Prom Date

[musicankane]

Her insides were hot and wet even to my already wet fingers. This was a slick wetness, the kind that would allow my cock to slip into her velvet sheath with ease. Still the feel of her wrapped around my fingers was interesting. I wiggled my fingers and felt her walls shift and move with my movements. It was no wonder that most guys fingered their girlfriends, at least from what I've heard around campus, it was a very interesting feeling. Plus it was a way to get at least some part of me inside of her.

I looked up at her shower cap and chuckled, "Let's get out of the shower first, I can't take that stupid cap seriously." I told her.

Regretably I pulled my fingers from her hole and turned around to shut the water off. Then we climbed out of the shower together. Kim picked up the towel she had let fall to the floor and I grabbed one off the nearby shelf. As we dried off I couldn't help but keep my eyes on her, the way her body moved and swayed with her motions just drove me crazy.

There was a pit of regret in my stomach though. I knew that this could never last like this. After tonight she would return to her happy married life and I would yet again be alone and single. My next chance to get laid would be a long ways off, even if things changed a little bit for me at school. It sucked, and I didn't want it to happen. Kim was my sister though, and ultimately I knew I had to let it go sooner rather than later.

That didn't mean that I couldn't enjoy it while it lasted. We left the bathroom and the first thing I noticed was the scattered condoms on the bed. "Christ how many did you grab from that bowl?" I asked in disbelief.

 

[kimberlee]

I felt his fingers flex and move inside me and I had to close my eyes rolled up. I moaned softly at the sensation. My hand reached out to return like for like when he suddenly pulled his fingers out and made a comment about the shower cap. The nerve of the man I thought hilariously. I honestly couldn't wait to get the damned thing off.

I took off the cap off and shook my hair free.

I didn't dry myself all businesslike as I usually do. Not with my audience that apparently found the female form - mine in particular at the moment - most amazing and took my time giving him something of a show. I took my audience appreciation survey from the way his cock remained rock hard.

I have to admit to a certain degree of fascination, myself. The alley had been dark and my view of him hadn't been as optimal as it was now. And I swear it sneaked peeks now and again with its one eye. I had to smile at the thought.

That was when I noticed Jake slow down for a bit. I caught the edge of a frown before it disappeared altogether. I wonder what that was about? I thought as I finished up drying. I knew I should be feeling a crushing weight of guilt because of cheating on John and not with some guy at work but with my own brother; but, I didn't. I supposed that would come later.

I followed Jake from the bathroom and actually ran into him when he stopped suddenly.

"Christ how many did you grab from that bowl?" I heard him ask.

I looked around him and was surprised to see the condom packages strewn all over the bed. I would have sworn... And there they were. A few of the packages remained where I'd placed them; but, I hadn't thought about the fan by the window. The small packages were light and my small tower had been toppled.

"Enough for tonight?" I asked in an all too innocent voice. I did plan on using a number of them; but, only the one I'd sabotaged in its conventional method of use. And even that one would end up working more like a cockring after Jake put a few enthusiastic thrusts behind it.

The tease wasn't of the normal sisterly sort; but, it was my job to kid my little brother. It was in the big sister handbook. However, while having sex with him wasn't mentioned, I was great at improvisation.

I moved around him and picked up the packaged condoms from the bed and placed them into the bedside counter's drawer. I found the one I'd pierced a number of times and rubbed my fingers over the pin holes so they weren't obvious. Not that I needed to hide anything from Jake; but...

"Let's try one on for size, shall we?" I asked.

 

[musicankane]

I goffed at her joke about using all the condoms tonight. There had to be at least eight on the bed and I didn't think I could use all eight tonight, first night of sex or not, nine goddamn times would have my skin falling off I was sure of that. Still it made me feel better about Kim's view on having sex with me. Clearly she was open and willing to let me have at her numerous times, maybe there was hope that even beyond tonight I might still get some from her.

She moved over and snagged a condom off the bed and tore open the paper. She smiled and held it up for me to see, "Let's try one on shall we?"

I nodded, though a little sad that I wasn't going to be bareback inside of her again because it had been awesome the first time and I had heard a bunch of rumor about how shitty sex was with a condom compared to without. I also figured I was inexperienced enough right now that it wouldn't matter much. So I walked over to her, my dick leading my way and reached out for the rubber sock.

