Bailey Ch. 01

Story Info
Ryan transfers to a new school and meets a girl named Bailey.
11.1k words
4.7
96.2k
290
30

Part 1 of the 3 part series

Updated 06/09/2023
Created 06/23/2019
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

All characters in this story are 18 years of age, or older!

Long time no see peeps! Sorry I've been gone for a while. Life happens sometimes and it's been a busy couple of months for me. Been under some stress and it's caused a pretty lengthy bout of writers-block but, here's chapter 1 of my latest story. Hopefully it won't be too long, before you get to see chapter 2. I hope everyone enjoys.

Starting high school is never easy.

You go in there on the first day, with a stomach ache from anxiety. You try to stick to yourself, and you're paranoid that everyone is looking at you and planning ways to make fun of you and cause you trouble; especially the ones in higher grades. But, eventually all of that wears off and you start to get comfortable...that's why starting high school ALL OVER AGAIN, is actually much harder in the long run.

Especially if you're going into your senior year.

I had just spent 9th through 11th at one school, and now I was transferring to a whole other school, forced to start all over. I had to rebuild everything from the ground up, make all new friends, all new bullies, find new ways to avoid said bullies and of course...I was far from happy about any of that.

Why did I have to do all of this? Because of my mother.

I won't get into what happened there, at least not just yet. In any case, I had moved to live with my father, his new wife and his step-son, Mark. Mark and his mother Jamie were nice people, I had nothing against them...Jamie was certainly nicer than my mom, so I gave dad thumbs up for picking a winner this time.

It also gave me a chance to try and work on my relationship with my father, and actually, potentially get close with him. I just really hated the idea of starting all over at a brand new school.

So there I was, on the first day of my senior year, surrounded by kids that I had never met in my life...and I was feeling like a freshman all over again. Stomach in knots, tapping my foot anxiously, headphones in and blasting my favorite band Taking Back Sunday, in an attempt to keep myself distracted.

So far, everyone had left me alone, which was good.

I kept my hoodie pulled up, and just stayed to myself. I didn't want any trouble from anyone, I just wanted to get through senior year and be done with it all. As I looked around the lunchroom, my eyes fell upon one individual and I couldn't seem to take them off of her...she was beautiful.

In a nerdy sort of way.

She had short hair, dyed black, and was wearing all black. She had a hoodie that said My Chemical Romance on the front, the name of another of my favorite bands. Unlike me though, she was hanging with a rather large group of kids and laughing, as they seemed to all be getting along perfectly fine.

When she looked up and made direct eye contact with me, I jumped and quickly looked away, not wanting to seem like I was staring.

Sure, that girl and her crowd of friends looked like my type of people, with the whole goth/emo kid kind of look but, I didn't want to take any chances.

I had been looking away for nearly a whole minute, when I felt the bench shifting, indicating that someone had sat down beside me...looking up, I was surprised to find that it was that girl.

Oh shit, I thought...here we go..."

She tapped me on the arm and motioned for me to take my headphones off, so I did, though reluctant to do so.

"Whatcha listening to?"

I couldn't believe this! There was a cute girl, actually sitting right next to me that seemed willing to talk to me...that never happened, even at my old school. Sure, I'd had a few friends that were girls but, they weren't really what I would have considered attractive and the ones that were, didn't really have any interest in me like that.

It made me almost a bit paranoid...was she really trying to be nice here, or was it a setup?

"Uh...F-Fall Out Boy," I stammered nervously.

Considering her appearance and the My Chemical Romance hoodie, I'm not sure why but, I was really expecting her to make fun of me for my choice in music...that didn't happen though.

"Oh, I love them!"

She smiled, sliding closer to me on the bench and I began to relax just a little.

"I'm Bailey," she said, introducing herself.

"You're new here, right?"

"Yeah, just transferred from West City High..."

"Ouch," Bailey cringed. "West City...they're pretty rough."

"Yeah," I scoffed. "Tell me about it."

"Is that why you transferred here?"

"Uh, no...not really..."

I hoped she wouldn't press me on the matter. She looked like she was going to though, so just as she opened her mouth to speak, I interrupted and gave her my own name.

"I'm Ryan!"

