6 Times a Day

Alan had time in his last two classes to think about what to say and what attitude to take when he was to meet Heather after school. I’m in a very weak position. Right now I need things from her. First off, I’ve got to get this 20-page paper that one of her nerdy adoring fans is writing for her, the poor schmuck. To think that just a few months ago I was almost pathetic enough to do the same thing as that guy. Almost, but not quite, thank God.

Anyways, if I don’t get that before tomorrow morning, I’m going to plain fail out of one of my classes. Well, a C at best. That’ll throw off my chances to get into a good college, big time. It’s horrible that I’m having someone else do my schoolwork for me, so it serves me right to be in this spot. The old Alan would never have done this. I’m slowly losing my mind to my libido, it seems.

But that’s not all. Thanks to my previous failures, I also have to rely on Heather to keep the football players away. Today I got nasty looks from all kinds of people, especially the big jocks. She’s the only one with the power to keep them away, due to her “special relationship” with half the team. She has me over a barrel.

On the other hand, I have her over an even bigger barrel. She seems to want me to be her boyfriend, as crazy as that sounds. And apparently she’s quite intent on it, in her typical “Heather must have it or kill everyone else trying” kind of way. The logical thing would be to walk in there and say that we both need things from each other, be reasonable, and work out a truce. But I’m not going to do that. I simply cannot give an inch to Heather or she’ll end up walking all over me. I have the advantage of the lucky fact that she’s a little bit awed by me right now. No, my only choice is to walk in there and bluff my way through it with a strong showing that allows for no weakness or compromises.

He strode to the theater room with purpose and determination as soon as his last class, tennis, let out.

But right as he got to the door, he found Janice there. She apparently knew he was going to be there and had planned to intercept him.

He was annoyed, but tried to appear friendly. “Hi Janice. What’s up?”

She rested right up against the door so he couldn’t get past her. “Oh, not much.” There clearly was something going on, because Janice was nervous and fidgety.

Alan felt impatient. He took the opportunity this pause in his rush gave him to reach into his pocket and dial in a new setting to Glory’s vaginal vibrator. He’d continued to do that very occasionally during his fifth and sixth periods, but more frequently and with higher settings in the break in between.

Then he said to Janice, “I can tell you want to talk to me about something important. Something’s obviously bothering you.”

Janice kept her eyes downcast and shyly nodded her head.

“Okay, but can it wait a few minutes? I’m supposed to meet Heather here. You know how it is with keeping her waiting. I’ll just be a couple minutes, and then I can come out and have more time to talk. How does that sound?”

Janice readily agreed.

He knocked on the theater room door after Janice pulled back a short distance where she couldn’t be seen from inside.

Heather opened the door to let him in. Once he was inside, the door closed on its own and locked itself behind him.

Heather and Alan eyed each other warily. She was fully dressed in the same clothes she’d worn to school. She seemed alternately uncertain and fidgety, and then defiant.

What she didn’t show or say is that just a few minutes earlier, she’d snuck off and lubed her asshole in hopes that Alan would soon be fucking her there.

He stared at her with all the angry intensity he could muster. Then he said, “I don’t even know if I want to talk to you… but I’ll talk on one condition. You give me the key to this room.”

Heather protested, “But that’s the only key! I tried to make a copy, but none of the key shops would break the law to do it. I have to have that key!”

They both knew that the key was much more than a simple key. It was the only access into the theater room, the perfect place for sexual shenanigans in school. Heather’s control over it gave her a lot of power over the other cheerleaders.

He growled, “See if I care.”

She pointed out, “But I got that key so my cheerleading squad could practice in here. How are we supposed to do that if you have the only key?”

“You should have thought about that before you started spreading lies. Anyway, your squad was doing just fine practicing outside and elsewhere up until recently. Let’s face it: that’s not why you got it. You got it so you could have sex with me at school, and having the cheerleaders practice here is just a bonus.”

She thought, What a pompous asshole! As if!

But he paused, and her ensuing silence showed he was right.

