Itachi was an Uchiha. This is true. But not any typical Uchiha. He wasn't an Uchiha that has gotten drunk before they could or has cursed out their respected loved ones a few times or has made out with someone who was a distant relative. And he expecially hasn't had sex. A bit of a...weird thing for an Uchiha. He was always a prude and Shisui was certain he'd come out of his shell if he'd just get himself laid. But Itachi wasn't too open to the idea. Itachi believed that he should wait to be with a woman that he found suitable to take his virginity or for him to give it to. And preferable a girl who was also a virgin. Because if they are both novices then he wouldn't have to be compared to anyone else. Shisui begged to differ. Saying it would be good if Itachi got a lady with experience so that he didn't have to mess anything up. And woman rarely compare men to others.

Maybe not rarely.

Itachi was rather annoyed by it all, but nonetheless he could mind Shisui ranting about Itachi and his nonexistent sex life, because what the hell, at least he could get a good laugh.

"I know this really cool girl, her name is-"

"Not interested." Itachi flipped a page in his book.

"Come on, all you do is read books and coop yourself up. You're 18 Itachi, a real adult! Have some fun for once!" Shisui seems to be trying to make a point, but Itachi couldn't see it.

"I'll repeat. Not interested." Shisui rolled his eyes.

"This is all you ever do anymore, is read, eat, study, and not even sleep, you're nocturnal-"

"That would imply I sleep in the day, which I do not." Shisui had a long pause before sighing and continuing.

"You're nocturnal. Ever since Fu Fu built you this forsaken house you've been more of a shut in than ever! You know even Sasuke was close to having sex." Itachi widened his eyes.

"He's only 13!" Shisui nodded, showing how sad it was.

"He's already seen a girl topless and he came back with a hickey one day. Have you ever gotten a hickey? No. I'm only trying to help here, by getting you treatment."

"Which just so happens to be sex?"

"Yes." Itachi rolled his eyes. He may have been less sexually active than even his middle school little brother, but that doesn't mean he wasn't...dating. Well, considering it took him three years of high school until someone pointed out to him that he had a fan club. He never noticed to be honest, he was surprised the school board even allowed it, since it was private school. And maybe he's had some crazy days but it was hardly anything compared the his other family members. And so he realized just how much he did need someone to be with. Not to have sexually permitting things with. Just a person of the opposite gender that he could socialise with and maybe hold for brief periods of time and catch and release with his mouth. Wow, he needed this more than he thought. He sighed after contemplating it for a while.

"Fine then. Introduce me to one of...these friends of yours." Shisui grinned and jumped up.

"You won't regret it!"

He already has.

He definitely has. The woman sitting across from him with a huge bust and had no idea what the difference between the color orange and the fruit orange was not his ideal lady. And she was blonde, so that didn't help. He personally preferred brunettes. Brunettes were always a thing with Uchiha. He perked when seeing the same haired girl he was thinking about pass by the table. A brunette, with a considerable amount of chest. Very attractive also. Not that he noticed, he only noticed the arm around her waist by another man. He furrowed his brows and contained a sigh. First woman to catch his eye, is taken. How unfortunate.

"Hey, are you even paying attention to me!?" The girl across from him screeched, but he didn't listen. From her screech caused the brunette to jump and look behind. That's when the two made eye contact. Neither wanting to look away, and neither wanting the other to look away. The girl blinked and looked away when the man next to her upturned his nose at Itachi when seeing who she was looking at. Itachi could see the two found out who exactly he was when he heard the woman give a small gasp and saw the man scowl. Itachi turned away as well.

"Right. Uh..."

"My name is Carey!"

"Carey. I won't beat around the bush, I'm not into blondes and I prefer a girl with smaller breasts and a brunette also, and you've got a high pitched voice that would really annoying me if we ever had sex, so sorry, but this won't work. Bye." Itachi knew that was pretty blunt, but he didn't have time to deal with a girl like that. He could hear her calling for him and sobbing really loudly, he was most likely being looked at as a jerk for making a girl cry, but he's done it before. It's not intentional, girls just always do that when he leaves.

How pretentious.

He got scolded by Shisui a bit more than he thought he would. Shisui ranting about how he shouldn't be so blunt with people that don't know him like that. Shisui was a bit of an idiot, obviously. Itachi just couldn't get that girl off his mind. It was obvious she was in a relationship, but there was some sort of...interesting feel to her. And while Shisui was talking on and on about how Carey was a cute girl, Itachi was only staring off into space.

"Are you even paying attention to me!?" Shisui groaned.

Itachi looked at him with furrowed brows. "You're starting to sound like that Carey girl." Itachi ruffled his hair. "Well, she probably got it from you." He pulled out his phone and ignored Shisui continuing, until something he said caught his attention.

