Adventures of Derek and Amy Ch. 03

Then she lunged at him for a quick kiss before she wrapped her arms around his shoulders.

"First order of business," she said excitedly. Amy reached over to her nightstand, retrieving the small box she had earlier. "A present for my new secret boyfriend."

"I uh, I didn't get you anything," he stammered. "I wasn't exactly expecting this, and I haven't been out of the house in a while."

"Oh, don't worry, you'll have chances. This is just a perk of having me as your girlfriend." She was shifting on her legs, giddy and antsy. "Go on, open it."

Derek took the box she offered and pulled the bow string. Lifting the top off revealed a small tube of lubricant.

"I don't get it," he said, looking at her quizzically. "I take great care in getting you, uh, warmed up."

"Oh, that you do," she smiled.

"And when we've had sex, you have been, uh, sufficiently lubricated..."

"That's true. You've made my pussy very wet."

"So...."

"Oh my god, are you dense or what?" She laughed as she took the box from him and set it back on the nightstand. She held the tube up between them, winking seductively. "This is for when you put it in my ass, silly boy."

"Oh, fuck me..." his voice trailed off.

"No, for this you're going to be fucking me," Amy said with a devilish grin.

"I've been thinking of this for years... but mom's just down the hall." Derek motioned over his shoulder as if she didn't know where mom's bedroom was.

"And she's fast asleep," Amy replied, clearly indicating she wanted to go tonight. "An extra glass of wine made sure of that." She nodded her head approving of her own actions, quite pleased with herself.

"Well...uh" he hesitated but didn't really have any objection.

Amy was impatient. "What do I have to do, back my ass up and slap you in the face with it?"

"That's a thought," he smiled. "We just haven't done anything with her in the house."

"So? We'll just have to be really quiet about it."

"Quiet?" Derek was still in shock, in disbelief. Was this really happening?

"Now, I have three rules," she was undeterred. Yes, it was going to happen.

"Let me see if I remember: no expectations, no judgement, no regrets?"

"Not quite. Although those are still in play, they were for when we were just getting started."

"Ok, new rules, go."

"First, always warm me up, get me good and relaxed. Take good care of the one on the receiving end."

"I don't have a problem with that," he replied, happily thinking about eating her pussy again.

"Second, always lubricate," and she held up the tube again. "Don't just shove it in dry. Selfish guys don't get invited back for more."

"Invited back?"

"Oh, you're going to want it again, I already know."

"What? How?"

"Let's see: You've fingered and tongued my ass every time you've had a chance - which I appreciate by the way. But apparently, you have an anal fixation."

"I do. Your ass is beautiful. I think about it all the time."

"Plus, I've seen your porn history."

"Oh, yea, about that, um..."

"Third, if I stay stop for any reason at any time, no matter how close you are... it's done. Totally at my discretion."

"Seems fair. I accept the rules." Derek got on his hands and knees and crawled towards her.

"And finally," she continued.

"Wait, four? I thought you said three rules."

"Look, I'm about to have anal sex for the first time. Give me a break."

"Wait, your first time?" He asked playfully.

"Yea, I've been saving it for someone special." Amy leaned forward to kiss him, gentle and soft.

"Lucky me," he added.

"I always hoped that I would be giving it up to a wonderful lover. And for a while now, I have been trying to figure out a way to make it with you. But I wasn't sure, Derek. I had to be 100% sure."

"What?" He was shocked.

"Oh, I've been dreaming about us making love - about you fucking me - for years. And yes, that includes my tight little ass," she winked and teased him. She kissed him softly, seductively. But the seduction was long over - he was in too deep. He was caught like a deer in the headlights.

"You have?" His mind was still catching up.

She held his face then looked him in the eyes for a moment.

"Oh brother," she said softly. "You still thought you were getting over on me - trying to work on my butt a little more each time. Trying to figure out how you were going to get your little sister to give it up. When all along I have been luring you in deeper until you had no choice but to submit to me."

"Wait, what?"

Then suddenly she stood up and took off her top. Derek watched in amazement as she casually dropped her shorts, then got back on her bed, waiting.

"So, are we doing this or what?" Her face scrunched and she said sternly but playfully... "The Queen says, 'off with your clothes'" and she motioned with her hand to toss them aside.

Mindlessly, Derek stood up and undressed, totally under her spell. What else was there to say or do?

