6 Times a Day

Iveyflame Special 🔥 [ 4 / 15 ] 3.5K words

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Alan closed his eyes and started to drift off to sleep. But his night wasn't over as soon as he'd thought it would be.

Katherine hoped to start her own goodnight kiss tradition with him, and this night, for once, there was nothing and no one to stop her.

She quietly knocked on his door, but there was no response. She let herself in anyway. "Alan? Brother? Big Hat Rack Brother? You awake?" She walked to his bed and lightly shook his shoulder.

He rolled over and rubbed his eyes. Before him, in the dim light that came through his window, he saw his naked sister. "I am now. What is it?"

"I was thinking. You and Mom have such fun with your nightly kisses. Couldn't you and I start our own goodnight kiss tradition? It's not like she could complain about that, now." She sat down at the foot of his bed and began to gently caress his upper thigh absent-mindedly through the covers.

"I'd like that, Supremely Suckable Smaller Sister, except for one thing. You always want to go further. I don't want to be sister-raped every night before I go to bed."

She rolled her eyes. "Brother, Brother, Brother. And I used to think you were so smart. You act like having your sister rape you is some kind of bad thing." She giggled. "But okay, I promise I'll be mellow. Just kissing." After a pause, she added significantly, "This time." She winked.

He smiled at that, and said, "Tell that to Mom. I'm sure she thought a goodnight kiss was actually just a goodnight kiss at some point. Maybe the first or second time. You should have seen the way she was aggressively all over me just now."

Katherine inched forward and smiled seductively. "Oooh! Is that an invitation to watch next time? Or are you just referring to setting up video cameras for later viewing?" She giggled.

He rolled his eyes. "Neither, my beautiful sister. This is what I mean. You've got to keep it cool."

"I promise I'll let you lead the way. Imagine my hands are made of lead. They won't leave my side."

He realized, Once this tradition gets started, it's gonna be expected every night without fail, just like with Mom now. Most nights, by the time I'm ready to go to bed, I am soooo totally dead. My dick is usually so sore that it's about to fall off. Then Mom wrings whatever little sexual energy I have left out of me with her "goodnight kiss," and I zonk out like a dead man. Of course, it's all so pleasurable that I can't really complain. Dang, Mom has become a total expert on sucking cock, that's for sure!

But, on the other hand, I really owe it to Sis. I've been so focused on Mom and neglecting my sister, like with these goodnight kisses and tuck ins, which really should be called goodnight tuck and sucks. I love Sis, so very, very much! Of course I'd love a goodnight kiss from her every night. But I just can't deal with the energy of so many women. Let's do this, but in a way so it doesn't get locked in as a tradition already.

He sat up in bed and held her face with his hands. He drew her in close, as if to kiss her.

Katherine smiled in anticipation with her large puppy dog eyes. Despite all they'd done to each other, her heart was pounding hard simply from the prospect of sharing an intimate kiss.

He was eager to kiss her too. But first, he said, "Okay, Sis. Let's face facts and be realistic. I predict that regardless of what happens with this psychologist visit tomorrow, I'm gonna be fucking Mom sooner or later. Probably sooner. Mom may not realize it yet, but it's obvious that her resistance to that is weakening by the day. When that happens, there won't be any need to keep the fact that you and I are fucking a secret any longer. So I imagine that some nights, I'll be sleeping with you, and some nights I'll be sleeping with her. Who knows? Maybe we'll all be sleeping together sometimes."

Katherine briefly raised a fist in triumph. "Yes! Excellent! God I've been waiting soooo long for that, Bro. So friggin' long. Do you know how many damn nights I've waited for you to come into my bedroom and fuck me? Let's just call it A LOT!" She giggled. "Even though I know you're not going to be with Mom down the hall, or me, the idea that you COULD makes it hard to sleep. You could!"

He said, "Wait. You mentioned me sneaking into your room or Mom's room. Do both those things arouse you?"

"Of course! I'm sure it's hard for you to understand the fuck toy mentality. When I think of you with someone like Mom, I get super jealous, but super turned on too! I love that we're both totally helpless, sleeping so close to your room. You could sneak in any time and wake me after slipping your cock deep inside my pussy! And you could do the same to Mom! Isn't that HOT?"

He chuckled. "Well, yeah. For me."

"For me too! I want to hold you at night. All night. So bad! It's been so incredibly long since we've really been together. I miss the feeling of having you inside me so much!"

He continued to hold and caress her face. "Me too. But the point is, the whole idea of the goodnight kiss is probably gonna change. So let's not fix any tradition in stone just yet, okay? Let's just enjoy a casual goodnight kiss now and see how this all shakes out, tomorrow with this Xania woman, and beyond."

"Yeay! Goodnight kiss! Goodnight kiss! Kiss me, Big Boinking Buxom Bouncing Birds Brother!" She hugged him tight, her joy infectiously spreading to him. She pulled back and puckered her lips expectantly.

