6 Times a Day

Iveyflame Special [ 3 / 5 ]

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After that, Katherine and Alan dressed and went to the living room to play the video game “Grand Theft Auto III.”

Alan was actually greatly relieved to experience this revival of old habits. He was even happy to see his sister completely clothed in relatively normal clothes, just as Susan was fully clothed while she worked in the nearby kitchen. To be honest, he was a little weirded out from having such prolonged stimulation sessions with Suzanne, Susan, and then Katherine, and particularly by having it all openly acknowledged by everyone. For one thing, it simply seemed too good to be true, so he was almost expecting some kind of problem to develop.

Katherine had seen that he really needed a mental return to normality for a while, so she purposely avoided any flirtation or sexy exposure. Indeed, he was happy to see they could still relate just as they had before his six-times-a-day diagnosis. Soon they were laughing and having a great time. The only lingering evidence of sexuality was the smell of his cum and a slight sheen to her face from her facial.

About an hour into their video game fun, Amy came by and found them in the living room, sitting on the floor in front of the big-screen TV. She was wearing a powder-blue Chargers jersey and shorts. She wasn’t a football fan, but she liked how the jersey looked, and she knew Alan liked it. She said, “Hey, peeps! What’s up?”

Alan explained, “We’re just playing around, as you can see.”

Amy smiled, like she usually did. “Cool beans! Can I join in?”

Katherine replied to her, “Sure thing. In fact, why don’t you take over for me? I’ve got some things to do in my room.”

“M’kay!”

In truth, Katherine didn’t have anything really pressing. But she didn’t like playing Grand Theft Auto, as she considered it too violent. She’d just been playing because she enjoyed being with her brother. She’d been hoping he might get aroused and need some help. But that didn’t seem to be in the cards, and she’d had her fill of the game.

After a little small talk with Amy and Alan, Katherine stood to go. But she’d only taken a few steps when she saw Amy peel out of her clothes in a flash.

Alan asked in surprise, “Aims, what are you doing?!”

Amy kept right on stripping. She already had her shorts off, and now she dramatically pulled her jersey over her head. “Is this cool, Bo? I figure it’s cool. Everyone’s all hunky-dory about nudity around your house lately, right?”

Before Alan could answer that, Katherine said to Amy, “That’s true in general, but you have to remember that there are some limits on what Alan can handle, both physically and mentally. Things have gotten really sexy here a lot lately, so sometimes he needs to just sort of rest his brain. Right, Bro?”

Alan nodded. “Right. That’s definitely true. However, Sis, Amy loves nudity so much that I don’t want to disappoint her. I can handle it. Besides, I’ll be looking at the screen all the time, not her.”

Katherine looked at him with concern. “Are you sure? I don’t want you to mentally overheat or something.”

He waved her away. “It’ll be fine. If not, I’ll just ask her to put her clothes back on.”

“Yeay!” Amy had been standing, but she dropped down to where he was sitting and gave him a quick hug and a kiss. “Coolio! Alan, you rule-lio!” She giggled.

Katherine looked at Amy with concern. That hug and kiss seemed merely friendly, but Amy was nude while doing it. Katherine was worried that if her brother didn’t get a proper mental rest, he wouldn’t be up for more sexual fun later in the day. She asked him, “Are you SURE?”

“Sure, I’m sure.”

Katherine reluctantly started to walk away. “Okay. But if things do change and you need some help with your special problem, remember that I’m right upstairs.”

He nodded, and looked back to the screen. “Got it.”

As Katherine walked up the stairs, Amy sat on the floor right where Katherine had been earlier. She asked, “By the way, where’s Aunt Susan?”

“I think she’s outside, doing some gardening.”

“M’kay. Cool. So how does this work? I’ve never played before.”

He started to show her how to play the game, while trying to keep his eyes on the screen instead of her naked body.

— — —

Back in her room a few minutes later, Katherine wrote:

Dear Diary,

I got to titfuck Brother’s big cock today! As usual, it was AWESOME! I love being able to gobble on his knob while squeezing the rest of his shaft to death with my boobs. I could do that ALL DAY LONG! And before that, I got to watch him blow his load down Mom’s throat. That was surprisingly fun! I love what that suggests about how we’re going to share our sexy fun times from now on. (Knock on wood!) I’ll tell you more about it later, ‘cos I want to remember every last little spermy detail.

