6 Times a Day

‘Someone’ Special [ 3 / 15 ] 6K words

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The fashion show resumed when the snack break ended.

Alan had had such a prolonged, teasing-free break that his penis had become flaccid. Since Brenda had been the last one to win the job of penis tender, she was given permission to suck him back to full size.

Brenda felt like she’d won a national lottery twice in one night. First, she got to give him a brief titfuck, and now she was being allowed to suck him off for the second time in her life. Sucking Alan’s cock while kneeling between his legs and wearing only high heels had become practically the ultimate sex act in her mind, after hearing Susan repeatedly praise it with genuine passion. So she didn’t hesitate to choose that position.

Alan’s penis quickly re-engorged in her mouth. She covered his shaft with both hands, hoping the others wouldn’t notice and declare that her time was up. She’d learned from her first blowjob with him the day before, so she was determined to do much better this time. From the very start, her busy tongue lavished attention on his sweet spot while her tightly sealed lips slid back and forth over his cockhead.

She was highly cognizant of the fact that four other women were watching. Their critical observation greatly embarrassed her, but that humiliation fired her lust. She knew each of the four were talented cocksuckers, which spurred her to try to match whatever high standards they had set.

The others all realized that Brenda got off on a certain level of sexual humiliation, so they started talking to themselves in a way designed to push her buttons.

Suzanne began the process by saying, “Wow! Look at Brenda go! She’s going at it like she was born to be a big-titted cocksucking slut.”

Susan said, “Indeed. I’ve been training her every day, on the phone and in person, having her suck on a dildo. I hope she uses the advice I gave her.”

Brenda replied mentally, I am, I am! His cock is so damn thick that it’s a struggle just to breathe through my nose, but I’m hanging in there, thanks to you preparing me. In fact, I’m even using one of your favorite corkscrew moves as we speak!

Katherine was trying not to let her jealousy get the best of her, which wasn’t easy. She griped, “If you ask me, Brother’s cock has gotta be fully erect by now. Shouldn’t we resume the fashion show?”

Amy said, “Yeah. I’m sure Alan is having fun, but I totally want to get back to the fashion-y stuff.”

Suzanne said, “Fair enough. Why don’t we resume the fashion show right away? Sweetie, how are you doing? Are you fully erect yet?”

He grunted lustily. Then he replied, “Um, ah… it’s getting there.”

That got a good laugh from all the others, since it was obvious that he was fully erect and loving it, despite Brenda’s hands continuing to try to conceal that fact.

Suzanne said good-naturedly, “Okay. Hang in there, and try not to paint her tonsils. The show must go on. If you ever do manage to get ‘fully erect'” – she made mocking air quotes – “give out a strangled cry or raise a hand or something.”

He chuckled. “Okay.”

Brenda was thrilled that she’d be able to keep going. She gave up attempting to cover his boner with her hands, and instead began stroking his shaft while also fondling his balls. That gave her a great deal of satisfaction. Aaaah! Now, THIS is how it’s properly done. As Susan always tells me, a big-titted slut needs to use her tongue, lips, and both hands at once. Aaaaah! Naked, kneeling, slobbering my saliva all over his hot snake, lips and jaw stretched nearly to the breaking point, my nipples tingling, my cunt throbbing and leaking copiously, my cheeks burning with shame – does it get any better than this? I think not!

Brenda kept on bobbing for well over twenty minutes. Alan wouldn’t have lasted nearly so long, except that she was required to stop whenever the “stage” was empty, between one woman’s performance and the next. Also, she tried to switch to a slower and more relaxed style befitting a prolonged situation like this. However, her excitement was such that it wasn’t much different than going all out.

At one point, Susan left the room to get a digital camera. It was tough leaving the action to do that, but she figured Brenda in particular would greatly appreciate the photos later, especially based on her reaction to their last batch of photos of Brenda and Suzanne pleasuring Alan’s cock together. She mostly took pictures of Brenda’s cocksucking, but she and others occasionally used the camera to photograph particularly sexy outfits in the fashion show.

Naturally, Brenda was very embarrassed when Susan started clicking away, getting close-ups of her sliding lips. But as usual, her humiliation only increased her arousal even more. Besides, she knew she was going to love the pictures. She could hardly wait to see how she looked from another perspective. It inspired her to step up her cocksucking efforts while also playing to the camera, making sexy faces to try to convey the full extent of her lusty passion.

