Jake's friends' eyes glued to their fine butts.

As soon as the car doors closed, the comments from his friends began. He'd heard them all before, and was frankly sick of them already, but this time, when they started to argue over the best way to fuck Jenny, something in Jake just snapped. He turned and punched the nearest one squarely in the mouth, knocking him to the ground.

"I'm sick of you motherfuckers slobbering over my mom and sister!" he roared with an anger they had never seen from him before. He stared, making eye contact with all of them one by one, before turning away and walking slowly toward his car.

~~~

"Jakey, listen to your big sister. I never got to go to college. It was something I'd have loved to do, I'm just not capable of it. But you are capable! Your grades are exceptional, and you've already been accepted at an excellent school, less than twenty minutes away! You don't even have to move! You can still hang out will all your stupid friends up at the store."

"I don't think those guys are my friends anymore". Jake said mournfully.

"Uh oh. What happened, Jake?' Jenny said, her concern evident in her voice. She could see that whatever had taken place, it had hurt him very deeply.

"They talked shit about you and Mom all the damn time. I've been sick of it for months. And yesterday, Jeff was such an asshole that I punched him out."

"Jake!" Jenny gasped. She knew her little brother to be a kind and gentle soul. This must have been eating at him for a long time in order for it to come to violence.

"Jacob, violence is never the right response! I don't care what was said! whatever it was, it's just words. Fisticuffs are beneath you, little brother". She said calmly, doing her best to sound nonjudgmental.

"There's nothing he could have said that justifies a punch".

"He said he was gonna bend you over a chair and ream your guts out. I'm sorry, Jenny, I just lost it and punched him in the mouth".

"He said that about me, did he?"

"Yeah. He's said the same shit about Mom before too."

"And the rest of your so-called friends were good with that?"

"They were saying shit that was even worse."

Jake knew his sister's face better than any other, he'd seen countless iterations of it over the years. But not this one, and it scared him. Fuming, Jenny rose slowly to her feet.

"I'll be right back". She growled and walked straight out the door, slamming it behind her.

Half an hour later, the slamming of the door told him Jenny had returned. She walked into the room, calmer, but still obviously agitated.

"You won't have any more trouble from those shitheads". She said with a scowl.

"Listen to me good now, Jacob John Sanchez. Your friends are all losers. Do them a favor and stay away from them, because if you don't," She paused slightly, eyes blazing with anger, and lowered her voice to a menacing growl. "I'm going to have someone rip their balls off and feed them to the hogs."

He did not doubt his sister one bit.

~~~

"Yes, I heard. Apparently, her security detail stepped in and pulled her out. Probably to protect them from her!" Judy said with a little giggle. She paused and leaned a little closer.

"Jenny isn't wrong, Jake." Judy said softly. "She's been taking care of you all your life. She changed your diapers for god's sake! Yes, she may have acted too forcefully, but she did it because she felt it was best for you. If your friends don't respect your family, they don't respect you either."

She looked deeply into her son's eyes. "You can be so much more Jake. You have a brain in your head and unlimited resources to develop it. You know we're a wealthy family! Jenny's already talked to Aunt Laura. As far as the family is concerned, the cost is not a factor."

She paused and patted him gently on the leg. "Jenny and I just want you to make the right decision."

"I know mom, but I've been thinking, maybe college isn't for me, at least not that one." he said, remembering his campus tour and the smug attitudes of nearly everyone he met. "The people all seemed so fake".

"I understand, Jake. They're definitely a little pretentious. But a college degree will serve you very well! Remember whatAbuela always said? Once you have an education, no one can take it away from you."

Jake repeated the last few words along with her.

Yes, he'd heard his grandmother say those very words a hundred times. But Grandma Sanchez' family didn't have any money.

Jake knew his family was wealthy, and felt he had little incentive to bust his ass in college, especially that snooty one on the other side of the freeway.

"Jacob, if you just can't go to college, I understand. But look at this from Jenny's perspective. You know she still struggles with her dyslexia. College was always a dream, but never an option for her, even though everyone knows she was more than a good enough gymnast to get a scholarship. Think how much it would mean to her, Jake! Couldn't you at least try a couple of semesters? For Jenny?"

Jake thought for a moment about his big sister. He was seven years old when his mom had told him they'd be moving back to Dallas. Jake had cried at the news, right up till the moment he heard he would be reunited with Jenny.

He knew his grades were more than good enough for college. He just didn't want do it. At least not for himself.

He leaned back and took a deep breath. "You know I could never let Jenny down, Mom."

