Misadventures of a Sexualy Frustrated Wall Flower

[FinalFantasyDreamer]

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.

----------------

"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. 

---------------

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 July 15 by FinalFantasyDreamer
Removed temporary header

[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.

---------

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 July 7 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.

---------

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 was 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.

"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 July 13 by FinalFantasyDreamer
Fixing errors 😞

[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.

---------

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 July 9 by FinalFantasyDreamer
End chapter 4

[FinalFantasyDreamer]

Chapter 5 - First Girlfriend 

Well here he was. Sitting at a table with 15 other people next to his "date". Large crowds overwhelm him. 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.

----------

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.

---------

He expected things at work to be awkward but she just kind of avoided him. Which was fine for him. Dodging awkward conversations was his specialty. Mandy did her best to try and cheer him up but honestly for his first real girlfriend it wasn't bad. He knew their relationship had a time limit and was going to end some time (he also still had a foolish candle for Tayra). He had just wished he could have gone farther than it had before it ended. Especially because the guy she dated next, Martino, was a real piece of work. She had no problem with people knowing she was dating that prick. If that was her type maybe he dodged a bullet.

Additionally, he had started a new job in his desired field. Which meant cutting back his hours at the old job and spending less time with those work friends. Consequently, he was home alone a lot more. Being young, always horny, and a virgin he ended up spending time exploring the darker corners of the Internet. He tried not to spend money on porn, really he wonders why people would, but he had been seeing a lot of those pop-ups for cam girls. Curious and feeling lonely from the breakup he signs up.

Scrolling through the options he finds an attractive blond lady. 

"What's up baby. What would you like to see?"

He had thought about this for awhile. Most of his fetishes he could watch on video but here was a live woman.

"Could you stuff your panties in your pussy?"

The request throws the model slightly but she knows how to use her time. Slowly she pulls off her panties. Grabbing a dildo she teased the outside of pussy. Before sliding it in. Getting her pussy nice and slick she starts pushing her panties in. His hand gripping his cock hard he can't take his eyes off her glistening pussy. She lets out a moan as the panties disappear inside her. Picking the dildo up she starts fucking her panty stuffed pussy. Letting out a big moan she cums. Pulling out her panties she gives them a suck. This pushes him over the edge. Cumming hard he sprays his load all over. Panting hard she messages

"Times up. That was fun big boy."

Cleaning himself up he wonders was that worth it? Going to bed he dreamt that night of those pussy soaked panties being Tayra's 

 

Edited July 13 by FinalFantasyDreamer
Always editing errors 😔

[FinalFantasyDreamer]

Chapter Six - Online Dating 

What had started out as a decent rooming situation had started to sour. Lacy was constantly short on rent, missing rent for the month, or paying them back late. He would have kicked her out after the first month but because he was hung up on Tayra, her BFF, he let it go on too long. Covering her rent and expecting money that never came. Finally it was to much even Lacy knew she had to move out. Tayra unable to cover an increase in rent also moved out at the same time.

Lacy moving out and Tayra going to move back in with Merrick was like a wakeup call. Realizing maybe it wasn't Tayra he was hung up on maybe just the hope that he could find companionship.

Turning to the Internet he created an online dating profile. Figuring what could it hurt he didn't know any other way to meet women.

-----

His adventure into online dating didn't go as well as he hoped. Probably because he always held a little too much back online. Though it's not like he didn't go on dates through the various applications. Of course he was cat-fished a couple of times by bots as well.

He did end up on a couple of dates through the apps. One was an absolutely disaster date where getting coffee turned into walking her dog a for like fifteen minutes. The date became a fast paced hike through a park. Even though he didn't particularly enjoy being around dogs he still threw out the idea of a second date.

"No thank you. It was a pleasant time we just didn't click."

A phrase he was getting used to hearing. That's okay life was about the rejection. Lots and lots of rejection. Undeterred he tried them all.

