View Full Version : "Just The Tip" with Olivia Holt

09-03-2015, 09:26 AM
Just The Tip
With Olivia Holt
Written by TPG
CODES: MF, inc, handjob, anal
DISCLAIMER: This FICTIONAL story was written for entertainment purposes only.

http://1.t.imgbox.com/g983LNJx.jpg (http://imgbox.com/g983LNJx) http://4.t.imgbox.com/K1m89DwK.jpg (http://imgbox.com/K1m89DwK) http://8.t.imgbox.com/gADHpOSH.jpg (http://imgbox.com/gADHpOSH)

It wasn't the first time Olivia had knocked on my bedroom door in the middle of the night, but unlike previous visits I could tell something was wrong.

"Cade, are you awake?"

"—what's up?"

The door opened to reveal my sister, who was scantily clad in her sleep attire, which consisted of an over-sized shirt, and high cut panties. I literally gulped when I realized how inappropriately dressed she was.

"Err, Liv—" I said while trying not to sound alarmed. "Aren't you cold?"

"Listen. You're probably going to think this is stupid." she said while shutting the door behind her. "—but would you mind if we just hung out for a few minutes?"

While my initial reaction was to snicker, I knew that ever since her break up with Luke, Olivia had been going through a tough time. In fact she hadn't taken the bust up well.

"I don't know. It's pretty late."

"I won't stay long, I promise."

I still wasn't convinced, particularly since I suddenly felt the need to put on a shirt.

"—don't worry about getting dressed." she said as she crossed the room. "I just want some company for a few minutes."

"Fine with me. But you know we'll get in trouble if mom catches you in here."

Olivia rolled her eyes as she climbed into bed.

"Scoot over."

Considering my bed was just a single-sized mattress, there wasn't anywhere for me to go. We lay in bed for some time before I asked her if she was okay.

"I don't know." she shrugged. "I guess I'm feeling a little lonely lately."

"—because of the breakup?"

"We were together for a really long time." she explained. "It still feels weird being by myself. It's only been a few days and I hate it."

"Yep. Kind of sucks that it didn't work out." I replied. "Just don't make this a regular thing. I'm not really used to sharing my bed with anyone."

Olivia squirmed a little closer to me, and placed her hand on my arm.

"I won't." she giggled. "But can you do me a favor and play with my hair?"


"Luke used to play with my hair to help me sleep."

"Err. I know. But I'm not Luke."

"Come on. Please. Just for a few minutes." she claimed. "—and then I promise I'll leave."

I reluctantly obliged and proceeded to play with her hair as she now lay beside me in bed.

"Considering all the shit you've gone through lately, I think you're doing well sis." I told her.

"Except for the fact that I'm single, and lying in my brothers bed!" Olivia said, her voice barely loud enough to hear.

I reached over and gently traced the side of her face with my fingertips, brushing a few strands of hair away from her eyes. Her head tilted almost imperceptibly toward my hand. After a moment she finally let her gaze meet mine.

"Don't worry sis. You'll find someone new." I assured her. "There's no way a girl like you doesn't find a boy. You're too hot and talented to be single."

"Aw. Thanks, Cade." she pouted. "I wish I could believe that. But right now I'm just a mess. My mind is all over the place."

I started to pull my hand away, but Olivia stopped me and guided it back. I cupped her cheek in my palm while she closed her eyes and cooed. Apparently she just wanted some physical contact, and I didn't mind giving it to her.

After a few minutes she nudged closer so that we were essentially snuggling in bed. I invited Olivia to lean her head on my shoulder, then I put my arm around her and covered us both with the blanket.

She let out a small sigh and cuddled up to me.



"Would it be okay if I stayed here tonight."

There didn't seem to be anything too odd about her request at first. I guess I didn't expect her to be as depressed as she was. It actually made me feel guilty.

"Is that what you want?" I asked while massaging her scalp. "You wanna sleep here with me tonight?"

"I know it might sound weird. But your bed's so cozy and we wouldn't even have to be that close."

"Fine. Stay. " I replied. "But I should probably put on a shirt—"

"Meh. Don't bother!" Olivia interrupted. "It doesn't bother me at all. Unless of course it makes you uncomfortable."

"Not really." I lied, as we just lay there in the dark casually chatting while I stroked her hair.

"Mm. This is nice. I kinda like this." she added while running her hand over my chest.

"You do?"

