Hollywood Jim: The Early Years Pt. 01

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".

I was the epitome of the school geek. I had no luck with girls of any kind, and no talent in sports. And a nickname that often made people snicker when they realized who had it. Whatever girls I knew were simply friends. The really gorgeous ones I could only dream of. They were often in the arms of brain-dead jocks whom I was certain planned to only add them to their lists of conquests to brag about. Graduating from high school was somewhat bittersweet. I really wasn't sure what I wanted to do next. Luckily my parents gave me some time to think about my next move. Some kind of further education was better than none, so I enrolled in a local community college for the fall term, thinking it would give me an idea where I wanted to go next. The rest of the summer now beckoned me. Most of the girls I knew were off somewhere else, but to my surprise a few were still in town. Rose was one of them. She was a Latina tomboy who played soccer. She had short black hair, a cute face and personality. That's why it surprised me when I ran into her one day. I was always nervous whenever I met someone outside of school. I always feared some kind of humiliation was in store for me. But she was exactly the same as I remembered her. I worked up the courage to ask her out but she told me how she was frequently babysitting for this family across town so her nights were often spent there. I was disappointed, but she invited me to come over there anyway, just to hang out. OK, cool, I thought.

The house where she was babysitting was in a quiet upscale neighborhood off the main roads. I went over there one night and we goofed around with the kids until she sent them off to bed so we had the house to ourselves for the most part. We spent the better part of the evening watching TV and talking about everything imaginable. She was very flirtatious with me as we flipped through the channels looking for something to watch. She accidentally came upon the Playboy Channel. I was surprised, I'd only heard about this channel before. And now here it was, in all its unscrambled glory.

"Oh wow, look at that!" she said with an excited giggle.

"Okay, this is different!" I said with a laugh.

It was weird watching this channel and seeing gorgeous Playmates I'd previously seen only as still images. But Rose was watching intently, I was too, and trying not to act excited by all this.

"Did you know they had this channel?" I asked.

"Oh yeah, I watch by myself sometimes, it's kinda cool."

"Really?"

"Sure...wouldn't you if you could?" she asked with a smile.

"Well, I'm only a guy so I guess so." I said with a shrug and a smile.

We both laughed and continued watching the Playmate Review program. As we watched, Rose was sitting closer to me and I was wondering what I should do now. Was the fantasy on TV better than the reality sitting next to me?

"Do you think she's pretty?" Rose asked me.

We were watching Playmate Lynne Austin do a striptease for us now.

"Uh, yeah I guess so." I said.

"Oh come on, you think she's hot, don't you?"

"OK, yes she's hot, she's the object of every fantasy I might have." I said with dramatic flair, hoping that I could somehow humor my way out of an awkward situation.

"I think she's hot too." Rose said nonchalantly.

"Huh?" I replied.

"I think she's really pretty, I'd do her."

"What do you...mean?" I asked, wondering if I'd heard her right.

"I'd do her, I'd have sex with her. I think she's got a hot body. She's got great boobs."

"I'm not sure I'm hearing you right, do you mean that...?" I slowly asked.

"I like girls too." She replied. "I like guys first, but girls are, um, nice too."

"Whoa! Wait a minute! I can't believe what you're saying!" I was stunned. I'd known her throughout school but never really thought of her as anything but an athletic girl who was a friend. Now I find that this girl is actually "playing for both teams" as it were.

"You're the first person I've told this too, outside of girls I know already."

"So you've um, you've..." I asked hesitantly.

"Fucked girls? Sure, it's nice." She said with a smile. "Is that what you wanted to hear?"

I didn't know what to say.

"Yeah, I've done it with a girl on the team. And I won't tell you who." She quickly added.

"I'm not sure I want to know." I replied.

"Sure you do, it was Kelly MacLeish." She replied.

"Kelly! Oh my god!" I said stunned, I'd known her since elementary school. And in the years since, she'd developed into an athletic bombshell who could easily be a Playmate herself.

"I knew you'd say that. She's got a hot body too." Rose said with a laugh.

"Man..." I was too stunned by all these revelations I was hearing.

"I've never seen you like this." Rose said with a smile. "What do you think of all this true confessions stuff?"

"I don't know what to think."

"I think you're turned on, that's what I think!" she said laughing.

"Oh is that so? So...what am I thinking now?" I said sarcastically.

"I think you'd like to do me." She said looking at me "that's what I think."

I just looked at her, she was smiling.

"Um, pretty bold thinking."

"Yes...pretty bold." She said.

We stared at each other for what seemed an eternity before we slowly leaned in and kissed. She giggled as we kissed again, then a third time, more passionately.

"That felt nice." She said "Did any one tell you how good a kisser you are?"

"No, nobody has." I said nervously.

"Well, you are."

"Thank you." I said, feeling bolder, as I kissed her again.

