6 Times a Day

Chapter 1196: Fun with Heather and Simone



[3.5k words]

Alan was feeling conflicted. On one hand, he'd worked Heather and himself up to a fever pitch and it would be downright cruel to both of them not to cum together soon. But on the other hand, he was suspecting more and more that he was going to have a very sexually busy Thanksgiving day, so he couldn't just cum willy nilly whenever he liked. If he came now, he'd have to either wait a good long while or else it would be the last time he could get it up with her this morning.

He decided to test his resolve and delay his orgasm a bit more while giving Heather her much needed satisfaction. He remembered the oversized dildo he'd brought and figured that could be the perfect thing for the occasion.

He didn't have to worry about what she would say now that she was gagged as well as blindfolded (personally, he got a big kick out of the way she had two black pairs of panties on her head and even walked around the bed to get a better look). But, for Simone's benefit, and because he generally was a polite guy, he explained, "Heather, I need to take a rest. But you don't, so what I'm gonna do is bring out a gift I bought for you that'll make you very, very happy."

He gently stroked his fingers through her hair before softly trailing them across her cheek and along her jaw line. Tilting her head up to look at her blindfolded and gagged face, he asked, "Okay?"

"MMMM!"

He laughed because he had absolutely no idea what that meant.

Simone spoke up through the speakerphone. "I'll bet you have no idea what Heather's saying."

"You got that right."

Simone suggested playfully, "As her best friend and frequent lover, I know exactly what she means. I'm fully conversant in the language of Heather Moan. You want me to translate for you?"

"Sure. What did she just say?"

"Roughly speaking, she said, 'I'm a stuck-up bitch and my body doesn't come close to matching Simone's in its magnificent ebony perfection.""

He had a good laugh. "Somehow I doubt she said that." Since Heather responded to Simone's comment with a new burst of moans, he asked, "What's she saying now?"

"She's saying, 'It's so true! Simone speaks the wisdom of the ages.""

He laughed even harder. While this was happening, he went back to Heather's desk, found some paper and a pen, and scribbled down a note. Then he saw the webcam next to Heather's computer monitor, held the paper up to it, and asked Simone, "Can you read this?"

Simone read the note. It said: "I bought a huge dildo for H and I'm gonna give it to her now. Don't say anything about it unless I tell you, not even joking. Okay?"

She replied, "Sure. No problem."

It was strange for him to communicate by holding up a paper to a camera while hearing Simone speak from the speakerphone across the room. So he said, "Good. By the way, is there some way I can see you as well?"

Simone quickly explained for him how to do that, and he was soon able to see her on Heather's computer screen. He discovered that she had stripped nude and was busying fingering herself. She was using a speakerphone too, so she waved at him with one hand while continuing to jill herself with the other.

He could have chatted with her some, since talking to Simone was always fun, but Heather's frustrated moans were getting louder and he didn't need any translator to hear the increasing anguish in her voice.

He hurried back to Heather spread out lewdly on the bed. All in all he'd only been away a minute or so scribbling the note and fiddling with the web cam, but to Heather it seemed like an eternity.

Now that Alan knew Simone wouldn't ruin the surprise, he went to his backpack amongst his clothes strewn across the floor. He'd brought the backpack just to hold the dildo because it was so big that he couldn't possibly expect to hide it in a pocket.

It was thirteen inches long from end to end, and about two and a half inches wide for just about its entire length. It was made out of a single piece of clear solid tempered pyrex glass, shaped like a double-ended penis, complete with anatomically correct cockheads on each end. One end had a sturdy pull string and ring arrangement, with the string deeply imbedded through what would have been the urethra on that end's cockhead. The surface was actually polished smooth for minimal friction, thus being quite sanitary and requiring very little lubrication. Because it wasn't hollow inside, the glass was extremely difficult to break. It was quite heavy, weighing a bit more than four pounds, even though pyrex was lighter and more durable than regular glass.

In fact, the dildo was so big that it had actually been designed and crafted to be a one-of-a- kind novelty item more for visual show than insertion. However, Ginger at the sex shop had assured him that it could be used for vaginal or anal penetration relatively safely by women who were "size queens."

He picked up the dildo and took it with him as he sat next to Heather on the bed. He didn't have to worry at all about her seeing it, because even if she could see some through her blindfold, given the lewd way she was positioned with her ass up and her face in a pillow, there was no way for her to see her own ass.

He said, "Okay. I'm all ready here. Like I said, I bought you a nice gift. Do you want to know what it is?"

