Fitz and Maddy

Fitz and Maddy

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"Hey Fitz," the young woman popped her head around the corner of her brother's bedroom. Fitzgerald was his real name, but his sister used to tease him with variations - he was on the Fritz, that he was having Fits. Eventually that morphed into Fitz and the name stuck.

"Hey Maddy," he turned from his desk. His sister was Madeline. When she first said he was having Fits, he retorted by calling her Mads (and said it was short for mad cow disease). But like most juvenile sibling rivalry taunts, that had faded over time. Now she was simply Maddy.

"Mom gave me $200," she said enthusiastically.

"What for?" Fitz was 22, stood 6'2 with soft brown hair and brown eyes. He had an athletic build but wasn't super muscular. He was still in college, taking just a few classes. He worked part-time to help pay his way, but also so he didn't have to take a full schedule. Otherwise, he was home most of the time.

Maddy was 21 years old, 5'9 with a slender build. She had darker brown hair and soft brown eyes. She was a year behind him in college, in part because she took a gap year and travelled with her friends.

"I think I'm supposed to get you out of the house - give her some private time if you know what I mean."

"Eww..."

"Anyway, let's go out for dinner. Dave n Busters? My treat!" She said playfully holding up two C-notes up at eye level for him to see.

"I guess I could use a break," he put down his text, grabbed his coat and followed her out the door.

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The establishment had a buzz from activity and patronage. Fitz and Maddy had dinner, then a drink from the bar. They surveyed the game area: there were pairs, groups of friends, and people moving around between carnival type attractions.

"Lots of couples having date night," he commented as they people watched.

"So, let's pretend we're on a date?" She hopped off the bar stool and took him by the hand.

"That's not what I meant," but he let her lead him across the game floor.

Maddy beat him at air hockey, then he schooled her shooting baskets. Towards the end she tried grabbing his wrist and her breast pressed into his arm. He cried 'foul' and made the shot anyway.

"Skee-ball for the tiebreaker?" she asked innocently.

They put in their tokens and the wooden balls rolled into the opening slot.

"Ladies first," Fitz deferred to her.

"Such a gentleman!" She winked at him and rolled.

They went back and forth with 20- and 30-point scores. Then Fitz landed a 40 and felt good about himself. But then Maddy countered with a direct hit 50 and suddenly she was in the lead 240-210.

"Final chance... don't let the pressure get to you!" She taunted him.

"What's at stake?" He asked.

"We should have made a bet at the start," she countered.

"Afraid I'll make the winning shot?"

"No way - you know this is my game... look at the score!"

"And you have the advantage, so..."

"Fine. If I win," she paused and smiled, "I get to drive your car home."

His Camaro was his prized possession - he never let anyone else drive it. "Only my girlfriend gets to do that, and well... you know what men want!" It was a running joke. He had been single since he got it - so that was never put to the test.

"Well, we did say this was a date!" She playfully pushed his arm.

"You said we could pretend..." but now he wondered what she was up to. "OK. And if I win?"

"Well..." she gave him a flirtatiously glance. "I know what men want."

"Oh, do you now?"

"Um," she hesitated. "But I don't do that on the first date!" They laughed.

Fitz looked at his sister and wondered. But he also realized she hadn't actually committed to anything.

She bit her lip as he stood forward and prepared to bowl. The ball glanced off the rim of the 50, bouncing away and ending up in the catch-all 10-pointer at the bottom.

"I win!" She jumped at him in excitement. Fitz instinctively hugged her, twirling her around. He was acutely aware that her breasts were pressed into his chest.

When he released, she stepped back and composed herself - then held out her hand.

"Keys please!"

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Back at home it was late, and the house was dark and quiet. They crept in and up the stairs, hoping to not wake their mom. Fitz followed Maddy beyond his room to hers at the end of the hall.

"Well, this was fun," she turned, pretending to get her keys from her purse. "We should do it again some time!"

"It's over?" He played coy and put his hand on the door frame for support. "You're not going to invite me in?" He titled his head and winked at her, 80's style.

"It's late," she played along. "Besides, this was just a first date. And I know you're a gentleman, so..."

"Wait, what would you have done if I had won?"

"We'll never know now, will we?" She toyed with him, then turned to close her door.

"Come on..." he had to know.

"Well, win next time and find out!" And with that Maddy quickly closed her bedroom door before he could see how much she was blushing.

