Geek's BIG Break Ch. 01

This is a work of fiction, written for fantasy purposes. It includes unrealistic sexual practices and fantasy situations. If you like your erotica more reality based, then pass on this series.

All participants involved in sexual scenes are 18 years old or older.

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Gio McLeod stood looking in the mirror mounted inside his closet door. He knew he still wouldn't be the most desired guy in school, but he was a little less geeky than he'd been the rest of his high school career. Thanks to taking a job working in his father's roofing company as a runner over summer break he wasn't pasty white anymore. He'd started the day-after school let out last year and had worked 10 hours a day, six days a week loading 50-80-pound bundles of shingles into a truck and taking them to all the job sites his dad had going. Most days he moved around 1000 pounds of shingles twice each day. Once to load the truck, then to unload them at the job sites. He had filled out some and gained a bit of a tan.

While he knew he wasn't a heartthrob, he'd thought maybe this year he could at least find a girl willing to date and explore a sexual relationship with him. He'd held on to that hope until lunchtime today. He still ended up sitting at the same table in the cafeteria. With the rest of the undesirables.

Gio sighed. He didn't even have to wonder why. He was still the same gamer geek he'd always been, and a few muscles and a slight tan weren't going to suddenly make him appealing to the opposite sex. Not that he was looking for a ton of admirers. Gio just wanted a girl, any girl, willing to go out in public with him and maybe let him finally lose his virginity. He had to be the only 18-year-old male virgin left in the world.

He may not have ever gotten a girl naked or had sex, but he knew all about how to please a girl. Thanks to his second geeky habit. His first was that he was a gamer. He played online FPS and RPG games all the time. He wasn't stupid, but he wasn't one of the super smart, head of the class nerds either. Not because he wasn't smart, he just wasn't willing to waste his time doing busy work when he had an almost photographic memory. If he heard or read something or saw it, he knew it.

His second geeky habit was he read a lot. Gio had the unfortunate distinction, since the eighth-grade end of the year awards ceremony, of being the only student in the history of his school to have officially read every book in the school library. That was how he knew so much about sex and pleasing a woman. In a forgotten section of the library, he'd found a book he stole. The book was an old religious training book for engaged men called "The Act of Marriage." It was a book a pastor had written explaining how to sexually please a young groom's new wife, complete with drawings and diagrams. Gio had read that book cover to cover at least 500 times since he found it. He'd just never found a girl willing to let the geekiest of the geeks try any of the techniques out on them.

Gio's other big problem was, he couldn't dress like other teens. He had to wear dress pants or loose-fitting cargo pants, because jeans didn't give him enough room and caused him pain. There wasn't anything funny about wearing dress pants and T-shirts it just looked super weird, so he wore polo style shirts. Making him look more like the teachers than the other students. Which got him bullied and teased since he turned ten and couldn't wear shorts or jeans. Thankfully, now days because of board shorts being popular he could wear shorts barely, but not to school. Because that was against the dress code.

So here he stood, the most sexually frustrated guy in his school. Oh, he had a healthy libido, maybe too healthy. He jacked-off at least six times a day, sometimes more. Just to keep his balls from hurting. He didn't know what to do. He'd hoped by working and building some muscle and using his earnings to buy himself a used Harley, he'd have a chance, but nope still couldn't even get the geek girls to agree to a date. His best friend was Abigail Long, and he could have probably lost his virginity to her if he'd been braver. She lived next door, and they'd been friends since kindergarten, but when he'd finally discovered girls sexually, she'd already blossomed into the most gorgeous girl in school, and the star quarterback scooped her up as his girlfriend and never let her go.

Gio hated the dickhead. He was only with Abi because she was smart and did his homework for him, and she was so insecure that she did any humiliating thing he told her to do. Gio watched him the last four years use and degrade her. It pissed Gio off, and he'd wanted to use his martial arts skills and kick Dean's ass. But he hadn't, because he loved Abi too much to embarrass her. Abi wouldn't break up with Dean because she bought the bullshit the fucker told her. Dean was always telling her no other guy would want her, that she was only popular because she was his girl. So, because Gio hadn't been smart enough, fast enough, or courageous enough, he had to watch his friend get used by the biggest bully of them all.