She gave it to me and I looked at it trying to see which way it rolled down. I fit the end to my tip and rolled it down my shaft, wincing as I got the tight rubber ring down toward my base. "Is it supposed to pinch like this?" I asked in a worried voice. "It kind of hurts." I said looking down I saw the rubber strenched thin around my dick and figured it was supposed to be thin to promote "feeling" or whatever.

But the ring looked like it was digging into my shaft and I wasn't sure that it was supposed to happen that way.

 

[kimberlee]

I shrugged and said, "They were for free. They're probably good for the average guy there. You just... Well, we'll get you a pack more your size tomorrow."

He turned a look on me with such hope that I didn't dare quash it. I knew he was thinking about me as a future sex partner; but, we had our separate lives and I wasn't certain that I could keep cheating on John. Tonight had held extenuating circumstances and I supposed that spending the night with him would boost his self-confidence. It was perhaps a little repayment for his earlier actions on my behalf.

I did want to keep in closer contact; but, if Mom ever found out, she'd kill me. And if John learned of me having an affair - with my brother, no less - he'd be devastated. I didn't want to be the source of that pain.

Pehaps, I could create some fiction in which 'Jake's girlfriend' stopped by on occasion and they eventually broke up - leaving an opening spot for someone to enter Jake's romantic life.

I shook the thoughts from my mind. The future could fend for itself tonight. I needed to keep my mind in the present.

I don't know if I'm the only one; but, I find the sight of a hard cock in a condom to be erotic. All that strength and power barely held in check by that bit of latex. The smooth, long, hard length of a man's shaft seemed only further emphasized.

God, I was getting so freaking wet just looking at it. I wanted to touch it, but didn't dare. I poked holes in this one and while I couldn't see the pin holes, I didn't want to have to explain to my brother why I insisted he wear a sabotaged condom - especially with the negative comments he'd made earlier about how tight it was.

I didn't bother with false modesty. I dropped my towel where I stood, climbed onto the bed and parted my legs as my back made contact with the mattress.

"Come on, baby. Give it to me," my voice sultry and filled with need. The future could wait. Tonight, he was mine and I was his.

 

[musicankane]

While the condom was uncomfortable I figured that it was normal. Though Kim had said I was a little bigger than what was normal for this pack of condoms, I think she was trying to make me feel better. Whatever though right? I mean no guy I've ever heard of liked to wear a condom, though most of that shit was in movies. Quite frankly I loved that Kim was trying to make me feel better and feel like a man.

I would tolerate the discomfort and probably wouldn't even notice once I was buried inside of her. God I was tingling at just the thought of entering her again, to be wrapped by her velvety walls.

Kim laid back on the bed and her legs parted, opened for me. I smiled and moved onto the bed with her. I slowly crawled over her, my cock finding the space between her legs like it had eyes of it's own. I looked deep into my sister's eyes and said, "You're amazing Kim."

Then I kissed my sister at the same time as I pushed my condom covered cock into her.

The first thing I noticed was the difference the condom made. I slide into her and I could feel the pressure of her walls around me, the heat of her body, but I could not feel her wetness, I could not feel the folds and caresses of her walls that they gave me last time with only bare skin. It was much different but it also didn't feel like I was going to cum right away either. So there was good and bad about it.

Frankly I didn't have enough experience with sex to really complain about this. I buried my face into her neck, kissing and licking the soft skin of her neck. My hand cupped and squeezed her breasts, my whole body alive at being naked with her. I moved my whole body on her, rubbing her skin on mine, just enjoying the feeling of her body on mine.

My hips moved firmly, able to slide in and out of her without worrying about cumming right away. Man this is great.

 

[kimberlee]

Th way he said I was amazing couldn't help but bring a smile to my face. I have to admit to feeling some surprise at how he just entered me. I'd expected Jake to stop and carefully guide himself into me. Instead, his cock had acted like a guided missile. It found its target and penetrated deeply without the least pause. I imagine some of that surpise was reflected in my eyes.

I don't think my brother noticed it, however. This was only his second time having sex and our first time on an actual bed. Maybe he took it for granted that his member would find its way into my tunnel; but, I think this was the first time that something like this had happened. John always guided his love muscle to its destination.

