Learning to Fly Chapter 4

Learning to Fly

A story by Jesse James (JesseJamesNiftyEmail@Gmail.com) © 2019

Disclaimer: This story, at points, involves sexual acts between minors. If this is illegal wherever you live, please stop reading now. I, nor Nifty, are responsible for any legal ramifications if you continue. You’ve been warned.

I would like to make a special shout out to XPud for helping me with formatting, editing and suggestions as well as being a truly great mentor.

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Chapter 4

Well hell didn't come immediately fortunately. Me and Caleb made it back to class and I was able to convince Mrs. Price I slipped on something wet (didn't specify what. Wanted her to use her imagination. She teaches English. She has one.) and it hurt. Hence why I took so long. I even hammed it up some by clutching my side, which was still somewhat sore FYI, to sell my story. Call me Robert motherfuckin' Downey!

Caleb kept his promise also. Even if he kept looking at me with lots of concern throughout the day. It actually got a little comical at one point because he got yelled at to pay attention by Mrs. Price.

When we got out of school for the weekend me and Caleb hopped on the bus that would take us to the stop by his place. We had agreed earlier in the week to change things up and spend the night at his house to give Jordan a break from us. And also to play video games on his Xbox One via his room's 65" 4K HDTV. But mostly to give Jordan a break. Because you know, I'm a thoughtful brother.

We got off the bus and made the short walk down his cul-de-sac to his big two-story house. I know I mentioned earlier in this story his house and neighborhood were nice but let me just expand upon that a tad. The house was made of white brick with a charcoal grey concrete tile roof and matching shutters on the windows. Anyone could also see the house had two fireplaces courtesy of the chimneys: one in the rear of the house where the large open space family room (or is it living room? I can never remember which is which) and kitchen were, and the other on the side of the house where his parents' bedroom was. They also had a fireplace in their backyard with a TV built into it adjacent to their pool just behind the outdoor kitchen. Because they are that kinda wealthy.

So now that you know what house I want to die in looks like, let’s resume the story!

We walked into his house through the large dark stained wooden front door and proceeded to kick off our shoes.

"MOM! YOUR FAVORITE CHILD AND ME ARE HOME!" Caleb announced. Oh yeah, his mom totally loves me. Seriously thinks I'm the best thing that ever happened to her son.

"Jesse darlin'!"

I looked up in response to the very southern accent to see a woman of about 6 foot even with "Big Texas" style (Google it) blonde hair and rockin some dark red lipstick, along with giant gold hoop earrings, step into the main hallway from the archway under the grand staircase that goes into the kitchen.

"So glad to see you! How's your brother?"

"He's great ma'am! Been working more since he got promoted to assistant manager, but he does love the pay increase!" I replied just as she pulled me into a huge bear hug, damn near smothering me with her Dolly Parton sized boobs.

"Seriously am I just gonna get ignored here!?" Caleb whined/pouted, saving me from the ritual smothering I was receiving courtesy of his mom's bosom.

"Oh child please! You can get some luvin' when you decide to stop livin' with this sweet thang and show your mama some love!"

And now, right on cue, the cheek pinch. I'd learned to just take it...

"Ugh, mom, stop smothering Jesse and don't guilt trip me. You know I love you!" Caleb protested. Though the part about me was, as always, in vain.

"Mhm, you say that but every time I try and spend time with you, all you do is complain..."

"Jesus, mom, your idea of spending time is dragging me to see some dumbass musical! I hate those! We don't have to have things in common for me to love you! Now can you please tell me, us, whatever, what's for dinner and let us have our Friday!?" he huffed.

Yeah so, a bit of background here, Caleb's mom is definitely... extra. He even refers to here as Robbie Jo (her name being Robin Jo — I mean, so Southern, right?) Extra. She has an over-the-top personality and definitely has a tendency to blow things way out of proportion. Which I guess is why she's a good campaign manager? But I digress. She takes things with her son very personal and any (pretty much all) failed attempt(s) to bond with Caleb inevitably get turned into how he doesn't love her and want to spend time with her.

