By Charlie Flemming
Main Characters
Jack-18, 16" cock, light brown hair, blue eyes, 6'3" tall
Sara-Mom-36, GG-sized tits, black hair, brown eyes, fit but very tone and curvy.
Rita-Aunt-37, FF-sized tits, blonde hair, blue eyes, similarly amazing body to Sara but not quite as hot
Josephine (Jo)-sister, 18, EE-sized tits, twin to Jack, red hair, green eyes most popular girl in school
Clara-Cousin, 18, EE-sized tits, brown hair, kinda dumb but very kind
Beth Ryder-teacher, 28, FF-sized tits, redhead
Naomi Moore-38, doctor, FF-sized tits, African American
Rose (Ro)-18, DD-sized tits, Jo's best friend and a popular girl in school, brunette hair
Wednesday, September 14
1
Sara had another dream. This time she was at the doctor's office again while her son's cock was out. Naomi was stroking her son but it wasn't working.
"I'm sorry, Sara," Naomi moaned as she jerked Jack off like there was no tomorrow, "He can't cum! I think there's only one way to get your son to orgasm!"
"What's that?" Sara moaned, she was in the bathing suit she wore when she was teasing her son in the dining room the other day. She had both her hands under the top and was playing with her massive boobs. She could feel herself working up to a massive orgasm just from playing with her tits. "I'll do anything to help my son!" Sara said, her voice leaking sexuality.
"Anything?" Naomi asked and then lightly licked the tip of her son's cock to swallow some of the copious amounts of pre-cum leaking from it.
"YES!" Sara moaned as she came, "I'LL DO ANYTHING YOU ASK!"
"Good, because the only way he's going to cum is if you fuck him. He needs to fuck his mother's pussy. It's the only way to cure this specific condition." The doctor explained, jerking Jack's cock so fast Sara was worried she was going to rip it off.
Sara moaned again but quickly pushed her bikini bottoms out of the way as she straddled her son on the operating table. Soon, she was cumming like crazy on his massive cock as she fucked him like crazy.
When Sara woke up in her bed, this time it was after she had orgasmed. In fact, the bed was so wet this time that she was certain that she came multiple times during the night.
She quickly cleaned up the bed and had to change the sheets once again. After she had the laundry going, she took a shower. As the water cascaded down her beautiful body, Sara thought about what had been happening between her and her son.
Sara felt this was going to keep happening every day, changing her sheets after her nightly wet dreams, but wasn't at all sure what to do about it. I need to stop having these sexual thoughts about my son. Sara pondered. How though? It's not like I can make him suddenly have a smaller penis... She sighed as she fantasized about it some more, He's got such a big dick... God! I really wish he wasn't my son! She shut the water off in frustration and got out to towel herself off, Maybe I should talk to Rita about it? No! Just no. I don't think she'd be a positive influence on the situation. She remembered how last time it escalated until Rita was giving him a handjob, something Sara did not want to happen again, I guess the best course would be to talk to Jack about it instead. I mean, after our movie watching yesterday things have felt a bit more normal between us. At least since I saw his penis last week... He gets to go back to school today maybe I'll wake him and we can...talk.
Sara gulped nervously as she realized that something about this idea was making her very horny. She knew she had to keep it under control. She grabbed her robe, a normal white one that showed off her cleavage and hung down to her knees, and then walked across the hall into her son's room.
2
Inside, Jack was still sleeping. Sara felt her breath catch in her throat as she saw him. He's so handsome, she thought as she stood in his doorway and admired her son's sleeping form, I just want to curl up next to him in bed... She halfway considered it but realized that she should just wake him up.
"Huh? What?" Jack yawned as he opened his eyes. He saw that it was his mother, looking sexy as ever with her damp black hair and soft robe. It was just a normal robe but it still looked hot on his mother's voluptuous body. He tried not to ogle her breasts with Sara's deep cleavage on display but it was too late. His boner made a very obvious tent in the blanket he was lying under.
Sara noticed this, "Oh wow, I mean, is that because of me?" She asked before she considered her words more carefully.
Jack blushed but nodded without thinking about it. His sexy mother sitting on the bed next to him was clouding his brain. "I mean-" He said but it was already too late.
"It's okay, really," Sara said with a smile as she stared at the huge tent that was right next to her. "I know you have a problem." Still thinking more about her latest sex dream than anything else, she took a hand and poked the tip of her son's dick through the covers and said, "Poke."
She gasped at herself, not believing she had just done that. Sara wanted to run out of the room but she looked at her son in his eyes instead to gauge his reaction to what she had just done.
Jack blinked at her because he couldn't believe it either. Part of him wanted to do... something. But his sexual inexperience was biting him in the ass once again as he wasn't exactly sure what he wanted to do to his own mother. "Um, did you want to talk to me about something?" He asked after a moment of silence, not wanting to address that his mother just, kind of, touched his penis.
Sara decided to just ignore what just happened as well, "Um, well, I, um," She muttered nervously as she tried to find the right words to say to her son that she felt like she was always moments away from rushing up to him and fucking his brains out. She lost the confidence to brooch the subject and decided to just lie, "I only came in here to make sure you were up for school. You've been sleeping in a lot lately and I don't want to miss any now that you get to go back."
