I Am Jack's Life Ch. 11

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A coming of age story.
5.5k words
4.69
18.5k
6

Part 11 of the 19 part series

Updated 10/31/2022
Created 01/30/2015
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Author's note and acknowledgements

This story has sat on my hard drive for four years now.

I wrote it, all twenty chapters and 95,000 words of it in eight days of a frenzied, near trance-like state, sitting on my couch with my wife's laptop. She would occasionally have to remind me to eat.

When the dust settled, and I looked up, I realized a couple of things: one, I had just written a fucking novel in a week, whoa. Two, it seemed to be pretty damn good, double whoa. And three, what the hell was I going to do with it?

I tried editing it, I even enlisted the help of a Lit-Editor, who was invaluable for early editing, and confirming it was in fact, pretty good, or readable at least. I spent several months then, editing, unashamedly forcing it on writer friends to read, regular friends to read, and total strangers on writer boards. Everyone had different opinions of course, as people do, but all of them seemed to think it was pretty good, and I should probably try to do something with it.

So I spent another year trying to sell it.

Well nothing happened.

And I can't blame them, agents and publishers. It's kind of a niche story, hard to market. It's got too much sex for a coming age story, too much teenage drama for adult fiction, and not a single word about vampires or bondage to make it work as erotic fiction.

So it's sat on my hard drive for four years. I'll occasionally open it up, tinker with a line, or try to figure out how to re-work it into something more marketable. I always end up wasting a weekend trying to figure out how to change it, without losing the essence of the thing which I, and several others, feel is, "pretty good."

So fuck it. Here you go Literotica. I just want people to read it. I want people to get to know Jack the way I did. Writing his life made me feel like I was a part of it. He's a pretty good guy, I wish I knew him in real life.

So NEXT, some disclaimers.

This is a coming of age story. Which means first it starts out when the characters are too young to have sex (on literotica.) So there's no sex for a couple chapters. I hope that's okay. Second, this is a novel length story, including the prologue and epilogue, there are twenty-one chapters in all. Some are longer than others, and there is not a sex scene in every one. (Though some have more than one.) More importantly, sex is a thing that happens, it's not written to be titillating, but rather just as events in Jack's life.

So there you go. It's a story with sex in it, not a story about sex. I think it's pretty good anyway.

If you have not read the first chapter, please click on my profile and pick the story up at the beginning, its better that way, trust me.

*****

By my nineteenth birthday, Anna and I were sleeping together.

Yeah, Kimmy and I were still together - mostly. I guess. We weren't officially broken up or anything. It was complicated.

Actually, twenty years later, it seems pretty simple.

After graduation Kimmy had to get a job, since she wasn't going to college. So she got a job as a waitress at a local diner. Being the low girl on the totem pole, she ended up with some pretty crazy shifts. When I'd pick her up after work, she'd be tired, grumpy from rude customers and smell like stale coffee and grease. She'd generally be in no mood to come hang out with the rest of us or even just me. By the end of the first month of summer, we'd hardly seen each other at all.

The other very big factor that strained our relationship, was my acceptance letter.

In September, I was headed off to Stanford.

At first when I'd gotten it we'd had a party for the five of us. Kimmy was super proud of me and I was still riding the high from commencement. By the end of that week though, she'd gotten moody, withdrawn, and depressed. I knew it was because I was leaving for a big fancy college and that she was staying to be a waitress, but there was nothing I could say.

All of us were leaving Kimmy actually. Beth had been accepted to USC, which was only about two hours away, but it was still 'Away', Abby had also decided on UC Berkeley, and worst of all - Anna was also going to Stanford.

I think it was the last part that bothered Kimmy the most. That Anna and I would both be going to the same school.

Anna was actually going on an athletic scholarship for track; which was a huge, huge deal. Stanford woman's athletic programs had turned out more Olympic gold medalists than any other college in the United States. I've kind of glossed over it, but Anna was a champion cross country runner, she'd taken fifth place in state our senior year. When your state is California, that's a pretty big deal.

Kimmy didn't take any of this well, so we started having fights. About little stuff. I don't even remember what most of it was about, but it made our time together uncomfortable, and I made less and less effort to make time for just the two of us.