That night sitting at home scrolling through his empty inbox he pulls open a familiar tab. Watching some hentai in the background he pulls open his gaming site. He sees a friend of his online. Throwing them a message to say hi. They have chatted back and forth about video games for about two months now. There reply pops up.

"Hey what are you up to tonight."

"Just watching some videos."

"You watching some porn or something lol."

"Yes."

What was he doing. Why did he reply with a yes. They were probably going to block him now. Embarrassed he didn't know what to do. Typing and erasing a follow up message he was paralyzed on what to do. Then there reply came through.

"Really? That's kind of hot."

He was shocked they were not embarrassed by his omission. In fact what unfolded was one of the most unfiltered discussions he had ever had about porn, kinks, masturbation habits, nothing was off the table. 

"Have you ever edged?

"Edged?"

The word seemed innocent enough but it was about to open a new door for him. His online friend proceed to lead him through masturbating, or JOI as he later learned it to be. Stroking his cock his eyes glued to massages that came through. Doing his best one handed typing as he stroked to the number given.

"Now get to the edge and hold it."

"Fuck."

He typed desperate to cum but holding back.

"Now relax and rest..."

"And edge."

Unable to focus on anything other then holding back he only typed quick responses to when they asked a question. He groaned in pleasure as he was repeatedly brought to the edge but not allowed to cum.

"Now beg for release."

"Please... please let me cum."

"Cum all over me sexy."

As those words flashed across the screen he let out a loud groan. Cumming harder then he has ever before. His cum hitting the computer and screen as it erupted from his cock.

"Fuck..."

Was all he could type.

"Glad to be of help sexy. Talk to you later.

 

Edited July 13 by FinalFantasyDreamer
Finished chapter and some editing

[FinalFantasyDreamer]

Chapter Seven - Leaving LA

After those two moved out life continued on at a rapid but monotonous pace. After dealing with fake profile after fake profile he had given up on online dating and threw himself into work. Keeping his old job on the weekends he was working shifts everyday. 

One day he was stocking film in the vault and feeling exhausted.

"Is this my life now."

He spoke into the vast empty vault. Reading barcode after barcode trying to find the right one. He had just got back from visiting his family who lived in another state. His brothers family was about to grow again with another child. Part of him was jealous Not of his brothers wife she was an awful human whom he did not get along with. No he was jealous of the chance his brother had to be a father. He wanted nothing more than to have that opportunity himself. In the end he realized he wanted to be closer to his family, his nieces and nephews. To be a part of their lives as they grew up.

After discussing his options with those close to him he had decided to go back to school in his hometown for his masters degree. After a farewell party with all the friends he had made in Los Angeles his time in LA was coming to a close.

--------

A couple nights before the move he was on his computer and logged on to the gaming site. Seeing his online friend logged in shot him a message. Pretty soon they were chatting about deeply about life, relationships, and porn. He found himself opening up about his situation, fears, and life in general. When the topic of dating came up his friend decided to try an experiment with him 

"Okay last time I played the girl and gave you instructions. This time you be the girl and give me instructions."

 He was a little hesitant but decided why not. He started of describing his 'female' body. Describing her stiff nipples and wet panties. Pretty soon he was delivering instructions to his friend. His hand lightly grazing the underside of the shaft. Tongue teasing the glands. Having his friend run his shaft up and down bringing him to an edge. Then stopping him. Distracting him with side chatter and making his cock go soft. Then quickly back to stroking. Back to the edge.

This went on for awhile. Edging the person through the Internet until he squirmed and begged.

"I need to cum so bad."

The pleading message appeared in the chat.

"Then cum."

"Fucckkk. Yesss."

His friend cumming at his command was very arousing for him. He himself was rock hard and he hadn't even pulled his pants down or touched himself.

"That was intense dude. You may be a sub when it comes to relationships but sexually you are very dom."

Those words echoed around his head. It made a lot of sense to him. Here he was a socially submissive wallflower but what he was attracted to was submissive partners.

