6 Times a Day - Chapter 17

Mom's Maid Outfit & Amy

Alan took a nap. Then, at about five o'clock, he came out of his room and into the kitchen to get a drink.

"Howdy, Tiger. Did Suzanne help you out with the computer?" Alan heard his mother speaking, but didn't see her. Then he looked down and saw that she was scrubbing the dining room floor.

He suddenly got panicky. Oh no! What does she know about what Aunt Suzy did in my room? But then, relaxing, he thought, Of course Mom must know that Aunt Suzy was removing the porn filter; she must be referring to that.

"She sure did, Mom! Thanks for allowing her to remove the filter. I think that'll really help me with my problem. Way better than those porn magazines. I don't think I'll have any problem doing my thing today, that's for sure!" He decided not to mention how looking at the real Suzanne turned him on much more than any pictures.

"That's good," Susan said out loud, but inwardly she worried. Suzanne went into his room dressed pretty skimpily and she's a very attractive woman. I don't know about that. It seems a liiiiitllllle bit … dangerous. God, what if he masturbates thinking about her? Or me? Did I go too far with that shirt last night? It's much better that he thinks about her, if he has to think about anyone. I should thank her later. Tiger looks like he's been reborn; he's totally over his blue mood!

Alan walked around the counter and took a closer look at his mother. She was wearing a dress and an apron. No way! She isn't wearing any panties!

His thoughts screamed through his brain as his dick, although weary from masturbating so many times, instantly sprang to life. Susan's ass was wiggling high in the air as her whole body rocked back and forth to the rhythm of her scrubbing at a particularly troublesome spot on the floor, which in turn set her large dangling breasts swaying in counterpoint to her rocking motion. Her short skirt left most of her ass exposed – an ass completely unencumbered by panties.

Her display was entirely unintentional. She'd made two promises to Suzanne: one, to go without underwear for a few days, and two, to wear this maid outfit for the day. Having worn panties her whole life and being unused to such short skirts, showing off her pussy or bare ass was a completely unfamiliar experience to her. She had been very conscious and concerned about it when she'd put the outfit on nearly an hour before, but she'd gotten into her habitual cleaning and had completely forgotten about what she might be showing.

Alan's jaw dropped and his mouth gaped open. He caught a glimpse of her pussy between her legs, the first serious view of a real pussy he'd seen in his life. That just got his heart racing all the more.

He immediately adjusted his suddenly erect penis in his pants to make its hardness less obvious. He walked around to stand in front of his mother and make idle chitchat. But really he went there so he could see her bra-free tits swing back and forth like two steadily rocking pendulums. They were still contained in the dress, but he was pleased to see that it was an extremely low-cut one. He didn't know whether to laugh with joy, or cry in frustration about forbidden fruit.

"Hi, Mom," he finally said to her.

"Oh! Hi, Tiger." She looked up at him and smiled.

He stood there watching her big boobs dangling and swaying while barely contained in her low-cut maid outfit. It was so arousing that he could scarcely believe his good luck. But after an increasingly awkward pause, he couldn't help but ask, "What's with the funny maid outfit?"

Susan blanched, because his comment reminded her of what an outrageously revealing outfit she was wearing. "Oh! That!" She suddenly stood up, like she'd just sat on a hot stove. Her eyes were wide with alarm and embarrassment, and she reflexively covered her breasts and crotch, even though her maid outfit already covered all her privates when she was standing (although just barely).

He was disappointed that he'd said something that caused her to cover up, but it was too late to undo it.

She turned her blushing face away as she said, "Isn't it silly? I made a bet with Suzanne and I lost the bet. I had to do anything she said, and this is what she chose – that I wear this for the day."

"What was the bet about?"

Susan had been teased by Suzanne about how she'd looked at Alan's erection during the doctor's office visit. She'd adamantly denied that she'd looked at it at all, but Suzanne knew that she had, so it was an easy bet for Suzanne to make and win. Suzanne had threatened to make a phone call to Akami to confirm it, which caused Susan to concede before Suzanne could dial the number.

Naturally, thinking about the bet caused Susan to get even more flustered. "That's not important. What really rankles me is that she's trying to get me to wear all kinds of crazy things all of a sudden. But I feel like a dork. Don't you think it makes me look dorky?"

"I don't know. Let me see." He walked all around her, especially taking time to look at her shapely ass again. Because she had a hand pulling her skirt down over her pussy, there was less tension on the backside of her skirt and he could see the bottom third of her ass cheeks without any covering at all. He would have been able to see between her legs to her pussy except that her legs were firmly pinched closed together.

He gasped. His mother dressed so conservatively all the time that he had never even seen her in anything as revealing as a bikini. To see some of her bare ass, especially up this close, was almost beyond imagining.

Still not realizing what she was showing off in back, she asked, "What?"

That stirred him to answer. "No way. Not dorky." Damn! Nobody with an ass like that could ever be called dorky. What's happening here? It's like I'm in the Twilight Zone all of a sudden! The 'land of no underwear' episode. Is Aunt Suzy behind this?

He walked back to her front side before she caught on that her ass was partially uncovered, adding, "I definitely like it. It's very classy. Definitely super undorky."

"Dorky, I tell you." But Susan smiled at the compliment. She added, "But what irks me even more is how demeaning it is. It's like I'm some kind of servant or slave or something. It's ridiculous! Can you just imagine me as some kind of maid servant, forced to obey every order given to me? I'm appalled. And I'm gonna get Suzanne back for this, I'll tell you that much!" She continued to stand there, rather awkwardly covering her privates.

He thought, Dang! I COULD imagine Mom as a maid. MY maid, obeying my every wish! Or better yet, a servant or slave. A sex slave! Damn!

He imagined himself saying, "Mom, bend over again. Here comes your master's staff."

