My So Called Life - Cover

My So Called Life

Copyright© 2025 by JRT

Chapter 1

Coming of Age Sex Story: Chapter 1 - A (mostly accurate) account of the life one Jason R Taylor, his loves and losses, his failures and triumphs. Born in the afterglow of the Summer of Love to kids who never grow out of their 'hippie stage', Jason sees every woman as beautiful, and he's not shy about showing her. Posting weekly to get feedback, this is my first published work. Please note, there will be no sex with minors below the age of consent.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   mt/Fa   Fa/Fa   ft/ft   Fa/ft   Consensual   Drunk/Drugged   BiSexual   Heterosexual   School   Vignettes   Light Bond   White Male   White Female   Oriental Female   Hispanic Female   Indian Female   Anal Sex   Cream Pie   First   Lactation   Masturbation   Oral Sex   Petting   Pregnancy   Sex Toys   Big Breasts   Small Breasts  

Jake and I had been friends since we met at seven years old at our private school. A few years later, Jake, his mom, and his older sister were in a bad car wreck when we were in fourth grade. He was mostly just badly beaten up, bruised, and I guess he had a concussion. I don’t mean to make light of all that, but his mom actually died, and his older sister still has a limp from a badly broken hip and leg. She used to be really into sports, like his whole family, so I guess she’s got depression now or something. I once heard my parents talking about some insurance settlement and how ‘the Steeles would be set for life if they could start living again’.

Anyway, Jake missed most of our fourth grade year, and he ended up having to repeat. I guess it was partly because of his recovery, but I think it was mostly due to how much the wreck hurt his whole family.

We hadn’t been in the same class since, but we were still on the same teams when he came back to school. Finally, just last year, Jake decided he didn’t want to be a year behind anymore. This time I wasn’t so much competing with him as tutoring.

School has always come easy to me; math just makes sense, history is interesting, English is my mom’s “bailiwick” (her word) so I had a cheat there, science is fascinating, literature is an enjoyable pastime (thanks again, to my mom), and so on. It doesn’t hurt that my parents, for all of their many parenting faults, taught me from an early age to prioritize my education. Or else. So, I’m an A student, though I’m in fourth place in class ranking behind a few ultra-studious kids.

Jake and I spent many hours last year in review and test-prep, one subject at a time. In an odd twist of timing, he took his sixth grade exams three weeks before his fifth grade tests! He didn’t break any records, but he had four “B’s” and two “A’s”, easily enough to allow him to graduate and move back into his year group with me - pending his passing the fifth grade tests. So, he buckled down to study for the fifth grade exams, by himself. The competition was back on, and he was determined to beat my fifth grade exam scores!

Unlike Jake, I hadn’t been lumped into the ‘jock’ category, but he was no dummy. With all of the studying we put into his sixth grade studies and his own hard work, he actually did beat my social studies and history exam scores.

I lay all that info out there because Jake and I are incredibly competitive on everything that we can compete on. Most slices of pizza? Jake ate a whole medium pizza and a half of another, (he only beat me by a single slice) and neither of us got sick (because that would have been a forfeit!). Worst sports injury? I once had my scalp cut open during an after school soccer game. That ‘break-away goal’ concept hadn’t quite worked in my favor.

Or, my favorite, how many times could we poke Mrs. Jacobs tight-skirted little butt before we got detention? She’s the hot, young, girls athletics coach and civics teacher, I won, four pokes! And two weeks of detention ... after the parent-teacher conference. Mom glared at dad for a comment he said under his breath about how I had good taste and was pretty much it.

And so it went, anytime we could compete, we did. Longest time holding our breath? Most slices of bread in our mouth at one time? Most times tossing a raw egg in the air - over his sister’s ridiculously huge tennis trophy - without breaking it, the egg or the trophy? ... and on and on the list goes.

He completely recovered from that injury mostly because his dad was a slave driver. Ok, to be fair, he was the boys Senior High Track and Field coach, so he really knew how to train and motivate. But I’d like to think his recovery was partly because I refused to stop challenging him. I ended up gaining a prior-Olympic track and field star as a coach as an unexpected benefit in Coach Steele - Jake’s father. It also explains why Coach would continue to push me just as hard as his son even after he had recovered.