Bailey smiled and we shook hands. I was a bit surprised to find, that she had a pretty firm handgrip...a bit more firm then most girls might have. "Well, Ryan...me and my friends always hang out at that table over there," she said pointing towards the crowd of students she'd been hanging out with.

"If you want to join us, there's no need to sit over here all alone."

Now again, I was a bit nervous to take such a risk.

Bailey seemed nice enough but, I'd had my fair share of experience with people who tried to act nice, just to end up being your typical jackass bully...I didn't want to walk right into a trap here. Something about Bailey though, made me feel comfortable. It was something in her eyes and that smile, that told me that I was going to be just fine...that I could trust her.

"Okay," I said, hardly recognizing my own voice.

And I did.

I stood up from the table, leaving my little corner and followed her over to her group of friends. Bailey introduced me to everyone, and surprisingly, they all seemed really cool.

There was Nick, who was a bit of a jock but, loved punk rock music. Bands like Rancid, NOFX, Pennywise...they were some of his absolute favorites. I had never met a jock as cool as Nick but, he was pretty damn badass. Totally the opposite of the jocks I had come to know at West City High.

Then there was Nick's brother, Tyler.

Tyler wasn't much of a jock but, he shared the same interest in music as his brother and actually dressed the part too. He had a really big mohawk that was dyed blue and was wearing a leather jacket with all kinds of studs and patches on it.

Then Tyler's girlfriend, Michelle, who was also rocking the whole Punk style. She also had a leather jacket though it didn't have quite as many studs as Tylers, and her hair was dyed pink.

Bailey didn't have time to introduce me to everyone before the bell rang for lunch to end and our next class to begin. Everyone rushed out of the lunch room, and as I made my way towards the exit, Bailey followed close behind.

"Wait up," she called out.

"You know how to get to your next class?"

"Uh...n-not really," I replied, looking at the paper with my roster on it. I handed it to Bailey, who smiled when she read my next class.

"You're in the gym," she said. "I'm in the same class! Come on, let's go together!"

I hated P.E. class, more than any other subject in the entire school! It did make me feel a little better though, knowing that Bailey was in the same class with me.

I'll spare you the boring details of how that period went...let's just say, it consisted of a few basketballs being thrown at my head, and a couple of people calling me various different names. Exactly what I had expected. Nothing like PE class to ruin all the effort you had put into not being noticed by any bullies.

When the day was over though, Bailey caught up with me outside on my way home. She came up behind me, tapping me on the shoulder and I jumped, startled by her hand. I spun around, fully expecting it to be some punk looking to give me a beat down or something but, I sighed in relief when I saw her.

"You have no idea how glad I am to see you," I sighed.

Bailey laughed. "Are you okay? I saw those kids gave you a pretty hard time in gym class today...want me to kick their asses for ya?"

"That would be great," I chuckled. "It's no big deal, really though...trust me, I'm used to being bullied all the time."

That seemed to bring a sad look to Bailey's face but, she brushed it off quickly and sighed. "Well, in any case...I was wondering if maybe you'd like to hang out a little, now that school is out? Maybe we could head back to my house?"

Again, I was stumped.

Not only had I befriended a very cute looking girl today but, she was also inviting me over to her house, to hang out after school...despite the basketballs thrown at my head in gym class, I was actually off to a relatively good start at this new school.

"Uh...s-sure, that...that would be awesome!"

"Great," Bailey cheered. "Let's go!"

She took my hand...her hand was so soft, though I couldn't help once again noticing that very firm grip she seemed to have, as she led me from the schoolyard and in the direction of her house. As we walked, we got to talking about different things that we both liked. I already guessed that we shared the same interests in music but, apparently we both loved the same kind of video games, TV shows, and comic books too!

I knew from the moment I first saw her in the lunchroom, that Bailey was probably a bit of a nerd like me...but, I had never met a cooler nerd than her in my entire life.

By the time we got to her house, I had learned that she liked video games such as Final Fantasy, Grand Theft Auto, Kingdom Hearts and many more of the same games that I loved. Movie wise, she was also a huge Star Wars fan; that was a bonus.

When we got to her place, Bailey led me downstairs to her basement and man, was I surprised at how cool the place looked. The walls were covered in posters for bands, video games, and all sorts of things. There was a 32-inch flat screen TV hanging from the wall, just above a fireplace and a PlayStation 4 connected to it. "This is my girl cave," she said, flopping down on the couch, with a big grin.