After the move and a broken computer he forgot all about that gaming chat site. Years later he tried to find it again but it had shut down a while ago. He never got to thank his online friend and the exploration of his sexual desires with another human. Though he would remember him from time to time and hope all was well.

Edited July 16 by FinalFantasyDreamer
Light formatting

[FinalFantasyDreamer]

Chapter 7 - College 2.0

It was a very different experience for him this time around at college. The first time with his degree most everyone was near his age. When he first went to college he lived on campus, was exploring life in a new city, and working towards becoming an adult.

Now it was with a real purpose. He was now older then a lot of his classmates. Had didn't have much in common with a lot of his classmates. That and he found it was hundred times easier. Settling into an apartment in town he began adjusting to his new situation. He enjoyed being closer to his family and being able to visit them more frequently. His second college days went quickly and he began looking for a job with his master's degree.

--------

Dating in those days was much the same just a smaller dating pool in a smaller town. Trying again at online dating he went on a few first dates. 

After one night of a particularly rough day in classes and striking out online. Laying in bed he hears his neighbors enter their room. The apartments walls were not that thin. They were just that loud. 

"I have been a bad girl pee on me daddy.

Did he hear that right? Sitting up in bed he places his ear to the wall. The sound of water hitting a tarp. Sitting in bed listening to his neighbors fuck and their fetishes got him very aroused. He had seen them around the complex. They were not what he would have considered attractive but their freedom to explore their kinks he found very attractive.

Laying in bed he could hear the start of his thrusting. Their headboard hitting the wall. Her moaning picking up in intensity. Her moaning sounded over the top but his grunting was as well. It was almost like a game they were playing. Stroking his cock he listened to the sounds of their passionate play. 

As there pace picked up so did his. Edging whenever he felt close. Wanting to cum with them. Breathing hard his body shaking. Desperate for release.

"I'm cumming baby!"

Her moans sent lightning through his body. Releasing his cum his body tense up as it spills forth. Cum coating his stomach he lays there panting. Thanks. He thinks to himself. He needed that. Couple kinks another new fetish to add to his searches.

[FinalFantasyDreamer]

Chapter 8 - Matchmaking 

As his second round of college days comes to a close rather quickly. Entering his new fields job market was a little rough at first but he quickly found his footing and was earning a stable income. Frustrated with the dating apps he was doing an online search for how people dated in his town. As someone that doesn't drink bars were a bust. Wasn't a religious person so church was a bust. Dating co-workers been there tried that pass. Finding that Special Someone a match making service in his region. Local women, set up a consultation meeting first, no online profiles, real feedback to improve. The membership fee was higher than the apps but maybe he will have better luck.

The initial consultation went well. She matched him up and sent him on several dates. Most of the first date were no different then before. The feedback was always some variation of the same

"I had a nice time we just didn't seem to click."

Okay nothing new here but he wasn't going to be discouraged. Dating is hard and rejection is something he has dealt with his whole life. 

"Just be more confident."

Easy for her to say but apparently difficult for him to put into practice. Then came Fae.

--------

Their first date was okay. He walked away thinking it was pleasant but he was sure that would be it. Texting the matchmaker. He told her the date went okay and he would be interested in a second date. Staring at his phone he waited for her response. She replies back that yes she would be open to a second date. He was over the moon. His second second date was set up.

Some of tension from their first date was gone. Though he was still pretty nervous. They seemed to connect over some shared interests. She said that his non drinking was actually a thing she found attractive. That and she found his eyes beautiful.

Dating was not as easy as that second date. Between their work schedules not being in sync and her kids. Dates were few and far between. They pushed forward though. Early on they decided to not play games. Be honest with their thoughts and feelings because they couldn't afford waisting time. After an awkward third date he knew the moment to kiss was coming unsure of himself he left it there.

"Sorry about after the date...I have never kissed someone before and I didn't know what to do."

"..."

Those dots felt like an eternity.

"Oh, okay well thanks for letting me know..."

