6 Times a Day

As the evening wore on, Alan and Christine ate their meals and drank a lot of wine. While Christine couldn’t order alcohol, Alan ordered enough wine in his name for both of them. No-one else seemed concerned. Trying to hide Christine’s drinking only made the evening even more naughty and fun.

All the while, their conversation grew looser and more salacious. Christine took to flirting like a duck to water. She had the ideal situation to let go of her inhibitions, especially since this was the first time she’d ever gotten tipsy. The alcohol silenced her small internal critical voice and introduced a brassy exuberant new one that pushed her to “Go for it!”

Alan’s erection just seemed to get harder and harder as the evening went on, with no let up. But things got even worse when Christine asked for help with physical flirting in addition to verbal flirting. She practiced licking her lips, leaning forward to put her breasts on better display, chewing her filet mignon slowly in a salaciously sensual manner, and so on.

What made the situation strange was that oftentimes Alan would give her a flirty suggestion and then she’d act it out. For instance, he would encourage her to place her fingers suggestively at her lips as she acted ever more provocatively. As the evening wore on, her actions toward him became more and more enticing. Supposedly, it was all part of her flirtation practice.

After a while, she even made excuses to stand up so she could flirt with her whole body and especially show off her long legs, one of her best assets. When she did, not only did Alan gawk, but so did just about everyone else in the restaurant. Her overall appearance could only be described as stunning. Normally she tried to hide her blonde bombshell looks, but tonight she was eager to flaunt herself.

However, she was well aware that Alan was a “tit man” since he’d been gawking at her chest for nearly three years now, ever since they’d been in the same classes together. She told him things like, “It’s strange. This gown is cut so low on one side that there was no way I could wear a bra. I’m not used to the feeling. I feel so naked I might as well go all the way and just BE naked. All I’d have to do is let this one shoulder strap slide down…” She even put her hand on the strap before she burst into giggles, pretending her tease was just a big joke.

But what really caused Alan’s dick to turn harder than diamond was when she said during a break, “This is soooo much fun.” Then she leaned forward and whispered. “It’s a good thing I didn’t wear panties ‘cos they’d be ruined by now. Oh, and you know I’m not wearing a bra either, so it’s like I’m totally naked except for this dress.” Then she sat back and winked.

He wasn’t sure whether that was more practice flirting or if it was really true. (In fact, she was wet and braless, but she still had her panties on.) Regardless, the mere fact that someone so obviously sexually repressed as Christine would say that in such an easy going way, in a public place no less, was terribly arousing for him. He began to long for the meal to come to an end just so he could rush home and get some relief.

He said, “You’ve mentioned about being braless enough times already. Not that I’m complaining, mind you! But if you suggest pulling your gown down one more time, I think I’m going to die of frustration. Please, have mercy!”

She clapped her hands. “So, looks like my flirting is working?”

“Oh, it’s working all right.” He was so aroused that he was nearly miserable.

But she didn’t stop. “Are you really SURE I’m not wearing a bra? I could be wearing a strapless one, you know.” She sat back, winked and wiggled her rack, then added, “Perhaps you should check… Or maybe I should.” She brought a hand up to her chest and cupped her breast in a very inviting and sexual manner. All the while, as she had been doing on and off for some time now, she rubbed her thighs together to further inflame her own lust.

He felt he was going to break into tears, he wanted to touch those boobs so badly. He was trying to think of a good verbal comeback but was so overwhelmed with lust that he was having a hard time thinking.

Then he got a call on his cell phone. This was a big surprise since he didn’t even own a cell phone or realize that he had one in his pocket.

Hearing the ringing, Christine asked, “What’s that you have in your pocket?”

Her voice was so sexy that she didn’t need to say more. It was like she was staring at the outline of his long erection as she said it, even though his crotch was hidden under the table.

He pulled the phone out, fumbled with the buttons, and then brought it to his ear. He was so horny that his hands were actually shaking.

“Hi, Big Brother!” Katherine said into the phone. Before her brother could respond, she added, “There’s a bit of a family emergency. Please find a private place to talk and don’t tell your date who’s calling, okay? This is going to take a good while to sort out.”

He was a bit shocked and in fact was still catching up to the fact that he even had a phone to answer. He said “Okay” into his phone. Then he looked at Christine and said to her, “Uh, it looks like some kind of emergency. If you don’t mind, I need to go somewhere quiet to take this.”

Hearing him talk about an emergency snapped her out of her sexual fog somewhat. She said, “No problem. Take your time.”

He stood up, and asked, “You sure? This might take some time. I’m guessing a few minutes, at least.”

Her eyes bugged out a bit as she saw the large bulge in his slacks. She wasn’t sure, because his slacks were a very dark blue, but she thought she saw a wet spot there too. She quickly recovered, and said, “Uhhh – I think I had too much wine. The effect can really sneak up on you. This is a good opportunity to clear my head. So go ahead and take your time.”

