6 Times a Day

Alan reached down and grasped Heather’s limp hands where they hung at her sides, drawing them up with his own as he enfolded her shoulders in his arms again. He gently pinched and played with her rock-hard nipples while she just shuddered in response.

He stated as fact, “You’re going to be filled up all day long. Your asshole, of course. Maybe your cunt too, if I feel like it. Maybe if you’re really bad I’ll even have to run a strap around your head and keep a big plastic cock firmly planted in your mouth all day long as well. I wonder what your friends and teachers would think of that?”

“You wouldn’t!” She loved his tough talk. She felt as if she was a kind of soft goo, to be molded and shaped by his strong hands. She loved the way he’d picked her entire body up, and she still thrilled from that.

“Maybe not. Maybe not at first. Of course, we’ll have to concentrate on your ass.” He recalled the way Glory strutted around during lunch, flaunting her ass when she expertly mimicked Heather’s walking style. He said, “You really love to flaunt your ass when you walk, don’t you?”

She answered breathlessly, “Yes!” She felt like it was impossible to lie to him when he had her so thoroughly filled with thick inches of fuckmeat.

“Especially lately, you’ve really got quite a saucy walk. Well, now your ass is mine. Now you’re going to dress just like I want you to dress. You’re gonna walk like I want you to walk. You’re my Barbie Doll, and I’m taking total control over what you wear and what you don’t. What do you think of that?”

She just gasped at his audacity, and wiggled her ass around his stiffness more than before. Yes! Oh God! Alan totally controls me! I’m his BITCH!

“No more skirts or dresses for you. No. You’re only going to wear extremely thin and tight shorts and pants. Clothes that you have to paint on. Clothes that are so tight you’ll need help to get them on and off.”

She was eating this up eagerly, and merely asked for clarification, “Blue jeans?” She owned some very tight blue jeans.

He stirred his erection around inside her ass while considering her request. “No. Too thick. Everyone needs to be able to see your panty lines as clear as day. Except you won’t have any panty lines, because you won’t be wearing panties. Not normal panties, anyways. From now on, you’ll only wear dental floss. You’re going to wear strings up your ass crack so thin that they’ll make dental floss look thick in comparison. Butt floss, we’ll call it. I want you to wear tight thongs that cover up just enough of your cunt so you don’t get kicked out of school, but leave absolutely nothing to the imagination in the back. Your tight shorts or pants will have to cleave deeply between your butt cheeks and ride high and tight in the crotch, leaving your ass cheeks completely exposed to everyone from now on. You need clothes that say, ‘I love my ass and I need to keep it well fucked!'”

She let out a throaty growl that showed how much the idea turned her on. “Butt floss!” I’m his Barbie Doll! Shit, I’m gonna cum so hard that I’m gonna DIE!

He had paused in his fucking for a bit to get that wordy idea out of his mouth, but now he picked up the pace again. He moved steadily in and out of her anal channel.

She moaned, “Yes! Yes! More! More! More!” She referred to both his words and his thrusting.

He went on, “Luckily, you’ve got a very strong ass. It’s good that you’re a muscular cheerleader, because you’re going to need that strength. I want you to work your butt, and constantly exercise it. I know you already have a fine ass, but I want your glutes to be stronger, firmer, better toned, more muscular, and better defined. I want your ass to flaunt that you’re an anal addict second to none. You know how some homeless people have signs that read ‘Will Work for Food?’ Well, I want your ass to say to me from across the room, ‘Will Crush Cocks For Cum.'”

She was in heaven. “Harder! More! Hurry!”

He huffed between labored breaths and deep thrusts, “And when I say, ‘for me,’ that’s just what I mean! I know you’re an insatiable slut, but now you’re MY insatiable slut! Enjoy playing with the football players this weekend, because it’ll be the last time you’ll have sexual freedom. I can’t possibly keep a slutty whore like you completely satisfied. I realize that. But from now on, I’M” – he gave her a particularly deep thrust with that word – “going to tell YOU,” – that was punctuated by another huge push – “just who you can FUCK” – another thrust – “and WHEN … and WHERE!”

She couldn’t lie to him, not with the way he was treating her and making her feel so good. She confessed, “I can’t! I’m sorry, I can’t, Alan! I have to be honest. I know what I said before, about having sex with just you, Simone, and the other cheerleaders. But I don’t know if I can do it for long. I need cocks! Even though I love yours the best!” .𝘤𝑜𝑚

She blushed as she realized what she was admitting, and qualified that. “I love your cock the most, I mean. But you’re so busy with all your other women. I need to get fucked daily, preferably with real cocks. Playing with girls has been tiding me over, but that can’t last for long. I’m sorry, but that’s the truth!”