"There is a perfect place for you to lose your virginity, a bar restroom!" Shisui grinned.

And at first Itachi thought he was kidding, but he was still grinning. "Are you serious right now?"

"Completely. I lost mine in the girls locker room. I think Madara told me he lost his in a barn." Itachi contorted his face in disgust. He shook his head.

"How old were you when you lost yours?" He was afraid of the answer a bit.

"15. And I see the look on your face, but hey at least you'll be the first Uchiha to lose his virginity at the age that it's legal!" Itachi blinked.

"Wait, what? What about my dad?" Shisui gaffawed.

"You think he actually waited until marriage? Anyway, that's besides the point. There are some seriously sick girls at that one bar over downtown. And yes, you have to be 21, but you're an Uchiha, they'll let you in. Also, I'll make sure you only get water." Itachi shifted uncomfortably.

He actually never thought about sex as much as usual men did or do. But he has wondered what it'd be like. And now that he's thinking about it, he was nervous. To the public, he's not a virgin, rumors about him losing it at 14 or 16. Some rumors say he lost it when he was only 12. Which was ridiculous by the way. Itachi shrugged. "I'll go. But don't expect me to help you home when you get drunk!"

They went, and Itachi didn't appreciate the loud music, the crazy lights, the drunkards, and the flirtatious bartenders. And maybe he looked like a kill joy just sitting in the back on his phone quietly, but he figured after tonight Shisui wouldn't remember a thing and he could just say he had sex without actually doing it. That is what he intended. He looked up when he heard the seat in front of him creak. He was very surprised to see that same brunette. She was smiling and her cheeks were rosy, she was only a bit drunk.

"Hey." She slurred. Itachi blinked slowly, and looked around. Was she really talking to him? "I'm Anko." She outstretched her hand towards him and that was his conclusion that she was talking to him. He waited a while and shook her hand, and right when he was about to say who he was she pulled him over the table and kissed him passionately. Usually, Itachi would pull away, but the kiss was surprisingly compulsive. And he couldn't help himself when he kissed her back. She ran her hands through his hair and climbed on the table, pushing him back into the seat. She ran her tongue along his bottom lip, and bit down slowly, causing him to groan. He held her in place by holding her waist, he didn't know why. Maybe Shisui slipped something in his drink but when she used her knee to grind his so far flaccid member he allowed it, and groaned, he never felt anything like that before. She removed her hands from his hair and continued by unzipping his pants slowly. Itachi widened his eyes and pulled away from the kiss, a trail of saliva along with it. She pulled his boxers down, "W-wait...!"

She grabbed his flaccid member and stroked it slowly, Itachi gasped. He covered his mouth, it was different when someone else was doing it. He couldn't believe this was happening right now, two fingers rubbing under him slowly and two rubbing the tip slowly, making him stand erect and having precum leak out. Itachi looked away, Anko smirked. She moved up and kissed his cheeks. "Meet me in the restroom, in five." She whispered, and climbed off of him. Itachi panted and let go a breath he didn't know he was holding. What in the world just happened? He looked up to see Shisui on the other side of the bar, and hadn't seen a thing. He looked at his phone dropped on the bar floor, two minutes had already passed from when she had told him that. He ran a hand through his hair.

Should he go? Should he stay?

He stood slowly when four minutes passed, and picked up his phone. He went to the restrooms, and stood in front for a while. Would she be in the men's or women's? He tested his luck with the men's restroom, and what do you know the only stall open was at the end, and he could clearly see a lady's leg poking out. He gulped. He called out her name, "A-anko?" He could hear her smirk.

"Here Itachi." Huh. So she already knew who he was? That saved him the trouble then. He walked to the stall slowly, and when he appeared in front, his shirt collar was pulled down, to have his lips crash down onto hers. She closed the stall from behind him and pushed him against it. She was moving faster this time, and pulled his pants down along with his boxers. She smiled, "Already hard? What a naughty boy." She removed her own garments, her shirt and then unclipped her bra. Itachi blushed and looked away. Anko rose a brow, then gasped.

"No, don't tell me. The Itachi Uchiha, is a virgin?"

Itachi stayed silent. Anko smirked and grabbed his chin to have him face her. She pressed her breasts against his still clothed chest, and used her still clothed lower half to grind against his free erection. "I...I.." Itachi started, she chuckled.

"You're so sexy when you're bashful." She whispered as she removed his shirt and kissed along his navel. She licked two fingers in front of him slowly and removed her pants, inserting the fingers in herself, while moaning and holding onto Itachi. Itachi felt disgusting by watching her stretch herself and push the fingers inside farther. She removed them after a while. Itachi realized what she was doing when she placed his tip at her entrance.

