Prenuptial Relations Ch. 01

SUMMARY: This story is about an older brother and his younger sister having sex days before he is supposed to get married. He thinks it will be ok as long as they don't get intimate with each other and it's just sex, but he's wrong.

All characters in this story are 18 or older.

AUTHOR NOTE: I decided to write this story from the male point of view. Please excuse any inaccurate descriptions! Also, as usual, I edited this story myself, so there may be some typos, grammatical mistakes, etc. that I missed. I'm doing this for fun, so please judge it with that in mind!

DISCLAIMER: This story is a work of fiction. Any character resemblances to real life personae are strictly coincidental. Copying, re-posting, storing (whether digitally or in print form) or redistribution of this material is prohibited.

STORY:

PART I.

I was getting married in two days. It still seemed strange to me. I couldn't believe I was getting married! I was twenty-eight and had been dating my fiancé, Wendy, since we were both seventeen. She was beautiful and smart and funny and... perfect. She had long, blonde hair, wavy and silky. She was about four inches shorter than me at 5'6". I knew she was the one I wanted to spend the rest of my life with.

Or so I thought.

Something was about to happen that would put a spin on my entire life. You see, two days before my wedding, I had sex with my little sister. Yeah. That happened. But let me explain, starting with a little back story. First of all, my sister is nineteen. Nine years younger than me. And I had known that she had a crush on me for as long as I could remember. Of course, I never thought much of it. I just thought it was a thing little girls did. Develop crushes on immediate family members. If it hadn't been me, I'm sure it would have been my dad. Either way, I just thought it was a normal part of maturity and puberty.

Her name is Shelly. She's a beautiful young girl. Her hair is brown and she keeps it long enough that it hangs past her shoulder blades. She has a beautiful smile with perfect teeth and twinkling brown eyes. I remember seeing her body start to change when she was twelve. Since then, she had really grown into it. She had perfect breasts. They weren't too big, but they were plenty big enough on her short body to give her an ample amount of cleavage when she wore the right shirts. All in all, she was extremely good looking.

She used to flirt with me. Like, all the time. It was all harmless at first, but over the years, as her education increased, her flirting got a little more intense. Again, I laughed it off most of the time. She was a kid to me, and it was what kids did. Except a couple times after she turned eighteen, I would wake up with her in bed with me, rubbing me. One time she actually had her hand inside my pants, stroking my penis. I chased her out when that happened. That was almost a year ago. Of course, once she was gone from my room, I masturbated like mad. Just because it was my little sister didn't make me immune to stimulation like that. I was horny!

Nothing too extreme had happened since that night. She still flirted, and occasionally petted me, or rubbed my butt or my chest, but that was about it. When I told her I was engaged, I'll never forget her reaction. She pouted. As in, little-girl-not-getting-her-way pouting. I messed with her hair to try to lighten the mood, and then shrugged it off.

That was three months ago. Now, it was two days before the big day.

Lying in bed, I was having a hard time falling asleep. My mind was all over the place, thinking about all of my new responsibilities once I got married. We were going to live with my parents for a few months, after the wedding. That helped a little. Plus we both already had decent paying jobs. But there were so many things I didn't know, like how to do taxes once you're married. Things like that. In any case, my head was filled with enough things to worry about that I struggled to find sleep.

Somewhere around two in the morning, I heard footsteps in the hallway. I didn't think much of it at first, until I realized they were coming closer to my room. When the door started creeping open, I lifted my head to see who it was. I figured it was my fiancé. She slept in the guest room next to my parents' room. That was the agreement I had in exchange for letting us live there. We had to wait until after we were married to sleep in the same bed. But that didn't stop her from sneaking in to make love to me every now and then.

Silently, a figure made its way into my room, closing the door on the way. Frowning, I tried to see better, but it was too dark. All I could see was a faint silhouette, framed by shadows. When the figure reached my bed, I heard a clunk and then a curse. That's when I knew who it was.

"Shelly?" I whispered.

My sister climbed into my bed without a word. I heard her lift the covers and shimmy underneath. Once she was lying next to me, she settled her head down on my other pillow. The one that my fiancé usually used. Sighing, I asked my sister gently, "What's wrong?"

