Crossing Boundaries Tim Pt 01

A huge thank you for those who are enjoying my stories.

This story is related to the preceding Mandy chapters. You don't have to read them in order, but eventually these disparate threads will come together. Here, we explore the goings on with Jerry's business partner Tim, as well as his wife and daughter. Enjoy!

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Tim sat in his leather wingback chair and looked at the vast cityscape from his 10th floor, richly appointed office. He and his business partner, Jerry, had built a tremendously successful software company together, and when the money train pulled into the station, Tim wasn't hesitant to enjoy the trappings of his nouveau riche status, having come up poor.

But today, he wrestled with something that money simply couldn't fix, as he was on the horns of a moral dilemma.

Like his partner, Jerry, he had a beautiful 18 year old daughter. Unlike Jerry, he was still married to her mother, and quite happily at that.

Kate, his wife, was a stunning woman, who despite being 41 years old, retained the appearance of a woman in her late twenties. She was a very petite 5'2" blond with crystal blue eyes and perfect B-cup tits.

In college, she was the girl everyone talked about. With her brilliant smile and flirtatious personality, all the guys assumed she was out of their league. The guys who thought themselves her equal - typically the arrogant jocks - were the ones to hit on her, but they were the most likely to face rejection. Kate was hot as hell, but she was also very intelligent, and looks mattered less to her than brains and a personality, something the average college football player lacked. With those guys, she wasn't out of their league, exactly, they were just out of their depth.

Tim had, as had so many other guys at school, worshiped her from afar for several years. His tekkie nerdy buddies just happened to frequent the same bar that Kate and her girl friends went to, and one night - one rather intoxicated night - he did something foolish, which somehow miraculously worked in his favor.

It started as a dare, as these things so often do, and one of his buddies said, "I dare you to go talk to her. I'll pay your considerable bar tab for a week if you get her phone number. If she throws a drink in your face, I'll pay for two weeks. If you chicken the fuck out, like I know you're going to, then you pay."

Tim looked across the room as the charming and vivacious Kate chatted easily with her friends, and said, "You know what? Fuck you, Jerry. I'll risk a little embarrassment for free booze, and it'll only be a week, cuz Imma fuckin' charm her little socks off!"

Jerry and the other guys laughed and laughed, but Tim pushed his chair away, staggered to his feet and wobbled toward the hottest girl on campus.

He approached Kate's table and cleared his throat to get her attention. Kate and her friends looked up at him and Kate smiled in amusement. No one ever approached her unless they were completely vain and full of their own good looks. But here was a basically average-looking guy, vying for her attention, and in spite of what those who didn't know her thought, she was quite friendly and approachable as a rule.

"You're Kate," said Tim.

Kate laughed, not unkindly, and said, "I am aware of that."

"And I'm not," said Tim.

"Oh good, because that would be awkward for both of us," replied Kate.

"You're sexy as fuck," Tim continued, "And I'm not."

"Thank you and you shouldn't talk that way about yourself."

"Can I talk to you for just a second? Can I sit down?" said Tim as he wobbled a bit.

"Yes, I think you'd better," Kate laughed again, a sound that, to Tim, sounded like the joyful sound an angel might make.

"Thank you, cuz I must speak to you," he said as he took a chair from a nearby table and positioned it next to her.

Kate said nothing, only raised her eyebrows as if to say, "Ok, I'm listening."

Tim took a moment to collect his thoughts through the haze of alcohol, and said, "I'm a genius."

"Really? I'm not sure I've ever met a genius."

"Yup," said Tim, "A certi-fucking-fied genius. And I'm gonna graduate this year and me and my buddy over there are gonna start a software company and we're gonna be jillionaires."

"Well! Isn't that exciting!" Kate was not typically the sort to mock someone, but this guy was making it hard not to.

"Yup. And my buddy dared me to come talk to you. And the deal is, ya see, if I get your number, then I get to drink for free for a week! And if I piss you off and you throw a drink in my face, then he'll pay for two weeks. And I'm broke, so..."

"So... you're asking me to throw a drink in your face?" Kate was giggling now.

"Now hang on, I told you I was a genius right? So I figure if I get your number AND you throw a drink in my face, he will owe me THREE weeks."

"Ooohhh.... That IS smart. But why would I throw a drink in your face?"

"Because," said Tim in a very serious, almost apologetic voice, "I'm gonna say something offensive to piss you off. I'm also honest, so you can't just throw a drink in my face to pretend you're mad. That would be cheating. So you have to really be offended."

There was something about this stupid, brilliant guy that Kate couldn't quite put her finger on. Sure, he was a little drunk, but she bought the line about his intelligence, ambition and honesty, and those things were pretty attractive to her.

"Hand me your phone," she said, reaching out her hand, "And I'll save my number. Then, you can have the last laugh on your friend when he pays for both of our drinks, when you bring me back here on our second date."

