Adventures of Derek and Amy Ch. 01

The flight back from California to the east coast was long. The movies were lame, and Derek didn't feel like reading. He had the internet connected now and scrolled through his phone.

"Hey Bro," Derek's sister Amy sat down next to him. Derek is 22, a fifth-year senior in college, standing 6'1 with curly brown hair.

"Slumming it back here with us regulars in economy?" he asked her.

"Mom's asleep," she replied. Their mom Claire is a local TV weatherperson, a hot MILF that they parade out there to get more male viewers and keep their attention. She has first class seats but only for two. It was his turn ride in the back of the plane. It suited him fine; the last few rows were empty, and he didn't need to hear his sister drone on about relationship gossip from her celebrity rag.

"What'cha doing?" She asked, trying to peek at his phone.

"Just Instra-scrolling," he turned the screen away from her prying eyes.

"Checking to see if Becca misses you yet?" She asked, but she already knew the answer. And she wasn't wrong. "She's no good for you," she went on.

"You're just jealous," he replied.

"Of what?"

"That I'm getting action and you aren't."

"Oh," she perked up. "Did you two do it already?" She was snooping for information.

"We made out at Todd's party. But it will happen soon..."

"Does she play hard to get?" she needled at him.

Derek unlocked his phone and showed her a text from Becca, with pics. The first showed her pulling down her shirt with her finger to reveal ample cleavage, stopping just above her nipples. The second showed her bending over the kitchen table with her skirt riding up just enough to see her panties.

Below it was the text: Time to take this to the next level, stud.

"Or maybe she's a slut now," she pouted. Derek had a great relationship with his sister, they talked about friends and more, often showing their text threads, Facebook, and Instagram posts.

"Hey, don't be like that. Don't tell me you never sent a suggestive pick to a guy." He hoped her response would be that she never had. After all, she was his younger sister. But at 20 and in college, she's getting more attention every year. Amy is 5'4" with long, dark hair and soft brown eyes. Her breasts are filling out nicely on her slender frame. And if he noticed then certainly other guys had too.

"I'm just saying," she turned in the airplane seat. "You could do better."

"Are you two fighting over a guy? You're not still stewing over her getting to Todd first last year?"

Todd and Derek had similar friends, but we weren't best buds. Still, he knew enough about his exploits. Just so long as they weren't with his sister. So, when Becca and Todd were going out, he felt better about where his attention was focused. But that was last year, and they had eventually broken up.

"I would have thought that since Todd is available that would make you happy."

"I'm over him," Amy said with a tone. "But she's just working you to get at me." Derek knew Amy was still hurt over how it all played out. And now Becca was showing interest again it rankled his sister.

"Maybe," he replied knowing how the game is played. "But she's fucking hot."

"Hey!" she slapped his arm.

"I'm just saying," he shrugged his shoulders.

Amy looked down at her lap, wringing her fingers, trying to figure out how to say something.

"I don't want you to go out with her anymore," she said quietly but firmly.

"Amy, I don't tell you who you can or can't see," he replied with growing concern. "I don't see what business it is of yours anyway."

"You have to take family into consideration."

"Seriously?"

"I'm just looking out for you," she placed her hand on his arm lovingly. "Being a good sister, that's all. She's no good for you."

"I think you're playing some game, competing against her and manipulating me to your advantage."

"She's manipulating you with the prospect of sex," she added, "to her advantage."

"Well," he nodded approvingly. "She's hot and guys like sex, so..."

"Hey!" she socked him in the shoulder this time.

"Ouch!" he grabbed his bruised arm.

"That's not polite to say to another woman," she retorted.

"Well, you're hot too," he added, "But you're also my sister, so..."

"Hmph!" She looked at him with knives and spent a minute working something through in her head.

"I could set you up with Jill," Amy finally broke the silence.

"What?" He said with curiosity.

"If you break it off with Becca, I'll set you up with Jill."

"Why would I do that?"

"Don't you like Jill? She's pretty."

"Yea, sure," he was momentarily thrown. "No, what I mean is, why would I give up on one girl who I've already put the time and effort into and who's ready... for a first date with one of your friends? It might not even go anywhere."

