Being Helpful Pt. 02

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Xylander makes his sister cum to cure her period cramps.
5.8k words
4.61
49.7k
90

Part 2 of the 3 part series

Updated 06/09/2023
Created 02/26/2019
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Story includes incest, cum swallowing, panty sniffing, oral sex, exhibitionism, pussy hair, blood, tampons, menstruation, ass licking, and pee. Just a heads up.

Since the first time my sister and I made each other cum, I wished we could do it again. But I was too scared to initiate anything like that with her. After all, I had only brought her to orgasm as a remedy to her menstrual cramps and she had sucked me off to thank me for said medicinal orgasm. Sure, it was the hottest, most intense orgasm I had ever experienced and I didn't even have sex with her, but I was sure our behavior that day was to serve one purpose exclusively. Either that or I had convinced myself of this as a way to chicken out of trying to fuck her. Rejection would be absolutely devastating to our relationship as siblings and I couldn't risk that. A solid excuse for what we did kept me able to interact with her as before.

But that just kept me looking forward to the next month, when she was on her period again. I counted down the 28 days for her to begin menstruating again so that I could help her. And even when the day came, I was extremely nervous to ask if I could help her in that way again. I would need a sign, a reason to even ask if I could help. I couldn't just pop into her room and say 'hey, I see you're on your period. Need me to eat your pussy?'

Now, it would seem cruel for me to be waiting for my big sister to be doubled over in severe menstrual pain so I could lick her pussy again..., but I was waiting for my big sister to be doubled over in severe menstrual pain so I could lick her pussy again. And even to offer my help in that situation would require all the courage inside me, and then some.

The first day of her period she casually told me that she had come on. She didn't know I had been counting the days. The rest of the day was normal but that night I made my mind up that I would wake up in the morning, and if she seemed to be in pain, I'd offer to help her and hopefully it would follow as expected or, should I say, as I hoped.

When I woke up the next day I went to the bathroom to pee and brush my teeth. When I left the bathroom I heard Octavia yell out, "Xy! Xylander!"

"Yeeesss?" I called back, my heart beginning to flutter.

"I need your help. Could you come here for a minute, please?"

I walked into her room only in my grey boxer briefs and found her lying on her belly in bed, wearing nothing but a pair of plaid green panties and her tan knee socks. "Yeah?"

"Could you rub my back? I'm cramping really bad." she whined, turning her head to look at me.

"Y- yeah," I said nervously, the moment I had waited a month for was (probably) finally here.

I got on the bed beside her and put my hands to use on Octavia's lower back like before. My nervousness starting to fade, I looked down at my sister's plump ass. It looked so healthy and round in her panties. I then surveyed the rest of the flesh in front of me. Her curvy hips and the slight puffiness in her flawless ivory skin. I looked down at the space below the panties above her high socks, at her beautifully stout thighs, my cock starting to harden in my underwear.

Feeling a bit more bold, I pushed her legs apart some and set my knees between her fleshy thighs. "Trying to get comfortable," I offered as an excuse.

"Mhm," she simply hummed her approval. When I moved, I noticed I had my knees on a dark red towel. She must have laid it out before I came in, which means she didn't want to get any of her blood on her sheets, which meant she expected to be removing her panties at some point. I got excited, almost certain we wanted the same thing.

I slowly worked my way down her back until my fingers just barely danced along the lace band of her cotton panties. When no objection was made I grew bold and went lower, right below the band and right at the top of her full posterior. I began to massage back and forth from that point up to the middle of her back, keeping a pretense of a semi-innocent massage. Still, no objection was made, only light hums. Every time I descended back down to her ample ass, I took more liberty with it, caressing more of it for longer periods of time. Eventually, I stopped all pretense and a back rub because an ass massage.

"That feels good," my sister said, encouraging me to continue. I took big handfuls of her soft bottom and kneaded the panty-clad flesh. There was more than enough ass to overfill each of my greedy hands as I squeezed and mashed and caressed and massaged the bouncy globes. I put my thumbs up the leg holes of her panties, desiring to feel the skin of Octavia's ass on my own skin as I rubbed her. After a while the panties became distorted as I pushed them upward, essentially giving her a wedgie and exposing half her ass cheeks.

Octavia giggled. "Just take 'em off, Xy."

I chuckled and scoffed. "I thought you'd never ask."

