Part 105: Take It to the Limit

Day 73: Wednesday, November 27

Chapter 1

Alan woke up, opened his eyes, and languidly stretched his arms. He glanced around and slowly came to the realization that he wasn't in his own room. He was actually in his mother's master bedroom instead. Suddenly, memories of how he'd fallen asleep with Katherine on one side and Susan on the other flooded into his consciousness.

He smiled widely and his arm stretch turned into punches of joy in the air. Yes! Now THAT's how a guy should get some sleep! Not only that, but I actually feel fairly rested. After all the sex I had yesterday, I'm surprised I don't feel like being wheeled off to the hospital.

He paused and did a double-take around the room. But wait. I'm alone. Where's Mom and Sis? Shucks. I was kind of getting used to this waking up with a good morning blowjob thing.

Just then he saw the door to the bedroom open up as Susan and Katherine tumbled into the room. He got the impression that they'd been peeking through a crack in the door. Both were wearing high heels and not much else. Susan wore an apron and Katherine wore a skimpy outfit in a leopard print.

"Good morning, Big Brother!" Katherine said enthusiastically as she came close.

Susan followed behind her and said in a throaty and surprisingly low voice, "Morning, Son." She was carrying a tray and wore a smile that seemed somehow both matronly and extremely sexy.

He looked at both of them with an eyebrow raised. Knowing they were being examined, they closed their eyes and thrust out their chests. He hadn't woken with a hard-on, but that "problem" was fixed in a matter of seconds. "Mmmm. You two look good!"

Katherine sat on the bed on one side of him and Susan stood on the other.

Katherine beamed with delight at the mild compliment and said, "What? You're acting like you're never seen us before. Of course we look good, Big Barbell Brother. We always look good!" She straightened up and proudly thrust her chest forward.

Alan laughed, pleasantly surprised at her blatant self-confidence. "I know, I know. It's just that you two look exceptionally lovely this morning. Sis, I love your jungle-y little leopard outfit. I could definitely get used to having a pet around here."

Katherine bent her head down and forward, inviting him to pet her long dark brown hair, which he did with one hand. He looked down at the spotted bikini she wore and with his other hand he pulled her breasts out of the top. Since it was a strapless bra, it easily fell down around her stomach.

"Ah. Much better," he sighed contentedly as he began to fondle his sister's big breasts.

Katherine giggled and cooed. She seemed particularly happy and easy to please. She purred, "And I could definitely get used to being your fuck toy pet around here."

He kept his hands on his sister but turned around to face his mother. "And you. You're looking fantastic, too. I love the apron look."

Susan beamed proudly at her son. "I love it too! The apron reminds me I'm your mommy, and the nakedness reminds me I'm one of your sex toys. I get all tingly down below just putting an apron on!" She wore an erotic white apron. It covered her nipples, but just barely.

He took his hand from Katherine's head and brought it to his mother's chest. Her large boobs were covered by the apron, but he quickly pushed the apron to the side so her huge boobs could swing free. "Aaaaah. That's more like it. What's with both of you covering up so much today?"

Susan laughed. She stuck her tongue out and playfully mocked him as she covered her boobs with the apron again. "I'd hardly call this fully dressed. But Suzanne taught us it's more fun getting naked than starting naked."

"True enough," He agreed as he looked from mother to sister and back and let his hands wander freely over both of them. "But I must say I'm a bit bummed that I woke up all alone. I was kind of looking forward to waking up with you two by my side."

"So were WE!" Katherine blurted out. She furrowed her brow, and looked up at Susan unhappily. It was obvious the two women had disagreed about this earlier. "But unfortunately, you told us to take it easy on you and let you sleep in. If it were up to me you would have woken up in mid-orgy, but you said you were tired so we had to respect that." She straddled herself over her brother's legs to give him easier access to her body.

"Oh. Yeah." He was still coming to and trying to recall all that had happened the night before. "True. Thanks for doing that. I slept in? How late is it, anyway?" He looked at the alarm clock by the bed as he said this, then exclaimed, "Seven twenty? Shit! Fuck!"