Then he imagined her replying, "Yes, Tiger. As you wish. Take me doggy style!"

Arrgh! Too arousing! I have to get out of here!

Alan reluctantly left the room, realizing that if he stayed longer she'd get wise to what she was showing and then get upset at him for looking. Needless to say, he rushed to his room to masturbate yet again. Not surprisingly, he fantasized about her in that maid outfit.

But he wasn't done. After he masturbated, he sat in his room, fidgeting restlessly. I can't believe what just happened. I just masturbated to thoughts of Mom. Gross! But how can I help it? She's a woman – a good-looking woman. No, a GREAT-looking woman. God, she's so damn hot! And for all I know, even as I sit here, she's in the living room in that insanely-arousing maid costume bending over in some obscene position like I saw her in before. Showing off her bare ass. Or those giant swinging tits. Oh man! Just thinking about it, I'm getting hard as a steel bar. I can't stand it. What can I do; I'm only human!

Is this what they meant by 'helping me'? That can't be! Mom would never agree to that, not in a million years. I'm still waiting for her latest lecture about sex and sin. Maybe Aunt Suzy told her to lay off on the moralizing as it would interfere with my medical cure? Maybe. I can hope.

He stood up and began to pace back and forth across his room. Aaaarrrggh! This is killing me. What is Mom doing right now? It's been thirty minutes or so since I was down there. Is she still there dressed like that? I mean, it's not like there's something wrong in just going out and checking to see what she's wearing. But she's my mom… Aaaarrrggh! Dammit! Okay, just one quick look.

He quietly opened his door and hurried downstairs to the living room. To his considerable delight and simultaneous tortured horror, he discovered her still in the maid outfit, cleaning windows.

The house had high windows, so she had to stand on her toes and reach high to get to the top of them. Each time she did, her entire ass came into view. He could even see the pink of her pussy lips in between her ass cheeks, although her legs were relatively close together.

He thought his brain would split in two. Okay. I'm an Eagle Scout, and now I'm also an Explorer Scout. I'm a role model; I have to do the right thing. I have to tell her what she's showing, and not just gawk. She's my mother, for Christ's sake!

But on the other hand, I don't have to tell her right away, do I? I'm so painfully hard! This IS helping me! I won't have trouble getting inspired to masturbate for days. Years, in fact! Oh man. Her ass cheeks. So firm. No flab at all. They keep shifting back and forth, like she's doing a sexy walk. The desire to just put my hand right there…

He lurched forward a step or two.

No! … And why the HELL is she dressed like this anyway? If she spreads her legs at all, I might even be able to see her… Right between… No. Don't even go there, man. Don't even go there!

He noisily made his way towards her and said as casually as possible, "Hey Mom. Still wearing that funny outfit?"

"Dorky, more like." She was still unaware of her exposed ass, and was in her usual good spirits.

"Mom, I'm dying here. Dying of curiosity. What on Earth did you bet with Aunt Suzy that made you wear that?"

Susan turned around to face him and began to blush deeply. Then she turned away again, which happily brought her partly-exposed ass back into his view. "Oh, nothing. Nothing important."

Man alive! The mystery deepens! I wish she'd spread her legs a bit though, like they were earlier. I can't see anything between them… What am I saying? She's my mother!

Just then, Alan heard a door open. He saw that it was Amy, whom he and Katherine often called Aims in private, including in their thoughts. Aha! My savior! I can get her alone, and have her tell Mom to change clothing. Then Mom won't be embarrassed that I saw. Aims is very dependable and won't give me a hard time about it. Perfect.

"Hey, Alan!" Amy said in her usual upbeat style.

"Hey, Aims. Can I ask you a favor?"

"M'kay. Sure. What's up?"

Alan thought, Amy rocks! She's always so kind and helpful; she'll help me out for sure. And she's a total hottie too, just like her mother! Heh-heh!

So Alan quietly told Amy what to do, and Amy got Susan to be more mindful about what she was showing without letting Susan know that Alan had prompted it.

Susan was horrified to have to be given such a reminder. She immediately changed into less revealing clothes. Later, she wondered repeatedly whether Alan had seen anything, and if so, what, but she was too shy and embarrassed to ask or even bring it up. She was surprised to discover that she didn't really mind that much if he had seen her naked ass.

In fact, in her heart of hearts she wondered if it was really an accident that she was doing so many tasks that showed off her ass when she knew she'd be putting on quite a display.

Alan found he had no choice but to hurry back to his room and masturbate yet again.

As he lay in bed afterwards, he thought about Amy, since her appearance earlier put her in his mind. Ya know, if I need a girlfriend, why not Amy? Good ol' Aims. I mean, she's a total hottie, there's no doubt about that. How could any daughter of Aunt Suzy not be? She's one of the four or five most beautiful girls in school, there's no doubt.

And she's just awesome all around. We're like, best buds. No, closer. We're like siblings. Hell, we are siblings, almost. I mean, we've been hanging together since birth, although we haven't been so close since we became teens and started doing our separate "guy stuff" and "girl stuff."

But that's the problem: we're more like siblings than potential lovers. I just don't think of her that way. Although… she is totally, well, do-able, to be frank. But as a girlfriend, long-term? Sure, I'd grow to enjoy the sex pretty darn quickly, if only because she's got such a great, busty body. But I don't think we'd really click, overall. I mean, it would be weird. She's just… Aims. And I don't mean to be rude, but the truth is, she's kind of an airhead. I totally love her, in a certain kind of way, but we don't click on an intellectual level.

Besides, and here's the most important question: do I even WANT a girlfriend? A few days ago I would have said 'of course,' but now all kinds of exciting things are happening with Aunt Suzy and even with Mom! If I announced that I had a girlfriend, wouldn't those things stop? I probably should just roll with the punches and see what happens here.