6 Times a Day

397 Alan with Mom. [DD Sponsored]

Drunk Dargon Special [ 4 / 5 ] Extra Long Chapter 5K words

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By the time Alan finished his essay, it was already eleven o'clock. He figured that crashing immediately wouldn't give him nearly as much sleep as he needed, given his exhausted state, but at least it wasn't a total disaster. He had half a mind to just drop his head on his pillow and fall asleep before doing any of his nightly rituals, like brushing his teeth. But there was one new ritual he didn't want to miss out on: his good-night kiss and "tuck-in" from his mother. He wandered down the hallway to his mother's room and told her he was going to bed.

Susan had been waiting up for him. She was wearing an old-fashioned, frilly robe and was knitting Katherine a sweater. She looked very much like a granny in the dim light, staring at her knitting needles through her glasses. She said quietly, "I'll be there in a minute, Tiger."

He returned to his room and lay on his bed. He could barely keep his eyes open.

Then Susan came in, and his eyes opened wide.

Her appearance was totally transformed. The granny robe was gone; it had been replaced by yet another newly-purchased, semi-transparent nightie that dramatically showed off her incredible G-cup breasts. She looked like a twenty-two-year-old sex goddess. She acted like one too, and didn't waste any time.

She was all smiles as she said, "Oh dear, Tiger. You look like something the cat dragged in. I'll bet your powerful, demanding cock isn't even half-hard, and that's just not right!"

She dipped and swayed her way across his room, then pulled his covers down and looked at his flaccid penis. "Oh my goodness. I was right. My Tiger, not rock hard? I hardly know what to do with myself. Looks like you need some visual stimulation, don't you think? I just can't give you your goodnight kiss until I know you're hard for me."

"Mom, I'd really appreciate that. Today just hasn't been a good day, all around. It's had its good moments, but I've been in kind of a weary funk. If you can get it up, it'll be a pretty amazing feat."

"I can't bear to stand here and do nothing while my son is in a weary funk. I guess I'll just have to get naked and strut around like a naughty big-titted trollop, and then suck his cock until he feels all better. That's what the best, most loving mommies do."

Alan was amazed at how quickly she'd transformed herself. A few minutes earlier she'd appeared to be completely sexless, or at least as sexless as someone with movie star looks could be. Now she was acting as if she were a professional whore who was waiting to fuck, yet at the same time she never lost her kind, motherly demeanor. The main thing was that she was filled with a pure love and joy for sexually pleasuring him, and that kind of enthusiasm was impossible to resist.

She didn't do a striptease. Instead, she took her clothes off in a flash (not that it was hard to do, since she wore only the one-piece nightie), and then got down to some serious, fully-nude teasing.

She stretched and preened in every possible way. It was almost as if she were doing naked warm-up exercises for him. She thought, So SHAMEFUL! I'm acting like the worst kind of wanton harlot, like I'm one of the shameless hussies my mother warned me about! But if feels so GOOD! I've never felt this ALIVE! Tiger's cock is already starting to engorge. In a couple of minutes that thick slab of manly might will be in my mouth, and then my joy and arousal will be never-ending!

Indeed, Alan's dick was growing stiff as he watched her. As her cheeks reddened, he thought, I must be sick, but I get totally turned on watching Mom blush and get all embarrassed. It's like she gets so hot for me that she's totally incapable of controlling herself. That's passion! And she's somehow so innocent, yet so slutty! My God! And her body! So perfect in every way! UNGH!

She continued to preen and pose. She made a particular emphasis of thrusting her chest out at every opportunity. She pulled a leg up over her head. She stood up, touched her toes, then backed up until her ass was literally in his face. Half the time she looked like she was in the throes of orgasm, almost as if she were being fucked by an invisible man.

After a minute of this, she started speaking as she continued to pose for him. Her voice was calm at first. "Son, you know I work out diligently with Suzanne every morning. I've done it for years and years, but only because she insisted. It helped fill my empty days while you and Angel were at school. But now I'm so happy I did, because it means I have all of this to share with you!" She ran her hands sensuously down her sides. "Now I work out twice as diligently as before. I want to have the PERFECT BODY so I can serve you better!"

The lusty enthusiasm in her voice rose steadily. "I think about my hands running over you, and your hands running over me! Do you want to touch me? Do you want to make use of your centerfold mommy?" She cupped her giant tits from underneath and squeezed them together, like she was ready for a titfuck. "Use me as you see fit!"

