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.