She was offering herself up to him freely once again. She was in control, and he was putty in her hands.

Amy put a pillow in the middle of her bed, then lay face down with the pillow under her waist. Her butt was lifted slightly. She turned back to look at her brother, her lover, making sure she had his attention.

"Rule number four is the same as before: if you want to fuck it, you have to eat it."

"Huh?" He was momentarily distracted by her beautiful, naked body.

"Simple. Eat my ass and make me cum. Then you can fuck me however you wish."

"Oh fuck, you're awesome," Derek said as he started to climb onto the bed behind her.

"Give me everything you have, and I'll give you everything you want. Everything you need."

The words hit him like a brick: she had said that to him on the airplane. Back when he thought he was taking advantage of her, manipulating her - to let him fuck her in the airplane bathroom.

But now the gig was up. She said he could have his way with her. But it seemed like it was the other way around. He was really her conquest all along.

--------------------

Derek was conflicted on his principles. But he's still a guy and she was naked, willing and horny.

Not only was anal on the table it was the advertised entrée. She even got him lubricant as a present. Talk about being prepared and in control.

Whether she had the upper hand or not, whether she was getting the better of him, controlling or manipulating - he wasn't sure how much it really mattered at this point.

Now the appetizer came first. Derek enjoyed eating her out just as much as fucking her. Although the prospect of getting into her ass was something new entirely.

He reached for her legs and pushed for her to spread slightly. He lay between them and nestled his nose right up to her ass. With his hands he pressed her cheeks together, getting his face smashed between her soft, warm butt.

For a few minutes he ran hands up and down her back, along her sides and down her legs.

"Mmmm," she cooed. "A nice massage."

He reached underneath her from the side, his fingers finding their way to her pussy. He slipped a finger into her. With his other hand he grabbed her butt and began to bite gently on her soft rump.

Derek licked his sister's tight little butthole. His tongue ran circles first, then up and down, back and forth. He spread her ass cheeks, then forced his tongue into her tight rear entry, pushing against the sphincter muscle. After a few seconds he felt her relax, and he was able to press deeper into her butt.

"Oh, I like that," she cooed. "I like that a lot." Amy lay there face down with her head on her arm, as she relaxed and let her brother service her.

Derek put two fingers in her pussy and twisted his hand so he could get his thumb on her clit. He massaged her from the inside, causing her to squirm. She shifted her leg and he pushed in farther until his wrist pressed up against her opening. She pushed back and impaled herself on his fingers.

Encouraged, he tongued her ass firmly. He spread her butt cheeks wider and forced his tongue muscle in deeper, holding it still and moving his head back and forth, keeping his tongue firm like a small piston darting in and out of her ass.

Her sphincter was warm and wet. Derek slipped a finger into her rectum, then a second. With two fingers in her pussy, he alternated his hands thrusting up into her. He pressed to the sides to feel her body, her skin, her flesh.

"Oh yea, that feels good," she moaned.

"I have something better in mind," Derek added. He grabbed one of her legs and turned her over. Then he pulled her legs up to his chest and grabbed underneath so he could lift her up. He folded the pillow in half, then set her back down on it.

Derek pushed her legs back towards her. "Hold please," he instructed. She complied, grabbing behind her knees and locking her fingers to secure the grip.

He lay down with his head towards her exposed pussy and began eating her out. While licking her on top, he fingered her inside and out. He smashed his face into her body, rubbing it all over her.

Then Derek traced his hands on both sides of her, from her legs to her sides, gently tickling her. Eventually he focused on her rump, grabbing, massaging and caressing her wonderful butt.

Derek slipped a finger into her ass, then two.

"Oh, fuck yea," she groaned. "Get in there, you fucking nasty little pervert!"

"Sshh!" He whispered, but she just giggled back at him.

"Let's see how quiet you can be later."

"If mom hears us, that's on you."

"Stop worrying so much," she added. "Now get back to work, PAL."

She had said it awkwardly, so he had to ask. "PAL?"

"Professional Ass Licker," she giggled again.

"Does that mean I'm getting paid for this?" He knew she was weird sometimes. But he was eating her pussy and fingering her ass and was going to fuck both places at some point tonight, so.

"If the Queen likes your service, yes."

Derek pulled his fingers out of her pussy.

"Was it something I said?" she asked, almost pouting.