She meant it too. She needed time to sober up and get her sexual urges back under control. She thought, So this is what it’s like to be tipsy. It really CAN sneak up on you. Oh my God, what have I been saying to him? I’ve been just as naughty as he has with my filthy mouth. Did I really just invite him to fondle my boobs?! Just about! This is craziness!

Alan walked about twenty feet away from their dining table to a quiet, secluded part of the restaurant where large bay windows gave a wide view of the ocean. As soon as he was situated, he said into the phone, “Okay, Sis. No one can hear me. What’s going on?”

Katherine replied, “Like I said, an important emergency. Mom sent me! Don’t worry, no one is dying or anything like that, but I’m afraid that I can only tell you what’s going on in person. It’s that serious.”

“What the heck? This is bizarre. For one thing, how am I even taking this call? Did someone slip Mom’s cell phone into my pocket? If so, why?!”

“Yep. We did. You see, while you were taking a nap the rest of us were already discussing the possibility of this emergency arising and we wanted to be able to contact you if it did happen tonight.”

“What on Earth are you going on about? Does it have something to do with Ron? I’ll bet it does. Did he come back unexpectedly? But if he did, why couldn’t you tell me over the phone. I’m confused. Get over here right away.”

Katherine giggled. “Don’t worry. I’m on top of that. In fact, don’t make a big deal out of it and definitely don’t tell your date, but I’m already here. Look across the restaurant towards the entrance. That’s me talking into Amy’s phone.”

Alan looked around and found his sister. He could barely see her on the opposite end of a very busy and large restaurant, but she was there. He never would have noticed her if he hadn’t been tipped off. He did see just enough of her to recognize the top she was wearing; it was a fancy item she only wore on special occasions.

He looked away so Christine wouldn’t follow his gaze. He said into the phone, “You’ve really got me confused now. I don’t know what this emergency is, but I’ll bet it’s some kind of trick or something. For one thing, you’re dressed up far too nice for an emergency.”

“I swear,” she said, “there really is an emergency. But we should be able to sort it out quickly. Tell your date that something’s come up and you’ll be back in about fifteen minutes.”

So Alan walked back to Christine and told her that he needed to take a fifteen-minute break to deal with an emergency and went to go find his sister.

Christine nodded. She was trying to look him in the face, but wound up staring at his crotch. Luckily for her, he was too distracted by the emergency to notice, or even realize just what an obvious bulge he was showing.

When he got to the front of the restaurant, he discovered that Katherine had retreated closer to the front door, making it visually impossible for Christine to see who he was meeting, just in case she’d thought to watch him leave.

Alan walked up to his sister in a huff. “This had better be good.” .𝘤𝑜𝑚

Katherine giggled. Even though she’d seen him off when he’d left for his date, she pretended to be surprised to find him wearing a three-piece suit. She looked at him with approval and more than a little hunger. “Oooh! Who’s this sharply-dressed man?”

He just growled impatiently.

He didn’t realize it, but she was standing right in front of the men’s room. She’d put a “Do not enter – temporarily out of order” sign on the door about five minutes earlier and had waited to make sure the bathroom had emptied out before calling. She said, “Oh, don’t worry. It’ll be good. Very good. But not here. This requires the utmost secrecy.”

She grabbed him by the hand and pulled him into the men’s room, leaving the sign on the door.

He was so eager to get to the bottom of the mystery that he let her pull him in and even let her drag him to the farthest toilet stall. When she closed the stall door, he impatiently whispered, “Okay, what the hell is so important and secret that you interrupt my date and drag me here…”

His voice trailed off because he watched in amazement as Katherine unbuttoned her white blouse. As her breasts bounced into view he looked around and realized he was trapped. She was standing between him and the stall door, and these particular bathroom stalls happened to go all but six inches to the ground, so there was no space for him to crawl out if he wanted to.

Oh shit! he thought. He knew he was in a weakened, vulnerable state, since he still needed relief for his raging boner so badly that he could hardly stand it.

Seeing that he’d fallen into a trap, he attempted to slip past her before her womanly charms and enthusiasm caused him to lose all control. They struggled a bit as he tried to reach the stall door, but it was too late for him because he was too worked up, not to mention tipsy.

He wound up with his hands on her breasts. Once that happened, it was like they were magnets and his hands couldn’t pull away. Within seconds, his dick was humping her ass crack too, despite all of his and her clothes. Just as quickly, he had her bra pushed down below the bottom slopes of her ample melons.

Katherine giggled with pure delight as she enjoyed his roaming hands and his insistent erection. She said in an obviously factitious and not very loud voice, “Help! I’m being mauled by some kind of horny elderly businessman!”

Giving in to the inevitable, he laughed. “Elderly? If that’s the case I’ll have you know I’ve taken plenty of Viagra.”

She just mmmm’ed contentedly as she let him play with her rack. Then she felt his erection pressing up against her ass even more insistently, and said, “Oh yeah, I believe it ‘cos I can feel it. Is that a monster pussy pounder in your pocket or are you just happy to see me?” She giggled some more.

He said, “Both. I have to admit I’m happy to see you even though you tricked me. For one thing, you’re just too sexy to resist. I love the way your outfit looks on you, but I love the way it feels on you even more.”