Their conversation opened up from there. He talked about his lack dating and sexual history. She was fairly open minded and understanding.

------

He wasn't going to let it happen again. Confidence. That's what people keep telling be confident. As their next date winds down. He walks her to her car. Standing there he leans forward. There lips lock. He feels her lips part and her tongue enter his mouth as his enters hers. He lost track of how long they were standing out there kissing. It felt like eternity but in reality it was brief.

"See it's not that hard. See you later."

With that she got in her car and left. He could still feel her lips on his as he drove home. Pulling out his phone he shoots a quick text.

"Dinner was fun we should do it again sometime."

"Sounds like a plan."

Looking at his phone he pulls out a picture of her they snapped on a previous date. Felling the hormones of the kiss he pulls down his pants. Stroking himself he looks into her pictures eyes.

"I think I am falling for you Fae."

With a grunt he cums into his Kleenex. Next time he will keep being decisive.

Edited July 14 by FinalFantasyDreamer
Cleaning up mistakes

[FinalFantasyDreamer]

Chapter 9 - Second Base

Even though they live in the same town their schedules rarely lined up. They would go on a fr dates here or there but often not. Dates proposed and then were shifted to another weekend or put off entirely. Sometimes it felt like everything was happening at the worst moment possible. So their relationship became almost like long distance one.

They texted frequently but she expressed doubts about the relationship succeeding. He wanted to work through these moments. Of course he had doubts of his own. Did they get along enough for the relationship to succeed or was he just horny and was wanting to get laid and she seemed willing. He had seen the later enough times to know that was a possibility.

--------

Six months into dating with this kind of on again off again mentality. A new date is put on the books. Dinner at his place the date is set. No a last minute change here friend showed up with wine dinner at her place with a friend or cancel. 

Dinner with her friend was pleasant. Her friends kid had come over to play and they grabbed take out Chinese food. As the evening wore on he gained the approval of at least one of the kids. Her friend said good bye for the night and Fae put her kids to bed.

"Wait here don't go anywhere."

Alone at last. As she came back into the living room they sat back down on the couch. Putting her legs up he started rubbing them. Soon the rubbing turned to kissing. His mouth moving down to her neck. She lets out a soft moan. Being confident his hands slide under her shirt. She had taken off her bra. Grasping her breasts he gave them a squeeze. Lifting her shirt up he moves down her body. Gently kissing her nipple as he made his way to her stomach. His hand slides up her inner thigh. He gently rubs her pussy through her pants.

"No...not here not on the couch...not now."

"Okay."

They kiss for a little bit longer before separating.

"I had fun. Let's do it again sometime."

"It's a date."

Edited July 15 by FinalFantasyDreamer
Fixing errors

[FinalFantasyDreamer]

Chapter 10 - Break Up

Sometimes for every good date he felt they went on he did, or more likely didn't do, something that made their next date end on a low note. He didn't know if his feelings for her were connected to enjoying spending time with her or was this another Tayra. He saw the hope of sex so he pursued.

Eventually in the end it didn't matter. After coming back from a trip she texted.

"We need to talk."

Arriving at her house she greeted him not with a smile but a cold hug. They passed some pleasantries together before an awkward pause. Then the words he knew were coming.

"I don't think this is working out."

There conversation turned down the avenue of discourse much like any couple breaking up. The "it's not you it's me", "I am not ready for more", "you deserve a girl that can give you your future family", ect... Feeling lost he tried to find the reasons to stay together but it was useless. The things she originally found endearing became the reasons why she wanted end it.

She felt judged by his choice not to drink when she wanted to drink, even though he had never told her or tried to stop her from drinking. Her sons father, and his family, is very religious and she doesn't know how religion fits into her life. The fact they had not had sex yet because as she put it he wasn't trying hard enough. She decided he must assume she was easy because she had kids. That last part baffled him he didn't know what to say other than.

"I guess it is over."

