Misadventures of a Sexualy Frustrated Wall Flower

[FinalFantasyDreamer]

*This is a work in progress. I don't know how smut filled it will be but it's a story that has been banging around in my head for awhile. I am also playing around with formatting and going less dialogue and more in the characters head. You know a wallflower*

Chapter One - First Crush

"I'm going to cum. Fill me up!"

The sultry female voice moaned out.The sounds of sex filled the one studio apartment in downtown Hollywood. His hand gripped his cock. Rubbing furiously he could feel his orgasm rising. Suddenly banging on the wall. He is about to crest. He can feel the orgasm about erupt out of him and a voice from the other side of the wall.

"Stop watching porn and get a girl." 

"Fuck."

He moans his cum spilling out and plastering his keyboard. Instead of hearing the sexy voice begging for his seed he heard his old hag of a neighbor. Sighing he turns it off and starts cleaning his keyboard. Looking up at the clock.

"Fuck work."

Quickly wiping of his cock he pulls up his boxers. Smearing the last bits of cum on the inside. Grabbing his work clothes and a pop-tart he quickly opens his front door. As he heads out the door his neighbor pokes her head into the hallway.

"Masturbating will make you blind young man. God is watching."

She shouts at him as he avoids her eyes. He wants to yell at her and tell her to go fuck herself or shout Satan rules but that is just not him. Instead he avoids this conflict just like all the others. Besides he still has to hand her a rent check at the start of the month.

As he drives to work he can't help but smile. Tayra is working a shift today and after work everyone was going to another coworkers party. He normally avoids parties but he wants to change a little. Mainly he wants her. He wants to grab her ass in those jeans she wears to work and give them a squeeze. Taste those lips on his as he pulls her into a passionate kiss.

"Hey asshole get moving."

The driver behind him shouts. His light had turned green. Shaking his head from the fantasy. Today is going to be the day. The day of action not fantasy. The day of success.

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"Going to the party later?"

"Yeah I am Tayra. Do you want to maybe get some food before the party?"

"Oh umm I am going to dinner with Merrick before. We have kind of started dating."

It was the end of their shift. Heading out to the parking lot he had worked up the courage to ask her out. Though before he can her words hit him like a ton of bricks. Too late, too slow, too passive. He has heard a variation of those words his entire life. Doing his best to brush it off he smiles.

"I am so glad for you guys he seems really cool."

Great now he has to go to the party. At least he won't be alone there. Picking his best friend up at his place they drive through the streets of LA. 'Barkers', not his real name but a nickname based on the spelling of his last name, had been his best friend since college. In fact they would be sharing an apartment but for Barkers pot dealing roommate. He didn't want 'the nerd' as a roommate. His nickname was not a cleaver play on his last name. Everyone loved Barker's and he fit in wherever he went. You know that moment in cheers where Norm enters the room and everyone yells 'Norm'. Well that was Barker. Every where he went people would yell 'Barkers' or 'Barkey'. Part of him would be jealous of his friend, and part of him probably was, but he knew that none of those people actually knew his friend as well as he did. Having his friend there would give him some comfort at the party. 

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His friend was a big hit at the party. It's not like his colleagues didn't like him. They did. He just didn't know how to connect with them socially. A problem Barkers didn't have. Maybe it was the lack of alcohol as liquid courage, he didn't like how it made him feel or the taste. He found himself in the corner nursing a virgin coke. Getting lost in his thoughts. A woman approaches.

"Are you going to state at my tits all night perv?"

"What...no...I was just..."

"Whatever virgin loser."

Laughing she walks away. Not the first time his staring into space has resulted in an interaction like that. Probably won't be the last. Shaking his head to clear his thoughts he scans the room. He hears Tayra laughing and spys her and Merrick. She is looking sexy in a dress that clings to her figure. Merrick rubbing her arm up and down slowly. Looking the other direction he sees Barkers with a large group laughing. He stumbled a little. They have been friends long enough for him to recognize when his friend has hit his limit drinking. Saying goodbye to the party host. Everyone says goodbye. Barkers was an instant hit and everyone wanted to invite him to their next thing.