Alan was in a bit of a fix. He was enjoying what Brenda was doing so much that he didn’t want her to stop. Primarily that was because she was doing much, much better than the first time she’d blown him just the day before. She wasn’t nearly as nervous this time, so she could put all of Susan’s training into practice. Secondarily, he just loved the fact that Brenda was the one blowing him. It was the thrill of the new, as well as the thrill of an apparently successful conquest.

His main problem was that he was heedful of Suzanne’s advice that he needed to continue to impress her with his dominant manner and sexual stamina. It wouldn’t do for him to cum too soon, especially after he climaxed a mere minute or so after her titfuck started. That led him to do all he could to delay his orgasm, frantically squeezing his PC muscle non-stop.

Brenda didn’t have the sucking stamina of his other lovers, though she was determined to change that as soon as possible. Thus, eventually she switched back to more titfucking, while at least licking him from the top.

She was disappointed that she had to “resort” to doing that, but Alan was secretly delighted. The earlier titfuck went by so quickly that he didn’t have much of a chance to savor the experience. But now he could savor to his heart’s content.

At one point, while the others were distracted, he ran his hand through Brenda’s short hair and said, “Good girl. You ARE my sex pet now, aren’t you?”

She immediately crammed nearly all of his cockhead into her mouth, which was difficult to do given her on-going titfuck. But she wanted her mouth full so she wouldn’t have to answer that question.

He whispered some more, “I’ll bet you thought I forgot about the pledge I was going to have you say earlier, didn’t you? But I didn’t forget. ‘I’m Alan’s latest big-titted, sex toy slut.’ Let’s hear you say it. But only if you mean it.”

Brenda thought, Fuck me! I had thought he’d forgotten. What should I say?! Lord knows how much I want him to be my master, but I have to at least TRY to play hard to get to SOME degree. If I say that, I’ll give away everything! .

He simply stared down at her while she slurped on his cockhead and titfucked the rest of his shaft.

His dominating stare melted her resistance clean away. She looked around to make sure nobody else was paying attention, at least. Then she looked up into his eyes adoringly and whispered, “I’m Alan’s latest big-titted, sex toy slut!”

He felt a surge of “Bad Alan” coming on, due to such heady sexual success. He merely nodded and said, “You are.”

That was too much for Brenda. She came hard, even though she wasn’t touching her clit or slit at the time. It was a quiet cum though, except for the increasingly passionate but muffled moans coming from her sliding lips.

Eventually, Brenda had to stop when Katherine won the penis-tender title. (Susan’s and Katherine’s no-touching ban had finally been forgotten.) Actually, all of the outfits and performances were wonderful and there was nothing particularly extraordinary about Katherine’s that time, but he seized upon the opportunity as a valid excuse to end Brenda’s efforts just when he was about to blow. After her forced her to say that pledge, she seemed to go into cocksucking ioverdrive, and it was more than he could handle for long.

Brenda was extremely impressed by his stamina. With her eyes closed and her total focus on learning what techniques worked best on him, she had no idea how close she’d gotten to making him cum. She also didn’t realize the importance of all his well-timed, frequent breaks. She was left with the impression that he could last just as long as he wanted, even when she was doing her best.

She sat up on the sofa next to him. It had been very physically taxing on her mouth and hands, so she needed to just close her eyes and recover for a while. She wasn’t entirely upset that she’d been replaced, because she didn’t know how long she could keep going. He mind wanted to go on and on, but her body had been crying uncle.

Luckily for Alan, Katherine understood the need to impress Brenda with Alan’s stamina. Despite her issues with Brenda, she figured protecting their family incest secret came first, so she was sticking to Suzanne’s overall plan. She sensed that Alan was about as close to cumming as he could get without actually going over the edge. So at first she merely held his shaft, letting him have an undeclared strategic break. She knew that Brenda was resting with her eyes closed and not paying attention.

That was a real life-saver for Alan. He needed a mental break from all the intense arousal just as much as his penis needed a break from the stimulation.

But Brenda didn’t have much time to recover, because at the next break between fashion performances, Susan sat next to her and wrapped her arms around her bare back. Then she whispered in Brenda’s ear, “So, how was it?”