"Is that weird?"

"Of course not." I lied again.

"Mm. That feels so good." she purred softly. "You've obviously done this before."

"I aim to please."

"If you keep this up you're going to make me fall asleep in your arms Cade."

"That's the idea dummy."

"Hey. You can't speak to me like that." she giggled. "I'm older than you."


I was a little confused when I woke up the next morning. It seemed we had managed to stay mostly on our own sides of the bed during the night, but her sleeping position was decidedly undignified.

Olivia had kicked the blanket down enough that her tummy and panties were exposed, and judging by the small wet patch on my pillow, she had also drooled a little in her sleep.

I was pretty sure one of her legs was actually dangling off the side of the bed, though the blanket made it difficult to see for certain. I rolled onto my side facing my sister and just watched her for a minute.

In fact it didn't take long to notice something I had missed at first glance. It seemed her shirt had somehow gotten pulled tight across her chest, so tight in fact that I could clearly see the faintest little bumps of her nipples through the material.

Once I realized they were visible, it was hard to look away. It was hard to know where I stood, morally speaking. I wasn't supposed to be checking out my sister, that was pretty much a given.

Then again, as long as she didn't catch me staring there couldn't be any harm in it.

Eventually I decided I should try to fix her shirt. I was pretty sure it was stuck underneath her, and hopefully it would come loose with a simple tug. I figured if I was able to free her shirt then it would both cover her tummy and sit more loosely across her chest.

I tried pulling on her shirt from my side, only to find that it was caught on the other side instead. That made things more difficult. Short of getting up and climbing out of bed, I wasn't sure that I could dislodge it without disturbing her.

I finally reached over as far as I could and tugged gently, but to no avail. All this accomplished was to wake her.

"What are you doing?" she murmured sleepily, her eyes flicking open.

"Just fixing your shirt."

"uh-huh." Olivia smirked. "Sure you were."

Surprisingly enough, my sister didn't sound like she believed me, but she also didn't sound upset. Instead she stretched out lazily, once again drawing my attention to her chest and those two pebble like nipples.

"Wow Cade." she yawned. "—trying to cop a feel while I'm asleep eh?"

" I didn't!" I said, trying not to sound defensive. "I was just...your shirt was all weird. It looked uncomfortable."

I pointed at her torso as though she might not have known where to look. She didn't so much as glance down at herself.

"Meh. Whatever. I don't care." she scoffed a minute later. "It's probably the most action I've had in weeks."

"But I really didn't—"

I stopped mid-sentence as I detected a crack in her otherwise neutral expression.

"Wait a minute. You're just messing with me."


The smile that had been threatening to break finally did.

"Okay, yeah I am." Olivia giggled. "I'm just fucking with you Cade. Sorry."

"No you're not."

Olivia laughed out loud.

"—I'm sorry, but you should see your face right now."

I reached over and pulled on her shirt, this time with a lot more force. The part that had been trapped beneath her came free, and I straightened it out so that she was covered properly.

"So." Olivia said while glancing at the time. "—do we get up, or do we choose to be lazy for a few minutes."

"Well I don't really want to get up, but you should probably go back to your room before mom catches you in here."

"I gotta admit—" she said while stretching again. "You're bed is really comfortable. Way more cozy than mine."

"Fine. Suit yourself." I quipped as I rolled out of bed and decided to take a shower.

Living with a Disney star like Olivia Holt, taught me the value of grabbing the bathroom when it was free. Unfortunately, Olivia didn't seem too concerned about getting out of bed and instead rolled over and got more comfortable.

"Mm. I could get used to this bed—" she purred while settling in.

"God damn it sis." I whined as I grabbed a change of clothes. "You're going to get us in trouble."

But just as I was about to turn for the door, I looked back at the bed and couldn't help but stare at her long smooth legs and her teenage ass in those high-cut panties.

"Wake me up when you get back."

"Fine. Stay here." I said while giving her teen ass one last look. "But if mom catches you in here it's your own fault."

"—and don't hog all the hot water!" she added as I walked into the hallway.

I assumed sleeping with her would be a one-time deal and didn't give it much more thought. However, I realized that wasn't the case when Olivia crawled into my bed again the very next night.

In truth, I kind of liked having her next to me as I fell asleep, and waking up beside her in the morning was nice too, so I allowed us to slide into a new routine.