"I don't think we should-" But he was too late when she already moved down on him. Itachi stifled a moan and grunted when she kept moving on him so slow.

"I've never gone in dry..feels better than I thought.." She muttered, then something clicked in Itachi. He bent her over in a suitable position, and moved into her faster than before. Anko felt tears of pleasure gather in her eyes and drool roll down her chin. Itachi didn't even realize at the time, that he'd just lost his virginity, he hadn't realized that he barely knew the girl he was pounding into, he didn't think about how there could be a consequence considering he wasn't wearing a condom, he didn't think about how he may have been a bit drunk himself and that he was going to have a hangover, he didn't think or realize anything. But he did realize that sex felt great. And he did think that a bar restroom was a perfect place to lose your virginity.

Itachi groaned as he opened his eyes slowly. His head felt terrible. He looked around, where was he? This definitely wasn't his house or his parents house or Shisui's, and not the floor of the bar.

The bar.

Itachi shook his head, remembering what happened last night. He lost two virginities. His drinking virginity, and his sex virginity. Shisui would probably give him a pat on the back for finally 'popping his cherry'. Madara would do the same. His father would be fairly disappointed, as would his mother for not taking precautionary measures and for being drunk at the time. He wasn't necessarily drunk, he had water on top of everything. He sat up, and was thankful that the room was dark, he turned to see water at the bedside. He drank it slowly and looked over when hearing the door creak open. He recognised the female entering immediately.

"Okay, you're awake, good. Now you probably have questions. How did I get here, where am I, who are you, blah blah blah. I'm Anko, chick from last night, so last night we sort of had sex, and don't worry, I'm on the pill," he sighed in relief, "your cousin is passed out on the bar floor still by now. We're still downtown, this is my apartment. Oh, and that guy you saw the other day wasn't my boyfriend, just some guy. So you are probably disappointed that you lost your virginity to a sleep around like me, but it's fine, because compared to others, you were the best for your first time." She winked. Itachi blushed a bit.

He furrowed his brows, "Well, thank you for helping me...Anko. Sorry for troubling you."

"No worries, I also took the liberty of writing my number on your arm, also there's a pack of smokes in the drawer, always makes me feel better after drunk sex."

"I don't smoke." Anko rolled her eyes, and walked over to the drawer pulling out the pack of cigarettes. She pulled out a lighter from her bra and lit one cigarette, holding it between her lips. She climbed on the bed and sat very close to him. She inhaled the smoke of the cigarette and kissed him, blowing the smoke into his mouth. Itachi felt blood rush to his head and his eyes rolled to the back of his head, there was pure ecstasy, she pulled away and put the cigarette in his mouth instead. Itachi never felt so...alive.

"Now you do." She whispered. She smirked and climbed off of him, in the same fashion as the previous night. Itachi watched as she left the room and closed the door behind her. He let go another breath, along side smoke. He didn't know what his parents would do if they ever found out he was smoking right after waking up with a hangover from having sex with a complete stranger.

After a few minutes, Anko walked back in with an ashtray and his phone. "Don't worry, I didn't go through your phone." She placed the ashtray on the night stand. She removed it from his mouth with all but reluctance from him and put it out. "Come on, I'll take you to that one million dollar mansion of yours."

It was actually a 12 million dollar mansion, but whatever. When driving back, Itachi was hoping his parents weren't completely scared and wondering where he was, because Shisui would have freaked when not finding him in the bar and told Fugaku and Mikoto unfortunately. And right when they got there, and Itachi was soon to step out of the car, Anko pulled him back into a kiss, Itachi felt sparks go off in his mouth. He couldn't describe the feeling he got with her, "See you soon Uchiha." She nearly moaned it and let go of him, Itachi stepped back as she drove off. He blinked and smiled slowly, which turned into a grin.

He went through the gates of his home and wasn't surprised to see an angry Fugaku, a worried Mikoto, and an even more worried Shisui and a bit guilty. Mikoto gasped at seeing him enter.

"Itachi!" She ran towards him and glomped him in a hug. He slowly hugged her back and looked to see Fugaku lower his angry face a bit. Mikoto sniffed him. He felt like he knew why. She did so again. "Itachi, we were worried sick, and I know you just got back, but...why do you smell like smoke?" Itachi glanced away.

"Would you believe me if I said there was a fire?" Itachi muttered, but they all heard him. Shisui face palmed and Fugaku shook his head. Mikoto cocked her head to the side.

"Unless you'd be telling the truth."

"Then there was a fire." So he lied. Didn't matter, his father would pull him aside and make him tell the truth anyway, then he'd just tell his mother later.

"And...you also smell like alchohol..." Mikoto's smile of relief twitched into a frown.

"Would you also believe me if I said that someone poured it on me to get fire off of me?" That's when Fugaku had enough.