We continued kissing more and more and my arms wrapped themselves around her, gradually dropping lower to her waistline. She then withdrew and smiled at me.

"Let's get a drink." She said.

"Good idea." I said.

Rose led me into a spacious kitchen with features fit for a gourmet cook. The fridge had an assortment of drinks and she gave me a bottle of fruit juice. She was smiling very mischievously as we stood there sipping our drinks. I could tell she had lots on her mind with me there. She gently embraced me as I stood against the counters and we kissed. She rubbed her crotch against mine and she could tell I was reacting to her kisses and contact.

"Mmmm...I can tell you're excited." She said.

"Uh...yes." I said, still nervous.

"I like this..." she said as she continued to grind her hips into mine.

She looked at me and nodded slightly, then began to unzip my jeans.

"Uh Rose...are you sure this is okay?" I said.

"Sure it is...I've wanted to do this for a long time with you." She said as her hand went inside and felt for my hardening dick. "And now is the best time."

She found it and started to pull it out from my pants. When she freed it, she gave a little gasp.

"Oh! It's so pretty." She said softly.

"Rose are you sure this is.." I said hesitatingly.

Rose looked at me and calmly said

"Don't worry! The kids are asleep, their parents won't be home 'til much later."

As she began to caress my dick, she looked into my eyes and smiled. She released her hold on me and began to unbutton her polo shirt and slipped it up and over her head. She had on a lacy white bra that held her nice B-cup breasts. She unsnapped her pants and slid them down, showing off panties that were a pretty pink with lace accents.

"Take your shirt off Jim." She said.

I took off my t-shirt and she removed my jeans, sliding my underwear off. I was naked in front of her, and feeling incredibly nervous. Rose giggled a little, then unsnapped her bra. Her skin was a beautiful dark brown, like coffee. Her nipples were small and penny sized. She wasn't nervous at all, she embraced me and we kissed again, her tits felt so nice pressed against my chest as we kissed. She took my rock hard dick and rubbed it against the front of her panties. I felt a warm, moist feeling on the tip. She was excited, I could clearly tell.

"Take my panties off, Jim." She whispered in my ear.

My hands were shaking as I felt her hips, then the waistband of her panties. My thumbs gripped the sides and I began to slide them down. Rose was breathing heavy in my ear. The panties slid downward until I felt them drop from my hands and gently touch my toes.

Rose and I were now completely naked.

She took a step back and smiled while she looked at me, this guy she'd known as a friend but now clearly desired as a lover. She had a great body. All that soccer had done wonders for her. Her tits were round with little nipples and her belly was almost perfectly flat. Her pussy was just slightly trimmed with jet black hair.

"Wow, you look...fabulous." She finally said.

"You look...great." I replied.

"Think so?" she said as she turned around and showed me a cute little ass.

"Like my booty?" she said with a giggle.

"N...N...Nice." I said, gradually warming up to this feeling of being naked with her.

"Kelly's is nicer." She said.

Rose came over to me and held my dick.

"But you've got something even nicer." She said with a sly smile.

Rose knelt down and looked even closer at my dick.

"Very nice...very hard...very pretty." She said looking up at me as it went into her mouth.

I gasped somewhat as I felt her wet lips and tongue on my dick. I was trying to concentrate on this wonderful feeling but was still amazed at how things had transpired, and who they were transpiring with. I looked down and saw Rose's black hair as it slid up and down my dick. I tried to lose myself in this wonderful feeling, but I kept looking around thinking that someone was going to show up at any minute. Rose didn't seem to worry, she was lost in me. I was breathing heavily as her lips and tongue slid the length of my dick. I finally worked up the courage to distract her. I placed my hands on her cheeks and she looked up at me.

"Maybe we should do this somewhere better." I said.

"OK, I know a place." She said.

She gathered up our clothes and led me to a door that went downstairs to a game room that had a pool table, pinball machine and jukebox. A leather sectional couch was in a corner facing a big screen TV. Rose tossed our clothes on the floor and jumped on the couch, beckoning me with her finger and a mischievous smile. I nervously joined her on the couch and we embraced. My hands were shaking as they moved over her body. She smiled at me, then held my face in her hands and softly kissed me.

"It's OK Jim, you're fine." She said.

"I'm just so...so...nervous. I'm sorry." I stammered.

"Don't be...you're gonna be fine. Kiss me." She said softly.

We kissed softly, then with more feeling. Her hands were sliding all over my body and I could feel her caress my ass in particular.

"Oh, that feels nice." She said.

My hand gingerly reached down and felt her breast. She smiled at this feeling of my hands finally on her.

"Ohhhh....yes, Jim. Please...touch me." She said softly

I began to caress her nipples as I kissed her.

She was breathing heavily as I did this. Then she softly took my still shaky hand in hers.