We didn't sleep together every night, but it became fairly common for us. At least two or three times a week. My only real concern was that if we kept it up, someone was bound to find out sooner or later.

I was mostly worried about dad finding out, since he usually woke up earlier than us. I wasn't even sure what his reaction would be, and I didn't want to find out.

Still, despite all the risks Olivia and I continued to share my bed. In fact a month into this new arrangement, I awoke to find us in almost the exact position we went to sleep, essentially spooning each other in the middle of the bed.

At first I wondered if we had spent the entire night curled up together, until she shifted slightly and I realized she was already awake.

"We probably shouldn't do this anymore." Olivia whispered.

"Huh. If you say so."

"People might think it's weird." she continued as though I hadn't spoken. "—that I love sleeping in my brothers bed."

"Who says anyone has to know." I replied. "Besides. Can't we just lay here without feeling guilty?"

"I guess."

"Is it because I like to play with your hair?"

"It probably wouldn't seem so bad if we kept our hands to ourselves." she added.

"If you don't want me to touch you anymore, than fine." I answered. "If that's what you want. We'll keep our distance."

Olivia glanced over her shoulder for the first time.

"Come on. You know that's total bullshit." she grinned. "We both know we couldn't do that."

"You're probably right."

"Besides. You'd miss me too much." she giggled.

Olivia and I lay there on the bed spooning for sometime, close enough to almost be cuddling. Admittedly, despite what we discussed we didn't keep our hands to ourselves, but for the most part the situation remained innocent enough.

I guess we both just got into the habit of me playing with her hair, and brushing my fingertips up and down her arm to caress and tickle her. But just because I knew nothing was going to happen, didn't mean I could keep my mind out of the gutter.

When I started getting hard I didn't give it much thought, since there was just enough space between us that I assumed Olivia wouldn't notice. That only held up until a coincidental movement of her leg brought her ass into brief contact with my erection.

I had hoped she hadn't realized what she had bumped into, since she didn't react at first, but I hoped in vain.

"Cade." she said softly. "—are you hard right now?"

There didn't seem to be much point in lying, not after the way things had been going between us lately.

"Yeah I am." I blushed in shame. "Sorry. It's not you. It's just morning wood I guess."

"Oh. Okay. Sorry."

I smiled a little at the apology.

"You don't need to be sorry."

"But it's kinda my fault, isn't it?"

"I suppose it kind of is. It's not really a bad thing though."

There was a long pause before she spoke again.

"Do you...actually, never mind." she said.

"Do I, what?"

"Um. Do you think it'll go away soon or, are you gonna need to take care of it?"

"I'm not really sure. I guess I'm still getting used to waking up next to a hot girl in my bed."

"Yeah." she giggled. "I guess so."

Olivia let the subject drop for a few minutes, but I sensed it wasn't over. Particularly since my erection didn't seem to go away. In fact it only seemed to get harder with each passing minute, no thanks to her fidgeting around and "bumping" into it again and again.

"Oops. Sorry."

"Yeah. I bet you are."

As I tried to distract myself from my own thoughts, Olivia reached down with no warning and gently squeezed the bulge in my shorts. I drew in an audible breath at the unexpected contact and looked at her for an explanation.


"Sorry. Just checking." she smiled.

"You could have asked."

"uh-huh." she mumbled, clearly not paying that much attention to what I was saying.

I felt her fingertips on my cock again, caressing the outline of my penis through my boxer briefs. I didn't know what she was up to so I didn't say anything at first, but she didn't show any sign of stopping.

"Err. What are you doing?" I finally asked.

"Shh. I'm helping." she claimed. "Fixing the problem."

"But you don't have to—"

"Shh!" she said more firmly, while squeezing my cock in her hand and reaching down to massage my balls.

The action almost took my breath away.

Given no say in the matter, I simply lay still and let my sister do what she wanted. For a while she just toyed with me, with no sense of urgency in her movements, before she finally curled her fingers around my shaft in a more standard grip, only backwards.

Her hand was decidedly softer and more delicate than mine, and it felt good just to have her squeezing me. It only got better when she began stroking it up and down, in a slow, smooth rhythm.

Again she appeared to be experimenting and gauging my reaction, more than she was actually trying to get me off, but that didn't mean she wasn't making any progress on that goal.

"How's that?" she asked in a teasing voice.

I arched an eyebrow.

"You can't tell?"

"Maybe I just want to hear you say it."