Tim started to hand his phone over, and stopped.

"Wait. Our second date?"

"Yes, of course. If I'm willing to go out with you once, I'll go out a second time. After that, we'll see. I would recommend not being intoxicated for either one."

"Oh, no! I wouldn't do that!"

"Good. Now, what were you planning on saying to deserve this Cosmopolitan in your face?"

"Well, it was gonna go something like this: 'Hey there Kate,would you sleep with a man for ten million dollars and you'd say, 'I might consider it.' And then I'd say, 'Would you sleep with a man for fifty bucks? Of course you'd say hell no and what kind of girl do you think I am?' And then I'd say, 'We've established that, now we're negotiating price!'"

"Oh my God, that is pretty awful!" Kate was laughing, "Tell me you've never actually said that to someone!"

"Oh HELL no. My Momma raised a gentleman. She'd kill me if I ever spoke to a woman that way."

Kate handed the phone back.

"Tell your Momma that you have a date tomorrow. Call me at seven and I'll give you the address of where to meet."

"So you're not gonna throw a drink at me?"

"Not tonight. But I would like to know your name. It isn't Kate, right?"

Tim grinned and told her his name.

It was fate, or destiny, or the gods smiling on them both, because from their first date, they were done with even thinking about being with anyone else. On their second date they got a hotel room and made crazy, passionate love all night. Neither were virgins, but neither of them were terribly experienced either, and they became practically obsessed with learning each other's pleasures and desires.

Kate had a particularly naughty side, and over the years they had both been quite willing to explore new sexual experiences. They'd done a bit of swinging; a guy/guy/girl threesome once, a guy/girl/girl threesome here and there - even a full swap with another couple a few times. Each of those experiences were fun and thrilling, but at the end of each encounter, they still preferred each other one-on-one, and the outsiders had done nothing to change that, or their loyalty to each other.

But now, two decades later, Tim sat in his office having recently discovered something about Kate, and he found it both stimulating and... he wanted to say 'disturbing,' but that wasn't the right word, though it probably should have been.

The night before, he'd told Kate he'd be at work late and then go play poker at a friend's house. This typically meant coming home at two or three in the morning. But the game was canceled last minute, so he arrived home unannounced, closer to their normal bed time. He hoped to give his wife a pleasant surprise, but as it turned out, Tim was the one who had a surprise in store.

As he approached his own bedroom door, he heard a woman moaning - a moan he was quite familiar with because it was Kate's. He stopped abruptly at the door and listened for a moment, only a little angry, but mostly surprised. They had certainly had sex with others, but it was always planned and discussed in advance. If she was in there with another man, they would have a conversation, but not a fight. Perhaps there was an explanation for the lack of disclosure - a chance encounter, an unexpected attraction...

Then he heard the words that became burned into his brain, "Oh Missy, yes. Eat mommy's pussy!"

Tim could have dropped dead from shock right there. His wife and DAUGHTER were having sex? He must have heard wrong, he thought, and continued to listen.

"Mmmmmm.... Your pussy tastes so good, Mom. I wanna make you cum."

"Ohhh... mmmm... sweety so do you! I love sucking on your little clit. Cum on mommy's face, baby girl. Give me your pussy juice all over my tongue."

From that exchange, it seemed that they were doing a sixty-nine together, and Tim realized suddenly how hard his cock had become as he heard and pictured that. He and Kate had fantasized about incest before. Sometimes she would talk dirty to him as he fucked her, creating images in their mind about having a threesome with their young daughter. And, Kate had always shown a tendency toward being bisexual, fully enjoying their occasional threesomes - generally with a much younger woman.

But talking in a sexual moment about incestuous relations - that was just fantasy! To be actually acting out on those fantasies? It was outrageous!

And, Tim had to admit, it was also fucking hot as hell. But he found himself unsure of what to do next. Should he confront them? Should he pretend nothing had happened? Should he go in and see about joining them? That seemed ridiculous and ill-advised.

In the end, he decided that perhaps discretion was the better part of valor, so he quietly went back out to his car and sent Kate a text.

"Hey babe. Game got canceled, be home soon."

After a moment, he sent another: "I hope you're horny as hell, because I want to fuck the living daylights out of you when I get home."

That statement was both true and also a test. He wondered how she'd be in bed tonight. Would she be satisfied already and disinterested? Would she avoid him out of guilt? He sat in the car and waited for a response. Five minutes later, his phone dinged, and he read her reply: "Oh good, babe, cuz I need to get fucked like a cheap whore right now. I want you to bang the shit out of me."

Tim realized he'd been squeezing his hard cock through his slacks the whole time. Fuck he was turned on. He waited a few more minutes for appearance sake, then went inside and went into his bedroom, half expecting to see Missy still in bed with her, but Kate was alone.