"Mmmm-hmmm!"

Despite the gag, he could make that out to be a "yes." But still, for kicks, he asked Simone, "What did she say there?"

Simone joked, "She said, 'I worship even Simone's toenail clippings and I wish I could be licking her butthole right now."" She paused, and then added, "Curious. She didn't even answer your question. Just shows how hard it is to get her to talk about anything but this unhealthy Simone envy she's got."

Heather moaned with angry frustration again. She thinks she's so funny. I'll kill her! GRRR!

He laughed, but said, "Okay, Simone. Enough of that. Seriously Heather, here's your gift. Can you tell what it is?"

He held the big dildo in one hand and started fingering her pussy with the other. Then he brought it up and pressed it against her right butt cheek. It was so heavy that it sank down into her skin despite her firm muscularity there. He pushed it in a bit deeper so she could feel its round shape. "Feel that?"

"Mmmm-hmmm."

Then he took it and started to run it through the crack of her ass. He slid it back and forth between her cheeks so she could feel the drag of friction from the glass and start to build up a mental image of the size. "Big, huh?" he asked.

"Mmmm-hmmm!"

Then he brought the insertion end to her asshole and tried inserting it a bit. It wasn't easy, though. He found himself wishing he could have three hands, one to hold the dildo and two to clutch at her butt cheeks and open them up as wide as possible. Lacking that, as well as lacking lube and lots of preparation time, he could only poke the tip of the end into her. The cockhead part of it was the widest part, naturally, and while he didn't want to push it all the way in, the head gave her an excellent sense of just how wide it was.

Heather, at long last, was finally getting some satisfaction. While the dildo itself was more teasing torture than anything, it set her imagination on fire. She had no doubts about just what was poking at her, and while she couldn't get an exact grasp on its dimensions, she could tell it was easily the largest dildo she'd ever had the pleasure of encountering. Her extreme frustration at him quickly morphed into loving gratitude.

He could tell she was nearing a monster orgasm. He made sure to play with her clit and pussy

lips just enough to keep her on the edge. Meanwhile, his erection was still quite stiff, but he was steering clear of any action or even touching anything with it so he could get one of his renowned second winds.

The key though was time. So, stalling a bit, he began talking up the dildo. "Bitchslut, I know you know what this is. Your Bitch Trainer. Your Thanksgiving Bitch Trainer. And yes, it's damned big. The question is, why did I get this for you, especially when you've been doing nothing but scheming against me and stabbing me in the back?"

He contemplated the answer to that and found himself talking in a more heartfelt manner.

"Hell, I don't know myself, except that maybe, inexplicably, I care for you. I know you're a selfish and ruthless bitch, but I also know there's a kinder and gentler Heather locked up somewhere inside you. That's the Heather I want to know. She's the one I'm trying to draw out. Also, I want you to know that, while it's true that, yes, I have a hell of a lot of fun using you as I please for my sexual pleasure, you're not JUST a beautiful hard body and a cum dump to me. I fuck you because I can, true, but also because I'm trying to get you to change. You could be so much more than what you are now. When your ass is full, you're a different person, and we all know that. I know we have a strange relationship as Sir the ass master, and Bitchslut the sexual slave, but all sex aside I also just want to be your friend."

All the while he was talking, he continued to poke the dildo against her anus while fingering her pussy or clit. Her ass was slowly relaxing, allowing him to get a little bit further in when he pushed hard, but he knew that about an inch was the best he could do for now. She was beside herself with joy. For one thing, the dildo felt great and the idea of such a huge

dildo filling her up all the way was even better. But more than that, she was deeply touched by his kind words. She keyed in on him saying he cared for her and wanted to be her friend. She didn't mind that those words were interspersed with talk about her being a cum dump and slave; in fact, that just got her more aroused than before, if such a thing was possible. She was practically beyond coherent thought at this point, drifting in a land of pure orgasmic and emotional bliss. In addition to lust, she felt her every inch of her body coursing with the far less familiar but more powerful feeling of love.

He waited for some kind of response from her. He would have taken the gag from her mouth if

it was clear she wanted to say something, but she didn't. She was content to just make sounds that were some combination of heavy breathing, moaning, and contented sighing. It was obviously a very happy sound.

He was sincere in saying that he wanted to be her friend - assuming she could at least keep the

excesses of her deeply ingrained bitchiness in check when dealing with him. But he was also

being Machiavellian and scheming, because he knew he'd need her help very soon in the conflict with the football players.

