The Katie Chronicles Ch. 02

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Katie takes a friend's virginity.
6.7k words
4.73
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Part 2 of the 2 part series

Updated 10/17/2022
Created 08/13/2004
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SallyG
SallyG
272 Followers

Hi, Katie again. I want to tell you a story about a boy I know named Jason Goldman.

Jason and I met each other when we were in Mrs. Lipton’s 2nd grade class, which now is about 10 years ago. We were friends in those days, since we lived on the same street, and our parents knew each other. Mr. Goldman taught political science at a near by University, and I remember my Dad and he would constantly argue about politics.

Jason used to walk me home everyday, and we would tell each other everything. Everything was, of course, a fairly limited subject for two eight year olds, still I remember once when my sister asked me who my best friend was, I told her Jason.

The next year we were placed in different 3rd grade classes and we began to see less and less of each other. I became friends with a group of girls who were, even at the time, considered popular and Jason began hanging out with the kids who would later become known as the dorks of the school. As the years went by we would still talk from time to time, but I would always get the feeling that my friends were laughing at him when I spoke to him, so it made me uncomfortable. I have a vivid memory of Jason approaching me at a 6th grade social , and asking me if I wanted to dance right in front of my friends. I laughed at him and said, “no” which put all my friends into a giggling fit. Poor Jason slunk away dejected. I remember feeling afterwards like I should apologize, I had intended to say something to him, but I never did.

By the time we reached high school my family had moved to a much nicer neighborhood and I no longer even saw Jason around on the street. In freshmen year, I started dating Chip Bennett who was a senior and captain of the wrestling team (and a real dick I later found out).

For some reason, which had nothing to do with our long ago friendship, Chip took a dislike to Jason and a few of his friends, and would pick on him whenever he saw him. It seemed that upper classmen liked to find freshmen to pick on, and that year Jason was one of the unlucky chosen. A lot of times Chip and I would be kissing next to my locker and Jason would walk down the hall and see us and would turn tail and run. Chip would laugh and yell after Jason, “Run Fuck Nuts!!”, and I would laugh like an idiot, pretending that my boyfriend had a sense of humor. Later that year I broke up with Chip when he tried to date rape me in the back of his IROC and take my virginity - I wasn’t ready for that and kneed him in the groin to put an exclamation on the point. He drove me home that night in silence (except for the sound of me crying) and that was the end of our relationship. As far as Jason went, we never really spoke the last few years of high school.

Which brings me to what happened recently.

Two Sundays ago I went to the beach with my friends Robyn and Nicole. We spent the day playing Frisbee, tanning, and flirting with some really cool guys we met who were visiting from Australia. If Robyn hadn’t had to get home by 5 (to go to some dinner with her Dad) I probably would have hooked up with this one awesome guy named Derek, but Robyn had to run and as things turned out, I’m glad that never happened.

On the way home I asked Robyn to quickly stop at the gas station so I could pick up a bottle of water. When Robyn pulled in to the station she almost crippled this Asian guy who was minding his own business trying to put air in to his bicycle tire, and he looked up at her and angrily said, “Why don’t you watch where you’re going?”

The situation was quickly diffused by Nicole (who looks like a super model) getting out of the jeep and going over to the guy to apologize. Now you’d never know it to look at her, but Nicole is a very warm person, and when the Asian guy (who must have been in his 50s) really started to act up, I saw Nicole do something that I’ve seen her do dozens of times – she grabbed the man’s hand and gently held it. You would have thought she had just told him that she loved him, you could literally see the anger melt away, and he was all smiles and avuncular advice after that. When they parted and said good bye they seemed to have a genuine human moment. It was fascinating to watch.

After they said good-bye Nicole walked back over to Robyn and me and under her breath mutter, in a fantastic faux Asian accent, “Why don’t you watch where you’re going.”

Robyn and I started laughing and we continued to laugh as we entered the store, pushing and shoving and repeating the joke over and over again. Being slightly drunk, having had too much sun, and being horny from flirting with cute surfer boys causes one to be a little on the silly side.

As we entered I immediately caught sight of Jason, working behind the counter, in his company issued polyester pull over – and I laughed –then caught myself. I grabbed my bottle of water and stopped to talk to Nicole who was admiring the chips and dips rack (such items would never, in Nicole’s food obsessed world, actually make it in to her mouth). When we got to the front counter, Robyn was already there rummaging though a tray that contained cheap lip glosses.

