My Sister Wears Boxers? Pt. 02

AUTHOR'S NOTE: This story may not be for everyone, so I encourage you to read the tags to see. It's also a continuation, so please read Part 1 first! Otherwise, enjoy!

********************

I was driving a car. A fast car, the fastest in the world. The highway was long and wide, the wind was in my hair, and there was a beautiful girl by my side. My arm was draped around her in the way only cool guys can do, driving with one hand and not bothering to look at where I was going. The Armani suit I was in was a dark black, matching my sunglasses, and I sped down the highway at about 200 mph. The radio was blasting a song, my woman was beautiful, and life was good. As I leaned over to kiss her, she responded by trying to shove a frozen popsicle in my mouth.

Wait, what?

I blinked my eyes, consciousness slowly making its way back to me, as I tried to get a handle on what was going on. It was dark, still some time in the middle of the night. I blinked again, and remembered that I was in my bed, not driving a car. A dream, then. I turned to see the clock, but my view was restricted by a large shadow. That shadow had just managed to wedge open my mouth and slip something in.

Ah, right. That would be my sister's penis.

Ever since that first time with Ruth two weeks ago, the two of us had been inseparable from each other's cocks. If our parents were gone for even five minutes to the store for milk, we'd have our pants off and be giving each our pleasure for pleasure. It was a situation that I didn't mind — easy access to blowjobs whenever I wanted, in exchange for giving one in return. It was fair, and since it was my sister's penis, it didn't technically make me gay, just... unique.

"Sorry, did I wake up?" I heard a quiet voice ask. She didn't take her dick out of my mouth, still trying to get me to take in her full length. "I tried to take care of it myself but, well, you know how it is..."

I did know. Sometime last week Ruth had slipping into my room at night, waking me up due to an erection that she just couldn't get rid of. I helped her, she helped me, and we want back to our beds. It happened again a few nights later, and again last night. She was, somehow, getting even hornier as the days went on.

I let out a sigh as I opened my mouth fully, granting her access to my hole. She eager filled it, wasting no time at all at grabbing the back of my head and taking control. I was still on my side in my bed, which was disorienting as one of her balls kept slapping me in the eye as she facefucked me. I started to gag a little as she hit the back of my throat. The noise caused her to freeze in place, her rhythm slowing dramatically.

"Sorry!" she whispered. "Got carried away there."

Glancing over, I saw it was around two in the morning. Our parents were only a few rooms away, so any loud noises would definitely wake them up. They knew about Ruth's condition, of course, but there was no good way to explain the agreement Ruth and I had stumbled onto. It was better to just leave them in the dark.

Ruth pulled out of my mouth and climbed over me, collapsing on the bed beside me. It was only a twin, but I didn't mind being close to her. She was wearing an orange shirt of a soft fabric, and I spied matching pants on the ground beside the bed. Without asking, she moved her hand over to my cock and asked, "Wanna race?"

"I could be persuaded," I said, already feeling my dick wake up. I tended to get pretty hard when I blew my sister, and tonight was no exception. "You have a bit of a head start though."

Ruth just smiled and pulled off her top, revealing her breasts. Funny enough, I had never had the nerve to ask her her cup size, but going off of old girlfriends I had to guess a decent C, or a large B at worst. As her hand slipped into my boxers, fishing out my semi-hard cock, we kissed, our tongues finding a familiar place in each other's mouths. My hands found her breasts and teased her nipples, alternating from rubbing to flicking to pinching and back again. I heard her moan in my mouth as we kissed.

Ruth was stroking my cock to its full length, which didn't take long. I begrudgingly pulled away from her to kick off my boxers, and Ruth eagerly shimmied her way down to the bottom of the bed. There, she gazed upon my cock in awe. She always did that, as if seeing my penis for the first time. Ruth claimed it was the biggest she had ever seen, but that was a lie. One of the first things we did was compare our sizes to one another, and she beat me by a few centimeters. She licked up the shaft once, then took me in her mouth.

Her mouth — my god, there isn't a mouth like hers in the world. The girl literally gave the world best blowjobs. She knew how and when to tease, but if she wanted to, she could get me to cum in three strokes. Her mouth tightened on my dick, saliva already coating it entirely as she bounced up and down. She released me, sucking on my balls for a few seconds while jerking me, her eyes locked on mine.

