Sydney to the Max Season 4: Episode 5 - Truly Madly Awkward

Written By: L. Little's Fanfic and "Fun But Shy Girl", Based on Characters Created by: Mark Reisman

*Author's Note - This chapter, despite still adhering to this site's rules of what a T-rated story is allowed to contain, does contain some sexual-based material that may be found uncomfortable to view for some readers. Despite the fact that no explicit sexual activity is described in this story, any readers (especially those under 13) that are not comfortable reading this type of story are advised to skip it. Don't worry. The next chapter will fill in all of the gaps of what you missed.

Sydney was sitting in her health class learning about the human body. It started out normal, but then it turned into more than just that, as the day's lesson was becoming more about the male body. As her fellow classmates and herself were listening she had noticed the guys looked embarrassed when it came to the male reproductive system being shown on a monitor before everyone. Sydney felt bad for the boys as she would have been red in the face too if she was a boy sitting in a room with girls. Then she realized it actually would be something which would be her embarrassment soon, since a presentation on the female reproductive system was going to be the next lesson.

The only difference with Sydney though was that she had time to get ready for her embarrassment, since the teacher said that lesson was coming on Friday. Once the bell rang, Sydney noticed how much faster the boys were being at leaving the classroom. She looked up at the teacher briefly and saw they just had that look like this was nothing new to them when it came to this part of the lesson plan. After all, this was Sydney's fifth period class and not only had the teacher done this four other times that day, but also had done the same subject over the years.

When Sydney came home that day she called out to her dad saying she was home. However there was no answer. Sydney thought that her dad was in the backyard for some reason. However she did not see him. Sydney then just shrugged her shoulders and headed upstairs to do her homework in her room. Normally she would do it in the kitchen but she was now starting to feel embarrassed when it came to her Health homework out in the open. As she was doing the health homework, the curiosity bug got to her. She pulled out her phone and began searching images of the male reproductive system. A few links showed up and Sydney clicked on one of them. Suddenly Sydney's eyes widened.

1994:

Max Reynolds woke up one morning in bed feeling very strange. He knew he had a very intense dream of being very intimate with Alisha but wasn't sure how that could affect him physically. Then Max lifted his blanket and bed sheets up and saw a huge bump in his underwear. Scared, Max covered himself with his blanket, worried his mom might see him. After Max woke up a few more times in the morning, he tried putting his hand under his underwear in the morning to solve his problem. However as Max began rubbing his hard penis beneath his underwear, he began to feel great pleasure. The feeling in itself felt good and he just could not stop. Max kept rubbing himself harder, and then as he felt a great pinnacle of pleasure, he felt himself get very wet. At first Max panicked. He thought he did something wrong to his body, and wished his dad was still living with them so he could go to him (even if it would be embarrassing but it would be more so if he went to his mom Judy about this). Then he remembered what he was once taught in health class and it finally dawned on him what just happened.

PRESENT DAY:

Sydney's eyes widened as she saw a video appearing on her cell phone screen of a young man naked and he had a hand going under his underwear pleasuring himself; but... the hand did not belong to the man, but a naked woman who was close to him. As the man pulled his own hand out and began to touch the naked woman all over her body, Sydney's eyes widened. Sydney then laid back on her bed as she took her shirt and pants off, and then began to dig the fingers of her right hand under her panties. As Sydney watched the naked man and woman on her phone pleasure each other, she began to move her fingers faster under her underwear. Soon Sydney feeling great pleasure titled her head back as she said, "Ohhh! OOOOHHHH!" Then Sydney felt herself get very wet as great deal of pleasure took over her body. Sydney then turned off her phone as she said to herself, "Whoa... Just...whoa."

1994:

It was a lazy Saturday and Max wanted to hang out with his best friend Leo. However he had a cold and Max's mom Judy did not want Max to go over there, even if Alisha was there too. So Max just laid in his bed. He would of played with his portable video game but the batteries were dead and he could not find anymore in the house. As for the remote, it only had two batteries when Max needed four. Max did his classic sound of "Gaaa!" in frustration knowing he had nothing to do. As TV went, there was nothing on that was interesting. He wished he had cable and it was too early to watch his favorite network shows. Max then laid back and thought about Alisha. Despite the fact that the two were just friends now, he still felt very attracted to her. He thought about the times she looked most beautiful, and then began to concentrate on the time he saw her at the pool in a revealing pink bikini. Max began to think about all of the high amounts of skin he saw on Alisha's body, including how little her top covered up her breasts.