None of this helped him with his problem. If he didn't find a girl to fuck him soon, he'd end up the only guy in college that was a virgin. Gio finally shut the door to his closet and turned on his gaming system. If he couldn't get laid, at least he could get online and kill some zombies. Just as he got ready to log on, there came a knock at his door. Gio looked up to see his older sister Fiona standing there. "Hey Squirt, mom said to tell you not to get online before dinner tonight. Her boss, and his family are coming to dinner. She wants us both downstairs so his daughters don't get bored."

Gio cursed under his breath and sighed out loud. "Great, just what I need to be forced to spend time with the Queen Bitch and her twin sister."

His sister laughed. "Hey at least, you can go to school and say you had dinner with the two of them. That should impress all your limp dicked geek friends."

Gio loved his older sister, but she didn't understand him, or what he was going through. She was everything he wasn't. Her dark-red hair, full lips, perfectly proportioned for her frame breasts, and tight heart-shaped ass were the first ones he went to in his mental spank bank. Most of his wet dreams and fantasies starred those lips, tits or ass wrapped around his dick. She was outgoing and had been popular in school. In fact, his older sister was the hottest girl he knew, even hotter than his best friend Abi. He sighed. "Yeah, and no one will believe it, and then they'll deny it and I'll end up an even more pathetic loser. Or they'll tell their boyfriends, and I'll end up in a locker or dumpster again."

His super-hot, red-haired sister was suddenly pissed. "You're getting bullied at school? Who?"

He looked at her and watched her blue eyes spark with anger. Her emotions causing her to breathe harder was causing those perfect Size 34C tits to heave. He felt himself stirring and had to look away. There was no way he could afford to get a hard-on right now. It would put a strain on his dick and his pants. "It doesn't matter, Fiona. I'm the lowest geek at the school. If it isn't Dean and the football team then, it's the smart college-prep guys. If not them then the Cheerleaders, Tiffany and Tara the most." He shrugged. I'll just try to keep my head down tonight and not give them something else to tell everyone tomorrow. I'll still probably get tossed in a locker because they didn't get to go out with their jock boyfriends tonight."

"I don't understand Gio? Why don't you stand up to them? You have a black belt in Krav Maga and Aikido, why let them toss you around? Why don't you just kick their asses?"

He smiled at his sister. "You're right, you don't understand. If I kick one or two of their asses', then next time they'll bring four or five. Don't you get it? I'm the geekiest of the geeks, I'm the one no one will care if they beat to shit and back. I'm the one no one will stand up for, or date, or even fuck. I'm the school loser. So, I keep my head down and in a few months it will be over."

His sister smiled a sad smile. "You should be able to find a girl, Gio. You've changed over the summer. One of the geek girls should notice, that at least next to your geek friends you're hot."

He shook his head. "I'm still the guy in the wrong clothes who everyone makes fun of, that's not gonna change."

She looked at him and put her hands on her hips. "Then change your wardrobe. You've got that kick ass Harley now, go buy some leather pants and biker boots and look like a badass."

He shook his head "I can't."

"I don't understand. What do you mean you can't?"

He blushed before looking at his sister. He'd told no one why he wore the clothes he wore. It was beyond embarrassing. Even his mom didn't know; the only one that did was his dad. "I can't wear jeans or leather pants, they hurt me. I need more room than they give me."

She frowned. "Please, you're not fat how can you need more room?"

He blushed. "Not in the hips or stomach, Fiona. In the crotch. I need more room in the zipper area."

Her eyes got round, and she laughed. "What, you've got a big nine-inch monster cock, little brother?"

He turned super red. "I haven't been nine inches since I was twelve, Fiona."

She laughed even harder. "Bullshit. You're telling me your cock was nine inches when you were twelve?"

"It's the truth. Didn't you ever wonder why I wear cargo pants and dress pants? They're the only pants my privates fit in."

"You're so full of shit, Gio."

He shook his head "I'm not."

She looked at his red face and realized he wasn't kidding her. "Show me."

"WHAT??"

"If you aren't lying, show me."

"What do you mean, show you? Show you my dick?"

