Timmy Becomes a Man

Alison froze in place. Peeking over her shoulder, Timmy could see a huge figure filling the door at the top of the short staircase. Joan Bailey - their mother, appearing just in the nick of time to save her beloved son from being raped by his own sister!

Did he WANT to be saved? He had no answer for this. He gave a mental shrug and doubled his efforts, suckling on his older sister's tit as if there was no tomorrow; for all he knew, there might NOT be...!

Mrs. Bailey made her way down the stairs. She was a big woman - 5'11" or maybe even 6', with shoulders almost as broad as her daughter's and large, heavy breasts that swayed as she navigated the narrow stairs, her conservative workout outfit doing very little to hold them in place. Timmy, however, was fixated on the look on her face. Their mother was very obviously angry, even enraged, and he felt a thrill of excitement. Were those two Amazon women going to fight each other? Their mom wasn't as muscular as Alison, but she was a bit larger, and also very strong...

"What THE HELL were you thinking, Alison?! You were going to FUCK your brother? Don't you have any sense of PROPRIETY?!"

Alison, having apparently overcome her initial shock, straightened up, hugging her brother closer, one rough palm cupping his soft butt.

"Mom, he turned 18 TWO MONTHS ago! You can't expect me to wait forever!"

Joan now stood in front of them. It was obvious she was trying to calm down, her voice more quiet, but her rage still showed.

"I TOLD you I was waiting, that dad thought he was too small, he begged me to hold on, but you KNEW I wanted to be his first one, how COULD you..."

"Seriously, mom, you're being so old-fashioned..."

"Old-Fashioned? Seriously? That's what you're going with? How about you're just a selfish little shit daughter who couldn't hold her dick in her pants..."

"Oh, come on..."

As the two amazons faced off, their word started registering in Timmy's brain. Did his mom just say... Alison has turned, and he could now see their mom's whole body; and, yes - there it was. Her cock - which he knew to be much bigger than his sister's - was clearly showing under her loose t-shirt, free of restraint and fully aroused... he stared at it for a moment, his jaw loose, the implications swirling in his brain, as the two Futa continued to argue, their words a jumble, incomprehensible...

He raised his hand timidly.

"Mom..."

Joan stopped her tirade and stepped up to him, her expression changing as if by magic, a loving smile replacing the angry snarl.

"Yes, baby, mommy is here..."

Timmy struggled to speak.

"Mom... you... you're going to FUCK me?"

Joan put her hand on her son's cheek and smiled at him warmly.

"Yes, baby, I waited too long, I'm sorry, I know how much you must have been waiting for this...!"

Timmy cringed under her touch. Did she really think... well, she was obviously presuming too much, sure, but... was she, really? He felt overwhelmed by all the things that have happened over the last 10 minutes... there was the whole hour before that, of standing over his sister as she worked out in her tiny outfit, her mighty muscles glistening with sweat, her tits almost bursting loose with every movement, her package always there, bulging and shining... Holding his naked body against her, now, her rough hand kneading his buttocks, her cock huge as it rubbed against his own, tiny one...

And now, here was their mom: the woman he had been fantasizing about for years, standing in front of him, her light chestnut-brown hair held in the familiar, loose bun, her green eyes filled with love for him, her great chest heaving - and her gigantic cock, which he'd at most seen rolled in her pants, dormant, as she worked around the house, now very much free and aroused - and terrifyingly huge, even hidden by the hem of her loose shirt.

"Mom, I... I'm not sure..."

Joan cut him off, impatient. "OK, we're just wasting time. Dinner is at 7 and your dad should be home any minute, now. He's had a very rough day at the factory, today, I don't want him to fall asleep at the TV waiting for us. Where do you keep the lube, Alison?"

Timmy almost choked, trying to speak. She was seriously going to do it! Good god, he needed to DO something, STOP her! Alison, too, was taken aback.

"Com'n, mom, you can't be serious! You're too big, we need to prep him for at least a couple of days, use the butt plugs..."

Joan waved her hand. "Nonsense! I fucked your dad 20 minutes into our first date, and he was totally fine! Lots of crying and a little blood, but otherwise -..."

Alison hugged her brother closer. "Mom, you were, what, 10 inches back then? 11? You can't expect Timmy to just..."