"What's the problem?" Susan asked, not at all concerned by the time. She seemed to have some kind of happy secret.

He looked down at the bed next to where his mother stood and saw that she had his breakfast in a tray there. Even as he continued to run a hand over her hips, she bent down, picked up a fork, and brought a bite of waffle to his mouth.

He thought, Today I'm supposed to help out with a bitch training session with Heather before school, but I can't exactly tell them that. They'll be offended ... Hell. Why not? Total honesty is good.

He took a bite, swallowed, and then said, "Mmmm. Thanks. Um, to answer your question, I uh, well, it's like this. I have an appointment before school."

Susan and Katherine looked past him and at each other. Both raised eyebrows quizzically. "Oh?" they said in unison.

He stopped fondling his sister's chest, closed his eyes in mild embarrassment, and said, "Yeah. It's with Heather and Simone. I imagine there will probably be some fucking going on."

There was a pregnant pause. Surprisingly, there were no words or even murmurs in response.

He opened his eyes to get their reaction since he hadn't heard anything. He looked at Katherine. He could see mild annoyance on her face, but she was trying to put up a brave front. He was pleased to see her smile at him encouragingly. He smiled back.

Then he looked up to Susan.

She grinned like an idiot, she was so happy. "I'm so proud of you, Son! Slipping in a quick fuck with the busty head cheerleader and her busty black friend before school. I love it! Two at once, just like you're doing now with Angel and me! I'm so impressed and proud of my manly son that my heart could burst out of my chest!" She surged forward a bit and brought a hand to her chest as if to stop her heart from breaking out of it.

Alan chuckled and quipped, "That's not the only thing about to burst from your chest, Mom. Is it my imagination, or have your tits grown overnight?"

Nothing could have made Susan happier than to hear those words. If she was beaming before, her face positively glowed with happiness now. "Really? You think?" She was shy at first, but then with determination, she added, "Why don't we find out? We weren't sure if you'd be in the mood after all that happened yesterday, but I think little Alan Junior wants to come out to play, doesn't he?" She brought another fork-load of waffle to his face with one hand and pulled his covers down with the other.

"Not-so-little Alan Junior," Katherine corrected as Alan's hard-on came into view and sprang straight up. "God DAMN, look at the big cum-filled thing! I've missed it so much!"

"I stand corrected," Susan smiled. "Big, thick, iron-hard sister-and-mommy-splitting Alan Junior, I should have said! Quick, Angel, you take care of Alan's tragic sperm surplus and I'll help him eat."

Alan chewed his food and then said contentedly, "Now, that's more like it. What a nice morning." Then he frowned. "But the time! I can't keep Heather waiting! You've heard what a bitch she is."

Susan replied, "There, there. We've been up for ages and we've got it all covered. Your clothes are laid out and I'll drive you to school and everything. Ten minutes of sisterfucking to warm up your cock while you eat breakfast, which you have to do anyway, and you'll be slipping into either Heather or Simone's warm cunt by seven forty-five, I promise."

Alan laughed with glee. "Hmmm. If you put it that way, it's a bit hard to refuse. Now, that is what I call a liberated and understanding mom!"

As the others talked, Katherine wasted no time stripping off her bikini top and bottom. Then she straddled herself across his lap and impaled herself down with a contented sigh.

She said as she churned her hips to go down deeper, "I told you last night I'm not gonna be jealous, and I mean it. I just need to look at things in a different way. For instance, I want to see you break Heather totally and utterly, like you did with Brenda. If you can turn her into an easily controlled, mindless, starved-for-Alan-cock zombie, then I'm all for you fucking that bitch as much as possible!"

Alan sighed with happiness, as his sister bottomed out on top of him and he could feel his erection go in as far as it could. "I doubt I'll ever be able to turn her into a Brenda, especially since I still don't understand what happened there. But I'll try."

He groaned as his sister's pussy muscles squeezed around his cock. "Geez ... Talk about living like a king!"