"Oh, okay. Thanks, Mom." Jack said as he lay his head back down on his pillow, "I actually could use maybe five more minutes." He said as he closed his eyes.
Sara bit her lip as she glanced at the obscene tent that Jack's gigantic cock was making in his blanket one more time. She really really wanted to rip the blanket off of him just so she could see it again but knew that really wouldn't help her taboo lust for him.
Sara sighed and got up and left the room without saying anything else to him. She didn't come back to wake Jack up five minutes later either. Instead, she just went to the living room and did her morning yoga.
Soon after Jo and Clara joined her like they usually did in the morning. Jack eventually came down and went for a jog like he usually did as well.
3
After Sara dropped Jack and the girls off at school. Jack showed the doctor's excuse that Naomi wrote to the principal.
He read it out loud, "Sorry about the inconvenience with Jack and his...penis." The principal adjusted his reading glasses as he continued, "Jack has a medical condition that makes his penis and testicles amazingly large and near-constant erections is, unfortunately, to be expected. He also can't...um, reach orgasm, ahem, on his own. It is a consequence of this that Jack will have erections throughout most of his classes. Unfortunate incidents like the one in his history class will probably happen to Jack all the time throughout his life."
The principal thought the wording was a little weird but he accepted Jack back into the school and told him, "Despite what this note says, I trust there won't be any more incidents like this while you're at this school."
Jack assured him there wouldn't be. Then he went to his first-period class. Beth Ryder, the history teacher, was so surprised to see him that she rushed up and gave him a hug, "Oh thank God you're back. And thank you so much for taking the blame for that and letting me keep my job." She whispered to him as they hugged.
Beth's big breasts were pressed into Jack's chest for quite a while and it was having an effect on him. He tried to break the hug but she wouldn't let go and soon he had a giant erection pressed against his teacher's body.
Beth pretended not to notice, but truthfully, since she accidentally pulled Jack's dick out in the middle of class over a week ago, it's all she's been able to think about. She didn't plan on doing more than what she was doing right then, just to feel that huge hunk of meat pressed up against her body for just a moment. It felt heavenly to her, just such a big manly cock... Beth only wished that Jack wasn't her student...
She broke the hug and Jack quickly took a seat before anyone noticed his erection.
After school, his mother was avoiding him again. Jack wasn't even sure why.
When Jack went to bed that night, he felt like he had been erect most of the day. He hated that he couldn't jerk off and cum when he wanted to like he assumed every other guy his age could. Still, there was nothing he could do about it now. It just seemed like he was going to have to suffer until he got a girlfriend. And he felt like such a loser, he knew that probably wouldn't happen until he was out of high school next year. It was going to be a very frustrating year, he decided.
Thursday, September 15
1
Another day, another sex dream staring her son.
As Sara changed her sheets this time, her sister Rita was still there, it was earlier than Sara normally got up.
"Oh hey sis," Rita said to Sara as she came into the living room after putting her laundry in where Rita was watching the morning news on mute, so as not to wake anyone, like she did almost every morning, "You're up early."
Sara obviously couldn't admit she'd been having sex dreams about her son, "Um, just trouble getting to sleep," is what she said instead.
"I'm sorry," Rita said compassionately, "Is something troubling you?"
Sara sighed and sat next to her sister on the sofa, "Yes but I don't think I can talk about it. Not right now anyway." She really didn't want Rita to know, but felt like maybe in a few years when her son had moved away, then, and only then, could she talk about it. At least that's how she felt at that moment.
Rita looked thoughtful and decided to take a stab in the dark, "If this is about the doctor's appointment yesterday-"
"What?!" Sara said surprised, "How did you know?! Did you talk to Naomi?!"
Rita smirked, "No, I haven't had time yet, but I think you just admitted that something did happen." Rita put a hand on her sister's shoulder comfortingly, "You know you can talk to me about anything, right?"
Sara opened her mouth but closed it again. "I don't know..." She admitted.
"Well, if you don't tell me I can probably get Naomi to tell me." She said, though truthfully Naomi probably wouldn't because of "doctor-patient confidentiality." Naomi might be a nymphomaniac but that didn't mean she wasn't also professional and considerate most of the time.
Sara sighed. She really wished she had someone else to talk to about it, only because she was worried that Rita might take things too far again, but she also knew that Rita wouldn't blab what she was about to tell her to other people either. "Okay, I'll tell you. But please don't tell Jack, or anyone else for that matter, that I told you."
"I promise," Rita said, and she meant it. Her sister could trust her...usually.
But Sara didn't know how to admit to her sister that she'd been having very sexual feeling for her only son, so she just said, "I've just been a bit...frustrated is all."
"I could let you borrow my dildo if you want," Rita said. Then she laughed at Sara's embarrassed reaction, "don't tell me you still don't masturbate."
Sara blushed. That was answer enough for Rita.
"Well, I think that might be your problem right there." Rita said, "I'm sure if you get a few orgasms out of your system, you'll stop being so pent up."