Although I wore a wrap around skirt over my bikini, I still had nothing over my top and the air conditioning was having an effect on my nipples, a condition that smart-ass Robyn did not fail to notice and comment on.

“Hey, Jason, you might want to frisk her it looks like she’s smuggling erasers out of here,” and then she added, “Take a good long look, Jason, that’s the closest you’ll ever get to those magnificent beauties.”

Jason, who was kind of just standing there looking at my breasts, blushed a deep crimson and looked down at the register. I punched Robyn on the arm and told her to shut up. Robyn laughed like a hyena and shouted, “Well it’s true!”

I apologized to Jason telling him that Robyn was drunk, but he just looked at the register, as he rang us up, not saying a word. A tried to smile at him when we left, but he turned away.

When we got outside Robyn was still rattling on about something, but my mind was elsewhere. When she called my name for the second time to get in to the Jeep, I told her that I was just going to walk home (it was only about a mile from where we were). Nicole looked at me and smiled, and Robyn shook her head, looked at me suspiciously and drove off.

I started walking home, but only got a few feet before I turned around and went back to the store. I wanted to say something to Jason, I just wasn’t sure what.

I had always prided myself on connecting with people, I like making people feel good when I deal with them, and I hated that idea that somehow someone I once knew didn’t even like saying two words to me now. I was ready to admit that we had grown apart, and I was ready to admit it was my fault, but at least I could remind him that we were once friends. I’m not sure why but the idea seemed really important.

When I entered the store Jason saw me immediately and quickly averted his eyes. I walked right up to him.

“ I really am sorry,” I said, flashing him a big smile, “ I know Robyn can act like an idiot.”

“It’s alright,” he muttered under his breath, “ doesn’t matter anyway.”

“Oh it doesn’t, I’m sorry I thought it did,” I started to leave, I didn’t know what to say to that. I had taken a few steps towards the door, when I heard Jason call after me.

“What does it matter to you anyway?” He sounded very sorry for himself.

“We were friends once, Jason.”

He looked at me with a sad expression and finally said, “ That was a long time ago.”

“We’re only 18, nothing is that long ago,” I said.

Just then his manager, an Indian man in his 50s emerged from the back room, he smiled at me and looked at Jason.

“Jason, your shift is almost over,” he said, “it’s alright, if you want to leave a few minutes early to be with your girl friend.”

I could tell Jason was about to correct his boss’s mistaken impression so I jumped in, and flashing my most flirtatious smile, I thanked the manager for being so kind. Jason said nothing so I asked him, if I waited a few minutes for him, would he take a walk with me. He nodded his agreement.

I waited outside for him, and 10 minutes later, Jason emerged wearing his street clothes, a plaid shirt and blue jeans.

If one wanted to be generous, one might say, Jason had an interesting face. He was not by any stretch good looking, he has a large nose and his eyes seemed to close together. He wore his hair fairly long, but not as a style, more because he seemed uninterested in going to the barber. His hair was somewhat wild an unkempt. He was thin, but had no muscles, and he was about as tall as I was – 5’6. Physically he reminded me a lot of the actor Dustin Hoffman.

If anyone had seen the two of us together anyone might have been forgiven for wondering, “What is she doing with him?” I had gone through high school thinking thoughts like that, and discouraging guys, who I didn’t see up to my physical standards, from trying to talk to me. But, recently Niki and I had discussed that very subject and we had come to the realization that it was a shallow and negative way to live – we had taken a vow that day to change the error of our ways (Robyn had steadfastly refused to take the same vow).

So that afternoon Jason and I took a long walk, up through the woods, to the little old cemetery that was up on a hill that over looked our suburb.

As we walked we chatted, at first somewhat uncomfortably, about our lives and our plans for school in the fall (Jason was going to Yale), and our childhood’s.

By the time we reached the cemetery, and had found a tree to sit under, I could tell Jason was holding something back, so I asked him what it was. He hesitated a long time before answering.

“I’ve kind of have hated you the last few years,” he finally said.

“You hated me?” I replied. I had no idea.

“Well, I didn’t really hate you,” he quickly added, “I guess I was just angry.”

“I don’t understand.”