He stopped thrusting momentarily, because he had to thrash this issue out. He waited until his breath caught up to him. Then he said, “Don’t worry. I’ll give you cocks.”

He thought of Sean and hoped Sean would prove himself worthy. “Not many, true, but then it’s a question of quality versus quantity. You’ve tried quantity, and that doesn’t work. I’m halfway tempted to allow any of those football players this weekend to fuck your ass. I’ll bet you none of them would even want to try. They’re all squeamish about it, thinking it’s gay.”

He thought to himself, In fact, they’re just like I used to be. What a painful reminder of how immature I was. God, so much has changed since then. Hell, it wasn’t long ago when I wouldn’t have been able to say “Boo” to Heather. And now look at me! I’m boning and owning her ass! Heh!

He pulled back a bit and pounded into her once, hard, just to hear her grunt as he knocked the wind out of her lungs. He held himself deep as she gasped for air, while her asshole clenched spasmodically around him.

Leaning in closer to her, he spoke directly into her ear. “No, I take that back. Knowing you, you’ll talk or force someone into it. But see how good it is. Anyone spineless enough to get pushed around by you is not going to give you the kind of assfucking that you really crave. Only I know what you need – me and the guys I’ll choose and train for you. And of course women. We’re gonna have to teach some of them how to keep your favorite hole happy with a nice, big strap-on. Now, you can either stick with my plan and have your ass constantly humming with happiness, or you can sleep around far and wide and have a lot of clumsy oaf athletes unload into your pussy and pull out before you get a chance to cum.”

He teasingly flicked the outside of her ear with his tongue, making her shiver and whimper with desire. He whispered to her while sexily blowing into her ear, “It’s your choice.”

She was struck by how much sense that all made. What he said seemed like a no-brainer. Her asshole obviously loved the idea, and seemed to throb and squeeze even more than before. Alan’s cock! That’s the one I need. Screw all those other guys! I don’t even want one of those clumsy oafs to sully my ass with their pathetic dicks! Alan is the only one who understands me, and gives me exactly what I want!

She excitedly and repeatedly clenched her anal muscles around his hot boner.

That felt so good that he worried he would cum at a most inopportune time. He drew back before continuing, pulling out until he had only an inch or so still inside her.

She felt the emptiness within her and wanted him to fill her up again so badly that she focused her attention even more on what he was saying. At the same time she wriggled her hips to express her increasingly great need.

He said, “But here’s the key point. If you go sleeping around with just anybody, you’re a sexual disease just waiting to happen. I hope to God that you don’t have something already and that I won’t catch it if you do. But assuming you’re still clean, you’ll have to reduce yourself to just a select few or I’m not going to fuck you ever again. Period. And they’ll have to keep their partners in a closed circle for the whole thing to stay clean. The cheerleaders might be the right group, if they’ll all agree to the same idea.”

She thought about this. It made a lot of sense. “What about Simone? I can’t go without Simone! I was telling you earlier that I have sex with her pretty much every day.” Her anus clutched desperately around his cockhead as she practically begged, communicating her fear to him that she might be denied her best friend and lover.

He answered, “Same deal. I know she’s another complete slut, but if she limits her partners to an approved group and you trust her with that, then maybe. Maybe she needs some training too. But first I have to train you. I haven’t finished explaining what’s going to happen to you.”

She thought, I can’t go without Simone! I just can’t! I couldn’t imagine life without her. But dammit, I’m gonna make this work so I have Alan AND Simone! I don’t care if I have to burn the whole fucking school down to do it. I’m Heather Morgan, and I always get my way!

She thought back to how they’d been earlier, with him standing fully clothed and her naked on her knees and stroking and licking his erection. Even now, she felt tremendous embarrassment. Well, maybe not always… lately… Damn. How did I let that happen?!

He resumed his slow, rhythmic thrusting, as he wanted her properly breathless and mewling for his explanation. “First, remember my butt floss idea. Oh yeah. And high heels. You’re going to be the only girl in this school to walk around in really high heels, five-inch heels at least. They’ll be essential to hoisting your ass up high and keeping it there for the proper ‘knock me down and fuck me’ look. I want you, and everyone around you, to be fully aware of your ass at all times. I want classes to come to a complete and sudden stunned halt whenever you get up and swish your slutty ass around.”

“God!” she panted. She pictured herself strutting up and down the school halls in extremely high “fuck me” pumps, wearing a scandalously short miniskirt with nothing but “butt floss” underneath. She loved all the people gawking at her, but she knew she’d be dressing that way just for Alan. Ultimately, nothing mattered but what he thought. She could feel the mother of all orgasms coming on.