Sara blinked, but she decided she still didn't want to tell Rita about her wet dreams, "Um, I don't think lack of orgasms is the issue."
"Well, you won't know until you try." Rita commented as she checked her watch, "Well, I got to get to work. We'll talk about this later though. Maybe after work?"
Rita ended up working late and leaving early the next day so Sara didn't see her again for a bit. Sara avoided her son outside of taking him to school and picking him up again.
For Jack, life seemed to go back to what he considered normal. His sister and cousin were gone all the time. Rita was usually working. His Mom just ignored him. His boring life was back to its most boringest.
Friday, September 16
1
This time, Jo was the one who woke up in the middle of the night. She had been dreaming about her brother. Most specifically about when she walked in on him with an erection alone with their cousin Clara in his room.
When she woke up she thought about that memory. There's just no way, she thought, my brother with a cock like that? The guy is more virginal than, well, most virgins! He doesn't know a thing, not a thing! When it comes to anything sexual. He's...just... a loser! There's no way he has a cock that size, there's just no way...
Jo knew she must have been imagining it, twice now, and she got up out of bed to go prove to herself, once and for all, that Jack's cock was just as average as most of her boyfriends'.
She snuck down the hall. Jo heard the shower on as she passed the bathroom and she knew that her aunt was getting ready for work, and she would have to be quick.
She snuck up to her brother's bedroom door. It was closed but she knew he never locked it. She slowly turned the knob and walked in. She closed the door behind her and it was too dark to see anything now. Jo was worried about waking her brother now but didn't know what else to do. She turned on his light.
Jack was lying on his back, snoring soundly. Jo wondered if he slept naked. She tiptoed to the side of his bed and grabbed the side of his covers. She lifted and gasped.
Jack did sleep naked. And his limp cock was right there for her to see. It lay along his leg and Jo could clearly see that it stretch almost down to his knee. His cock was completed by a bulbous cockhead that was almost as big as her fist. Jo was spellbound by it, and she couldn't help herself. She reached out at grabbed that meaty cock.
It was heavy. Jo lifted her brother's cock a few times and dropped it on his leg so it made a mighty SLAP every time. She was getting turned on as she played with Jack's penis, and as she touched it, she felt it getting hard. Soon, one of the biggest cocks in the whole world was standing rigid at attention in her hand and something changed inside Jo. Something major...
She started to stroke Jack's cock with one hand. Then two when she realized there was no way she could grip it all the way around with just one of her hands. She loved her brother's cock. It was so thick, veiny, and meaty, she knew that her pussy would be split in two in the most wonderful way if she ever fucked it.
Jack let out a loud snore and before the sound of it was over, Jo had gone from his room, turning the light off behind her, and was back in her room with her door locked and on her bed in the dark.
She ripped her clothes off and threw them on the ground. Something's different, Jo thought as she pet her pussy while images of her brother's dick filtered through her brain, I'm not sure what it is but something feels very different...like I have a purpose, or something...I don't know. She stopped thinking about it as her fantasy of fucking her brother started to get going. Within ten minutes she was cumming harder than she'd ever cum on any of her boyfriend's cocks while thinking about fucking her brother. After that, she fell asleep naked without even her blanket over her.
2
Jo didn't know what had changed then and wouldn't until near the end of the day. She was out on a date with one of her boyfriends. They were at the movie and making out in the back of the theater like they typically did. But Jo really wasn't into it and eventually stopped it.
"What? What is it Baby?" That guy said, an obvious, average-sized boner in his pants.
"I think..." Jo said not sure but then knew, "I think I don't want to see you anymore."
Jo got up and walked away before he could complain. As she was leaving she vaguely heard him complain "...blue balls..." But she honestly didn't care what the dumbass had to say anymore.
She came home late to her house. Too late to talk to Clara or call Rose. Too late to talk to her brother either, though she considered waking him up. She knew what was different about herself now. Jo had been in denial about her brother before. She thought that just because he was a loser and unpopular that meant he didn't have anything to offer, well, anyone really. Especially not Jo herself. But Jo realized as she touched his hard dick that morning that he wasn't a loser, he was special. A diamond in the rough, as they say in old Disney movies.
She knew he was a virgin, and, like she had thought that morning, probably didn't even know the first thing about kissing let alone sex. But his cock was something special, and that meant that so was Jack. Her brother Jack was a sexual beast, Jo realized, even if he didn't know it yet.
Jo also knew that she was bored with her current casual dating system. She didn't realize until she touched her brother's cock that she actually didn't like any of the men she was using for sex, not even a little bit. She mostly only dated them because they were popular, not because they actually turned her on any more than she could turn herself on with her dildo. She was bored with it, bored with taking the easy way out when it came to orgasm. Jo didn't want that anymore.
And besides, she thought as she started texting each and every one of her boy toys telling them "It's over!" And then deleting their numbers and blocking them, I'm the most popular girl in school, maybe even town, and I deserve the very best... My brother's cock is the very best!
Jo then proceeded to take her 7" dildo out from her bottom drawer where she hid it, and masturbate herself to two orgasms in a row as she imagined her brother's cock, knowing her dildo didn't compare to the mammoth beast she saw in the other room.