So, we competed on everything. One last example: who had gone farthest with a girl? Well, I had thought I was ahead of my friend on this score. Turns out, notsomuch.


October 19th, 1983

“Hi, sweety!”

I watched as Jake’s eyes widened comically at Shelly’s public nickname. Even my girlfriends had never embarrassed me by calling me something like ‘sweetheart’ in front of another guy!

The mind is a funny thing. It can operate at what seems like light speed one moment: I had registered Jake’s wide-eyed response in a nano-second. Then I had arrived at a long, convoluted story in which Jake backed away in horror from Shelly’s crude attempt to cause me discomfort. She must be messing with him, and me, right?

The mind can also operate at what I like to call ‘sludge speed’. Like when my best buddy stepped forward, took hold of Shelly, and kissed her. Vigorously. With tongue, if I’m not mistaken. I might be mistaken. I might be oxygen deprived, given that even my lower autonomic functions have gotten stuck in ‘sludge speed’, and I apparently stopped breathing the whole time that they ... well, also weren’t breathing - together.

But they did kiss - did I mention it was a vigorous one? - and then Jake did something that totally destroyed my desperate hope that they were both just messing with me. He reached down and ‘adjusted his package’. Kissing my ex-girlfriend had given my best friend a chubby.

I choked. On spit? On my utter confusion? Or maybe it was just the realization that I needed air. Who knows, all I was sure of was that the next thing I knew I was seeing spots, and Jake was pounding on my back. Too bad I hadn’t been timing things, I might have just broken my best friend’s record for holding our breath. Were we still friends?

When I could finally make sense of his words I realized that Shelly was nowhere to be seen.

“You ok, dude?” asked my maybe ex-best friend.

“Yu ... you, ah, and Shelly?” I stuttered out. I had no time to compose myself, but since Jake was gazing off towards the girls changing rooms, he wasn’t bothered by my baffled glare.

Jake’s gaze softened, and his head bobbed twice as he continued his stare into the distance. “Yeah. I’m so glad you broke things off with that babe last year. I had no idea her family ran into money trouble, but I know that was way before you went solo with Michelle. We met at that public school meet you missed in July. She and I dated through the summer and, uh, well...” It was Jake’s turn to stammer a bit, and the glaring lights showed the red flush creep up his cheeks and even down his neck.

I had no time to ask what he meant. Well, I was in no condition to take the time, let alone un-sludged enough to make sense of things. Too much information was jammed up behind the fact that Jake really was dating Shelly.

“We did it!” Jake blurted out, and his words made me start choking again.

He negligently pounded me on the back again and I finally took a deep breath.

“We’re supposed to get together again tonight, after dad goes in for the evening game.” He continued, his words a bit rushed now. He glanced at me with what looked like a mixture of concern and amusement. I had only choked for a few seconds this time, but I had coughed up a huge loogie into the trashcan. But the key takeaway here was that Jake didn’t seem to think anything was wrong with the situation.

“Hey, could you cover for me? I mean, just in case my dad calls your place, back me up that we were out practicing relay grabs at the park?” He scooped my towel off the floor, tossed it to me, and slapped me once more on the back.

“We better get our practice in!” Turning, he walked away just like he would have yesterday. Back when it would have been a foregone conclusion that we’d cover for one another, and he headed towards the area we usually used to stretch out.


Objective reasoning.

Take a step back from the situation or problem, and consider it without any emotional influences. Emotion kills logic and leads to rash decisions, unwise words, and causes more problems more often than not when you are responding to something that has upset you.

It’s one of the few lessons that both of my parents had beaten into my head, and it has been backed up by our teacher that covers philosophy and history. Even Coach has a variation on the theme: “You will lose. When you lose, never use it in your next race. Only run your race, never let a loss make you run angry.”

I was really angry.

I needed to think, not act, not speak, and there was no way I was getting into the pool with Jake right now.

“I gotta evac!” I pitched my voice towards Jake, using our code for a bathroom break.

He waved one arm in acknowledgement, his mind focused on stretching out. And probably stretching out on Shelly. I shook my head to clear the imagery.

I could hear the blood pounding in my ears as I stepped into the bathroom cubicle and carefully set the latch. Evac indeed. I needed to get this maelstrom of churning thoughts out of my head. Part of me was focused entirely on not hitting anything. Part of me was carefully not thinking about how easy it would be to set up Jake to be caught with Shelly. And part of me was very calm.

