A Shy Teen Goes Too Deep Ch. 01-03

**Author's Note: This is the start of a new story I am writing. I have a lot planned for it coming up. The topics will become more much extreme later in the story, but it starts off tame. I hope you enjoy it. All comments and suggestions are welcome of course.**

CHAPTER 1

I'm sitting in my room trying to do my homework when I feel the urge I get way too often. My hands move down and gently touch my pussy overtop of my jeans. Why am I always so horny? This wasn't the way I was raised, not even close. Above my head is a wooden cross, sitting there, judging me for what I am feeling, what I am doing. My hand pushes down a little harder, grinding my panties on to my clit. I feel shame, but also determination. I can't help myself.

Maybe it was because I'm such a loner, sitting at home by myself so often, not talking, not out doing other things to get my mind off of what I am feeling. Maybe it's because I was brought up in a semi-strict Catholic household, teenage rebellion and all. Or maybe it was just something that happened, a coming together of different circumstances, of different thoughts and actions, that results in me feeling like this so often. My hand slips into my jeans as I lay my books down beside me.

My parents always tried to put the fear of god into me about sex. Growing up it was always a taboo subject, not something that was ever to be discussed, except to tell me not to do it. I wasn't allowed to watch any movies or shows that had sex in it, and even now I would never watch anything like that with them in the same room. They probably wouldn't even like me watching it, period.

I always had to go to Sunday school and listen to the teacher explain to us how sex was to be saved until marriage, how it was for pro-creation, and maybe worst of all, how contraception was forbidden. As the years went on this seemed more and more backwards. Global warming, overpopulation, world hunger, but we are supposed to just keep popping out babies like there is no tomorrow. The way things are going there might not be a tomorrow. Luckily my parents aren't that crazy. Sex was bad, yes. Wait until marriage, yes. Contraceptive? Maybe. We didn't talk about it, but I knew that they were still having sex, I had heard them unfortunately, but I didn't have any brothers or sisters, so something wasn't adding up.

The fact that I don't really have any friends probably helps my relationship with my parents. I almost never ask to have friends over, and never boys, no sleepovers, no parties, no late nights. It makes it easier because I don't ask my parents for things, or do things that they wouldn't approve of. Would they let me have a boy over? No. Good thing I don't ask. Would they let me go to a party? No. So why bring it up? So on and so forth. In a couple of years when I go to college it will be different of course, they won't be there to look over me all the time, but at the same time I will have to hide what I do, if I do anything that is.

I unzip my jeans to give myself easier access to my vagina. My mind wants to say pussy and cunt, but I could never say the words. I have been conditioned. My clit is loving the attention as I also slide a finger into my hole. I'm a virgin if you hadn't guessed. I've never even kissed anyone. It's a little sad when I think about it. I'm 18 and haven't been kissed. Luckily I don't think about it that often.

I grab my phone and begin bringing up my favorite porn. My parents are not very tech savvy and it's extremely easy for me to hide whatever I don't want them to find. They check my phone and laptop once and a while, seeing if I'm on any sites I shouldn't be, from bands they don't approve of to, well, porn of course. They've never found anything, even though I look at porn almost everyday. My fingers type in "siswet" and I get a list of her videos. I watch as she fists her asshole before bringing out massive toys and dildos, sitting on them, devouring them up her almost endless ass. It makes my pussy gush. How can she do that? How can she fit these giant things into her ass? Next I look up "hotkinkyjo" and watch again as she sinks extremely long toys into her ass, I watch as her stomach moves as she is getting fucked, her skinny body outlining the shape of the toy as it moves in and out. It's crazy, and disgusting, and mesmerizing. I can't look away. I love it. I watch another video where a girl is taking two fists up her pussy and moaning like it's the best feeling in the world. I watch another and another, seeing more and more acts that intrigue me. My hand rubs my clit harder, then I slide two fingers into my pussy, fucking myself faster. I can hear my juices sloping away, in and out, in and out, I want to cum so badly, I'm not thinking about anything else, just cumming, just getting off.