Shelly didn't answer right away, but I could tell she was working out something to say, so I kept silent. After a long hesitation, she whispered, "You're really getting married."

"Yeah," I said, shifting a little.

Another long silence stretched between us. I could hear her breathing. The bed creaked as she moved and I heard the covers rustle. Then I felt her pushing up next to me, lying sideways. She draped a hand across my chest and rested her cheek against my arm. She felt warm. And cozy. I didn't move a muscle.

For several minutes neither of us moved, nor spoke. Her hand started moving absently on my chest, like something a child might do while cuddling up with a blanket. I didn't bother stopping her. Finally, she spoke, her voice a soft whisper in my ear, "I always thought you would be with me forever."

My heart melted at her words. She was my little sister. My princess sister. With the age difference, we had been close in a different way than if we had been little together. I was her big brother, but also her protector. Her confidant. Her best friend as she grew up. And, as I mentioned earlier, her childhood crush. Reaching over, I tried to find her shoulder, but my hand landed on her side instead. The second I touched her, her body tensed. I felt her hand on my chest stop moving and she inhaled a short breath, then held it.

Instead of moving my hand up to pat her shoulder, I kept it there on her side. She felt soft. Slowly, I started rubbing my thumb against her, trying to be comforting. Her body loosened and she squirmed beside me, and a few seconds later, she resumed her absent caressing of my chest. I felt her hand slide just a little and suddenly her fingertips were gliding back and forth across my nipple through my shirt. I didn't want to embarrass her, so I didn't say anything.

My sister and I lay in silence for the next ten minutes. But our hands continued to move, barely caressing each other. She went from rubbing to raking her nails gently across my chest, then back to rubbing. All the while, she kept going back to my nipple. At the same time, I found myself starting to slide my hand up and down her side, massaging her as I went. After several minutes, it dawned on me quite suddenly that what she was doing to me was starting to make my body tingle. It was turning me on a little.

I had to figure out a way to stop without embarrassing her. So I gently pulled away and made it as if I was stretching. I threw in a yawn for good measure and when I settled back down, her hand was on my stomach instead of my chest and I was no longer holding onto her. That worked for about one minute, and then my little sister started rubbing my stomach. It wasn't nearly as arousing as her rubbing my nipple, but in some ways, it was almost more erotic. My mind started tossing images my way of just how close her hand was to my cock. And once I started down that path, I started thinking about my sister giving me a hand job.

"Can I sleep with you tonight?" Shelly asked suddenly.

Shrugging uncomfortably, I nodded into the dark room and then whispered, "Sure."

I couldn't see her smile, but I felt it. She was beaming. Her hand on my stomach opened wide and then squeezed my skin. In the process, she pulled herself closer to me and before I could reposition myself, I felt her slide one leg on top of mine, resting it on my thigh. God she was warm. Just then, I realized that I could smell a faint whiff of her perfume. It smelled like candy.

The next little while, I lay completely still while my sister resumed her slow caressing with her hand. She kept it on my stomach, but I don't think that did much to assuage my growing arousal. I tried my best to hide that fact from her, straining to control my breathing. It was difficult. After several minutes, she nestled herself even closer, snugging her other leg against the side of mine. I realized in that moment that I could feel a heat radiating from between her legs. Inhaling sharply, I tried to think about something else. Anything else.

My sister's hand was moving down suddenly and I froze. In that moment, I asked myself what I would do if she tried to put her hand down my pants again. When it had happened a year ago, it was easy to make her stop. She caught me off guard, and fast asleep. When I woke, I was so surprised and shocked by what was happening, it was easy to snap at her.

Not so this time. The way she had been caressing my body, slowly fueling my desire for half an hour, I knew there was no way she could surprise me. And without the element of surprise, I didn't know if I could muster the will to actually make her stop. But I didn't have to worry about it yet. She didn't move down like I suspected she might. Instead, when she reached the hem of my shirt, I felt her lift it up and place her hand underneath, against the bare skin of my stomach.

My skin tingled immediately where her hand rested. Tingled with a warmth that seemed to radiate from her. She resumed her caressing, tickling her fingers back and forth across my belly. Shifting slightly, I tried to force myself not to be aroused by what she was doing. Did she even realize how much it was turning me on?