But when she said "Use me as you see fit," she took it for granted that her permission didn't include her pussy. And while she flaunted her body, she tried not to make her pussy the center of attention. She didn't want Alan to be thinking about that area and thus thinking about fucking her. She aspired only to be his favorite cocksucker, and tried to push all other desires involving her hungry and needy vagina out of her mind. But he still got to see her pussy most of the time anyway, since she was completely nude, and her obvious efforts to hide it made it that much more fun when he could see it clearly.

She kept glancing at his dick. It took a while - he really was wiped out! - but it finally fully engorged. Her mouth salivated and her heart pounded hard. She crawled up on his bed until her mouth was inches from his ear. Then she whispered in a sexy purr, "This is the body of a personal cocksucker, dedicated to constantly serving you and your cock!" She picked up one of his hands, brought it to her cleavage, and trapped it between her tits. "Another one of your personal cocksuckers, a wise busty bombshell named Suzanne, once told me that cocksucking is not merely done with the mouth, or even just the mouth and the hands. It takes the whole body!"

She started churning her hips, causing his hand to slide in between her massive melons. "Son, when I'm happily humming on your fat log of a cock, I can feel it in my nipples. So much! I can even feel it down in my toes!"

He realized, I guess there's some truth to what Aims said earlier. I don't think she or Sis can compare with Mom or Aunt Suzy when it comes to getting me hard. It's not that they aren't super sexy too, but there's just something a bit extra with my mom and aunt. Maybe it's Aunt Suzy's experience that comes with her age? Maybe it's the taboo with Mom? Maybe it's that they're both so fucking voluptuous, and with kinky passions to match!

Susan finally reached into Alan's lap and felt about for his dick, as if she couldn't see it perfectly well. "Hmmm." she said uncertainly. "It's starting to feel a bit hard. It'll probably just take a couple more minutes of intense stimulation to reach full strength."

He cried out in agitation, "MooooOOOOoooom! What do you mean? It's as stiff as a board!"

She smiled at him, and then he realized that she just wanted to play some more first. "Tiger, I don't expect mere hardness. Not from my stud son. I expect it to be throbbing and hot to the touch. I expect it to pound through steel! Since I'm obviously not exciting you..."

He interrupted again, although with more amusement this time. "Mom!"

She winked. "Since I'm obviously not exciting you enough, perhaps I need to talk dirty at the same time." She resumed her sexy contortions. "Did you know I got a phone call from Brenda today?"

"You did? What did she say?"

"Hey, none of that." Susan was referring to the fact that he was starting to stroke himself. "I never want to see you do that ever again. You've got too many big-titted hotties eager to help. No more Sin of Onan!"

He stopped, then pinned his hands under his ass. He realized she had a very good point.

She stared lustily at his thick erection as it poked up into the air while repeatedly licking her lips. "Leave your slick fuck stick to me in a minute, because I can't talk and... Oh, dammit, I can't help myself! I can at least lick it while I talk, can't I?!"

She sighed with blissful relief as she wrapped a hand around his shaft and started stroking. She repositioned herself, and got busy lapping against his sweet spot. "Mmmm! Oh yesssss! That hits the spot. Literally!" She giggled, and then repeatedly flicked her tongue at his sweet spot to show her originally-unintended double meaning.

With one hand pumping up and down his shaft and her mouth alternately blowing on his cockhead or tickling it with the tip of her tongue, she tried to get back to her account of the phone call from Brenda. "Anyway, she was very happy. She appears to have remembered quite a lot of what happened yesterday. More importantly, she seems to understand what a total sexual stud you are. My son! She totally wants you. Carnally. Biblically!"

Hearing that sent a shiver down his spine. My God! BRENDA?! She's so sexy, not to mention stacked! His gaze went to his mother's twin globes, which were lightly swaying in time to her stroking. I still can't believe her tits are even bigger than Mom's! That's crazy. I'm just a teenage nobody. What does she want with me?!

He forced himself to calm down, and asked, "Were you nice to her?"

"The nicest! I really tried my best. I thought about what you told me last night, and that helped. Suzanne also talked to me today about the need to be nice to her. She reminded me that your powerful cock demands many different helpers. It demands variety!"

He thought, I seriously gotta thank Aunt Suzy! I love these notions that she's putting into Mom's head!

She continued, "Anyway, Brenda and I talked about why you wouldn't let her suck you off, and why she wasn't yet worthy of your cum. She's going to try harder to please you next time so you'll be more likely to let her suck it."