"Alison, please! You're scaring the boy!" Joan smiled at him reassuringly. "Don't listen to your sister, baby. It's a bit painful at the beginning, but then it's just amazing and you'll love it and just want to be fucked non-stop! Here, look at those in the meantime..."

With one swift move, his mother pulled her t-shirt off, and Timmy's mouth - which was beginning to quaver with fear - dropped open. His friend Matt, who was considered an authority on such matters, estimated she was a 34DD, and he had of course seen her in a tank top, but the reality of his mom's naked boobs was so, so much more... They were huge, creamy, perfectly round orbs, spilling over her surprisingly flat belly. The large, pinkish-red nipples were pointing downwards, but it seemed that relative to her age and their considerable mass her breasts had fared remarkably well... He couldn't help himself; he let go of his sister's torso and reached out with both hands for his mom to pick him up.

Alison snorted in disgust. "You're such a slut...!" She slapped his butt, eliciting a yelp of pain from him. "Don't you think you'd better see what you're getting into, first?"

Joan laughed happily. "Oh, I think he knows, all right!" Her loose workout pants were nowhere as sexy as Alison's Lycra bikini bottom, but they were tenting mightily, the drawstring pulled tight to hold it locked inside. She now fumbled at it, and after a moment it gave up, its tight hold around her generous hips giving, the pants beginning to slide down. The beast that suddenly sprang up out of it looked like nothing of this world.

If Alison's cock was twice his own size, this looked like it tripled it. It was at least a foot long - probably more - and much, much thicker, thicker than a can of soda, much thicker than his arm... And it was veiny. Where Alison's cock was fairly smooth, almost friendly-looking, his mom's cock was a snarling monster, with a thick grid of dark veins running up and down its girthy length. Timmy pulled back at the sight with a stifled exclamation, for the first time as an adult knowing the meaning of true fear. As a kid he has been terrified of the imaginary monsters under his bed - well, here was a real one, and so, so much scarier than anything his juvenile imagination could have conjured!

Alison gave an evil chuckle as her little brother clung to her, whimpering slightly.

"Not so keen now, are you? Well, tough luck, because your mom has decided to drill you a new one!"

Timmy was crying now as he hugged his sister with all the strength he could muster. He raised his feet and locked them around her thick thighs, just under the perfectly globular buttocks. Oh, what he wouldn't have given to be fucked by her - just so he could keep his mom's Anaconda away from his poor butt!

Joan sighed audibly."Really, Alison... I'm sorry I didn't discuss this with you, I should have guessed you were dying to fuck him, too, but there's no point scaring the child. I'm his mother and I have the right and the DUTY to be his first. Just get the lube and I'll get it done and then we can ALL fuck him in peace."

Alison moved to the old work desk standing next to the wall, carrying the whimpering Timmy with her. She opened the top drawer, took out a large tube and tossed it to their mother.

"Yeah, I guess I fucked up, too. Should have just talked to you. Sorry."

Joan reached out and touched her daughter's shoulder briefly. But there were more urgent matters at hand; she squeezed a large handful of clear jelly onto her hand and started rubbing it on her gigantic cock. Alison turned her attention to her brother, who was now sobbing, his head on her shoulder, his tears running free. She hugged him close, hoping the effect of her boobs and her cock would calm him down. She stroked his hair gently.

"It's OK, sweetie, it's OK, it looks much worse than it is, and mom is going to be really gentle with you..."

"But... but... [SOB] she is so [SOB]... so BIG!!"

"I know she is, Timmy, but you're a big boy, now, you can take it..."

Timmy looked up at her, his tear-streaked face desperate.

"How?! I'm [SOB]... I'm five six, I'm [SOB]... she'll... she'll tear me apart!"

Alison wiped his face with her hand, her face serious. "Dad is five eight, he's not much bigger than you, and look at him. It's like mom said: it's going to hurt a bit, and then it's like heaven, seriously! And once you do it, we can fuck like crazy... Kevin won't be back till next Tuesday, and I promise I'll be fucking you every day..."

Timmy almost laughed. A mere 10 minutes ago the thought of his sister putting her cock in his ass was a blood-curdling threat - now it looked like salvation... but the feel of her body against his - the hard muscles, the soft breasts with their diamond-like nipples, the thick pipe of her cock; they all felt so familiar, now, friendly, comforting... He tightened his hug.

