6 Times a Day

'Someone' Special [ 8 / 12 ] 6K words

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When Alan woke, he felt much better. His penis hadn't gotten as much activity as usual since the morning before, and it felt great. The soreness that had bothered him in the morning was long gone. He hit the books and studied well until dinner.

Actually, he mostly studied well, but faced a steady stream of interruptions. All four females repeatedly wandered in and out of his room, each one trying to act like Florence Nightingale. He found it especially endearing to see how doting the usually hard-nosed Suzanne was.

Most of the women merely peeked in to check on him without disturbing his studies. But Amy seemed not to understand that consideration. She eventually came in, wearing a short pink dress, and sat right on his lap. "Hey, Beau! What's up?"

He wrapped an arm around her, but said, "Not much. But as you can see, I'm trying to study here."

She wrapped an arm around him too, and snuggled up close. "I know that, silly. But you need to chill out from time to time, am I right? You've been working hard for a while. Besides, I wanted to ask you something about Christine."

"Oh really? What's that?"

"I'm curious how come you haven't gone to the beach with Christine again, or some other fun after school thing like that."

His heart started to beat fast as he recalled Christine in her sexy blue bathing suit. But he tried to play it cool, and just said, "We do stuff. She's a good friend. We'll probably go on another practice date soon."

Amy could feel Alan's penis engorging, because she was sitting directly on it. But she didn't react to it yet. "Yeah, but don't you want to want to see her in a super sexy bikini?"

He asked suspiciously, "What's it to you? And what do you think of my friendship with Christine, anyway?"

She started to reply, "Hmmm. That's an interesting question." She finally visibly noticed his erection, by squirming and bouncing on it a little bit. "Hey, what do we have here?! The Christine Effect!"

"The what?"

"Oh, don't worry about that. It's just kind of a thing I noticed. Anyhoo, what do I think of you and Christine? Hmmm..."

"Hey!" He noticed that Amy had just repositioned herself, and then reached into his shorts and started stroking his erection. "What are you doing?"

She giggled. "What does it look like? Geez Louise! I'd totally think you'd know by now. It's called a handjob!" She giggled some more as her fingers slid up and down his stiff pole.

He sighed. "I know that! What I mean is, WHY are you doing it?"

"Well, isn't that totally what we're supposed to do when your thingy gets all bonerrific like this? Besides, who says you can't study AND get some stealthy help? Wouldn't that be more fun?"

He sighed again, but thought, Hell, why not? I must admit it feels pretty damn good. "Well... I suppose we can give it a try..."

"Yeay! Cool beans! You're gonna love this, I promise!" She suddenly got off his lap and knelt down between his legs.

He muttered, "I'm sure I'm gonna love it. That's not the problem. Will I actually be able to study though?!"

Amy had been in the middle of taking her top off, but she changed her mind and pulled it back down. She resumed jacking him off instead. "Don't worry. You totally won't notice I'm here. I won't say a word, I promise. I'll even keep my clothes on, and you know how much that bugs me."

Due to Amy's promise to stay silent, he never did get an answer about what she thought about his evolving relationship with Christine. He was too distracted by her "stealthy" help to remember to ask.

Amy soon repositioned again. Alan had a desk that curved from where his computer was and stuck out into his room. She bent down under the desk so she could not only fondle, but also breathe on his penis. Plus, she was in position to give him a blowjob at a moment's notice if given permission.

She tended to get carried away, and periodically he had to remind her not to lick as well.

That put Amy's ass in a very visible position for anyone walking into the room. Even he could see some of her bare, round rump sticking out from under the desk from where he sat.

As he did his algebra homework with Amy lightly blowing on and fondling his erection, Katherine walked in. She casually flipped up Amy's skirt and fondled her friend's exposed pussy the whole time she talked to her brother.

When she left, she kept the skirt that way, so that other visitors could also enjoy the excellent ass.

Susan chuckled when she came in and saw how Amy's ass hung there. She said, "Oh, goody! Tiger, you've agreed to the stealth help. I'm so pleased. Amy, I can't see what you're doing, but I don't hear any slurpy sounds. Are you only using your hands?"

Amy whispered, "I'm not allowed to talk!"

Susan said, "I'm sure it's okay to talk to me, for just a minute. Right, Tiger?"

"Right," he said.

So Amy whispered, "Just hands. Well, I'm kind of licking him a little bit sometimes, but not much. I don't want to distract him from his work."

Susan said, "Good. We'll take turns about every half hour or so, to make sure nobody gets too tired. Amy, please remember to do a good job on his big cock or else he's going to have to spank you. That's a boyfriend's prerogative, you know."

