I was watching She's All That the other day and realized that Laney's little brother, Simon, had a very unnatural fixation on Zach (Freddie Prince Jr.'s character). I figured that this would make a very good story with a little gay fantasy magic. Simon is played by Kieran Culkin, brother to Macauley Culkin, but apparently Kieran has had a much more promising movie career.
This may become a series; just depending on how much I like this installment and how much response I get from you faithful readers. This story has some potential given the presence of so many hot guys in the original movie, Paul Walker, Usher, Matthew Lillard, plus the entire freshman soccer team that came to clean the house...lol.
As a disclaimer, I do not know any of the above mentioned actors, nor do I own the rights to this movie or the rights to these characters. I do not know any of the sexual preferences of any of the actors in She's All That, nor do I care. This is intended solely for entertainment and fantasy. This is also intended for readers over the age of 18.
Now on with the show.
*************** He's All That.
refresher for those that haven't watched the movie in a while:
Zach: Freddie Prince Junior, prom date for Laney Simon: Laney's little teenage brother. Dean: Paul Walker's character that gets it in the ear with the air horn at the end. Ron James: Usher's dj character.
It was shortly after graduation that things really began to change for Zach.
His life had already been turned upside down with his college problem and with the addition of Laney to his life. He owed Laney a lot for getting him away from the scum that he used to date and hang out with. When he thinks back to the fact he used to fuck Taylor's very busy ass, he almost heaves. But even through all the changes of late, he still feels that something else is out there waiting on him to change.
It was around the first of June and Zach was pretty bummed. Laney had become his closest confidant, but she was away at an art internship in San Francisco. Mr. Boggs, Laney's father, had called him on Wednesday to see if Simon could stay with Zach for the next week. Mr. Boggs had a pool cleaner's convention in Las Vegas for a week and Simon couldn't stay with his aunt as planned because of some family emergency. Mr. Boggs really wanted to go as there was also a Jeopardy tryout in Vegas that weak and he thought he might have a shot.
Zach told Mr. Boggs that his parents had gone to Europe and wouldn't be back until August, but Mr. Boggs trusted Zach and didn't mind that he was alone. Zach really liked Simon. He thought Simon was a really sweet and smart kid, and he always loved hanging out with Simon. Zach agreed without any hesitation, as he knew that Simon could get him in a better mood without even trying.
Simon came over Sunday evening with his backpack over one shoulder and his duffel bag filled with clothes and underwear on the other. He was dressed in a pair of baggy workout shorts and a white t-shirt that seemed a tad to small. Simon gave his usual big smile as Zach answered the door and came right in.
"Zach attack...Waz UP!" Simon greeted.
"Not much Simon my man. Ready for a week of "no parent" fun?" Zach putting his hand on Simon's shoulder and guiding him up the stairs to his room.
"Yeah man. So cool...no parents...no school...no pool cleaning...rocks man...gonna do some SEGA!" Simon said all excited as they climbed the stairs.
"Your choice...you want your own bedroom, or you wanna bunk with me?" Zach asked standing in front of the door to his room.
"With you is cool." Simon asked looking up at Zach with an adoring smile.
Zach noticed the smile as he always does. He figures Simon has a case of hero worship, and he doesn't mind. The two file into Zach's room where he grabs Simon's stuff and piles it in a corner next to his desk.
"We'll make you a bed later. I think I have an air mattress you can sleep on. Why don't we go swimming and then order a pizza later. Sound good Simon?"
"Yeah, awesome." Simon answered.
"Cool, grab your swim suit and change." Zach replied walking over to his dresser to find his suit.
Simon dug in his back and pulled out a Hawaiian themed suit complete with palm trees. Zach found his own trucks finally and turned to find the bathroom when he realized that Simon was taking off his clothes in the middle of his room. Zach just watched for a moment as Simon revealed his tan smooth little body, conditioned from cleaning all those pools with his dad. Zach stood in silence as Simon removed his shorts leaving him in just his tighty whities. Zach didn't want to freak Simon out or making him feel uncomfortable so he just started changing too. Zach knew that Simon was pretty sensitive, especially about doing stuff wrong around Zach.