"Fine! If I'm such an embarrassment I'll just go back to prepping the chili I'm makin'. Jesse darlin' it's such a treat to see you in our home," she looked right at Caleb when she said that, "for a change. You two boys go on and have fun now. I'll call when supper is finished."

"My god mom you're so dramatic!" Caleb shouted after her as she went back into the kitchen to resume her dinner prep.

"Aw come on dude she's not that bad. Plus, how can you hate Southern hospitality personified?" I said with a small laugh.

"You don't live with her dude. You really don't get how extra she is sometimes."

"You barely live here yourself," I teased with a playful smirk.

"Oh you're such a riot. Now come on. I need to kick your ass in something," he said over his shoulder as he quickly made his way up the stairs to his room.

"Not even in your wet dreams!" I shouted back as I hurriedly followed him up the stairs.

"Jesse James Koenig, you better watch that mouth!"

"Sorry ma'am!" I shouted back sheepishly to Mrs. Hollingsworth (Oh side note, Caleb's last name is Hollingsworth. Not like it was super important so far, but yeah, now you know!).

I heard Caleb start laughing as he headed down the upstairs hallway to his room as I reached the top of the stairs and followed him. As we entered his room I looked around. Nothing had really changed about it since id known him. On his walls were the same posters of bands he liked and video games he played. The sheets on his dark cherry wood bed always unmade and in tangled mess. Random articles of clothing that may or may not be clean on the floor and his acoustic guitar sitting on its stand next to a computer desk covered in empty soda cans and pieces of paper he allegedly used for homework. In short, it was a teenager's room.

"Hey Cortana, turn on."

At that command I heard the familiar beep of his Xbox One coming to life, followed by his TV a second later. Due to the way he had it set up, rather than go to his home screen it automatically went to whatever the last channel he watched on cable was. It must have been HBO because we got treated to a scene in Jurassic World where the Chris Pratt's character was walking through the jungle with Bryce Dallas Howard’s character.

"Love this movie!" I said excitedly.

"Oh believe me I know," Caleb teased. "I can't even begin to count the amount of times you've made me watch these movies with you."

"Don't you even dare pretend you don't also enjoy dinosaurs!" I contended while giving him a mean point with my pointer finger.

Caleb laughed and cracked his trademark goofy grin. "I do enjoy those movies, but nowhere near as much as you! Honestly, I think you have an unhealthy love for T. Rexes!"

Ok, he had me there. When I was a kid, I was actually convinced that The Lost World: Jurassic Park was the single greatest film ever made because of the infallible logic that it had to be since it had not one, but TWO, full grown adult Tyrannosauruses. Don't judge me.

"Psssh! You wish you were as awesome as a T. Rex!"

To that epic comeback, Caleb smiled and playfully rolled his eyes while he grabbed the controller and switched the screen to Halo 5.

"Ok, Brobi-Wan Kenobi: let's game!"

I grabbed my controller and we both plopped down into his pair of stupid big bean bag chairs and began the first of several competitive matches over the course of the next two and a half-ish hours on Xbox Live. We were doing fairly decent overall, though having better online teammates sure as shit woulda helped.

"OH BOYS!" we heard Mrs. Hollingsworth bellow. "GET YOUR HUNGRY TEEN BEHINDS DOWN HERE!"

"COMING, MOM!" Caleb hollered back. "Well these noobs online suck ass and I'm starving. By the way, I want you to appreciate how much begging I had to do to get my mom to use real meat tonight. If I hadn't it would be some kinda wannabe turkey chili, I'm sure. I mean, it's definitely still wannabe chili compared to Jordan's chili, but at least she's using beef!"

"Yeah, I love your mom, but it still amazes me that for how Southern she is, she's so into healthy cooking! Like, Paula Dean would be so disappointed!" I joked.

"I know, dude — I hate it," Caleb groaned. "It's like, a total contradiction! And you know how much my dad works so his opinion is useless to me! At least I had you to use for an argument this time."

I guess that's as good of a cue as any to tell you a bit about Caleb's dad. He looks like a late 40's version of Caleb (which is a very good thing, FYI) but he's way more muscular and keeps his head shaved. Unlike Caleb's lazy ass, he works out. And despite what Caleb just insinuated, he actually appreciates Mrs. Hollingsworth's healthy cooking. I've only actually met him a few times, seeing as saving lives is rather time-consuming, apparently, but he's always been very nice to me.