"Alright, it feels good." I praised. "Really, good."

Olivia nodded as though satisfied with my answer, and shortly after that she increased her tempo significantly, adding more pressure to her grip as well.

Whatever impression of inexperience she may have given earlier was soon gone. It had obviously been an act, intentional or otherwise, because she definitely had some idea of what she was doing when she put her mind to it.

"—Liv." I finally panted into the back of her neck, as my cock throbbed inside my boxers.

"Mm. Don't do that." she purred back. "Don't breathe on my neck. That drives me crazy."

"Sis—" I moaned again, this time making sure to press my lips behind her ear. "Don't stop."

At this point we were both panting and squirming wildly on the bed.

"Does this help." she whispered hotly over her shoulder. "Are you gonna cum soon."

I responded by brushing her hair to one side, and kissed her neck. Olivia cooed to the action and leaned her head to the opposite side, exposing more of her skin to me, which I took as a sign to continue.

I soon worked my lips from the nape of her neck, all the way down to the side of her throat where I began to give her a juicy love-bite.

"Ugh. Wait. Don't leave any marks!" she gasped as I licked and sucked my way up to her ear.

Her flesh was soft and salty, and covered in goosebumps.

"Mm. We should probably stop." I heard myself think out loud. "—in case mom walks in on us right now."

"I know that, and you know that." she panted back. "But if really want me to stop say it, and I will."


Fact of the matter was, there was no way on god's green earth that I was going to do that. Instead my muscles tensed as my sister's hand stopped what it was doing, and slipped inside my boxer briefs to grasp my cock directly!

I felt her delicate fingers encircled my shaft, gripping it tightly enough to cause precum to leak out the tip. She immediately tightened her grip and began stroking it.

Olivia didn't have the same experience I had at getting myself off, but that hardly mattered. As much as I hated to admit it, it was the mere fact that it was my sister who was stroking me that actually turned me on.

After all, Liv was a bonafide Disney star on TV, who was also on the verge of breaking out with her singing career. God only knew where she'd end up, or how famous she'd become in just a few short years. And yet, here she was jacking me off in my own bed! ...this was the stuff of dreams.

Olivia gradually became more sure of herself as she continued to jack me off. The way her fingers gripped me had been a little tentative at first, but that changed as her confidence grew.

I eased my hand around her body to caress her hips and belly, before I finally slipped my fingers underneath her top to cup one of her bare breasts. I couldn't believe the softness of her boobs, and squeezed her firmly enough to make her purr.

"Mm. Cheeky." she smiled, as we now both openly fondled each other on my bed.

"You're not the only one who can tease."

I then spent the next few minutes trying to unbutton her shirt with two fingers, and ultimately achieved my goal, leaving her to lay completely topless beside me.

With her breasts unfettered, I now mauled and groped her tits at will as she stroked my cock in kind. It was at this point that she leaned back to say something that I suddenly knew what to do, and without warning I kissed her on the lips!

I wasn't entirely certain why I did it, or even if I should have, but Olivia didn't object.

In fact she kissed me back with just as much passion as we continued to spoon each other on the single bed. For a while that's about all we did. We just kissed and humped each other while I played with her tits.

When I ultimately glanced over to look at the time I was a little surprised to see that we had been sucking-face for almost twenty-five minutes.

"—this almost feels like the real thing." I remarked at one point as I continued to grind my cock against her ass.

Olivia bit her bottom lip and nodded in agreement.

I'm not entirely sure what her panties were made of, but the frictionless fabric wasn't doing much to satisfy her, and a small amount of frustration began to creep over my sisters face.

I moved my hand across her bare hips and down to the top of her panties, then dipped my fingers inside. Olivia's frustration vanished as soon as she felt what I was doing.


Her slit was already wet, though I didn't examine just how wet it was at first. Instead I gently dipped two fingers along either side of her mound, teasing her a little while smearing her wetness all around.

"Cade. Wait." she hesitated.

I quickly silenced any qualms she might have had by pressing my lips to the back of her neck. This really seemed to subdue her, and she squirmed back against my cock as my fingers now explored and probed her cunt.

When she appeared to get a little too excited by my "handy" work, I changed tactics and withdraw my fingers. This naturally drove her crazy with desire, until she finally grabbed my hand and shoved it deep inside her panties.

"Stop teasing me." she hissed.