"That should be enough," she said, popping one of my balls from her mouth. My sister was right — I was ready to blow any second. Ruth climbed over to me, planted a long, sensual kiss on my mouth, before turning around in a 69-position and waving her dick at me.

"First one to cum does dishes tomorrow," I said. Before she could respond, I grabbed her dick with my mouth and started to suck, my hand massaging her shaft. I felt her tense, and suddenly my own dick was in her mouth, and the race was on.

Racing was something we had discovered when we were short on time. We were both competitive to a fault, and horny as rabbits. I generally lost, but it could hardly be called losing to get an orgasm. That being said, tonight I had a secret weapon.

As we sucked each other off, each feeling the other's cocks swell in our mouths, I took my free hands and reached up to massage Ruth's ass. She didn't respond to my touch, but I knew she was regretting taking the top position because she couldn't do the same to me. As I rubbed her ass, forcing her down my mouth, I gently, but quickly, moved one of my fingers to her asshole.

That caused her to jump. I held on like a bull rider in a rodeo, continuing to tease her hole while I sucked her off. I heard one long, shuddering moan before sprays of cum started to fill my mouth. I swallowed the salty taste easily, using the position to milk her cock dry. I felt the full weight of her fall onto me when she was spent, and I lightly played with the shrinking cock in my mouth with my tongue, until it was too sensitive to touch and she had to pull out.

"That," she said, coming back around to face me with a grin, "was a mean trick."

"Hey, if it works it works," I said, smiling. We kissed again, and she fell back to the bottom of the bed to finish the job. My sister wasn't playing around this time, and once she had me in her mouth, it only took a few seconds before I came. Like me, Ruth swallowed it all. It must run in the family.

Ruth pulled my dick out and wiped her mouth with her hand. "Thanks bro," she said, reaching up for her top. I leaned forward, kissing her again as I handed her shirt to her. "I'll get a handle on these urges one of these days."

"Of all your obsessions, this is hardly the one that I'll complain about," I said back. I watched her throw the shirt on, her hard nipples poking through the fabric. She climbed off the bed and slipped into her pants, her hard-on mostly gone, though I did spy the outline of her cock. She gave me a wink and an air kiss, and crept quickly out of my room.

I laid back on the bed, hands behind my head as I stared at the ceiling, replaying the events of the night. Having a personal blowjob ready for you whenever you want is every man's dream. The only thing that would be better is if she would let me fuck her.

I thought about fucking my sister until I fell asleep.

********************

"There's money on the table, you can use it for burgers or something," my mom was saying. She and my dad were going to see some gala in the city, and would be gone for most of the night. When we heard about it, Ruth and I gave each other dirty looks for the rest of the week, and I convinced her to hold off on any more nightly visits until then. She had begrudgingly agreed, and now that the night was here, there was an insane amount of lust in her eyes. I don't know how our parents missed it.

"We'll probably do pizza," Ruth said nonchalantly. "Catch a movie on TV or something."

"So boring," my dad said. "Why don't you two ever do something? Go out in the world, meet some people. Tony, when's the last time you had a girl in your life?"

"Honey!" my mom chastised him. "Let them be innocent for a little while longer, alright? Pizza and TV is just fine. Now come on, we're running late as it is."

The two of them hopped in the car and pulled out of the driveway. Ruth and I stood by the door, waving goodbye, until the car turned the corner. The literal second that it was out of sight, we were on each other like bunnies. We hadn't even stopped to close the door.

"Ruth, wait," I said, breaking the kiss and pulling my hand out from under her shirt. She paused, looking at me confused as she removed her hand from my crotch. "We need to have a talk."

"Uh oh," she said. She closed the door and turned to me, face towards the floor. "You're not giving me the 'It's not you it's me' speech are you?"

"What? No, nothing like that."

"Alright..." Ruth shrugged as she made her way to the living room. She sat down on the far end of the couch, looking at the window. "I think I know what this is about anyway."

"You... do?" I asked hesitantly. I followed her and sat down beside her, only a small bit of distance keeping us from touching. She still wasn't looking at me.

"Yeah, and I get it. This thing between us... it's weird, and it's not what you wanted, at least not in the long term. I've been nonstop horny and you want to slow things down, which I completely understand. Or even just... stop..." Her voice had become very quiet.