That thought thrilled him but he tried hard not to show it. He asked, "What did you think about that?"

"I was in favor! I even hinted that you'd paint her face with spermy goodness if she blew you really well. Would you do that for her? For me? She told me how much she loved seeing my spermy face last night and she can't wait for you to splooge all over her too! She really wants to be another one of your personal cocksuckers!"

"No way!" Another thrill ran through him, tingling him down to his toes.

Susan would have said "Yes way!" except that she'd just engulfed Alan's cockhead and was busy bobbing down to his sweet spot. She kept at it for a wonderfully pleasurable minute or two.

He squirmed in bed, trying hard to cope with the arousal without cumming.

Just when he was sure she was done talking, she pulled off to say, "She's coming along quickly. She's beginning to understand her role in life, which is to be a big-titted cocksucker just for you. One of many! Do you like that?"

"Mom, come on! You know it turns me on. But she didn't really say all that, did she?"

"Okay, maybe she didn't. I really did talk to her on the phone, though. And she was thinking it. I could tell. Her voice was practically oozing desire. And we really did talk about some of this stuff."

"What stuff?!" Between the talk and Susan's oral work, he felt like his heart was going to burst through his chest.

"Never you mind." She lifted her head and winked at him, and then got back to licking his sweet spot. "The key thing is that she said she wants to come back soon, and she promised to wear something sexy, just for you."

He thought, That part probably is true. But I'll bet the rest of her description is mostly just wild exaggeration. I mean, it's not like she'd actually discuss being one of my personal cocksuckers, would she? She's gorgeous AND really rich. She can have anyone she wants! He felt a bit disappointed, but he had to admit to himself that at least the call hinted at positive progress.

Susan went on, "But Son, I'm concerned. Are her tits really that great? Don't you like mine?" Even though he'd praised her tits the night before, she still wanted more reassurance.

In fact, she was so keen on getting good feedback from him that she stopped her licking and stroking and repositioned herself up his body. She thrust her chest out again and pushed her breasts right into his face, smothering him with her titty goodness. Then she rubbed one of her nipples in circles around one of his cheeks. "Aren't your mother's 38Gs good enough for you?"

He was relieved that one of her hands dropped into his lap and resumed stroking his shaft while she waited for an answer. He loved licking her soft tit-flesh, but he was also greatly enjoying what she was doing to his boner. He licked a nipple instead of answering.

She actually felt alarmed at how good it felt when he did that. She worried she'd lose what little self-control she still had if she let him suck on her nipples. So she lifted her chest until his forehead was encased in tit flesh.

That enabled him to speak with an unobstructed mouth while enjoying the depths of her cleavage. "Mom, you know I love you. You have THE perfect body. I even love your glasses; they make you look more intellectual and sexy, like a naughty professor. Your legs, your ass, hell, your back. Your earlobes. They're all so glorious. And your tits are perfection too. It's like I told you: Brenda could never compete with you for my love. No one can. You have a special place in my heart!"

"Oh, Tiger! You say the sweetest things. No wonder Suzanne calls you 'Sweetie.' You ARE such a sweetie. I'd like to see Brenda turn you on, because you deserve more cocksuckers of her caliber. There's nothing you should be denied. But only so long as you don't want her more than me. If that happens, I'll go on the warpath."

"Don't worry, Mom. You're number one. You and Aunt Suzy. You two will always be tops with me, forever!"

She laughed, even as she jacked him off with more intensity. "Tied for number one. Well, I guess that's better than before, when I was clearly behind your auntie as your go-to cocksucker. And I've got Angel chasing close behind. Plus who knows who else from school, if your daily cum chart is anything to go by. Looks like I'll just have to do an even better job of constantly draining your balls dry - better than ever before!"

She stopped talking and took him back into her mouth. At the same time, she squeezed his balls and even sawed a finger into his anus, using her pussy juices as lubrication. It was an all-out erotic assault.

She thought, MMMM! This is so humiliating! I'm bobbing and licking his cock non-stop, like I can't get enough of it. And I can't! Yet, at the same time, I'm promoting Brenda to be another one of his personal cocksuckers. That's messed up. But somehow, it makes me even hotter for him! If Tiger has an entire stable of big-titted babes constantly servicing his cock, than what chance to do I have of resisting him? NONE, that's what! Mmmm! Which means that... Mmmm... Every day... my mouth is going to be crammed full of hot cock, like it is right now! MMMM!