Chapter 2

Alan looked around for his standard glass of orange juice, but he didn't see any drink on the tray.

"Um, Mom?"

Susan could anticipate what he was going to say. She sat down on the bed close to his head and pushed her apron off her breasts again. "Don't worry, my loving son. Didn't I tell you we've got it all covered? Just lean forward a bit."

Alan did. The next thing he knew, his mouth was latched to his mother's right breast. He suckled for a few seconds while he thought about how neat it was to drink his own mother's milk with his waffles. The milk tasted sweet and delicious, much better than store-bought milk.

Suddenly he pulled back. "Jesus! Jesus Christ!" He stared up at Susan's bespectacled face in shock and wonder.

"What?" she asked, worried.

"Well, it's just that, dang! You have so much milk today! Yesterday, it was like taking a sip from a dribbling trickle. But today, wow! It's like, it's like some kind of flood of milky mother-y goodness! Dang! It's just like chugging down a glass of milk! What the hell?! And you know what? I think your tits ARE bigger! They look to be absolutely bursting with milk! So soft! So round! So full!" He groped at them as if discovering them for the first time.

Susan blushed and pushed his head back into her chest. "Stop it! Flattery like that will get you everywhere. Why, if you're lucky, I might even let you fuck your very own mommy later. That is, if your sister leaves anything for me."

That comment redirected Alan's attention to Katherine. His eyes drifted to her while his mouth resumed sucking on the other offered nipple.

Katherine was taking her fuck nice and slow, savoring each upward and downward stroke on his long shaft. Sometimes when she bottomed out, she just sat there and gently wiggled while she basked in the sensation of his stiffness filling her up so thoroughly. This was a very considerate thing to do, because it allowed him to suckle and eat his breakfast without jostling the bed.

He winked and gave her a thumbs up.

She winked back and brought one hand to his chest and another to Susan's unoccupied tit.

He paused for some moments and luxuriated in the feeling of his sister's tight hole sliding slowly up and down his morning wood, and at the same time he marveled at how great it felt to suckle at the generous flow of milk which poured out of his mother's nipple.

Susan caressed his face with her hand and asked, "Son, how does it feel to be fucking your sister? Feels good, doesn't it?"

"Mom, it's so good! You have no idea! This must be the kind of high heroin junkies are trying to get. It's like a non-stop pleasure blast. I could ride a slow fuck like this for hours. No, make that friggin' DAYS!"

His face still showed surprise at the milk flow, so Susan explained as she picked up more waffle with the fork, "Last night, Katherine and I were so tired that we both slept through the night. So I've built up about as much of a milk surplus as you've built up a sperm surplus. God, there's nothing more horrible than seeing all that sperm trapped in your cock instead of shooting into the hot twat of a big-titted babe like your sister ... or me ... but thank God this morning we'll be able to take care of your problem and mine. Oh, and I should mention that I've been popping those lactation inducing pills like they're going out of style. I probably overdid it a bit, but look!"

She proudly thrust her chest forward into his face even more than she usually did. "I think the pills must really work! It's been less than a week, and I'm already like this. I can only hope I'll get even bigger and milkier in the weeks to come."

She beamed with joy, and then leaned forward conspiratorially, "You know, to be honest, I measured myself a few minutes ago, and you know what? I AM bigger! A LOT bigger!" Her voice grew with her enthusiasm. "In fact, you no longer have a G-cupped mommy. Say hello to Susan I-cup Plummer!"

Alan disengaged from her nipple and pulled back a bit. I-CUP?! Are you kidding me?! That's not just one bra size bigger, that's TWO! He looked into her eyes to see if she was serious.

Susan, still holding the fork, raised her arms up triumphantly, turning her upper body into a Y-shape. Her apron had more or less fallen off of her completely. She looked radiant, and completely off the top of any beauty scale. What's more, her engorged I-cup boobs stuck out with even less sag than they'd had before.

Alan whistled in appreciation. His whole body was lightly bouncing up and down now, now that Katherine had started to fuck him a bit more enthusiastically. This was one of his favorite sexual positions, since it meant little work on his part and allowed his cock to achieve deep penetration.