But then he got all normal on me. I guess he needs some time to adjust to this whole fuck-toy idea. Why can’t he understand that when you have a sister who also is your fuck toy, you can have your yummy cock pleasured nearly every hour of the day? SIGH! I’m pushing too hard, aren’t I? He even still has issues thinking of me as his fuck toy (or one of his fuck toys, I should say – just thinking about him having many busty, beautiful sex pets to splooge on gets me so horny!). I’ll just have to take it slow for a while and tone down the language until he realizes my rightful role is to love him and serve him. I guess there’s no spanking for me today. Shucks.

That’s okay, though. The important thing is what happens in the long term. We’re just gonna get closer and closer and closer until he’ll be not only my brother and my lover and my best friend, but he’ll also be the father of my children! And, I dare say, maybe even my MASTER too!!! Then we’ll live together happily forever and ever. Sure, he’s way too studly now to be happy with just one woman, but as long as he knocks me up there’s no way he could ever leave me. I’ll always be right there by his side, one of his favorites! Besides, it just feels so good and so right if Mom, Aims, Aunt Suzy, and I become the inner core of his harem!

Mmmm… Diary, as usual, I find myself writing with one hand while fingering all my tingly spots with the other. I shouldn’t have started thinking about his powerful seed flooding my vagina, with his cute little spermies finding an egg and fertilizing it! Oh God! I’ll write more later. Gotta go! Gotta cum!

Alan was explaining to Amy how to play Grand Theft Auto III, but he hadn’t gotten very far when she cut him off.

“Hey, Bo, before you tell me all that, can I ask you some stuff about what Kat was just talking about?”

“Sure.” He could tell from her serious tone that it wasn’t just a simple question. He gave up on trying to play the video game, at least for the moment, and turned to face his nude “cousin.” “What’s on your mind?”

She started hesitantly. “So, like… I’m kind of confused. Nobody seems to want to tell me anything, but I sorta figured out that you need help with your thingy six times a day, right?”

“Right. Not exactly six times each day, but that much on average.”

“M’kay. So we’re supposed to stroke it and stuff, until you have a big squirt? Like the way you and Kat let me do for a while earlier? That counts as one of your times, right?”

“Exactly.”

“And if I titfuck you or suck you until you cum, or other ways, that counts too, right?”

“Right. Once your mom lets you do all that.”

She nodded. “Cool. I think I get that; it sounds easy enough. But… six times a day would be no problem for a week, but is that, like, forever?! ‘Cos that sounds hard! I mean, what if you just don’t feel like having your thingy squirt at all one day? Or you’re just super busy that day. The next day, you’d have to do it TWELVE times! Right?”

“Right. And that’s the real challenge. This may not last forever, but it’s gonna go on for the foreseeable future. Luckily, there are a variety of different ways to do it, like how you titfucked me twice, and variety is good. Also, I’m getting help from a number of women, so that keeps things really interesting and exciting for me with even more variety. I really need to get inspired every time so that my ‘thingy’ can get stiff.”

“M’kay, cool. You’re totally gonna let me be one of your regular helpers, aren’t you? ‘Cos I’ll be super double duper bummed if you don’t.” She gave him a frowny face that was still playful.

He smiled at her. “Of course. If you want to, that is.”

“Oh, totally! Since you already agreed that I’m one of your official personal cocksuckers, you’re kind of stuck with me.” She struck her tongue out playfully. “Even if Mom says I’m not allowed to do any sucking just yet.” 𝗻𝗼𝘃𝐞𝐥.

With the video game temporarily forgotten, he ran a hand through her hair. He was still trying to take a sexual break, so it was only meant as a tender gesture. “I’m really lucky that I’ve got you, Sis, Mom, and your mom to help out. I can’t even begin to tell you how much I love it and appreciate it.”

“Yeah, but we’re not all of your helpers, right? That’s something else I’m super curious-y about. Who else is helping you, exactly? And who else do you want to help?”