He continued, “Either you give me the key, right now, or I’m walking. And don’t say you don’t have it on you because you couldn’t have gotten in here without it.”

She again tried to size him up. He looked livid and aggressive. He’d been working on his look and mentally practicing it, and he’d gotten himself emotionally worked up to make sure he could be convincing.

They stared at each other until she flinched. She was amazed, because normally she never flinched to anyone about anything. She turned aside and said dismissively, “I’ll give you the key, but only if you agree to the follow-”

“SHUT UP, BITCH! Did you hear me? Give me the key. NOW. Or I’m leaving. You don’t make ANY conditions!”

Heather had never seen Alan like this. She didn’t even know he could be like this. Even he barely knew he could be like this. She meekly fished into her pockets and handed him the key without another word.

But this didn’t seem to please him, as he stayed just as angry as before. “I lied. That’s not the only thing you have to do. Get naked, and then I’m going to tie up your hands and blindfold your eyes. Then maybe we can get somewhere.” 𝘯𝑜𝑣𝘦𝘭.𝘦𝑡

He recalled his own blindfolding experience with Glory some days earlier. He could never forget just how helpless being blind could make one feel. Xania’s complaints about helplessness from earlier in the morning also helped inspire the notion of binding her hands as well.

Heather was actually quite eager to obey these commands, because she hoped it meant that he was about to fuck her, and she knew that would always be a very good thing. But then she raised a practical point. “With what? Did you bring a rope? A blindfold?”

“No. We’ll use your panties to lash your wrists together behind your back, and if that isn’t strong enough we’ll use your bra, too.”

Her hands automatically reached up and defensively clutched at her sports bra, tightly enough to inadvertently pop out a hardening nipple. She found herself fantasizing about the many things he could do with her while she was blindfolded and bound. That seemed like an ideal way to get one’s ass fucked.

She complained, “Now wait a minute! You can’t do that. You don’t seriously expect me to just let… you…” But her voice trailed off as she saw the resolute determination harden in his eyes.

She looked down and saw what her hands were doing. They were massaging her tits. She looked back up at him with a “busted” expression. She realized she wanted sex with him too much to put up any serious resistance to his demands. Worse yet, she realized he knew it too.

He barked, “Get to it. NOW! And no talking. Period!”

He felt a bit like a Marine sergeant, but the approach worked. She quickly stripped. Her panties stretched to make an excellent binding for her wrists.

With Heather buck naked and bound, he paused to check her out. Hot damn! She is one seriously sexy bitch. So friggin’ firm and curvy and tanned. She’s given me a serious boner, just like that. It’s such a shame that, with a body like that, she has the personality that she does. I can feel “Bad Alan” coming on.

He pulled out Glory’s panties from his pocket, which he’d taken from her at the end of lunch with this purpose in mind. They were still wet with her pussy juices, and he couldn’t resist taking a good, long, melodramatic sniff from the pleasing scent that lingered in them.

Heather took one look at the damp panties in his hand, and protested, “Oh no! You’re not putting THAT over my eyes! Where did those come from?!”

But he merely said in a no-nonsense tone of voice, “Here’s your blindfold,” and then wrapped them around her head. The fabric pulled exceptionally tight as it went completely around, and yet there was enough fabric left over to tie a knot at the back of her head. He purposely put the wettest part of Glory’s panties right over Heather’s mouth.

She muffled out, “Gross! What is this disgusting shit?”

“It’s called humiliation,” he responded coldly.

She was burning inside, and she mentally vowed revenge upon him and whoever had worn the panties. This is an outrage! NOBODY insults Heather Morgan and gets away with it! Not even Alan fucking Plummer! He’s going to pay for this! Pay!

She spoke through clenched teeth into the used panties. “At least tell me who they belong to.”