"Your girl cave?" I asked, unable to keep from laughing.

"Yeah, my girl cave," she repeated, sitting up.

"Like a man cave but, for a girl. I come down here and hang out with my friends all the time, and even by myself when I don't feel like being in my bedroom."

"And your parents are cool with you hogging the basement like that?"

"Hmm, mom doesn't care...dad's not really in the picture."

I noted the change in her demeanor, as Bailey said that last bit. We had yet another thing in common, so it seemed...my mom wasn't around, and apparently, neither was Bailey's father.

"I understand," I said, sitting down beside her on the couch.

"My mom's not around anymore, either. That's kind of why I moved to this neighborhood and changed schools...I'm living with my father now."

"Polar opposites," Bailey smirked.

"My dad's a jerk and I'm guessing, your mom's a bitch?"

"That's putting it lightly," I laughed.

I still didn't quite want to get into details about it with Bailey...we had only just met.

"It's okay if you don't want to explain," Bailey said, picking up on my reluctance.

"My dad, he uh...well...he was pretty abusive."

"You don't have to-"

"No, it's okay," she interrupted.

"I'm not afraid to talk about it anymore. Dad and I never really got along; I was too different."

"Different?"

Bailey went on to explain that they were constantly fighting because she wasn't quite what she was supposed to be, in her father's opinion. Whatever that meant, I didn't quite understand but, Bailey didn't seem interested in elaborating on that part. In any case, it all came to a head a couple of years ago, when her mother decided it was time to leave her father due to the abuse.

Bailey had not spoken to him since then.

One thing was for sure though, according to her...Bailey had been much happier and living life how she wanted since her mom made the decision to divorce her father.

Not wanting to linger on the subject for too long, because I wasn't liking how it was making Bailey feel, I suggested we sit down and play a couple of games together. That seemed to lighten the mood and Bailey suggested a game of Mario Carts.

We ended up playing games for a couple of hours, before I realized how late it was getting to be, and ended up having to head home for the night. Before I left though, Bailey gave me a big hug and told me she would see me the next day at school.

When I got in that night, dad was sitting on the couch in the living room, along with Jamie, who was resting her head on his shoulder. "How was school," dad asked, as I walked in.

"And why are you coming home so late?"

"Sorry," I said, with a sigh. "I uh...got caught up, is all."

"Caught up?"

I could tell by the look on my father's face, that wasn't really the kind of response that he wanted to hear from me. I was going to have to explain in a bit more detail, where I had been.

"I was just hanging out with a new friend of mine..."

"Oh, that's great," Jamie said, sitting up with a smile.

"See Rob, he's making friends already!"

My dad looked at me suspiciously for a moment, then smiled like Jamie and nodded. "So, is it just a friend or something more?"

"Dad," I sighed, rolling my eyes.

He and Jamie both started laughing at that, as I walked past them and made my way straight upstairs to the room I shared with Mark.

I was hoping Mark was already asleep since I really didn't want to have to talk to him about my first day at school too. Fortunately for me, when I entered the room, I found him in his own bed sound asleep. I laid down and waited to drift off myself but, I couldn't stop thinking about Bailey and my first day, and how well it had actually turned out in the end.

The next day, I was up bright and early and ready for school in no time flat. I practically jogged all the way to the building and met with Bailey just outside on the front steps.

My second day went about as good as the first, with Bailey showing me around more of the school and introducing me to more people. Since I was hanging out with her at the very start of lunch, that made it easy for me to get to know Nick, Tyler, and Michelle a little better.

"So," Nick said with a grin. "Bailey's got a new boyfriend, huh?"

"Shut up," Bailey said, giving Nick a light smack on the shoulder. "He's not my boyfriend!"

"You sure about that?"

I laughed a little, blushing as Nick looked over at me and chuckled. "Don't sweat it, kid," he said, giving me a pat on the back.

"I'm just joking around."

"He's a real jokester this one," Tyler chimed in.

"But, he grows on ya!"

"It's alright," I said. "I can take a joke. I just don't care for basketballs being thrown at my head too much."

"No shit," Tyler said, standing up now.

"I saw that happen yesterday...O'Brien and his boys, right?"

I didn't really know who they were but, I figured Tyler probably knew them well enough that he had the right names.