That’s where I purposefully immersed my thinking. In the calm, trying to be objective.

Shelly left school last spring without saying anything to anyone, not even the few friends she had left after her bizarre change of attitude. It turns out that she hadn’t gotten pregnant, but she cut off all contact because she was embarrassed because she had to start attending public school.

Next, Shelly and Jake met while I was busy with my family. He hadn’t mentioned her though ... and that’s where my calm, objective, logical mind ran into the first mine field.

Why hadn’t Jake mentioned that he was dating my ex-girlfriend? For at least three months! Set it aside.

Dad and Dr. Jules - my philosophy teacher - both agreed that you had to mark the mines to be diffused later. First you had to get an idea of how big the field was. Dr. Jules was a big anti-war protester and had posters showing statistics on the damage caused by old minefields to civilians. The pictures of little kids missing limbs still haunt me when I think about them.

So, first landmine marked. I now considered the fact that my best friend had not only passed third base before me, but he’d scored before I’d even felt under a girls’ clothing. Damn, that wasn’t so much a mine as it was something I’d normally high-five him even as I tried to figure out how to one-up him. Now ... well, damn.

I had no idea what to feel about it, let alone any plans on how to, uh, well. Damn.

I kept going back to how Shelly glanced at me with what seemed like irritation. Or, was it satisfaction? Was she happy to see that I was upset? She was only 13 last year, why did she start getting so focussed on sex? How did Jake manage to get laid before I even got to third base? Who did I even want to get to third base, and beyond, with?

Objective reasoning, meet circular thoughts, why don’t you two sit in those sludge thoughts and get comfy? So I did, sit and spin that is ... my thoughts swirled around in my head with no answers in sight. Calm, objective thinking is all well and good in theory, but it turns out it’s a real bitch in practice!

After the third time someone had rattled my door, I realized that I needed to “shit or get off the pot” ... heh, one of my grandfather’s favorite sayings. I flushed, washed up for appearances sake, and considered my next move. I still had no idea how I felt about the situation.

I needed to avoid Jake, there’s just no way I could hide how upset I was, no matter how “objective” and “reasonable” my thinking was. Psyche! I was totally lost, not thinking reasonable, objective or otherwise.

I needed to relax, and I knew that Jake hated the jacuzzi, while I really enjoyed unwinding in there on occasion.


So, that’s how I found myself in the jacuzzi. With Laurel Andersen. Yeah, that Laurel, the one who pushed Mia down last year and inadvertently triggered our return to dating.

Laurel had been working hard on her training and used the pool regularly. She was one of the older girls in our class, having turned fourteen in September, and her body was quite a bit more developed than most. This was very evident as her lovely breasts (not tits, I remembered!) were ‘right there’ at water-level. Laurel had what I now know as strawberry-blonde hair down to her ears, but cut in a tapered-shag style that made her look a bit wild. Punk rock wasn’t really a thing yet, but she was rocking the look ahead of the trend.

I had sat down right next to her before I’d realized it was her, The jacuzzi is always busy this time of day, so you take the open seat when you find one.

“Hi Jason, did you have a good workout?” She asked, even as I popped my eyes up from her cleavage.

Her voice was actually very pleasant. Her eyes were hard to make out, the lighting in here was terrible, but I remembered them as hazel; an unusual mixture of brown, grey, and even some green flecks. Her acne had also cleared up ... and she had apologized for the fight with Michelle - man, that seemed so long ago now. So, I really had no reason not to talk with her, right?

I was speechless. I knew that she’d had a crush on me for a long time. I was honestly considering dating her by the end of that week from hell when Shelly dumped Mia and I, and Mia wasn’t speaking to me either. From out my sludge thinking I realized that my heart rate had increased, and my instincts were screaming that this was one foxy girl and I needed to impress her!

I had the fleeting, momentary thought of, ‘How could I be smitten with Laurel just minutes after finding out that my best friend was fucking my ex-girlfriend?’

Waitaminute!