His point made, he decided to turn up the domineering "Bad Alan" and turn down the considerate "Good Alan" for fear of her growing too attached to him, given that he still planned to hand her off to Sean.

He pulled the dildo away. That caused a new burst of sad moans from her gagged mouth. He got up and walked around behind her so he was standing between her legs. Then he started pulling her down the bed so her knees were right at the edge. That made her pussy and ass line up nicely with his still raging erection. He'd put the dildo down on the bed briefly but he picked it up and resumed poking it in and out of about an inch of her asshole.

He teased, "You want it, don't you?"

"Mmmm."

"You want more of it, don't you?"

"Mmmm!"

He poked the dildo in a little deeper, stretching her a little wider. "You want ALL of it, don't

you?"

"MMMM! MMMM-HMMM!"

Heather couldn't believe how aroused she was. She knew Alan was playing her like a fiddle. She knew her helplessness and sensory deprivation only magnified her lust. She knew he was deliberately teasing and toying with her. It was sheer torture. But she loved every single thing

he did or said.

She was so agitated and aflame that her hips were swaying back and forth and front to back, making it increasingly difficult for him to just keep the dildo over her anus. Her sweat was flying in every direction as her hips gyrated.

He put the dildo down and firmly held her buttocks with both hands until she calmed down.

Her butt cheeks felt so good in his hands, especially given how they were lightly wet with sweat and cum, that he was happy just to hold them and knead them for a while.

A surge of possessiveness and "Bad Alan" aggressiveness ran through him as he gripped her

ass firmly. "These are mine, aren't they?"

"Mmmm-hmmm!" Heather's long blonde ponytail flew through the air as she nodded

emphatically.

He stepped forward and rubbed his shaft back and forth over her pussy lips. He said, "Heather, since you're obviously beyond talking right now, I'm going to do a little talking for you. A reminder. You're a bitchslut. And what do good bitchsluts do? At school, you may be

the queen, and I'll let you look like you're in charge because it amuses me. But in private, we all know who's really in charge, don't we? Around the others, you're Queen Heather, but around me you're just my dirty little bitchslut. Your body exists for my pleasure only. When I see you, say, walking in the halls at school, you know what to do. You'll rip off all your clothes, bend over, grab your ankles with both hands, wiggle your naked butt, and say, 'Your Bitchslut is ready for inspection, Sir!""

She liked that idea so much that she started screaming into her gag. "MMMEFFTH! MMMEFFTH!"

He could tell she was saying, "YES! YES!" It wasn't so much from her muffled words, but from

the way her head nodded up and down, setting her ponytail flying again. Seeing she liked his idea, he embellished, "What would you do, when hundreds of people in

the hall stop and stare? There would be dead silence, wouldn't there? Then people would start to mutter, 'Isn't that Heather, the Homecoming Queen? What's she doing naked and touching her toes?' What would you say to them?"

"MMMM! MMMM!" She was so far gone that she didn't even know what she was trying to say.

He suggested, "You'd tell them, no, you're not that Heather; you're Heather, Alan's bitchslut.

And if he tells you to get naked and suck his cock in the middle of class or the middle of the halls, you'll do it, won't you?"

Her hair flew about madly again, now that she had something concrete to agree with and nod

about.

Meanwhile, he was rubbing his dick against her pussy lips and starting to push into them more and more with each pass. She was on a constant, never-ending high, going higher and higher to plateaus of euphoria she never even knew existed. She began to wonder if it was

possible to pass out simply from feeling too good.

Then, without any special warning, he yelled, "Bitchslut, you're MINE!" and he skewered his

erection all the way into her pussy, filling her vagina completely.

That pushed her over the edge.

Now he was grateful that he'd gagged her, because she screamed bloody murder as one of the

greatest orgasms she'd ever known ripped through her. Even with the gag, her screams were quite loud. He could only hope that either the loud music covered it up enough or that her

parents were a safe distance away.

All he gave her was the one thrust into her vagina. (He was glad that he'd thought to wipe his

penis clean earlier while he was in the bathroom.) He was still trying to calm his own orgasmic urges, relatively speaking, so he didn't want to thrust in and out just yet.

As her orgasmic release detonated through her like a nuclear bomb, she felt all her energy drain away. She sagged down into the bed as if slain and left for dead.

But he wasn't done with her; far from it. He still had his own satisfaction to take care of and he was going to do that with her ass.