6 Times a Day

Once the procedure of inserting the dildo completely past Heather’s spastically clenching anus came to an end, Alan asked her, “How does that feel?”

Heather tested her ass. She certainly felt quite full when she flexed “down there.” She somehow knew that she could take something even bigger, since she didn’t feel “filled to the gills” like she’d expected to, and Heather being Heather, she wanted to go to the maximum right away. But after the talk about the “yuletide log dildo,” she felt a bit chastened and didn’t dare ask for something else for fear they’d go back to that one again. As her rectal muscles rippled up and down and all around the dildo in her ass, she found herself reflexively sucking on his erection for reassurance, as if it was some kind of baby pacifier, while her butt got acquainted with the new sensations it was experiencing. She was positively grateful for the blindfold now, as she could revel in her anal sensations more than ever before.

She wanted to explain that she really liked how the dildo felt, but she didn’t want to pull Alan’s boner out of her mouth to speak. She tried to say “Mmmm!” as encouragingly as she could, but her meaning wasn’t clear.

Simone stashed the dildo collection out of sight back in Alan’s backpack and then came around to look into Heather’s blindfolded face. “How’s that?” she asked. When Heather again failed to respond beyond more mysterious moaning sounds, Simone took off the blindfold to see if Heather was all right. She promptly burst out into hearty laughter again.

“What?” asked Alan.

Simone replied, “It’s just that you should see her face. Tears are actually leaking from her eyes. Her eyes are so wide open that they seem stuck that way. It’s like she’s imitating that kid from the ‘Home Alone’ movies. I’ll bet if she wasn’t sucking on your dick, her mouth would make a perfect ‘O’ shape. Actually, it is making a perfect ‘O’ shape; it’s just that your cock is sliding in and out of the ‘O’. I’m thoroughly amused by the thought of her going around all day with that stunned look on her face.”

Alan chuckled. “I’d like to see that, too. But I have to admit that being draped over her like this has advantages of its own.” As if proving his point, he fondled Heather’s flexing and muscular ass as he said this, and luxuriated in the sensations her sliding lips were giving his hard-on. He manhandled and kneaded her strong buttocks for a little bit before gripping her ass like a handle and pulling her entire body back into his crotch.

Heather gagged, coughed and spluttered when Alan’s cock went too deep and attempted to penetrate her throat, but then his dick just as quickly pulled back and she reestablished her earlier cocksucking rhythm. This is so humiliating. He’s using my mouth as a cum dump and playing with my ass like a toy, and I’m loving it! I should fight back. I should at least bite down a bit to show him who the boss is around here. I’M the boss, dammit! I’m the boss!

She repeated “I’m the boss” several more times while Alan roughly fucked her mouth. She continued to resentfully contemplate biting his cock a little bit, but she didn’t so much as put her teeth to it. His erection was remarkably sticky with pre-cum by now, which only redoubled her resolve to swallow a full load. She was getting tired from all the licking and sucking, but she didn’t care.

Simone was also idly stroking Alan’s back, but for the moment she was much more interested in observing Heather’s reaction to the large intruder her ass had swallowed up whole than getting fully involved.

Alan had been slowly reaching a climax, thanks to Heather’s unusually enthusiastic cocksucking, so he asked Simone, glancing significantly down at his own groin, “Can you take it out?”

Simone tried to pull Alan’s erection away from Heather’s nursing lips, but she was quite horny too, and began pumping his sticky thickness with both hands instead.

Alan laughed with glee. He thought, Now, this is the life! Two of the foxiest girls in school will do whatever I want. They can’t get enough of my cock! This is just like being at home with Mom and Sis. I can’t believe I’m gonna have to go from this to my boring first-period class soon. Ugh. Physics! Maybe taking a hands-on role in Heather’s Bitch Trainer insertions wouldn’t be such a bad thing… Nah. I can’t forget Mom and Sis and our morning fun.

Thoughts of Susan and Katherine made his boner lurch, and thanks to Simone’s double-pumping around the base and Heather’s nibbling on the cockhead, he very nearly lost control. He remembered to resume his PC muscle squeezing, and that helped.

Snapping from his daydream, he chided Simone in a friendly way, “Hey, stop it already! I’m trying to calm down for a minute. Let’s hear what Heather has to say.”

