6 Times a Day

Iveyflame Special [ 7 / 12 ] 3K 𝒷𝓭ℴ𝓋𝓵.𝒸ℴ𝓶

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Alan’s dinner with Christine had lasted over three hours, mostly because of good conversation. So it was getting late when Alan came home, to find Susan and Katherine still waiting up for him. (Their hour-and-a-half long movie had long since ended.) They were both wearing ordinary clothes, on the off chance that he’d bring Christine back home with him.

As soon as he came through the door, both of them wanted to know everything that had happened, and were especially curious if anything physical had happened. As he removed his suit coat he started summarizing his evening with Christine. When he said that it had remained entirely platonic, Susan appeared crestfallen.

But Katherine was ecstatic. She jumped around and threw her arms into the air. “Woo-hoo! Sweet!”

Alan tolerantly waited her out.

When Katherine had calmed down some, Susan said, “Let me see if I get this straight. Christine was with you for over three hours and she didn’t so much as jack you off?”

“Yep.” Seeing the severely disappointed look on Susan’s face really made it hit home just how important the stimulation of his penis had become for her.

Susan put her hands on her hips, like she was ready to give Christine a stern lecture. “Hrm. I don’t know what’s gotten into Angel, but I already don’t like this Christine very much, if she’s gonna be like that! She apparently thinks she’s better than everybody else. It’s especially galling since you say she’s got the bust and looks to be Alan-worthy. Tiger, you need a girlfriend in school, and you deserve the very best. Who better than Christine?”

Katherine said with great annoyance, “Um, Mom? Hello?! Did you forget I’m listening too?”

“Of course I know you’re here. You would be my first choice, no question! You’re the very best in every way, including the most beautiful, in my book! But unfortunately, everyone knows you two are siblings. So how could it be you?”

Katherine was taken aback by that. It was a good point, and she didn’t know how to respond.

Susan turned her attention back to Alan. “In any case, Tiger, your penis has gone over THREE hours without any stimulation whatsoever! You must be horribly backed up with sperm.”

He grinned. He could see what was coming. “That’s true. I don’t know if she intended it or not, but she kept my dick rock hard for most of the evening. She wore a low-cut dress that left me positively drooling.”

Susan looked distressed. “Hrm. Not good. Not good at all. Well, Angel and I were discussing this while you were gone. I’m willing to help you with your problem, but as you know, Angel is being grounded. She’s allowed to jack you off just once today and nothing else, and she’s already used that one up. So, if you want me to, I could take care of you.”

He replied, “What? Are you crazy, Mom? Of course I want you! I want you and Sis both equally of course, but maybe Sis could at least watch?”

Katherine had her arms folded and had gone from joy to irritation with the reminder of her punishment. She said, “Grrr. But I guess that’s better than nothing.”

Before Susan could disapprove, he unzipped his fly and flipped out his erection. “Great! Hey Mom, I’ve got an idea. Before I take this outfit off, why don’t I get some mental AND physical relief? I could pretend that you’re Christine and we’re doing our date over.”

Susan’s face lit up. “Brilliant! Son, you’re so creative. I love it!” She reached out and lightly brushed his erection with her hand. But then she wistfully let go, and said, “Wait right here though, while I get dressed in something sexy. What color was her dress?” She rushed to the stairs as she talked.

He replied, “Black. Kind of silky. It showed off a LOT of cleavage, like practically down to her belly button.”

“Hmmm, maybe she’s not all that bad,” Susan said as she walked away.

Katherine followed after her. If she wasn’t going to be able to take part directly, she at least wanted to help with the visual stimulation.

After a few minutes, Alan began to wonder what was taking so long. He crept to the top of the stairs and was able to listen from there, since Susan had left her door open and she and Katherine were arguing boisterously.

Susan was complaining, “No, I can’t go like that, Angel. It’s completely improper! I’d be sending the wrong signal.”

“And what signal is that?” Katherine goaded, “Maybe you’re signaling that Mommy wants to suck on a spermsickle? Lick on a bally-pop? Would that be so bad, to let him know that you know your place is on your knees with his big dick in your mouth?”

“Really, Angel, you’re so vulgar.”

“Hey. I’m just calling a spade a spade. If you go down there topless, he’ll get so hot and hard that your tonsils will be drowning in cum within five minutes.”

Susan couldn’t quite hide her eagerness for that. “You think? I don’t know. I mean, I’m supposed to at least start out looking like Christine. I have to wear a silky dress that shows lots of cleavage, and that’s that!”

Katherine goaded, “If you go topless, how much more cleavage can you show? Besides, you don’t have a really good, silky black dress.”

“I know!” Susan wailed unhappily. “As one of Tiger’s personal cocksuckers, that is simply unacceptable! Should I call up Suzanne for help?”

“No! It’ll take too much time. Remember, he’s waiting downstairs with his big cock poking out in the air.”

“Mmmm…! Yummy…”

“Mom, focus! Look, clearly you’re torn between the lovely sexy new you and your prudish past. You need a push. I know Brother gets to control what you wear and what you don’t, but let me help, kind of as his assistant for when he’s not around. I can cut through your waffling and get you in something that will make his cock stick straight up in attention!”