She gave Amy's ass a few playful slaps. "Remember, you're one of his official personal cocksuckers. That's a big responsibility."

Susan was going to say more.

But Alan told her, "Mom. Please. Aims isn't really distracting me, but you are. She's doing great."

Susan left shortly after that. There was a new spring in her step, as she looked forward to taking her turn soon.

Suzanne, on the other hand, was disturbed by the situation when she came in, mostly because of her continuing inability to deal with her daughter's new sexual awakening. She nervously looked up at Alan, but her eyes kept drifting down to her daughter's tempting bare ass.

She complained, "Sweetie, don't expect me to bend under the table for you like that. It isn't dignified for any woman to do that." She hoped that would send a message to Amy not to flaunt her ass like that and that there were limits to how much they should pleasure Alan's cock, but it didn't have any effect. She resolved not to visit again until Amy had been replaced.

Alan wasn't happy with Suzanne's appearance either, since the interruptions were piling up. He complained to her, "What is this, Grand Central Station? In the last ten minutes, you, Mom, and Sis have all come in here. At this rate, I'll never get my homework done."

"Sorry," Suzanne said. "I guess we're all just a little bit eager to have some sexy fun with you. I'll put the word out that you aren't to be disturbed unless you call for something, or if it's time to replace your penis tender."

"Thanks," he curtly replied.

Time flew by, and he was pleasantly surprised to discover he could get a fair amount done with the stealth stroking going on. It certainly was a lot more enjoyable that way!

After thirty minutes, Susan came in wearing nothing but high heels, and took Amy's spot.

Alan wasn't surprised that she had more trouble than Amy keeping her efforts to a "reasonable" level. From the beginning, it was more of a stealth licking than a stroking, although she definitely stroked him continuously as well.

After a couple of minutes, he complained, "Mom, remember that this is supposed to be a stealth stroking. Emphasis on 'stroking.'"

She poked her head up from under the table to make eye contact with him. She pouted, "I know, but it's this positioning. It puts your big cock inches from my face. How can I NOT lick?! I'm only human! Please, allow me this pleasure? Think about all the nice things I've done for you over the years. I need to lick your cock so desperately badly! But I promise to just stick to licking. And if you can't study like this, let me know, and I'll go back to just a handjob. I really will."

He sighed heavily. "Okay, fine. You know I can't say no to you, especially when you give me that sad puppy dog look. But NO sucking! Okay?!"

She beamed with joy. "Yesssss! Thank you! I promise you, you won't regret it! You'll hardly notice I'm here!" She resumed her licking with great enthusiasm.

He shook his head in wonder. Man! Here I am, trying to study, while my naked bombshell mom is under the table and practically begging to lick my dick! After taking over from Aims doing the same thing! Good God! Who'da thunk my life would ever come to this? I swear, I'm never, ever going to get used to it!

Time passed.

He was pleasantly surprised that his mother actually stuck to her promise and didn't try to suck him at all. He was even more pleasantly surprised to discover he could continue to make progress even with that much stimulation. He knew better than to try something that would require a lot of mental energy. But luckily, he had some fairly mindless tasks to do. He was careful not to tell her this though, for fear that the stealth licking would turn into a full-on stealth sucking, after all.

After another ten minutes, he paused his studying to revel in the situation. Mom is the definition of a busty bombshell. Her hourglass shape couldn't be any more perfect in my eyes, and her face is motherly yet sultry at the same time. But she proudly calls herself one of my "personal cocksuckers," and she loves to do this sort of thing every day!

Is it really possible that this is how things are going to be from now on?! What if stealth stroking and even stealth licking catches on? What if all my lovely ladies really take turns licking me every time I do my homework, and they never get tired of it?! Could life actually be that good? For anybody?! And why me?! What did I ever do to deserve this?!

Man. Too many questions!

The time eventually came to decide who would take the next turn under his table. Suzanne decided to decline. She still considered it too undignified and indulgent to participate with the stealth help. Besides, she had to go back home and prepare dinner for her family.

Susan had to do the same, so Katherine relieved her after another half hour. She caught on that the stealth stroking had turned to stealthy licking, and happily did the same as Susan.

Then it was Amy's turn again. She also lapped on him non-stop.

Then Susan had another turn. And so it went.

Alan's dick was stimulated for over two continuous hours, yet at the end he still hadn't given up a cum load, since he wanted to save all his cum for the card game.

Alan gave his penis a break during dinner. He actually was relieved to be flaccid for a while. He worried he could be pushing his penis too far.