Once that was over she calmed down and realized that lusting after her brother was not something the most popular girl in school should do. She decided that she wouldn't do anything with him, as that would be too weird, but she didn't regret breaking up with all her boyfriends one bit.
I can't fuck him, but I can at least help him gain some sexual experience. She thought as Jo's mind was already coming up with other fantasies once again. I wonder if I could hook him up with someone... She began fantasizing about her brother hooking up with her as she worked herself up to a third orgasm before falling asleep once again.
Saturday, September 17
1
"Hey what's up?" Clara said to her cousin Jo after they finished yoga and took turns using the shower.
Jo was sitting on the couch in the living room and reading a fashion magazine, "I'm reading." She responded casually, not looking away from her magazine.
"That's cool," Clara said as she sat next to her cousin and best friend on the couch. She then leaned over to read over her shoulder.
This annoyed Jo, but only a little bit. She put the magazine on the coffee table, "What is it?" She asked.
Clara shrugged, "Just we're usually at the mall by now. Or wherever. Probably so you can, y'know, avoid Jack." Clara said. She always assumed that was the reason Jo usually rushed them out of the door early after yoga on the weekends anyway.
Jo rolled her eyes, "I don't do it to avoid him." She explained, though that was a total lie (just not anymore), "In fact, I have an idea I wanted to run past you..." Jo actually hadn't been thinking of letting Clara in on it but realized that Clara would figure it out eventually anyway, "I was kind of thinking of taking Jack to the mall, actually."
Clara smiled. She actually liked Jack a lot but was just a lot closer with Jo and the two didn't seem to get along to her. "That sounds like a great idea!" Clara said just full of enthusiasm. "But why do you want to take him along with us now?" Clara already assumed that Jo meant both of them, "Also, will Rose be there?"
Jo bit her lip as she contemplated that. She actually hadn't thought of Rose, who would probably text her soon wondering where she was, "Um, no Rose." She definitely wouldn't understand, "It's an idea I had." Jo paused. Clara wasn't very bright, but she was amazingly kind, still, she probably wouldn't completely get what she was trying to do, "It's...stupid." Jo said, believing it, "Maybe we should just go out with Rose like usually." Jo decided to give up on that idea, and maybe stop thinking of her brother as anything more than her brother...
Clara frowned, "If you just tell me I can let you know what I think of it." She said sweetly. "I promise I'll love it, whatever it is." Clara really was a caring person.
Jo took a breath, "Okay, thanks." She scowled, still not sure she could say it without coming off like a total weirdo, "Well, you know that Jack is, um, not very, um, experienced." She said, still sure she was about to let something slip and Clara would freak out.
But Clara surprised her and said, "You mean sexually?"
"Yes!" Jo was relieved, and said more confidently, "I dunno, I was just thinking maybe I could take him to the mall and help him out with that."
"What? Have sex with Jack at the mall!?" Clara said, a little too loudly for Jo's tastes, and then laughed.
"What? No!" Jo said, a little too forcefully to be completely convincing but she was also glancing around to make sure her mom or aunt weren't around. She breathed a sigh of relief when she saw they were both outside doing yardwork.
"Then why would taking him to the mall help get him laid?" Clara asked.
Jo rolled her eyes again, a common occurrence when she was talking to Clara, "I thought that I could teach him about dating. You know? Take him to the movies. Out to lunch. Show him what women like from the men they date. That sort of thing."
Clara wasn't listening then, "Uh-huh." She said, "Should we go wake him?"
Jo was suddenly incredibly nervous about doing that. "Um, no. Let's just watch TV until he wakes up or something." She suggested.
"Oh sure." Clara said as she sat next to Jo on the couch. She flipped on the telly and they started watching some game show.
Except Jo wasn't really paying attention to it. She started thinking about why she suddenly felt so nervous. This is Jack? Why am I stupidly worried about talking to him all of a sudden? I don't get nervous when I talk to any other guy. Why would my brother, my loser virgin brother, make me, I dunno, so weak in the knees? Like there's suddenly butterflies in my stomach when I think about him?
She felt herself breathing harder, her heart beating faster. Jo had never felt this way before and she was pretty sure she didn't like it. What the Hell!? He's a loser! HE'S MY BROTHER! CALM DOWN! HE'S A LOSER! HE'S MY BROTHER! CALM DOWN! She kept repeating that to herself in her mind in the hopes it would help things. It didn't.
It's just his cock, right? Jo thought after her mental mantra chanting didn't help, I mean, if anyone else had a cock like that, I would be just as obsessed with them. I mean, imagine if our Principal had a cock like that... She pictured the principal with his giant fat ass and a huge cock like her brothers standing in front of her. Jo almost threw up in her mouth. Okay, maybe it's not just his cock. Maybe it's because he's such a loser. I'm nervous that if he's no longer a loser and becomes popular by having to beat off women left and right with his massive cock, then we'll have to hang out together! UGH! But even as she thought that, Jo knew she didn't really mean it.