I grinned smugly to myself as it only took a small amount of force to ultimately plunge two finger into her damp pussy, and just like that, I was finger-banging my famous sister.

Olivia seemed perfectly content to let me do what I wanted. Her eyes were closed, but her lips twitched every now and then when I did something she really liked. She particularly liked it when I'd circle my index finger around her juicy, pea-sized clit.

She didn't remain completely passive for too long though, as her hand found its way to the waistband of my boxer briefs where she seemed intend on pulling them down.

"Ugh. Take them off." I heard her hiss, as she hauled my underwear down to my knees and freed my cock.

She now had unfettered access to my erection and jacked me off enthusiastically, throwing off my concentration, as her fingers cupped my balls before her thumb massaged the tip of my bell-end.

At one point I was literally humping my hips into her fingers and fucking her hand.

"Oh god, Cade—" she moaned breathlessly. "You're so hard. I want you so bad right now."

"Me too sis."

"—but we can't." she trailed off. "Even though we really, really want to."

"We can't huh?" I repeated.

"This is wrong." she whimpered. "So, so wrong."

"I don't care!" I told her as I buried my fingers to their second knuckle and filled her pussy with two digits.

"If this is so wrong, then why are you so fucking wet!" I purred in her ear. "You're dripping wet, Liv. Dripping. Wet."

With my hand already inside Olivia's underwear, it was easy enough to haul them down her legs. She shifted a bit to help me take them off entirely, leaving her completely naked on my bed.

I felt Olivia's hand on my cock again as I scooted in close behind her, and helped guide me rod towards her glistening sex.

"Cade. We can't have sex."

"I know. But we can still mess around." I replied. "We can still hump-n-grind and shit, right."

"I know but—"

"Look. We won't have sex." I insisted. "I swear."

"You have to promise me Cade." Olivia persisted. "You can't put it in."

"I promise!" I quipped back.

"You can't put it inside me." she repeated again. "—but I'll let you rub it against my pussy."

Sweeter words had never been spoken.

Despite her words her body was more than eager for sex, and as soon as I made contact with her cookie our instincts took over. Olivia moaned and reached back to place her hand on my ass, holding us close together as we now moved our hips in unison while I rubbed my cock against her pussy.

When my lips made contact with the side of her neck, this combined assault stirred something deep inside of her, and I felt her grind her ass back against me, almost allowing my bell-end to enter her for the first time.

"Oh. Shit." I gasped to the action. "—so close."

"Ah. Fuck." she hissed back in a combination of disappointment and frustration.

But despite this "slip up" we both resisted the urge to have sex.

Instead I pulled back slightly and continued to rub the very head of my cock along those velvet-soft lips, all the while as she continued to hump back against me, almost tempting fate.

"Fuck that feels good." I groaned from behind her. "Liv. Please."

"Ugh. Don't stop." she grunted. "Keep going."

"Liv. Please. Just let me put the tip in."

"What. No! Don't you dare Cade." she panted, despite still grinding back against me. "I told you, we can't have sex!"

"—just the tip. I swear. Please." I almost begged. "Just for a second. I promise. Just let me see what it feels like."

There was a long pause before Olivia conceded.

"Ugh. God. okay-okay!" she mewled. "But just the tip!!"

"Fuck yeah."

"—and only for a minute! Do you understand me Cade."

I thanked her by kissing her hard on the lips, and distracted her briefly as I scooted up as close to her ass as possible, and lined up my cock.

My sister literally melted in my arms as we kissed passionately, while I slowly pushed forward to enter her for the very first time. In truth, Olivia was so wet that it almost felt like sliding a hot knife through butter.

My lips were immediately back on her neck sucking her skin, as I gave one final thrust and buried my helmet within her snug walls. Despite all her threats and warnings, Olivia capitulated completely, and felt me push in all the way.

Her pussy seemed impossibly tight at times, yet never failed to allow me deeper access until I bottomed out entirely inside her teen pussy. Liv gave me an extra tight squeeze as I reached her depths.

"Fuck." she cussed audibly, before her mouth was on mine.

She kissed me in a way like she had somehow learned how to go without breathing in the past few seconds. I, however, still needed air and had to pull my head back to get out of her reach.

"Ugh. Cade." she whimpered erotically. "—just the head?"

"I lied."

I soon discovered that an upside of fucking her in this spooning position, was that it allowed me to place my hand on her shoulders and push her forward, permitting her ass to jut out and grant me greater access to her slick pussy.