He made a point of helping with the dishes after eating to at least do some small thing to help stay grounded.

Then he went back to his homework. Susan came in to have yet another turn at the "stealth licking."

Despite his worries about overtaxing his penis, he enjoyed the help from earlier so much that he let her. The card game was to start later than usual, expressly to give him a couple more hours to study.

However, Susan seemed to be in a more serious mood this time around. She came in dressed in a silver silk cheongsam, a Chinese formal dress which covered a lot of skin by her recent standards but was slit high up her sides. Rather than sit under the desk as the others had done, she sat next to him in another chair and just jacked him off silently and lightly for some minutes.

But Alan had a hard time studying because of the way that she intently looked at him the whole time. Furthermore, he knew how much she preferred licking to justr stroking, especially if she could do it while naked and kneeling. Clearly, she wanted to talk. But she just stayed silent.

Exasperated, he put down what he was doing and turned his full attention to his mother. "Mom, something's on your mind. What is it?"

Still jacking him off, she looked at him with a touch of sadness, and said, "Tiger, I'm concerned. There's one topic that you and I haven't ever really discussed." She paused with embarrassment. "Making love. The two of us, making love."

His heart went to his throat to hear this most sensitive of topics broached. He tried to put the issue to rest quickly.

"Mom, I know you want to fuck me, and I want to fuck you. Or make love. That sounds better. You're perfectly fine with it, and so am I. Everyone who knows us, even the professional psychologist Xania, thinks it's high time already we get down to it. We're both waiting for the right time, and I'm sure it'll happen soon once your period is over. So what's to discuss?"

She sighed. "So many things. I have lots of concerns, although they're not the same concerns I had even two weeks ago. Of course I'm fine with it, to say the least. I can hardly wait! All my qualms are gone, and it's like I'm counting the minutes until you'll be fully sheathed in me, taking total control of me and my body. It means the whole world to me! But I'm wondering if it'll be so special for you."

She paused, then dropped her head, staring at her hand sliding up and down her son's erection. "I mean, you're fucking so many exciting and gorgeous women these days. Your big cock is stimulated in many different and exciting ways, each and every day. Could it be that your thrill in fucking your mother is gone? Is that why you're in no big hurry? Maybe I just don't have 'it' like Suzanne does? I still haven't figured out that squeezy PC-muscle thingy she does..."

He put his hands on her shoulders. "MooooOOOOoooom! Come on! You know that isn't true. I want you so bad that I'm a wreck most of the time. There's nobody I want to fuck more than you! I'm obsessed. Half the time when I'm fucking someone else, I'm thinking of you, imagining if this is what it'll be like with you or how it'll be different."

Her eyes lit up. "You're fucking me by proxy?!"

"Definitely."

"That's so hot!" Her hands slid up and down his shaft with renewed speed and vigor.

"There's nothing that excites me more than the idea of making love to you. Nothing! I love you and I want to love you in every way. I can hardly stand it. God, just look at you!"

He slipped a hand down to caress the underside of one of her big tits through her clothes, while bringing up his other hand to hold her chin and caress her cheeks. "Mom, listen to me. I love you with all my heart! I desire you in a carnal, lustful way just as much. The thought of fucking you is like a constant fuel for my lust, and it seems that most of the time when I'm fucking someone else it's just to take the edge off from the thought of being with you."

Susan was touched, and switched to stroking his thick erection in a more tender and loving fashion. "Aaaah, Son. That makes me so happy. But if that's so, why haven't you done me yet? Why don't you plant your seed deep inside me and claim me now and forever?"

He groaned lustily. His her and on her hefty melon slid to her erect nipple, which he pinched through her clothes.

She moaned lustily too. "Mmmm!" Theh she did something to her cheongsam, freeing the silky fabric over her tits and pulling that panel away, leaving her topless. Her huge melons were already heaving up and down in time to her heavy breathing. "Aaaah! That's better, don't you think? It's just like your favorite T-shirt!"

He brought both hands to her huge tits and pressed them together. "Oh God, Mom! You're so sexy!" He tilted his head down and planted his face deep in her cleavage. He took a big whiff of her scent. It smelled lightly perfumed and very feminine.

She held a hand on his head while still jacking him off. "Aaaah! That's nice! Mmmm...."

For the next minute or two, neither of them spoke. Alan couldn't easily speak, since his nose was deep in her cleavage, and he was licking whatever his tongue could reach. He also was distracted with his hands playing with her tits and especially her nipples.

Susan, meanwhile, was basking in the joy of the moment. Getting to stroke his cock while he licked and fondled her tits was as wonderful to her as sucking his cock, which meant it could hardly be topped by anything.