Katherine was wearing a white blouse with a black lacy bra underneath. She also wore black stockings and garters and a dark blue miniskirt. The miniskirt was nearly the exact same color as Christine’s gown, a coincidence Alan liked a lot. His hands had wandered down to her stockings and leather skirt, which was why he said he loved the way her outfit felt so much.

She turned around so they could be face to face, and then she reached for his zipper. “Finally! It’s time to deal with your emergency. I was watching you and Christine from across the restaurant. Even from more than 100 feet away I could see the way you two have been flirting with each other. She’s always got one of her hands on yours or vice versa. You’re like two little lovebirds, you know that? You’re both aroused, big time.”

“So what if we are?” he grumped, irritated at the reminder that she’d interrupted his date. But he let her fish out his pulsing and extremely needy erection.

She added, “I have to admit, it made me all hot. She was practically molesting her breasts right as I called. Christine the Ice Queen, no less! Looks like Alan the super stud strikes again. Big breasted bombshells the world over, beware! Because the bigger they are, the harder he pounds. Or something like that.” She giggled some more.

“It’s not like that,” he feebly protested.

As she was talking, she managed to remove her bra and blouse altogether. Now she handed them to her brother. “Here, put these somewhere clean.”

He looked incredulously at the clothes he held in his hand. “What? Why?”

She looked up at him with pretend irritation. “Because I’m your number one fuck toy. Of COURSE I’m gonna bare my tits for you.” She dropped to her knees and held his hard-on with both hands. “Ah. Here we are. The emergency.”

He looked around and noticed a bar for hanging things. He hastily hung her top and bra there.

She began to stroke his thickness. “Haven’t you heard anything Mom’s been telling you lately? You’re a terribly cum-filled boy, as she keeps saying. And when you get blue balls it’s only slightly less worse than another Chernobyl, in her eyes. Did you think we’d let you suffer with all that sperm build-up for your whole torturously flirty, yet still ‘totally platonic’ date?”

She said the word “platonic” with disbelieving sarcasm. “That would be cruel! I’ve been sent here to help.” She giggled some more as she poked light fun at how carried away Susan could get about Alan’s orgasm needs.

The only person who had sent Katherine though was herself. She was suspicious about these “non-romantic dates” Alan and Christine had been having, and since she considered Christine a serious rival threatening her own position with Alan, she wanted to see things for herself. Watching them flirt with each other, even from across the room, had confirmed her worst fears. She felt forced to follow through on a contingency plan that would prevent the date from going too far.

Alan’s slight drunkenness made him slow on the uptake. Further, he was suffering from very painful blue balls. So while he’d enjoyed the fondling, only now did he realize where their playing was going to lead. Thinking of the risk, he said, “We shouldn’t do this…”

Katherine just laughed and dismissed his feeble resistance. “Oh, please,” she said mockingly as she scraped her fingernails along his balls in a not at all unpleasant manner. “You know you want it.”

He couldn’t deny that, but nonetheless he protested, “You’ve got to be kidding me. You get me all worked up with worries and interrupt my date just so you can give me a handjob?!”

She giggled, pleasantly surprised at how well her scheme was working so far. “No, I did all that so I could give you a blowjob. For starters.” With that, she brought her face to her brother’s crotch and began licking.

But to his simultaneous pleasure and frustration, she went for his testicles instead of his erection. She buried her nose in his balls and slathered all around with her tongue. She popped his balls into her mouth one at a time and sucked on them with a passion.

He loved it, but he felt that now wasn’t the time. His balls needed release. He grabbed her head with both hands and redirected her tongue to his raging erection.

She got the message and immediately began sucking with a steady bobbing motion. She licked it inside her mouth as well. At the same time, she kept a hand cupped under his churning balls. She held them softly, massaging them gently, even as she attacked his dick with her lips like an out-of-control vacuum cleaner.

He was so overcome that all he could do was hold her head with both hands and assist moving her back and forth over his shaft. He thought, I can’t believe I’m going along with this! This is so wrong. So wrong! And with my sister, no less! The danger… This is almost as bad as when Heather made me fuck her in the parking lot. True, this stall is pretty secure, but what if Christine finds out where I’ve been? My life will be ruined!

The cocksucking made him think of his mother, since she’d been doing that to him so much lately. He mumbled, “Did Susan really send you to do this?”

Katherine mumbled as she sucked, “Im a maanna ashpeegeeg.” She slurred as she sucked because she didn’t really want to be understood.

But Alan asked “What?”

She said it clearly this time, even though she kept on bobbing. “In a manner of speaking.”

However, he was too worked up to talk anymore, so he didn’t follow up that deliberately elusive answer. In less than a minute, his urge to cum had built up so much that it was all but impossible to stop.

Release didn’t take long in coming. He’d been getting quite good at holding back and extending his sex sessions, but this time he hardly fought it. He was so worked up and anxious to get the dangerous sex over with that he decided to just let go. He began shooting into her mouth less than two minutes since she’d started sucking him off.