Yep, cue the screeching sound effects and sudden stop crashing-noises. The sludge was splattered aside and my mind burst into clarity on the single most important point: EX-girlfriend. Shelly Was My EX! It didn’t matter Why she was dating him. It didn’t matter What they did together. It only mattered that Jake didn’t actually do anything to hurt our friendship. That would have been me had I lashed out. But I hadn’t. Everything was fine!

In my elation over this eureka moment I may have overstepped my bounds with Laurel. As in, I am very happy to report that she didn’t slap me silly when I kissed her - without saying one word to her! I’m also quite pleased to note that she’s a helluva kisser!

“Uhm...” I breathed out, when the throats being cleared around us finally broke through my ardor. “Want to get some DQ?”

DQ, or Dairy Queen, was the local place to go for an inexpensive, yet public statement date. I had for all intents and purposes just asked Laurel Andersen to be my girlfriend. My luck was still holding because she answered with a smile that made my heart-rate redouble, gave me a quick smooch on the lips, and then gave us all a wonderful show as she got out of the jacuzzi tub. She may have been pushing out her chest in that swim team top, but her incredibly tight runners ass was shown to perfection even in the standard issue one piece.

“I’ll meet you out front,” she stated, then grabbed her towel and was gone into the girls changing area moments later.

The faces of my fellow jacuzzi soakers showed various levels of exasperation and a few with open approval, but I think all of them recognized that I had just scored points for the males of the species as she made her exit.

“Damn...” was the only comment out loud, but I answered the sniggers of agreement from around me with a very serious nod of agreement. I had yet to stop smiling.


Laurel and I were both happy and upbeat as we chatted on our bikes. Of course we both rode, there was no other way to quickly get around town without mooching rides. We were both excited to see that we had matching Schwinn Sieras, though I lamented that my dark blue paint was not in nearly as good of condition as her dark brown.

“It’s chestnut.”

“Sorry?” I answered, missing the segue.

“You complimented how well I care for my ride, but it’s ‘chestnut’, not dark brown.” The twitching of her lip and twinkle in her eyes captivated me. I was pretty sure that she was messing with me, waiting to see how I’d respond. I was both smitten and strangely excited by the teasing.

“Hmmm, well,” I answered, riding no-hands alongside her, and holding my chin in the classic ‘thinking pose’.

“Yes, now that you mention it,” I continued, now trying to imitate the lecturing voice of our rather pompous social studies teacher. “That shade of brown could be the approximate nuttiness of certain chests, though a sample taste test would be necessary to validate your contention, or it will remain conjecture, and therefore debatable.” I thought that my voice acting was pretty good as I practically mimicked the toneless, but rambling bullshit that our teacher constantly bored us with.

I was proud of my imitation for about .5 seconds. Then I realized what I’d just said.

Holy Shit! Where did I come up with that, that ... whatever that was? Microsecond-thoughts flashed along my synapses, pronouncing the quick wittedness of my response truly brilliant, except ... Except for the fact that I had basically told a girl that I’d never even held hands with that I expected to taste her tits. Erm, I mean breasts.

Oh, what the hell did I just do? We were having a great time, and I...

“My place is just down this street,” she breathed out, and slowed down. She began to turn down the street she’d indicated.

“Laurel, look,” I began to babble, even as she pulled away from me. I assumed she was ditching me to head home. Probably to start calling every girl in our class to report on what a douchebag I was. I was pumping my legs hard, trying to catch up even as I was desperately trying to find a way to salvage my screwup.

She gave me a shy smile over her shoulder, and I shut my mouth so fast I actually kinda hurt my jaw a little. “I know that you and Michelle must have had a lot of fun together.” Laurel looked ahead as I drew alongside her. “She told me how far she and Shelly went, and she seemed even happier when it was just the two of you.”

I had just processed this new information and began to formulate my reply. Sort of. I actually had no idea what I was going to say, Objective Reasoning had well and truly sunk into sludge thinking. But she saved me from myself again, speaking up even as she slowed to turn into an empty driveway.

“Here we are,” she flashed me a grin, “take your bike all the way around the back and put it into the shed.” She pointed down the side of the house even as she carefully nudged her pristine, chestnut brown bicycle into an obviously reserved spot under the covered front porch.

Laurel looked at me as I stood astride my bike in her driveway. Her excitement was obvious in her sparkling eyes and infectious smile. If that wasn’t enough, the way her nipples tented her t-shirt definitely emphasized that she was not at all upset with the way things seemed to be going.