But just as quickly, he jammed his top three fingers into her front, getting her attention. Then he slid the lower two fingers from the same hand into her ass - now he had five fingers inside her.

"Umph! Oh lord" she groaned, "What are you doing down there?"

"That's three plus two, it's a full house!"

With his free arm, he pushed her legs back to her chest and lifted her waist up even higher.

He moved his hand back and forth, in and out - finger fucking both her holes at the same time.

"Urgh! Fuck!" she cried.

Derek locked down on her clit with his mouth, sucking tightly. He bit and licked at her as she squirmed and groaned.

"God damn! You know what you're doing!"

"Lots of good ideas from porn," he added.

"Ideas are one thing," she moaned between breaths, but couldn't finish her thoughts. "Argh, ugh, yes!" she grunted as he continued his finger-banging assault on both her holes and ate her out.

"Finishing move," Derek pulled his fingers out, then got up on his knees to re-position himself.

He inserted all four fingers from one hand into her pussy, pulling in his thumb. He twisted his wrist as he tried to 'screw' his hand into her pussy to fist her.

"Umph! Argh!" She groaned. The width of his wrist pressed up against her pelvic bone. It was close, but he just couldn't get it all inside her. Either she was tight, or his hand was big, maybe a little of both.

So instead, he turned his wrist, letting his fingers explore around inside her.

"Oh fuck - right there!" she called out. He licked her labia and bit on her clit, causing her to go wild.

"That's it, eat me you fucker!" She screamed, grabbing the back of his head. Her legs clenched and her pussy tightened on his hand, on his fingers that were inside her

Derek went back down to three fingers, then two as he tried to fit three fingers into her ass.

"Oh god, what's that? It's too big," Amy groaned.

"If you can take three fingers all the way, then my cock will fit."

"It won't fit!" Amy cried, squealing and squirming. "Please, that's too much - it hurts!"

Derek removed the third finger from her ass, but firmly pushed two all the way back in.

"It will fit," Derek replied devilishly. "We've been working you up to this from the beginning. One finger, then a tongue, then two fingers, some more tongue..."

"Oh, ah - you fucking pervert!" Amy was lost in euphoria; she was going nuts. Her hips bucked and her body convulsed. Then she squirted on his face a little. "Oh, I'm so sorry!" she said, but he paid no heed and continued the assault.

He kept banging his fingers into her, rubbing his face all over the outside of her pussy, forcing his chin and mouth all over her sensitive lips. All the while fingering her ass, filling her up fully.

With a final fury he pushed her over the edge. She arched her back and pushed her groin up into his face. "Ahhh - I'm coming!" Waves of pleasure and pain still wracked her, as her pussy and her ass sent damage reports to the bridge.

After her body convulsed a few more times Amy collapsed, then fell off the pillow to the side. Derek's fingers in her ass slipped out, but he grabbed her hip and rolled with her. He lay beside her, with two fingers moving slowly in and out of her pussy as she continued to come on his fingers.

Amy reached back behind her with her arm, wrapping her hand behind his head and pulling him in close. She turned her head and they kissed.

"You can do that to me anytime you want, my lord" she said panting. Her body still convulsing, her breathing labored.

"Be careful what you wish for," he kissed her a few more times. "You just might get it." He rubbed his body up against hers from behind.

"I wish to give myself to you, fully." She turned her torso and faced him. "My boyfriend. My lover."

"And I want to give myself to you fully," he said naughtily. He got on his hands and knees, straddling her. Amy reached between his legs and began stroking his member, ensuring it was completely ready.

"I've been waiting for this a long time," she said. "How do you want me... face up, face down, on my side, on top?"

"All of the above," he replied. Her hands on his cock felt good, and soon he was fully erect.

"I know what you mean," she added. "I want to try everything with you. And with Mr. Penis," she squeezed his cockhead multiple times.

"Let's start with you on your stomach. I can get deeper into you that way."

"I love getting fucked from behind."

"And in the behind?" Derek lifted a leg allowing her to turn over, then he straddled her rump, resting his cock between her ass cheeks.

"I don't know. But I've loved when you fingered me while you ate me out, that's for sure. I guess we'll find out, won't we?" She smirked and looked back and him, hungrily.

Derek began rubbing up against her butt, and Amy instinctively shifted to get comfortable.

He reached down and guided his cock with a hand between her legs. He slipped it into her warm pussy.