She employed her favorite moves, including the corkscrew and reverse corkscrew, to bring him right to the brink of orgasm. He clutched at his sheets with sweat actually trickling down his forehead.

But that turned out to be merely the warm-up to put him in the mood for what she really wanted to do. She pulled her mouth off his wet dick, and said, "I was just getting reacquainted with my favorite little cocky feller. Now I want to talk to you about something very important."

Alan's erection softened a bit as he braced himself for some kind of lecture or serious discussion.

But then she said, while her fingers kept sliding up and down his pole, "The other day, Suzanne was telling me about the latest fun she'd had with you. Do you know how we like to tell each other everything we do to you, every last lick, every last suck, down to the very last drop of sperm we lick off your balls, so we can relive it all over again while we wait for you to come home from school?"

"Well, no, actually. Do you really do that?" He had some idea that they talked about many things during the day, and especially during their morning workouts, but he had no clue that they were that explicit and that detailed when it came to sex.

"Yes! In the last few days we've started being totally sexually graphic and honest, usually while we're doing our morning exercises together. It's great! I tried to hide my cock lust for a long time, but now that I don't we have such fun! Anyhow, we were doing that when she casually started talking to me about titfucking. I had to say to her, 'Whoa! Titfucking? What's that?'"

"Come on, Mom. You MUST have known what that is."

"Well, I did, but not for real, if you know what I mean. What I mean is, I'd heard of it somehow, but I thought it was just a weird thing done for show only. Real people wouldn't actually do that for pleasure."

That was mostly true. She'd learned more about titfucking the last few days, thanks to the erotic story that Suzanne had had her read, but she didn't want to admit to him that she was reading such "wicked" things. Her belief system was going through a sea change, and it was full of contradictions.

She added, "To make a long story short, Suzanne told me all about it. She made it sound as pleasurable as cocksucking, if you can imagine that!" With that reminder, she nibbled on the tip of his cockhead some more, sucking and kissing only the top inch or two.

"I can," he replied with some amusement, not to mention growing anticipation. "And it is. At least for me."

Susan's whole face lit up and her body tingled with visible excitement. "Then it's true?! It's really true?!"

"Sure, Mom. How could you not know about something like that? It's like not knowing about handjobs or blowjobs."

"I'm sorry, Son. I've just been so sheltered. Believe it or not, it wasn't that many weeks ago that I barely even knew about those two things. I knew about them intellectually, I guess, but they seemed like completely impossible, crazy things no normal person would ever do."

Susan continued, "Even after Suzanne told me about it, I could scarcely believe that such a wonderful thing exists. I was going to try it out with you last night, but then I got so carried away with your blowjob that I forgot all about it. You know how I can get carried away, especially when it comes to knob gobbling." She laughed, since that was a term that Suzanne had recently taught her and she really liked it.

"Mmmm! Speaking of which..." She crammed his cockhead in her mouth and got busy bobbing again.

Alan knew that she didn't know the full story. He remembered Suzanne telling him some days ago that she was deliberately avoiding the mention of other sex acts like titfucking until Susan was fully committed to cocksucking without any more moralistic backsliding on that. The fact that Suzanne deemed it time to clue Susan in to titfucking implied a lot of progress with his mother.

He was enjoying her oral attentions, but a titfuck from her sounded like a dream come true, so he suggested gladly, "Well, you did it to me a little bit this morning, although that was only like half a minute. What did you think of that?"

"MMMM!" She helplessly waved her hands in the air, trying to indicate that she was in no condition to talk. If she had been able to speak, she would have said that it had been too brief for her to get much of opinion on it, especially since he was moments from cumming when she started.

He suggested, "We didn't have time then to do it properly. But we've got lots of time now. So I say let's try it out for real, a nice prolonged titfuck together."

She quickly removed her lips. "YES! LET'S!" She playfully kissed his sweet spot.

He had to laugh, because she was practically lost in orgasmic la-la-land already, just from thinking about the prospect of how good a titfuck might be.

She found herself licking his sweet spot some more, but she forced herself to stop. Squirming with excitement, she said, "Let's get in position. How do we do this?"

"Here. Let me help." He grabbed her left tit with one hand and her right ass cheek with the other. He spent about a minute just fondling her body until she started to wise up to the fact that he wasn't getting her in position.