When I grabbed her hips and proceeded to fuck her at a steady pace, she simply moaned and glared back at me in a mishmash look of love and lust.

"Ugh-baby. Yes." she sighed softly. "Right there Cade. Don't stop."

I had no intentions of stopping, and have no idea how much time passed as we screwed in this delectable position on my bed.

My hips never stopped rocking against her the entire time. At one point I pulled her back into a deep kiss as she arched her back sharply while still connected by our genitals.

I then proceeded to work my way into her with short, steady strokes. In truth I had only had sex a handful of times, but god knows I didn't lack any enthusiasm.

Despite my inexperience, I hoped that my passion and ferocious energy would be enough to satisfy my older sister, which apparently did.

Olivia's hips now slammed back against me with renewed zeal. Pretty soon my balls were slapping audibly against her cunt as she took all seven inches of me again and again.

"Fuuuck. Cade." she bemoaned. "—harder. ohmigod. Yes. Give it to me. Gimme that fat cock!!"

Every inch of my dick was buried inside her. In fact her muscles contracted rhythmically, squeezing me tight. I couldn't believe how good it felt just being inside her, let alone how incredible it was when I moved back and forth.

Her tight teen pussy felt like warm apple pie as I pulled partway out, only to slam back in again. I experienced pure bliss as I increased the intensity of my thrusts, and fucked her within an inch of her life.

Olivia reached back to run her nails across my thigh as I slowed down the pace and proceeded to make slow, sweet love to her from behind.

At this point we were both sweating profusely, and her pussy was so wet that we could actually hear it sloshing with each upstroke. The sound alone was extremely embarrassing and yet exciting for her.

"Oh. God." she blushed as I pounded that sopping minge again and again. "Oh God. Cade."

Caught up in the moment, I then slapped her ass sharply with my hand, causing her to gasp out loud and gulp in a huge mouthful of air. Repeating the action only seemed to turn her on.

"Ugh. Yeah. Spank my ass Cade." she growled back. "—smack it. I'm such a bad girl."

"Yeah you are." I grinned. "Just listen to how wet you are Liv."

Despite my rough handling, or maybe because of it, I could actually feel her arousal growing, making my cock slicker and easier to take inside. Soon she was moaning like a whore as I drilled her incessantly.

A minute later Olivia finally came, and the intensity of her orgasm rocked her to her very core. My sister shuddered violently beside me before it left her trembling, her legs shaking as I continued to pummel her numb pussy.

"Fuck-Yeah. Fuck-Yeah. Did you just cum!" I smirked smugly to myself.

I took this opportunity to catch my breath, and reached over to the side of my bed to produce a small bottle of lube. Olivia was so lost in her own world she didn't even realize what I was doing till it was too late.

I doubt she even knew what planet she was on.

I took hold of her hair and snapped her head back, causing her to yelp and arch her spine. This pushed her hips back, forcing more of my dick inside her. She then felt me reach down and open the tight cheeks of her ass with my fingers, revealing her tightly puckered asshole.

Olivia jumped when she felt the slippery lube hit her skin, partially because it was cold, but mostly because of what it meant. It was only now that she realized that I intended to fuck her ass!

"—Cade, wait."

"Sis. I want your ass." I growled into her ear. "Let me just stick the head against your ass."

"What! Cade. No." she objected. "I don't like that."

"Have you done it before?"

"No. But—"

"So how do you know you won't like it?"

Olivia suddenly jumped as I slowly pressed the head of my cock against her tiny sphincter and impaled her shit-pipe.

"ohmigod. Cade. Wait!" she shook her head in panic. "—we can't. You're too big!"

"Just relax and open your ass to me." I whispered into her ear.

"Cade, please."

"Please Liv. I want this—" I moaned back. "I want this so bad."


"How fucking sexy is this. Look how dirty you are right now...with your brothers cock in your ass!"


Olivia shook her head furiously but made no attempt to stop me. In fact she sucked in a breath, trying to prepare herself for what was to come, while trying not to cry out.

At first she felt a blunt, insistent pressure against her tight opening. Then she began to open up, allowing the head of my shaft inside. She gasped as the head carefully popped past her rim, and thought she would black out the pain was so intense.

My sister groaned as she felt the head of my cock slowly open her asshole wider, giving me access to her hidden depths. Inch by agonizing inch I gradually entered her, grunting with the effort, despite the lube.