"That's the wrong hole, silly."

"Just warming up," he replied, thrusting into his sister underneath. He pumped into her a few times.

"That feels wonderful. But I'm all warmed up now, thank you. Good and relaxed," she said with pleasure. "Oh - rule one is satisfied!"

"Nice! Now, rule two is to be well lubricated." He pulled out to reach over for the lube on her nightstand. He put a dollop on his finger and put just the tip into her bum, getting her sphincter wet. Then he put some more on a finger and slid that all the way up into her butt.

"Umph, oh my!" Amy exclaimed. "That's not so bad! Is that it?"

"No, just a finger, getting you ready."

"Oh, OK. Just checking."

"Are you OK?" He had to ask.

"You better give it to me good, or I'll be sore."

"If I do give it to you good, you will be sore."

"The good kind of sore," she giggled.

"Rule three: you will let me know if it's too much, and at any time if you say to stop, we're done."

"I think I can take it," Amy replied naughtily. She was determined to go all the way with her lover.

"Fingers are one thing," he replied and let the thought complete itself.

"How many?"

"Only one at the moment. Ready for two?" he asked playfully.

"Oh, um, yea" she conceded that she hadn't been fully tested.

"Yeah?" He asked, spreading her cheek with one hand and slowly inserting two fingers all the way up into her behind. At the tip is one thing, but up to the knuckles they get much wider.

"Umph! Oh god! Owww," she tried to squirm away.

Derek pulled his fingers out, got some more lube on them, then re-inserted them back until he couldn't push them in any farther.

"Is that too much?" He worried that he had gone too far, too quickly.

"No! Yes! I don't know," she moaned and groaned. "It's really tight."

"This is just two fingers," he confirmed as he moved them up into her again.

"Oh, uh! I'm worried your big cock might not fit!" she talked nasty and dirty, knowing he liked that.

Derek fingered her ass with slow, rhythmic movements. He reached under her to play with her pussy.

"Yeah," she cooed. "Work me like that for a bit." He had two fingers working in and out of her warm pussy, and two in her tight ass. Her pussy felt great, and she moved her body in response.

After a few minutes he positioned himself up against her, inserting his cock back into her pussy. After a few pumps in deep, he held it in place. Then he slipped two fingers back into her ass. He lay down on her, his hand between them - his body forcing his fingers deeper and up into her back side.

"Oh, yea," she moaned in pleasure. "Fill me up!"

Derek began thrusting into his sister's pussy with long, slow, deep motions. He held his fingers in place up her ass.

"I have an idea," he whispered between kissing her neck and sucking on her earlobe. "When I'm about ready to cum, how about I just put the tip in?"

"No way," she said immediately, defiantly.

"Too much?"

"No - I mean, no way you're only putting the tip in. I want it all!"

"You do?"

"Fuck yea. This is so nasty and naughty. Everything you do to me feels so great... And I've been wanting this for so long. No way are we settling any 'just the tip' nonsense. I've worked too hard for this!"

"I was just trying to ensure we take good care of you, you know, on the receiving end."

"Oh, that you do," she moaned again as he kept pumping into her pussy with his hard cock. "I have a better idea. How about when you are about to cum, you cram it all the way in."

"All the way, really?"

"Yea, as in, balls deep. I expect you to cum in my ass, big brother!" Her dirty talk was getting him excited, and she knew it. She pushed her hips back against him and he thrust back into her in response.

"I thought there were no expectations?" he asked playfully.

"Let me be one hundred percent totally clear. I expect you to make love to my tight, virgin ass," she said naughtily, urging him on. "Even if it's too big, even if it hurts. I want you to finish inside me. Got that?"

"Fuck yea!" Derek exclaimed. He worked her another minute, grinding against her body, fingering her deeply.

Sensing it was time, Derek removed his fingers from her butt. He reached down and guided his cock in hand up to her backside. His thumb was the positioner, and he pushed it in a little.

"Is that your cock?" Amy asked happily.

"My thumb. Just lining it up."

He could hardly believe it - he was really about to fuck his sister's tight little ass, and she was wanting this just as much as he did.

"Ready?" He paused for a moment, just to be sure.

"Go slow," she requested. "I want us to remember this for a long time." She reached behind with her arm, grabbing the back of his head as she arched her back.

"Oh, you can be sure of that. I've been dreaming about your sweet little ass for years."