"But it might," Amy added. "Becca is too manipulative. You deserve someone better than that. Jill is pretty, and she's super sweet! I like her..."

Derek looked at her pleading eyes. She touched his hand with hers, and just ever so gently pressed her breasts into his arm as she leaned in. It was a tactic she had used well over the years, to encourage him to do as she wanted. And she knew that he knew what she was doing. She didn't seem to mind or care, or perhaps she simply knew it was working, like it always had before.

Derek looked down into her chest, trying not to be obvious. He once heard her while shopping for bras about being a 34-C. He didn't mind if they weren't the biggest, he just knew he liked it when she brushed them up against him. He let her play the game, as long as he got an occasional touch.

"Let me get this straight, I should let you maneuver me into dumping my girlfriend because she's too manipulative?" He let the irony sink in.

"And you'll earn my undying love!" She teased him, making a heart symbol with both her thumbs and forefingers.

"What, I don't have that already?" He teased her back with a smirk.

"So, you'll break it off?" She changed her tone.

"I'll think about it," he replied.

"By the time we touch down," she said matter-of-factly.

"Wait, what?" he asked incredulously.

"I don't even want her to be there when we land."

"Hold on. What about the welcome home party tonight?"

"Yea," she shook her head. "About that. Tell her you can't make it - change of plans." Amy pulled out her phone and began slowly speaking as she typed - speaking the same words that she now texted to her friend.

Hi Jill, how about you come over and watch a movie with my brother and I after we get back tonight. We'll order pizza, get some drinks. Netflix and chill. PS - Derek likes you.

Amy showed him the text in draft mode.

"Should I press send?" She blinked at him and smiled, suggesting he go along with her plan.

"Do I have any say in this?" he admired her efficiency.

"Not really." She sent the text, then looked up at him. "Your turn."

"What?"

"Text Becca."

"Now?"

"Yea, now. Or I can," and with that she leaned over him to reach for his phone that was on the far seat. Derek grabbed it first and held it just out of her reach. Since her arms weren't long enough, she retreated, but not before slowly and deliberately brushing her tits against his arm for maximum effect. He had to shift in his seat, his shorts starting to choke his growing member.

He wanted to reach out and grab them. It's one thing to feel a woman's breasts during a hug against your chest. It's another to get your hands on them, to feel with your fingers, the nerve endings sending exciting messages back to the brain.

In Derek's mind he had touched her breasts before. But only in his dreams - both waking and sleeping. And occasionally while jacking off. While Becca had an overall nice body, Amy was pretty and sure had nice tits. And now she was actively trying to use them to get what she wanted.

To be sure, Derek had seen her tits outlined nicely in her sports bras, and in her swimsuit poolside. He used to try and peek at her changing. Once he had watched her taking a shower, washing herself. He used to think she did it slowly, seductively, touching herself on occasion. He pretended that was for him. Once he thought she caught him, but she hadn't said anything and just kept going.

Derek imagined her breasts were like peaches, a nice combination of being firm and soft, nice to touch and maybe to taste...

Just then, her phone beeped - a reply came back.

Sorry, can't tonight. Already have plans with my brother and mom. Going to get that Caribbean trip, one way or the other. [wink emoji]

Then another text shortly after:

Maybe some time next week? Definitely interested. [double wink emojis]

"See," Amy made sure he saw the reply. "She's 'definitely interested'."

"That's nice, but that doesn't say anything specific," he replied. "She could just want to come over and hang out."

"No, it will happen," she closed out of her messages. "Trust me."

"Look, I haven't said 'Yes' to any of this," although he was intrigued. "I may still want to see how things play out..."

"Nope," Amy wasn't giving up. "Not happening."

"You're crazy," he said leaning back into the seat and looking ahead, not giving in.

"I'm just persistent. I get what I want," she said matter-of-factly.

"And what about what I want?" he asked, looking over at her.

Amy cocked her head, smiled then changed her expression - which worried him.

"Well, what do you want?" She said as she turned towards him. Then she did something unexpected - with a hooked finger she began pulling down her top at the neckline, exposing her cleavage and stopping just above her nipples. Just like in the picture he had showed her earlier.

"Two can play this game," she said flirtatiously.

Now Derek didn't have to hide the fact that he was staring at her tits - she was encouraging him to.