"Yeah, right."

I stepped back onto the floor after hooking fingers into the band of my sister's panties and dragged them down as I recoiled. Octavia put her legs back together so I could get them off her feet. I sniffed her warm panties without shame, enjoying the faint musk of her more private crevices. "Are you smelling my panties?" my sister asked with obvious amusement in her voice.

"Yeah," I chuckled and took a bigger, louder whiff, now sure she wouldn't mind.

"What do they smell like?" she asked curiously.

"You," I replied simply, if not a bit breathy. I could feel her blushing.

"Do you like the smell of me?"

"Mhm," I hummed, getting more turned on with my face buried in her silky-soft cotton panties.

"It turns you on?"

"Mmm."

"I like that it turns you on. I think that's sexy."

I took a few more moments to appreciate my sister's scent and discarded the panties to the floor. It was now time to focus on my sister who was lying in front of me completely naked except for socks and the tampon in her pussy. I spread my knees out beside hers and put my hands on her ass again, gouging into the meaty flesh with my fingers, causing my sister to sigh deeply. I squished and massaged the fat of her bottom up and down and around and outward too, eyeing her pinkish puckered asshole. It looked so cute, a tight, circular wrinkle encircled by a ring of scarce hairs that got thicker as it trailed past her taint to her vagina.

I lightly put a fingertip at her butt hole, keeping her large cheeks spread with the other hand. I felt up and down her split with my finger, centering in on her tiny asshole. She was tickled by my light touch. I began to press in slightly and she stopped me, giggling. "Not there!"

"Sorry," I apologized.

"It's ok," she said in an almost seductive voice, smiling back at me. I smiled back as my hands shifted down just underneath her butt cheeks, my thumbs close to her pussy. As I massaged, her swollen outer lips came together and apart with little wet kisses. My big sister hummed and sighed more and more through my massage that closed in on the true focal point, her wet pussy. Her legs spread slightly, I caressed her slit with a thumb with the rest of the fingers of that hand safely between her buttocks. She shivered and giggled, "just couldn't stay out of my ass, huh?"

"It's a nice ass," I said smirking, then pat it twice with my other hand. It wobbled gently like a bowl of jello.

"Thank you baby brother," she said, her smile audible in her voice. I circled her pussy opening with my thumb, flicking past the thin white string hanging limply out of it. My sister began to move against the bed in a slight humping motion, moaning low. She was definitely in heat. I smiled to myself that I was able to have this effect on her. I teased her hole until she was visibly wet, her blood-tinted juices began to leak out of her, even through the tampon and her moans grew desperate and whimper-y. I figured it was time to quit torturing my sister and give her what she needed.

I took the tampon string between my thumb and index finger and slowly pulled. It came out thick and more than half saturated with deep, healthy red. I tossed it on top of her green panties on the floor and then began playing with my sister's thick-haired pussy from behind. I momentarily teased the wet inner lips before sinking inside her torrid well of red ink with a pair of fingers making her gasp. I found her cherry liquid, warm and welcoming, but also snug.

My sister opened her legs more and I re-positioned myself with my knees on the floor, sliding her towards me until she was spread open right before my face at bed's edge. I kept my middle and ring fingers inside her pussy, sliding smoothly toward the depths and back to shore, curling them downwards into her g-spot. "mmmmnnyeah," my sister's voice came out sultry and hoarse.

The whole affair was as sexy as sin. Octavia's juicy passageway hugging my prodding fingers, wet and slick and constricting, and her gorgeous ass directly above, plump and enticing. I stroked her flowing channel, receiving encouraging moans, deep whimpering sighs and random twitches when I had hit a certain spot. I took a handful of my sister's ass and squeezed, watching the flesh conform to my rough grasp and bound back to its normal roundness with youthful elasticity. She yelped and then giggled, then returned to moans of pleasure.

Her ass had me mesmerized. I loved it. And without much thought, I showed my affection for Octavia's sweet ass by treating one of the cheeks to a wet, open-mouthed kiss. As I finger fucked my sister's crimson cunt and showered her ass with hungry kisses, giggles turned back to moans which degraded to heavenly sobs. Tentatively, I allowed my kisses to get closer and closer to the middle, the cleft of her butt cheeks. And then I added some tongue, lashing the split of her butt deeper and deeper until I found her wrinkly ring.