Brenda’s eyes opened wide to express her wonder. She whispered back, “Oh my God! I thought my first time yesterday was great, and it was, but this was a whole different level!”

Susan needled her playfully, “Yesterday was hardly your first time. You’ve been married twice, for starters. Remember how you doubted blowjobs could even be enjoyable?”

“Good Lord! I was SO wrong! I’ve never been so glad to be wrong. But in a way I wasn’t wrong, because what I did before, that WASN’T cocksucking. Not like… this. I don’t know what it was back then, but it wasn’t the epic struggle, the all-out intense effort, the, the… I don’t know what to call it, but what I just did was so INTENSE!”

Susan giggled knowingly. “How many times did you cum?”

Brenda was coy. “What makes you think I came?”

“Come on. This is me you’re talking to. Besides, I heard all your non-stop loud, sexy moans. There were times you pretty much screamed, even as you kept right on sucking with a nice, tight lip-lock. Good job with that, by the way.”

“Thanks! I figured even though I was cumming, I shouldn’t stop. The pleasure of his cock comes first!”

“Right you are! So how many times did you actually cum?”

Brenda frowned thoughtfully. “Huh. You know, I have no idea. I had a few particularly big spikes of pleasure, but it basically felt like one endless orgasm for me. From time to time I’d play with my clit a little bit; I guess that’s when I was screaming and cumming most obviously. But I don’t know. It was just one endless high. Even when he was taking his breaks between performances, that’s when I’d play with myself a lot more, so there were no breaks for me.”

She suddenly spoke with great exasperation. “You know what’s really frustrating?”

“What’s that?”

“That I only have two hands! I need three, at least! One for his shaft, one for his balls, and one to play with myself. Actually, two more would be good, so I could play with myself all over.”

Susan laughed. “Sorry. I know just how you feel, but having three or four hands isn’t an option.”

Brenda let out a blissful sigh. She turned from looking at Susan’s face on one side to watching Katherine’s hand sliding up and down Alan’s erection on her other side. (Katherine had just resumed jacking him off for real, now that she sensed Brenda was more alert.) Still whispering, even though she knew Alan had to be able to hear, she said to Susan, “Just look at that. So damn hot! Does that damn thing EVER go down?”

Susan smiled with pride. “You know the answer to that. Pretty much no. We’ll be sucking and stroking it all night! Then tomorrow morning, I’ll wake up, limber up my jaw muscles, and maybe wake him with my lips already sliding all over his hot cock-meat!”

“Mmmm,” Brenda murmured lustily. “That would be fitting. You should definitely do that! Gaawwwd, it’s so exciting for me to be a part of this!”

She suddenly eyed Susan like a hungry dog staring at a raw steak. She put her hands on Susan’s bare breasts and started caressing them from below. “Look at you! You really are his big-titted mommy slut. We talk about that on the phone all the time, but watching everything this evening has really brought home just what that means.”

“Mmmm,” Susan moaned blissfully, enjoying Brenda’s fondling. She reached out and did the exact same thing with Brenda’s even larger globes.

Brenda considered telling Susan about how Alan had “forced” her to make her “sex toy” pledge, but she decided to save that for later, when they could talk at length. Instead, she leaned forward and whispered in Susan’s ear. “Do you think… Is it really possible… that I could suck him some more tonight?!”

Susan whispered back, “You know that’s what it’s all about. We’re his personal cocksuckers, and this whole fashion show is just a fun way to keep his cock throbbing with joy for hours and hours! But what happens is up to you. If you put on a great performance, you could win the penis-tending job again. Maybe more than once!”

Brenda couldn’t believe how exciting that sounded. Woooowww! I wasted so many years of my life. Even after being married twice, I had no idea how great sexual pleasure could be! This is the most fun I’ve EVER had, and the night is young! I’m gonna suck him so fucking long that my jaw will ache for days!

The two of them continued to talk in this fashion until the short break was over. They also caressed each other in a very familiar manner, even to sharing another French kiss.

Alan did hear every word, despite their whispering, since he was as close to Brenda as Brenda was to Susan. Not surprisingly, his mind was blown all over again. Hot damn! Brenda is as into having fun with my dick as Mom is! Well, just about, anyway. I can’t even look at them, much less listen, especially with Sis jacking me off, or I’m gonna blow for sure.