But eventually he sensed she wanted to say more, so he lifted his head back up to resume eye contact.

She stared deeply into his eyes while endlessly rubbing his sweet spot. "Son, I know I've been saying 'no' the whole time, but couldn't 'you' tell that my body was screaming yes? I've basically dedicated myself to be your full-time sexual servant. I call myself your personal cocksucker, your sex pet, and more... and I mean every word! I keep telling you just take a woman if you want her. Don't take no for an answer. Who do you think I'm talking about? Barbara Walters? I'm talking about me!"

She unexpectedly stopped her stroking and got down on the floor just below him.

That forced him to stop playing with her great tits.

Spreading her legs wide, she flipped up the flap of her one-piece silver cheongsam and lewdly exposed her pussy for him. "Look, Tiger! There it is! Do you know how many times I've put myself in a position like this, or similar to this? How much more obvious can I possibly be, showing off my needy cunt to you? I need your cock in me like I need air to breathe! I have to have it, in every hole! It's a mommy's duty."

She continued, "These last weeks has been the best time of my life, by far, but it's been utter torture too. There have been so many times I've half-expected you to lose control and just up and fuck me. So many times I secretly wished you would. But you never did. You've turned me into a complete sex addict because I've become at least as obsessed as you are! Probably more. At least you have other people to fuck and to suck you to 'take the edge off,' as you put it. I haven't had a real cock in me for ages! Fingers or plastic just aren't the same. I need YOU!"

She added with growing arousal, "In fact, the only man who's ever fucked me was your father, and for all practical purpose that still leaves me virtually a virgin. You could hardly call what he did to me 'fucking.' When will you have mercy on your poor mother? Think of me as your virgin mommy, and I need my cherry popped. God, I just have to get laid! Reamed! Stuffed!"

Alan's erection was as hard as steel looking at his mother splayed out like that. "I know, Mom. I'm sorry. It's taken me a long time to learn that 'no' can mean 'yes,' but I'm finally getting it. And there are times lately when I was ready to do it. But there's always been something that isn't perfect. And it's built up to such a big thing that I want it to be perfect. I have to admit, I'm feeling a lot of pressure. Everybody seems to think I'm the world's greatest lover or something. So what if I just have one climax in me, and that's it? That would be such a let-down for me, and I'm sure for you."

She snickered, "Well, THAT'S not a problem. Even if you cum fast, I know you'll be so thrilled that you'll get hard quickly and cum in me again and again and again!"

"I know! But even that isn't enough." He said more emphatically, "I want us to make love for hours and hours the first time. Nonstop for days, even! I want to drench you in my cum, from head to toe!"

She closed her eyes and moaned erotically, "Mmmm! Tiger! That's just what I want! To be your personal cum dump! To squeeze every last spermie out of you and onto my face! My tits! My ass! And especially deep in my cunt! Then I'll finally feel complete! I'll finally be your big-titted mommy slut in every possible way! Owned by you in every hole!"

He spoke earnestly, "I want that too! So very badly! But it seems that I've always been on the edge of physical collapse or utter penis exhaustion. I want it to be amazing! Unbelievable! The fuck of a lifetime! I want it to go down as the greatest fuck in the history of the universe. And I guess I'm afraid that I won't be able to be as good for you as I wish and dream I could be. I'm scared, I guess."

She got back up and sat on his lap. She stroked his unruly hair with one hand and his stiff hard-on with another. "There, there. Anything you do will be great, because I know how much you love me and how much you care for me. I have to admit that the event has been building up and up in my mind too, and I do want something really special. I love your fantasy of dousing me with your spermy seed, so I can rub your liquid love into my skin, all over. That will symbolically mark me as your sexual plaything in such a lovely way. But I'm sure that whatever you do will be awesome, because you're an awesome guy. My son. How was your first fuck with Amy? Or with Suzanne? Or Angel?"

"They were all great. As much as I hoped for and then some."

"There. You see? And the way you broke in my virgin ass exceeded all my fantasies. It'll be incredible because we love each other so much that our passion will overcome everything. You'll see." Her fingers sloshed up and down the pre-cum drooling down his shaft.

He smiled. "You're probably right. But there's more pressure on the man to perform, and I'm feeling the pressure. I keep learning new things so I'll be better when we finally get together."

He suddenly switched gears. "Mom, you know, there's more to life than stroking my cock. Speaking about breaking in your ass, let's lay on my bed so I can fondle your sweet behind. How can we have a serious discussion if I haven't properly 'gotten your attention' yet?"