"Ruth, don't be ridiculous." I pulled at her arm until she turned to me, and when she did, I leaned in and kissed her, hard. "Listen, you're my sister and I'll love you no matter what. But this thing between us? It's bigger, somehow. It's better. I don't want it to end, I want it to keep going! I don't want less of you, I want... more."

Her eye grew with each word I said, and some pink started to color her face. "Wait, what? Sorry, I don't think I heard you right. You want —"

"I want everything." I said, kissing her again. "I want these lips..." I moved down to kiss her breasts over her shirt. "I want these breasts..." I moved down further to her crotch and kissed it gently. "I want everything. I love you Ruth, and I want to show you just how much."

"I... I..." Of all the reactions I was expecting, tears weren't at the top of my guess list. "I don't know what to say. This is... I never expected this."

"Is it not what you want?" I asked, pulling away. She grabbed by my shoulders and pulled me back.

"No! No, I want it too." She bit her lip nervously, and my dick almost burst in lust. "I just never thought I'd get to this point, you know? Especially with my brother."

"That just makes it all the better," I grinned. "And with mom and dad gone for the rest of the day..." I purposely let my sentence trail off.

"Oh don't worry, I think we're on the same page now," she said. Ruth leaned in again and kissed me, pushing me onto my back as she straddled me. We made out for a few minutes, both of our erections hitting one another as we pressed our bodies closer. Eventually she broke apart and said, "Alright, well... give me five minutes to get ready, then join me in my room."

"If I can wait that long," I joked.

"You better!" Ruth playfully tickled me as she got up, almost skipping out of the room and up the stairs. Laying there on the couch, I put my hands behind my head and grinned to myself. It was finally happening. Finally, FINALLY I would be having sex with Ruth. Blowjobs were great and all, but there's just some pleasure that a mouth can't simulate. I had been with one girl before, my ex Anabelle, but we had broken up months ago, and the urge to be balls deep in another girl was starting to get to me. Of course I had never tried anal before, but how much different could it be? A hole's a hole, after all.

I had lost track of time in my daydreaming, but figured enough time had passed. I stood up, not surprised at all to find my erection at full strength. Not wanting to bother with it, I stripped down completely, letting my dick hang free. I threw my clothes in a pile by the stairs, took a moment to steady my heart, and walked upstairs.

"Thought you had forgotten me," I heard a voice say as I made my way to the top.

"As if," I said, entering her room. The lighting was low, but not impossible to see. There were some scarves thrown over the lights for mood lighting giving the room an orange-red tint. The bed was prepped with the sheets pulled back and a few strategic pillows laid out. On the table by the bed I saw a bottle of lube.

But my eyes were fully on my sister. Her yellow-gold hair was down, falling over both her shoulders as she stood before me. She, like me, had stripped completely, save for a pair of black panties that I didn't know she owned. A hole has been cut in the front, and her glistening dick poked free from it, standing harder than I had ever seen it before.

"That," I said, catching my breath, "is fucking sexy."

Ruth giggled as she ran to me, jumping for me to catch her. I did, and we kissed, our naked bodies rubbing against one another as we held each other as tightly as we could. My arms explored every inch of her back as if for the first time. I could feel her heart facing as fast as mine. As we kissed, I felt something sticky against my stomach.

"Aw, that's okay," I said reassuringly. "We have all day."

"What?" Ruth looked down and laughed. "Oh, no, that's not my cum silly. It's lube."

I gave her a quizzical expression, but she moved in for another kiss. As I let her tongue into my mouth, a fear started to overtake me. I played back our conversation from downstairs...I did say that I wanted to have sex with her, didn't I? But... did I not make it clear that I would be fucking her, and not the other way around? The more I thought on it, the less certain I became.

"Enough of that," Ruth said, hoping off me in a single leap. "If we keep going I'm not going to last and all your efforts will have been wasted." She smiled, a truly genuine smile. I glanced from her, to the lube, to her cock, and back. I wanted to fuck her, not the other way around. This was all wrong... And yet, the more I thought about us, I thought about what my sister meant to me. I loved her, and wanted to be with her. Wouldn't it eventually come to this path, given enough time? If I backed out now, she'd be crushed, probably unable to trust me again. No, in my heart I knew there was only one thing to do.