We headed downstairs into the kitchen where we found two bowls of chili and some cornbread waiting for us on the counter. We quickly grabbed a couple of Cokes (one of the few unhealthy things Caleb's parents will allow him, oddly) out of the fridge and immediately began to dig in.

"Glad to see you boys are hungry! I don't know if Caleb told you dear, but he complained up a storm this mornin' about me using `real meat' in whatever I made for dinner."

"Mom. Turkey doesn't belong in chili. It just doesn't! And it also doesn't belong in stroganoff! And neither do peas! Can you just please hire Jordan to cook for us?" Caleb asked completely serious.

Ah Christ...

"Well I'm sorry if I care about my baby's health!" she huffed.

Dammit Caleb...

"Mom food is meant to be good for the soul!"

Oh fuck me, he's quoting Jordan in the entirely wrong context.

"Caleb Ashley Hollingsworth!"

Full name. He's awakened Robbie Jo Extra now.

"You better watch it before I take a wooden spoon to your behind! How Jordan cooks in his house is his business. But so help me Lord as long as you're my child and I'm feedin' you; you will enjoy whatever I put in front of you!"

Caleb was about to make another smart ass reply before I quickly squeezed his knee, causing him to jerk slightly while I jumped in to try and diffuse the brewing nuclear situation, "Wow Mrs. Hollingsworth! This chili is really delicious! Honestly, even if you had used turkey I would have loved it!"

Mrs. Hollingsworth was briefly caught off guard by my interjection, but the compliment was enough to visibly calm her down and turn her focus on me.

"Why thank you Jesse! You are just too sweet sometimes! I'm glad someone here appreciates me!" she immediately stared at Caleb as she finished responding to me.

"Jesus, Mom..." I squeezed his knee again as a warning, causing him to give me an annoyed look before letting the argument go. "Ugh, forget it! The chili is great, ok?" he finished as he angrily looked away and shoved the rest of his cornbread in his mouth.

"Thank you sweetie. Now your daddy won't be home until late tonight like usual. I'm gonna go soak in the tub and relax before I watch some TV. Jesse darlin', you have fun..."

Something about that clearly bothered Caleb because before either of us could say anything, he got up and stormed off to his room.

"Well I guess I better go see what he's mad about now..." I said to no one in particular as I took one last bite of the chili.

His mom shook her head and sighed, grabbing a bottle of chardonnay off the counter. "I don't even know why I try sometimes. Good luck with that boy. The good Lord has blessed you with more patience than me when it comes to him."

"Trust me it's not as easy as I make it look!" I said with a small chuckle. "Have a good rest of your night, ma'am!"

Mrs. Hollingsworth gave her own small laugh as she smiled at me before heading off to her bedroom and me upstairs to Caleb's room.

When I got to his room I looked in and saw him with his back facing me, playing on his gaming computer he had gotten last Christmas.

Ugh, this is gonna be fun.

"Can I come in?" I asked tentatively, figuring it was best to test the waters first.

"Yeah." One-word answers are always a good sign. Said no one ever.

"Hey, I was just trying to diffuse the situation before you guys went at it and you got grounded. I'm sorry if I upset you, dude..."

"You didn't, Jesse," he sighed as he turned around to face me, his face looking weary. "I'm sorry Jess, but I'm just so frustrated with her shit. All she ever does is bitch that I don't love her and appreciate her enough and then when you come over it always how amazing and appreciative you are and shit. And then she wishes you have a fun night and doesn't even mention me at all!" he vented, clearly getting worked up as he did.

"Well she just might have if you hadn't stormed off when you did."

"Are you seriously taking her side?" Caleb asked angrily.

Dammit Jesse...

"No dude... ugh, look, you know how your mom is just... I don’t know. Maybe just, throw her a friggin' bone every once in awhile."

I made a small smile, hoping he caught my Austin Powers reference, but he continued to frown. So he either missed it or didn't find it amusing.