After seeing his friend home relief washes over him. More than four people is an anxiety inducing crowd for him and he is happy to be home. Picking up his mail he sees the package he had ordered sitting under the pile. Inside was purchased of sex toy. It took him too long to get over the stigma and just order it and here it was. Sitting down at his computer he boots up the Internet. His mind wanders back to the party. Tayra in her dress. The woman's voluptuous cleavage. Dropping his pants he starts looking through his porn images. Rubbing his cock to vanilla images of naked women. There legs parted seductively.  Rubbing his hand dry over his cock he feels the familiar build up. Spying an image that reminds him of Tayra he stops. Opening the box he pulls out the pocket pussy he ordered. It came with a little pack of lube. Pouring it into the hole he fingers the little fleshy opening. Looking at the image that looked like his crush he thrust his cock inside. Shaking he falls to the ground his cock immediately spewing forth his lode. The glands on his cock going in over drive. Panting he had never cum so hard or so fast before. Panting for a minute he slowly pulls his sensitive cock out of his new toy.

 

 

Edited Saturday at 01:13 AM by gb87
Editing and finishing up chapter 1

[FinalFantasyDreamer]

Chapter 2 - Hentai

Time has passed and as they say time heals all. In the end being friends with Tayra was probably better than dating her. While he enjoyed her company they wanted different things in life. So his circle of work friends grew all from his desire to sleep with Tayra. Even the woman from the party, her name he found out after words was Mandy, was different than their original encounter. Turns out she was so drunk she didn't even remember him being there.

One of Barkers roommates had moved out and Barkers roommate, Josh, okayed him moving in. The living situation was tense but luckily Josh was either not home or in his room. It helped that he brought a computer with him. A computer that quickly became a communal one much to his annoyance. 

Barker was super into anime and manga. Something he had limited knowledge on. The only stuff he had ever scene was the old dragon ball or sailor moon stuff on toonami growing up. Reading Barkers manga opened up a whole new world of stories for him.

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One night when everyone was at work he was playing a game on the computer. Getting to a spot he was stuck on he switched to the browser. Scrolling through the browser history he looked for his favorite gaming guide site. Something caught his eye. Anime milf reamed hard. Only one person in this house would watch this. Clicking on the history link a website opened up. A video labeled taboo charming mother starts playing. The animation is of good quality and the female characters voice is sexy and sultry.

Watching her anime tits bouncing up and drown. The moans she would make as she masturbated instantly made him hard. Stroking his dick he quickly watched all the episodes of that ova. Flipping back through the episodes. What scene did he want to finish on?

First episode. Dildo masturbation. Yes that one. Going back to that scene. Watching her character shove the dildo in picks up the pace. His hand swirling around his cock head. In the video she cums moaning out loud. With a grunt he cums. Filling the washcloth on his keyboard. Slumping back in his chair exhausted. Two new fetishes gained in one night. Hentai and Female masturbation.

Edited Monday at 03:25 PM by FinalFantasyDreamer
Editing and finishing chapter 2

[FinalFantasyDreamer]

Chapter 3 - Roommates 

It did not take long for him and his new roommates to get on each other's nerves. Ken and Josh would leave the place a mess and rarely clean after themselves. Then complain to Barker that he did not clean up after himself enough. He tried to fit in and get along with them and to not be socially awkward.

One day he was feeling particularly social. Ken had his girlfriend over and she invited him to join them. Surprising even himself he agreed to smoke pot with them. It probably didn't help that Ken's girlfriend was very cute and he probably would have agreed to anything. Though, it didn't go as expected they quickly disappeared into their room with pizza. Leaving him a little buzzed, hungry, and alone.