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It was well after midnight when Fitz thought he heard someone calling his name. It was faint and the house was quiet. He wondered if he had been dreaming.

"Help me, please!" the ethereal voice called out to him again.

Fitz rose from his slumber and walked down the hall. He knocked ever so quietly on Maddy's bedroom door.

"Fitz?" she whispered his name just loud enough to be heard.

He entered, but she wasn't in bed. Her room was illuminated from the bathroom, the door was slightly ajar. He approached cautiously, pushing it open and peering inside.

Fitz admired his sister's adventurous spirit, her fun nature as evidenced earlier on 'date night.'

But right now, he was admiring her naked body in the water. Her hair was wet. Her long, smooth legs were visible amongst the sudsy water. Her chest was barely covered with a small washcloth.

"Do you need a towel, princess?" He found a folded towel on the vanity. But he was admittedly confused, as she could just have reached for it herself.

"No, I have a, um... a problem that I need your help with."

"Uh, sure."

"And no judgement about... stuff... right?" She made that look. He recalled their discussion about letting each other be adults ever since she caught him jerking off to porn... very normal, but he was embarrassed just the same.

Just then his vision caught a rather curious object: a rather large carrot leaning up against the corner wall along the top of the tub.

She noticed his gaze. It was hard not to look because it was so out of place. And so big.

"Yes, that."

"I don't get it."

"I got so worked up earlier... you know," she shrugged her shoulders. "I was using it, OK?" She acted annoyed to have to spell it out.

"No, totally fine. I mean, what's the problem exactly."

"It broke off."

"Where, in the tub?" Fitz started to look in the tub, pleased that he had an excuse to admire her nakedness in the water.

"It broke... OFF..." she was trying to hint and not have to say it.

"Uh, ok. So, what, you need another one? Are there more in the kitchen?" He turned to go.

"No, it's... it's still inside me."

"So, uh... pull it out. Surely you can get reach up in there yourself."

"I tried. I can't."

"How far did you push it up in there?" Fitz asked her.

"Not THERE." Her eyes went wide as she tried to avoid saying anything more.

His eyes bulged as he considered what she was not saying.

"Hey - no judgements!" she shot at him.

"Won't it just come out... naturally?"

"I don't know. I'm worried that it's too big..."

"I know! That thing is massive. What is it, 3 inches diameter?"

"It was smaller at the tip, then it gets gradually bigger."

"Well, you got it in there..." Fitz nodded knowingly.

"It's turned sideways, I think. Anyway, it's not coming out!"

"Gee Mads... I don't know...maybe... try a laxative?"

"No time... I'm worried about toxic shock!"

"Wouldn't it be better to ask mom to help with this sort of thing?"

"No... I just can't!"

"Uh..."

"Please - I need you to help get it out!"

"So, what should I do... get some tongs maybe?"

"Fitz! Seriously... I need your help!"

"OK, uh... how exactly?"

"You're going to have to... use your fingers."

"Wait... you want me to put my fingers... up your butt?"

"Shhh! No... I want you to help remove the foreign object from back there... before it becomes a real problem. Don't you think I'm embarrassed about all this?"

"Geez Mads, of all the things..."

"I promise, I'll make it up to you."

Fitz sat down on the side of the tub.

"So, what, just reach in there?" He asked her as he leant forward and put his hand under the water towards her legs.

"Wait, I think I should stand."

"Why?"

"Gravity. Might help."

"Good idea," Fitz said as he backed off.

"Towel please," she reached out with her hand, clearly short of grabbing one. Fitz handed her a towel.

"Turn around," Maddy said bashfully.

"What, you're OK with my fingering you but not seeing you naked?"

"You're not fingering me, pervert."

"Still, you have to admit it seems a little silly."

But he turned as she asked. As she stood, Fitz looked at her in the mirror. She was beautiful, and her wet body glistened.

Maddy looked up, realizing her predicament as their eyes met. "Hey!"

"Sorry," he quickly turned away, smiling.

"Well, at least you're not grossed out," she said as she tightened the towel around her body.

"Not at all," he smiled and tried to hide his true feelings. But it was hard not to think about her nakedness and their proximity to each other. And that he was being asked to put his fingers up her ass.

Maddy pressed up against the counter, then leaned forward slightly. "OK, I'm ready."

Fitz knelt down behind her. He touched her leg letting her know where he was.