Alan couldn't help but smile. "You're really into the B alliteration thing lately, aren't you, Little Svelte Sexy Siren Succubus Sister?" He rubbed his nose against hers adoringly.

She giggled at that and then grabbed him. They went at it.

He tried to keep up with his sister's enthusiasm, but that was hard to do.

She was a great kisser and let him know that fact over and over again. But she kept her promise and kept her arms by her sides.

Alan went to bed very satisfied, feeling profoundly loved by his sister and mother in equal measure.

Alan woke up in the middle of the night, around midnight. As he lay there in deep thought, he felt bad about refusing his mother a cum load during her goodnight kiss.

He thought, A lot of people are counting on me. I know it's tough, constantly pushing what I can do physically, but Mom really needs me. I didn't cum for her at all today except for the one time. And sneaking past her to take a nap was childish. She was so bummed. She's so worried, I wonder whether she'll even be able to sleep tonight. I not only have all these rewards, I also have a responsibility to keep the women who love me pleased. I should really go in there and give her what she needs. With a few hours of sleep under my belt, I've recovered enough to handle it and enjoy it.

Still flushed with his recent sexual successes, he got up and walked into his mother's bedroom. The last time he'd done this, he wore pajamas and knocked politely on her door. But this time he came in nude and just let himself in. She lay asleep with the covers off of the top half of her body.

Alan was tempted to grab her big boobs and wake her up in some aggressive way. Maybe I should wake her up sitting on her face with my dick in her mouth. That would feel good! But at heart he was very well mannered, so he pushed such thoughts out of his head. Who am I kidding? How could I think that, when she looks so beautiful and peaceful, just lying there?

He leaned down and tapped her on the shoulder. "Mom, wake up."

Susan's eyes fluttered open with surprise as she came out of her slumber. "What is it? Who's there?" she said groggily as she rolled over in bed.

"It's me - Alan."

Her eyes quickly adjusted to the darkness. She saw him standing there, naked and with a hard-on. She immediately sat up in bed and looked at him with blurred vision, since her glasses weren't within reach. "Alan, we can't," she said firmly, though sadly.

Alan could tell that, for some reason, she thought he'd come to fuck her. "Mom, I'm not here about that. I'm just here because I have a raging hard-on and I know how much you hate it if I masturbate myself. You told me I should wake you up at any time, so here I am."

It took her a bit to register that, and then wake up more fully. She looked worried and felt vulnerable, still uncertain if he had finally gotten aggressive enough to come and have sex with her.

But he just stood there and politely waited for her.

She looked down at his stiff erection, which twitched and poked towards her, and finally said, "Oh. I see... Hmmm. Well, I guess I'd better take care of it then. Why don't you kneel over by the side of the bed here and I'll suck it for you."

"Thanks, Mom, you're the best." He thought, She said that just like when I was a little kid and I'd come home with a bloody cut and she'd offer to put a band-aid on it. I don't know why, but her motherly, helpful tone is such a turn-on!

He also thought, As beautiful as Mom is, she's even more beautiful with her glasses off. Dang, she is something else.

Susan rubbed the bleariness out of her eyes and grabbed a hold of his erection as he knelt down by the edge of the bed where she sat up. A big, contented smile crossed her face as she began to rub it. She said, "You're such a thoughtful son. I went to bed dissatisfied, but now you're making up for it. What a nice little surprise midnight snack you've given me... Or should I say, a nice big snack! Soooo big..."

Alan noticed she wore a nightie that hung halfway down her stomach, and asked, "By the way, Mom, why aren't you sleeping naked? I thought you love being naked these days."

"Yes, that's true, but I'm naked so often nowadays that I'm afraid over time my boobs will lose support and start to sag. I'm not a teenager anymore, you know. So Suzanne and I have both started to wear these types of tops to bed. They keep my boobs firm and high for you, and the rest of me gets to stay naked."

This latest turn of conversation put her more at ease, and she thought, What was I thinking? Tiger would never take advantage of me; he's not that kind of guy. He's a good boy!

She also began to feel more frisky, as the delightful prospect of more cocksucking fully registered with her brain. She pulled down her blankets with her free hand and said, "See? I only wear this little top. That way there's nothing down below to stop me from masturbating. And believe me, I masturbate all the time, thinking only of you. A couple of times every day, at the very least."

Her hand caressed the top as she mentioned it, and then her hand drifted down her stomach. She petted her bush briefly and licked her lips seductively as she looked directly into his eyes. But then she focused on the cocksucking request.

She turned around in bed to face him and kicked her covers all the way off. She put her face down by the edge of the bed and stuck her ass high up in the air. She knew that he loved to see her naked ass wiggle while she sucked him off.

After a few minutes, he reached across her back and inserted a finger into her anus. (He'd thoroughly licked the finger first, to make sure it at least had some lubrication.) He'd done this many times before, but for the past few days she'd been terribly excited by anal sex fantasies, so his fingering really set her off this time.

