6 Times a Day

Alan felt a bit weary at having to be “on” and domineering around Heather all the time. Though it always led to a lot of sensual pleasure, it was also mentally trying to put on a persona that wasn’t really his. He longed to be back home in his mother’s safe and warm arms, sucking on her pendulous breasts like a baby.

He decided to focus on enjoying himself and have Simone do most of the work for a while. One plus about the relationship he’d established with Heather was that he could act a bit selfish and still be in character. So he said, “Simone, are you ready? It’s time for us to begin, and I want you to take charge from the very start. After all, this will be your ‘duty’ from now on.”

“All right,” Simone said. She’d been feeling a bit like a third wheel, even though she’d had the cocksucking to occupy her, and she was glad to take a more active role. She also was secretly relieved to end the cocksucking. It had been going on for so very long that it had become an ordeal for her. But she wasn’t willing to stop, because she was getting a kick out of denying Heather the coveted top half of Alan’s erection. Still, even that had lost its appeal, and she’d just been about to let Heather take over.

She also not-so-secretly longed to lord over Heather for a change, since Heather had pushed her around for so many years, and her new duty would give her a chance to do that.

Alan directed, “Heather, I want you to put your face back in my crotch, but don’t start sucking my cock yet.”

“Awww,” Heather pouted, and then she blushed as she realized she was supposed to hate blowjobs. She had a reputation to maintain, and it was embarrassing how obvious it was that she longed to feel his thickness between her lips.

“You can lick it all you like, though.”

YESSS! All right! Victory! She immediately got busy, slurping all over the cockhead that she’d been denied for many long minutes.

Alan grinned at her obvious enthusiasm. He waited a bit until he could handle her oral attentions. Even though she was focusing on his sweet spot for the most part, he decided he still didn’t need to flex his PC muscle yet. That non-ejaculatory orgasm had done wonders for him.

Then he continued, “Simone, get behind Heather’s butt and stay there. Heather will NOT be turning around to see you or what you’re doing for any reason. Check out the stuff I have in the bag at the bottom of my backpack. You’ll also find a blindfold in there too. I want her blindfolded whenever you’re handling her Bitch Trainers, at least until she earns the right to not have to wear one.”

Simone quickly found the blindfold and tied it over Heather’s eyes. Then she assumed her position behind her friend’s ass, staring right into her pussy. This rocks! Just having a threesome with Alan would be fun enough on a physical level, but the words are soooo entertaining! He says all kinds of stuff to her that I could never say and still live. Literally!

Heather normally would have complained about the blindfold, but she realized complaining would only delay the magical moment when her ass was stuffed, so she kept quiet. As the moments passed, however, she realized the blindfold could actually help her enjoy the upcoming anal sensations to their fullest by allowing her to focus more of her attention there.

The “stuff” in the bag was the collection of dildos Alan had brought from home. In recent days, the dildo collection had somehow grown by leaps and bounds. It seemed as if all of Alan’s family four had been developing private collections of their own in recent weeks (except for Suzanne, who’d had a sizable collection dating back many years already), but they had now all reached a point of comfortable familiarity where they’d started to share all their sex toys freely. So most of them were kept in the underwear cabinet by the front door. He had tried to grab the biggest dildos he could find, but there were surprisingly few big ones (Mr. Excitement tended to stay in Katherine’s room). Apparently, none of his women at home were “size queens” and they preferred dildos the size of his penis, or just a little bit bigger.

He hoped that the selection would prove suitable for Heather’s needs, at least until he had a chance to buy some more.

He watched as Simone pulled out one dildo and then another, and carefully examined each one. He suddenly leaned over and sprawled himself forward, resting his entire body on top of Heather’s back as if she was a table. With his head directly over Heather’s ass and his hands grabbing ahold of her ass cheeks to steady himself, he leaned forward still further, indicating he wanted to whisper something in Simone’s ear.

So Simone leaned forward too, and Alan whispered very quietly to her so Heather couldn’t hear, “I’m thinking, we can’t let on just how big the dildos are, or it’ll ruin all the mystery for her. So never say ‘What do you think about this ten-inch one?’ or anything like that. But it’s good to hype them in a general way to get her excited and imagining that they’re bigger than they really are so as to keep her guessing.”

“Gotcha,” Simone whispered back, deviously smiling at his cleverness.

Alan remained sprawled over Heather, and Heather was surprisingly quiet about it (all of her attention was focused on what would soon be entering her, and she didn’t want to spoil or delay the moment by complaining). He continued to lean out over her ass so he could have a view of all the anal action from mere inches away.

With deliberate slowness, he pulled her muscular buttocks open to reveal her cleanly shaven, lubricated asshole. He could see just how excited Heather was by the way her anus puckered and pulsed in anticipation of what was coming.