That night he awoke hungry and decided to head into the kitchen. He was used to walking in the dark so he didn't turn on any lights. In the kitchen he felt like he could hear some moaning. Peaking his head around the corner he saw Ken and his girlfriend on the couch having sex. As his eyes took in her naked form they made contact with her open eyes. Quickly pulling back his heart racing. Did she see him he wonders. 

"Mmm yes fuck me."

Her moaning seemed to get louder and more descriptive. Daring to look back her eyes are closed now. He can feel his hard cock now. Mesmerized by her tight body getting pounded. Her tits in his hands bouncing with every thrust. Her moans were driving him crazy. Pulling his cock out he starts masturbating. Staring at her tits as she was fucked roughly.

"I'm Cumming"

Her voice pierces the air. Almost on command at her words his cock erupts all over the kitchen floor. Sliding down the wall he catches his breath. After awhile he hears those two head back to Ken's room. Cleaning up  the kitchen floor he heads back to his room. Wondering if she knew he was there.

In the end it didn't really change their opinion or attitude towards him. They just mocked him when he commented that he didn't really think that it did anything for him.

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One day after coming home from work. Exhausted from a long day he opened the door to the apartment. Barker was removing post-it notes from the wall. 

"What's going on?"

"Josh put up notes around the place on all the things he wants us to clean."

That was the last straw. He said nothing day after day about having strangers in the apartment who Josh was dealing his pot too. One of them being Donny a frequent client of Josh's. Who was always stoned on their couch. When Josh's boyfriend suddenly moved in but didn't pay rent or the fucking dog his boyfriend brought with him. God he hated the little yapper and that dog hated him.

No these post-it notes we it. They needed to get out of this place. Luckily his name was never on the lease and he could leave at anytime but that was not true for Barker. Barker was his best friend and as long as he had known him people had taken advantage of him being a nice guy. The nickname was a prime example. Barkers first name was Michael.  It is not the he necessarily disliked liked the nickname Barkers but secretly it did irritate him a little. Not that he would have ever told anyone that.6

"Fuck. Josh is an asshole. We need to get out of here Michael."

"I know."

The only problem was now they not only needed to find a new place but also new roommates. Rent in the Los Angeles area was high and the two of the couldn't afford not having roommates.

-------

Back at work he was complaining to Mandy about the situation. Since the party Mandy had quickly become one his closest acquaintances at work. 

"We need a new place I just don't know anyone that needs roommate." 

"You should ask Tayra. She is currently living with Merrick and his mom and she needs to move out.

A simple suggestion but one that was going to complicate matters. At the time it seemed a no brainer. Merrick was super controlling and he had become close friends with Tayra. Though when she started dating Merrick she saw less of most everyone.

It didn't take long to get Tayra on board. Rounding out the new roommate situation was another coworker of there's, Lacy. A month later the new group of four had signed a lease and moved into a new place. Little did he know that the new situation was not going to go as planned.

Edited yesterday at 06:51 PM by FinalFantasyDreamer
Added some sex

[FinalFantasyDreamer]

Chapter 4 - Relapse 

At first the new rooming situation was smooth sailing. The four of them got along pretty well. Lacy was a little annoying but they were often not home. He was enjoying getting to know Tayra even better. Though this had a negative side to it. He thought he had put those feelings aside but getting to spend more time with her rekindled those feelings. It didn't help that Merrick was over protective of her. To a dangerous level. All of her friends told her she needed to break up with him. Well all but him. He secretly held a desire that maybe she would come to him for comfort after a fight. He would hold her close. Looking into each other's eye they would kiss.

Infact this would become a recurring fantasy of his when he would be home alone. Barkers got a new job that put his working schedule in the evening. Lacy was always out doing something and Tayra was with Merrick. Sitting home alone he delved into exploring his masturbation fetishes. In his exploration of hentai he had discovered futanari. Starting with the doujinshi of Alice and going through the ova Bible Black.