“You used to ignore me when you were around your friends,” he said, of course he was right about that, “ and then you dated that idiot Chip Bennett.”

“He was an idiot.”

“But you dated him anyway,” he continued, “because he was good looking and he had the right car, and he was captain of the wrestling team. You know how lousy it made me feel that this knuckle dragger was sleeping with the prettiest girl in the school, while I couldn’t find a girl to hold my hand. Knowing that asshole was having an experience that I could never have. You really have no idea what it’s like to be on the outside looking in all the time – ”

“You really thought I was the prettiest girl in the school?” I asked. I was really touched by that for some reason.

Jason seemed a little taken aback by the question. For a moment he was flustered and then he half-heartedly nodded yes.

“Well, and not that it’s any of your business, but I never slept with Chip Bennett”.

“You didn’t,” Jason said, looking the happiest I’d seen him look in years.

I shook my head. Jason’s happiness only lasted a moment; he was soon back to his semi-miserable self.

“What’s wrong now?” I asked.

“Nothing, it’s just that, even though he never slept with you, he still got to hold your hand, he still got to kiss you, he still got to - be with the girl everyone wanted to be with.”

“Not for long, I was 15 when I dated him, and he was a real jerk,” I said, “ I wouldn’t give him the time of day now – I certainly wouldn’t go back in to his store and ask him to take a walk with me,” I told him.

“But, his kind of guy, will always get pretty girls to be with him. I haven’t even kissed a girl yet.”

He was really starting to feel sorry for himself.

“Jason, you and I are friends,” I said.

Jason got up and walked a few paces away from where we were sitting.

“I know that,” he said, “ why do you think I wouldn’t know that?”

“That’s not what I meant.”

“I know what you meant, you meant that we’re friends and you wouldn’t want to ruin our friendship, you don’t feel that way about me,” he said as if he were reciting a long ago memorized speech.

“Do you want to know what I meant or are you just going to carry on a one sided conversation?” I asked.

“No, no,” he said lightly, “I’m interested in having a two sided conversation – I’m just not very good at it.”

I laughed. Jason was kind of cute when you looked at him the right way. He was sweet, and smart, and actually had something to say.

“I meant, that we are friends, and that friends from time to time, when they’re not seeing anyone else……can kiss. Or fool around a little.”

That stopped him in his tracks, I could tell he wasn’t expecting that. I noticed him shift a little uncomfortably in order to hide a rapidly growing hard on. That was quick.

“What?” Jason said in a voice that was almost an octave higher than where it usually was.

“It’s a nice day I thought we could fool around a little before we went home,” I said matter of factly.

Jason came over and sat down next to me on the grass.

“What do you earthlings mean by fool around?” He said in a robotic voice.

“First of all if there’s going to be any of this Star Wars convention crap, I’m going home right now,” I said giving him a disapproving look. He laughed.

“That was it. I got that out of my system,” he said quickly, and then added, “you said something about kissing earlier, how…..um….how…..how would we do that?”

“Have you never really kissed a girl?” I asked him taking his hand in mine.

He shook his head no. I gave him a reassuring smile, and brought his fingers to my mouth and gently kissed them. His hands were trembling a little.

“OK, now normally I would suggest you might want to take the lead with a girl, but maybe seeing how this is your first time I’ll kiss you first.”

“That sounds really great,” he said eagerly. Jason was really shaking now.

“Are you OK?” I asked.

“I’m really good, although, is this normal for my heart to be beating this fast?”

I put my hand on his chest and his heart, was indeed, beating rapidly. I assured him that I thought he would be all right. Not wanting him to have anymore time to get worked up, I leant forward and kissed him on the lips. Jason had his lips slightly parted and he responded to my lips pressing against his, by pressing back in to me a little too hard, but when I moved my hand to his face and put a little pressure on his jaw, he immediately eased up. As we kissed our mouth began to open a little more, and our tongues made their first, tentative contact. He tasted good - sweet and clean.

Our kiss lasted for almost a minute, with Jason gaining some confidence as our tongues continued to gingerly move around each other. As far as kisses went, it wasn’t lustful, but very comfortable (at least for me). When we finally broke, Jason’s eyes shone at me.

“Mmm,” I said, “that was nice.”

“Nice, that was amazing.”