"Fuuuuuck!" she whined. I washed her tasty asshole with a drenched tongue, licking my sister from her hairy taint to the bare skin at the crest of her butt, always lingering and slithering into her butthole itself. "You are so nasty! Don't stop. Fuck! Just don't stop!" she cried out as she snaked her own hand underneath herself and began diddling her achy clit. Soon after, she began to tremble and cry out in a powerful orgasm.

Her pussy pulsed on my easy driving fingers, the walls seeming to get slicker with her gushing juices. I kept my tongue where it belonged, right inside my sister's ass sloshing against her little rosebud as she came all over both of us. She quivered and quaked and moaned out a long, thorough orgasm. At last, she had finished cumming and I slid my filthy fingers out of Octavia's soppy puss, then used both hands to spread her ass as I slurped and licked the very center.

"Mmmmm, mmmmm," my sister moaned low satisfied moans. "Mmmmmm..." she continued for a while. "OK," she breathed, "you can stop licking my ass now, Xy." I got in a few last savoring licks and sucks of her tight ring, kissing the orifice goodbye as it were, then lifted myself away.

"Sorry, got carried away," I chuckled as I stood.

"It's OK. I kinda liked it," she smiled back at me.

"Hm, only kinda?" I asked sarcastically.

"Okay, okay, I admit. It blew my mind," she said, blushing with slightest embarrassment as she flipped around onto her back. Her pussy was a red, creamy mess, parts of her bush resembling a rusted Brillo pad. "Now, take those off and come here so I can thank you," she said with a big smile, focusing on the tent in my grey underwear and the darker circle of precum I had leaked.

I eagerly obeyed, pushing my boxer briefs to the floor. My sister brought herself to the edge of the bed where I stood, keeping the thick red towel underneath her menstruating vagina. Her body rippled softly as she moved, her breasts bouncing and swaying heavily and her full-figured midsection and thighs jiggling liberally. I stood proud, dick stretching out toward her. Once Octavia got comfortable, sitting on the edge of the bed with her legs spread beside my legs, she took my member in a loose fist and began to jerk it up and down.

It felt wonderful to have my sister's hand on my cock again and I let her know it with a groan. She smiled up at me and blushed, shaking her head and grinned bashfully. "What?" I asked, partly amused.

"I just," she started, still stroking my cock. "I just never thought I'd be so excited to..., do fellatio on somebody," she said. "Usually guys have to beg me to suck their cock, but I really want to suck yours. And I never swallowed cum before, but it never occurred to me not to swallow yours," she said plainly. She then wrapped her supple lips around my head and kissed it slow and slicked up the precum with her adroit tongue. Releasing my cock with a wet pop she smiled, not at me this time, but at my cock.

She attacked it again with enthusiasm, taking half the shaft into her warm wet mouth and bobbing back and forth. She stroked my cock at the base as she slurped on the big end, humming as if she was satisfying a deep appetite. Octavia swiveled her head side to side expertly on my stick, keeping her soft mouth nice and wet for me. It was ecstasy.

I raked my fingers through my sister's ink black hair. I stopped for a second when I noticed my fingers were still covered in her blood and cum, feeling apologetic that I had messed up her hair. My sister looked up at me and saw my dilemma and popped my cock out her drooling mouth. She took my hand and sucked her fluids off the two middle fingers, shrugged and then swapped the two fingers for dick again.

I was amazed at how dirty she was being. Sure she had times she brought guys home and I could sometimes hear them fucking, but I never knew she could be such a nasty girl. And according to her, she was really enjoying this.

I combed through my sister's hair, totally in love with her sexiness. Octavia descended to her knees in front of the bed and laid her hands on her lap, sticking out her perfectly sculpted breasts underneath her cock serving mouth. Saliva dribbled messily down her chin to her neck and chest as she bobbed on my manhood.

I gently traced her pretty face with my fingers, appreciating her delicate, soft features - most of all her big blue eyes, full of lust and submissiveness and love. Obediently on her knees, legs together, tits bobbing and eyes begging approval, my big sister looked perfect and the whole picture brought me close to orgasm.

I slipped my hand back through her silky hair to the back of her head and gently pulled her into me, my long cock slithering into her warm throat. I let out a long sigh. Octavia let me use her mouth and I fucked it until I was ready to cum. It felt so damn good I couldn't think straight enough to announce that I was cumming. But no matter, since she was no stranger to cum anyway. I pulled back some and began to stoke my cock, pumping my seed into my sister's mouth.