"Itachi. Office. Now." Itachi sighed. He hated those words. Whenever he did something less than acceptable Fugaku would say that. He thought he'd escaped those magic words when he moved out, but his father only built an office in his mansion to get him somewhere to scold him whether they were in his home or not. Itachi followed his father reluctantly.

"Itachi, you smell like smoke, alchohol, and you're radiating, care to explain?" Fugaku glared.

"Like I said, there was a fire-"

"The truth, Itachi." Itachi sighed.

"Last night, I went to a bar, with Shisui." He didn't want to throw Shisui under the bus though. "I talked him into it, he tried to stop me. And when we got there, there was this girl," Fugaku rolled his eyes, it's always a girl, "That...came onto me, and I was drunk, and we..."

"You had sex!?" Fugaku roared, and Itachi was pretty sure Mikoto and Shisui heard it from outside.

Itachi rolled his eyes this time. "What's the problem, you lost your virginity before you were married and you did it before you weren't 18! At least I am! Why do parents always try to change what they did when they are just being hypocritical..."

Fugaku held the bridge of his nose, "We want better for you of course. And you were drunk, so you drank also? Really Itachi, I can't deal with problems everyday. And you smell like smoke, because what? That girl taught you how? Why do you only attract the troublemaker women?"

"Oh really? Madara." One word was all it took.

"Stop defending yourself with others. That's it! You're on probation. You focus on your studies from now on, and for one, no, two months nobody is allowed at this house. Nobody but me. Your grades slip even a bit, and I'll be taking back this house, the four cars, and the watch." Itachi gaped.

"How is that remotely fair? Punish Madara then!"

"You have nerve Itachi! I hope Sasuke will do better in life than you!" Fugaku was surprised at what he said himself, especially when he saw Itachi's saddened look.

Itachi's lip quivered, "You...you...I hate you!" Why did he say that? He didn't know at the time and he regretted it immediately after. When seeing Fugaku's broken face. Itachi groaned in frustration and stormed out of the room, and ran upstairs to his master bedroom, locking the door and throwing himself on the bed.

He felt like a teenage girl in a mid life crisis because he lost his tube of lip gloss and first boyfriend. He wasn't crying, but he had a torn feeling in his chest. Almost like...sadness and anger and jealousy combined. Sadness for disappointing his father. Anger for his brutal punishment. And jealously towards Sasuke, he felt like his father almost loved him more.

After a while, Itachi heard a knock at his door. He didn't know how long he'd been cooped up in his room. He wondered if it was his father coming to scold him more. Itachi stood up and decided he'd take it like a man, he was surprised to see Anko.

"Hey stud. Ever have sex at a carnival? Bet not." And every other night kept happening like that for him. He had no idea how she got in. But she did, and asked him the same question with a different setting. And they'd have sex at the same area she'd mention. At a carnival.

"Yo stud. Ever have sex at a gift shop at a zoo? Definitely not." At a gift shop, where children were.

"Hiya nerd. Ever have sex in a plaza?" At a plaza.

"Hobo! Fuck in a bouncy house before?" A bouncy castle.

"Loser, F a girl on top of a building roof ever?" And a roof building.

Itachi knew Anko was bad for him. She was like a drug, very addicting. The more he was with her, the more loose he got. The more he smoked, the more he drank, the more sex he had, the more he disobeyed his parents and worried his family. Even Sasuke noticed it. But then that fated day came.

"You're going to Germany?" Itachi was..surprised. Anko was leaving?

"Yeah. For a while." She smiled sweetly. "Let's be honest, this was never going to work out. We both only want a sexual relationship," Speak for yourself, "You're an Uchiha who's 18 and I'm 21. You've got other ladies to finess." She gave him a small kiss on his lips. "See you whenever stud." Anko winked and walked away like that. Out of his life.

Forever.

Itachi didn't know how he felt. Good, bad, relieved, sad?

He figured everyone else would be relieved. Shisui was starting to worry about him, telling him he needed to stop seeing Anko. He didn't even think they were dating through all that they did. She took alot of things from him, his virginity, his innocence incarnate. Neither could he get back, and it'd be a while before everything would get back to normal, because he and his father hadn't talked in months, he cut off almost everyone in his family, and he was more sexually active than Madara at that time. It would take time, but wounds heal. Even wounds left by brunettes that dye their hair purple and mess with you for months and leave you with nothing but a kiss when they move to Germany.

Maybe he'd actually meet that one girl he could keep.

A brunette preferably.

Maybe an Australian.

People really wanted a backstory on Itachi and Anko's relationship, so here it is. I feel like reading this some people wish they ended up together, but sorry Itachi and Izumi forever! Read, review, all that jazz.

~SpaceIsTheLimit~