She smiled and replied, "Yes, Lover." Then she moved over to the bed. She finally took her cheongsam all the way off, making a slow, tempting production out of it.

Once the cheongsam was on the floor, she whispered huskily, "Hnnng! Son, I love being naked for you. I love it so much!" She sensually ran her hands up and down her sides and caressed her tits. "Understand this is NOT a game for me. It's not 'sex talk' either. When I say I want to spend the rest of my life serving you and your big fat cock, that's exactly what I mean!"

He just gulped and even whimpered.

Then, bending over to let her huge globes sway downwards, she made an even bigger production out of taking off her high heels.

That caused a lurch in Alan's already painfully hard boner, because he knew things usually got hot and heavy when the heels came off. Lately, whenever he saw her, she was typically either in her high heels, or in bed, or in the shower. Occasionally, she was even in bed with heels, if he was there.

He got on the bed first, and then she got on top of him. They both moaned in pleasure of making full-on naked body contact. He especially loved feeling her large orbs press down and conform to the shape of his chest, but feeling her hairy dark brown bush scrape across the skin of his hot shaft was also quite stimulating.

She naturally reached for his erection again.

But he held her hand back. "Lover," - he made deliberate use of that word - "let me focus on your pleasure for a while. Let me put all my concentration on your ass while we continue our conversation."

"Okay. If you insist... for a while."

They both giggled at her cock stroking and sucking addiction.

She enveloped his face with her gigantic knockers. "Now, where were we?"

"Well, I wanted to talk about the whens and wheres of making love. I don't know much about women's periods. Do they come to an end all of a sudden, or is it a gradual tapering off?"

He aggressively mauled her ass cheeks while he spoke. Meanwhile, his penis poked out from the bottom of her ass, delighting his knockout mother in the way it rubbed against her ass cheeks. He'd become remarkably adept at doing all kinds of sexual things while maintaining a normal conversational tone.

She started sliding her ass back and forth over his stiffness, giving him a kind of dry hump. "There are some women's mysteries that should remain mysteries. I'll let you know when my body is ready to have sex, okay? We could do it during my period in a pinch, but I'd rather not for the first time. I hate to get graphic, but there are times when your mother is gushy in more ways than one."

"Oooh, you're right. More info than I need to know. But can you guess when it'll be over? Friday, I hope?"

"Friday, maybe Saturday."

"Saturday?! But I'll be on my hiking trip by then." He brought a hand from her ass to one of her enormous breasts resting on his face and started caressing it.

"Don't worry. Either you'll do it just before you leave or when you come back. Either way has its merits."

He asked, "Either way? What's the merit to waiting a whole 'nother weekend?"

"What if I just get a little taste of your fucking and then you have to go? I'll be so miserable. Suzanne was telling me today about how badly she needs it now that she's got it. Her day just isn't complete unless you filled her cunt with your sizzling hot seed at least once. I'm afraid I'm going to be the same way. They'll have to put me in a coma until the weekend is over or I won't be able to handle it. Actually, I'm probably going to be like that if we do it before OR after."

"Good Lord. How will I keep you all in line? I still have an energy problem, you know. It's ironic how all the sex was supposed to fix my energy problem but instead it just leaves me more tired than before."

She smiled a wicked smile. "Don't worry. I know you'll do just fine." She kept sliding against his boner, keeping the dry hump going (although it was anything but dry, with her pussy steadily leaking). "You'll keep all us sexy babes in line, I'm sure. In fact, I have one solution."

"What's that?"

"You have to keep us all under your command with a firm hand. Frequent spankings are in order when we get too needy."

He chuckled. "You're just saying that because you want more sexy spanking action. When spankings are a reward that just encourages everyone to be naughtier."

She chuckled too. "You see right through me. But it's true. Spankings are a good way to keep us under your thumb, but mostly, you have to control us with that big cock of yours. Keep us naked, wet, and ready, but not too demanding on your limited time and energy. Perhaps more fuckings for good behavior?"

"Excellent idea. In fact, that's such a great idea, I should implement the system right away and reward you for it. Since we still can't fuck properly, I know of a needy ass around here that seems to be demanding too many spankings." He reached around her to caress and squeeze her ass cheeks with both hands.

"Ooh! Are you going to give me a spanking as a reward or punishment? I'll take either."

They both laughed some more.

She repeatedly flexed and unflexed her ass cheeks in his hands to try to show she very much approved of him fondling her there.

He said dramatically as he kneaded her ass, "I know you will, but neither. I think you need a good assfucking right now!"