She pictured eating lunch at school with her brother, Jack. Jo felt those same butterflies come back in her stomach as she knew that it wasn't just his humongous cock and it wasn't that he was a loser either. Jo knew what it was. She had a crush on her brother...
As if realizing that summoned him, Jack wandered into the room in some shorts and a t-shirt, looking like he just woke up and threw those on.
"YAWN! Good morning." Jack said as he walked past his sister and cousin on the couch without looking at them to grab some cereal from the cupboard.
Jo just stared at him, spellbound. As if she'd never seen him before, and he was also glowing like a god or something.
"Good morning!" Clara said happily. But she noticed Jo's odd expression when she looked over, "You okay?"
Jo looked away from her brother then, "Um, yes. I think, uh..." She stuttered.
Clara had never seen her cousin this way, "You sure? You seem...off."
Jo took a breath and gathered herself, "Yes. Sure. To prove it I'll go tell Jack the plan." She stood up and boldly walked into their dining room where Jack was eating cereal.
2
Jo came up to him and put a hand on the chair across from him. She struck a pose. She was trying to do something that was sexy, classy, and sisterly all at once, but failed at all three.
It didn't matter anyway since Jack was busy reading the cereal box instead. "You're usually not home now." He mentioned, a mouth full of cereal, still without looking at her.
Jo scowled and pulled the chair out to sit across from her brother, "Same ol' Jack." She commented, disappointed, and she sat down. She decided not to be coy, "I thought you, me, and Clara could all go to the mall today."
Jack slurped some more of his cereal, "You buying me school clothes or something?"
Jo was getting annoyed, "You know, you can be really dense sometimes! This is why we didn't hang out before!"
Jack was very confused, but really didn't like to be yelled at, "Then what are you doing!? Why do you want me to go to the mall with you!?" He yelled back.
This caused Clara to jump up from the couch in the other room and run into the dining room. "We're going to teach you how to date!" She shouted with excitement.
Jack was more confused than before, "What? I don't need to know that." But then he remembered that he can't cum without help and it was just his normal reaction to reject Jo and Clara's plans most of the time, "Actually I probably do need to know that..." He added miserably.
Jo suddenly perked up, all her anger and annoyance at her brother disappearing, "Oh good! Let's go now!" She said with way too much enthusiasm. "Um...I mean, if, uh, you want to, that is..." Jo added as she blushed profusely.
Jack shrugged, "Sure, whatever you two want to do." He was still half sure this was some kind of trick since he'd never gone out and done anything with his sister, outside of family obligations. But Jack would rather put faith in people most of the time than doubt them, even when one of them was his bitch of a sister.
3
When they went out to Josephine's car, Jo handed her keys to Clara. "Do you mind driving there? I thought we could teach Jack something on the way."
Clara shrugged. "Sure thing." She didn't see why not, also she was curious what the dating lesson was on the way there and why she would have to drive for it.
Clara got in the front, Jo got in the back. Jack was about to get in the front when Jo told him, "No, bro, get in the back with me. It's your first dating lesson."
"Um, okay," Jack said, basically willing to do whatever it took to get through the day alive at that point, so sure he was that Jo and maybe Clara too were about to do something really mean to him.
He got in the back. Jo got in on the other side. She smiled at him. He glanced at her nervously and then looked out the window.
Jo scowled at his reaction. And felt like punching him. Except this is my fault really, she thought bitterly as she felt that butterflies returning, I'm the one who's always dismissed him in the past. Just because I'm popular and he isn't...I've been a real bitch to him, haven't I?...
Jo felt like crying all of a sudden. She knew a good way to fight back the tears, since the last thing she needed was to start crying in front of Jack, was by getting very angry. Jo ended up punching her brother anyway.
"OW! What was that for?!" Jack said, feeling his sister might have completely lost it.
"I'm trying to teach you stuff! Don't ignore me!" Jo spat angrily and that calmed her down, "And I want you to pretend," she explained, "That you and I are on a date."
Jack did a double-take, "W-w-what?"
"It's just pretending." Jo said, acting innocent, "I just thought you could use some practice for when, um, you know, someone, um, might, uh, want to date you. You know? I mean, uh, not that you know just that it might be someone you know... NO!" Jo just shut her mouth realizing she just kept putting her foot in it when it was open.
"Oh! Can I be Jack's pretend date too!?" Clara asked enthusiastically as she drove, glancing at them in the mirror. "It could be a double-date!"
Jo groaned, "That's not what that means!"
"I know," Clara said, annoyed, "but I still want to be Jack's pretend date too!"
Jo didn't like that, of course, but she also didn't really want Jack to know that she had a crush on him, "What do you think Jack?"
Jack was not sure at all what was going on and was half expecting to wake up from this weird dream he was having, "I guess...that's cool." He said after another minute.
Jo was disappointed but didn't show it outwardly. It doesn't matter, she thought a moment later, Clara probably doesn't know what's really going on. This is all just a game to her. That cheered her up.