"Yes, if you aren't lying, show me this larger than nine-inch dick." She reached out and started taking his belt off. Now Gio was pissed. He grabbed her hands and stopped her. "Get off me. You want proof that I'm not lying to you fine, I'll give you proof." He shoved her off him, stood up and dropped his pants on the ground. His enormous cock was instantly released from the confines of its prison, and like every night when he took his pants off, it started getting hard from the relief of the pressure his pants put on it. Then it grew to its full size. His sister just stared at his growing dick, and her tongue slipped out to lick her lips at what she was seeing. It was bigger than any dick she'd ever seen, even the ones she'd seen in the porn she watched when she needed to get herself off.

When Gio saw his sister's tongue slip out and wet her sweet lips, his dick got even more excited and sprang to attention. "Holy fucking shit Gio, that's the biggest Cock I've ever seen."

"I told you I wasn't lying."

She looked up from his dick and asked, "How big is it?"

He shrugged "I don't know. I stopped measuring it in tenth grade when it was longer than the ruler."

Her eyes got bigger and almost bulged out of her head. "It's longer than the ruler?"

"Yeah."

"Let's measure it." Fiona licked her bottom lip again before biting it. Her mouth was salivating over her little brother's huge Monster Cock.

"Fuck off, Fiona. I will not measure my dick for you. I told you it was bigger than the ruler."

She took a step toward the monster. "Come on, let me measure it. Fuck Gio, if the girls who are making fun of you knew you had that in your pants, you'd be fucking all the time."

"What are you talking about?"

Fiona reached out, trying to touch her brother's big fat dick. "Little brother, there are three things guaranteed to drop any woman's panties. A smoking hot body. You don't have that yet, but you're better now than you were before you worked for dad. We just need to get you lifting weights instead of just doing your cardio workout to keep working on the muscles you've started building. You're cute enough, you just need to build on those new muscles. The second thing is being rich, and unless you win the lottery, we both know that isn't gonna help you. But the biggest panty dropper, the thing that will get any woman 18 to 80 to bend over and beg you to fuck them; is a BIG. FAT. MONSTER. COCK!! And Gio, you have the biggest, fattest cock I've ever seen. Don't move I'll be right back."

Gio was shocked at what his sister had said. Would any woman truly want him to fuck them if they knew he had this big dick? He looked at the clock on his computer and realized he had forty-five minutes before his mom's boss and daughters got here. He needed to get busy if he was going to get his monster cock to go down. It usually took two or three loads of cum before his dick shrank, and he was going to be hard-pressed to get finished in time. He grabbed the bottle of lube and put a good dollop on his mushroom head and started working his cock. The thoughts in his head were all of his sister Fiona and the way she'd licked her lips when she'd seen his dick. He couldn't stop his mind from having her lick his gigantic cock and then sucking on him as he choked her with his dick. He was getting close to his first cum of the session when his door opened and in came Fiona. "What are you doing? Stop!!"

"What? Why? I need to hurry and get it to go down before mom comes looking for me."

"I want to measure it. While it's hard."

"You can't I told you it's bigger than the ruler."

Fiona smiled. "I heard you, that's why I had to get this." She held up their mother's sewing tape as she walked over to where he stood. She sank to her knee's so close to his dick, he could feel the warmth of her breath as she panted. His cock was right there at the lips he had just been fantasizing about. Gio groaned as she reached out with the tape and held it against the bottom of his cock where it joined his torso and then she took her other hand and ran it up his dick from the root with the cloth tape measure pressed between her hand and his cock. One long, slow stroke that had him on the verge of cumming all over her face. When she reached the tip, she had him hold the tape measure and ran her fingernail over his tip, causing him to jerk in response. Then she leaned in even closer, and her breath caressed him like a lover's kiss, and he twitched again. She looked up into his eyes and smiled. "Jesus Gio, thirteen and three-quarter inches, and she let go of the bottom of his dick and wrapped the tape around the largest part of his circumcised cock head. "seven and a half inches thick". Then she dropped the tape and licked his cock from his root to the tip. "What the fuck, Fiona? Stop that."