She was fishing a key out of her jeans as she climbed the step. “I’ll meet you at the back door, my parents won’t be home till late, and I know your folks let you run wild.” She eased the sting of that last comment with another dazzling smile, and regardless of the fact that it was true, she probably could have said that my parents were useless druggies and that smile would have made me nod along.

I met her at the back door, and was quickly inside. I had kind of expected her to put the brakes on at this point. You know, first time alone with a boy in an empty house. Well, first time with this boy. I hadn’t actually considered that I may not be her first!

Anyway, hesitation seems like the logical next step. A bit of shyness that I would somehow have to suavely navigate past to get us back into the mood.

There was no shyness and less hesitation. In fact, she removed her t-shirt and was pulling me down a hallway to her bedroom, no tour today folks, it’s titty-time!

Yeah, my mind was not providing any further witty comments! But I’d wised up and clamped my mouth closed to prevent my addled brain from ruining the moment. I’d also noted that her nipples had been visible through both her t-shirt and a cream colored bra.

The bra that hit the floor as she entered her room.

The closest thing she came to hesitation was when she stopped to close her door behind me, and then seemed to survey her room. I took a moment to look around. It was very girly, very pink, and very clean. “How, uhm, do you want me to, I...”

Ok, here we go, uncertainty, finally! Thank you Laurel for letting me try to catch up to you. My brain has been tackling the last few minutes of dialog and I’d decided three things:

One, Laurel is convinced that Shelly and Mia had gone a lot further sexually than either girl had gone with me, even after the breakup, and even after Michelle and I “dated” for the rest of the school year. That actually made sense, they could have sleepovers, whereas the three of us only had the one time where we ‘slept together’ and (I had thought) we were all traumatized from viewing an orgy together.

Two, Laurel is convinced that Mia and I continued to have a lot of sexual, uhm, relations? Yes, that. And, given that Mia told Laurel that she was very happy with our relationship, it follows that Laurel was convinced that I must be pretty good at, well, sex stuff.

Ahem.

Three, Laurel Andersen wants to do sex stuff with me.

Hah! How’s that for Objective Reasoning?

One minor, teeny-tiny little issue here. I have never actually done any stuff. Sex stuff that is.

“Jason?” Laurel’s smooth, soft voice seemed oddly concerned.

“Mmm?” Huh, I guess I sound a little distracted.

My mind stopped racing and I realized that my eyes were focused on the person in front of me, but I hadn’t actually been seeing her.

I focussed on her lovely face, now marred with a bit of a frown and twinkle-less eyes.

But I couldn’t stop myself from sweeping my gaze over her body. Over the gloriously naked young woman, laid out in a somewhat awkward posed stretch, on her bright pink bedspread with tiny hearts, unicorns, and big puffy silver clouds. The clouds were dotted here and there, and one looked to be almost drifting in front of the first real-live pussy I’d ever been this close to. It was shaved. The pussy, not the cloud, but that made sense because Laurel was on the competition swim team and oh my God, I need to figure out what to do before I sink like a proverbial stone.

“You are, without a doubt, the most beautiful woman I have ever seen.” I said it in one, long breath, barely avoiding turning it into a moan. Her frown reversed course, and she actually ducked her chin a bit in embarrassment.

And she was. Beautiful. Truly, she was more beautiful than any other naked woman I could recall seeing. I mean, I’d seen a few dozen naked women while spying on my parent’s parties in these last few months, but never this close, and never ... waiting for me.

Her upper chest was sparsely freckled on a light tan above the line of the swim team’s one-piece swimsuit. Below that, the expanse of pure, white flesh was unmarred except for a small mole just left of center and above her breast bone. Her breasts were gravity defying and shaped like perfectly round half-cantaloupes, capped with bright pink pencil-eraser nipples on creamy light pink areola. Her waist was slim, her tummy was not muscled but certainly had no fat. Her hips were still pretty narrow, though the flair from her waist was still noticeable. Her legs were the most obviously muscled part of her body, and in her slightly bent at the knees pose, still looked incredibly long. Her pussy was now hidden as she had drawn her legs together, but I wasn’t going to complain.

I met her eyes, her twinkle was back, though her smile was a tiny bit strained.

 
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