After a moment that seemed like an eternity, she pulled her top down more, her nipples just barely peeking over the edge. "See something you like?" But she already knew the answer.

"Oh man," he licked his lips and shifted in his seat. She released her finger, and her top sprang back up. Amy hooked under her shirt and pulled up, high enough to expose under-boob.

"How about now?" She made sure she had his undivided attention. She pulled up farther as her top cupped under her breasts, outlining and lifting them like, well, peaches.

"They're beautiful," he said honestly. "You're beautiful," he looked into her eyes, then back down.

"Why thank you," she said seductively. "You want to touch them?" now she was offering herself openly.

"You have no idea how long I've wanted to," he said mesmerized, and slowly began reaching for her, wondering if he were in a dream and if this was really about to happen.

Derek finally squeezed his sister Amy's tits, albeit over her shirt. She moaned as he squeezed again. He shifted his position, part to adjust for his growing cock, and part to reach in with both hands.

After 4 or 5 full hand grabs, Derek went under her shirt. He slid his hand along her torso, feeling her soft skin, exploring her slowly but with purpose. He was determined to go as far as she would allow, but to this point she made no complaint.

Derek reached up to her chest and caressed her breast, first from below cupping, then from the sides grasping firmly. Amy squirmed and sighed. With his other hand he lifted her shirt, fully exposing her chest. He leaned in and opened his mouth, intent on licking and sucking on her tits.

"Uh-uh," she blocked him with her hands just inches before his mouth reached her nipples, "after you text her," she directed as she pulled her shirt down. He had to remove his hands as she backed away.

He was shaken from his daydream and looked at her square. "Don't tease me," he pleaded.

"I use these to my advantage," she said as she shook her chest slightly, squeezing in her arms and pushing her cleavage up and out. "You will be rewarded."

Derek looked at her with questioning eyes, to be sure they understood each other.

"As long as you do as I ask," the challenge was there.

"You play a dangerous game," he said honestly.

"And I intend to win," Amy said as she sat back, one leg underneath her. She still pressed her chest outwards to show him her goods.

They had crossed over into unchartered territory, the possibilities were tantalizing. Derek looked at her, his younger sister. But she was also a woman: beautiful, sensual, aware of her sex, her power. Her eyes beckoned him from behind a wave of hair falling in her face. He loved it and she knew it. She was practicing the art of seduction. And she was getting better at it with each moment.

Amy was panting, her chest moving in and out. Was she excited from pleasure or nervousness? He couldn't be sure, maybe it was both.

Derek reached for his phone and found the last message from Becca that he could reply to.

His fingers typed in the text he had to send:

Can't meet tonight, something came up.

He showed her the text in draft mode.

"It's a nice start," Amy said. "But I said you have to end it with her."

"You said I had to tell her there was a change in plans."

"There is a change in plans," she added. "You'll have a new girl next week. But you should break it off with Becca if you want to start something with a new girl. If that's what you want," she teased him.

"That's not equitable, even if you do let me touch. And it's you that want me to break it off with her."

"So, we agree to the deal in principle," she went on, "now we're just negotiating the price."

"The price?" he asked curiously.

"Yeah. What will it take for you to break it off with Becca, now - before we land?"

Derek's mind raced with the possibilities. He looked around, but everyone on the plane was quiet, involved in their own lives - watching movies, sleeping.

"I want you to suck me off," he replied quietly. His confidence was a bluff - internally he was nervous, not sure how she would react, if he would get in trouble. But he was going to find out how much she really wanted to control him.

"What the fuck?" Her eyes went wide. "You pervert! Can't there be something else? Money, chores, anything?" She acted incredulous, but that could have been part of the game.

"You're asking me to end a relationship for your reasons, not mine. And things are progressing, physically. It will happen, trust me. If you want me to give that up, you have to offer something comparable."

Amy thought about it, but she knew it was true.

"Fine, when we get home. But end it now."

"Nope," he pressed his advantage, hooking her in with the bait of control. "I'll break it off after."

"But I need you to do it before we land."

Derek shrugged his shoulders and nodded - yeah, that's right.

"What," The realization hit her like a ton of bricks. "Here? On the plane?" She whispered in surprise, then looked over the aisle of seats.