Anna on the other hand, was plenty available.

About five weeks before mine and Beth's nineteenth birthday - which was another big planned party to send all of us off with a bang - Kimmy and I had a pretty intense fight. She said some hurtful words. I don't remember what they were, but it was on the way home from dropping her off at home from work. I just remember I left her in her drive way and drove away pissed. I had every intention of driving home, but some how, I ended up in front of Anna's house.

It was late, probably about one in the morning; Kimmy had been working the late shift. I sat in my car parked across the street wondering what I was doing here. Anna's bedroom light was still on. I had every intention of just turning the car back on and driving away as soon as the song on the radio was over, but then the front door opened and she came walking out toward me.

She was wearing an oversized jersey for the Lakers, and a pair of shorts and flip flops. I didn't really look at her as she walked up, until she knocked on the driver's side window.

I rolled it down and looked over at her. She was smirking.

"You going to come inside or sit out here all night thinking about it?" she asked.

"I hadn't decided," I said flatly.

"Let me help you," she said and leaned in and kissed me.

Goddammit, it was a sexy kiss; full of promise and desire, full of passion and need. Kimmy and I hadn't kissed like that in weeks.

We stopped kissing and I got out of the car in a daze. She took my hand and led me inside. We went into her room and she shut the door.

We kissed again. I wrapped my arms around her and pulled her close, she folded into me like the world was ending. We kissed - and it was fucking sexy. I was cheating on Kimmy. I didn't care. I wanted Anna so very badly, and I knew she wanted me just as much.

I pulled her jersey off and she was naked underneath. Her breasts were full and heavy, so much larger than Kimmy's. I filled my hands with them and we fell onto her bed kissing.

She giggled and shushed me through her giggles. I grinned back and shushed her giggles with my lips. My shirt came off next and we pressed our bodies together. Her breasts were large, soft, and warm against my skin. Giggling turned into passionate panting, and panting turned into quiet moaning. I pulled her shorts off with a couple of quick tugs, and she lifted her ass up off of the bed to help me. I kissed my way down, stopping to lick and suck on her nipples roughly as I did.

She was trimmed much neater than Kimmy currently was, waxed for bikini season; and I dove in, pressing my tongue into her waiting crotch like a starving man. She gasped and covered her face with her pillow. I used every trick I'd learned from my time with Kimmy; swirling my tongue around her clit, teasing and taunting her. In moments, her whole body was flushed and she was panting hard and biting her lips to stay quiet.

I really didn't want her to be quiet, but her parents were home, so I accepted it.

She came in a rush, bucking and thrashing against my face. She was much more erratic in her movements than Kimmy. It took me by surprise. I had to hold on to her legs so she didn't throw me off.

Then she started slowing down, I backed off and slid up her body, every intention of penetrating her and fucking her until dawn.

She had other ideas.

She sat up and kissed me hotly, she put both of her hands on my face and just held me, kissing me with increasing slowness and tenderness. I wasn't really in the mood for tender, so I started to push her back so I could climb on and get to business.

"Not yet," she whispered softly.

She pushed me around and she switched place with me, straddling me and leaning over me and continuing the soft tender kisses. I suppose she had waited for this longer than I had, so I relaxed and let her take the lead.

When she felt me relax she sat up and gave me a sexy, secret smile, full of delight and hidden agenda. It's a good look for a sexy, naked blonde straddling you.

She reached over to her nightstand and got a hair tie. She pulled her hair up into a pony tail, which caused her heavy breasts to sway above me with the movement. I watched in fascination, I couldn't stop comparing her body to Kimmy's. Kimmy was tall, but petite in frame and bust. Anna was about six inches shorter, but solidly muscled and toned, with large breasts and curvy hips.

Anna finished with her hair and leaned down to kiss me again, there was a lot of tongue. She also kissed a lot differently than Kimmy. Her tongue was all over the inside of my mouth, trying to twist around mine. It wasn't what I was used too, but it was just as hot in it's own way.

She breathed out in a slow moan as the kiss ended, she sat back up with a dreamy look on her face.