“I don’t know…” Susan said doubtfully.

“Leave it to me. Trust me. Think about it: his cock literally sticking straight up, he’s so excited by your outfit! Think of all that hard cock-meat filling your mouth as a result!”

“That does sound pretty good,” Susan admitted. “Okay, what do you suggest? But nothing too wild!”

Alan snuck back downstairs, confident that Katherine had the situation in hand.

Susan came back down the stairs a few minutes later. She was all dolled up, even wearing glossy lipstick, eye shadow, and a necklace.

Alan looked up at her and whistled, but he also chuckled. “Mom, isn’t your outfit there missing something?”

She wore a fancy light coffee-colored dress but there was no fabric of any kind above her stomach, leaving her topless.

Even though he had figured she’d come down topless after what he’d overheard, he didn’t have to pretend surprise because he was genuinely floored at just how scorchingly hot she looked. He thought, I hope Sis helped pick that out. If that’s “nothing too wild,” I wonder what the wild option was!

Susan was bursting with eagerness. “I’m sorry, Son; it’s just that I have such a hard time keeping my chest covered when I’m around you. The clothes just seem to fly off. Should I go put the rest on?”

“No, please. I can’t really complain if- Oops! For pretend-date purposes, I haven’t seen you yet. I have something in the car I picked up on the way home, hoping this would happen. Hold on; I’ll go get it.”

He put his suit-coat back on. He also tucked his erection away and zipped up his fly. He went to the garage and picked up two bouquets of flowers that he’d bought at Safeway on his way home. He’d made a note of what a great reaction his flowers had caused with Christine, and wanted to see if he could repeat that success.

Instead of walking the usual way from the garage directly into the house, he went back outside and rang the doorbell.

Susan answered it in her topless mocha-colored dress, with her arms over her chest for fear of the neighbors seeing.

Alan immediately pushed into the house so no one could get a free peek at his semi-naked mother, even though their front lawn was so big with so many bushes and trees that there was little to no chance of that happening. He noticed Katherine had come back downstairs and was sitting on a nearby sofa, watching with a slight frown on her face. He held both bouquets behind his back.

“Hi Christine. Damn! You look fantastic.” He joked, “That’s an unusually revealing outfit, compared to what you usually wear at school.”

Susan knew he was holding something behind his back, but she didn’t press to ask what it was. Instead, she suddenly realized that she’d never talked to Christine, except in passing at a couple of school events. She said, “Time out.”

She turned to Katherine. “Oh dear. Angel, I don’t know Christine from a hole in the ground, except for a few things, I suppose. She’s never even been here to visit. How does she talk? What should I say? What’s she like? All I know is that she does really well in school, she’s kind of uptight and unwilling to help out with Tiger’s blue balls, and her breasts are as big as mine.”

Katherine stood up and wandered over. “There’s not much more to know, except that she’s a pathetic lonely virgin and she’s justly nicknamed the ‘Ice Queen.’ So harden your heart and act like a cold-hearted know-it-all bitch and you’ll do just fine.”

Alan complained, “Hey Sis, that’s totally mean and you know it. We’ll talk about your Christine issues later, but for now don’t ruin my ‘date’ with your negativity. She’s a good friend of mine, and she deserves a little respect. Okay?”

Katherine gave him a bit of a look, but then relented and nodded sullenly.

As he turned back to Susan, he noticed that she was hopping about excitedly, holding her breasts to stop them from slapping her in the face. “I’m on a date with my son! Did you hear that, Angel? My big cum-filled boy wants to spend a romantic evening with me and seduce me!”

He chuckled. “That’s right, Mom. But remember that you’re Christine now, okay? You don’t need to be exactly like her; just pretend to be an extremely intelligent and, yes, a kind of demanding know-it-all teenage girl. Unfortunately, a bit prudish and sexually repressed too. Remember, I asked her out and she turned me down. Got that?”

She nodded, but there was a new fire in her eyes. “She turned you down. How could I forget that? What is WITH that girl? She could have been slurping on your cock for weeks by now. The fool!”

He ignored that and tried to get the role-play going. “So… No. You know what? I’m gonna go back outside, and then come back in again. Okay?”

He did just that, although it was more of a token opening of the door a couple of inches and then closing it again, and he was careful to make sure his flowers weren’t visible. He turned back to Susan and looked surprised. “Christine, you look fantastic!'”

“Why, thank you, kind sir! And look at you. Don’t you look good enough to eat? Alan, I’ve never seen you in a suit before. It makes you so handsome.”

“And I’ve never seen you in a dress like that before.” Very mindful of her bare breasts, he joked, “You should wear that to school some time.” But then he turned serious and turned on the charm. “I’m speechless before your beauty. I’ve been your number one admirer for so long. But what I can’t express with words maybe I can say with this.” He pulled one of the bouquets from behind his back. “For you.”

Susan’s eyes went wide and she squealed like a stuck pig. She started wildly jumping around. Naturally, that sent her big tits flying, so she had to rest her arm across them to keep them somewhat restrained. “Oh my God! My God! This is so exciting! My son is too wonderful for words!”