Am I spoiled from too much attention? YES! Hell, yeah! How could somebody be more spoiled? I fucking love it!

Susan’s third-round fashion display resulted in Alan’s favorite outfit of the evening, at least up to that point. Ironically, it wasn’t a new purchase at all: Susan had dressed in Katherine’s cheerleader outfit. Since both mother and daughter were nearly six feet tall, the uniform fit Susan almost perfectly, except for the bust where it was much too tight.

Susan charged into the room, leaping about and waving her pom-poms in a great parody of the moves she’d often seen Katherine do.

The others all burst out laughing. Susan had pulled the top up over her chest, though, so her huge tits bounced wildly because she also wasn’t wearing any underwear. In addition, it seemed that just about every move she made caused her skirt to rise up, exposing her privates.

Susan focused some of her improvised cheers on Katherine’s penis tending. “Go, Angel, go!” She jumped and shook her pom-poms. “Who’s going to suck that cock? Angel! Suck, suck, suck! Fuck, fuck, fuck! Stroke, stroke, stroke!” She thrust both pom-poms in a different direction with each repetitive word.

“Stroke that penis, Angel, stroke it good! Stroke that cum-filled boy, stroke his wood! Gooooooo Angel! Gooooooo Angel! Suck his cock, suck your brother! Suck his cock or let your mother! Gooooooo Angel! Gooooooo Angel!”

Susan crouched down low, and with one last, especially prolonged, “Gooooooooooo Angel!” jumped high into the air.

She came crashing down onto the table she was standing on, and from there she moved into a splits position that placed her wide open pussy right before Alan’s eyes. This final flourish wasn’t done nearly as deftly as a real cheerleader would have done it – she even had to adjust her skirt when she was all done to give him a clear shot of her beaver – but she made up for that with her obvious enthusiasm and effort.

Everyone clapped except for Katherine, who took Susan’s encouragement literally and switched to simultaneously sucking the top of her brother’s erection while jacking off the rest. She correctly figured that Susan wouldn’t object, as that would only heighten Alan’s enjoyment of her performance.

Alan was very aroused, and also quite amused. He never imagined he would see his mother prancing around like a sixteen year old high school student, and he laughed out loud during her entire routine, especially at the absurdity of cheering on a cocksucking.

Man, I thought things were surreal before, but this takes the cake. The complete cake. There’s no way this is real. It’s so completely bizarre! We’ve definitely crossed into the Twilight Zone tonight with this whole fashion show thing.

Mom is growing more hip and funny every day. She’s developed such a sense of humor. I feel like I’m going to wake up from a very long dream at any moment and find the old mom covered from head to toe with her long sleeves and bows and thick blouses… Nah!

Susan came over to stand before him for the newly-traditional outfit inspection, with her cheerleader top pulled up over her breasts.

Katherine kept on bobbing on him with great suction.

Alan commented to the group in general, “You’re diabolical, do you realize that? Evil and diabolical. I love it. Whose brilliant idea was this costume?”

Brenda was in seventh heaven. The more pampered and stimulated Alan was, the more aroused she got, because it seemed like her wildest, most submissive fantasies were happening right there before her eyes. She never got over her embarrassment at being naked and acting slutty in front of the others, but she freely fondled herself because she was far too worked up to have any restraint.

Alan initially caressed Susan’s ass through the skirt, but he didn’t stick with the rule to touch only the outfit and not direct skin. Since it was his mother, he knew she wouldn’t exactly complain when he groped her exposed tits and explored underneath the skirt.

Susan proudly replied as her son ran a hand through her bush, “It was my idea. I know how much you love putting all your big-titted cheerleaders in their place. Which, naturally enough, is on their knees, between your legs.” Interrupting herself, she looked down at her daughter’s head where it was bobbing on Alan’s cock, then playfully hit it with a pom-pom.

Susan mock-complained, “Angel! Stop that right now. Just because you happen to be a cheerleader, it’s like you’re trying to make my words come true. You ARE on your knees between his legs, and that’s SO HOT!” Her eyes glazed over as she momentarily forgot the point she was trying to make.