Susan, still beside herself with happiness, enthused, "Eat your heart out, Suzanne!" Clearly, the fact that her boobs were now larger than Suzanne's made her very happy. She put her hands under her tits and pushed them up and out, which made them look positively gargantuan in size. Drops of milk continued to leak out of both nipples. Her breasts were so sensitive that it seemed she was on the verge of climaxing merely from holding them up.

But then Susan thought of Katherine and her breast-size jealousy, and she looked to her with concern. So did Alan.

Katherine looked at both of them with a chagrined look on her face. "What?!" She momentarily pretended she couldn't understand why they were looking at her. Then, she conceded, "Yeah, Mom. The whole stupid jealousy thing again." She continued in a flat voice. "Sorry if I can't get wildly enthusiastic, but on the other hand I'm not going to pout. At least I know that I'll grow too when my turn to lactate comes this summer."

She clearly wanted to say more, but she held her tongue from any complaining. She redirected her attention to fucking her brother, and brought both hands to his chest this time. That enabled her to lean forward and support herself against him, yet still leave enough room in front of his face for him to keep eating.

He muttered, "Mom, I'm concerned with you maybe taking too many of those pills."

She replied, "How sweet to say that. But don't worry. Now that I'm lactating, I don't have to do that anymore."

He was inhaling the sweet scent of her recently shampooed hair since her head was practically in his face, when another fork full of food appeared in front of his mouth, a piece of banana this time.

"There you go," Susan said encouragingly, as if she was feeding a baby. "We are in a hurry, so keep eating, big boy. You're not allowed to go until you finish off this plate and drink my milky udders back down to a size E."

He chewed his food and fondled Katherine's tits with both hands, and also moved his hips up and down a bit, which caused delightful sparks of pleasure to fly from his groin to the rest of his body. He mumbled as he finished chewing, "Multitasking. A bit confusing, but I love it ... Mom? Sis? Can I tell you both something?"

"What?" They both said at once.

He looked from one to the other with nearly teary eyes. "I just want to say ... I love you both so much. I don't know how a boy could ask for a better family. So considerate, so caring, so giving, and oh so sexy! You two are the best!"

That brought happy murmurs from the two women.

Susan grabbed one of his hands and brought it back to her chest. Then she brought it up to her mouth and sucked on a couple of his fingers at once. All of a sudden, she took them away, and exclaimed, "Damn! Katherine, you think you're jealous of my new I-cups? I'm more jealous of what you're doing! I want to make my son so happy that I just want to cry, and I don't even have his cock to suck on! It's not fair! What's a loving mother to do?!" She resumed sucking on three of his fingers bunched together as if they were his penis, even though it was a poor substitute for what she really wanted to caress with her tongue and lips.

Katherine cackled with glee, clearly happy to frustrate her mother this once. But it was good-natured feeling, like the pleasure in winning a board game. "Aw, Mom. Shucks! We both should be shaking our fists at Heather and Simone. They're the ones who are going to get his tasty cum this morning!"

Susan looked off dreamily. "Don't remind me. That makes me so fucking HOT! Our studly Tiger, sexually satisfying four big-titted babes even before school starts! Oh! Don't say any more, or I'm liable to simply die of joy! Quick, Son, suck me dry!" She roughly grabbed his head and pulled his mouth back onto one of her nipples.

He happily drank the milk, which seemed in no danger of running out. He let both of his hands caress the round fullness of the breast he was sucking on. The sensations were so good he wanted to whoop for joy. He was surprised to see serious leaks of milk flowing out of whatever nipple he left unattended, making the experience pleasantly sticky.

At the same time, Katherine had stopped her pogo-like bouncing on his cock and was sitting still, experimentally leaning her head into his chest and running her hair all over his skin. But his pleasure only grew, because in addition to the silky hair stimulating his skin everywhere, her pussy was expertly milking his cock with great vigor.