Her eyes smiled when she felt the cool substance hit her tongue and began to hum deeply on my cock. She kept sucking while I pumped myself between her greedy lips. Once my deposit was made, I took my cock out my sister's mouth and watched her swallow the load of her brother's thick cum, spit smeared all over her mouth, chin and upper chest. No sight is sexier. No girl is sexier. No one is happier than I was at that moment.

*****

The next few months were a dream. When Octavia wasn't on her period, we were still closer than ever. We talked more than we ever had, sharing secrets, being vulnerable with one another, opening up, and more than anything, we laughed a lot. But nothing sexual ever occurred the weeks between her period.

When she was on her period, I would make her cum with fingers and/or tongue, then she would reward me with a blowjob and swallow the prize. Sometimes we would do it two or three days in a row depending on whether she was in enough pain.

It became sort of ritual for us to make each other cum when she had her period. In the third month, on what I believe was the second night of her period, Octavia staggered weakly into my room and lay against me underneath the covers. "Help me," she whispered in a whine, spooning herself against me and arching her ass into my cock. Her voice was a mixture of her two kinds of need. My cock quickly stirred to life as I awoke to my sister sliding my hand between her legs. She was wearing nothing but a pair of high socks and a white tank and me, just boxers.

I found my sister's clit and began to rub until she started to moan and squirm against my manhood which was trapped between her naked ass cheeks. My other hand made its way up her tank to fondle her breasts, her nipples greeting my intrusion with eagerness. In that position, I tinkered my sister's body to a sweet, lasting orgasm. By the time I got her to cum, I was ready too and the pretty noises sis made coupled with her gyrating ass on my dick pushed me over the edge.

"You made me cum," I breathed as I soiled my underwear, humping her ass to get the most of it.

Octavia giggled and ground herself into me. "Oh, I did. You should have warned me. You know how much I love your cum."

I took my hand from between her legs and shoved them down my boxers, then pressed my wet fingers to my sister's lips. She chuckled a bit and said, "thank you, baby," and sucked cum (and her own fluids) off my fingers. Even after all the substances were washed down her throat, she kept sucking on my fingers. I figured she must've had some type of oral fixation. We fell asleep in that very position, spooning, half naked, and filthy with my fingers in my sister's mouth. It was heavenly.

The next morning, I put my ruined sheets in the wash and Octavia and I fought over who would shower first. However, the argument didn't last too long and we found a happy compromise and decided we could shower together. If her full body had looked great dry naked, it was an absolute sin to see it wet naked, and wicked to see it soapy naked. And to touch all her slippery curves and crevices as I washed her! My heart raced, I was breathless and my cock was diamond hard.

My sister then washed me, finishing up with a soapy handjob in response to which I came all over her belly and hairy crotch. We finally rinsed off and dried each other. Octavia had me insert her tampon into her pussy, telling me how to do it and I told her if she ever needed me to do it I would be more than willing. She smiled at me and said, "yeah, I'm sure." She turned to leave the bathroom and added, "and I might take you up on that offer."

*****

I was already looking forward to next month's period. Two days I had inserted and removed Octavia's tampons but she never needed any extra assistance until the third morning. I woke up and went to the bathroom to piss and saw Octavia lying on the bathroom floor like the first time except her legs were toward me and she was wearing only a pair of yellow cotton panties with a rainbow band, her usual tan high socks and a cropped white tshirt.

I already knew what the problem was and immediately set myself to being helpful, getting down and rubbing my sister's ass through the soft panties. "Mmmm, thank you" she sighed weakly and spread her legs, allowing me to shift my hand between and rub her needy pussy.

"Why didn't you come and get me?" I asked.

"Didn't wanna wake you," she said, barely whispering.

"No, always wake me. If you're hurting I wanna help," I said, massaging through Octavia's panties to her pussy.

"You're so sweet," she complimented. I smiled.

I noticed a little wetness forming where I thumbed her sex, but it was spreading too quickly to be her arousal and too thin for blood. "Sorryyyy," she whined, "I..., really had to pee..., but, couldn't make it..." she said apologetically. I then realized she had just pissed her panties a little.

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