Simone finally picked out a dildo, the very smallest one that Alan had brought. In fact, it looked to be an anal dildo that he had grabbed by accident in his haste. Simone winked at him, and said for Heather’s benefit, “Okay, I’ve got a big one for you. Are you ready, girlfriend?”

Heather steeled herself as if she was about to experience something as intense as giving birth. She grunted, “Yes!”

Simone slipped the small anal dildo into Heather’s asshole. Like most anal dildos, it was wide on one end and tapered down to a point on the other. It wasn’t meant to go in all the way, but instead it could be poked in and out like a penis. But Simone pushed it in as far as it could go, and then left it there.

Heather grunted like Simone had shoved something truly massive up her ass. But then there was a pause.

Alan wished he could have seen her face at that moment, because he knew her expression would be a priceless “Kodak Moment.”

Then Heather exploded. “What the FUCK?! You call THAT a dildo?! Toothpicks are bigger than that sorry ass thing! Is this some kind of cruel joke?!”

Alan and Simone cackled gleefully.

Then Alan said, “Sorry. We’re just kidding around. Simone, please give her a real dildo.”

Simone pulled that one out and quickly replaced it with something much more sizable.

Alan wasn’t a good guesser at sizes, but he figured the dildo was a tad longer and thicker than his eight-inch penis.

Heather’s bitchy grumblings dissolved into sexy moans as this new dildo was pushed into her. Although her ass had been filled by Alan’s dick rather frequently lately, she had a strong and tight sphincter and her entrance hadn’t loosened. So it was a struggle to get it in, even with lots of lubrication.

But they persevered and finally all but the flanged base of the dildo disappeared inside her.

She exulted, Payoff! I spent a fucking half hour at least sucking on his balls until I thought I couldn’t move another muscle. But it was soooo worth it for this! It may not be his cock, but it’s very nearly as good! Plus, he’s letting me lick all of his cock now, and that’s fuckin’ glorious. Every inch of this cock is MINE! She lapped on his sweet spot happily, and then added, See? Morgan women always get what they want in the end! She chuckled to herself at her accidental double entendre.

Alan made a mental note that he would need to buy special anal dildos with strings so they could be inserted all the way and still be easily pulled out.

But once Simone and Alan got it in, Heather complained to both of them, “You call that big, Sir? I’ve had bigger. I thought you were going to put in something BIG! Fill me up with something serious, Sir!” By speaking so impetuously, her use of “Sir” turned into a mockery, and a challenge to Alan’s authority.

She went on, “And what’s with that base that won’t let me take it ALL?! I can’t have that sticking out of me and ruining the curves of my perfect ass when I flaunt it while wearing my tightest shorts and my butt floss! Here! Take this reject back, Sir!”

Then she grunted oddly, and right before Alan’s and Simone’s astonished eyes she pushed the offending dildo out of her asshole, hands free, with a speed they hardly thought possible.

Alan knew from firsthand experience that Heather had some pretty powerful internal muscles, but he hadn’t realized just how strong she was inside. It had taken actual work on Simone’s part to get that big dildo into her, and now Heather was pushing it out as though it were no more than a roll of quarters, using only her rectal strength. .𝘤𝑜𝑚

Alan and Simone watched the dildo clatter onto the floor following its hasty exit from Heather’s rear. The two of them then looked at each other with wonder, as if both were saying, “I didn’t know a person could do that!” They were more than a little impressed with Heather’s ass strength, but neither said anything out loud for fear of further inflating Heather’s already massive ego.

Alan was especially wowed, as he recalled how those same anal muscles had tightly squeezed his dick in the past. Even as Heather resumed licking his sweet spot, he got an extra erotic thrill contemplating his dick discovering more of her anal talents in the future.

Alan and Simone returned their attention to the rest of the dildo collection with a sense of dismay. They both realized that it was doubtful they had anything bigger.

But Alan nodded his head in such a way as to non-verbally say to Simone, “What the heck, let’s try another one and see if she likes that any better.”

After just a brief silence, Heather complained, “Any day now. Sir.” She wiggled her hips petulantly, and made another hickey-like sucking attempt on the side of his cock.

Alan spoke to the still annoyed Heather. “We’re working on it. Geez! In the meantime, make yourself useful and suck my dick back to full size and keep your lips around it. At the very least, that’ll shut your bitchy mouth for a while.” He was still on her back and her face was practically in his crotch. All he had to do was hold his cock out and feed it towards her mouth.

“I don’t know why I put up with you jokers,” Heather mumbled. “And I highly resent all this cocksucking.” But she couldn’t disguise her eagerness to finally be given permission to not just lick, but suck, to her heart’s content. She immediately engulfed his cockhead and got busy bobbing on it with gusto.