"Just don't... Please don't leave me..."

"OK, baby, come to mommy... Time to become a man!"

His mom was standing, her arms stretched out, beckoning to him. Now completely naked, she was at once the most erotic and the most terrifying sight Timmy had ever seen; smiling at him, as beautiful as ever, her luscious breasts with their red flower-like nipples inviting him to feast on her gorgeous body - but her humongous cock, shining with lube, on top of a pair of ginormous, glistening balls, all threatening to tear his delicate body apart... He squealed in fright and clung to his sister, whimpering pathetically.

Alison sighed and gave her mom a chiding look, but held off from saying anything. She patted her trembling brother's head, and spoke softly.

"I'm here with you, Timmy, I won't leave you, OK? This is what we're going to do..."

She walked over to the large bench press station, and turned, walking backward, straddling the bench. She stopped before reaching the overhead bar, and slapped her brother's butt playfully.

"All right, this is where you get off."

Timmy looked up at her, his face fearful, but his older sister was now in her practical mode - 'getting things done'!-Alison. She grabbed his sides, and without much effort tore him away from her, lifting him up in front of her, then placed him on the bench. He was on his elbows and knees, his soft butt up in the air, his face raised up to her, full of apprehension, looking so sexy that Alison was very close to changing her mind and challenging their mother for the right to be his first. Damn, he was so HOT! But, no, she knew Joan was right; she was the boy's mother, and she should be the one to fuck him first... She was just going to have to pray that the poor boy's asshole would survive their mother's monster attack, so there'll be something left for HER...!

***

Timmy was trembling as he awaited the devastating attack he knew was coming. He had been fantasizing about his mom and her cock for years, but he had never even imagined its true scale... His dad's slightly-comical, bow-legged "cowboy" way of walking suddenly made absolute sense; good lord, that poor bastard has been taking that monster up his ass for almost 22 years...

Counterpoint: his dad was also one of the most relaxed, seemingly-happy people Timmy knew...

His sister was now sitting in front of him, her magnificent rack slightly above his head. He has of yet not had any cock go up his ass, but the other part of the package - sucking on his relatives' tits - had turned out to be as great as advertised; maybe he should just try and relax, just... experience those things as they happened, instead of working himself into a state of utter panic? He strained his head up to look at his sister's face, and spoke, trying his best to sound nonchalant and carefree:

"Hey, sis - mom is going to make a real man out of me!"

He was proud of the way he'd kept his voice almost level, with only a bit of croaking. His sister thought it was hilarious, guffawing loudly.

"Getting a little cocky, aren't we? Better hold on to me..."

There was a heavy weight suddenly laid on his back. His mother's pole - huge, intimidating and very greasy - landed on his buttocks, sliding forward through his upturned butt crack and onwards down his spine, and suddenly she was leaning down over him, strong arms planted on his sides, her great breasts squeezing lightly into his upper back and her face near his head, nibbling on his ear.

"I've been waiting for this for so long - I'm sorry, baby, I was stupid to wait, but I'm going to make it up to you..."

She gave his half-turned cheek a sloppy kiss.

"I love you very much, baby, and I'm now going to show you just how much..." She started to rise. "Hold on to your sister, baby..."

He grabbed his sister's chiseled midriff with one hand and braced himself, feeling the great beast sliding back along his back. He whimpered softly as he felt greasy fingers digging between his butt-cheeks, his mother gently playing with his back door, slowly prying it open. He wriggled helplessly, trying to pull away, but he was trapped between those two amazonian Futas; there was no escape, nowhere to run - his mom would not be denied...!

Alison took hold of his shoulders, pulling him up slightly, and he attached himself to her right breast, and started sucking eagerly. The fingers that were playing with his hole were now holding his cheeks spread, making way for a new player. He could feel a giant, bulbous, fist-sized giant pressing between his ass cheeks; his mother's monstrous glans was about to enter his ass...

He gave a small, fearful whimper, but never stopped sucking on his sister's delicious nipple. She cooed at him approvingly.

"Nice, baby, you're doing great... So brave... Yeah, that's it, play with your tongue..."

The guest at his back end slid back a little, then slid forward, bumping against his tiny, tightly-clenched hole. He almost laughed; there was no way that baseball bat-sized thing was going in there... They were just having a laugh at his expense...