"Jim...touch me down there." She said as she guided it down to her crotch and a clearly wet pussy. My fingers easily slid inside her. And she gasped as I penetrated her. I was breathing heavily now too. She felt so good and wet, my fingers were quickly enveloped by the wetness of her pussy. I kept sliding my fingers around inside her.

"Oh god Jim...baby...oh my god that's it..." she said in between moans.

I softly kissed her cheek and lips.

She responded by deeply kissing me with lots of tongue.

"Jim...I want you...I want you to..." she started to say.

I could only look at her, I knew what she meant and she nodded.

"Please...let's do it." She said.

"Are you sure? I mean...are you, um..." I stammered

"Protected? Yes...oh yes I am." She said with a reassuring smile. "I knew you'd ask that. You always were someone who'd think of things like that."

"What do you mean?"

"You're a lot smarter than people think, why do you think they call you 'Hollywood'?" she said.

"I just thought it was a goofy name." I said.

"Oh no...not at all." She said as she kissed me "I always knew you were a smart guy...you're gonna be a big success in whatever you do, Jim. I know it. You're so much better than you think you are"

I was surprised at this revelation, but then again I'd just been told that a good friend had had quite a fun time with a girl of my fantasies.

"So, Mr. Hollywood...wanna fool around?" she said with a giggle.

"How can I resist?" I said.

"Think you can do it?" she said with a sly smile.

"Guess I'll find out won't I?" I said apprehensively.

"You'll be fine." Rose said with a confident, reassuring smile.

Rose slowly opened her legs wide and I could see her beautiful pussy beckoning me. I looked at her and she had a smile of anticipation on her face. I took a deep breath and got between her legs and nervously slid my dick into her. She was still smiling and her eyes slowly closed as she felt me enter her. It felt so warm inside her.

"Oh Jim....yesss that's it. Oh yes that's it!" she said passionately.

Every image from any porn film came to me and I began to push in and out of her slowly. Her pussy was so tight, but so hot. I looked down at her face and there was a look of lust as she held me.

"Oh god! Yes Jim...oh god you're so good!" she cried.

My steady pace was really turning her on as I thrust in and out of her. Now I was getting turned on as I fucked her.

"Oh yeah Rosie...oh this is so good..." I said.

"I told you! Oh yeah you know what to do baby! Muy bueno!" she said with a smile.

Wow! Now she was talking in Spanish to me!

"Jim...let's do another position." She said.

"OK"

I pulled out of her. My dick was, thankfully, still hard.

Rose turned around and showed her cute ass to me.

"Do me doggy Jim...all Spanish guys do this, you'll love it."

She seemed to have a lot more experience than I ever imagined

"Okay...I hope you're OK with this." I said, still a little nervous.

"Baby, I love this! It's just like I imagined." She said.

I caressed her chocolate brown ass. The contrast in skin colors was striking, but more likely it was because I hadn't spent much time in the sun.

No matter, I took my dick and rubbed it a little on her ass and then on her pussy lips. She moaned a little.

"Please Jim...put it in me."

"OK, yes."

I found her pink opening and pushed back inside her.

"Oh yes! Oh my god Jim! You feel so good! Do it! Do it!" she cried out.

I wasted no time and really started to fuck her, now I felt like I was "the man" as it were. I grabbed her hips and brought them against me with every thrust. Man did she feel good!

"Oh yeah Jim, fuck me! Fuck me! Oh god...fuck me!"

My balls were slapping up against her pussy and I was breathing heavily all the while. Rose let out a long cry suddenly.

"Are you OK?"

"Oh yeah...I just came...keep fucking me Jim...keep fucking me...I want you to come!"

She didn't have to say that twice. I kept pounding into her pussy, eager to have that same feeling she did. I didn't have to wait long.

"Oh I'm gonna cum...oh yeah...gonna cum!"

"Oh cum inside me! Cum inside me, Jim!" Rose cried.

And I exploded amidst a shriek of joy from Rosie. I held her hips close to me and she sat up and wrapped an arm around me as we kissed. Then we slowly collapsed onto the couch. Still wrapped in one another.

"Wow! That was wild! You're something Jim...just like I imagined." She said softly.

"I never thought it could feel this good." I said.

"You're gonna feel even better." She said with a sly smile and kiss.

"I am?"

"Uh-huh." She looked at her watch. "It's getting late, the kids parents will be home soon. You better get going."

"Oh, Right."

Rose and I began to quickly dress.

"Hey, kiss me Mister Hollywood." She said with a giggle

I smiled and kissed her.

"Uh, what did you mean when you said I was gonna feel better?" I asked.

Rose smiled.

"You'll see very soon. The more we do this the better it gets."

I was still confused.

She showed me out of the house and into the cool night air, the neighborhood was silent, like a "mute" button had been pushed on all sounds.

Rose gave me another kiss goodbye.

"I'll call you next time I'm here." She said.

"Okay, I'll see you soon." I replied.

"You sure will!" she said with a smile as I headed home.