He grinned as he thought how she would explode if only she knew they were Glory’s. “I also said no talking, so you’re going to have to pay for that. As punishment, I’m going to go now and leave you to stew for a while. Think about your shitty attitude. While I’m gone, I want you positioned with your ass high up in the air and your butt hole ready and waiting for whatever I feel like doing to it. Remember that I have the key now. If I walk back into this room and see you in the exact same position, with your hands still tied, your eyes still blindfolded, and your ass proudly thrust up high for taking my cock, then maybe, just maybe, I’ll fuck you up the ass. If not, then I certainly won’t. Ever. So it’s all up to you. goodbye.”

She thought, My butt hole? Ohmigod, he’s gonna fuck me in the ass again! Her heart fluttered, and her pussy and ass suddenly tingled with great arousal.

He made a quick exit from the theater without looking back. He left behind a completely bewildered, amazed, bound naked and blindfolded head cheerleader, desperate for sex.

She didn’t expect that kind of treatment from him, and she still couldn’t figure out what to say or how to act. What the FUCK?! Who does he think he is? He needs to fucking DIE for this dirty panties bullshit. But… my ass! My ass! God, I need his cock so bad!

He closed the door and leaned up against the outside of it, huffing and puffing more from mental exertion than anything else. I did it! Phase one has worked!

“Alan?”

He looked around and realized Janice was still there, and still wanting to talk. So he collected his wits and tried to focus on Janice and her problems.

She turned out to be very eager to talk, and once she got started she practically poured her soul out to him. She wanted to talk to him about Joy. She hoped that with his great sexual experience he could give her some advice.

It turned out that thanks to the orgy Alan attended with Janice, Joy, Heather, and Simone two days before, Janice and Joy had broken a barrier and were engaging in lesbian sex with each other. But, ironically given her name, Joy felt no joy in doing this. Janice could only make Joy do anything with her by saying that Heather had ordered them to practice, but for Joy it had all the pleasure of a dental visit. When she’d said she wasn’t a lesbian or bisexual, she was being completely sincere.

Joy did get a little bit of satisfaction when lapping at Janice’s pussy, simply from knowing that she’d managed to make her best friend cum and made her happy. But it was nearly impossible for Janice to get Joy to cum, and if she did, the victory was a very hollow one, for both of them. Janice wanted Alan to tell her what to do, how to make her best friend become a genuine lesbian lover as well.

Alan was stumped. He had at least a glimmering of how much Janice was in love with Joy, and he really wanted to help, but he didn’t know what to say.

He thought, I’m really the wrong person to ask. I kind of figured all women were naturally bisexual if given the right opportunity. But what better, more loving opportunity does Joy have than with Janice? And yet, still nothing. That little “insight” pretty much wipes out all my “expertise.” Shit.

He tried to explain to Janice that sometimes when you desire someone they don’t desire you back, and that’s all there is to it. There’s nothing you can do about it, and the more you try to force it, the more painful it gets. He pointed out that physical love was just one kind of love, and that the love Janice and Joy shared was obviously a strong one and possibly a lifelong one.

He suggested she revel in that, and try to avoid physical contact with Joy for a while as further such encounters might only make things worse in reminding Janice what might have been. He promised to get Heather to back off from forcing them together, if that was a problem.

Janice cried quite a lot on his shoulder.

He felt a bit of a cad, since his advice was so wildly at odds with his own life. He pretty much expected physical love from every beautiful female he desired, and he played dangerously with their emotions in the process. He’d even put Janice and Joy together without thinking, during the orgy with Simone. He felt like he was juggling many women’s hearts in the air, and it was only a matter of time until they came crashing down. Yet he was proud of his advice. He liked to think that it came from the “Good Alan,” and that it would do Janice some good.

Unfortunately, thinking of the “Good Alan” reminded him of the “Bad Alan” and the situation with Heather waiting on the other side of the door. He asked Janice what time it was. When she told him, he realized he’d kept Heather waiting for over fifteen minutes. That was much longer than he’d planned, but the conversation with Janice had taken on a life of its own.

He gently kissed away Janice’s tears while he gave her a warm farewell hug. He gave her an open invitation to come and talk to him about anything at any time. He figured the discussion had brought them much closer together.