This particular evening he stumbled onto a site filled with futanari doujinshi. Running his hand over his erection he dreamed of seeing a pussy in real life. As he built himself to an orgasm. He realized he left something in his room. As he walked down the hall something caught his eye. A pair of silk panties dropped on the floor on the way into her room. Picking up her panties he couldn't help but feel how soft they were. Looking down at his erection he couldn't help himself. Heading into his room he closed the door 

Imagining her walking into his room. Wearing nothing but those silk red panties. Her little tits jiggling as she walks. Her nipples poking up in the air. Sliding her panties off she climbs on top of him. Wrapping her panties around his cock she began stroking. His hand becomes her hand. The soft fabric felt cool against his skin. 

"I need you...down there"

He imagines her soft voice coming in his heart. Fingers slightly spreading her lips apart. It didn't take long before the panties wrapped around his cock head brought him to climax. Filling the crotch with his cum he looked down at them. Laying there he is embarrassed by his actions. Quickly he threw them into the wash. Desperate to erase his deed before anyone got home.

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One day at work he and Mandy are talking about relationships. Really it's more like Mandy talking about the current guy she is dating. As they are talking Tayra walks in. Joining the conversation. Mandy brings up Merrick and some shitty thing he did to Tayra. Mandy was shipping him and Tayra since day one and disliked Merrick a lot. Tayra quickly changes the subject.

"You know who thinks you're cute? Mary, you should ask her out."

Such a simple sentence with such a heavy connotation. At work he is quite different in his personal life. He is direct, projected confidence, and could care less if the people at work liked him. Apparently Mary really liked it when he ordered her around. That should have been a red flag but because Tayra said it his dick listened. Pretty soon a group date was set up and organized as their first date.

Edited 14 hours ago by FinalFantasyDreamer
End chapter 4

[FinalFantasyDreamer]

Chapter 5 - First Date

Well here he was. Sitting at a table with 15 other people next to his "date". Large crowds overwhelm he why did he agree to this. Of course he had never taken a girl on a date before; not that he would ever admit that to the group. Here he was in his nightmare scenario of a date. A date that was supposed to not feel like a date but sure as hell felt like a date.

His head was spinning, his small talk skills were failing, and all he could do was drink water. One of his more nervous ticks in a restaurant is to drink from his water glass.The biggest problem with this nervous tick is waiters are constantly refilling his glass. Which causes him to drink more water. Which in turn made him have to pee. A lot. 

Finally the night was over. It was suggested he drive Mary home. As a chance to connect. It was an awkward drive home for him. Trying his best to seem confident. All the while feeling awkward and clumsy. To top it off halfway home he had to fucking pee again. While she was going to college she was living at home with her family and her parents were strict. Not wanting to explain anything to anyone she has him drop her off close but not in front of her house. They goodbye and is gone.

Here he was in a part of Los Angeles he knows nothing about. Trying to wrap his head around the night and he only knows one thing. He has to fucking pee real bad. Finally finding a convenient store he deals with his first issue. Getting back in his car his phone buzzed.

"Tonight was nice."

"It was."

"Do want to go out again?"

"Sure."

He smiles. Maybe the night wasn't so bad.

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At work it was a little awkward. She was a private person and didn't want people at work to be in her business. Something he agreed with. They went on a couple more dates but they kind of reached a platonic level. Trying to figure out how to be more forward during public dates was a challenge for him. Mandy's advice was to invite her over for dinner and make her something intimate and watch a movie. 

Grabbing something quick for dinner he quickly ate it in the car. Getting home he pulled out his phone and sent her a quick message inviting her over tomorrow. Then he stomach rumbled. Dinner did not agree with him. Rushing to the bathroom. He quickly pulls down his pants. Making it on time he sighs dinner did not pass through him nicely. Then his phone buzzed.

"I don't think it's going to work out."

"Sorry."

Sitting on the toilet with diarrhea getting dumped this day just couldn't get worse. He didn't know what to do or say. Replying okay he gave up. Part of him knew it wasn't going to work out so he just accepted it. Why was everything with her connected to the bathroom.

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TBC

Edited 4 hours ago by FinalFantasyDreamer
Editing grammar