Maybe I was making more out of the incident than necessary and Jake had just gotten lucky - well, in more than one way. Whatever the case, something clicked inside me. My reasons behind allowing him have sex with me once again. I wanted this and I wanted him.

The fluid way he'd entered me made what we were doing natural and right - made it feel that he was where he belonged. He'd managed to blow my mind and we were only starting.

I wrapped my legs around him and eagerly rose to meet his every thrust as we lay there together. I drew his mouth from my neck and kissed him with hunger. My tongue demanded entrance into his mouth, then slid back in invitation. The kiss moved back and forth between his mouth and mine.

Our lips parted and I directed him to take my legs onto his shoulders. "It'll let you go even deeper. I want you to pound my pussy, Jake." As we changed the position of my legs on his body, his cock slipped out of me; but, it unerringly returned with his next thrust. "Fuck me until my screams of pleasure wake those unlucky enough to have rooms nearby scream for us to shut up - but secretly wish they were us. Do it, honey. Do me."

 

[musicankane]

The way Kim kissed me, it was unlike any of our kisses before. Sure we had let our tongues dance about, but this was different. Her tongue hunt me down and probed into my mouth like it demanded to be there. It was like a cat and mouse game a bit, pushing and pulling back and forth. The way her legs wrapped around my hips I wondered what had changed in her mind.

Her hips worked with me as I moved in and out of her. I could tell she was getting very wet the way I could pump in and our of her. Her body still tried to clamp onto to me as I pulled and pushed my way into her. Still I couldn't help but notice how much the condom dulled the feeling compared to what I experienced at the car earlier.

Then Kim surprised me and told me to pound her until she screamed. That made by cock surge inside of her and I sat up to do as she said. God she was amazing, were all girls like this or only my sister? How ironic it would be for my sister to ruin me for other girls because nobody else could fuck like her.

She moved her legs up and I held them on my shoulders. Using them like a brace I rose up and began to thrust into her. I grunt with the effort, and so did the bed. But the reward for my work was the sexiest sounds erupting from Kim's lips. Her moans urged me on and I wanted to slam into her harder and faster, driven by lust in order to hear what kind of noises I could get her to make.

 

[kimberlee]

I've done my share of moaning and groaning; but, I've never been a screamer. Sex was great and all; I just wasn't THAT enthusiastic about it.

As Jake's cock bumped against my cervix over and again, I grunted in a voice a didn't recognize as my own. It's pitch increased as my need grew. I was at his complete mercy in this position and I hoped to the heavens above that he showed me none.

A part of me wondered what was different this time. The rest of my psyche told it to shut up and hang on for the ride. Who cared why it was happening? It was happening!

"FUCK!" I cried out as felt an orgasm build within me much sooner than I'd expected. "HOLY FUCK!" I was getting my brains fucked out and my little brother was behind the wheel. "FUCK ME!! FUCK YOUR KIMMY!!!!" I screeched like a banshee as his next thrust got me where I needed to go.

I dug my nails into the sheets beneath us in an attempt to remain in the here and now. My orgasm overtook me then. I nearly blacked out from its intensity.

Once I came back to myself, I realized he was still pistoning his cock into my pussy. I gasped and groaned my surprise as my eyes looked up to see an intense look of concentration on his face.

I soon began crying out again as he continued to pound my pussy relentlessly. "Fuck," I said and thought. Who'd have thought... "Fuck me, Jake."

Was he close? Had the condom torn? I didn't know and honestly didn't care. I made a note-to-self to add Clear Eyes to my shopping list tomorrow because I doubted either of us was going to get much sleep tonight.

 

[musicankane]

Kim's screamed had me feeling like a fucking superhero. I thrust into her harder and faster trying to she how loud she could go. Part of my wanted to send her to her husband so fucking hoarse she wouldn't be able to speak to him. I felt primal need pushing me to please her completely and utterly. I didn't even care how it felt for me anymore.

Then she errupted under me. Her cries made my ears ring and her body shook under me. I felt her juiced flow out of her and onto my balls and thighs and I knew I had pushed her over the dge again. I cursed the condom again as I struggled to feel her around me. It was like I only felt friction and it sucked.

I focused hard on my hips as I continued to thrust into her throughout her orgasm. After another moment though I slowed and had to stop completely as I was out of breath. I sat back for a moment panting heavilly. My cock had popped from her and throbbed in front of me like a bar of rubber covered steel.