"Oh God. Your ass is so tight sis." I murmured from behind her.

Olivia's muscles squeezed around my shaft, trying to eject it from her anus, but I held the cheeks of her ass tighter, sawing my hips back and forth in response to her efforts.

"ohmigod. ohmigod." she chanted. "—I can't believe we're doing this."

All the while as she moaned I kept swiveling my hips back and forth, thrusting my now swollen cock deeper into her bowels.

I don't know what turned me on more, the way her asshole twitched and gaped open on my in-stroke, or the way her sphincter seemed to grip my cock on its outward journey.

"Ugh. Cade." she grieved into the pillow. "Slow down. Please. Not so deep. You're in my ass!"

"Look. We're doing it sis. You're taking it." I almost boasted. "I'm fucking your ass. You're sweet, tight, little ass."

Pulling back, then thrusting farther in, I buried about half my length inside her. Then I began to saw back and forth, quickening my pace.

Slowly, as the lube coated the inside of her rectum, her sphincter muscle relaxed, and it began to be a lot less painful, allowing me access to her deepest, most private, entrance.

"ohmigod" I hissed with glee. "You're ass feels so good. You're going to make me cum Liv."

"Please. Just do it! Just cum." she hissed over her shoulder while biting her bottom lip.

"You don't like it?"

"I do but—" she admitted. "Just hurry."

"So you do like it huh?" I grinned. "Well when I'm done fucking your ass, I'm going to shoot my load all over it, then I'm going to make you suck my dick clean!"

"Unngh. God." she groaned at the notion.

The thought of sucking my dick after it had been in her ass clearly repulsed her, but we both knew she wouldn't refuse, not after the way she had given me free rein to do anything I wanted.

"Fine. I don't care Cade." she answered back. "Just hurry up before mom and dad wake up."

This was all the permission I needed.

It was at this point that I finally felt brave enough to propose a new position, and directed her to roll onto her stomach. Thinking quickly, I placed one of the pillows underneath her belly which left her lying on my bed with her face down and her ass up.

"Don't move." I told her, as I mounted her from behind and stuffed my hard cock into her asshole again.

Olivia gave a low moan of pleasure before she glanced over her shoulder.

"Ugh. Hurry up and cum."

I raised my head slightly to look at her. I could see all the passion and intensity in her eyes. This was a day we'd never forget.

"Just gimme another minute."

"Come on Cade." she teased back. "Is that all you got? —fuck my ass already and cum."

"Oh-God." I moaned to her words. "Don't even say it like that."

"Come on little brother." she encouraged. "Shoot that hot fucking load all over my back baby."

Just hearing this tone from her was enough to push me over the edge. But when she reached down with her free hand and began to rub her clit, I just about lost it.

At long last she finally heard me groan, "Oh fuck Liv. I'm going to cum!"

In an instant I pulled out of my sisters shit-hole and fired my wad directly across had her flawless butt, sending further jets all along her spine and back, some of which even struck her hair.

"Ugh. Jesus!" she gasped as I covered her body in hot ropes of spunk. "That's so nasty."


"—if you think I'm putting that thing in my mouth you're crazy." Olivia sneered while dripping in semen.

"Come on sis." I pleaded. "Don't be such a prude. Just give it a quick suck."

"Prude!" she repeated. "Cade. I just let you fuck me in the ass. No one's ever done that before. Not even Luke!"

"Hey. You had that coming. You had that coming for a while."

"Ugh." she rolled her eyes. "I need a shower."

"Really. Can I come?"

"Jesus Cade. Haven't you had enough?"

"Not even close sis. Not even close."


09-03-2015, 10:01 AM
I knew this would be great just seeing those tags at the top but holy fuck that was awesome. Really liked the slower build up to it and you continue to be great at the dialogue stuff, Cade is a lucky guy.

And now I think I'll join Olivia in that shower, lol.

09-03-2015, 10:21 AM
Totally just filled the cup.

09-03-2015, 12:49 PM
Mmm yet another wonderfully sinful story from the master of sibling wincest stories. Amazing like always.

09-03-2015, 02:54 PM
Officially my favorite Liv story on the site now.......more more more please. Hoping for a chap 2

09-04-2015, 01:30 AM
great story waiting for chapter 2

09-04-2015, 04:43 AM
I agree there needs to be more of this. Great work.