"That's my boy. Now I want you to go over to the business office get everything set up with your aunt Laura right away, before you change your mind again." Judy said, messing up his hair playfully.

"Thanks mom!" He said, and gave his mother a hug.

Pulling away, his hand accidentally brushed her left breast.

Instantly, both her nipples stiffened. She backed away quickly, hoping he hadn't noticed.

But he had.

"Sorry mom" he said sheepishly

Judy laughed awkwardly. "It's okay sweetie. That happens when a handsome young man touches me there".

Something about the look on her face prompted Jake to reach out as if to touch her breast again.

Almost without realizing what she was doing, Judy leaned forward, filling her son's hand with her big firm left breast. A low moan issued from her throat. Jake's other hand slid up under her shirt behind her back and unsnapped her bra, just as their lips met in their first true passionate kiss.

He pulled her shirt and bra off over her head, letting her magnificent firm round tits tumble free. Again, they found each other's mouths. It was several minutes before their lips separated and Judy spoke, just above a whisper.

"Tell me the truth Mijo; Are you a virgin?"

Embarrassed to admit it, he just nodded his head yes.

"Mijo, I'm going to do this with you, but you have to understand, No one can EVER find out, not even Jenny. It has to be our special secret, okay Mijo? She said, sprinkling in the Spanish word like she tended to do when she was stressed or nervous.

"I promise Mama". He whispered back, letting his hand drop from her big firm tit.

"Let's go up to my room, sweetie". She said softly, gathering up her clothing and taking him by the hand, leading him up the stairs.

.

Judy kicked all of their clothes into a pile at the bedside and climbed up the bed next to her naked son.

Their hot wet kissing resumed until finally, Judy pulled her son over on top of her.

Jake moved up tentatively between her wide spread legs.

"What happens if I get you pregnant mom? Do I need a rubber? Because I don't have any." he said, fearing that his chance to lose his virginity was slipping away.

"No, sweetie. A boy's first time should be bare. We'll go buy some condoms tomorrow for next time."

"Are you sure mom?" She nodded her head.

Without waiting for her to change her mind, he pushed his juicy young prick hard against his mom's slick wet pussy. The head and a couple of inches of his bare dick sunk smoothly into her. He pulled back and sunk in again, then again.

In just three strokes his long thick cock was completely buried in his mother's hot wet vagina.

"Oh Mom!" he groaned, and began to ejaculate deep inside her.

Judy wrapped her legs around Jacob's back and held him in, shuddering with her orgasm as her son's penis bulged and throbbed inside her.

Much to her surprise, Jake didn't soften a bit, and soon he was plowing his thick beef into his mom with long, smooth strokes.

He knew his dick was bigger than most, well over eight inches, yet he worried that he wouldn't be able to satisfy his beautiful mother.

He needn't have.

"Oh my god I'm fucking my son!" She thought as she moaned and rocked her hips, excited by the knowledge that his potent young sperm was already spreading out inside of her, searching for her eggs.

It was some twenty minutes later when Jake felt the familiar sensation return.

He tried his best to hold on, but his mom's pussy was so hot and wet, and her big firm tits were sliding around on his chest so deliciously, that he knew he could wait no longer.

"Oh mom... Mom I'm gonna cum again! Do you want me to pull it out?"

"No sweetie. You never have to pull your dick out of mama. Just cum... Just cum."

He knew there was a chance he could be getting his own mother pregnant if he came inside her.

He didn't know just how perfectly his mother 's ovulation had lined up to give him the best chance possible. And as his mother gently cupped his bag in her soft hand and began to lightly squeeze and roll his balls, he didn't care.

His mom was so tight and wet, and what she was doing to his balls felt so wonderful that he couldn't think of anything but the intense pleasure radiating from between his legs.

He sunk in to his mom all the way and felt his dick begin to throb.

Judy moaned softly as she felt her son begin to throb and pump his potent young sperm deep in to her fertile womb.

After four big throbs Jake started to pull himself away. She quickly locked her legs around his back.

"Not yet Mijo, not yet. Keep your dick in mama for a little while longer."

At last, he rolled off of her. Judy got up to pick through the pile of clothing at the bedside, tossing Jake his shirt and a pair of shorts.