I shook my head and panted, "Sex is a hell of a workout." I said chuckling. "How am I doing?"

 

[kimberlee]

Jake had continued banging away at me, sweat beading his forehead - dripping from his bare body and onto mine. His body pressed repeatedly against mine and I welcomed his every movement. I cried out his name times too numerous to recall as he drove me from one peak to yet another.

He paused and I noticed two things right then. One, I was panting like I'd run a marathon and so was he. Two, he was still frikking hard as steel.

I had to join his laughter. We were both covered in sweat from our exertions. My eyes were drawn to his condom encased cock. I'd have sworn it had been the one I'd sabotaged; but, I had to be mistaken. There was no way it would have remained intact after the hard driving motions Jake had just done.

How was he doing? I grinned.

"Not too bad for your second go at it," I said with a smile onmy face. "Damn, I can't believe you're still hard." I shook my head in some degree of wonder. I then reached between his legs and tore the latex with my fingernails. "Think you can shoot that load you've worked up deep inside me, sugar?"

 

[musicankane]

I was happy that she seemed genuinely pleased with me. She shifted and sat herself up and I sww her gaze go down to my cock as if surprised it was still there. Did she think I was going to fuck her so hard my dick would fall off? Could that happen? No....right?

I looked over her body and took in again just how beautiful she was. Her body was stunning and it made my balls tingle just thinking about it. When she asked me how I was still hard and shrugged and flicked the condom. "This feels really different. Like everything is kind of numb anddull. I mean you still feel great but this ring is actually painful so it is keeping me from coming close to cuming."

I don't know what I expected her to do or say. Probably "thought shit" or something like that. But she didn't. Instead she reached down and tore the tip of the condom away. My eyes widen at her as she asked if I could cum deep inside of her again. I couldn't believe it. What if she got pregnant? Then again maybe she was on birth control and just wanted me to experience a condom. Now that I had, no reason to keep it on right?

"Are you sure Kim?" I asked as I rolled the condom off my dick. "Ow! FUCK!" I cried as I saw the indent ring shape imbeded on my dick where the condom had pinched me tightly. "Thank god I took that off. Almost sliced me off." I took a deep breath and rose up onto my knees as if to get ready to mount her again. Damn this was a fucking work out.

 

[kimberlee]

I'd expected him to simply return his cock into my pussy. I apparently underestimated the uncomfortableness and even pain caused by the sexual protective item. He rolled the latex down the length of his hard length and tossed it aside. He complained; but, all guys seem to have some sort of inate dislike for wearing the things.

His cock did look a bit the worse for wear; but, I think it was a combination of the rubber and the way he'd been slamming into me. Jake looked exhausted as though fucking me might be a chore.

I halted him where he was and told him to lie down. He'd done enough work tonight. It was my turn to get in the driver's seat - so to speak. Besides, with the orgasms he'd wrung out of me; he deserved a break and his own orgasm.

I rose and straddled his hips, my pussy dripping its juices onto his rod. I carefully lowered myself and soon had his cockhead knocking on my front door. Upon further lowering myself, I captured him deeply enough that I was able to lean forward to capture his lips with mine.

I smiled as he placed his hands on either side of my hips. Our kiss broke and I told him that I also enjoyed having my nipples sucked on. I moved my hips up and down until all of his cock was being absorbed into my inner most depths before I all but lifted myself off of him before taking him again.

 

[musicankane]

Kim rising over me, aiming herself so that she could sit on my dick and have it slide deep inside of her, well it was an amazing sight. Her perfect body was wonderful to enjoy and look at. Then she sank onto my cock and I felt her wonderful walls wrap wonderfully back around me. The huge difference between being inside of her bareback. I could feel her juices coating my skin, I could feel the pulse of her tunnel around me, I felt everything and it was great.

She leaned toward me and we kissed, my shaft pulsing inside of her. Then she shifted and told me to suck on her breasts, which I was only too happy to do. My mouth wrapped around her nipple, my hand came up to squeeze and play with her other breast. I twirled my tongue around her areola, flicking the nipple now and again. The taste of her soft flesh in my mouth just excited me, and my hips rocked under her, grinding myself around.