"You're the one indicating a sense of urgency," he said, letting the idea sink in.

She bit her lower lip and contemplated the situation. "How will I know you'll go through with your end of the deal?"

"I could say the same thing to you. After I break it off with her, you could just walk back to your seat like nothing. What am I supposed to do, tell mom you won't suck me off?"

"Shhh... not so loud!" She pleaded.

"You know I never lie to you. If you do this for me," he said in all seriousness, "I will do as you ask."

"OK. For how long?" She asked, trying to limit the damage.

"What do you mean how long? Until I come in your mouth. And you have to swallow."

"Fucking pervert, no way!"

"That's what 'suck me off' means," he retorted. "What's the big deal. Just act like I'm a guy you met at a party and hit it off with."

"Just so you know, I don't just go sucking any guys dick I just met," she pretended to be offended.

"OK, like a guy you've dated a couple of times, and the chemistry is there."

"Chemistry?" She questioned with her eyes.

"Yea, I like you," he replied. "No, I want you," he risked it a step further. "And I think you want it, too. Tell me I'm wrong."

She didn't answer that directly. "But swallowing?" She was only objecting to part of it.

"Otherwise, it will make a mess. Anyway, that's the price."

"Urgh!" she said, losing the fight. "OK, but you and Becca are so over! Bathroom - 2 minutes!" She got up and made a pointing gesture towards the lavatory.

"No, wait. Right here," he grabbed her arm. Derek slid over to the window seat, raised the arm rest, then patted the middle cushion. "Lay down like you're taking a rest, with your head on my lap."

"What? We might get caught!"

"Yeah! That makes it more exciting! Besides, what are they going to do, kick us off mid-flight?"

"You know what I mean."

"OK, we'll both have to just try and be quiet about it."

"Seriously, what if the flight attendant comes? Mom would be furious!"

Looking around, he found the blanket they offered for long flights that he had pushed down under the seat in front. She took the blanket and wrapped it behind her like a cloak.

Amy lowered her body down, resting her head in his lap as suggested. Derek pulled the blanket taut, up over the top of her head, then pulled some back for her to breath. And for him to watch.

And with that, she reached over his leg, grabbed his crotch, and fondled him through his shorts.

Fuck! This was really happening! Derek started getting hard, and realized it was time to advance it forward, to not lose momentum. He lifted, unzipped his shorts and lowered them down just enough.

She looked at his cock, then back towards the aisle.

"Don't worry. Everything is hidden from view," he assured her.

"It's not that," she hesitated. "It's just - what are we doing?"

"We're both getting something we want," he replied.

"You play a dangerous game," she added.

"So do you."

Amy turned back and took a long look at his hard-on, a decent 6.5 inches. With a final internal check of the scenario, she took a deep breath as she made the determination to go through with it.

Gently, Derek's sister Amy licked his cock. She rubbed his shaft with her hand and grabbed the base with her fingers. For a minute, she just held the bulbous tip between her lips, pressing with her gums.

Then she started getting more aggressive, licking and kissing the head, then sucking his rod and pulling it deeper into her mouth.

"Fuck," he tried carefully to keep his voice low. "I've dreamt about this for so long. That feels so good!"

"Mm, I bet!" She replied, his dick fully engulfed in her mouth now. She spent a few minutes trying to figure out the right angle, since her body was low, she had no leverage. She alternated with applying pressure around the base, and then changing back to moving her head down best she could.

Derek had his eyes closed, enjoying the sensation of getting his cock sucked by the beautiful young woman. Just as he opened them again to admire her work, he noticed the stewardess walking down the aisle towards the back of the plane.

He gently pulled the blanket over her head and whispered, "hold up!"

Amy stopped, trying not to move and unsure of what to do. He still had his hand on her head, his cock twitching in her warm mouth as she tried to remain still under the blanket.

"Need anything?" the lady asked.

"No, we're fine, thanks!" Derek tried not to act nervous, wondering if his face was red.

"Is she OK?" the flight attendant asked, pointing at his companion.

"Just taking a nap," he replied.

She nodded and went into the back of the plane. She got a pillow and a blanket and headed back up the aisle, clearly servicing some other passenger's request.