He explained patiently, “By the way, you can just say ‘curious,’ not ‘curious-y.’ Anyway, I wanna be clear that help for this kind of thing is really unusual. I’m super lucky to be getting any help at all. Normally, a guy never gets to have a girl touch his penis unless she’s been his girlfriend for a while. And I don’t even have a girlfriend at the moment.”

She pointed out, “But you asked Christine out recently, and she turned you down. That’s a big bummer for you, but I noticed lately at school that you and her are all chummy again. So does that mean she’s helping you with your thingy problem?”

A brief vision flashed in Alan’s head of Christine helping him in that way. Improbably enough, in his mind she was kneeling between his legs and bobbing on his stiff boner in the exact same style, and with the same enthusiasm, as Susan usually did. She was even fondling his balls with one hand.

That was plenty arousing, but what got him going even more was what she was wearing. She wore a pornographic version of a private-school uniform. What was curious about it was that her top covered all of her arms thoroughly, and the neckline showed little more than her neck, but further down the fabric only came to the top of her breasts, leaving them exposed in their full glory. The skirt was similar: it was far too short to cover her pussy or more than half of her ass even if she were standing up straight.

The clothes blew his mind because they implied a sexy story. He realized that in his fantasy, not only was Christine sucking his cock in front of his teacher and classmates, but because her official clothes left her privates always exposed, that meant she had the permanent duty in school of serving him sexually whenever he desired it. (In theory she could have been serving others too, but it was his fantasy and he was far too possessive to even consider that possibility.) Furthermore, her face was cherry red, indicating that she never got over the thrill and humiliation of serving him like this, even though she did it for him regularly, several times a day.

Alan’s penis had been flaccid, even though he was talking to a fully nude Amy. But, within seconds, it erected to full size. He was caught flat-footed by that unanticipated arousal, so he looked away in embarrassment.

Amy couldn’t help but notice his newly-erect state, since his penis had engorged so quickly and markedly, tenting his shorts. She raised her eyebrows and pointed. “Wow! What happened there?! It’s like, I’m naked and no problemo. But then I start talking about Christine and bammo! Super whammo! Instant stiffy city!”

He blushed in genuine embarrassment, in part because he didn’t want Amy to feel bad. “I’m sorry! Amy, you’re extremely beautiful and desirable. You turn me on in a big way. But I’ve had a crush on Christine for the last two years, and I’ve always considered you to be like family and off limits until, well, the last few days. So please don’t be offended!” He considered sharing that momentary bizarre, vivid fantasy with Amy, but realized that might make her feel even more jealous.

Amy smiled encouragingly. “Don’t worry. I get it. Things are changing for me too, so I totally get it. Besides, she is super hot. Like, supermegaultraboilinglavaburningfire hot! And that’s really hot!” She giggled. “Especially if she helps you with her boobies. I think I’ve got pretty nice boobies, and I totally love helping you with titfucks…” – she held her breasts out with both hands, looking down at them and lifting them slightly – “but hers are spectacular! And doubly so because of her age. Just think what she’ll look like in five years. She’ll be all boob!” She giggled at that.

Alan chuckled some too, but he was still very worried about offending Amy. “Yeah, that’s true. But Aims, you’re so beautiful that it hurts. A lot of guys I know think you’re the most beautiful girl at school, and that’s no lie. It’s just that I have kind of a history of wanting Christine for a long time now.”

Amy smiled easily. “Don’t worry, Bo. I totally get it. No worries. I’ll bet you thought about titfucking her, haven’t you? Have you dreamt about sticking your thingy between her big boobies and feeling her squeezing and slide them all over it?”

He thought, If only you knew! Titfucking is only a part of it. I’m sure that, in my fantasy world, she titfucks me all the friggin’ time! But that’s wrong. If any girl I know is a modern, liberated feminist, it’s Christine. So why do I have a twisted fantasy about her being some kind of… sex slave? All this sexual success I’ve been having must be going to my head! It’s wrong! But, dammit, she IS “super hot!”

Amy stared off into space, as if in confusion. “But what about lube, so things don’t get too friction-y? It would be better if she got some oil or lube and kind of oiled her boobs up first. Then your thingy would slide around no problem at all!” She smiled at that solution while running her hands over her own breasts as if lubing them herself.