"Fuck you dude. God forbid you'd side with your best fucking friend!"

Uh-uh, no. Not happening again this soon.

"Caleb I'm not fucking doing this. It's stupid as shit. I wanna have a badass time with you, but if you're gonna act like this, I'm just gonna go home!"

Well, my threat worked (for once) because Caleb's eyes immediately got bigger.

"No, no, you're right, Jess. I'm sorry, ok? It's just…​ Ugh! She just presses all my buttons sometimes... Christ, she is always pressing my buttons! And..." he paused to look at me, "No, forget it. I said your right, I’m not going to keep bitching about her. Let's just change the subject ok?" he apologized, looking at me pleadingly.

"Let's just play some video games, ok?" I sighed, relieved that my Friday night wasn’t going to be ruined.

"Yeah sounds good dude. What ya feeling?" he asked, clearly also relieved I wasn't gonna actually go home.

"Let's play some story mode on Halo. I don't wanna deal with worthless teammates online," I suggested.

"Ok, sounds good!"

Caleb changed the game mode to story and selected the single player since for some dumbass reason the developers had removed the split screen option. Because of this, we would always put the game on Legendary mode and make a mini game out of it by seeing who could survive without dying the longest and then switching to the other person so we could both play. We had beaten story mode several times already, but it was still fun to play regardless.

This went on for a few hours and, as usual, involved plenty of shit-giving and attempts to distract the other so the person playing would die faster. One of the many nice things about Caleb's room was it was on the other side of the house from his parents' room. So as long as we kept the door shut, we could get pretty rowdy without the noise bothering them.

After another failed attempt to take down an Eternal Warden, thanks in part to my excessive poking, Caleb put the controller down and looked at me with a kind of crazy smile. You know the one where the person has had a crazy thought?

I looked back at him bemused. "What, you dork?"

"Wanna do something different?"

"Ummmm sure? Like, what did you have in mind?"

"Well... We both are at that age where we start watching `other' kinda `tubes. You know, like any normal teenager does when he... ya know..."

What the hell is he blabbering about?

"So, I was wonderin'... would you maybe wanna... I don't know... watch something on the `tubes?" he asked shyly, never looking at me for more than a few seconds.

"Caleb. What in the ever-loving-fuck are you talking about!?"

"Ugh you're so fucking dense sometimes... porn. Adult videos. Spank material... ya know..." he replied while making a jerking motion with his hand.

I was completely taken aback by this. I mean, if we are being honest, who really expects their best friend to ask them that?

The shock must have been pretty clear on my face too, because Caleb quickly began stammering, "W-we don't have to, I mean! I just, I guess, thought it might be kinda cool or something... you know... to see what we are both into or whatever. Lots of guys do it..."

"I'm game."

Honestly, I don't know who was more shocked at my sudden agreement, me or Caleb.

"Oh... oh? oh! Cool then! Um... come on over to the computer then and grab the extra chair," he instructed me. And though I couldn’t be sure, I thought I detected a hint of excitement in his voice.

I got the chair and moved it over by his computer as he was busy pulling up some random porn website I'm assuming he knew well. I honestly felt like I was on autopilot, still kinda shocked with myself and wondering what I had gotten myself into and why Caleb wanted to do this.

I quietly sat down next to him and looked at the website. Pornhub. I mean if it ain’t broke...

"Sooooo... anything in particular you wanna watch?" Caleb asked without really looking at me. At least I wasn't the only one feeling awkward about this.

Me and you doing 69?

"I guess whatever you want is cool." See? Exactly what I was thinking.

"Ok... How about some ones where they aren't very experienced?" Yep, exactly the same thing.

He quickly typed "amateur" and "teen" into the search bar and hit enter. Quickly a massive number of videos appeared involving what Caleb had searched for. He quickly filtered the videos to only show ones that where at least 10 minutes long.

"Here let's watch this one."

He clicked on a random video and it immediately started showing a scene of some honestly boyish looking girl with a small chest and short cut hair dyed baby blue sucking the dick of some college aged jock.

We sat there in silence just watching the video. Well, us watching the girl working the dudes pretty big looking cock with her hand and mouth and me wondering what it might be like to be her right now.