His sexy, petite wife was laying on top of the covers completely naked. Her legs were spread and her feet were in the air with her toes pointed seductively. Her pussy was dripping wet, and she was rubbing her clit and moaning softly. When Tim entered the room, she looked up at him with lustful desire in her eyes and silently mouthed the words, "Fuck me."

Incredibly aroused, time got out of his clothes, got on top of his wife and without foreplay of any kind, shoved his meaty cock into her pussy.

"Oh fuck, baby! You're hard as hell. God yes! Fuck me with that big cock, baby!"

Kate's pussy was well-lubricated with her creamy juices and Tim started hammering in and out of her. After a few minutes, he pulled out and forced her onto her stomach. Then he straddled her, pinning her body to the bed and shoved his cock into her from behind.

"Take my fucking cock, dirty girl."

"Oh fuuuuuckk baby! Oh my god you're fucking me so good. I'm gonna cum so fast. Fuck me hard!"

Tim grabbed a fistful of her hair and pulled it, then pounded in and out of her, punishing her tight cunt. Even after all these years and all the sex and her having a baby, her pussy was tight as hell and every inch of his cock ached with the pleasure of her.

"Ohhhhhh.....mmmmmmm....gggooooooddd baby," cried Kate, "I'm cummminnnngggg...... aaaaahahhhhhhh...."

He slammed deep inside her and held his cock there, feeling her orgasm, feeling her body shake underneath him.

When she went limp as the orgasm faded, he pulled his cock out of her and said, "Get on your knees, slut. You're gonna swallow my cum."

She did as instructed and climbed off the bed shakily. She went to her knees and looked up at Tim with glistening eyes and said, "Cum for me Daddy. I want to taste you. Cum in my mouth, Daddy. I'll be a good girl."

This was a roleplay they'd done before, and it stimulated them both, but this time, he had the knowledge that the mouth he was about to cum in had only minutes before been on his actual daughter's pussy. That image overwhelmed him with the pure taboo hotness of it, and he climaxed harder than he could ever remember. His cock exploded, covering her tongue and lips with cum. It splattered her face, forehead, and eyelids.

"Goddamn, little girl," said Tim, as the last drops exited his cock, "You like being a little cum whore for Daddy, don't you?"

Kate swallowed the cum in her mouth and said, "Yes daddy. I love being your little cum slut. Do I look pretty with your cum all over my face?"

"You're the prettiest little fuck toy I ever saw, baby."

"Mmmm.... Thank you, Daddy," Kate giggled like a schoolgirl.

Kate got up and went into the bathroom to clean her face, and Tim crawled into bed. They fucked twice more before the night was through, roleplaying Daddy and Daughter each time. The third session lasted the longest, because Tim took extra time to lick and finger fuck his wife's pussy to multiple orgasms.

While he fingered her, he whispered into her ear the dirty things he wanted to do to his daughter.

"I'm gonna fuck your little girl while you watch, baby. You'd like that wouldn't you? You'd like to rub your clit as you watch me slide my dick into your daughter's pussy, huh?"

"Ohhhhhh....fuuuucckkkk baby, that's so hot. Yes, darling, fuck our daughter. Make her feel all of your cock in her little girl cunt. Shove it deep in her."

Tim continued to finger his wife, "Does she like it baby? Do you like hearing her scream with pleasure while I fuck her?"

"Oh god yes, baby, she loves it! She loves her Daddy's cock in her little pussy."

"And you love watching it, don't you? You want her to lick your pussy while I fuck her from behind, don't you? You want to sixty-nine with her and lick her clit while I rape her little virgin cunt, don't you?"

"Ooooohhhhhh fffuuuucckkkk baby! You're gonna make me cum! I want our little girl to taste my cum, honey."

"Fuck yes, Kate. Cum on your little girl's tongue. Then I'm gonna pull my cock out of her and shove it in your mouth so you can taste her pussy on my cock."

"Ohhhhhhhh.....mmmmmmmm..nnnnngngggggggg.... YES! YES! I WANT THAT!"

"I'm gonna cum in her, Kate. I'm gonna pump your daughter full of cum and you're going to eat it out of her pussy. You understand?"

"Cum in my little girl! Fucccckkkk! I'm cumming again! Oh my GOD!"

Kate's body shook like an earthquake hit her, the force of her orgasm sending her into convulsions that spread across every muscle in her body.

Tim raised himself to his knees between her open legs and required only a few strokes of his cock before spraying Kate's pussy and belly with cum.

Spent, he collapsed next to her, and they held each other's quaking bodies. After they had each regained normal breathing, Tim got up the courage and whispered into his wife's ear.

"So, my love, tell me honestly. The truth. How DOES Missy's pussy taste?"

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SO much more to come!