-------

He had never experienced heartbreak before but he felt it now. After a few days and some deep chats with friends he started to move on. He tried to jump back into dating with some dates with the matchmaking service but it was a little to soon for that. Leading to some awkward dates.

At home he self-soothed by exploring his kinks. Scrolling online to female masturbation videos he discovered something called hysterical literature. Watching videos of these women desperate to focus on their task and not cum excited him.

From there, he discovered exhibitionist videos of women and remote control vibrators. They would be in public using remote controlled vibrators inside their pussies. They would be at stores, restaurants, or anywhere in public.

Finding one pornstar that had a slight resemblance to Fae, long brown hair, slim body, perky tits. She would read stories while trying not to cum. He was hooked.

Clicking on her videos he would spend time browsing them finding the one he liked best to cum to. Pulling down his pants he started stroking. Closing his eyes and listening to her moaning. He would slowly feel every inch of his cock. Here next video was a JOI video. It started auto playing while he was stroking.

"Now put in your plug like a good boy."

He had played with his asshole before with some fingers but never very deep. Pausing the video. He looked around he didn't own any toys like that but he was very horny. Spying a pen on his desk it had a little silicon christmas light esque bulb on it. That looked kinda like a plug. Walking over he squeezed the squishy light portion. It was supposed to light up but the batteries inside it probably died long ago. Looking back at the paused video he threw caution to the wind. Hitting play on the video he grabbed his lube.

"Now gently slide it inside you as you stroke."

The video instructed. Lubing up the bulb portion he gently slid it in. His eyes went wide as his other hand grasped his cock.

"Fuckkk."

He moaned feeling an intense pleasure inside him. He could feel his cock despite to cum as every nerve in his ass was alive. Stroking his cock he did his best to hold back. The moans coming from the video as she fucked herself combined with this new sensation was to much. His cock squirted its load out and onto his chest.

He lay there breathing hard. Covered in his cum with his ass clenching around the pen. He moans as he relaxes and pulls the pen out. Panting he lays in his room.

"Fuck that was intense."

He gasps into the empty room.

Edited July 15 by FinalFantasyDreamer
Fixing errors

[FinalFantasyDreamer]

Chapter 11 - Sexting 

After the break up he threw himself into work. Letting work and his family sustain him. The eligible dates through the matchmaking service seemed to slowly happen less and less. Slowly though he started to want to put himself out there.

Trying online dating again he decided to put everything out there. His struggle to connect with people. His desire for what he is looking for. Opening up the search radius as wide as it could go. He knew by doing this the number of matches he would get would be fewer.

One evening he gets a response from one of his messages. He had asked her what she was currently reading.

"Right now I am reading an mystery novel by Agatha Christie."

"No way same here."

There shared connection lead into a long conversation well into the night. Nothing was off limits. They talked about being shy, their respective ex's, their family, and interests they shared or didn't. He had never connected so deeply with someone before.

That nights conversation lead into others. Pretty soon they were checking in with each other nightly. These digital dates were about it as they lived far away from each other.

--------

After about two weeks of this and they switched from daily texts to video calls. Her face came on the screen

"You look beautiful today."

"Thanks I did it for a special person."

"Who?"

Standing up she slowly reaches under her shirt. Slipping her bra off she displays it to him before dropping it to the floor. As her shirt falls back down he can see her hard nipples poking through the sheet fabric. Giving a little spin in her white mini skirt he can see she isn't wearing anything under it.

"Your turn lose the shirt."

Blushing he takes of his shirt. His hairy chest exposed to the air. Normally she was so shy but today he was loving the dominant side of her.

"Mmm. Hello sexy I want to run my hands through all your hair."

Running her hands down her chest she lets out a little moan. Gripping her shirt she peels it off letting her tits free. Swinging slightly. Dropping his pants his erection is in full view of the camera. He starts stroking as she sits down. Flipping her skirt up she sits back down. Licking a finger she slowly enters inside her slick bald pussy.