*Click... click*

"Fuck," I say outloud, panic coursing through my body. I turn off my phone right away, throwing it onto my chair across the room. I quickly pull up my jeans and do them up, wiping my fingers on the blanket under me. My hands grab my school books from beside me and pull them up. My body scoots back so I'm sitting against the headboard, my mind tries to relax, my face needs to stop looking so red. I hear a creak as my door opens.

"Hey Grace," my mom says as she opened my door.

"Hi Mom," I answer back, looking up at her, hoping she wouldn't notice anything, hoping she couldn't see how red my face was.

"Doing homework?" my mom asks still at my door.

"Ya... history... I have a test tomorrow."

"Ok, well I don't want to disturb you... dinner is in 45 minutes," she says before closing my door.

I let out a sigh as I dropped my books beside me and closed my eyes. That was a lot closer than I had ever wanted. If my parents found out I was masturbating I don't know what would happen. Probably me being shipped off to some kind of covenant or something. OK, maybe not that, but it would be awkward, and I didn't want to go through that.

After a few minutes I went back to studying, trying to focus on the words in front of me, and not the thoughts in my head. Before I knew it, it was dinner, and soon after time to go to sleep. I wouldn't dare to get myself off with my parents home. There was too much risk. I didn't even have a lock on my door. While I lay under my covers I imagine having my holes stretched open like in the videos. It seems weird to me that a virgin would be so interested in huge insertions, but I think that is part of the appeal, it is something so outrageous that it turns me on even more. Whatever the reason for thinking like this doesn't really matter as I don't have any plans on following through. It is a fantasy, nothing more. I drift off to sleep with siswet dancing in my head.

******

The next morning my alarm wakes up as usual. 7am. I hate the morning, I much prefer staying up at night, not that I get too often with my parents checking in. I have to get ready for school so there isn't the option to sleep in unfortunately. My morning routine is always the same, get up, wash my face, brush my teeth, brush my blonde hair and get dressed. No make up, no curling my hair, nothing beyond what is necessary. That was my family's way.

There is no dress code at my school, but if there was I would never be in violation. I put on a pair of very conservative panties, white, and a pair of loose fitting jeans on the bottom. On top I put on a sports bra because that's all I have, a t-shirt that was at least two sizes too big, and a sweater that was droopy and went past my ass. The perfect outfit for someone who doesn't stand out in any way, and hopes to go unnoticed as much as possible. I have dressed like this for as long as I can remember. It was just my style. If you could call it that.

I grabbed my books and bag and headed into the kitchen where my mother had breakfast ready as usual. Today was toast and cereal, nothing special, but at least it was ready to go.

"Busy day today Grace?" my mom asks while pouring herself a cup of coffee at the counter.

I finished a mouthful of cereal before replying, "No, not really, just my history test," before going back for another spoonful.

"Oh, right, well good luck, I'm sure you will do great honey."

"Thanks Mom," I say between another mouthful.

Breakfast ended without any major revelations, my mom left for work and I started my walk to school. We live in a small town, well maybe medium. We have a movie theater and mall, but just barely. No tall buildings or anything like that, one main downtown street. I don't really mind living here, but I definitely have plans to leave for college, somewhere far enough away where I can be myself without feeling like my parents might stop by at any time.

The weather was nice, the sun beaming down as I walked. I was definitely over dressed, but it was what it was. There was no way I would be taking my sweater off. It just wasn't something I did. The more I walked the more my mind wandered. I thought about my dirty secret, my love of extreme stretching porn, how taboo it was, how unlike me it was. No one in my town would be into anything like that I was sure. Everyone here was so vanilla. The church was such a big thing that everyone was part of it, and no-one did anything against it. I could feel my pussy moisten a little as I thought about everything, my white panties getting a little damp. It was exciting to have this feeling while out in public, but I felt safe in my protected outfit, covered with so much material no one could get in.

My school was a typical highschool with typical people. There is no point going into it as I'm sure you have seen enough examples. My main issue with the school was that I didn't have any friends here, well anywhere actually, so my days were lonely, going to class after class without any real interactions. Lunch by myself either in the cafeteria or outside. I usually read a book, or if I was alone looked at my dirty porn links. No one bothered me, I didn't have any bullies, but no one paid attention to me either which was almost worse.

