It's a Journey Not a Destination Ch. 02

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Isabel's journey truly begins... is this school for real?
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Part 2 of the 11 part series

Updated 06/16/2023
Created 12/03/2022
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Chris_Tee
Chris_Tee
166 Followers

Hey reader... welcome back! If you're starting here, there was a chapter 1. It's kind of relevant but if you want to start here... I don't judge.

For those who are coming back, thank you! As I've indicated in the past, I really have no expectations for my stories as they are proving to be some good head gym for me, but I can't lie... it was pretty cool to have a few people decide to follow me!

Our girl, Isabel has made a huge decision to continue her education in a totally unknown environment. Her journey only gets better from here.

As always, friendly feedback and critiques are welcome... I hope you enjoy

IT'S A JOURNEY NOT A DESTINATION CH.2

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SLAM! Even sitting at my desk, up in my bedroom, I could hear the front door. Followed by the sound of someone taking the stairs two at a time. For a girl who is so petite, she can really make a ruckus when she's on a mission. Wait for it... wait for it... BAM! Good thing my bedroom door wasn't completely shut. She probably would've gone through it.

"Izzy! Please, tell me you're not really serious about going away!" Katie Montgomery has been my best friend since grade school, and I knew she wasn't going to take this well. In fact, even after I asked my dad to enroll me in the private College, I struggled with how I was going to explain this to my Katie-bear.

"Discreet as usual Tinker Bell." This was my nickname for her when she got angry or flustered. Physically she was the embodiment of the famous fairy Tinker Bell. Short in stature, short messy blond hair, and stacked. She had the most perfectly proportionate body, shrunk down to a 5'2" frame. When she got riled up, she fluttered around like she was a pixie, so the nickname has stuck all these years.

"Don't Tinker Bell me Izzy! This really sucks! I thought you decided to stay here. What's going on? Does this have something to do with that Gavin guy?" Tinker... err, I mean Katie, was super intuitive. She could read a room like no one else, but more to the point she could read me like she was part of my thoughts. If it were anyone else, I'd be freaked out, but she was my Katie-bear.

"Can you just chill a minute? This whole thing has been a shit storm and I can't have a rational conversation with you going all Tinker Bell on me!" Her composure quickly dialed back, and she walked over to me, sat on my lap, and gave me her classic death grip hug.

"I'm sorry Izzy. Sometimes I forget there's more going on in this world than what affects me." She pulled back, smiled, and kissed the tip of my nose. "Talk to me goose." Katie loved her movie quotes, and this Top Gun reference was a staple in her repertoire.

"You're right. Gavin was sort of the final nail in the coffin of my decision. Once again me and my... thing (gesturing down to my crotch) fucked things up."

"You actually told him?" I could see the alarm in her face.

"Worse actually. I showed him." Katie jumped off my lap and brought both of her hands to her face and gasped.

"You didn't! Jesus Izzy! What were you thinking? What did he do? Did he freak out? Was he mean? Was he..." I had to interrupt, or her list of questions would've taken up the afternoon.

"Whoa, whoa girl! Can I talk for a second?" Katie plunked her butt down on the edge of my bed and her hands slowly fell to her lap. I stood up and took a deep breath. "Remember when I told you he shared something personal with me? Well... "

So, for the next 15 minutes I walked her through the events of that night with Gavin. I expected her to jump in with a bunch of questions, but I think she could tell how traumatizing the whole thing was. When I finished, I sat down beside her and shrugged my shoulders. "That's it. That's how the whole private school thing came up again. I mean it's not solely based on him, but it was kind of the kicker. Fitting in is a lot harder than it was in high school Katie. I don't know. Do you think I'm copping out?"

"Did he really try to take you in the butt?" Her look was incredulous. Typical Katie. She probably stopped listening after that part of my story.

"Yes Katie. He tried. I really wish he hadn't but like I said, we had a good talk and I think we're in a good place again."

"Man! I give him a lot of credit for even trying! He must've really liked you Izzy. Crazy stuff!" I had to look at her closely to see if she caught the irony in her own words.

"Yeah, it seems I know someone else like that," I smiled. Right away she caught on and tackled me to the bed.

"That's different! Besides, I'm your bestie! That comes with certain privileges."

"Like breaking a wrist falling off the end of my bed?" I snorted.

"You scared the shit out of me! If anything, it was your fault! You didn't prepare me enough. You should've told me to back up." She whined.