"Okay," Jo said after another minute of driving and she turned to her brother, "Well, I'm your date for right now. So how about you put your arm around your date." And she grabbed Jack's arm before he could do anything else and draped it over her shoulder. She then nuzzled her head into his arm and took a whiff of her brother's masculine scent. Jo leaned over, lay her head on her brother's shoulder, and closed her eyes just to drink at the moment. It felt nice.
Jack was having mixed emotions. He was still fairly certain his sister was about to pull a knife on him and stab him in the chest or something. But he was also very intrigued by the feeling of her head on his shoulder and as he draped his arm over her he could lay his hand on her belly, covered by her shirt, which he laid there now just to see if Jo would do anything.
Jo did do something. She hummed happily and put a hand on her brother's to make him hold her by the waist more tightly. "You know, Jack?" She asked dreamily as she opened her eyes to look into his handsome brown ones.
"Uh, what?" Jack said, feeling strange as he stared back into his sister's green eyes as her red hair flowed down around her face.
"You're really special to me, Jack," Jo told him, only wishing it was something more to really express what he meant to her, and went back to leaning her head on his shoulder. Part of her wanted to kiss him but those damned butterflies were back again. Also Clara was there and probably wouldn't approve, but Jo had kinda forgotten about her at that moment.
Jack was taken aback by that, "Um, thanks." And then a moment later, "That's probably the nicest thing you've ever said to me."
Jo punched him again, "I'm not that mean!" But she was being playful.
"Ow! No," Jack said, with a laugh, "I just meant it was really nice." Jack took another moment, lightly moving his hand along her belly. "You're special to me too, Jo." He told her after another few seconds of silent driving, "I know we don't, um, get along." He felt strange saying that since it seemed they were getting along now, but he continued anyway, "but I've always looked up to you. Really respected you. You always get what you want it seems, and it's like it doesn't take you any effort at all. Meanwhile, I work as hard as possible and usually fail. I guess I've been spending a lot of time being jealous of you actually, but really I think I'm just proud at least one of us is so successful at life."
Jo looked at him again, Jack's brown eyes were captivating, "And now we're even." She said as she smiled broadly, "Now that's the nicest thing anyone's ever said to me." And then those butterflies were back, but this time it was because Jo just leaned in and kissed her brother on the lips.
Jack was so surprised by this his lips didn't do anything at all for a few seconds while his sister's lips seemed to quickly nibble on each and every part of his closed mouth for a brief moment. And then it was over. Jack was just staring at his sister wide-eyed, completely unsure what he was feeling anymore.
"I'm sorry, I don't know what came over me," Jo said as she pushed his arm away and moved to the other side of the seat. Jo was too embarrassed to look at him and instead just stared out the window.
Jack did the same to his own window until Clara announced, "We're here!" And they pulled into the parking lot of the mall.
4
As Jack walked towards the doors, Clara held Jo back for a moment, "So...I saw you kiss your brother." She said with a wink and then a laugh at Jo's completely mortified expression.
"That wasn't what it looked like," Jo said, not sure what else to say.
"Uh-huh." Clara said with a smile, but also completely unbelieving of Jo's statement, "You know he has a gi-NOR-mous cock right?"
Jo huffed, "I was aware." She said as they slowly walked far enough behind Jack so he couldn't hear them.
Clara ignored how annoyed and upset Jo was to keep joking, "You going to add him to your boy toys? Your own brother in your little black book?" She laughed and mimicked talking on the phone in Jo's voice, "Hey bro, I'm horny. Want to come across the hall?" Clara laughed again, finding her own joke very funny.
Jo scowled, and stopped walking, letting Jack get really ahead of them. "If you must know, I broke it off."
"With who?" Clara asked still all smiles.
"All of them." Jo put simply and started walking towards the mall again.
Clara stood behind for a second as she put 2 and 2 together. Then she got really excited as she caught up to Jo before she caught up to Jack.
"You have a thing for your brother!" She whispered excitedly to Jo.
Jo hit her in the arm. She felt she was being extra violent that day, "Shut up, okay? We'll talk about it later!" She whispered back. They caught up to Jack who hadn't even noticed they weren't walking with him. He had been completely lost in thought.
Clara was still kinda looking at this as a sort of game. But now it was one with stakes! She took Jack by the hand, "Remember, I'm your date today too." She then smiled like the devil at Jo, hoping to make her jealous.
Jo glared back at her cousin, wishing she were evil so she could hate her. Instead, she just felt annoyed at her otherwise very nice and sweet cousin. Jo walked up to Jack on the other side and grabbed his other hand, forgetting completely that she was still feeling embarrassed about that awkward kiss in the car, "Remember I'm your original date though so you should pay extra attention to me." Jo told him.
Jack still felt odd. Like he'd stepped into the twilight zone, totally opposite of how normal he thought everything was yesterday. He did like the feeling of his sister's and cousin's soft hands in his own, and they both smelled really good right then, but he had to keep reminding himself that these two hotties on his arms were his sister and cousin.
They got to the mall entrance. But as soon as the automatic doors opened, Jo let go of Jack grabbed Clara and they hid around the corner.
"What is it?" Clara asked legitimately concerned for her cousin.