Zach pulled off his own shirt as Simon's underwear fell to his feet giving Zach a pretty good view of Simon's 14 yo dick surrounded by just a few wisps of hair. Zach gulped and dropped his own shorts and underwear, quickly replacing them with his swim suit.
Simon looked over at Zach during that quick change, trying to catch a glimpse of Zach's naked body. Simon intentionally started changing in front of Zach in hopes that Zach would follow suit. He saw Zach eye him when he dropped his own underwear, and Simon caught just a quick glimpse of Zach's flaccid cock before it was covered with a swim suit.
The two ran down the stairs and out into the back yard, both jumping into the pool at the same time. The two began to splash and frolic like any two guys would do in a pool. The swim races, dunking contests, and general horseplay went on for about an hour before Zach finally got out to go order a pizza.
Later that evening after Zach and Simon had devoured an entire large pizza, the two sat on the couch in the family room watching a movie. The two had changed into shorts and laid on opposite sides of the couch engrossed in the Terminator 2. It was about 11 when Zach looked down at Simon and realized that he was fast asleep.
Zach went up stairs and put a sleeping bag and a blanket on the floor next to his own bed for Simon. He then went back downstairs, picked Simon up in his arms, and carried him upstairs trying not to wake him. Zach laid Simon down, covering him up with a blanket before stripping down to his underwear and crawling into his own bed. Zach looked down at Simon sleeping, smiled, and then drifted off to sleep himself. *******
Simon woke up about 1am according to Zach's alarm clock on the desk. It took him a moment to realize where he was, and then he realized just how uncomfortable his makeshift bed was. Simon could hear Zach slowly breathing as he slept. Zach had a full sized bed, so Simon didn't figure Zach would mind if he slid into bed with him.
Zach was lying on his back with his arms under the pillows behind his head. Simon climbed up into bed gently trying not to disturb Zach. Simon laid down next to Zach, momentarily feeling Zach's smooth warm skin against his own. Simon couldn't bear to move so he just laid there feeling Zach's side against his own smooth chest. Simon laid his head down on the pillow with his face just an inch or two from Zach's pit. He sniffed quietly, inhaling the manliness.
Simon became very bold, taking his hand and laying it on top of one of Zach's pecs, feeling his chest rise and fall. Simon could feel Zach's heart beat as well. Simon's hand then slowly guided down over Zach's silky skin until his hand was resting on Zach's stomach. He could feel the small soft hairs of Zach's treasure trail. The sheet covered Zach's lower body, but Simon couldn't stop now.
Simon pealed the sheet back over Zach's crotch, keeping his legs covered so he wouldn't get cold and wake up. He looked down at Zach's beautiful crotch clad in a pair of very sexy Calvin Klein bikini briefs. He could see the mound in the front of Zach's underwear that hid what he had tried to see early that evening.
Simon's hand gently found Zach's mound and slightly gripped it. He could feel the intense heat and even the slight twitching of a dick coming awake. Simon then used one hand to raise the elastic band and the other to slowly reach in and touch Zach's growing dick.
It was at about this time that Zach slowly woke up, quickly realizing what was happening. He laid motionless, curious at what was happening, pretty sure he should stop Simon, but deep down not really wanting to. He laid there, as Simon wrapped his young hand around his now half hard cock and rub it. It was everything he could do not to moan as Simon slowly massaged his cock. In just a few seconds, Zach's 7 inches was fully hard with the head sticking out from his underwear. Zach just gritted his teeth trying not to moan as Simon surprised him again by lowering his head and licking the head of Zach's cock. Simon licked a few times before sucking the entire head into his mouth. It was at this point that Zach lost control and gasped and jerked letting Simon know that he was awake.
