Hollywood Jim: The Early Years Pt. 02

Before he was "Hollywood Jim" in Los Angeles, he was a geeky kid with a funny nickname in the suburbs of Connecticut. And before he had numerous starlets as friends, he had various girlfriends. Here then are the "Adventures of Hollywood Jim-The Early Years"

The night at Rose's was certainly revealing on many levels. To put it mildly, she blew my mind. In more ways than one!

I went back to my summer routine, whatever that was. My old high school was just down the road and I began going over there to run around the track. My friend Chris was down there a lot, he lived nearby so we'd eventually hook up at his place, as he had a pool so I was always welcome to use it when he was there.

This day it was quite hot so I did an easy run around the track. There were a few guys playing football, probably reliving the past season's glories. When I stopped for a water break, I saw a pretty girl doing an equally measured run by me. She had on a blue Nike tank top and yellow shorts. I watched her as she went by me twice, she shot me a glance as she passed a third time. Kinda nice looking, I thought. She had mousy brown hair tied in a ponytail that bounced along as she ran. She came around again and slowed to a stop in front of me.

"I think I know you from somewhere." She said.

"Well, I'm from somewhere, does that help?" I replied.

She laughed.

"No, you look very familiar, did you go to school here?"

"Yeah, just graduated a few weeks ago." I said.

"I went to Conard High, so we didn't graduate together." She said while thinking. "Did you go to Junior High here?" she asked now.

"Yes, King Street Junior..."

"That's it!" she exclaimed.

"That's what?" I asked.

"King Street Junior High! I remember you now! Jim, right?" she said with excitement.

"Yes, but who are you?"

"Dana, Dana Liebowitz. We had some classes together."

Wow! Dana Liebowitz, I remember her now. She had big glasses and seemed to wear a lot of baggy sweaters back then, but was a sweetheart I'd had a bit of a crush on in Junior High. We talked a little but never more than that. When we all graduated she changed schools and I'd forgotten about her for the most part. Now I was seeing her again after four years, man had she changed, and in all the good ways too. She had gorgeous legs, a cute ass, and a chest that was held in by a good sports bra.

"Dana! Wow, it's been a long time!"

"It sure has! You look good." She said as she sat down beside me.

"Uh, so do you. What are you doing now? Or, what will you be doing?" I asked.

"Going off to college in the fall, NYU." She said.

"Man, that's big time." I said.

"Well, I love New York. I get to work for my Dad's office there too."

"What are you gonna study?"

"Corporate law, it's in my family. And I get to intern with his law firm while I'm in school. What about you?"

"I'm, uh, not sure. Gonna go to Community College, then figure out my next move after that."

"You were always a smart guy, Jim, you'll be good at whatever you do." She said as she put her hand on my knee and smiled.

"You know something I always wondered?" she started.

"What?"

"Well, we knew one another at King Street."

"Right."

"Kinda strange we never dated or anything, I always wondered why you never asked me out." She said.

"Oh, uh, not sure, maybe I was, uh..."

"Didn't think I'd say yes?" she said.

I looked at her and nodded.

"I would've, you know." She said.

"Well, it's good to know that and, uh..."

"I would've said yes to a lot of other things too, if you'd asked." She said.

"Oh, uh, really?"

"Sure, you always were kinda cute, you know." She said as she adjusted her sneaker laces. "So different from the other guys we went to school with."

"Well, thanks, nobody ever said that to me back then."

"You still are cute, you know." She said with a smile.

I was unsure what to do next.

"Hey, did you ever see the message board?" she said

"The what?"

"The message board, I always heard about it, it's supposed to be under the bleachers somewhere." She said.

"What is it?" I was very confused.

"Somebody did some kind of graffiti about people at school. I always heard about it but never looked, I was afraid I'd see something about me there. Doesn't matter much now, right?"

"But you didn't go here." I said.

"Yeah, but still, a name is a name. Come on, let's check it out."

She took my arm and we went underneath the vast bleachers.

I was very leery about this, a girl I hadn't seen in years is suddenly dragging me under the bleachers of our football stadium. Things like this don't happen to people like me. Dana guided me beneath the steel and wood frame, looking back and forth at different parts of it, like a detective.

"Oh my god, I think that's it!" she said excitedly.

The "message board" was on a thick piece of steel and was littered with different colored "messages" written in ballpoint pen, magic marker, spray paint, even scratched in with a knife. They boasted about people from the school, what they did, or wish they could do.

"Debbie gives great head!"

"Big dicks rule"

"Amy's a slut!"

"Wow this is so nasty!" she said with a giggle.

"Charming stuff" I said.

"Hey...look at this one." Dana pointed out.

It was in red marker, written very carefully, and with a heart for added effect.

"Hollywood Jim is hot!"

"I wonder who that could be?" she said with a sly smile.

"Beats me." I said with a shrug, trying to seem ambivalent. But I really wondered how my name wound up here. And how the "author" knew about the nickname name I'd been trying to live down.

"I wonder who wrote it?" she said with the same smile.