Yeah if this is just a phase it’s really... oh fuck it, it gets me hard.

My dick was straining against the inside of my shorts. Like bad.

Hell, a cool breeze has gotten you stiff before. And this is porn. I mean, yeah. Dick gonna harden... And if I'm hard, then... Why hello there, Caleb's erection! Dunno what game we're playing now, but we've officially entered Hard Mode and I am not prepped for this!

Out of the corner of my eye I could see Caleb was as hard as a rock through his basketball shorts (Man I love that he wears those. Which is now my least gay thought of the day somehow.). He was also making no attempt to hide it. I glanced at his face; he was focusing on the screen, but he must have known his erection was obvious because his face was flushed. Or maybe it was the hormones.

My mouth was suddenly very dry. So I'll remind you about a disappointing thing about gym (among so, so many), no one ever takes showers in my period since it's the last one of the day. They all do it at home. So I haven't seen Caleb naked. And now, in this moment, all I could think about was what he looked like naked. Fuck the video. I wanted to watch this Adonis right next to me and I don't care how gay that makes me right now.

"Does yours look like his?"

"Mmm... huh? Wait what?" I asked, snapping back to reality and fully facing Caleb.

"Does your dick look like his? Is it really straight or does it curve?" he asked curiously as he turned to face me, seeming oddly comfortable with the question.

"Uuuuuhhhhhhh...." I replied, completely at a loss for words.

"Have you not ever seen your dick before, Mr. Nudist?" he teased with a nervous laugh.

Yes, Caleb knows I enjoy hanging out naked when I'm alone. Jordan apparently gave him a warning one time when he came over looking for me. Even then, he would have walked in on me a few times if I hadn't started locking my door.

I made the mistake of glancing down at his hardon again.

"Oh... It’s umm... totally ga... straight! Wait, I mean curved!"

Oh dear god I'm an embarrassment to humanity right now.

Caleb, though, started laughing at my gift for the english language.

"Wow that was hard to listen to dude! Pun most definitely intended!" he said, laughing even harder at the end. Even I had to laugh at that.

"Hey now, that's not exactly a question I was prepping for!"

"It's not that difficult!" he replied, still chuckling. "Mine is mostly straight when I'm hard. See? Easy!"

"Whatever dude," I said with a playful eye roll.

"Wanna see?"

OH. MY. MOTHER. FUCKING. GOD.

Did I say I had a look of shock on my face before? I'm sorry for lying to you. Now I had a look of absolute shock on my face, complete with mouth slightly ajar for added touch.

"Sorry, that was weird to ask. I shouldn't have..." Caleb backtracked before I cut him off without thinking.

"Yeah."

Caleb looked at me with a bit of surprise and confusion.

"Yes, you want to? Or yes, it was weird?" he asked a little hesitantly.

I can't believe I'm about to fucking say this...

"You can show me. If you want. It's cool, I guess. Like I don't mind…​"

Jesse shut your damn mouth!

Caleb slowly stood up, still somewhat unsure if I really wanted him to go through with his offer. He got to where his rock-hard penis was about level with my eyes, causing me to make a slight gulp. Then slipped his thumbs into his waistband.

Dear god this is gonna happen. I don't care what happened in the bathroom this morning this is about to be the best day of my fucking life and I really don't give a fuck how gay this makes me right now.

"Hey."

My eyes immediately snapped up to his, my face flushed as hell.

"Ye..." Make fucking words you damn moron! "Wassup?"

Just... facepalm.

Caleb chuckled slightly. "Could you go lock the door please? Just in case?"

I merely nodded and went total autopilot as I got up and walked over to his door and locked it before returning to my chair.

Caleb then looked at me and took and deep breath before he slowly started pushing his shorts and boxers down.

Oh god this is really happening! Breathe Jesse! For God's sake, breathe man!

Slowly, his neatly trimmed pubes came into view, showing me that the carpet matched the drapes (hm, never using that term again). Then came the golden moment, his dick was about to be revealed! The base came into view and I nearly creamed my pants.

Oh my fucking shit! Here it comes! My darkest fantasy is happening!