He thought, Milking here, milking there. Milking fucking everywhere! Awesome! This is just total sensory overload! I could get used to this! I totally don't deserve all this attention. I do feel so much love for these two. Now I feel like it's MY heart that's about to burst out of my chest! ... And speaking of chests, those I-cups! Holy hell! God, you're shitting me, this is unreal! When I get home and have some more time, I'm gonna wait till those twin puppies are filled with milk and then give them an excellent titfucking! I wonder if I'll be able to hear the milk sloshing around while I fuck her cleavage and have her tongue flicker at my cockhead. I don't know, but I sure can't wait to find out! DAMN!

Not only that, but what if I had Suzanne get a "size upgrade" too? Whoa.

Heck, why stop there? Everybody should start lactating! God, can you just imagine? Dang, I don't know why, but I suddenly have this vision of all four of them and me walking into a Denny's. They'd all be braless, with their tits sloshing around inside their shirts and big milky wet spots over their nipples. The whole restaurant would come to a complete stop. And then they'd start walking forward, and there would be so much collective tit bouncing underneath those shirts that the entire restaurant would erupt into a complete uproar! Eight tits that are all mine.

OH MY GOD. Brenda! How can I forget Brenda's chest? Ten tits! Imagine BRENDA when she's LACTATING! I don't think she'd be able to stand up without falling over! This is too cool!

He closed his eyes to better focus on all the wonderful feelings of pleasure coursing through his body. He heard simultaneous yelping from Susan and Katherine, and realized both of them were hitting their first orgasms of the day at the same time. His smile grew wider.

Chapter 3

Susan made good on her promise. They made it to school before seven forty.

Alan was amazed at how it happened. One minute, he was still sucking and fondling his mother's nipples and feeling his sister's pussy walls squeeze around his prick, and the next minute the two women had practically carried him to the bathroom and then toweled him off after less than thirty seconds in the shower. Then, in literally less than another minute, his clothes were put on for him, and he was whisked out the front door, still half-wet from his "shower." Everything had been taken care of. They even brought a toothbrush and glass of water in the car for him to brush his teeth.

He sat in the back with Katherine, and she kept his boner "warm" on the ride to school by lightly stroking it as it poked through his fly while he dried his hair, brushed his teeth, and so forth. From the front seat, Susan kept up a banter about how hot and wet all of this was making her.

He was mightily impressed at their efforts to help him, and he vowed to do something nice for both of them soon to show his appreciation. He mulled over different gift ideas as they made their way to school.

Needless to say, he was in a wonderful mood as he ran to the theater room, his erection still throbbing in his shorts. But that mood was punctured as soon as he arrived, because Heather looked absolutely livid.

Alan had told them he would be there at seven-thirty and he was ten minutes late. Had it been anyone but Alan she would have verbally ripped the person's head off at first glance. However, she constrained herself, because she was anxious to have her Bitch Tamer put a Bitch Trainer in her ass, and she realized that chewing out him would be very counterproductive to that all-important goal. She was so eager for it that she hopped from foot to foot as if she had ants in her pants.

As it was, Heather restricted herself to intense seething. If looks could kill, Alan would have died right there, because if there was one thing she hated, it was having to wait. Worse, she had the key to the room she wanted to get into, but she couldn't use it because she couldn't let him know that she had it. At least, not yet.

Simone, on the other hand, was rather amused by the situation and shot Alan a lopsided grin. Normally, she would have been a bit upset at him being late, but that emotion was more than overwhelmed by the enjoyment of watching Heather quietly fume. She almost wished he would have arrived later, just so she could see Heather go completely ballistic. Simone had many years of abuse from Heather to work through.

He caught his breath, looked up and down the hall to see if anyone was looking, then lightly kissed both Heather and Simone on their cheeks.

They were both very surprised at this public display of affection, small though it was. Alan simply never took chances like that. It threw them both off their game a bit, as he'd hoped it would. They were both so surprised that they forgot to say hello.

Then he said to Heather, "My, you're looking good this morning. Nice outfit. You too, Simone. Yummy." He leered at both of them and licked his lips. That was shocking for them yet again. Then he opened the door.