The dirty talk continues as they stroke themselves. Building towards the orgasm he lets out a brief groan.

"I'm going to cum."

"Me too."

Climaxing together the both fall backwards. Gasping he lets out a moan. His words shaky

"That was amazing."

"Thanks. When I get horny I kind of throw caution to the wind."

She blushes her shy side taking back over. They chat sitting in their rooms buck naked for a while longer. The digital equivalent of pillow talk.

Edited July 15 by FinalFantasyDreamer
Fixing errors 😔

[FinalFantasyDreamer]

Chapter 12 - Surprise 

Opening up his phone he smiles. He can't wait these days to see messages from her.

"I made kind of an impulsive decision."

"What kind?"

"I bought a plane ticket."

"That's cool where are you going?"

"To you... I hope that's okay. I arrive tomorrow."

He is stunned she is coming here. He had thought about trying to meet up. Though, it had only been a month. It seemed like such a big step.

As he drove to the airport he had never be so nervous in his life. He didn't think it would be happening so fast. Pulling up he spies her by the arrival gate. There she was standing in that pretty white skirt and top from that night. Her long hair blowing in the wind. He pulled up and got out. She gave him a big smile and a hug. He could feel she wasn't wearing a bra as her nipples pressed into his chest. Quickly putting her carry in in the car they get in.

"Be bold."

He thinks to himself as they both reach over towards each other. This kiss felt different then before. Kissing her felt right.

"Move along."

The airport attendant yelled at them. Blushing he put the car into drive. 

"Umm I have a surprise for you."

Turning towards her he notices she has lifted up her skirt. Not only was she not wearing any panties she has a lush vibrator sticking out of her pussy. Pulling out her phone she presses a button. It buzzes to life. She lets out a low moan.

"I...put...it in...on the plane."

She gasps her words out as she brings the vibrations down.

"I knew I needed a little courage so I have been edging since the plane."

Glancing at her eyes he sees the love and lust in there. Stepping on the gas he couldn't wait to get home.

-----

Bursting through the door they couldn't keep there hands off each other. It was like a scene out of a romcom. Their hands ripping clothes off. Kicking shoes and socks as they tumble to the bedroom.

Laying her down on the bed his mouth wanted to taste every inch of her. His beared tickling the inside of her thigh. She squirms under him. He reaches her pussy giving it a lick. Hitting the toy still inside her he pulls it out. Enveloping it in his mouth he savours her taste.

"I need you inside me. Now."

Her voice a mixture of pleading and demanding. He climbs on top of her. Her hand grasping his cock she helps guide it in. Simultaneously they gasp. He had never expected it to feel so amazing. Her warm pussy is gripping his cock in a way he never expected. Looking at her. There eyes lock. He can't move. The desire to cum is strong. It's taking everything to hold it back.

"Sorry. Can't hold it I'm..."

"Shhh it's okay. I need you cum in me now."

Her sultry voice. Her simple permission. Her burning desire. It's all too much for him. With a shake his cock unloads inside her pussy. Collapsing on top of her. He tries to gather his thoughts.

"I'm sorry it was so quick."

"It's okay we have lots of time to practice together."

Kissing her. Their tongues locking together. He didn't believe in souls mates or destiny but if he did he knows he just found his.

[FinalFantasyDreamer]

Epilogue 

It didn't take them long to figure out they never wanted to leave each other. The following weekend they were making plans for her to move in and six months later they were married. One year later and their first child was on the way. Looking back he wouldn't have traded any of those experiences because they made him who he was. His first crush, his first girlfriend, his first kiss, his first sexting friend. Today, even with their little family growing, they find a little time to explore their kinks together.

--------

Thank you for all those that read and enjoyed his story. His story is a story that has been rattling in my head for several years now. It went through a lot of iterations in my head over the years but the exploration of relationships, sex, and being introverted was always at it's core. If any passages resonate with you feel free to drop a line.

Edited July 16 by FinalFantasyDreamer
Fixing typo