Six Times a Day Pt. 27

Story Info
Teen discovers anal sex.
28.9k words
4.7
164.4k
82

Part 1 of the 1 part series

Updated 10/31/2022
Created 03/16/2005
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
spacer x
spacer x
1,939 Followers

Part 27: Bad to the Bone

At well over a million words, this is one of a handful of the longest erotic stories ever written. The first couple of parts are mostly build up and teasing, but there's lots of sex later on. The story also has love, humor, plot, character, and a lot of popular acclaim, so you should give it a try if you haven't already. It has incestuous themes as well, so beware if that isn't your cup of tea. Because of the plot and character development, it really helps to start with Part 1.

This was written as a heavily illustrated story, but because of an unclear copyright situation with the pictures, it's posted here without them. The characters' private thoughts are marked in italics.

NOTE: In 2007, this story was massively revised and now greatly differs from the earlier version posted on Literotica. There are many new and heavily updated scenes, and scenes there were in one part are now often in another part. So please don't mind the confusion. If you've read it already you might want to read it again.

*

CHAPTER 1 (Wednesday, Nov. 13)

As Alan walked down the stairs towards the living room, he had a rough idea that he'd see the women playing cards in various states of undress. But to witness it live in front of him exceeded his expectations. He thought, It's like the female cast of Baywatch is playing strip poker, but these women are even hotter than them.

But what pleased him most was to see Brenda again. As he stepped into the living room, he said, "Hi Brenda, how have you been?"

She already had her top pulled down enough to expose her pointy nipples.

Alan, though, acted as if that was nothing out of the ordinary. In fact, he made a point of looking at her only in the face - for now.

She acted shocked and disturbed to see him. "Alan? What are you doing here? Suzanne, I thought you said the game would be just us girls!" She bashfully covered her chest with her arms, an act nearly made pointless by their sheer size - tit flesh bulged out everywhere around her fingers.

Truthfully, she was secretly very delighted. In fact, she was already so aroused that she spoke towards his crotch, unable to take her eyes off of the huge bulge that attempted to burst out of his shorts.

Suzanne, herself topless, said, "I thought Tiger would be too busy with his homework to join us, but it looks like he's finished."

Alan correctly picked up a hidden message to follow what she said.

"Yeah, I just finished my homework, and I'd be delighted to join in or just sit back and watch. Whatever suits you ladies best."

"I'm sure you would," Brenda complained. "But I don't want a young man ogling my body. I've already lost my top!"

He sat down to watch the game, incredibly aroused by the whole scene. "Well then Brenda, you should play better to make sure you don't lose."

As far as the game was going, Brenda had actually done fairly well compared to the others. So far she'd only lost once. After much joking encouragement, she elected to expose her long nipples since they were begging to be freed of constraints anyway.

By comparison, Susan and Katherine were topless, Amy had her dress off of both her tits and ass, and all Suzanne had left was her dress bunched up around her stomach, which covered nothing of strategic importance at all (though her pussy was hidden from most eyes by the table provided she remained sitting).

Brenda was trying to hide her strangely intense feelings for Alan, but she was so aroused by the game already that she didn't do a very good job. She replied to him, "That's easy for you to say. This is so embarrassing! Would you look at this? I'm not even partially covered up. You can see my nipples and my breasts are jiggling all over the place!"

She removed her arms from her chest so Alan could see exactly what she meant. "I might as well get it over with. It's not like I can play cards all evening with my hands over my chest. Damn." She picked up her cards and no longer tried to block his view of her monstrous rack in any way.

Alan thought, Nice, Brenda, nice. I can't wait until I'm pounding Alan Junior through THAT bottomless cleavage. She's so fucking STACKED! Wow. I wonder if I should take my penis out right now to give it some air. Or maybe even get someone to tend to it like during the fashion show.

Nah. That would probably freak Brenda out, not to mention who knows what Mom would do. Would she scream in protest, or demand to take charge of the stroking? There's no telling with her lately. No, it's better to hold off a bit until everyone is that much hornier. I'm sure I'll be getting a lot of stroking and sucking before the night is done. Patience, my Padawan, patience.