He moved towards me, and in a moment, we were kissing again. Jason eased on top of me and I pushed me backwards until I was lying on the grass. This time he was being the aggressor and I went with it, with our tongues now doing battle, I felt the thrill that I so often do when being kissed by someone for the first time. Nerdy Jason was starting to turn me on.

As he kissed me I began to notice he was keeping his hips from pressing in to me and he was making sure his hands didn’t roam past my shoulders and neck. Every time he came close to letting them wander down to my exposed midriff he would quickly move up again. Once I noticed this behavior I had to stop kissing so that I wouldn’t start laughing.

“Jason are you trying NOT to touch my body?” I asked him, when we broke apart.

“I didn’t know if that…. was allowed,” he stammered.

“It’s allowed,” I said laughing at his sweetness, “we’re fooling around, silly, you can touch me anywhere you like.”

I could tell he was trying not to look at my breasts, but I was pretty sure that’s what he was thinking about when I said that.

“Do you want me to take my top off?” I asked him.

“This is a dream, right?” Jason said, “I’m about to wake up any second and this will all be over.”

“Life is but a dream, Jason,” I said laughing at him, “better go with it until you wake up.”

I sat up and unclasped my top and pulled it off. Suddenly I was sitting there in front of Jason with my chest completely exposed to him. I gave him a big smile.

“And Robyn thought the closest you’d get to them was looking from behind the counter,” I said laughing.

“She was right about one thing,” Jason said in a somewhat shaky voice, “They are magnificent.”

I smiled again at him, “Let’s stop talking about them like they’re separate from me.”

“I’m sorry,” Jason hastily replied.

“It’s a little chilly up here, compadre, if you’re not planning on touching them, I’m thinking of putting my top back on,” I said.

Jason quickly moved towards me, and pushing me backward to the ground, began to suck on my tits. It was an awkward move, and I would have laughed but his ministrations were rapidly having an effect on me. His licking and sucking were really beginning to turn me on, and when he ran his tongue along the line that the bra’s under wire had caused it really made me go wild. My hands flew up to clasp his head to my naked tit.

“Oh my God, Jason, that feels so incredible,” I cried out.

As he moved back up from my breasts to my kiss my mouth again I could sense something wasn’t quite right. I realized Jason was intentionally holding his body away from mine, trying not to let his erection rub against me.

“Jason I want to be naked with you,” I whispered in his ear.

He sat up and gave me a look of such adoration that my heart melted. He began to take off his clothes. As he did, I undid the wrap around that I was wearing and laid it out on the ground. By the time I was finished I looked up to see Jason, now nude, looking down at me. I gave him a smile, and lifted my butt off the ground and pulled my bikini bottoms off. Jason had become only the third guy from my high school ever to see my exposed blonde muff.

His appreciation was apparent. His cock, which was already erect, gave a lurch and almost slapped against his body.

Jason’s body was actually pretty good, he wasn’t as muscular as most of the boys I dated, in fact he was on the scrawny side – but he still had pretty good definition. His cock was a good six inches and, although not terribly thick, had a nice circumference. What struck me about it, was how pretty it was – now I know that wouldn’t be the first word most men would want to hear when it comes to their cocks, but it’s a good word and men should be proud to hear it. Jason’s was smooth and had a lovely well-proportioned head.

I held out my hand to him (Grateful that I had my fingers and toes done the day before by my little Vietnamese manicurist, who had talked me in to a beige-silver color called satin doll, which looked quite nice in the sunlight), and Jason took it and moved back in to my arms.

“Katie, I need to ask you a question?”

“Now?” I said.

“Yes now,” he said, “ I can’t believe I’m asking you this, but are you doing this because you want to, or because you some how feel bad about --- I don’t know, you feel bad for me.”

“Shut up, Jason,” I said to him while looking him straight in the eyes, “the truth is, like everyone else I know, I have no idea why I do most things….. All I know is right now I’m happy to be here with you.”

Jason kissed me passionately as we fell back on to the ground. He was shaking pretty hard and his body temperature seemed to be on the rise, he was almost feverish.

I gripped his strong erection and smeared the mushroom head of his cock with his pre-cum juices. He gave out a whimper and I felt his erection lurch in my hand again. I started rubbing it against my neatly trimmed pubic hair.

SallyG
SallyG
272 Followers
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