"I did. You just weren't listening." I laughed. Katie stopped her squirming and stared into my eyes and gave me another kiss on the tip of my nose.

"Oh, but we've come along way haven't we Izzy?" The kiss was a subtle distraction as her tiny hand moved to my crotch.

"I'm beginning to think the real source for this friendship is in your hand." I smirked. Truth, was I knew Katie was my forever friend and while our relationship was a little unusual, besides my parents, there was no one I trusted more.

"Oh, stop your whining Izzy. You love the attention as much as me. Now can we have some play time or are we still in serious mode?"

We were 13 when I told Katie about my special condition and was absolutely terrified she would no longer want to be my friend, but Katie was barely even fazed, and we never even spoke of it. That was until we got into high school, with boys, hormones and all that good stuff. My "problem" wasn't as big a deal back then, as I was going through a rather unusual puberty, but I was terrified of the school showers and even the washrooms in fear my secret would get out. Katie was always there. She was my partner in crime, my lookout, my backup.

It was a Saturday night sleep over that catapulted a change in our friendship. It was a typical night of movies, pizza, gossip, and a few stolen shots of whiskey from my dad's bar. A friendly disagreement of who was hotter... Chris Hemsworth or Ryan Reynolds (spoiler, it's Ryan. Come on! The strap on scene in Deadpool? HOT!), turned into an amateur wrestling match and things got exciting, and by things, I mean my thing. It became the elephant in the room and Katie's curiosity got the best of her and she touched it. We both froze, and then out of no where, she asked if she could see it. Caught up in the moment I suggested we go to my room. There we were kneeling face to face on my bed when she reached for the waist band of my pajama bottoms. I pushed her hands away and continued the progress for her. She bent forward in anticipation, and I warned her it was going to pop out and... well you know how that played out. In the weeks after, we were scooting up to my room regularly and Katie was finding more and more ways to torture me (in a good way).

"I think we can be serious after." I moaned and instantly Katie sat up, so she was straddling my hips and began to remove her top and bra. I gently ran my hand down her curves, fuck she was built!

"Is the lube still in your nightstand?"

"Uh huh." Not the most articulate response but all my main thinking had dropped to my other head. Katie wiggled up my body so she could reach my nightstand, all the while her Lulu covered muff was gently rubbing my chin. "You could've at least lost the pants if you were going to do this." I joked.

"Got it! What did you say about my little muff?" She grinned,

"Actually, I didn't say anything. I implied."

"Well once I get these pants off, I'm going to imply it all over your face!"

True to her word, she stood up and made fast work of her pants. She then ran to the end of the bed and grabbed at the ankle of my pants and helped me shimmy out of mine. A gleam came to her eye as she heard my cock snap back and make a huge slapping noise on my stomach. Like a tiger she stalked around the side of the bed, climbed on, and straddled herself above my head. She slowly lowered her pussy to my face as she began to slather my cock with the lubrication. I immediately brought my arms up and grabbed her ass with a reverse grip. While gently parting her cheeks, I pulled her to my mouth. She smelled so good and always tasted better, I thought, as I began reacquainting myself with the taste of her.

"Fuck! You know just what I need Izzy! So, fucking good! Eat that pussy!" My sweet little Katie could swear and talk dirty with the best of them when she was horny. Sometimes, I think she could make a sailor blush! In no time her juices were covering my face as I nibbled her smooth lips and lathered her clit with a million tongue lashes, her groans were music to my ears. To add to my euphoria, she was now doing the double hand pump along my cock, knowing just when to squeeze and twist. Nobody knew my cock better than her. Hell, I think she knows it better than I do! For sure her hands are on it a lot more than mine!

"Holy fuck Izzy! I'm gonna cum already!" Wow that was fast I thought! "Too good... your tongue... your big fuckin dick! Shit! I can't... Ohhhhhhhh Fuck! I can't hold it off! Ohhhhhhhh Fuck! Yesssss!"

Boa constrictor. That's what she reminded me of when she orgasms. Her hands stopped moving but gripped my cock like she might fall. Her legs squeezed my head as she simultaneously ground her pussy onto my mouth. With every convulsion her grips got tighter and tighter. I'm literally drinking her fluid now as it shoots into my clamped-on mouth. Not a sound is coming from her. I can visualize her contorted, silent screaming face and it makes my cock swell even more. Finally, after her immense orgasm subsided, she let go of my cock and just laid flat on top of me. Her legs relaxed and spread causing her ass and pussy to just plop over my whole face. At first it was delightful, wet, warm, and tasty, but soon my need to take an actual breath was becoming a factor. First, I tried to lift her, but she was dead weight, so I started tapping her bottom. Nothing. So, I pinched. She immediately understood and lifted herself off my face.