He continued in a commanding tone, “Remember the butt floss idea. Your butt cheeks are going to be trapped inside your sprayed on short shorts, rolling around inside your painfully stretched, tighter than tight clothes, fighting each other to escape! Your butt floss thong will be pulled up into your crotch so tight that it’ll rub your ass crack and pussy lips maddeningly whenever you walk around. I want you to be completely unable to walk any long distance without cumming in your shorts from all the incessant rubbing. Running should be completely out of the question. If you were foolish enough to try and run somewhere, you’d have to fall on the ground, rip open your paper-thin shorts, pull aside your butt floss, and shout to anyone and everyone, ‘My ass is on fire! Someone come here and douse it with your cum to put out the flames!”

“Alan! Stop! No more! My ass IS on fire! I need it now! The way you’re teasing me with your words and your painfully slow fucking is too much! You’re destroying me! Fill me with your cum! Your magnificent cum! Hurry! Please!”

He had gotten so carried away with his description that his thrusts had nearly completely stopped. He resumed his in and out pistoning, but he continued with his description. “But that’s not all. Don’t forget the anal vibrator. Only we’re not going to call it a vibrator. We’re gonna call it a Bitch Trainer, complete with capital letters.”

“YES! Bitch Trainers!” She growled in triumph. “Train this bitch right now!”

She felt an itchy hot heat of need take root and bloom outwards from within her asshole, even as Alan continued to fuck her there. The idea of training carried with it the promise of many assfucks to come. She imagined that once her ass was fully trained, and it was a perfect vessel for his cock, he’d fuck her there every single day. I’m gonna be his ultimate cum dump! The insides of my ass will be constantly coated with his sweet cream!

Just the thought of that nearly made her pass out.

He had to pause again to catch his breath. But then he said with renewed vigor, “I will! But an ass like yours needs constant control and supervision! I’m going to have to look into which Bitch Trainers are best for you, but I’m envisioning one that’ll make a small bulge so your butt will be that much more eye-catching. If you’re lax in your self-discipline and let your backside backslide on keeping it in, everyone will look at you and whisper to each other, ‘Hey, what’s that big round thing falling out of Heather’s ass crack?”

He gave her ass a hard swat to enforce the idea of “discipline” in her.

“WAAOOOWWWEEEEIIIAAEE!” She let out an ear-piercing scream like that of a cat being dropped onto hot coals. Shivers of excitement ran up and down her spine and her body trembled all over. Her anus and insides spastically clenched and throbbed around his penis in ecstatic response as well.

She couldn’t understand why a mere smack set her off so much. What the fuck is up with THAT?! After all, I’m the real dominant one here and I’m just letting him play around with a temporary role reversal, right? I want to train my ass to be his ultimate cum dump because it makes ME happy! But she was too far gone to give it much thought.

He was surprised at the intensity of her reaction, and he made a mental note to spank her more in the future. He also noticed that the physical sensation upon impact was quite different from when he’d spanked Susan while fucking her ass. There was a louder sound, like the crack of a whip, and less give. He figured that Heather’s stronger, harder buttocks and her firmer, tighter grip on his boner explained the difference, even though his mother had an extremely fit ass as well.

Reaching up, he grabbed hold of Heather’s blonde ponytail and pulled her head back, forcing her to arch her back and offer her ass to him at a better angle.

He hotly whispered into her ear, “You’ll be parading around school with pants so tight and thin that you might as well be naked. Everyone will be able to see the bump of your clitoris, and they’ll probably rub it too. And your butt will be so full of plastic cock that it’ll seem like I’m clinging to you like a monkey on your back all day, constantly riding your ass and fucking you wherever you go! Everyone who sees you will drool! Their hands will fly to their crotches, both boys AND girls! Even though your body will now be off limits to all but a select few that I choose, no one will be able to resist reaching out and groping your perfect butt as you shamelessly parade it around.”

He kneaded her ass cheeks so she could feel as well as hear what he was saying while his dick continued to pump her. “Your ass will be handed off from one groper to the next. Dozens of people – teachers and students, boys and girls – will feel you up before you can make it from one end of the hall to the other. You’ll just have to hope that when you’re constantly fondled, not too many fingers will find their way between your butt cheeks and probe their way on up into your asshole, because then they’ll find out just how full you already are!”

She was panting hard, but she somehow managed to say, “Oh God, that sounds so hot! When can we start? Tomorrow! Oh no! I wish I, I could start tomorrow… OH! But I, I’ve got to… Have to wear my regu- my cheer- my cheerleader uniform all day… For, for, for the GAME! UGH!” She pushed back against his hips and ground her ass down onto the root of his penis in frustration. “I already HATE the idea of wearing skirts!”