Then suddenly Max felt a big bulge beneath his underwear. Since he was already feeling hard down below, Max decided to take advantage of the fact that he could now easily pleasure his penis. As Max began to take off his clothes, he knew he could clean up any mess he made from this self-pleasure quickly. He had now done it several times, and had gotten good at cleaning up his 'messes' with his socks. Max's eyes were closed as he started to pleasure himself. He started to go a bit faster as his heart started to race, but then something happened that he did not expect just as he hit the climax of his pleasure. Max glanced over to his bedroom door and saw his mother Judy looking shocked. Judy turned away as she said, "Oh my God Max. I was just gonna see if you were home. I'm so sorry. I should of knocked." Judy quickly closed the door as Max covered himself in a blanket with a look of shame and worry on his face.

PRESENT DAY:

As the days went on Sydney started to pleasure herself before bed. She even started to watch more videos from her phone and saw girls pleasing themselves through the way they let men touch them. Sydney knew she wasn't ready for that just yet but enjoyed watching them. So one day when it was just her at home in the afternoon Sydney wanted to watch another video but the phone was charging and the charge cable wasn't long enough, so she just went without it like she had done most days. Sydney pulled off all her clothes and got started with pleasuring herself.

Now with her eyes closed she was enjoying the pleasures created from her hand caught between the top of her two legs as she used two fingers to pleasure her vagina. Then suddenly Sydney's thoughts were interrupted, when she heard the door to her room open and the voice of her father Max say, "Good night Syd." Then Max suddenly saw Sydney naked on her bed with her right hands moving right between the top of her legs. Sydney then went wide eyed as she saw Max and yelled, "Dad! Close the door!" Max then immediately closed the door and said, "I'm sorry. I should've knocked." Sydney then covered herself in a blanket with a look of shame and worry on her face.

1994:

Max's face went red. He thought he was just going to die right there and then after his mom caught him pleasuring himself in bed. Max then sighed as he slowly cleaned up after himself. When it was time for dinner Max did not want to leave his room. As for Judy, she too felt embarrassed. She wished Max's father still lived with them so he could handle this kind of thing. When she had Max, she never thought she be the one giving Max "The Talk." She had no clue what to say. Her own mother was no help when it came to her own "Talk" as she never gave one. It was just those 'you figure it out' kind of things. However Judy knew that she had to do better. So that evening, she took a deep breath before knocking on Max's bedroom door. Max didn't answer, so Judy decided to begin talking to her son regardless.

"Max... I know this is embarrassing, and again I am sorry I walked in on you when you where well... doing what you did. You are not in any kind of trouble or anything. It's perfectly normal to do what you did." Judy again sighed and shook her head before continuing on. "Well... I think you're now old enough for us to have this conversation. I actually wish your father was here to do it but he's not." Judy waited a bit for Max to respond before continuing again. Max didn't, so Judy continued on.

"I know it just stinks, trust me. It is going to be a bit hard to go through this chat for the both of us. Is it possible I can come in? Or not. It's really up to you and I will just talk through the door if you prefer. You see as you know your body is changing and well…."

"Gaaa!" Max said while laying on his bed.

"I know sweetie, it's uncomfortable to talk about but it needs to be done, you know." Judy's head now resting on the door.

"Mom, I learned about all of it in school already." Max yelled, "I know that I have to use those condoms if I ever decide to... well, you know... with a girl. But don't worry, because I promise I definitely won't be doing it for a long time."

"Oh. Well okay Max. I know when it comes time to do what you must've been day dreaming about for real one day, I know you will make the right decision. Again, it's normal what you did but... maybe do it in the bathroom next time since at least you can use the soap to clean up your..."

"Gaaaa!" Max fell back onto his bed.

"Sorry, sorry. Um I hope you could come out soon for dinner."

Judy then headed away from Max's room.

PRESENT DAY:

Sydney did not know how long it has been since her father caught her pleasuring herself. She did not know what her dad would do. As for Max he had no clue how he should handle this kind of thing. He wished his wife Alisha was still alive to help with this kind of thing. He wanted his mom to help with this instead, but she was traveling outside of the country, and outside of cell service right now. Max began to wonder what set Sydney off to do what he saw her do. Was it because she was just curious about her body... or was she trying to act out something she saw online? Max wanted to panic, but knew he had to stay calm. Max for one did not want to make dinner until he had an important talk with Sydney though. So Max took a deep breath before knocking on Sydney's door.