The truth was, even though she was complaining, the dildo sizing was great fun for her, and even downright exciting. Plus, she tried to convince herself that she hated blowjobs, which was generally true since they weren’t all about her pleasure, but with Alan it was different. His cock wasn’t just a means to give her pleasure anymore, she was falling in love with it just as she was falling in love with Alan. When she had it throbbing with pleasure that made her feel very good, even if she wasn’t feeling pleasure in return. She also loved the challenge of getting him to cum, and the reward she’d get when she succeeded. Just thinking about his hot seed spurting into the back of her mouth nearly made her climax.

Alan shook his head with amusement as he felt all of the different tricks she was trying to do with her lips, tongue, and fingers, seemingly all at once. And she says she doesn’t like blowjobs. Yeah, right! Can’t she even hear how loudly she’s slurping? It’s true that she’s not Mom good yet, but she’s getting there.

Rather than rebuke Heather’s complaints and surly attitude directly, Alan decided to take a more subtle but satisfying approach. He watched while Simone held up the dripping dildo that had just been so unceremoniously ejected from Heather’s ass, and watched as she held other dildos up to it and compared sizes until she found one that was slightly bigger but double ended.

Alan winked at Simone, and then said, “Oh my God! Not that one! Simone, that’s a gag gift. A dildo like that can’t actually fit inside a person for real, can it?”

Simone looked at the dildo, perhaps ten inches long, if that, and wondered what the heck Alan was going on about. But then she realized his intentions. Playing along, she said, “I don’t know, but I think it’s time we found out. After all, our favorite bitch queen says she simply can’t get one big enough to satisfy her.” She said with a naughty smile, “She must be as wide and deep as a cavern in there.”

Heather ignored the jibe and kept cocksucking. She was intent on getting a big hot load on her tonsils. She didn’t really believe Alan could hold out for ever, and she figured that even he would have to give up his cum before long, if she kept at it with all her might.

In fact, he still had a long way to go, thanks again to that non-ejaculatory orgasm. He still wasn’t even resorting to his PC muscle moves yet. He gleefully continued with his protests. “But Simone. Be reasonable! That thing is HUGE! It’s like a yuletide log. You could seriously cause some permanent internal injury with it!”

“Hmmm. You’re right. But if we gently push in just the first fifteen or so inches of it-”

Heather instantly popped Alan’s erection out of her mouth. She practically screamed, “Fifteen inches?! I can’t take that much! No way! Please!”

Simone winked at Alan. “Hmmm, she may be right. Why don’t we get her used to it by stretching her out with a Coke can first?”

“Arrgh!” Heather appeared on the verge of tears. “Please no! Have mercy! Please, I’ll do anything; just don’t put that monster in me! Please! Sir!” She was practically vibrating with fright now.

Alan laughed. “Ah. So now you remember to call me ‘sir.’ I think in this kind of situation you should call Simone ‘ma’am’ as well.”

“Yes, Sir! Yes, ma’am! I’ll be good!” Interestingly, in her mind, the “sir” was capitalized but the “ma’am” wasn’t. Despite her protestations of faithfulness, she was wriggling her hips, trying to dislodge Alan’s hands from holding her ass crack open. She was torn between wanting to consume his cockhead again and worrying that she’d need to speak some more.

Simone burst into laughter; she couldn’t help it. She was greatly amused by Heather’s change of attitude, and the new title of “ma’am”.

“What?” Heather asked, suspicious about all the laughter. Heather’s hips stopped moving and Alan very deliberately pried her taut butt cheeks open again.

Instead of answering, Simone pushed the slightly bigger dildo into Heather’s unsuspecting asshole.

Alan took advantage of this. Putting his hand on Heather’s further down his shaft, he maneuvered his cockhead back into Heather’s suddenly wide open mouth. That served to shut her up again, at least for a while.

Heather thought as she unthinkingly resumed bobbing on his thickness, I really shouldn’t be putting up with this shit. They’re mocking me. ME! I OWN this school! I’m going to tell them off in no uncertain terms, just as soon as I can get Alan to fill my mouth with his sweet cum. Why is his cock so God damned yummy? And I’m not just talking about his cum; just sucking on his thick meat tastes good! Why does the fucking fucker have to take so fucking long to cum?! He seriously annoys me with his God damned big and talented cock. He thinks he’s so great. Grrr! I’ll show him who’s great by making him blow his load straight down my throat!

She closed her eyes and tried to devote all her attention to licking and sucking her favorite cock, but it became more and more difficult to think or act as her hungry ass was slowly filled. She gasped and gagged, as it was suddenly hard for her to breathe, but she didn’t pull her lips off despite everything.