He focused most of his attention on Brenda, since he'd seen the others naked lots of times already. Plus, even if she'd been flat-chested, she still would have been one of the most outstandingly beautiful women he'd ever seen. She was amply endowed everywhere, especially on her protruding and peachy ass, yet she was full bodied, not fat or chubby. Her face, too, was heartbreakingly cute and beautiful. She'd never lost her baby fat there.

But he played down his interest. He had an instinct that she'd had too many guys go after her aggressively and that he'd have much better results if HE was the one to play hard to get. "Brenda, it's no big deal. Look around. Everyone is topless or more. No big whoop."

The others had built up Alan's reputation as the "insatiable sex machine." The mere fact that so many sexpot women were sexually involved with him at the same time was impressive and a strong aphrodisiac. Brenda felt a strange and irrational competitive desire to wow him more than he could wow her. This so-called "sex machine" is going to be putty in my hands just like every other man, once he falls under the spell of my huge tits and cute face.

He was playing her perfectly. His "no big deal" type comments egged her on, because the more he ignored her, the more she wanted him. To be ignored or even have to compete for attention was an almost completely unprecedented experience for Brenda ever since she'd grown her improbably large rack.

Within minutes of his arrival, she started to flirt with him. But that didn't earn her his exclusive attention. After a few more minutes passed, she saw him blatantly stare at Suzanne and she wanted that to stop. She cupped her tits with both hands and lifted them up, sheepishly smiling in his direction. That got his undivided attention, but only for so long.

Susan wanted Alan to look at her, so she stood up and asked if anyone wanted more to drink. In fact, this was just an excuse to get her rack bouncing. She rocked back and forth on her high heels to cause her nearly pale breasts to rock around in circles.

Alan, predictably, sat mesmerized at his mother's blatant tit show.

Brenda had to win his attention back by raising a hand up to her head, lifting her chest and jiggling her tits as well. She smirked in triumph.

But she didn't win his attention for long, as Katherine said something and gave him a smoldering look to keep him focused on her.

So Brenda had to resort to greater and greater extremes. Soon she overtly played with her nipples, just to win more looks from him. She tried to justify this in her mind by pretending that she was drunk, but deep down she knew she wasn't even tipsy yet.

Susan, meanwhile, was continuing with her tit show. She was very irritated by Brenda's larger rack. She considered it a threat for Alan's attentions.

There was so much jiggling going on that Alan joked, "I don't know what it is, but all of a sudden I'm feeling very hungry for some Jell-O."

Amy cupped one of her tits and asked, "Would you like some milk with that?"

Everyone laughed, but it also reminded Alan both of the Amy-inspired milk incident and of breast-feeding from his mother's chest, as Amy no doubt knew it would. Alan was surprised, since Amy didn't usually say those kinds of things. But he was also pleased, and very, very aroused to imagine Amy pregnant and lactating.

Alan joined in the game as soon as the next hand was dealt.

It seemed that as soon as Alan arrived, all of Brenda's luck left her. Perhaps her mind was too occupied by his presence and/or she was too busy modeling her body in sexy poses for his benefit to concentrate on the game.

But for whatever the reason, she lost the next three hands, and had to take off both gloves and then what remained of her top. She again made a big protest out of it each time, but secretly loved it. All she was left with was the narrow strip of fabric that covered parts of her crotch and ass.

She made a fuss about her losses. "What ever am I going to do if I keep losing, Susan? How long will I be able to stop him from seeing me completely naked? It's just not fair. You should have warned me that he'd be playing."

Susan loved Brenda's distress. "Tell me about it! There's not much we can do; he's the man of the house now. I find myself naked and humiliated on a daily basis. You might as well get used to it too."

Brenda didn't reply to that, but she found it strangely arousing.

Susan lost the next hand and had to pull her dress off of her ass. It still covered her crotch, and not much else. Now that Alan was there, she and everyone but Brenda and Alan switched to a strategy of deliberately losing.

But Brenda lost the next hand and had to expose her ass as well. She was so nervous that she just pulled her outfit off of her ass without getting up for anyone to see what she was doing. It took Amy sitting next to her to confirm that she'd done it.

Then it was Suzanne's turn to lose. All her private parts were exposed already, and the only thing left was for her to take her outfit off over her head completely. She loved to ham things up. She prolonged the taking off of clothes, mostly for Alan's benefit. When she finally did get it off, she made it look like that gave her an intense orgasm.