"Get dressed Mijo, and hurry over to the office before your aunt Laura goes home for the night."

~~~

He found Aunt Laura sitting at her desk, talking to her lovely daughter and Jenny's best friend, April. Mother and daughter looked similar enough for one to know they were related, yet there were stark differences.

The biggest difference, pardon the pun, was Laura's magnificent thrusting breasts. Not that April's were chopped liver mind you, her firm round globes filled a C cup perfectly.

But Aunt Laura's... Oh my god. Firm pointy cones that appeared to jut straight out from her chest when her custom fitted bras came off at night, topped with pink puffy nipples about the size of a fried egg yolk.

Her older sister Emma, who gave Jake his golf lessons, had similar looking tits, but about half the size, and people still thought Emma had big tits.

Aunt Laura had sandy blonde hair, and April's was more of a strawberry blonde, but both let it fall in ringlets and curls to about halfway down their backs.

At a little over five foot seven, Laura seemed to tower over her daughter, who barely went five feet, but their beautiful shining faces were so similar, it was almost eerie.

"Jake! I've been expecting you! Have you made your decision?" she said with her prettiest smile.

Trying his best to look happy about it, Jake responded.

"I'm going to give it a try, Aunt Laura."

Laura knew he had been waffling on the college decision, and felt it had been because he was unimpressed with his campus tour. She herself thought it was in his best interest to visit several colleges, God knows his outstanding grades qualified him to go damn near anywhere. And being the family's business manager, she knew that if his grades couldn't get him in, the family's money damn sure could.

But the rest of the family wanted him to go to that college on the other side of the freeway in Dallas, (That I will not specifically name here, lest they hunt me down) mostly because it was close by, but in no small part because it really was an excellent school.

Either way, Laura was just pleased that he had decided to go to school at all. She knew he had a fine mind, and didn't care to see him waste it.

"I've already got most of the paperwork ready. Let me make a few more arrangements tomorrow morning, and I should have some things for you to sign by lunch". Laura said with a wry smile, pleased to note how hard it was for Jake to keep his eyes off of her tits.

~~~

There, on the counter, near but not that near to where she had left it, was the box of condoms she had purchased that morning. And it had been opened. Judy dumped the box out and carefully counted the packages. Ten.

She counted them again, although she knew she had counted correctly the first time.

A sick feeling welled up in the pit of her stomach.

She quickly walked over to the alarm monitor by the door and punched a few icons. In a few seconds, video of the last event began to play.

The video showed a car pulling into the driveway. Their little family compound was gated, it should not have been able to get in, unless someone had opened the gate. A young woman bounced out of the car and walked up to ring the doorbell.

"What a skank" Judy said to herself, assessing correctly that she was more than a little bit less than beautiful. Seconds later, Jake appeared, taking her by the hand and walking her back to her car. They stood beside the car and began to kiss.

To Judy's horror, the camera clearly showed the girls hand drifting to her son's crotch. A few seconds later the young couple hopped into her car and drove off, headed God only knows where.

Judy quickly pulled her phone from her purse and touched the panic icon on her home screen. Almost instantly, a deep male voice responded.

"Security".

"Where is my son! Where's Jacob!?!" The security coordinator sensed the level of panic in her voice. "Find him!" she wailed.

"Yes ma'am, we've got his phone. He's in a wooded area near a small pond about five miles from you. I'm sending coordinates to your nav system now." Grabbing her keys, Judy sprinted out the door to her car.

~~~

"Your ETA is thirty seconds" the voice of the security coordinator crackled through the speaker. "We're about a minute behind you".

Judy floored the gas pedal and the powerful V8 engine responded with a roar as she saw the gap in the woods that indicated her turn just up the road.

She was absolutely flying now, fishtailing as she made the tight turn and the car hove into sight.

The doors had just opened and the young couple were making their way into the back seat when Judy locked up the tires and skidded to a halt, mere feet from their wide eyed faces.

"Get in the fucking car Jacob! NOW!" Judy screamed from the window.

Shocked, Jake hung his head and walked to the passenger side.

Climbing in, he realized he had forgotten his shirt. The look of rage in his mom's eyes told him this was not a good time to mention it.

¡Aiejate de mi hijo pinche, puta! Judy shrieked out the window as she smashed her foot down on the gas pedal.

While his mom's Spanish was at least as good as her English, she never went full Spanish unless she was talking to a Spanish speaker, or she was incredibly angry.

It wasn't hard for Jake to guess which one applied here.

A heavy silence hung in the car for most of the short ride home.

When Judy finally spoke, her voice was still trembling.

"Just what the hell did you think you were doing, Jake?"

"I don't know mom". He muttered.

"Well, I sure as hell know what you were doing!" she said, voice already beginning to rise.

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