Then she started to move, a gentle rise and fall of her hips. As my shaft moved in and out of her I savored the feeling of her walls parting and closing around me as I occupied and vacated her body. My balls immediately began to tingle again, as if all that time in the condom had only served to make them angry. Unfortunately Kim's womb was about to get the sperm bomb I've been building up since the shower.

My hands moved to Kim's hips and I urged her to ride me faster. I needed to cum, I could no longer hold it back. I bucked my hips up into her and I felt myself start to explode. I grunted and shook under her, then pulled her down to the hilt as my cum started to burst forth into her. Each rope shot from me almost directly against her cervix, filling her uterus with my thick sperm.

 

[kimberlee]

At first, he played. His mouth licking and sucking one nipple as his closer hand would pinch and tease the nipple not currently receiving his oral ministrations. I almost never used this position, John preferring to be the one directing our moments of passion.

I could feel an electric current pulse from my nipples and straight down to my center. Jake's cock inside me only served to strengthen the overall sensation. I suppose that the fact that I was in charge and openly, willingly riding my brother's cock added something to the mix.

I rose and fell on his hardness, eagerly welcoming him time and again into my channel.

He was different this time. It was as if the condom had held him back somehow and now he was letting himself go. Before, he'd been concentrated on my wants and needs. However, there was an urgency behind his grip on my hips and his upward thrusts into my decending sex. I could see it in his eyes. He was getting close.

Even as my mind registered the thought, he pulled me against him. As he ground his pelvic bone to mine, I saw his back arch and felt his cock swell slightly more before his balls released their load and his cock delivered it into my womanly depths.

I don't recall if I did it or if he did; but, the next thing I knew, I was on my back once more with Jake above me. My legs wrapped tightly around his ass and lower back as he continued to empty himself into me.

"Fuck! How much cum do you have?" I unknowingly said aloud.

 

[musicankane]

I grunted with the force of my orgasm, unable to hold my hips up I forced her to roll over so I could push even deeper into her to unleash my seeds. I buried myself deep as my cock continued to pulse and fill her with cum. I couldn't believe how hard I was cumming either, each pulse into her seemed more powerful than the last.

Kim noticed it to as she cried out, asking me how much cum I had.

It didn't matter because all of it was pouring into her quivering womb. "Years worth Kim." I told her, confessing that many years of build up was now squirting its way into her. All the time I spent looking at the hot chicks at school, never being allowed to talk or flirt, let alone touch.

Now that Kim's beautiful body was free to explore and fuck I was giving her everything I had, and more. I don't know how long I came inside of her, but finally I slumped over her and gently slide off her body, my cock slipping from her following by the thick white cream I had pumped into her.

"Holy crap," I panted staring up at the ceiling. "How the hell am I ever going to be able to jerk off ever again after experiencing this?"

 

[kimberlee]

His release just seemed to go on and on. I wondered if his balls would end up the size of raisins or sunflower seeds. I held on to him as he squirted what he claimed as years worth of unfulfilled need.

I wondered if the condom had held his sperm from ejaculating. I hadn't heard of anything like it ever happening but... I mean, it wasn't gallons; but it was sure more than I was used to. I began to cramp up toward the end. Then he'd pulled out and a good stream of the stuff followed suit.

Thank goodness. I reached between my legs and my fingers came back coated in our juices. I tasted it - not bad.

"Holy crap," he panted staring up at the ceiling. "How the hell am I ever going to be able to jerk off ever again after experiencing this?"

"Think of me," I teased. Honestly though. He had a point. John's and my sex was still active and good; but...

 

[musicankane]

I laughed and nodded, "Yeah totally. You're kind of stuck in my mind now, but then again..." I smiled and rolled toward her. I reached over and ran my finger over her breasts. "Why think of you when I can just do the real thing?" I asked in a mocking smile.

I knew this was going to end after tonight, I knew that she would go back to her life, but I could play with it right? Could I not just have this moment to pretend that she was mine for a while? In the morning I could face reality, but tonight Kim was my sexy girlfriend who liked it a lot when I pumped my load deep into her. It was great.

I took a deep breath and rolled onto my back. "I'm gonna remember this night for the rest of my life." Especially if I had just gotten Kim pregnant. That would definately be a fucking memory.

 

[kimberlee]

It felt like millions of his little guys and gals were swimming inside me. I had to admit that having him shoot into me unprotected felt hot. I mean, I was going to get the morning after pill and all; but, just pretending that I was his girlfriend and something of Jake might combine with some part of me to create a new life sent shivers down my spine.