The sight of Suzanne struggling to get her clothes over her head and the inevitable tit jiggling that followed took Alan's breath away.

He thought, I've lost count of how many times I've stopped breathing in sheer awe tonight, and I've only been sitting here a short while. This has got to be the greatest five sets of tits ever put together in one place. I swear to God!

After Suzanne did that, Brenda commented to her, "You're completely naked now. Does that mean the game is over?"

"Of course not, unless we all want it to. Does anyone want it to end?"

A long pause indicated no takers to that idea.

Ever since Alan had arrived, Brenda had protested so much that she felt obliged to say something. "I suppose I can't quit now and ruin the game for everybody." That was a pretty feeble excuse, and in fact she was the most eager out of all of them to keep going, which was saying a lot. But she had her pride. She covered up the ensuing awkward silence by asking Suzanne, "So what happens if you lose again?"

"The usual rules," the pale beauty replied, as if those were obvious to everyone. "If all of the clothes are gone, the person with the highest hand gets to pick a dare for the person with the lowest hand to do. The winner can't be part of the dare in any way. Didn't you ever play strip poker when you were younger?"

"No. I got busty at a young age and kept growing, so my parents kept me on a very tight leash." Brenda was wistfully disappointed at all the fun she'd missed out on.

Katherine said mischievously, "Your parents kept you on a tight leash, eh? Mom, did you hear that? Sounds like an excellent suggestion to me. Now you know what I want for my birthday - a tight leash so I can be ordered around naked on all fours."

Susan chastised her daughter, "All right, Angel, I think that's quite enough joking." To the group, she asked, "Are you all sure we should keep this game going, after comments like that?"

"That's what your boundaries are for, Susan," Suzanne pointed out. "We all respect your boundaries. Are you willing to respect them too, Brenda?"

"Of course." Brenda wanted to keep the game going so she could get Alan to fall under her spell, not to mention the fact that she was having so much fun. Alan was obviously attracted to her - she'd yet to meet a straight man who wasn't - but she was frustrated that he already wasn't complete putty in her hands like most men who crossed her path.

It was a good thing though, that he'd opted for his playing hard to get strategy. Once a man started to grovel, Brenda would lose all interest. She loved a challenge. However, she was beginning to think that this game might be too much of a challenge. She'd never really had to directly compete with one woman as attractive as she was, but now all at once there were four.

For the time being, she tried to brave it out. It's tough competition, admittedly, but I've got the hottest body here. I'm going to prove it by getting him to admit it. I'll show everybody. It's obvious that he loves tits, so he's gonna love me the best.

Suzanne said, "Okay then, let's continue. Unless you don't want to, Susan?"

Susan was silent and briefly blushed. Despite her protestations, her pussy was pulsing. Her mouth could complain all she wanted to, but her pussy wasn't going to let the game end. Further, Susan's breasts were very emphatic that they wanted the game to continue. She didn't have particularly long nipples (that was something else she was jealous of Brenda about), but her crinkly nipples stood out about as long as they'd ever been.

CHAPTER 2

Suzanne pressed on and dealt the next hand.

Brenda lost that hand, and slid what remained of her outfit down past her knees. That revealed a pussy leaking like an open faucet. She realized that she hadn't felt so horny in ages, if there was anything in her life to compare the experience to at all. Her marriage had turned sour a few years back, which led to her upcoming divorce, and she'd rarely had any erotic experiences in the last couple years.

Katherine had Brenda in her jealous sights, and teased her a bit. "Hey Brenda, did someone spill a pitcher of water in your lap? I thought that you said you weren't turned on, and that you were just humoring us to keep playing."

Brenda bit her lip. She was at a loss for words. Finally, she muttered, very quietly, "It's not how it looks..." Trying to change the subject, she asked, "So what happens if I keep losing?"

Katherine's jealousy was flaring up and she wanted to scare Brenda off to reduce the competition. So she tried to shock her with something drastic. "Well, then I suppose Alan's going to have to tie you up and have his way with you. He'll probably fuck every orifice you've got. So if you've got any self-respect, now's the time to leave."

Little did Katherine realize, but that was music to Brenda's ears. She'd had bondage fantasies for years. So her only response was, "What would he use? Ropes or chains?"

Katherine was so bewildered by that that she didn't know what to say.

