Jack's Diary Confessions Pt. 01

This story is fictional. This story contains strong language but isn't meant to offend anyone. I intend to make this into a series and possibly write a similar story about another character. Enjoy!

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3.1.2020

20.08

Diary. I turned 18 today. I didn't have a big party or anything just ate some cake my mom had made the night before and caught a movie with my friends.

It's weird because all my classmates are turning 19 this year. One of the cons of skipping a grade. Even Anna is turning 19. She'll probably never look at me the way I look at her. She thinks I'm just a kid. I mean after all we haven't talked in months and for a stupid reason. It was because at some point she started wearing really slutty clothes. I think I'm the only guy in the school who likes her for who she is not her body. Not saying it's not a bonus though.

She wore jeans like she usually does but no shirt. And she came like that to school! That day made me really happy our school doesn't have a dress code. Doesn't mean the teachers liked the outfit very much though. Anyways like I said she had no shirt only a bra and a jacket which was open. This meant that everyone was staring at her tits (and she got really offended not sure what she thought...). And let me just say that her breasts are fucking massive. She's probably a C-cup maybe D and she's only 19. I don't really know why I didn't write about this back then.

I was hard pretty much the whole school day and I'm guessing most of my friends were too. Her tits bounce when she just walks so PE was torture for everyone. When PE ended I looked at all my friends in the locker room and I think everyone was planning on jacking off when they got home. I was too I mean how couldn't I.

I ran home as fast as I could and fortunately I only live about 800 metres from the school. I almost got hit by a car too which would've been unfortunate. I slammed the door shut behind me as soon as I got in to check if anyone was home. Mom and dad seemed to still be at work and my older sister was somewhere but not home. I ran to my room and got fully naked. I threw my phone on my table and threw my blanket on the floor.

I walked to my sister's room and looked for her lotion. I used it and replaced the bottle once in a month. Could by my own but everyone would know what I was using it for. She didn't notice me using it since she didn't really use it so she couldn't realise half of it being gone. I poured some on my still erect penis. I spread it around and went back to my room. I got on the bed and closed my eyes. I started stroking my cock. I was about 6.5 inches long which meant I was fairly average but my dick was pretty thick.

I started jacking off and thinking about Anna. I thought about her body and especially about that day I told you about. I imagined burying my face in those breasts. I imagined meeting with her in the locker room after everyone had left and ripping her bra off. I fantasized about tit-fucking her and having sex with her. All kinds of different scenarios. I was so so so horny. I didn't last more than 5 minutes, I never did while thinking about her actually. I blew a huge load and lay panting on my bed. Fucking her would be a dream come true. I mean sure I wanted to date her and spend time with her but it's pretty clear she doesn't want the same.

I just remembered I haven't written to you about why we stopped talking. It was the day after she had come to school in that one outfit. My friends and I had been in the locker rooms talking about how slutty her outfit was after PE and I had just said something along the lines of "yeah I know". She had found out about that and got really mad and started accusing me of calling her a slut etc. I tried to explain that never happened but she was persistent and we haven't talked since.

Maybe I'll tell you the long version some other time.

7.1.2020

15.55

I have to write about this while the image is still fresh in my mind. So school started again today and Anna was wearing clothes that were revealing to stay at the least. We didn't talk which didn't surprise me but something even better happened. She was wearing jeans again and a bra but she had a shirt on too. It only covered her tits and you could see trough it but a shirt nonetheless. Anyways we had chemistry and she hadn't had time to put on a lab coat yet. One of her friends accidentally bumped into her and spilled some mild acid on her shirt. They started panicking and she took her shirt off. Of course as she took it off her tits were raised too.

When she got it off her tits dropped back down and bounced like crazy. She started quickly wiping her tits as if there was any acid on her (or as if that would help if there was). All the guys watched and a few even had their mouths a little open.

When the day ended I ran home and jacked off to that mental image. I probably will for a solid week. It was the BEST wank of my life. After that I took a shower and now I'm telling you. I'm most likely not gonna do anything else today but jack off to the memory of what had happened.

8.9.2020

16.37

Sooooo I talked to Anna today. Kind of a lot actually. We made up and both of us apologized for what we'd done. She unblocked me on snapchat which was nice. I'm waiting for her to snap me something so I can start a conversation with her. I don't wanna seem to pushy and do it myself since we just started talking again.

21.30

Holy shit she just sent me a fucking nude!! It shows her pressing her tits together and she doesn't even have a bra! I think she sent it to the wrong person. God she really is a slut like everyone says. I don't have time to explain how I took a screenshot without her getting the notification. She just said she's sorry for sending it to the wrong person. Yea as if I would mind.

22.46

Long story short we decided to meet at the locker rooms tomorrow after school had ended and talk about this. Fuck this is so great I'm gonna masturbate to this for so long.

9.1.2020

18.44

OH I NEED TO WRITE ABOUT THIS!!! I LOST MY FUCKING VIRGINITY!! I mean can you believe this I even lost it to Anna! Let me tell you about how all of this happened. So I met her in the school locker rooms like we said we would and we talked. At some point she asked me if I had jacked off to it. I started stuttering and she looked down at my pants. I guess I gotta write the conversation for you to better understand.

"Oh my god you have a boner right now!"

"Wha- what do you mean no I don't."

She pulled my pants down and didn't realise I was going commando. This is where it gets good.

"(Gasp)Oh that's quite big. Jack why the hell do you not have any underwear on!?"

"Did you just say that my dick is big?"

"I don't know, I mean yes it's fucking huge Jack."

"Well I mean your tits aren't exactly small either."

She just looked at me silently as we were standing there. Then she pushed me against the wall and grabbed my dick as she started making out with me. I let out a moan as she started jacking me off. She got on her knees and started blowing me. I knew it would be good but I had no idea how big of an understand that was. My knees almost gave in as she started going faster. When she started getting spit on her face she just wiped that onto my dick and started going even faster. At that point I would've given my life just so she wouldn't stop. She took her shirt and her bra off and kept blowing me.

At that point my knees really did give in. I was in a state of pleasure and confusion. She started laughing and took the rest of her clothes off. She didn't have a remarkable ass but it was average. I looked at her shaven pussy and my jaw dropped.

"Let me blow your mind, big boy."

She told me to go lay on my back and I obeyed. She got on top of me and put my dick in her. I moaned as did she. She started riding me and I almost passed out because it felt so good. After a few minutes I couldn't hold it anymore and told her I was gonna cum. She got off quickly and started sucking me off again. I came in her mouth and she kept going. When my dick was completely milked she swallowed and kissed me.

I watched as she started putting her clothes back on again and got up.

"Anna that was amazing. Why did you just do that?"

"Because you looked like you needed it."

I laughed and sat on the bench. I put my clothes on as well and watched as she strutted out of the door.

"Oh and Jack?"

"What is it?"

"I wanna do this again but nothing else. We're just friends with benefits. You get that?"

"Uhh yeah absolutely."

She laughed and walked out. I can't believe that actually happened. I'll write more some other day.

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I hope you enjoyed this! I will be making more parts but I have no idea how many so I guess we'll just have to see how much stuff I can come up with when I'm horny.