"Shit! Sorry Izzy. I got lost for a moment."

"If I ever get the chance to choose how to die, I know just who to call." I huffed as I got my wind back.

"It would be my pleasure madame!" She chuckled using a fake aristocrat voice. "Seriously Izzy, none of my other orgasms even come close to the ones I have with you."

"Not even the romp you had with that black exchange student? What was his name? Carmichael?" I had to ask because she would go on and on about that night.

"Right! Geez, that's a tough one." As she brought a finger to her twisted lips, "Nope! I'd still have to go with you! Besides he had a real anal fetish." She giggled.

"Right. HE was the only one. I seemed to recall someone gushing how good it felt having his big black cock pounding your tiny little ass!"

"Hey!" She tried to feign a hurt look, but it only lasted a few seconds, and she started laughing. "Ok. It was fuckin awesome! The dude could fuck that's for sure! Too bad he turned out to be another douche bag." With that Katie resumed her straddling of me as she wiggled down till she was at the top of my pelvis. She restored her grip on my still hard cock and began stroking me again, but this time I could feel her wet pussy pressed against the base. "I still can't believe Gavin even tried to squeeze this in his butt." She marvelled, "Although I'd be lying if I didn't admit the thought has crossed my mind more than a few times." As she sneaked a peak back over her shoulder and winked at me.

Long ago, when we first started fooling around with each other we both agreed, albeit with some remorse, that any and all intercourse was off the table. Some of it was the concern of me hurting her tight little body, but mostly we agreed that it could really put our relationship in jeopardy and neither of us wanted to take that risk. So, we found other things to do. This is how I found out I really like the taste of pussy, especially Katie-bear's. Katie was a self professed addict to my cum. I know she's blown a many a guy, but she swears mine is in a league of its own. The big league she calls it. Quality and quantity were her parameters.

"God, it seems like forever ago that I got a tummy full!" Katie was working the shaft of my cock like cat on a scratching pole, but in a good way. Up and down, up and down, the friction was increasing with her grip. She was grinding her clit into the base and was undulating her hips timing everything just right. How long has it been since I popped a load? Two, maybe three weeks? Shit, this is going to get messy!

"You're getting close, aren't you? I can tell. The heartbeat in your cock gets heavier and quicker." She changed her tactic and began varying her grip and tempo. It felt glorious and I was just getting to the edge of an epic release when she stopped.

"What the fuck! Katie! I'm almost there, why did you stop?" All my clenched muscles started to relax as my labored breathing was playing catch up. Just as I was about to repeat my displeasure, I felt her kiss the top of my crown.

"Electric slide!" She squealed. Katie removed herself from my hips, turned around and once again straddled me, but this time my cock was flat, trapped between my stomach and her slick pussy. It was the name she invented for this little trick. I'm guessing it's a play on words from a popular dance in the 70's and truth was, it was rather fitting. "You know the rules, no touching!" As she proceeded to add even more lube, "There we go, all nice and slippery! Are you in a rush to finish the serious part of todays meeting? Hmmm?" Her look was one part inquisitive and two parts dirty. The question was relevant though. One time we played this it lasted for almost 2 hours!

"Can we find a balance?" I moaned, "We do have a lot to talk about and my parents are expecting us downstairs for supper at some point."

"Fair enough!" On that note Katie leaned forward and grabbed my breasts as she started a nice slow slide and wiggle. Drawing her hips up my body till her pussy touched the head of my cock and then she leans down and does a slow push, sliding back down to my balls.

"OH FUCK! I moaned. Did I forget to mention I love this game?" Katie stared straight into my eyes and began her rhythm of sliding her pussy along the length of my cock from tip to balls. She possessed some major abs from her belly dancing classes and she was showing off her skill right now. Sometimes she'd stop at my tip where it nestled between her lips and just quickly rock back and forth. When my eyes starting crossing, she'd slowly go back down to my balls. "You're such a fucking tease! You know I'm dying right? Like, just throw some dirt on me already!"