She licked him again and then again, moaning the entire time, and then she opened her mouth and shoved his cock head into her hot mouth and started sucking. Gio reached down to pull her off his cock, but she sucked and bobbed up and down taking more into her mouth with each downstroke, and his hands got tangled in her long red hair, he groaned at the warm wet heaven working on his cock. He felt his orange-sized balls start to churn, and he knew if he didn't get her mouth off him, he was going to cum in his big sister's hot sucking mouth. "Stop Fiona, I'm gonna cum." She moaned and wrapped her hands around the shaft, pumping hard and fast so that her hands and mouth met on each stroke, and then it was too late as his cum rocketed out of his dick and into her willing mouth. She started swallowing as blast after blast of her not so little brother's hot cum coated her mouth. There was so much of it that it was leaking out the sides of her stretched mouth. Warm and surprising, not like any cum she'd ever tasted before. Mostly, the guys she'd sucked had salty or bitter tasting cum. Gio's tasted like sugar and was so creamy that she wanted every drop.

Fiona just kept bobbing, sucking and swallowing until he had nothing left to shoot out. She pulled off his dick and looked up at him and used her fingers to catch the line of cum that was running from the sides of her mouth down her neck and licked them clean. "Your cum was so tasty, Gio." Then she realized that the cock she still had in front of her hadn't gotten soft. "Why are you still hard little brother?"

"I told you I needed to cum two or three times before I can get my dick to go down enough to get my pants over it."

Fiona stood and started taking off her pants. "Are you telling me, brother, that you have to cum two or three times before that monster cock gets soft?"

"Yeah, at least two, sometimes three or more."

"Get undressed."

"What?"

Fiona pulled her T-shirt over her head and dropped it on the floor next to her jeans. "Get fucking naked, Gio. I'm gonna fucking ride that cock and take away your virginity problem. But first..." She reached down into her jeans and pulled out her phone and snapped a picture of her brother in his polo shirt with that gigantic cock showing.

"What the fuck, Fiona?"

"That's proof, Big Brother. When I show some of my classmates what my little brother has in his pants, you'll be getting pussy daily maybe two or three times a day. But I get this beautiful big fat cock first."

She shoved, and he fell back on his bed. "We can't Fiona it's wrong."

She took his hands and put them on her perfect breasts. Then she pulled down her tiny boy short panties, showing him her pussy with its neatly trimmed red landing strip. "It's not wrong. It's frowned on and maybe illegal, but I don't care, I'm gonna get that monster in my pussy, or you aren't getting out of this room."

Then she climbed on the bed as she removed her bra and pulled it out from under his hands, leaving him holding the breasts he dreamed about sucking. He groaned, and she pulled his shirt until he had no choice but to let her take it off or get hung up in it. Then she climbed over top of his rock-hard cock and started rubbing her soaking wet pussy all over his huge donkey cock. "Fuck me, little brother. Let me cum on that big fat dick, and I'll let you cum whenever you want."

He was only human and here was one woman he had imagined burying his dick in, rubbing her obviously horny cunt all over his big dick. "If you do this, Fiona, there's no going back. You'll be my cum bucket and fuck slut."

"Shut up and put that cock in my slutty pussy Gio. We're running out of time."

He rolled her over until he was on top and reached down, guiding his cock head into her tight wet cunt. "Oh, fucking hell you're so tight."

"Go slow until I get used to that monster, it feels like your gonna split my pussy in two."

Gio couldn't believe how wonderful his sister's tight pussy felt as he worked his big fat cock into her tight wet hole. He went slowly, like she asked until he was bumping into the back of her cunt. "OH MY GOD", she was moaning. "You've filled my pussy all the way up. Jesus Gio, no one has ever been this deep in me."

"I still have more to give you."

She shook her head. "You can't, anymore and you'll literally break me. Just start fucking me. Please, I need to cum on your huge fuck stick."

Without another word, Gio started pulling out and slamming his cock back into his sister Fiona's pussy. She moaned with each thrust, and soon she's fucking up at him as he fucked into her. Then she's pulled the pillow over her face to muffle her screams. "FUCK, I'M CUMMING!! You're tearing up my pussy, and I'm cumming so fucking hard." She completely lost it and started thrashing and shaking under him as he hammered eleven of his thirteen inches into her pussy. He felt it clench and release around him, gripping and releasing with every thrust. His balls started churning, and he knew he was going to cum soon. He was in his sister bareback, because condoms wouldn't fit on his big cock. He tried, and they split every time he tried to masturbate using one. "I'm gonna cum soon, Fiona. What do you want me to do?"