But then she remembered, so she continued with a more serious admonition. “A little bit of that is okay, Angel, even if it is against the rules. But I can see from your indrawn cheeks that you’re using a lot of suction. If you keep going like that, you’re going to make him cum much too soon tonight. This is his day of rest, remember?”

Suzanne chimed in, “Seriously, Angel, even Sweetie has his limits. Give him a breather, okay?”

Alan snickered, “Day of rest?” Are you friggin’ kidding me?! This is the exact opposite of that. But hey, I’m not complaining!

Katherine pulled her lips off his shaft. She sat up and returned to merely stroking her brother’s rampant hard-on. But she complained, “Mom, no fair. You stole my cheerleader look. It’s hard enough to compete with you as it is, and now he totally loves this, too.”

Alan interjected, even as his fingers under Susan’s cheerleader skirt found their way into her slit. “Sis, I love you in a cheerleader outfit too. It’s just that a reversal of roles can be especially arousing. If you try acting and looking like Mom it’ll have the same effect. For instance, some morning you could surprise me by cooking breakfast in one of Mom’s erotic aprons. If you did that, I just might have to give you the fucking of your life.”

That made Katherine feel much better. She resolved to follow his exact suggestion in the near future.

Then he commented to Susan, “And I gotta say, Mom, impressive vertical clearance too! Michael Jordan’s got nothing on you.”

Everyone laughed good-naturedly at that, as they had throughout Susan’s entire faux-cheerleading performance.

Alan’s fingers in Susan’s pussy caused Susan to buckle over and fall to her knees a minute later as she had yet another climax.

She didn’t have time to lie around and recover though, because Alan said, “Sorry, Sis, again, this isn’t taking anything from you, but I think Mom won both the penis tending and blowjob prizes with that performance.”

Katherine sighed. “Yeah, Big Stalactite Brother, I have to admit it was pretty good.”

Susan was already shucking off her skirt and moving into position. She still kept the top on, pulled up over her immense breasts to present a visual reminder of her cheerleader role-play. As soon as Katherine’s hand let go of Alan’s dick, Susan’s mouth engulfed it. She wasted no time in reaching and bobbing over his sweet spot.

Brenda gasped lustily. She still preferred sitting next to him. In fact, she was cuddled up to him so close that she could have easily lent a hand, or stroked Susan’s bobbing head. Seeing the others’ pleasure Alan was very arousing for her, but seeing Susan do it shot her arousal level clear off the charts, because she was constantly aware of the fact that Susan was Alan’s mother.

Brenda was even more turned on by what Susan was doing because it reminded her of the “big-titted cheerleaders” that she and Susan loved to frequently fantasize about. Brenda didn’t even know the names or other details of the real cheerleaders, except for Katherine and Amy and a bit about Heather. However, Susan had shown her photos of Heather and Christine, so while Brenda knew that Christine wasn’t a cheerleader, she imagined all the other cheerleaders were as gorgeous and busty as those two.

As she watched Susan while rolling her nipples between her fingers, she thought, I was gagging on his incredibly thick cock just a little while ago, and then Katherine was, and now it’s Susan’s turn! Before the evening’s over, probably all five of us will have sucked until our jaws are sore, maybe multiple times! And he just kicks back and enjoys the extreme pleasure, like the lord and master that he is!

As if that isn’t fucking, lava-boiling-hot enough, this is just his HOME harem! He’s got a second harem at school! Sadly, I don’t know the details, but I’ll bet the buxom cheerleaders there take turns gobbling on his knob all through his classes! Yes, right through each and every class! The other students and even the teachers can only watch in envy! Gaawwwd, he’s such a FUCKING STUD! HNNNRG! He’s gonna make me cum again!

Sure enough, Brenda soon had another orgasm. She’d been cumming so frequently ever since the titfuck earlier in the evening that each climax wasn’t that powerful, so she didn’t have to scream and flail about. But while the orgasms weren’t so intense, the fact that there were so many more than made up for that. It was just like what she’d told Susan earlier: she felt like she was experiencing one continual climax nearly all evening long.

Suzanne liked to keep order and liked to keep activities going once they got started. So she shooed all the women except Susan, Alan’s current penis tender, out of the room so that they could help each other change into new outfits.

Susan learned from Katherine’s mistake of sucking Alan too effectively. She bobbed on him at a slow, contented pace, which allowed her to keep going during the performances.

