Cool Fools 2: Loss and Gain
***Again, for those who want gratuitous, non-plot, straight up sex, this story isn't for you. But if you care to follow a storyline and learn about the characters, I think you will very well enjoy this series. And believe me, when the sex finally comes...it'll come in a way***
Woody Anderson had been struggling to push thoughts of his sister’s boyfriend out of his mind for months. When his closest friends revealed their gay tendencies, the eight-grader thought there must be a ‘gay virus’ going around, infecting their minds and polluting their thoughts. Woody could only think of one thing that would surely cure him: he asked Jessica Little, his current girlfriend, to have sex with him. Jessica told him that she was not ready for actual intercourse, but she was willing to give him a blow-up if he gave her one as well. Woody thought this was better than nothing and agreed. After the great experience, Jessica Little told her friends of Woody’s excellent use of tongue, and Woody found himself even more popular in school than before.
And just like that, Ethan White no longer disturbed his thoughts at night. All of his attention was focused at getting into Jessica Little’s pants. Woody was the stud of the school and thought it was awesome to have someone else play with his dick. He took it as a great challenge to make his girlfriend climax with the skills of his tongue, and he loved lapping up the sweet juices she offered him. Finally a week before the end of eight grade, Jessica let her guard down and opened herself up to him, making him her first lover. And after that amazing experience, Jessica Little recounted to her friends of how Woody had made her cum four times in one night, Woody became the biggest stud entering high school.
The summer was a time of transition for Woody and his sister. Woody was about to enter high school, and Laurie, the valedictorian, was moving to Yale. Woody learned from his sister (not that he was interested to know) that Ethan was staying in town to attend the state’s largest university and continue managing the shop.
One summer night, a week before she left for college, Laurie had called the house and Woody had answered the phone. She told him, “I’ll be home really late tonight. Try to distract mom and dad so they won’t notice I’m gone. And if they ask, say I went to a late night .” And so Woody did as his sister asked, and by ten o’clock, his parents asked where his sister was and Woody told them ‘at the movies’ and they went to bed.
Woody went to bed also, but did not go to sleep. He lied in bed flipping through a book of sexual positions, wondering if Jessica was willing to do doggy-style with him. He thought it was certainly one of the coolest sex positions ever invented. Even though his penis was growing hard at the thought of trying out different positions, Woody didn’t bother to play with his penis. He’d rather save it up so that when Jessica sucked him, he could fill her whole mouth, or when he fucked her, he could pull out and spray all over his silky slender body.
After flipping through the book front to back, Woody felt his eyelids drooping and went to sleep at midnight. All too soon, he woke up to the sound of rocks being thrown at his window. Woody stirred and looked at the time and noticed the clock was blinking 5 AM. Rolling out of bed, he pulled up the blinds and saw his sister waving on the front lawn below. As he opened the window, his sister began climbing the tree until she was level with the second floor and started moving out onto the large branch. Woody and his sister had sneaked in and out of the house before when they were younger, but his sister had grown so much compared to the old tree branch, Woody had to wonder aloud, “Can the branch take your weight?”
Laurie scolded, “I’m not that fat, you buttmunch!”
Finally she crawled through in the window, breathing out happily, as her feet landed firmly on the floor.
“You had sex with Ethan, didn’t you?” asked Woody. He could see his sister blushing. “Well, how was it?”
“No way,” scoffed Laurie, “I’m not telling you.”
“Oh, he must be terrible. I knew it.”
“NO! He’s not!” said Laurie crossly. And then her eyes fluttered dreamily, “He’s the greatest lover in the world. I mean, he’s gentle and caring and passionate in the beginning. But then…” Laurie blushed again as she had inadvertently told her brother too much.
“But then what? He poked around a few times, came and fell asleep on you.”
“NO! But then…he starts going rougher, and wilder, and harder and faster and I just lose myself with him…GOD, he is amazing!” Laurie cleared her throat and looked at her brother, “Anyways, I’m going to my room. Thanks for letting me in.”