Simone reluctantly let go of Alan’s member, but she was unable to pull it away from Heather’s sucking ruby red lips. 𝗼𝘃𝗹.𝗼𝐫𝗴

Heather was silent for a while, but after an impatient Simone prodded her with another “Well?” the blonde bombshell finally pulled her mouth away from Alan’s throbbing erection and replied in a rather awed voice, “I feel … full. To be honest, I kind of lied. I’ve never had anything like this in me before. Just Alan’s thick and tasty penis and… some rather small anal dildos like the very first one you jokingly put in me. This, on the other hand, feels, well… full! It’s like, well, I can’t explain it. I know it sounds stupid, but it almost feels like my ass is like… I dunno… pregnant, or something… like I’m about to give birth… as weird as that sounds. I can’t really describe it. There’s this THING in there. This tremendously large thing inside me… that feels, really good! But I feel like I need to go to the bathroom. I mean, I can take this for a while, but I can’t possibly imagine having this thing in me for hours and hours! There’s no way!”

Alan stood up and then pulled Heather to her feet. She wobbled dangerously, but he steadied her until she was standing on her own. He was relieved to have his dick untended for a while, as he’d been extremely close to losing a big load and it would undercut his authority to shoot it into the bitchy cheerleader’s mouth.

He let everyone have a much needed rest for a bit. But in no nonsense tones, he firmly told Heather, “Well, imagine it. You will have your Bitch Trainer in you all day, unless you cry uncle and give up. Then Simone will help you, but that will be the end of it.” He tweaked both of Heather’s nipples to renewed hardness, nearly making her knees collapse out from under her, before continuing on in a softer, more condescending, yet confident voice. “But I don’t take you to be a loser and a quitter. Am I wrong about that?”

“No!” she said confidently.

He was once again using the simple psychological trick of playing to her competitive nature. Looking deeply into her wide open “deer in the headlights” eyes and flushed face, he continued, “We’ve seen that keeping you filled with my dick changes your attitude, and I can already see this dildo is doing the same. Your voice has already changed, becoming softer, mellower and much more pleasant sounding. Your angry and arrogant tone is gone, just like that.”

He snapped his fingers to make his point, making a blissed out Heather blink in surprise. “Needless to say, I’m pleased so far, but the big test is, will the change last all day, or will you grow immune to it and go back to your bitchy old self? That’s the key test. If the latter happens, then I’m afraid I won’t be able to help you much, after all.”

Heather didn’t reply. Her eyes had narrowed with determination when he hinted at her being a loser and a quitter, but her facial expression quickly returned to one of wide-eyed wonder.

Alan chuckled again at Simone’s vision of Heather looking like that all day long.

But Simone was still chuckling too, and seemed even more amused.

So he asked the dark-skinned beauty, “What?”

Simone answered, “Well, for starters, you can see that she’s STILL doing the ‘Home Alone’ look.” She made a mocking impersonation of Heather’s face, and referencing an old Saturday Night Live act, cried out in a high-pitched voice, “Oh no! Mr. Bill!” She laughed at her own joke. She was having a grand old time.

Ignoring Heather’s evil eye, Simone went on, “And for another, Heather, honey, you do know we were just yanking your chain with that whole ‘yuletide log dildo’ thing, don’t you? Oh, that was so much fun! You were about to pee in your pants you were so scared shitless! Not that Alan ever allows you to wear pants or any other clothes! Ha!” She laughed even more uproariously.

Heather burned with anger and embarrassment. She didn’t take being the butt of a joke well at all. “Bastards! I’ll get you back!” She muttered this just loud enough for them to hear.

She longed to have Alan’s cock back in her mouth, both to bite down on it enough to make him hurt and to suck it till he filled her mouth to overflowing with cum. In fact, she loved the act of sucking and licking, even without the cummy reward.

“Now, now,” Simone corrected. “‘Bastards, ma’am’ and ‘Bastards, sir.’ You have to learn how to address your superiors!” She thought that hilarious, and laughed even more at Heather’s expense.

Alan could see there were ways one could push Heather and ways one should not, and this fell into the latter category. Plus, there were things he could get away with saying that Simone could not. He said diplomatically, “Heather, please forgive Simone, she’s not used to this role reversal. As for the dildo trickery, sure we were having a bit of fun, but it also served a purpose. I’m worried that you have ‘size queen’ tendencies and I want to warn you off from putting in the really big stuff.”

Rather than reply, Heather kept looking away and mumbled something under her breath. While her words couldn’t be heard, her bitter tone made their meaning clear enough.

The lack of time before school started was very much on Alan’s mind, so he decided not to make an issue out of Heather’s surliness. He looked at the clock on the wall again, as he’d been doing periodically all along. He nodded at Simone, and then at her bag.