He actually had been stalling for time to give his penis a chance to recover, since her all-out oral attack a couple of minutes earlier had brought him so close to the edge. In addition, it was just plain fun to play with her perfect, naked body, especially when it was wriggling all over his own.

Just as his fingers were starting to probe around her pussy lips, she complained, "Tiiiiiiiger! Please don't torture me. I'm dying for you to fuck my tits! Besides, you're getting dangerously close to the forbidden zone."

He thought, Man, I could never have imagined in my wildest dreams I'd hear my prudish mom say that! Life is good! Then a curious thought came to him. "Hey. Why is it you're ready for a titfucking, but you usually say it's against the rules for me to play with your tits?"

She was startled and embarrassed to have that contradiction pointed out. But she'd given it some thought, so she said, "I know that may seem strange, but this is all about pleasuring your cock. Remember, you have a serious medical need that has to be taken care of every single day. If titfucking is a viable alternative to handjobs and blowjobs, I need to give it a try. After all, there will be many times I've sucked you so long that my mouth will be too tired to go on."

He asked, "But why is there still a problem about me touching your wonderful tits?" Even as he said that, he brought his hands back to them and caressed them from below.

She shivered visibly. "THAT's the problem! You see how much what your fingers are doing affects me? Look. I understand that as your big-titted sex-pet mommy, there will be times you want to play with my tits. That's only fair and right. But sometimes it makes me TOO horny! I lose all control! Especially when you play with my nipples?"

"Like this?" With a big grin, he rolled her nipples between his fingers.

"UGH! HNNNG! Exactly like that!" Her tremendous G-cups heaved up and down as she struggled to breathe. "Please! Stop!"

He relented and went back to just caressing their sensitive undersides.

Once she had her breathing under control, she said, "So that's why we have to have that rule. This is about YOUR pleasure, not my pleasure. Luckily, titfucking doesn't seem to involve the nipples much, so I think we'll be okay."

He complained, "But Mom, I want you to feel pleasure too, and lots of it! What's wrong with that?!"

She frowned. "Let's not talk about that, okay? If it's not all about helping you and your medical problem, then the morality of what we're doing changes."

He decided to let the issue drop for the moment. He figured her attitude would slowly change over time, the more she got hooked on their sexy fun times together.

He was glad that the discussion was giving his penis a much-needed break. He finally decided he was ready for more, so he said as he swiped a finger through her wet inner thighs, "Looks like YOU'RE ready. Let's see... Why don't I sit on the edge of the bed and you can kneel between my knees?"

She glowed with happiness, thanks to the prospect of kneeling naked between his legs. "Yes! It's just like Suzanne said! She told me that being an obedient titfucker is just like being an obedient cocksucker! The proper position is naked and on my knees, worshipping your big cock as it dangles in front of my nose!"

He was surprised. That sounded a bit extreme for Suzanne, even given her obvious recent effort at sexual indoctrination. "Did Aunt Suzy really say that?"

Susan's lingering blush reddened a little more as she repositioned on the floor. "No, not exactly," she admitted. "I embellished it a little. But I'm just so excited! Let's do it! Shove your big thing into my cleavage! Please! It's what my tits were made for!"

He scooted into position too, and then he did just that. He sighed with contentment as she pressed her tits snugly around his shaft, encasing him in a tunnel of soft tit-flesh. He remembered how sleepy he'd been when she'd first come in. That was long gone; he was now totally wired with energy and lust.

But then she paused, frowning. Worse, she pulled back, forcing his dick to lose contact with her ripe body.

Impatient to feel the joy, he asked, "What?"

"Well, it's just... When it comes right down to it, this is just so dreadfully sinfully naughty. If my parents could see me now, or my sister... Oh dear!"

Oh man! She can't be serious! Now? She has doubts now?! He said, "But they're not here. Don't worry about it." He scooted forward, drawing his erection to within inches of her chest again.

She looked even more indecisive, keeping her cleavage frustratingly out of reach. "But still..."

He thought, What a fine time for Mom to have a prude attack! She totally wants it, we both know that, but it seems she needs a little push. He said, "You know Aunt Suzy would totally approve. And Nurse Akami thinks it's great for the chafing problem."

"I know, I know, but somehow the image of my parents looking at me popped into my head and I just can't get it out." She covered her breasts, as if her parents were staring at her nakedness from somewhere in the room.

Alan was stumped. He knew this was the time for his cleverness to shine through, but he was too horny to think straight.

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