“No!” Woody grabbed her arm, “I miss this…sharing secrets, sometimes a bit too much secret, with you…You’re leaving soon, and I want to talk to you before you go…”
And so brother and sister lie in bed together, reminiscing about their past, talking about their present, prospecting their future. Woody felt rather nice to be able to talk so casually with his sister. His sister always gave him great advice and reasoning about life. Years ago when questioned whether he should really hang out with the Welling twins because they were really bringing his ‘cool’ factor down, his sister had reasoned that by hanging out with them, he actually looked much cooler in front of them, and so he remained their friends. In fourth grade when he got in trouble at school for picking on a red-haired girl, he was grounded by his parents; but it was his sister who talked to him and saw straight through him: he picked on the girl to get her attention because he liked her. Laurie told him that girls can be very vengeful so he ought to go apologize or the girl would cut off his balls when she got the chance. And so he did. Yes, Woody had learned much about the dynamics of girls and guys from his sister, and he often shared this knowledge with his friends. Now that the two were older, their intimate talks became less frequent, but Woody secretly thanked his sister for making him as confident and as popular with the girls as he is now.
In September of his freshman year, Woody caught Jessica Little kissing a senior , Bruno Armstrong, the current star of the high school football team. Woody was definitely the jealous type, but he was too afraid to start a fight with the much burlier linebacker. Woody immediately broke up with Jessica and proceeded to ask out all her closest friends and managed to sleep with all of them by the second date.
One day Jessica had stopped him after school and asked him to take her back. “Bruno’s a good lover, but he’s just not as good as you, Woody,” was the explanation she gave him. So Woody fucked her in the back of her mother’s van, and afterwards, told her that things just wouldn’t work out between them. And after that, he expanded his prowl to all the freshman and sophomore girls. By the end of freshman year, Woody boasted twelve girls on thirty different occasions. Yes, Woody was building himself quite a reputation and he couldn’t wait til sophomore year to continue his legend.
The day after school ended for summer, Ethan White had come over to Woody’s house. His sister Laurie was coming back for the summer vacation, and Ethan wanted to go with the family to pick her up at the airport. Though Woody’s father and mother kept Ethan busy, asking about his first year of college, Woody still felt uncomfortable sitting next to the college boy in the SUV. The recalled the last time they were in a car together; Woody couldn’t stop thinking about the afterwards. The young man had managed to go a year without catching the ‘gay virus’, and he didn’t want to catch it again. When they reached the airport, Woody was first to get out of the car.
But as they waited for Laurie’s arrival, Ethan had plopped himself in a seat next to Woody and struck up a conversation with him, “How have you been this past year?”
Woody had no real reason to show Ethan any antagonism. So he answered politely, “Good. Everything’s going pretty steady. Freshman year’s actually a lot better than I thought.”
“I bet,” laughed Ethan, “Heard you’ve been very busy this year.”
Immediately this conversation had become uncomfortable; he had no desire to talk about his sexual promiscuity with the college student. Woody hoped and prayed his sister would appear soon, but half an hour past and Laurie still did not appear from the gate. An hour went by, and his mother read the monitor which informed that Laurie’s flight was delayed. Woody groaned to silently to himself, not sure how long he could stand talking to his sister’s boyfriend.
And then an hour later, people were huddled by the TV screens. Woody now found an excuse to leave his chair and went to find out what all the commotion was about. The news reporter on the TV had told of an airplane crashing in a cornfield in Missouri. The image of the burning plane glared on screen. There were no survivors, said the reporter. Woody’s mother gasped in horror and fell into his father’s arms when she realized the flight number of the crashed airplane matched Laurie’s flight.
“Maybe—she never went on the plane…” his father suggested. But the awful truth was the bodies were identified the next day, and a list was sent out to the media, and the name Laurie Anderson was in the list.
Woody couldn’t believe something like this could happen to his sister; how could God have let it happen? She was beautiful and smart and amazingly kind to everyone. She had such a bright future that could benefit the world…why did God stop her life so short? There was no reason for this; there were millions of bad guys God could have killed. He could gave gotten rids of murders and rapists and terrorists in this world, but instead, God took her. This was the most unjust divine plan of all!