He had good reason to compliment them, because both of them looked great. Actually, that was one reason why Heather was so pissed off. She'd gone to extreme lengths that morning to make herself look good. She'd preened and prettied herself, and fussed over what she would wear, as if she was going to the homecoming ball to be declared Homecoming Queen. In the end, she'd worn her five inch high heels (again), an extremely short brown leather skirt, and a loose and very low cut blue top with no bra underneath. The top practically begged one to peek in and have a very good look around.

She was quite possibly more scandalously dressed than she'd ever dressed at school before, which was saying a lot. She was upset at herself for going to such great lengths just because she was going to meet Alan, and doubly upset that in return he disrespected her by showing up late.

She was also miffed that he dressed no differently today than he always did. It particularly rankled her because it showed his superior position over her - he knew she wanted him so much that he didn't even need to bother to dress nice.

Simone had dressed just as casually as she always did, too. She wore her usual sneakers, blue jeans, and T-shirt. The only difference was that, feeling outdone by Heather, she'd tied a knot in her white T-shirt to expose her very toned and muscular abdominals. She enjoyed being with Alan, but she wasn't in love with him like Heather was, so she saw no need to go to great lengths to look good.

As Alan closed the door, he whistled in appreciation again and said, "Did I miss something? I thought today was Wednesday, not Friday."

Both Heather and Simone were confused by this comment. But Heather, still fuming and looking for a chance to get a dig in about him being late, said in a nasty voice, "Obviously you have a very fucked up sense of time."

Alan just smiled as if he wasn't bothered in the slightest, which was true. He was still on an emotional and erotic high from his time with Susan and Katherine and not much could faze him at the moment. He said in a deliberately bright voice, "Do I? I'm just confused because I'm thinking from the way you're dressed that it must be Grope Naked Heather Day, and you know those only happen on Fridays." He reached forward and down and casually stuck a hand between Heather's thighs. He cupped her pussy as if he owned it.

Heather gasped, both by her recollection of the wonderful Grope Naked Heather Day fantasy he'd spelled out for her last Thursday, and at his impetuous manner of grabbing her crotch like she was nothing but a sexual object. She hated it, but she loved it more. She thrust her pussy into his palm.

But her anger didn't fade easily. She muttered menacingly, "Some nerve you have, just waltzing in here like that."

Before she could say more, Alan pulled the crotch of her underwear aside and thrust two fingers up her pussy. Her pussy had not yet lubricated, because it had happened so fast, but it didn't stay that way for too many seconds.

He yanked her skirt down with one pull using his other hand, and then commented, "Ah. Butt floss. Excellent choice, my bitchslut." Sure enough, she was wearing a microscopically thin pink thong. The only place it showed any significant fabric at all was right over her pussy, or at least it had before he pulled it aside.

Simone had to stifle a laugh as she watched a range of conflicting expressions cross Heather's face. Finally, Heather simply bit her lip. Simone was impressed at the speed with which Alan had taken the situation in hand. She began to wiggle out of her own extremely tight jeans.

Alan, meanwhile, continued to act fast while Heather reeled with confusion. He yanked her blue top up past her boobs and onto her shoulders. Then he roughly fondled a tit with one hand and continued to pump his fingers into her moistening pussy with the other. "Nice. I was just looking at the two of you and thinking how nice it would be to get at the candy underneath these wrappers." He leered at Heather. "You look like a particularly tasty and ripe bitch."

"How dare-" Heather began to bark, but she stopped abruptly because he slapped her hard on the butt. Her micro-miniskirt was in a pile around her feet and the butt floss down her ass crack covered nothing, so the smacking sound of skin on skin reverberated around the room quite loudly.

Then, in a very dexterous move, he took his hand from her richly tanned ass and grabbed her by the ponytail. He yanked her head down while his other hand pressed up against and into her pussy. This forced her to bend over until her body was at a perfect right angle, with her ass sticking high up in the air. It happened so fast that she had no time to defend herself. He didn't even plan to do it, it just happened spontaneously.