"You know Izzy, just because you got this great big cock and these huge motherfucking balls, doesn't mean you're always in charge you know. I own you!" She snickered at my look of annoyance and worked her way up again. "You're going to like this." She spoke. I watched her with curiosity as she slid up to my engorged head, did her torture(esk) rocking motions, then she slide further until her ass passed over too. Slowly, she pushed back and when I involuntarily flexed my cock, she pushed the head of my cock to the entrance of her tight little butthole. She stayed there for a bit, doing little circles, clenching, and unclenching her tight little puckered star. Then she increased her pressure like she wanted me to enter her ass. I didn't want to protest, but I also didn't want to break our agreement. Thankfully Katie changed her angle ever so slightly and the head, followed by my painfully hard shaft, wedged its way up between her tight, perfect cheeks. She backed up till she had my cock straight up and could no longer drive it downwards. Katie sat up and reached behind herself and grabbed my cock. Her hand worked up to the head and once she found the top, she kept her hand at that level and slowly glided it to the front of her body. It stopped just below her sternum. "Is it crazy that even though I know you'd have to rearrange my organs, I still can't stop wondering what it would be like if you fucked my ass?"

"No fair!" I moaned as that was her trump card. Despite our agreement to never "do the deed", she wasn't shy about verbalizing the act as she knew it really got my motor running. She slowly began to release my cock from it's pinned prison and it followed her right back till it was once again flat on my stomach. Katie proceeded to repeat this move over and over while verbally taunting me with stories of me wrecking her ass. "Katie... I.... shit it hurts! I gotta cum soon! My balls feel like they're in a steel trap! Please!" More giggles came from her sweet mouth, but she finally stopped her pleasurable torture and switched so she was now facing my cock.

"Ok, ok. I guess we can take care of that for you, my poor baby." The sarcasm was a little thick, but she was still pushing all my buttons. Katie began to massage my balls with both hands. They were very taut and full of cum, and she knew it. While continuing to massage my balls with her left hand, her other moved up my shaft to my now purple crown. I knew what was coming but the anticipation was killing me! Her left hand left my balls and squeezed the base of my cock, pushing it away from her body stretching my foreskin to the max, while her right hand started to corkscrew the top third of my cock. The sensation was electric, and I could feel my orgasm moving ever so slowing from my toes, up the inside of my legs till it reached its exit source.

"Oh fuck! Oh fuck... Ohhhhhhh Fuuuuck!" The first spasm of my cock was choked off by her left hand, which she released just before the second spasm, sending my cum shooting straight up into the air. The next shot went even higher and all I saw were "stars". The third and fourth waves were slightly less intense and that's when I felt those warm lips wrap around the head of my cock as Katie continued milking me and started moaning as she drank my cum. She had lifted herself up so she could get more of her mouth around my cock head which left her butt exposed. Out of sheer instinct, I pushed my thumb in her slippery ass and 3 fingers into her sopping pussy and frigged her to a climax of her own. We moaned and groaned for god knows how long. When I opened my eyes, Katie was looking back at me over her shoulder.

"Now THAT was a good one!" She declared. Katie pulled forward till my hand plopped out of her play holes. She moved beside my hips and bent back down to lick my still erect cock. Now that I could see her, the results of my orgasm were clear to see on her face, shoulders, and hair. "You almost hit the ceiling again Izzy, with those first two bursts... wow! I had to wait before I could safely get my mouth over you. Although you still painted my face pretty good." The first time Katie tried to swallow my cum, I caused her to throw up because, as she put it, it fires like a canon!

I rolled my head to the side taking a peek at the time and looked back at my cum soaked friend. "We better shower up quick. It's dinner time."

"For you maybe. I'm stuffed!"

"Ok. You can explain that to my mom." I laughed. On that note Katie gave my cock a quick slap and jumped from my bed to the shower in my ensuite. With one last moan I watched her perky ass wiggle its way across my room.

By the time I got to the bathroom Katie was already wet and shampooing her hair. "Room for one more?" I peaked my head around the curtain.

"Of course! Can you wash my back?" Does a bear shit in the woods? I thought. I shucked off my sports bra and stepped in behind my best friend. Grabbing the soap, I lathered up my hands and began to clean my cum off her shoulders and slowly worked my way around to her firm boobs. Katie murmured with appreciation, but we had to be somewhere else. I continued my exploration and slide down the sides of her curves and spent a lot of time soaping and cleaning her bottom. Well, after all, she was covered in lube. Katie had finished rinsing herself and spun around with a bewildered look, "Are you quite finished feeling me up Ms. Soapy hands?" I held my hands up like I was being held at gun point.

Chris_Tee
Chris_Tee
166 Followers