Another slide-back, then - another push forward, bumping into him a little harder. He grimaced; yeah, he felt that - but no way was this real, he was not falling for it...

The fingers holding his buttcheeks apart suddenly withdrew, and then they were gripping his hips and he gasped as the next shove shook his body, the tip seeming to actually push slightly into his puckered-up rectum. Alison cooed at him soothingly, but he felt the panic return; this was a bit painful, if it went on, maybe...

His world exploded.

It was not "painful". Painful is when you stub your toe against the table leg, or you have a tooth extracted; this, on the other hand - this was like nothing he's had ever experienced. His mom's glans - that fist-sized, purple mushroom head - had broken through his tiny ring. And it HURT. It hurt like HELL. The pain - AND the surprise, because no way did he really believe it was possible - made him scream into his sister's boob, a desperate cry for help.

Alison put a hand on his hair and smoothed it lightly, clucking at him, her voice filled with sympathy.

"Oooooh... That part is the worst, your first time... But you're doing great, baby, the worst part is almost over...!"

He knew she was lying, because his mom was now pushing herself forward, further into his rectum, in short, powerful bursts, and her stem was almost as fat as the head, with those monstrous veins cutting into his delicate pipe... He whimpered pathetically, stopping himself from biting down on the nipple in his mouth. This was hell... He tried to wriggle, free himself, but the hands holding him on both sides were just too strong, and his mother was feeding her massive cock into his ass, pushing forward with short, powerful bursts, inch after agonizing inch...

"That's great, Timmy, really, you're taking mom's cock like a champ..."

He pulled his head back and looked up at his sister, pleading, his eyes filled with tears.

"It's... it's too... it's too BIG... I can't..."

Her eyes were filled with real empathy as she bit her lower lip.

"Oh, I know, baby, I know she is... Maybe, mmm..."

Her hand left his side, again, and suddenly there was a new sensation, as something new was rubbing against his chest and throat. He glanced down and saw that she was holding her rigid cock in her hand, bumping it against him, the pink head teasing him, tempting him to take it in his mouth, suckle on it... He moaned in pain and frustration. No, it was too much, the unbearable pain in his ass was just too much, he couldn't...

***

Joan stopped her thrusting, giving the boy a moment to try and acclimate to her size. Alison had of course been right: she WAS too big, she should have prepared the boy before actually entering him... But she had taken too long. Going against her best instincts she had put it off, afraid her enormous size would hurt the poor dear - and now, having seen her vixen daughter ready to take him, she was out of options. There was no way she would allow anyone else to deflower her own son!

She felt resentful of Alison, but she'd also appreciated the push she gave her, and the help she now provided, holding the boy and soothing him. But now it was time for her, as his mother, to take over, make the boy truly hers. She looked down at his perfectly round, smooth butt, impaled on her thick womanhood. She only had 4" inside him, and this is where it was about to get interesting...!

She pulled back a little and adjusted her stance slightly; her well lubed cock was held tightly by the narrow confines of her son's ass, but her new angle of attack had the maximal effect as she renewed her barrage. She smiled happily as the boy started writhing like a madman, gibbering unintelligibly; she had been fucking men for 3 decades, now, and if there was one thing she was perfect at it was hitting their P-spot...! She slid back and forth, feeling the small bump as she pressed down on the magical gland, purring with delight. She knew Timmy was still in unbelievable pain, his tight tunnel and tight ring not yet suitable for her immense girth, but he was also now starting to realize the magnitude of the pleasure to be had - as proven by the spurts of whitish cum he was ejaculating on the bench below him...

She was more than halfway in, 7"-deep into his rectum, and she knew all too well how terrifying the feeling of her womanhood sliding up a man's colon could be. She found the way men reacted to it to be almost comical, loved watching them panic as they felt their body's very anatomy being rearranged; but this was her beloved son, and she couldn't let him face this without his mother's loving guidance. She moved her hands up his sides, closing her strong fingers around his rib cage. She nodded at her daughter, who let go of her brother's shoulders, letting their mother take over.

Joan flexed her mighty cock, using it as a pivot, and then, slowly, lifted her son, bringing his back up against her body, bringing him to rest against her giant boobs - all with his ass firmly impaled on her mighty cock. She kissed his neck, then nibbled on his ear.

"You're taking mommy's cock so well, baby... I'm so proud of you..."