"Ugh, one of those guys I used to date is in there," Jo said as she rubbed her eyes. Because her eyes were covered she didn't see that Jack had walked up behind Clara and she said, "The last thing I need is for the whole school to find out I have a crush on my brother and-"
"You have a crush on me?" Jack asked probably the most confused he'd ever felt in his life.
Jo looked up and saw Jack, no. No. NO. NO! She thought over and over again for a very long time. Not saying anything at all while her face flushed a deep red and her gaze slowly moved down to get feet.
"Umm, well," Clara said hoping to clear the air, "Jo kissed you in the car, do you remember that? And then she told me she broke up with all her boyfriends and, OW!"
Jo had stomped on Clara's foot to get her to stop talking. Then, too embarrassed and angry to speak she started walking back to her car.
"Hey, what'd I say!?" Clara shouted at Jo as she walked after her.
Jo started walking faster to get away from her.
"Hey Jo, wait up!" Jack yelled after her as he ran up to her. Jo did stop then to wait for him.
"What do you want?" Jo said. She sounded annoyed to Jack.
"I just wanted to say," Jack blushed and went on nervously, "I've never been on a date before."
Jo was taken aback, "I know, that's why I-"
"No, I don't think you do." Jack said, "I mean, not right now anyway...you've been on so many dates. I mean, now you don't have any boyfriends but you used to and, um..."
"I get it what are you saying?"Jo said, not at all insulted by Jack's ramblings.
"Well, I just want us to have a good date is all, being they it's my first. I just wouldn't want it to end with my, um, 'girlfriend' angry at me."
Jo felt her heart grow three sizes, Jack does want to go on a date with me! She suddenly hugged him feeling like a million bucks.
"Thank you! Thank you, thank you, thank you!" Jo said, feeling she'd never felt so grateful for anything in all her life. She broke the hug, all smiles, but a bit embarrassed, "Where do you want to go for our date?" She asked, "You asked so you have to choose?"
"Oh is that how that works?" Jack asked.
Jo smiled, "Not really. Every date is different. That's your first lesson." She then laughed feeling giddy.
"In that case, I'll let the driver decide where we go." Jack said and nodded to Clara. "Someplace romantic."
"Yes sir!" Clara said as she gave him a salute.
5
Jo and Jack got back in the backseat while Clara drove. Jack put his arm back around Jo's body. And Jo leaned into him.
"I hope I didn't ruin your first date," Jo whispered to him.
In answer, Jack held his sister a little tighter.
Clara parked somewhere nearby on the top of a hill that overlooked the rest of their city. It was a really nice view.
Jo wasn't paying attention to where they were going until they got there, "This is Make-Out Point!" Jo complained once Clara had parked. It was called as much because of how often teenagers were caught parking there.
"Yeah, it is," Clara happily agreed, "Jack said to go somewhere romantic, and I find this place very romantic!"
Clara climbed over the seat into the back and got on Jack's other side. Jack and Jo had to move over so she could fit. Once she was there she grabbed Jack's other arm and put it around her shoulder. Jack now had two of the hottest girls in his school on either arm. Even though they were his sister and cousin he was suddenly very nervous (maybe especially because of that reason).
"Umm, what do we do now?" He asked since he really wasn't sure.
Jo opened her mouth to give some advice, but Clara spoke first.
"It's called Make-Out Point for a reason," Clara said, "You wanna make out?"
Jack was surprised but the suggestion but Clara didn't let him answer before she leaned in and started kissing.
"Wha-What!?" Jo complained as she watched her brother and cousin kiss. She seethed with jealousy, which only grew when she saw that Jack was kissing Clara back!
He hadn't done that with me! Jo thought bitterly wishing she had been more up front with him earlier about what she wanted from him.
There was a honk of a car behind them. Someone had pulled up in the parking lot with them.
Jack and Clara stopped kissing. Jack looked the most embarrassed Jo had ever seen him. Clara seemed fine, however.
The person in the car got out and came to the side of the car. "What's going on in-"
It was Beth Ryder, Jack's first-period history teacher but she taught all three of them at different times on school days. She knew who they were and that Jack was Jo's brother and that Clara was his cousin.
When she pulled into the parking lot, there usually weren't cars out there until the evening. She liked to come out there to read, or be alone with her thoughts, or to smoke a big fatty. Beth was just surprised that there was another car there this early in the day. And one that she recognized.
It was Josephine's, one of her students, she knew because Beth saw Jo park it almost every day of school because they got to the building at roughly the same time And when she pulled up and saw two kids making out in the backseat, but not just two, three! And she looked at her horn to get them to stop.
Beth came up to the door, assuming she was going to have to tell Jo to not have threesomes in public, of all the things to have to tell someone. She did not expect the three people she saw to be siblings and cousins to each other.
"What the hell are you three doing?!" Beth said, angry more at how much this situation confused her than anything else.
"Umm..." Jo and Jack said together as they both tried to think of some excuse. Jack had moved his arms away from both of them and used his arms to cover the obvious tent in his shorts.
Clara, however, didn't hesitate, "We're teaching Jack about dating!" She said happily. But then went into some sort of trance as she remembered kissing her cousin, that might have been the best kiss of my life! We didn't even use our tongues! What the flying fuck?!