"Syd, can we please talk?" Max waited a bit before he continued. "First off, I am again sorry for... well... you know. It's completely normal for someone to explore their body. I mean, I know you're at that stage where you know your body is going through those 'special' kind of changes. Look... we've been through rough times before, and I'm sure we can get through this one too."

Sydney's face was now buried into her pillow wanting this conversation to stop and just wait for her grandmother to somehow come back from her vacation super early and deal with this.

"Look Syd... I don't know if you've seen certain things while on your phone but... if you have... look... the kind of videos where you see people having sex online... they're just acting. It's a fantasy that's not like the real thing, and... look, if you are gonna keep doing what I saw you doing... I'd rather you focus your thoughts on what you really want one day, rather than a fantasy that's not your own. So when it comes time that you think you're ready to do that kind of thing for real…"

Sydney then suddenly released her face from her pillow as she yelled, "Dad, I've taken Sex Ed and Grandma gave me the talk a year ago! Are you satisfied!?"

"Yeah, um... good talk." Max breathed a sigh of relief as he walked away.

1994:

Max and Leo were both walking home from school together as Leo said, "So Max, we hanging out at your place this afternoon?" Max shook in horror slightly as he said, "Um... I think me and my mom need just a little bit of time off from each other for the next few afternoons. How about your place?" Then Leo said, "Or we could see if Alisha will let us hang with her. We are about to pass her house, and her older sister did just get a new video game system." Max then said, "Eh, why not?" Then as Max and Leo approached Alisha's house, they saw a teenage boy leaving the house. A confused Max then said, "Wait. Is that Alisha's boyfriend Kevin?" Leo looking concerned said, "What was he doing there? None of my other cousins are supposed to be home right now, and you know my Aunt Maya doesn't like it when Alisha has company over without family around." Then Max looked concerned as he and Leo approached the front door and knocked.

Alisha then opened the door wearing just a bath robe as she looked surprised and said, "Oh! Hey guys. I was... about to take a shower. What are you both doing here?" Leo looking skeptical said, "We came to see if you wanted to play video games. But what was Kevin doing here?" Then Alisha looking a bit nervous said, "We were... just going over our math homework together. Nothing else." Then a concerned Leo said, "And so now after doing hard math homework, you need to take a shower?" Alisha looking more nervous now said, "Well... hard math problems make you sweat. Anyway, sorry, I'm gonna be busy all afternoon. Lets play games later. I..." Suddenly Alisha had a sick look on her face as she bent down slightly. A concerned looking Max said "Alisha, you okay?" Alisha then said, "Yeah. Just feeling sick again." Max looking more concerned now said, "Alisha, you should go see a doctor. You've been running to the bathroom throwing up all week now." Alisha sighed and said, "Max, Leo, just... leave me alone for now!" Alisha then shut the door as Max and Leo were both left with worried looks on their faces.

PRESENT DAY:

Sydney and Harry were sitting on a bench by the lake as Harry said, "Well I'm glad you got that awkward conversation out of the way with your dad sooner, rather than later." Sydney sighed as she said, "Yeah. I mean... I'm glad my dad wanted to be helpful, but still... talk about awkward." Harry smirked as he said, "Still. It's amazing your dad didn't come down on you by punishing you or taking away all your electronics. I remember I once accidentally stumbled upon some 'adult videos' by mistake when I was nine years old right when my parents walked in, and I wasn't allowed to use a computer again for nearly a year." Sydney looked surprised as she said, "Dang." Harry nodded and said, "Yeah. But your dad trusts you Sydney. I mean, he knows you wouldn't do anything dangerous or drastic." Sydney suddenly had a look on her face as she said, "Well... I mean... maybe I don't want to be completely safe. Maybe... I should be a bit more bold." Harry looking confused said, "What do you mean?" Sydney then took a deep breath and said, "Well, I've been thinking about what I really want, and... Harry... we've known each other since we were little, and I... I love you. I've shared my thoughts, feelings, and dreams of the future with you Harry, but... there's still one thing I haven't shared with you, and..." Harry still looking confused said, "Sydney, what are you trying to say?" Sydney then took a deep breath and said, "Harry... I want to have sex with you."

TO BE CONTINUED...

Coming Soon:

*Episode 6 - Sex and the Confusion - When two young characters begin to plan to have sex for the first time very soon, important conversations and surprising secrets are revealed.

*Episode 7 - My So Called Pregnancy - When the last person anyone expected to gets pregnant, everything changes.

*Episode 8 - Bitter Sweet Family - When Sydney and Sophia's families decide to finally have a vacation together, drama erupts when Sophia's brother shows up.