She thought, Tiger is getting my ass ready! He's probing and widening my tightest hole so he can eventually insert that monster tree trunk of his into my ass! Shove it in, Tiger! Not just one finger, but two! Ream your mommy! Yes!

She got so aroused by the anal intrusion that her whole ass shook as if it was a blender on a high setting.

That was too exciting for Alan, and he gave up his load without much struggle. He filled her mouth with a healthy helping of cum, though it still wasn't up to his usual number of ropes.

Susan was fully into it now, and she eagerly drank down each new squirt as he came in her mouth.

After she got him off (and got off herself), she remained lying face down on her bed with her ass up in the air.

He walked around the bed to get a direct view of her rear side.

Seeing his attention focused there, she pushed her ass up even higher, hoping that he might take the hint that her ass was his for the taking, even if her pussy wasn't. To goad him on (and arouse herself in the process), she said, "How is it I always find myself in these kinds of humiliating positions? It seems like you're going to have your way with your helpless mommy yet again!"

Alan, however, was only human, and knew he'd be unable to get erect again anytime soon. He stared at her ass, and thought, It is completely unreal that I am not fucking this woman already. But I've sworn that I'm not going to do it until she agrees first. I am not going to force myself on my own loving mother!

She remained perched up like that for a minute or two, but with no better reaction than a hand of his that softly caressed her ass, with a pouty "Oh, poo!" she gave up and sat up to face him.

He said, "Mom, do you think it would be all right if I just spent the rest of the night here with you? It's such a big bed. And if I have my particular problem again, you can be right here."

She wiped away a small droplet of her son's cream dribbling down her chin, and considered the tempting idea. She remembered her concerns and her desire to see a psychologist. With a start she realized that the meeting would be in the morning, just hours away. She knew that if they slept together, odds were good they would almost certainly end up fucking before the night was over.

So she reluctantly said, "No Tiger. I'd like that, but we can't. Not tonight. For one thing, I've been tossing and turning most of the night and I need to sleep. Secondly, I might just roll on top of you in my sleep and who knows what might happen? Since your pole is almost always erect, I could easily get my pussy impaled on your cock and you might accidentally pump a hot load of sticky cum into mommy's cunt before either of us are fully aware. Or what if, in your sleep, you roll on top and sleep-fuck me, pumping in and out, and in and out, in and out, right into your dear old mother?"

Alan was so sexually frustrated that he felt ready to crack his head open with a hammer, but he stayed quiet. It didn't help that she appeared utterly delighted by the idea that she nonetheless dismissed. She killed him with mixed signals.

She continued, in a calmer tone, "Now I can rest easy, with the wonderful taste of your cum in my mouth. Today's been a good day after all, thanks to you. So please go back to bed. If you get another hard-on, just come to mommy and I'll make it all better. But you can't sleep here. Not yet, at least."

Alan nodded glumly.

He thought they were done and it was time for him to return to his room, but he wasn't quite right.

Susan's face lit up as she thought of something. "Wait! Don't go. Not yet. I almost forgot to give you a good cleaning."

"Mom, you don't have to do that," he protested, but his protest was feeble.

"Nonsense." She was determined to leave him with a clean penis and balls, just as she was determined to make sure he went to school with clean clothes each morning. But she made quick work of it, because they were both sleepy.

Finally, Alan went back to his room. For just the briefest of moments, he'd half expected to have his deepest fantasy finally fulfilled, but to no avail. He wasn't terribly worried about turning back the clock through the psychologist's visit or anything else; he knew he'd always have a very active sex life from now on. The thing that most worried him was that his mother would remain resolute about not wanting to fuck. A family friend once told him that his father did everything short of fucking his mother for literally years before they finally got married.

He thought, There's no way I could handle that. True, it's only been a few weeks of this "so close but still so far" denial, but I can't live on the edge like this for much longer. I'm gonna have to do to my mother what I did to Glory today, sooner or later. Okay, sooner. But I have to hold out long enough at least to respect her wishes on this psychologist visit thing.

He consoled himself with her "You can't sleep here. Not yet, at least," comment. She knows it's going to happen eventually. She just wants to feel completely good about it. She's got a few remaining hang-ups she has to get rid of first, that's all. Maybe the psychologist could actually help with that. I just hope something happens soon!

Susan went to sleep, proud that she hadn't given in to the ultimate temptation. Before she drifted off, she had a very hot masturbatory session and imagined her son raping her in the middle of the night. In the dream, he was the opposite of how he was in real life. He was rude, aggressive, cold hearted, and wicked. He tied her to the bed and cackled gleefully as he fucked her.

When she woke in the middle of the night, she wondered why she liked him more that way and if her constant teasing behavior was slowly bringing that side out of him. If she'd known how he treated Glory earlier in the day, or that the dreams he had that night were very similar to her own fantasies, it would have fueled many masturbatory sessions that could have quite possibly broken down her will to resist temptation completely.

She was true to her word though: despite her anxiousness, she had no trouble getting back to sleep, content with the knowledge that Alan loved her and took care of her.