The day flew by without anything out of the ordinary. History was the last class of the day. I sat in my regular seat at the back, pen on the table, ready to start. Our teacher handed out the test sheets and we all began. It was pretty easy for me but I took my time. Since I lacked friends I had plenty of time to study and work on school work. My grades were good. I finished the test about 15 minutes before anyone else but decided to wait until others were done so I didn't draw any attention to myself. Finally with 5 minutes left in class a few others stood up to hand in their paper, I did the same.

I got home an hour or so before my parents usually did meaning I could possibly finish what I started the night before. I had to be quick though, there was no way I wanted to have the same issue as before, with my mom coming home, almost catching me. I jumped onto my bed with my bag and undid the zipper on my jeans. Ripping open my bag I started to dig through it, looking for my phone so I could get an update on my favorite stars. My hand started to squirm around in my bag, pushing my books out of the way, digging deeper until I hit the bottom. No phone. I tried again, pulling out the books and papers from my bag and putting them on the bed beside me, finally flipping my bag upside down dumping everything out. No phone. My heart jumped.

"Fucckkkkkkk..." I said out loud glad my parents weren't home yet, "where the fuck is my phone?" Part of me was worried about losing an expensive thing, but more than that I was worried that someone might have seen my secret. My breathing was increasing as my mind went through the possibilities. What if someone found out? What if they told my parents? I tried to calm down, tried to level out and think things threw.

The more I thought about it the less worried about the second item. My phone was locked. No one could get in. I remembered reading about how Apple wouldn't let anyone unlock their phones. I felt better, but still had to find it regardless. I thought back through the day, where I had my phone, the last time I saw it. Before history class, I checked my messages, I remembered. It must be there, it must have fallen out of my bag.

I did up my jeans, put on my shoes and ran out of the house back towards the school. Maybe running is a little strong, walked quickly. I was lucky the school was still open when I got there, no students, just a teacher or two. I walked through the halls to my history class room, opened the door and went back to my desk. My phone was sitting on top. I was happy to find it, I felt relieved, I wouldn't have to tell my parents I lost my iPhone now. Thank god. That would have been a whole thing. I grabbed it and put it in my pocket and started to walk home.

As the minutes passed my mind was still racing through the last hour, losing my phone, finding my phone, the emotions, I was worn out. Something did bother me though. Why was my phone on my desk? There is no way I put it there. First of all I had a test so no phones. Secondly if it was on my desk I would have seen it and not lost it. Obviously someone found it on the ground and put it there. It must have been under my desk or something. That had to be it. Nothing wrong with that. I felt more at ease again, a little smile creeped on my face as I realized everything would be OK.

I got home and jumped back on my bed. I only had 15 minutes now until my parents got home so no time to do what I wanted to do. I laid my head back on my pillow and closed my eyes for a minute, trying to relax. Reaching into my pants pocket I pulled out my phone unlocking it. I noticed my photos app had a little icon saying there were new pictures. Sometimes my phone adds "stylized" photos to a folder so I didn't think much of it, but I opened it to take a look at them anyway.

There were two new pictures. The first one was a screenshot of my phone, a notification showing on my phone, "New video from Siswet uploaded". My heart stopped. Someone had taken a screenshot of my phone while I was at school. Someone had seen a notification about "Siswet". Did they know who she was? Obviously it didn't matter they could easily look her up. My heart was racing now, I couldn't stop it. My breathing was increasing. I was freaking out. I was so fucked. I flipped to the second picture. I had to know what it was. I needed to know how fucked I was. It was a picture of a piece of paper with a phone number on it and the words, "Text Me".

I closed my phone, closed my eyes, trying to get my breathing under control. I heard the front door being unlocked. I didn't have time to think about this now, I had to turn back into the perfect catholic girl. I let out one last "fuck" under my breath before getting up from my bed and going to say hi to my mom.

CHAPTER 2

What was I going to do? Who was this person? Was it another student? Was it a teacher? And why would they want me to text them? Why wouldn't they just report me? My mind raced as I thought through all of the possibilities.

"Grace? Earth to Grace?" my dad said, waving his hand in front of me.

I shook my head slightly coming back to reality, "sorry, yes?"

"I asked how your test went today."