"Not me, that's for sure!" I said as I stared at this bit of fame we discovered.

"It was me." Dana said.

I turned to look at her, she was leaning on one of the beams, idly twirling her hair.

"You?" I said, surprised.

"Uh-huh."

"But you never went here. How could you even know about..."

"I heard things." She said with a smile, still twirling her hair.

Now I leaned back against a beam and we looked at one another.

Dana's hand drifted down to her shirt, and twirled a finger on it. I could see a nipple protruding from it.

"Jim...would you kiss me?" she asked.

"Kiss you?" I replied, now looking around to see if anyone was watching us.

"Come here..." she said.

I hesitantly moved over to her side and she smiled, then licked her lips seductively. I just stared in amazement. I slowly leaned in and kissed her. Her lips felt incredible. She smiled even more.

"Nice...I heard that too." She said softly.

"From who?" I asked.

"Like I said..." she kissed me again "I heard things."

Her arms wrapped around me now and we kissed deeper. Now with some tongue action thrown in.

I was still looking around to see if we were being watched. I think the football players had left. It had grown very quiet, we were definitely alone. Dana and I were now passionately kissing. My hand unconsciously crept down and felt her ass through the running shorts. She let out a small gasp as she knew where my hand was. She withdrew her lips from mine and leaned back against the beams.

We looked at each other, wondering what we should do next. Dana broke the ice by smiling and holding her hand to her mouth and giggling. I laughed too, we both knew what we'd done.

"Oh, my!" she said through her giggles.

"Yeah, oh my." I replied.

We embraced and kissed again, now I got up all my courage and made my move. I slid my hands down her thighs and caressed her ass, she didn't hesitate or brush me off. I now moved up to her tits and gingerly placed a hand on one, she cooed in response.

"Oh, that feels nice Jim..." she said softly. "Keep doing that..."

I now began to caress her tits through her shirt, her hands on my chest. She was looking at me all the while, staring into my eyes, as I was staring into hers. She began to breathe rapidly the more I touched her. Now her hands drifted down to my crotch. No surprise, I was getting harder by the second.

"Oh my gosh...this is so wild." She said.

"You're telling me." I replied.

We were both very hot and bothered at that moment. Dana looked around and led me a little further under the bleachers. She kissed me again, and as she did, I felt my shorts and underwear being pulled down.

"Dana...what are you doing?" I knew what she was doing, but it was all happening so fast.

"I want to give you a blowjob...what do you think?"

My dick was out in the open and Dana held it in her hand.

"Oh, you've got a nice one!" she said softly, but she was clearly excited.

Dana kneeled down and took me into her mouth, no preliminaries, just took it all in.

My head went back and I knew my eyes were widening at this new feeling, I was the one breathing rapidly now as she made my dick super-slick with her saliva and hand movements along its length. I started to look down and Dana's eyes were closed and I could hear smacking sounds from her mouth. She came off my dick, looked up at me and smiled.

"How am I doing?" she said with a giggle,

I could only close my eyes and nod slightly while smiling.

She smiled and resumed sucking me.

Her head bobbed up and down my dick and she licked my balls too.

She came off my dick again and licked her lips.

"Come on, let's finish what we started...I've waited so long for this." She said.

She pulled her shorts down and turned to show me her ass.

"Fuck me Jim..." she said as she bent over a steel beam and looked over her shoulder. Her ass and pussy looked incredible.

"Um...I'm not sure if I can do this." I stammered.

"Sure you can...I know you can." she said confidently.

I got up behind her and pushed my dick into her, oh she was tight!

She immediately gasped as I entered her.

"Keep going...I'm fine...do it..." she said quickly.

I started to fuck her, oh she felt good! I pushed in and out of her and she met my every thrust.

"Oh yeah...ohhh yess Jim....oh god so good...." She said in a sexy voice.

I reached around and felt her tits, she pulled her shirt and bra up and they felt super-soft in my hands, the nipples already erect.

"Oh yeah Dana...oh yeah...this feels so good." I said.

"You...you know it!" she replied.

I started to fuck her harder now and she began to moan.

"Oh yeah Jim...baby....oh yeah fuck meeeee!"

"I'm gonna cum Dana...gonna cum"

"Don't cum inside me...don't do it inside." She said forcefully.

I immediately pulled out and exploded onto her ass. She turned and was excited at the sight, laughing with excitement.

She turned to face me and we kissed again.

"That was great Jim, I wanted to do that for so long." She said lovingly.

"Wow...I'm...I can't talk now." I said.

She laughed as we pulled our clothes together.

"Let me give you my phone number, let's do what we should've done long ago." She said.

"Isn't that what we just did?" I said, to a girlish laugh from her.

"No, silly!" she said as she kissed me again "Let's go out together, at least before I go away to school. Then we can do this the right way."

"OK."

We walked back to where we started. She gave me her phone number and kissed me once more. Then she ran off, saying she had a meeting with her Dad's law firm.

This summer just keeps getting better!