Simon froze as Zach gasped and jerked shoving half of his cock into Simon's mouth. Simon slowly withdrew hoping that Zach was still asleep. He looked up to see a gasping emotionless Zach looking down at him. They both froze as their eyes met, each looking at each other for some sign.
"Go ahead Simon, it's ok." Zach said giving Simon an unsure little smile.
Simon stared for a few more moments making sure he hadn't just dreamed that, and then he turned back sucking Zach's cock back into his mouth. Zach gasped again as Simon began sucking on Zach like he had always dreamed about. Simon consciously tasted Zach's cock, trying to see if it tasted like he thought it might. It was so masculine and salty, and for Simon it tasted even better than he imagined.
"Ahh Simon...fuck...so good baby...so good." Zach mumbled almost incoherently as he ran his fingers through Simon's silky hair.
Simon smiled around Zach's cock as he heard Zach call him "baby."
"Oh god Simon...where did you learn to do this?...oh fuck."
Simon pulled off of Zach's throbbing cock letting his hand slowly jack the hard drooling cock. Simon leaned down and let his tongue swipe off the bead of precum that had become to form on Zach's cock. Zach put his arms under Simon and pulled the teen up to him where he began to kiss the boy.
Simon and Zach kissed passionately, their tongues invading each others' mouths. Zach's hands began to roam all over Simon's tight young body, removing clothing as he went. Finally Simon was completely naked lying next to Zach's own naked body. Their skin tones were almost the same in the areas where they tanned as they both spent a great deal of time outside, but in the areas where clothes kept him from tanning, Simon, was a beautiful white. Zach loved the feel of Simon's smooth skin, especially the firmness of his young ass.
Simon's hands were also busy feeling up Zach, and continuing to massage his cock. Zach pushed Simon onto his back as they continued to kiss, then broke this kiss as he hovered above the young teen. He looked down at Simon's beautiful body, and couldn't believe how turned on and excited he was. Simon looked up at the jock god that he had worshiped forever, the man that had saved him so many times, the man he knew he loved.
"You ok with this Simon. If you're not, it's cool...really...it's cool." Zach asked with pleading eyes searching for any discomfort in Simon, the teen that he used to love as a brother, and now was beginning to love in a different way.
"I'm ok Zach...I'm in heaven...I've dreamed about you and this."
"Ok Sega boy...wanna know a secret?" Zach asked causing Simon to nod. "I've thought about this too." Zach answered.
Zach leaned down kissing Simon passionately, then working his soft lips up to Simon's ears, down his throat, over his chest and nipples, down his soft stomach, skipping the boy's very hard cock, and then down the boy's thighs. The attention Simon was getting from Zach's soft kisses was sending shivers up and down the teen. Finally Simon felt Zach's lips begin gently kissing his almost hairless balls. The kisses turned to licks, that lead up to his cock.
Simon almost had a heart attack as Zach grabbed his teen dick and guided it into his mouth. No one had ever done anything like this to Simon, and he was glad that Zach was his first.
"Ahh Zach...yeah...pleasssee..." Simon moaned tossing his head back and forth.
Zach began to give the best blow job he could think of. He concentrated on his own experiences in receiving them, and tried to make what he figured was Simon's first bj the best ever. Zach had Simon's entire 6 inches in his mouth while his free hand caressed the teen's balls. Zach then withdrew giving Simon's cock some long ice cream cone licks. Simon took this opportunity to raise his legs back exposing his hairless ass and pink pucker to Zach. It took Zach a moment to figure out why Simon did what he did, but confusion was soon overcome by lust and Zach dived into Simon's ass, burying his tongue and face into the teen.
"Oh yeah Zach, I can't believe we're doing this." Simon moaned.