Simone took over. “Heather, Alan was thinking that you’re going to be walking funny today and people are going to wonder why. We talked about some of this stuff on the phone yesterday. So I’ve taken the liberty of sneaking these out of your house when I stopped by to pick you up this morning.”

She held up a pair of five-inch heels. Heather wore two-inch and three-inch heels all the time, but she had been annoyed at how difficult it was to walk in five-inch heels and thus avoided them. Although she’d bought the pair Simone was now holding up, they were still among her collection only because she’d never gotten around to getting rid of them.

Simone casually said, “Your ‘cruel shoes.’ I know you’re not keen on them, but Alan has a point that they’ll provide an obvious excuse for why you’re walking so funny.”

“Okay. Fine,” Heather grumbled, grabbing the shoes from Simone’s hands. She was still pissed off at both of them. But at the same time, she was thinking about the silver lining: wearing the very high heels would firm up her legs and ass, making them look more tantalizing for Alan.

“‘Okay. Fine, ma’am,'” Simone corrected firmly.

“Ma’am.” Heather grumbled some more, but Alan was right: her voice no longer had its usual taunting, surly edge. Now she just sounded resigned; defeated by her own lust.

Alan spoke. “Heather, like I was saying earlier, it’s all about rewards and punishments. Sadly, you’re not yet worthy of taking my cum. But Simone is. Simone, would you be up for a quick fuck? I’ve been having a load build up in me all morning and I could really use some release before school starts.”

“Why certainly, since you asked so nicely.” Simone knew that she was unlikely to get off with her own climax in the few minutes they had left to fuck, but she was glad to do it, if for no other reason than the fact it would be a fucking denied to Heather. She still had a lot of resentment towards Heather built up that she needed to work off, and this was just a small down payment on that.

So Alan sat back down on the couch he’d been sitting on at the first part of their session and rolled a condom onto his erection.

As he did that, Heather looked on with dismay. “You can’t be serious. After what I did with your balls for, like, five fuckin’ hours, this is my reward?!”

He replied, “It’s not just about you. You got rewarded with your dildo. Meanwhile, what did Simone get from all of her cocksucking? I’ll bet she hasn’t even cum yet.”

“I haven’t,” Simone said.

“Well, let’s fix that then,” he replied.

Heather huffed, and stormed off. Then, realizing she didn’t really have anywhere to storm off to without leaving the room, she decided to pretend to not care instead. She also was wobbling dangerously walking in her heels, and realized she needed to do something about that.

Simone sat down on Alan, impaling her hot and wet pussy on his turgid pole. She let out a contented sigh as she lowered herself all the way down.

Alan was a bit sexed out from all the morning’s events and in no mood for a big, energetic performance, but Simone understood that, so she did most of the bouncing while he just sat there and enjoyed the sensations while letting his hands wander all over her.

Heather, meanwhile, was experimenting with walking around. Between the dildo up her ass and the high heels, it was quite an effort for her to simply walk from one spot to another. For one thing, her new posture tightened up her calves and buttocks, even more so than usual, which put unexpectedly sexy pressures on the Bitch Trainer she held inside her tightly clenched anus as her legs moved and flexed. As a result, she inadvertently put on a very sexy show right in front of Alan.

Watching Heather in the buff strut her stuff was an excellent bonus arousal on top of the very pleasurable fucking he was getting. Dang! Heather naked in high heels is so fucking smokin’! I’m gonna cum already if I don’t watch out. I need to make this good for Simone, even if she is doing more off the work.

Heather, who specialized in cockteasing men with “accidental” displays, was, for once, truly acting inadvertently and without artifice. She was so mentally occupied, especially by the incredible feeling of fullness in her ass, that she was pretty much completely oblivious to anything else. She hardly even noticed Alan and Simone fucking, and the fact that she didn’t get chosen didn’t bother her nearly as much as it normally would have. Instead, she was practically re-learning how to walk. Her facial expressions were amusingly child-like as she experimentally took dainty, small steps instead of her usual swaggering stride.

Alan’s plan was to keep going until Simone had a climax, even if that meant being late for class. But one moment things were going along fine, and the next he’d somehow passed the point of return. He was taken by such surprise that he didn’t have time to work his PC muscle trick.

Giving in to the inevitable, he shouted “I’m cumming!” But by then he was already squirting his seed into the condom.

He felt a bit abashed by how “ordinary” the sex was, and the fact that he hadn’t given his partner a single orgasm.