As the third round came to an end, Brenda’s turn came up again. She walked onto the stage in an outfit that a dominatrix would wear. Although she realized that her plan to play hard-to-get had been a flop, she still believed that it was important to be mysterious and a challenge to seduce. She thought that perhaps a dominating look would intrigue Alan.

Her outfit was even more over-the-top than the first two outfits she’d worn. Her black leather left her vital parts exposed, especially her huge tits. She rakishly wore long gloves and boots on just one side of her body. But what was really outrageous was that she wore handcuffs on one wrist, and a chain between her ankles, limiting how widely she could stride. None of the others had ever seen real handcuffs and chains being worn before.

Brenda’s face and tits still hadn’t been wiped clean of cum, mostly because Susan had insisted she kept her pearly glaze look.

As Brenda got up on the table, Suzanne asked, “Before you start, I’m curious. Are you supposed to be the dominant one or the submissive one? We don’t know much about this S-and-M stuff.”

“Technically, I imagine this could be a good dominatrix outfit,” Brenda cautiously replied.

But Amy asked, “If you’re supposed to be all dominate-y, how does that work with your face all soaked with Alan’s cum?”

Brenda didn’t answer because she had no good answer. She thought, Uh-oh! They can see right through me. I’m afraid to admit what this outfit really means to me, because that’ll only increase Alan’s power over me. But what difference does it make? It’s pretty obvious that he’s going to be my master no matter what I do! I have a feeling that soon he’s gonna be plowing my ass while I beg for more, and there’s nothing I can do to stop it! Look at his big dick and how everyone takes turns serving it. God, the way Susan loves it with her mouth – it’s just too much! I just want to fall to my knees and take turns sharing with her!

Gathering her courage, she decided to drop a major hint about what she really wanted. “Good point, Amy. I said it could be a dominatrix outfit, but in fact I don’t swing that way. In my mind, this is the outfit of a sex slave. See the chains between my ankles?”

She reached down and touched the chain, setting her big jugs swaying and dangling. “That’s to remind me that I’m not allowed to go far without my master’s permission. And the handcuffs around one wrist?” She brought her hands to the handcuffs and caressed them. “That’s for when Alan, er, I mean my master, ties me to the bedpost and fucks me and spanks me!”

Letting go of the handcuffs, she ran her hands up and down her body, as if lost in the throes of passion. “And while this outfit covers a lot of non-essential areas, my pussy and tits remain fully exposed.” She firmly grasped her tits and squeezed them, causing them to bulge forward. “That’s at his orders, so he never has any obstacle whenever he wants to show me who’s the boss!”

That answer resulted in murmurs of approval all around.

Susan moaned her special “MMMM!” sound around her son’s thick shaft to show particular approval, even though she couldn’t see what Brenda was wearing.

Suzanne said to Susan, “By the way, your blowjob time is definitely over. Switch just to cock tending, please.”

Susan nodded as if in agreement, but she kept right on licking and sucking. In fact, fearing that she wouldn’t have much more time, she actually went from a lazy pace to a rather intense one.

Suzanne saw that and rolled her eyes in frustration. “Okay, that’s enough. You have to stop now. Tell her, Sweetie.”

Alan spoke up. “Mom, please. I can only handle so much! I really need a strategic break.” He hated having to admit that in front of Brenda, but he felt he had no choice; his situation was getting desperate.

Susan pulled her lips off with a satisfying smacking sound. “If you put it that way, then okay.” She looked around and finally got to appreciate Brenda’s latest outfit. As she wiped the cum and drool from her chin, she asked Brenda, “So why the collar? What does that mean?”

Brenda tenderly fingered her collar and smiled as if in fond remembrance. “I think that’s pretty obvious. It’s probably the best known, most universal symbol of submission, even ownership. Think of the collar on a pet, like a dog or a cat.” She looked intently into Alan’s eyes as she added, “Or a human sex pet. A collared woman belongs to her master. Her duty is to serve, and obey!”

“I see. Very interesting.” Susan was all smiles since she’d asked a leading question in hopes of getting an answer nearly exactly like the one Brenda gave. She further hoped this would plant a seed in Alan’s brain that collars would be a great gift for all of his women.