Maddy slowly lifted the towel, one inch at a time. It was a little seductive, but Fitz wasn't going to complain. She exposed her cute butt, and he wasn't disappointed. She was still damp from the bath, and her body beckoned to him.

Fitz grabbed her hip with one hand and placed his other between her legs to encourage her to spread them. After she angled her legs and planted her feet, she reached back to grab her butt cheeks in each hand and pulled them apart.

He was staring at her exposed backside, and he could see her pussy underneath as well.

"Wow!" He tried to say silently, but it still came out loud enough for her to hear.

"Thanks Fitz," she blushed. "But if you're done gawking... I really do need your help."

He took a deep breath and tried not to think of her sexually. This was all a little surreal. On the one hand he loved his sister and would do anything for her. On the other she was a beautiful young woman, half naked and asking him to touch her. Albeit for an awkward reason. It was very hard - and so was he.

"Sorry, right." He reached up and gently put his index finger at her butthole. She squirmed as he inserted the tip into her. He leaned in and inhaled, smelling her skin, her scent, her private parts.

Fitz couldn't help getting excited as he grabbed her hip tightly and pushed his index finger all the way into her.

"Ow!" Maddy jumped.

"Sorry!" Fitz pulled out.

"It's a bit dry," she complained.

"Do you have any lube?" Fitz asked her, wondering if she needed it with the massive carrot she got stuck up there in the first place.

"All out," she replied.

"Soap?"

"No, that burns. Can you just... lick it and make it wet?"

"Uh, yeah. Sure." He was intent on helping her - or helping himself to her.

Before she could react, Fitz moved his face into her butt and stuck his tongue up her ass. He strengthened the muscle as he jammed it deep into her. God! She smelled and tasted great.

"Holy shit!" Maddy exclaimed, squirming and shifting in surprise.

"What?" He looked up at her as she grabbed onto the counter edges.

"I meant lick your finger first, not rim my ass!" She looked back at him with bulging eyes.

"Oh, uh... well... I think it got the job done."

Fitz licked his finger for good measure, then put it back into her rectum.

"Ugh!" Maddy moaned. "Gently!"

"Sorry, got carried away."

"I'll say," Maddy replied as she held on to the faucet knobs for stability.

Fitz felt something hard and round up inside her.

"I think I've got it."

"Yup, that's it," Maddy replied.

"You can tell?"

"Oh, I can tell all right." Her contorted face was hidden from view.

"But..." Fitz paused. "How do I get it... It keeps moving."

"Try to hook it and maneuver it out," Maddy replied. She shifted and adjusted as he moved his hand against her backside, and his finger up in her behind.

Fitz worked around in her for a minute, relishing in her tight ass constricting on his finger as he explored deep inside her. But the carrot eluded capture, it kept slipping away and avoiding his control.

"It's no use," he relented. "I'll need to use two fingers."

"Uh, wait..." Maddy said in a worried voice.

"What - it's no more than that massive vegetable you had up there..."

"Hey - no shaming, remember!"

"No, I'm all for it - whatever it takes. I'm just saying, if you can handle that, then two fingers shouldn't be an issue..."

"Well, I started slow and was working myself up to the big bang... you know... I was almost there when it snapped off."

"You know there are toys people use nowadays..."

"I've been shopping online. But I couldn't wait. And it seemed... I don't know... naughty."

"You really like stuff back there?" Fitz asked her, with surprise, curiosity, and partial delight.

"What, you've never had a girl ask you to eat her out and finger her in both places at the same time?"

"I thought girls just tolerated it."

"Oh, we like it, too." Maddy replied. "It helps having something to clamp down on - at least for me."

"So then why the hesitation with two fingers?" Fitz asked her.

"It's different. Before it was you know... sexual."

Something in the way she said it made him think she wasn't telling him the whole story, but he let it go.

"So, do that again," Fitz replied.

"What?" Maddy asked.

"Play with yourself," he said matter-of-factly. "It might help loosen you up. Then I can really get in there."

"Surely you can't be serious..." She retorted.

"I am serious," he replied. "And don't call me Shirley!" It was a line from the movie 'Airplane', and they both laughed.

After a moment he suggested it again.

"No," she whimpered. "I can't get into it like that. Not with you here. It's too... awkward."