He said to Simone, “Sorry, you didn’t cum then, did you? Normally, it’s really important to me to cum together with my partner, but I got to thinking about the lack of time, and before I knew it, things were kind of happening.” That wasn’t entirely true. In reality, his body just couldn’t take it any more after experiencing such great sexual pleasure for so long. But he didn’t want to admit that, since he wanted Heather in particular to think his stamina was virtually limitless. The lack of time made for a lucky excuse.

“That’s okay,” Simone replied. “You’re so good at all this sex stuff that it can’t be measured just in orgasms. This whole morning has been one big blast for me. Although, if you could diddle my clit a little bit, that would push me over the edge.”

“Certainly.” His body just wanted to withdraw and recover, but he forced himself to at least do that so she could get her satisfaction. He was glad when he felt her entire body tremble in his lap, showing that she wasn’t faking.

In fact, it really didn’t take him much, because Simone had been on the verge anyway. Clearly, the whole dildo sizing session had been a great delight to her, and the brief intercourse at the end was just the icing on the cake. She seemed almost giddy about the way she was allowed to treat Heather.

With Heather still intent on simply walking around, Simone whispered into Alan’s ear, “Guess what? I razzed Her Majesty big time today, and no lightning bolts struck me! Hee-hee! The harder they cum, they harder they fall, so to speak. Hee! This is simply too cool for school!”

Alan whispered back, “Don’t be so sure. We did go over the line with unnecessary teasing, and I get the impression that Heather never forgets a slight. I’d watch your back if I were you, just like I’ll be watching mine.”

That seemed to sober Simone up.

Time was short, so Alan worked Simone’s clit and pussy lips for a minute or so until she had a nice climax. Meanwhile, he was watching Heather standing there for mental inspiration. Damn. That’s all I can say, is damn. She thinks her body is the greatest thing since sliced bread, and it actually is, fake tits or not. Damn! And the high heels. What’s with me, I dunno, but I must have some kind of high heel fetish. To be honest, I think Mom and Aunt Suzy kind of made me that way, strutting around in nothing but high heels so much.

He stood up and started to look for his clothes. “Heather, when you wear those heels, I want you to think of me. You’re not just wearing them to cover for your stuffed ass, you’re wearing them as a symbol of your devotion to me. Today, and every day, when you wear heels you’re saying ‘I want my body to look extra hot for Alan. I want my thighs extra firm. I want my ass extra high. For him.’ Right?”

“Uh-huh.” She was still in a daze and not fully there, although she would repeatedly mull over his words later.

As usual, things were a bit rushed at the end. They were left with just enough time to change back into their clothes and clean themselves up a bit.

Heather was still so out of it that Simone had to dress her.

As Simone pulled up Heather’s “butt floss,” Alan said, “Same with your ‘butt floss.’ When you feel that riding into your ass crack and pulling tight on your pussy lips, think of me. Imagine my hands are pulling it up. Even when I’m not with you, I’m with you, fondling your ass cheeks and pulling on your nipples. Your body belongs to me now.”

Heather was reviving, so she paid more attention to that. A part of her wanted to scornfully say, “You wish!” and another part of her wanted to obediently say, “Yes, Sir.” She was confused and ended up not saying anything at all.

Even having practiced a little, Heather’s walk was quite decidedly wobbly as she slowly made her exit to head off to class. With her “butt floss” riding deeply between her cheeks and her tighter than tight shorts massaging her bare butt constantly with every step, she was so powerfully aroused that she had to keep all her concentration on simply staying upright and moving.

At first she scoffed at Alan’s words about her heels and “butt floss,” but they stayed with her and doubled her arousal.

As Alan walked out of the theater room, the last to leave, he thought, That went pretty well, overall. Heather’s IQ drops big time whenever she has something up her butt, so I wonder how she’ll manage in her classes. But the bigger question is, will the dildo effect wear off, or will she be transformed all day, and then day after day after that?

Wouldn’t it be amazing if this crazy scheme actually worked? I can half imagine this becoming a psychological cure used by professionals. “Sorry, Mrs. Johnson. Your beautiful daughter has been diagnosed with a case of acutely terminal bitchiness. The only known cure is, well, a bit controversial, but I have the equipment she needs…” Heh-heh! I mean, it would just be so amazing to actually change Heather for the better. What a major accomplishment that would be.

Now, I just have to deal with going to class. Jesus! After all that happened this morning, I’m gonna need a wheelchair just to get from class to class. I know I didn’t actually do that much, physically, but being on the receiving end of that much non-stop amazing ecstasy really wipes you out. Phew!