Zach pushed Simon's legs back even further giving him ultimate access to Simon's most intimate areas. The musky sweaty taste of Simon's ass was driving Zach wild. Zach was overcome with desire as he sat up leaning into Simon and then leaning down to kiss the teen boy in his charge. The two kissed wildly again as Zach's very hard cock pressed against Simon's hole, Simon's legs over Zach's shoulders.
"I'm not afraid Zach, go ahead...do it...please...I want it." Simon said, with Zach instantly knowing what Simon meant.
"Ok baby." Zach answered.
Zach reached down holding his cock straight and aiming at Simon's small pink hole.
"Zach?" Simon timidly said
"Yeah?" Zach breathlessly answered.
"Umm...lube?" Simon said with a small smile.
"OH fuck...yeah...just a sec." Zach said with a little laugh.
Zach leaned over to his nightstand retrieving some KY jelly that he kept for jacking off. He squeezed out a small drop and rubbed it into Simon's ass, causing the young boy to moan. Zach took a bit more and greased up his cock before sitting the tube next to them. Zach put his cock back at Simon's hole, feeling the warmth of his ass against the very tip of his dick. Zach looked down at Simon who looked back at him with a smile and an adoring face. Zach smiled and pushed slightly into Simon.
Simon's face took on a look of pain as Zach's head slipped inside of Simon's young ass. He soon recovered and looked back up at a worried Zach.
"I'm ok." Simon reassured.
Zach began pushing a little more slowly sliding his 7 inches into Simon's body. Simon grunted a few times, but never had to push back on Zach or stop him. Zach finally was fully embedded inside Simon, his girlfriend's little brother for Christ's sake. Simon let out a deep guttural moan as Zach bottomed out, letting him know that Simon was feeling just fine.
Zach began slowly pumping in and out of Simon, as the young boy moaned and mumbled incoherently. Simon was in the throws of ecstasy as he felt Zach's cock massage his ass and prostate. Zach looked down at his boy in so much pleasure, as his own body was overcome with a tingling sensation. Zach truly began to fuck Simon as his orgasm grew closer.
The two began to moan louder and louder. Even Simon began talking dirty. Zach was surprised at the dirty erotic things coming out of this 14 year old boy's mouth.
"Fuck me Zach. Fuck my tight teenage ass. Oh Zach, dude, your cock feels so good." Simon continued on and on.
"Oh fuck Simon...I'm gonna cum." Zach announced just before his load began emptying into Simon's ass.
Simon could feel the warmness of Zach's load filling him up, and he reached down to grab hold of his own cock to release his load. Zach heaved and gasped as he came down from his orgasm. He realized that Simon was very close to his own orgasm, so he quickly dropped to the bed removing Simon's hand and sucking Simon's cock into his mouth. Zach managed to get Simon's cock into his mouth just moments before Simon began shooting his load. Zach never thought about eating cum, but he couldn't resist the temptation of tasting Simon's innocent load. Zach loved the warm feeling of Simon's cum filling his mouth, and the taste wasn't as bad as he assumed it would be.
Simon was moaning and thrashing as his load filled Zach's mouth. His moans became even more pleading as Zach cleaned off his now very sensitive cock.
"That rocked Zach. So rocked dude." Simon cooed.
"Yes it did little man. I never even thought about this before, but it seemed so natural with you. I love you little dude." Zach confessed as he laid next to Simon, taking the young boy into his arms, their sweaty bodies sticking together.
"I love you too Zach. Thank you so much." Simon said laying his head on Zach's chest.
"Thank you Simon, for opening my eyes. Now let's get some sleep. We'll talk about this more tomorrow. ok?" Zach asked running his fingers slowly through Simon's hair.
"ok baby."
The two drifted off to sleep, tightly embraced.
******* Ok, so that's it for now until the next installment. I wanted this installment to be better, but I had to have some set up, some pre-fuck stuff for everything to make sense. I'm ready to bring on the next part where I can really get into to some hot and heavy stuff with these two characters plus some of the other's from the movie. If you liked it or at least think it has potential, please email me.