Alan groaned lustily. He found himself gawking at Amy’s hands sliding around her breasts, which made him groan even louder. He closed his eyes, but that didn’t help because it left him with a vivid vision of titfucking Christine’s very oily tits, while she still wore her ridiculously-undersized school uniform.

Amy said, “Uh-oh! I must have said something wrong. And you must be in a lot of pain. It looks like it’s coming from your crotch-y region. Here, let me help.”

While Alan was still out of his mind thinking about a glorious Christine titfuck, Amy put her hand in his shorts and had it on his erection before he knew what was happening. Then just as quickly, she started stroking him.

His eyes opened in surprise. “What the heck are you doing?!”

She smiled. “I’m one of your official helpers now, right? This is what we do.” She slid his shorts down below his balls and resumed stroking.

He groaned lustily. “You really don’t have to do that. You shouldn’t feel obliged to help me.”

“Do I look reluctant? I’m seizing the moment – and the cock!” She giggled at that. “It makes me feel good to make you feel good. When your thingy gets all stiff and you’re not getting any help, then it gets all ouchy and hurty. But if we help it, then it feels really good! And then, if we keep helping until the white stuff shoots out, then that feels really, really good and your problem goes away for a while.”

He groaned again. “Oh man! That’s true!” He thought, This is supposed to be my mental break time. I was so not in the mood. But then she had to strip and talk about Christine, of all people! Damn! Now it’s hopeless to get back in the video-gaming mood. I might as well let her keep stroking, since I’m going to have a raging boner anyway.

There was silence for the next minute or two while Amy experimented with slightly different ways of jacking him off. She was surprisingly good at it already, with a strong focus on his sweet spot, but she was still learning his penis. Eventually, she asked, “So how am I doing?”

He opened his eyes and looked at her loving, smiling face. “Good! Really great. Almost too good. The fact that it’s you doing it is super-exciting. Aims, please don’t be offended by how I got hard. You thrill me; you really do. It’s just that I wasn’t in an aroused mood at all, so it kind of took a one-two punch to get me going.”

She kept on smiling. “No worries. Besides, I understand about you and Christine. She’s the one you asked out a little while back. In fact, she was the only one. I know you have a special thing for her. Is this how she does it? Does she stroke your thingy, like I’m doing right now? I was watching what Kat was doing and I’m kinda trying to imitate that.”

“You’re doing a great job, like I said,” he replied. “Almost too good. My heart is really pounding hard right now, and I’m getting goose bumps all over. Unh! So good! But, uh, the truth is, Christine isn’t helping with my thingy at all. We’re just friends. She turned me down when I asked her out, as you know, and I’m not stupid enough to ask her out again.”

After a pause, Amy said, “Oh. Huh. That’s a bummer for you, I guess, ‘cos you really, really like her, don’t you?”

“I do. Sure, she’s so beautiful that it’s ridiculous. But we connect emotionally, and personality-wise. Intellectually too. I love talking to her. I’m always learning new things. I feel like I can just barely keep up with her; she makes me stay on my toes. I respect her and admire her in so many ways, and she’s also, well, a stone cold fox!”

Amy purred happily. “Mmmm… I can feel how much you’re into her by your thingy; it gets all throbby and warm when you talk about her.”

“That’s due to you too, Aims. Big time! In case you didn’t notice, I’m having to avert my eyes from you most of the time. If I look at you for very long, I’ll get too excited, and that’s not good. Then I’ll cum, and I don’t want to cum too soon.” That was true; he had been averting his eyes for a while.

Amy said as she stroked, “That’s pretty neat-o. You know, I’m totally bummed that Mom won’t allow me to suck on you, ‘cos your thingy is looking super yummerific right now. I wish I could, like, take it in my mouth and slide my lips back and forth on it, and lick it all over too. But… hey!” She suddenly brightened. “You know what? I AM allowed to titfuck you, right?”

“Well, kinda.” He looked around nervously. They were in a highly exposed location, and he highly doubted Suzanne would approve of Amy giving a titfuck. That was probably an oversight when she’d said she wasn’t allowed to use her mouth on him. And since he didn’t want Suzanne to know, he couldn’t have Susan know either, since they shared nearly everything.