At the funeral and services, Woody found himself sitting next to his sister’s boyfriend. He didn’t know why, but it felt so comfortable to be by his side. And after the services, Woody found himself sitting in his own room, still in the strong, gentle arms of Ethan White. They spent most of the time weeping on each other’s shoulders.
“Why?” Woody cried, “Tell me Ethan…why did God take her so soon?”
“Because,” Ethan dried his eyes and began, “You see, God had been observing Laurie down here for the past nineteen years. He saw her helping out everyone she knew; He saw the great spirit she had and how it can brightened anyone’s mood. So when she was on the airplane nearing the heavens, He sent her up there with Him. He wanted to make her an angel, standing beside Him, watching over the world. I think your sister would have been honored to serve the Lord.”
Woody only began crying more, “You know what I said to her last? I told her to leave me alone…” Woody choked, “We were talking on the phone and she was telling me to stop fooling around so much with the other girls. She said she was disappointed in me…and she said I should take you as an example, cause you’re still dating her even though she’s miles away….But then I told her to shut up and leave me alone. And I hung up on her.” Woody gasped in pain, “God, I was such a fucking asshole…”
“No, you’re not. Your sister knows you follow her advice even when you act out. She knows you’re a good kid, and she’s happy to have you as a brother,” said Ethan, “She’s told me so many positive things about you.”
“Like what?” Woody sniffled.
“Like how you cry in sad movies…yes, I think that’s a positive. Or how you’re always so helpful around the house. But the best thing, she says you make her hot cocoa when she’s sick. She loves you so much, you should know that…” said Ethan quietly, “And what do you like most about her that you’ve never mentioned to her before…”
“I don’t know, tons of things,” sighed Woody, “But I remember this one day after school in fifth grade. I was hanging out with Jimmy, Billy, and Reed on the playground. A gang of bullies came up to us and took Jimmy’s hat and pulled Billy off the monkey bars and chased around Reed. They didn’t bother me because they think I was cool, but of course, I wasn’t gonna let them hurt my friends, so I fought them. But then Laurie came. She was picking me up after school, and she went up to the bullies, and just with this look on her face and the way she was standing, she scared the bullies away. I was trying to sound macho and said that I could have fought them off myself, but I was really glad she came…And I never thanked her for it. I never thanked her for anything she ever did for me.”
“You should tell your parents. I’m sure they’ll love to hear those wonderful stories about her,” suggested Ethan, “In a way, that’ll be like thanking your sister.”
“Why are you like this?” Woody asked.
“Like this.” Woody said, waving his hand around the vicinity of Ethan’s body, “You’re so fucking nice. No other guy is like you. I mean, you’re a football star who likes comic-books…those two things just doesn’t go together. You were a senior jock who tutored freshmen after practice. You were only second to my sister as valedictorian. You’re good looking and athletic and have such an amazing personality, and you have every reason to gloat about yourself, but you’re so modest. I mean, are you for real?”
“I do consider myself a geek-jock. A cool fool, if you will,” Ethan feigned a smile, “But hey, you haven’t mentioned my perfect set of teeth worth fifteen-hundred dollars according to the dental bill.”
“See even when you’re bragging, it sounds like you’re making fun of yourself,” said Woody, staring at his pearly whites and soon realizing something was missing around it, “Whatever happened to your goatee?”
Ethan touched his lips, “Oh, got rid of it long ago. I only grew it for the King Arthur and the knights of the roundtable play that year.”
“Oh my god! You were the quarterback, president of student government, owner of a comic book store, and thespian in the drama club…how the hell did you find time for all that while dating my sister?”
“Well, she was a cheerleader, vice-president of student gov, frequent shopper at the mall, and avid fan of the drama club…So yeah, we saw each other a lot.” said Ethan and then his voice became more somber, “Listen, your sister really was worried about you hurting some girls’ feelings with what you’re doing, so she asked me to look after you. Now of course, I’m not gonna follow you around and control your whole life, but if you need my help or anything else, I’m more than happy to do so. Is that alright with you, Sherwood?”
The two young men hugged again, and for the first time since Woody could remember, he had no strong reaction against the usage of his proper name.
High school begins, secrets are revieled, and Sky has decisions to make...
- Locker Room
- Jack Off
- Teen Boy