Then at that exact moment, God decided to shit on me. We heard the garage door closing as the door between it and the laundry room opened and closed loudly, causing both of us to jolt in surprise and for Caleb to rip his hands away from his shorts just before I could see his most private part. He then quickly pulled his shorts back up to their original resting place.

"Shit that startled me! Dad’s home I guess." Caleb said with a nervous laugh as his cock clearly began to deflate, my cock also rapidly softening as well.

"No shit Sherlock! Just in time to ruin the moment before I got my twisted wish fulfilled!" is what I wanted to say.

"Yeah..." is what I actually said.

"Ummm... so yeah I'm gonna go say hi to him... wanna join?"

"No, I want you to finish pulling your fucking pants down you goddamn tease!" is what I wanted to say.

"Ok, sounds good," is what I actually said.

Caleb awkwardly turned and headed to his bedroom door while I (on the inside at least) dejectedly got up and followed him out of his room after he unlocked his door and downstairs where we found his dad fishing leftover chili out of the fridge.

"Hey, Dad!" Caleb greeted him as we walked into the kitchen.

A little too damn cheerful after what just got ruined! Ok, get a hold of yourself, Jesse...

"Ah, Caleb! That must mean your partner in crime is here too! Jesse my boy, how are you?" he replied in his still strong Pittsburgh accent as he turned towards us holding a container full of chili as well as cheese and sour cream.

"Was about to see your son naked if you hadn't come home!" is what I wanted to say.

"I'm doing great, Dr. H." is what I actually said.

Ok, now I'm going to do that whole getting ahold of myself thing.

"How was work today?" Caleb asked.

"Went well. Had to perform a six-hour emergency bypass surgery today. Almost lost the patient! But your old man got the job done," he said proudly.

"Awesome, Dad, way to go!"

"Yeah Dr. H, that's great!" Ok, who can stay salty at a badass like that?

"How was school today boys?" Dr. H asked as he began heating up the bowl he made, adding, "And Jesse, I told you I hear doctor all day! You can just call me Chris!"

"Sorry Dr... I mean Chris. Just a habit with adults I guess. And I had an ordinary day," I replied, glancing over at Caleb.

Caleb gave me a look back, obviously still not ok with the vow of silence I made him take, before also saying he had an uneventful day.

"Well, boys, sometimes those days are the best. Take it from me. Now go enjoy your night. I'm just going to eat this before hitting the shower and then off to bed. I'm beat!"

"Ok Dad. Awesome job today saving that person's life. Love you!"

"Yeah Chris, sleep well! You deserve it!" I chipped in.

Caleb gave his dad a quick hug while I followed with a fist bump before we went back upstairs to his room.

"Soooooo...." I began as we walked in and shut the door. "About earlier..."

"Um yeah... about earlier... I was horny from the video and I guess my hormones started raging. Sorry, I know that was weird." Caleb replied, a little embarrassed.

Dammit no! He regrets it! There went my one chance to satisfy my weird urges and move on...

"No no, it's cool... I get it. Same thing happened to me!"

Welp, there's the second lie I've told Caleb in the last 24 hours. Or was it? Maybe it was just the hormones...

For a second there, I swear saw a weird look go across Caleb's face that I couldn't identify. But before I could dwell on it he replied, "Well, thanks for being cool and understanding. I know I've told you this before dude, but you really are the best friend I'll ever have." He then smiled at me, causing the remaining awkwardness to dissipate.

You know what? It is a great day, night, 24 hours, whatever. No matter how it started, I'm with my best friend Caleb. And I don't need to see his dick to make that amazing.

"You too, man. Boy pretty eyes and all."

We both shared a laugh at that before we decided to play another couple of rounds of Halo, finally hitting the sack sometime in the wee morning hours.

So we got to go over to Caleb's house for once! That's fun! Hope everyone enjoyed meeting his parents, well his mom mostly, haha. And sorry for being such a tease but come on, we can’t have too much fun this early =P. Thanks for reading as always!

Please email me anytime at JesseJamesNiftyEmail@Gmail.com and I'd be more than thrilled to respond to any and all comments, questions and yes, constructive criticism!

 — Jesse