He was all smiles, but he cautioned, “Remember, you’re Christine. Although I did buy the flowers for you, Mom. It’s just a small way for me to show you how much I love you.”

Without further ado, she threw herself at him and kissed him on the lips with unbridled passion. She shoved her tongue so far into his mouth that she seemed intent on trying to deep throat him with it.

He loved her attention, but he had a hard time keeping the other bouquet hidden behind his back, especially since Susan was playing grab ass.

Suddenly she pulled back and stared wildly into his eyes from inches away. “Good Lord, you’re gonna get SO lucky tonight!” She dropped to her knees.

He laughed. “That’s funny. Christine said the exact same thing when I gave her the flowers.”

Katherine had retreated to the sofa but suddenly stood up and stormed over to Alan. “She did? And you gave her flowers? You said it wasn’t a romantic date!” She was angry.

Susan didn’t have anything to say; she was busy unzipping his fly and fishing his erection out of his pants. She looked at all the pre-cum that had built up from so much anticipation and joked, “Pre-cum to momma!”

As she started licking his cockhead, he thought back to how he’d told her that Christine was a bit prudish and sexually repressed. He laughed inwardly, Yep, Mom. That’s what I call prudish! But he didn’t have a chance to tell her that she was out of character for the role-play, because he needed to deal with Katherine before she managed to build up a full head of steam.

Luckily, he had the other bouquet of flowers, so he brought them out. “Uh, Christine, I noticed you have a younger sister who is in every way as beautiful as you. Here, Katherine, these are for you.” Susan’s tongue was flitting all over his sweet spot, but he tried not to notice.

Katherine didn’t jump about, but was more hushed with awe and disbelief as she took the flowers from him. “Really? For me? You were really thinking of ME?”

He felt the need to temporarily break out of the role-play, which wasn’t exactly working too well anyway. “Of course I was thinking of you. I love you! On any given day, hardly an hour goes by when I don’t think of you somehow. I love you as much as any brother ever loved his sister. It’s like you’re a part of me instead of us being two separate people. You know what I mean?”

Her face lit up like the sun. “Brother! I know exactly what you mean! Oh! Oh! … Mom, did you hear that?”

Susan was already busy slurping on Alan’s erection. But as she licked up and down and all around it she managed to say, “I heard. That’s so romantic!” She was so inspired by the touching moment that she took his entire cockhead into her mouth and tried to suck his stiffness all the way down to its base. She repeatedly gagged since she didn’t know how to deep throat him, but she got as close to deep throating as she could.

Alan found himself in a tongue duel with his sister as she kissed him with the same kind of intensity Susan had been using a short time earlier. He marveled at the fact that he was kissing his sister while being blown by his mother. The physical and mental thrill was simply unbelievable.

In fact, Susan was so intently and enthusiastically using her lips and tongue that he already had to worry about blowing his load. His PC muscle training kicked in. He was rapidly getting very good at that, out of sheer necessity.

Finally, Katherine and Alan had gotten so carried away that they had to stop kissing just to breathe.

Katherine switched to planting kisses all over his face. She said, “Mom, I’m so happy! I’ve never been as happy as this! Can I please suck him off? If I can’t, I don’t know what! But I’ll be so bummed.”

Susan was busy making her usual “mmmm” noises. But after some long moments she finally came up for air. She was still licking and stroking him with one hand while her other hand held the bouquet. She said absent-mindedly, “That’s nice, Angel. But can’t you see Mommy’s busy? Mmmm. Mommy has a big cum-filled cock she needs to drain dry. Maybe later. … Mmmm! MMMM! … After all, you are being grounded.”

“Grrr! So. Un. Fair. GRRR! I wish I was being grinded, rather than grounded.”

“Hey,” Susan chided. “Don’t even hint at intercourse. That’s not allowed. We don’t want” – she paused to fit all of Alan’s cockhead into her mouth and then let it go – “to” – she did it again – “be” – and again – “cock” – she spent a long time licking and sucking it before coming up for air – “teases.” She giggled, then went all-out on his erection with her mouth and free hand.

By this time Susan had managed to get Alan’s balls hanging out through his fly, so she spent some time kissing and sucking them too. Her hands, tongue, and lips were never idle.

Katherine had time to think, so now she switched back to sweetness and light as she resumed kissing Alan all over. She figured she could at least have her brother’s upper body to play with for a while, since her mother was so preoccupied down below. Katherine ran her hands all over his chest. “That’s okay. I’ll make do. The important thing is that you love me, Brother.”

“I do.”

A lot more necking and sucking followed. Both women shed most of their clothing, even though Alan barely managed to remove just his suit-coat. Even his tie remained hanging loosely around his neck, because his hands were too busy exploring his sister’s shapely naked body to waste time undressing.

Finally, between French kisses, he had a chance to say, “As much as I’m enjoying this, can we take a time out? My dick needs a break if I’m gonna last much longer. Not only that, but I was really looking forward to a fantasy version of my date.”

The two horny women pulled off. Somehow they’d managed to put their flower bouquets on a table, but now it seemed as if they were rediscovering them all over again. It took another minute or two of them French kissing him and fondling his cock before they let him go.