I was married and a pregnancy wouldn't be a shock to anyone. So what if it took much more after my side of the family, it would still be presumed to be John's.

What the hell was I thinking? I couldn't have Jake's child, if for no other reason than that I'd have to lie to John each and every day. No, he deserved better than that. I loved my husband. While my brother's and my relationship had taken a few unforeseen turns, Jake was still my brother. Any attempts to further the relationship between Jake and his 'girlfriend' was doomed to fail in the long run.

I couldn't quite understand why - given these facts - I still wanted more. Maybe I could call later in the week and see if matters had taken a turn for the better. If not, I supposed his girlfriend could make a showing or two.

Damn, I was going to go to hell for cheating on John and taking Jake's virginity. A tingle ran through me. I was a very naughty girl.

 

[musicankane]

I don't remember falling asleep, but I know that I woke up with Kimberly curled against me, both of us still very very naked. The first time in my life I woke next to a naked woman and it was a cool experience too. I rolled out of bed gently and moved off to the bathroom to relieve myself. As I did my thing, I thought about what was going to happen today. Kim was going home, and I was going home as well. She would go back to her perfect little life, while I would once again be alone.

I suppose it wouldn't be bad, I could play some Warcraft or Diablo and hang out for the weekend. Mom would be off my case as I did what she wanted from me last night. Though I couldn't wait to see if anything that we did at the prom would make any difference at school on Monday. There would most likely be a buzz from the fact that Steve got arrested last night. Considering I was the reason, plus we did take Sarah home, so maybe she might talk to be a bit more.

Hard to say.

I came out of the bathroom and heard a cellphone ringing. I quickly found the phone in Kim's handbag and saw it was her husband John calling. I darted to the bed and shook her awake gently. "Kim? Kim? John's on the phone." I said holding the phone out to her.

 

[kimberlee]

I was having the most vividly bizarre dream. I'd had sex with my brother, Jake, a number of times. My mind drifted through any number of erotic thoughts.

Jake thrusting himself into me then stopping suddenly. He saw something I was unable to. He began shaking me, "Kim? Kim? John's on the phone."

The phone? my mind pondered. He continued until I blinked the sleep from my eyes only to view my brother standing stark naked and holding out my cell phone to me.

It hadn't been some strange dream; Jake and I had...

I sat staring at his naked form before his words truly registered. I took my cell from his proffered hand. It had already gone to voicemail. I listened to the message John had left and called him moments later.

"John?" I asked. The message hadn't made much sense. "No, Jake's fine. Though the car's seen better days," I added. "Didn't you get my Voicemail?"

I listened as John talked about receiving a call from my mother this morning. When she'd gone to collect my brother to eat a late breakfast, she'd found that his bed hadn't been slept in. Worry had set in when she hadn't been able to call me and had caused John to worry as well. It looked like John wasn't the only one who'd forgotten to check their messages.

"Sorry, baby," I said speaking into the phone. "I was a nervous wreck and didn't trust myself to drive last night. Jake took good care of me."

John is the type to catch possible double entendres that might not have been meant and joke about them.

"So, Jake did get lucky with his date, after all," he said.

I froze for a second or two until I heard him laughing at his own joke. I felt a great weight lift from my shoulders.

"Yeah, well, something tells me you won't be laughing when you see the rear fender. And I'd better warn you that I had Jake carry me over his shoulder, out of the prom, as I pretended to cry out for help and called him an animal."

John laughed his ass off.

I supposed now was as good a time as any. He was in a very good mood. "Ummm, it wasn't planned and I doubt either Jake or I could have seen the way things worked out; but, I may have to continue visiting occasionally as his girlfriend. OH, COME ON. IT'S NOT THAT FUNNY!" I finished speaking loudly so he might hear me over his own laughter. "In fact, I plan on going to the store and buying an economy size package of magnum size condoms and a morning after pill among other things."

He finally stopped laughing to ask me, "Don't you think that's taking things a bit too far?"

He had no clue as to just how much farther we'd already gone. With that thought in mind, I peered to see whether Jake was being troubled with 'morning wood.

"Gotta go, hon. Call and tell Mom everything's fine, okay?" With a few words of thanks, I closed my phone and handed it to Jake.