"Oh, good, it was pretty easy, I finished early actually," I said, poking the vegetables on my plate with my fork, not feeling very hungry.

"Well that's good, we know how hard you study," my dad said as he took another bite of chicken.

My parents went back to their usual small talk, work, friends, church. I sat there trying to eat something but only focused on the pictures. I didn't know what I was going to do.

With dinner done I retreated to my room as usual. I picked up my phone and looked at the pictures again. I couldn't believe I let this happen. Why did I have notifications on? How could I have been so stupid? I flipped back to the picture with the phone number. Should I text? What would happen if I didn't text? There was a reason they hadn't told anyone yet, there was a reason that they asked me to text. I didn't feel like I had much of a choice. I typed the number into my phone and wrote a simple message.

Me: Hello

I waited. What else was I going to do? I tried to open some school books but couldn't focus. I turned on my TV and tried to watch something, but every 5 seconds I looked at my phone to see if there was a message. Nothing. I kept waiting. Time moved slowly. I went to have a shower trying to kill time. I had a cookie and some milk in the kitchen as my parents watched TV in the living room. I gave up and decided to try to sleep even though I wasn't sure I would be able to.

I laid in bed under my covers and turned off my light. As soon as I did I heard a "ping" from my phone. Perfect timing I thought. I grabbed it and checked to see what it was. A message from "unknown"

Unknown: Hi

My hands shook and my heart raced. What do I do now? What do I type back?

Me: Please don't tell anyone

That was all I could come up with. I was so scared that my secret would get out, that my parents would find out. I couldn't afford to screw everything up like that. I hoped they were reasonable.

Unknown: I wouldn't do that

Unknown: Don't worry

I let out a deep breath. That was what I was hoping to hear. But did I trust this random person? Did I know for sure they wouldn't tell anyone?

Me: How do I know for sure?

I waited for a response anxiously.

Unknown: You just have to trust me for now I guess

Unknown: But you are lucky I found it and not someone else

I let that sink in for a minute. Was I lucky?

Me: I guess

Me: Why did you do this?

I was curious. Why take the pictures? Why not just put the phone on the desk? Why not just leave it where it was? There had to be some reason.

Unknown: I was just going to put it on your desk until I saw the notification

Unknown: I didn't think there was anyone else in this hick town that would be into anything like that

Wait. What? I read the messages again, and then a third time. "Anyone ELSE"? Was this person into the same things? The stretching? Suddenly I was excited, but cautious.

Me: Ummm you know who siswet is?

Unknown: Yes, of course, she's amazing!

The quick answer took me by surprise. Was this person waiting by their phone like me?

Me: I'm just surprised that anyone would know her here

Unknown: Well I do

Unknown: Have you heard of hotkinkyjo?

Me: Yes! I love her too

I felt like a giddy school girl. This was the craziest thing. And sadly this was the closest "teen" texting conversation I had ever had. It felt weird, but I liked it.

Unknown: Ya she is amazing

Unknown: I love watching all of them and more

Unknown: What else do you like?

I scrunched up my eyebrows a little confused. What else did I like? Like porn wise?

Me: What do you mean?

Unknown: Like other sex stuff

Me: Oh... well... I don't have much experience

Me: I just found siswet one day and went from there

I waited. I sounded so dumb.

Unknown: I don't have much experience either

Unknown: But I love porn and I wish I could do so much stuff

This person was so open, so different from me.

Me: Like what?

I had to know now.

Unknown: VIDEO LINK

I was surprised that they would send a link, and I was nervous if my parents came in. I connected my headphones, checking for lights outside my door before pressing play. The video started and showed a girl walking through the mall in jeans and a completely transparent shirt, her breasts were completely on show to anyone who looked. She looked so confident.

Me: Wow that's amazing

Me: She is so brave

Unknown: I know I love it I wish I could be like that

Unknown: VIDEO LINK

Unknown: This one is even crazier

I opened the second link and watched a girl walking down a busy street, then up to a bus stop. She had on a coat, but underneath a tight shirt, short skirt and thigh high socks. Then right in front of everyone she squatted down and started peeing. People were walking by, looking at her, and she didn't stop. She kept going, looking like she was having the best time. My mouth fell open. I couldn't believe it.