Beth blinked, "By making out with him!?" She accused.
"Huh?" Clara said, already very distracted by her horny feelings for her cousin right then.
"Ah, okay, that was my fault," Jack said, nervous but doing his best to cover it up, "Um, I read a lot, as you know..." he added. He and Beth discussed the books they read on occasion, "and the was a romantic scene in one that I didn't understand and we were kind of, umm, acting it out. We weren't kissing," he added, "our, um, faces were just close together."
Beth considered this. "Then why do you have an erection?" She was not leaving any stone unturned.
Jack looked away from her nervously and instead out the window as if he were looking for a bird he thought he saw. He didn't know how to answer that.
Here Jo stepped up. "Oh my God, Miss Ryder. Jack is always popping boners all the time. It's been happening pretty much since he whipped his dick out in your class," Jo was pretending to be angry but that turned into real anger, "Why do you think we're trying to teach him to date! He has a real problem!"
Beth nodded, "Because he can't masturbate." She said without thinking. Or really she was, but thinking about the doctor's note that Jack gave her, the same one he had given to the principal.
"What?!" Clara and Jo said together. This was news to them.
Beth saw Jack flush an even deeper shade of red. She realized that Clara and Jo obviously didn't know about his condition. "Umm, sorry," she mumbled out, ashamed for revealing one of her favorite student's secrets, "I'm going to go, but you three just go straight home okay?" She said before getting out of there quickly.
Jack got in the front seat before Jo or Clara could say otherwise and drove off.
Beth watched them go and thought about everything she just heard and seen. I thought for sure I saw lips locking but I must have been imagining it... Is Jack getting dating tips though? Or need to act out romantic scenes from books to understand them? That boy obviously doesn't know the first thing about the opposite sex...
Beth thought about Jack for a moment longer but then decided to push the whole thing from her mind. She took out her joint from the glove compartment...
6
On the ride back home Clara asked Jack to turn the radio on. It was a lot harder to hear people in the backseat when the radio was on. Jo knew what that meant, Clara wanted to talk about something.
Jo was still angry with her cousin though and didn't really want to speak to her.
Clara ignored her cousin's dismissive attitude, "Oh my God Jo! I see what you like about Jack!" She whispered excitedly.
Jo was visibly upset now, mostly because Clara had done this before, "What? You're going to steal another one of my boyfriends?"
Clara was surprised, not because Jo had just referred to her brother as "boyfriend," but because they'd talked about this, "I thought we agreed we wouldn't be jealous of each other. Y'know? Keeping everything casual?"
Jo closed her eyes in frustration when she realized that Clara was right. But still, she didn't think Clara would even be interested in Jack... but realized, This is my fault... Clara's always been copying me. And it's true that we've agreed to never be jealous of each other, but Jack's different...
Clara noticed Jo getting really quiet. She knew she was upset with her but she wanted to give her the good news. She leaned in and whispered, "Jack's an amazing kisser."
This distracted Jo from her thoughts. She scowled at her cousin, "When I kissed him he didn't react at all!" She said jealously.
Clara smiled like the cat who ate the canary, "It was probably the best kiss of my life and we didn't even use our tongues!" She whispered fiercely.
Clara went back to her side of the seat and they road the rest of the rest home thinking their own thoughts.
7
That night Jo was up late thinking about her brother. Mostly thinking how he had actually kissed Clara and had been like a dead fish when she kissed him. She waited until everyone else was asleep and then snuck down the hall and into her brother's room.
She was just going to shake him awake but remembered that he slept naked. Also being close to him was making her feel... strange. Jo got into bed next to Jack and snuggled against him under the blanket. She was wearing her PJs but she could feel her pussy getting wet as she took in the feel of her brother's body as she spooned him. She smelled his masculine scent. Jo wasn't sure what was getting into her as she lightly licked his neck, a thrill going through her whole body as she did so.
This feeling woke Jack up. As he stirred, Jo moved her head away from his neck but continued to spoon him with her arm and leg. Jack looked at her in the darkness incredibly confused, "Jo?"
Jo suffered a mix of emotions at that moment. For one thing, she thought, I'm so fucking horny right now! It's even hotter that I got caught doing something so naughty! Jesus! What a thrill! For another, why do I keep getting those damn butterflies in my stomach when I do things like this? Is it because it's my brother? I mean, imagine if he wasn't! The biggest loser in school with the most popular girl! He'd jizz in his jeans every time he saw me and it would be something else entirely then... I could use him however I wanted. Fuck him, leave him, make him eat my pussy, take him to the movies...leave him for my amazing brother...
Jo just stared at her brother in the dark as her brain ran rollercoasters around in her head. After a minute Jack was starting to feel very awkward, "Why are you in my bed?" He said, "You know I sleep naked right?" He wasn't sure what was going on with his sister lately but this day was getting weirder and weirder.
Jo lost every nerve she had coming in there. She pushed away from him and got out of her brother's bed. She turned to say "sorry" at the very least, but the words caught in her throat. Jo then walked out of the room, totally lost as to what was wrong with her lately.