"Suit yourself," Fitz replied. "So, are we getting this carrot out, or what?" And with that, he repositioned himself, then spread her cheek and positioned two fingers up against her, letting it sink in.

"Wait, OK," she stopped him. "I'll try. But go slow, ok?"

"I'll start with one finger," he explained.

Fitz watched as his sister reached down between her legs and started rubbing her pussy. He smiled knowingly, then pushed his index finger back up into her ass.

"Ugh!" She groaned as she felt twinges in her body from the front and the back.

Fitz got rather hard from the sensation of her sphincter tightening around his finger. But he had to focus on her needs.

"Almost ready?" Fitz asked naughtily alluding to the next step.

"Give it a minute!" Maddy complained playfully. Then she slipped two fingers into her pussy. She felt around inside her - relishing the sensations. It wasn't anything new - at least, not what she was doing. It was that she felt her brother's finger on the other side, probing her back door.

"I think that's enough, let's try two..." Fitz slipped a second finger into his younger sister' cute butt.

This wasn't exactly real foreplay; he was trying to help her with her problem. So, focusing on the task at hand, he pushed in further, locating the carrot and wrangling it with his digits. He turned it to align it longways with her rear opening.

Fitz pushed back against her sphincter that tried to repel off his invading digits. He started to pull down and she cried out.

"Wait... stop!" Maddy practically jumped off him, then screeched into the sink.

"What?" Fitz removed his fingers and looked at his sister with concern.

She pushed up to straighten her body. She tightened the towel around her, but faced away from him, unable to show her face in the embarrassment.

"Sorry, I was just trying to help...I didn't mean to go that far..." Fitz put his hand on her lower back lovingly.

"It's not that. I just... Look, I can't play with myself like this. I'm so embarrassed about the whole thing. You're my brother and it shouldn't be like this..." She put her hand over her face and started to cry.

"Hey," Fitz stood up and held her as she turned and put her head into his chest.

"I just don't know what to do," she looked up at him, worried. "I really want this thing out of me. But it hurts to try and remove it."

"Well," Fitz tried to think. "You did get it up in there... when you were about ready to get off, you were able to push it in a lot farther, right?"

"So, what, I'm a pervert for liking to have things inside me? Thanks Judge..."

"I'm not judging. I'm just saying, something that big may hurt at the start, but as you get worked up and closer to orgasm, then bigger things back there don't hurt as much. Like more fingers, right?" He held up his fingers to drive the point home.

"But we were just trying that," Maddy countered. "I just... I can't get myself excited like this."

"Yea, I know." Fitz looked at his sister with love. "So let me try."

"What?" Maddy looked back at her brother cautiously.

"Just think of it as part of the procedure... Dr. Fitz will loosen you up."

"I, uh...I don't think I could..." she wasn't sure what else to say.

"Right. But I could," Fitz knew he was right. It was the only way. "Come," he took her hand and led her into her bedroom.

"Lay down here," he guided her. He closed the door as she climbed onto the bed and lay back against her thick, fluffy pillows. She looked at him apprehensively as he climbed up on the bed on his knees, scooting up to her position against her bent legs.

"There's nothing for it," he said matter-of-factly. "I'm going to eat you out and loosen you up so we can get you off... I mean, so we can extract this rogue vegetable from where it doesn't belong."

Fitz lifted the towel exposing her. Then he simply spread her legs and lowered his face into his sister's body. He began gently touching her, figuring out exactly how and where she liked to be touched.

When he got his face right into her groin, he inhaled deeply, taking in the scent of her womanhood. Then he began licking at her clit. After a few flicks of his tongue, he moved down between her labia and stuck his tongue into her warm, moist insides.

Fitz wasn't sure what was more surprising, that he was licking his sister's pussy, or that she was going along with it. He was going to save her from the predicament. But he was also excited because he was finally getting to do something with his hot little sister who had become a sexy young woman.

He massaged her legs and abdomen, running his hands all over her and relishing in touching her skin. Fitz slipped a finger inside her warm pussy, then a second as he licked playfully at her clit.

He looked up from between her legs. The towel had dropped at her sides; she didn't notice or care. Fitz admired her naked body, and she was a pleasure to behold. Her round breasts beckoned to him to touch... Instinctively he reached up and grabbed one, fondling her and pinching her nipples.

Fitz was getting fully into it but found her staring back at him. Her face had competing looks of surprise and confusion, embarrassment and desire, relief and disbelief.