The game continued, though there were many raised eyebrows. Everyone wondered about Brenda.

Amy lost the next round, and bunched her dress up around her stomach, to expose her pussy, just as Suzanne and Brenda already had to do.

Because of the table, Alan sometimes couldn't see what was being shown off down below, unless the person sat next to him. So he asked Amy, "Aims, can you stand up so I can see what you've got there? We have to be sure that you've taken it off all the way."

"M'kay!" she answered with her usual bright smile. She held her dress up above her belly button while she swayed her hips back and forth to better show off her bald pussy. As she did, she proudly announced, "Alan is my official boyfriend!"

The others, even Brenda, were already well aware of this fact. But they humored Amy with smiles.

Then Susan lost the next hand and had to make the same display. As she gyrated her hips sensuously, she said in a matter-of-face tone, "Brenda, you may look down on me for acting like some kind of naked nympho slut for my son. And yes, I realize what I'm doing it wrong, from a certain point of view. But my son is just so virile! He has needs, great needs! Why, even the doctors and nurse have to admit that it's a medical fact he has to have his cock drained by big-titted babes over and over and over, every single day! Who am I to resist such a well-hung, cum-filled boy?"

Brenda found herself hypnotized, both by Susan's gyrations and by her sinful words. She longed to see Alan and Susan rutting, almost more than she longed to have Alan lying on top of herself, hammering her endlessly with powerful hip thrusts.

Then Brenda lost again and had to take what remained of her outfit off of her body altogether. She was still dreadfully nervous so she simply slipped it off while sitting.

But Suzanne could see that Brenda was horny enough to be pushed further. She said, "Tut tut, Brenda. That's not how we do things around here. Didn't you hear Alan's request to Amy that she stand while stripping?"

Brenda gulped. It was one thing to show off her breasts. She did that nearly every single day, though they were clothed. But she wasn't used to making a public display of her pussy. Her body actually trembled as she stood. She closed her eyes, as if having them closed somehow meant this wasn't happening.

Susan could be naïve and clueless at times, but this time she could see how uncomfortable Brenda was. After all, Susan had been in the same situation of sexual embarrassment many times in the very recent past. So, even though she was struggling with jealous feelings, her innate kindness took over and she tried to support her. "Brenda, I think you're doing great. And you're so brave. You have a very lovely pussy."

Amy could see what Susan was doing and began praising Brenda's pussy. "Yeah, Brenda, it's a way super great pussy. My boyfriend is totally gonna love poking it, I'm sure."

Suzanne did so as well. "Brenda, relax. You have a great body. Stand proud. And yes, your puss is pretty cute, too."

Katherine, though, was silent and filled with jealous bile. She was having a hard time not blurting out something insulting.

Brenda found the experience of having a group of women discussing her openly displayed pussy to be extremely humiliating yet strangely exhilarating.

Her knees nearly buckled when she heard Susan say, "It's so pink and wet and perfectly formed. Very wet, in fact. I know Alan will just love fucking it. That pussy needs a good taming. Tiger, don't you want to nail the shit out of her? I know you do!"

Brenda was incredibly aroused by the way all the other women took it as a given that Alan would soon be fucking her. She held her breath to hear what Alan had to say about her pussy, but he remained silent.

Eventually the comments trickled to an end and she sat back down. She remained quite nervous though, especially because she realized that she was now eligible for a dare if she lost again.

As the game continued, all the women except Brenda continued their talkative banter. They made jokes and lewd comments.

For instance, Katherine (who generally remained in a good and horny mood except when thinking about Brenda) teased when Amy turned to show her wide ass off to the group, "Aims, is all that white goo dribbling out of your pussy courtesy of Alan? Damn, I didn't realize he tapped you already, but he sure tapped you good!"

Amy blushed and replied, "No. I wish! That's just me."

Alan generally tried to remain silent in situations like this, figuring that was safest. At times, the others talked about him like he wasn't there, but of course he heard every word.

Brenda refrained from talking because most of it was women making sexual comments and compliments to each other. She felt very uncomfortable with anything smacking of lesbianism. She had mixed feelings about the flattering comments about her looks unless the comment came from Alan. And since he hardly said a word about anything, her curiosity about him grew and grew.

spacer x
spacer x
1,939 Followers
123456...8