"I guess so?"

"Listen," Tyler said, getting up closer to me now.

"If those scumbags give you any more shit, let me know...and if you can't find me, go to Nick. One of us will take care of them for you, alright?"

Damn...now I had people willing to look out for me?

"Uh, sure, thanks!"

Bailey smiled at me, as the bell rang and lunch came to an end.

"Hey, by the way, Ryan," Nick said, as he grabbed his bag from the lunch table.

"We're having a party at my place tonight...think you might be able to make it?"

Now, I might have been the shy emo kid but, I had been lucky enough to attend a couple of parties at my old school, with my old friends. It had been a while since I'd been to one though, so I was pretty quick to jump on board with this one. "Sure," I said, eagerly. "I'll be there."

"Awesome," Nick said, and next thing I knew, he was giving me a high five, before walking off towards his next class.

"Well, you're certainly blending in well now," Bailey said.

"Yeah, thanks to you," I replied. "I mean, you're the one who's been introducing me to everyone around here. I had friends at West City High but, there are a lot more cool people here."

"I'm glad you think so," Bailey smiled.

"I'll be at that party tonight too," she said. "Do you wanna meet up and go together?"

"Sure, where at?"

"Well, I always consider the school to be the halfway point between my place and Nick and Tyler's house. So just meet me out front of the schoolyard, and we'll go from there."

I agreed to that, and off to gym class, we went together.

Fortunately, I didn't have too much trouble this time around...those kids who had been throwing balls at me the day before, actually stayed away from me but, I did catch them shooting me some dirty looks a few times. I figured Tyler or Nick must have gone ahead and said something to them...they were keeping their distance but, I could tell they were not happy about it.

I didn't care, as long as they left me alone.

Class ended and we all hit the showers.

I hadn't used the showers the day before since I always hated the idea of washing up in front of a bunch of other guys. Today though, the gym teacher pulled me aside and made it perfectly clear, that I had no choice in the matter. It was hit the showers, or he would hit up my father by phone and that would mean trouble.

The anxious guy that I was, I stayed in the bathroom and waited until everyone else had finished showering and moved out of the locker room, before heading in there myself. I looked around cautiously, before removing my towel and starting towards the shower room. I paused though, as I heard one of the showers still running...was there someone still in there?

I really didn't want to be around anyone in there but, I also didn't want any phone calls to my father taking place, either. I only had about fifteen minutes until my next class, so I was going to have to hurry. With a heavy sigh, I started into the shower room, despite the fact that I knew someone was obviously still in there. When I entered though, my eyes went wide with shock...

It wasn't one of the guys that I had come to know in gym class.

Instead, I found Bailey standing under the shower head, her back turned towards me and completely unaware of my presence. What the hell kind of black magic was this, I asked myself? Why was Bailey in the boys' locker room, let alone the showers?

I got a pretty swift answer to that question when Bailey turned around and looked right over at me, her eyes suddenly wide as saucers just like mine. Now we were both standing there, looking at each other, like deer caught in headlights. My eyes traveled down over her toned body, her breasts smaller than the average girl her age, and as I went below the belt...I realized exactly what she was doing in the boys' locker room.

Bailey had a dick.

It was dangling right between her legs, with water dripping from her heavy balls that were as big as eggs. Even soft, she looked to be about seven or eight inches, so I could only imagine how big she was when fully erect.

"R-Ryan?" She asked as if she couldn't tell for sure whether it was me or not.

She wiped the water from her face, and adjusted her eyes, quickly shutting off the shower and covering herself up.

"I-I just...I'm s-sorry!"

I didn't wait for her to say anything else, before turning and bolting out of the showers and back to the locker room. I grabbed my clothes, quickly putting them back on and rushing off to my next class. I didn't care if the teacher called my father or not, I had just received quite a shock and was struggling to wrap my head around it...Bailey had a penis?

How was that possible?

I never would have guessed that she was a guy, hell, she didn't look anything LIKE a guy! But, girls didn't have what Bailey had between her legs, so what exactly was this all about?

I only had one more class that day, to get through. I spent the entire period wrestling with my mind, trying to make sense of what I had just seen in that shower room. When school ended, I raced out the door and made my way back home as quick as I could. I got home and tried to decide, whether or not I even wanted to go to the party that night...Bailey would be there.