Shelly spent the next twenty minutes massaging my stomach. I was silent the entire time, feeling myself becoming mesmerized by her gentle touches. Unfortunately, I didn't realize that she had crept her way up my torso until it was too late. When her hand slid onto my chest and I felt her fingers brush across my nipple once more, I was already breathing heavily. The tingles that came alive at that moment were intense, and they sent little jolts of pleasure straight down into my cock, which had been steadily growing stiff the entire time.

I can honestly say, I didn't know what to do. I had been fending off her flirtatious advances for so long, my defenses had become second nature. But as I lay there, I felt helpless. Try as I may, I could not muster my defenses to kick in. It was like my perimeter had already been breached, and I was just waiting for the inevitable. And to compound it even further, I felt sure that my lack of resistance was giving her the idea that it was ok to push my limits even further. And push them she did.

Shelly slowly started moving her leg atop mine. It was subtle at first, and with her hand liberally exploring my bare chest, I didn't notice when it started. When I did notice, I focused on the warmth emanating from her inner thigh as she slid it along the top of mine. Suddenly, her knee grazed the stiff bulge of my erection. She hesitated when she first made contact, but resumed her deliberate movement a second later. Before I could even begin to think about saying something to make her stop, she was moving her leg in a circular pattern, openly rubbing my cock through my pants.

Exhaling, I tried to calm myself. Heat and pleasure followed her knee as she completed circuit after circuit. My erection started throbbing, sending smoldering pulses of pleasure up into my stomach as her knee continued its relentless movement. When her hand started moving on my chest again, my body twitched. I hadn't even realized she had stopped moving it. But she wasn't rubbing my chest with it. Instead, she was letting her fingertips trail their way downward. When she reached my stomach, I flinched, but she moved past the ticklish spot immediately.

My sister's hand suddenly slid onto my sweats and she pulled her knee out of the way at the same time. When I felt her fingers glide across my tingling erection, the shock hit me like I had been doused with a bucket of ice water. Except ice water would have actually taken my arousal down a few notches. Instead, a fire ignited inside me that I couldn't hope to contain. I thought I wanted to tell her to stop. I told myself that, firmly. But I knew I was lying to myself.

"Can I ask a favor?" my sister spoke and my eyes fluttered open. I hadn't heard a sound except for her rustling movements as she seduced me physically. Hearing her whisper just then jolted me out of my reverie. A little, anyway.

When I tried to answer, nothing came out. Clearing my throat, I whispered hoarsely, "Wh-what?"

Shelly shifted slightly and I could tell she had lifted her head up to look at me. When I looked down at her, I was surprised to realize that I could actually see her. My eyes must have grown accustomed to the darkness of the room. There was just enough light coming in through my window from the moon that I could make out the features of her face. It had a slightly bluish-white cast to it. She was smiling at me. "What favor?" I repeated.

Seconds ticked by. Thirty. Fifty. One minute. Was she going to say anything? I opened my mouth to repeat my question but she opened hers at the same time and whispered, "Have sex with me." She didn't phrase it as a question.

As her words sank into my brain, I felt dizzy. Before I could recover, she slid her hand that was pressed against my penis, letting her fingers run along the edges of my hard-on. I shivered uncontrollably, my arousal skyrocketing. My breathing was coming in near gasps, and the dizziness turned to lightheadedness. Slowly, Shelly ran her fingers up and down the length of my shaft, pressing her fingers against it through the fabric of my sweats. Explosions were happening in my head, fueled by the taboo situation happening between my sister and my cock.

"Please?" she whimpered, almost moaning the word. She continued stroking me while she stared at my face.

This was clearly beyond harmless flirting. And yet, why was I even hesitating? My defenses were already demolished. She had broken through in a single hour of "innocent" foreplay that I hadn't managed to stop, after years of failed attempts. In the back of my mind, I knew that I wanted to make mad love to her then and there. Swallowing nervously, I nodded slowly as I whispered, "Ok." Shit.