"I know Kimmy hasn't done this for you yet, she told me she thought it was gross," She said, and sat up and tugged my pants down. I sprang free, fully hard and erect.

I swallowed, a fair idea what was coming next.

Anna looked at me sultry and dreamily, "I want to be your first something Jack, looks like I get to be your first blow job."

Gulp.

She moved off of me and knelt over to one side. She took my cock in her hands and lowered her face down to me. She stroked me a few times, and then lowered her tongue down and licked up along my shaft.

Now it was my turn to start panting.

I'd never asked Kimmy to do this. I knew she didn't like the idea and I didn't want to push her. I never minded going down on her, and she used her hands on me all the time. But this was a bridge we'd never crossed. I just wasn't going to ask her to do something she wasn't comfortable doing.

Anna on the other hand, looked up at me like I was doing her a favor, and my cock disappeared into her mouth.

Warmth and wetness, I felt her tongue move against me. This was similar to being inside a girl, but different enough that it was a new experience. I watched for a couple of strokes, and then she closed her eyes and started concentrating on pleasuring me by pulling me even deeper into her mouth and down her throat.

My head fell back against her head board with a thud.

It went on for quite a while. Maybe because it was a different sensation than I was used too, maybe because neither of us were trying very hard for me to get off, but I wasn't really that close when she pulled off of me and slid back up to kiss me. It felt plenty good, and I'd be lying through my teeth if I said I hadn't loved it, but I still had a lot of stamina left in me.

We kissed passionately, and her mouth was warm and hot - from me I suppose - but that just made the kiss sexier. She straddled me and her hand reached down between us and guided me inside of her. She was wet and ready and I was as hard as granite, so penetration happened quickly. Once again, I marveled at how different she felt, and she gave a sudden whimpery gasp against my lips. I held onto her waist and we moved together, quickly finding a rhythm that was comfortable for both of us.

I guess we'd moved to the stage were we both wanted to prolong it, rather than just get off, or at least I did, and met up with her because she'd already been there, because we slowed down and just took pleasure in each other. We kissed, and made love, and kissed, and petted each other every where our hands would reach, and kissed, and panted into each other.

I'm not sure how long things went on like that, time dilates funny when you're having sex. Minutes become hours, and hours snap to minutes. It felt like hours, but could have been as little as twenty minutes. It felt like a long time.

Here's the weird and remarkable thing though.

I'd been with Kimmy plenty of times. Dozens, easily. We'd been sexually active for over six months by this point, and we liked having sex with each other quite a lot.

But this time, this first time with Anna where neither of us were wasted drunk, this felt like the first time I was having adult sex.

Which is weird to say, but weirder to experience. I didn't feel like I was fumbling around with my teenage girlfriend, I felt like I was with a sexy woman, pleasing and being pleased in a choreographed dance of skin and sex.

It made the whole thing much hotter than any time I could remember with Kimmy. Maybe it was the body differences between Anna and Kimmy; Anna was much closer to my 'type' than Kimmy was.

I just don't know.

Eventually, I rolled her over onto her back, and managed to stay inside her. I kept thrusting and we made eye contact. We held each others gazes as we gently thrust against each other. She reached up and pet my cheeks, and I wrapped my arms under hers and propped myself up, every intention on staying there for a good long time, maybe forever.

She bit her lip, and I could see she was starting to get close, so I picked up my pace ever so slightly. She responded by panting and arching her body against me, trying to maintain as much skin contact as possible. I held her, and she came. I did too, but my orgasm was just that.

Her's rode through her like wild mustangs, and she gasped and pawed me, trying to pull me even deeper inside of her. She kissed me hard as we finished, and when we pulled apart, panting and spent, I could see tears on her cheeks.

Now, I started to feel guilt. She loved me. She was in love with me, and I don't know if I was with her or not, but I'd just wanted to have sex with someone who wanted me around.

I felt like I'd used her.

I suppose I kind of did.

I kissed her cheeks gently, and wiped her tears with my thumbs and held her while our breathing returned to normal.

I had to say something. We had to talk, I couldn't just get up and leave.