I smiled back.

"You're going to have to be gentle," I said, making my way to the bed. I climbed up it, assuming a doggystyle position. "And slow. And... gentle."

"I'm not going to break you," Ruth said playfully running her hands down my back. Damn if it didn't feel good. She kept touching me, hands creeping closer and closer to my ass. "Just relax. If it makes you feel any better I've read up on this online a lot."

"Great, I'm going to be fucked by a nerd," I teased. Ruth apparently didn't like that, because she slapped my ass. I let out a yelp and turned to her, glaring. She just laughed and said, "I said loosen up." I saw her climb up on the bed, lining up her dick with my asshole.

I turned from her, putting my head by my hands, and tried to loosen my ass. I felt something touch it and almost jumped right there — it was cold! "Just the lube," I heard her say. My sister massaged the lube into place until I almost felt it leaking down my balls. If I was ever going to take a dick up the ass, this was the way to do it.

I felt something else touch my asshole, but this time it didn't move away. It pushed its way further into me, causing me to wince slightly. It retreated, then moved in a little deeper, then retreated again. This processed continued, very slowly, until before I knew it I could feel my sister's balls hitting my own.

"There," she said, panting like she was out of breath. "How's it feel?"

"Warm," I answered. "I feel so... full."

"Well I can say this is the best feeling I've ever felt. Even if you wanted to stop now, it would have been worth it just for this."

"No, I can keep going," I said, determined. "Come on you dirty slut, fuck me with that big hard cock of yours."

Ruth burst into laughter. Each laugh caused her cock to twitch, which was a new experience for my ass. "Holy shit, Tony, no. You are not good at dirty talk."

"Just... trying it out." I fumbled for a better position, putting weight on my elbows. I squeezed my ass a bit, and I heard Ruth moan in delight. "Alright, alright, sorry. I was just... enjoying this."

Ruth placed her hands on my hips, and slowly pulled out of me. She must have gone almost 90%, before moving back in. She hit me with a smack, her hot cock exiting and returning with more force than the last. I won't lie; it hurt at first. The pain of taking her cock was new and not at all pleasurable — I found my self waiting for it to be over. But as she picked up in speed, as her hands tightened their grips and her thrusting became more focused, I found myself moving with it. My ass would bounce back into her, almost daring her to hit me harder and deeper than before. Below, my own cock twitched with delight each time her full length came barreling into me.

There were no words spoken. Nothing needed to be said. The only sound in the entire house was my sister's lubed cock slammed against my own lubed asshole. It was a fast pace now, her hands digging into my hips, the bed shaking with each thrust. Surprisingly, she didn't last long.

"Fuck, Tony," she said panting with each strained word. "I'm so close."

"Mmmm I bet," I said, letting out a moan of my own. "Come on Ruth, do it. Cum for me. Cum inside your brother's ass. Fuck me like you mean it!"

I'm not sure if the dirty talk helped or if it was just her time, but I felt Ruth explode into my ass. Streak after streak of cum filled me, but unlike my mouth, there was no where for this cum to go. Ruth kept thrusting as she came, a loud "Fuuuuuuuuuuuck" coming from her. Being alone in the house, there was no silencer on her orgasmic cry. After the last spurt of cum escaped her, she thrust one last time into me, collapsing onto the bed, by means of me. Her dick throbbed in my ass, cum leaking in and around it. We were both out of breath, but that didn't stop her from inching forward to kiss the back of my head.

"That was... incredible doesn't do it justice," she said, resting her head on my back. "Holy crap, is that what sex is? No wonder guys will do anything for it."

"Pretty great right?" I asked.

"And you?"

"What about me?"

"How was it?"

I gave a small shrug. "Wasn't the worst thing in the world," I admitted. "I think it'll get easier with time."

There was a few seconds of silence. "So you'd... be open to doing that again?" she asked.

"I think it could be arranged," I said wryly. I turned around to kiss her, her dick popping out of me and a large glob of cum falling onto the bed. "Ah, shit!"

"I got it!" she shouted, leaping to her feet and running to get a towel. There was something about my sister, still in the black panties with her semi-hard dick flopping about, that turned me on. My own dick pulsed at the sight of her running back in. As she cleaned, she looked at my dick. "That for me?" she asked with a smile.