Shelly's smile stretched all the way across her face and she stroked me several more times before pulling her hand away from my crotch. When the assault of my cock eased, I sucked in a deep breath. A thought came to me then, which I blurted out.

"Nothing intimate. This has to be just sex, Shelly," my words lacked the force that I conjured them with. She stared at me so hard, I felt like she was trying to pummel me to silence with her eyes alone. I got three short words in before I lost all ability to speak. "I mean it," I said sternly. Well, it sounded stern in my head.

Blessedly, my sister nodded, pulling her gaze away from me. "Ok. Ok, fine," she said. I couldn't tell if she sounded upset or not. Then she added, "Nothing intimate. It'll just be fucking."

"Sex," I corrected her.

"That's what I said," she responded as she slid a few inches away from me, untangling her legs from mine.

I rolled my eyes at her, but I don't think she noticed. I watched as she sat up beside me. I could almost wish that my eyes hadn't adjusted to the dimly lit room, but I knew that would be yet another lie to myself. Staring at her, I was mesmerized as she reached both hands down to the bottom of her shirt and took hold of it. She didn't waste any time trying to be "seductive". I'm sure she must know how thorough her seduction had already been.

When my sister lifted her shirt up over her head, I couldn't help but let my jaw drop open as I gaped at her breasts. They were absolutely gorgeous. In my stunned silence, all I could think about as I stared at her perfect tits was how beautiful my sister was. No. Not beautiful. My sister was a fucking goddess, and I just never realized it before.

I couldn't pull my gaze away from those perfect boobs, though. I always thought they were a nice size and shape, but seeing them in the flesh like that, right before my eyes, was something else entirely. They were perfectly round, jutting out from her teenage body in way that screamed "beauty". I guessed they were a fleshy C cup. And I had never seen areolas like hers. Most girls I had been with, including my fiancé, had large areolas that extended three or more inches across. But Shelly's were much smaller, maybe an inch and a half across. They seemed somehow... elegant. My mind immediately conjured up images of me leaning forward and taking those beautiful nipples into my mouth, suckling them, swirling my tongue around her areolas while I worried at them gently until she started squirming. But no. That would be way too intimate. This was just sex, I told myself. It had to be.

A foreign sound reached my ears and I blinked. It took me a minute to realize the noise had come from my own throat. It was like a growl, only more than that. Somewhere in the depths of my mind, I felt something shake free. Some carnal impression settled over me. I realized with sober clarity that I was completely rock hard. My cock felt more swollen than I could ever remember. Whether my mind agreed or not, my body wanted this. It wanted a taste of this elegant goddess.

Swallowing, I slowly lifted my head up until I met my sister's eyes. Then I swallowed again. Good god I wanted her. She had just lowered her arms and was smiling at me, unashamed at her naked upper half. Reaching her hands up to her breasts, she hoisted them up a little and then teased, "You like these babies?"

I closed my eyes, stifling a groan and then whispered, "Let's just get this over with."

Shelly giggled. Then she whispered, "Take your clothes off, dude."

With a sigh, I complied. But I kept my eyes closed while I pulled my shirt off and then struggled with my sweats. Fifteen seconds later, I was completely naked except for the pair of socks that I left on. I could feel my cock twitching. I still hadn't opened my eyes, though. I wondered if she was staring at my penis. Probably, I decided. My sister was a fucking hornball.

When the bed shifted and I felt her climbing toward me, I finally opened my eyes again. Shelly was up on her knees, completely and utterly naked. My eyes took her in hungrily, devouring everything I could see in a heartbeat. Her breasts and nipples were hard to resist staring at, but my eyes drooped lower. To her teenage pussy.

Oh.

My.

Fucking.

God.

It was... beautiful. There wasn't even a hint of hair anywhere on her. Her lips were smooth, with rounded, gentle curves. Not the harsh, mushy lips I was used to with my fiancé. Not that I didn't enjoy my fiancé's pussy, too. But somehow, my sister's pussy was perfection. I couldn't even remember if the girls I had dated when I was a teen had such perfect pussies. It didn't much matter anyway. Those thoughts were all fleeting. My focus was on the very real fact that I was about to have sex with my sister. My nineteen-year-old sister.

And I wanted it like I never wanted anything before.