I started to get up, and she pulled me back down to her, wrapping her arms around me tightly and holding me inside of her

"Not yet Jack, please," she whispered.

I swallowed hard, the guilt really starting to settle in now. But I lay back down against her. Eventually I rolled slightly to the side of her and she clung to me, nestling her head under my chin.

I meant to say something. I didn't want to just use her and not say anything.

But I fell asleep.

We had sex every night that week, each time was just as amazingly hot as the first. She seemed determined to impress me with her willingness to please. The day after the first, we woke up and her parents were gone. We showered together and fucked against the wall in the shower. I couldn't help but draw parallels with Kimmy, but I buried my confusion hilt deep in Anna's willing legs. I left that afternoon and we still hadn't talked. That night she came over to my house and we fucked again in my bedroom on the floor. Each time the floor creaked I panicked - I'd never had sex at my house before. She left after I'd fallen asleep. Then again the day after that when I drove over to her house again after midnight; and again the next day after her parents left, on the couch of her living room, and the floor of her kitchen.

I still hadn't said anything to her yet.

But then again, she hadn't asked me any questions either.

Sometimes there just isn't anything to say.

We cooled it off for a couple of days when Kimmy's work week ended. The five of us went to the beach and tried to have a good time. I was in a state of fear the whole time. Anna and I tried to act like normal, and she mostly ignored it when Kimmy was affectionate with me, but I was stabbed with guilt each time. I'm not sure who I was more guilty over betraying, Anna or Kim.

It was strained though, Kimmy was trying too hard to be normal and casual. She ended up snapping at me over something stupid, like what kind of drinks I'd brought. Anna kept quiet when normally she'd have quipped and come to my defense, defusing the situation with a joke. I just took Kimmy's complaints silently. I think Abby gave Anna and I an odd look, but she didn't say anything either. We ended up quitting the beach early and I drove Kimmy home.

Anna and I didn't hook up again until a couple of days later. I told myself it wasn't going not happen again, and that lasted exactly one half seconds into me being around Anna. I drove over to her house to talk, but there was no talking, she just kissed me at the door and pulled me to her bedroom. I was inside of her within two minutes of the door closing.

By the time the birthday party was just a couple of days away, Anna and I had been together dozens of times. Sometimes so often, there had been a couple of days that left us both raw and sore. Not that it stopped us.

It was the Wednesday before the Friday night party that Anna finally asked me a question. It was very late, and we were in the back seat of my car. We'd drive out to mine and Kimmy's spot and made love for at least an hour. I say made love, rather than fucked, because while I'd brought her out there to fuck her, Anna had come out for something else, so it had ended up being very slow and affectionate; tender and confusingly emotional.

We were cuddling in the aftermath, when she spoke up.

"What are you going to do about Kimmy?" she asked.

"What do you mean?" I asked, thinking that she was talking about the party, "I'm going to the party with her, or at least that's the plan." I said. Guilt set in like a early winter frost.

"That's not what I meant. I mean this fall, when we go off to school," she said.

"Oh." That.

"Are you going to break up with her? I mean officially," she asked. Her voice was carefully guarded.

I sighed, "I probably should."

She sat up and looked at me. I couldn't meet her gaze.

"You know I don't mind this, right?" she said after a second.

"Having sex together? I couldn't tell." I hid confusion under sarcasm.

She didn't bite my bait, and shook her head, "No, the sneaking around. I don't care, you know."

I sighed again.

She ran her finger along my my chin, it was a very affectionate gesture.

"I told you before, I'd have stolen you away from her in a second if it wouldn't have made you so unhappy. You were happy with her, now you aren't, so in my mind, that makes you fair game."

I swallowed, "You make it sound simple."

She nodded, "That's because it is. Are you happy with her?"

That was it, the forty thousand dollar question. Was I happy with Kimmy any more?

I guess I was quiet too long.

She leaned over and kissed the side of my lips ever so softly, and then in the most loving and affectionate tone I'd ever heard from her, she said, "That's a 'no' then. It's okay you know. People grow apart. I doesn't mean you didn't love her, it just means you both have grown apart now."

I sighed.

Finis
Finis
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