Bro and Sis – The First Time of Many

“Dammit, it burnt again!”

“That’s because you never check how high it’s on, Hailey. You know dad likes his toast char broiled!”

“Well, Keith, you have a point, but in my defense, he could just as easily change it back when he’s done,” Hailey replied.

“Let’s just be thankful they will be nowhere to be found for the next two weeks.”

“Thank you, Grandma,” I mutter with my hands clasped toward the air.

You see there are several categories of parents, like so; You have your “happy medium,” parents. They’re the ones that always take their families opinion before making depictions. Let their spoiled offspring get whatever clothes they want to wear. Oh, and they always seem to be going on vacation every other weekend. This causes issues, most often involving the kids pinning their parents against each other, eventually resulting in a broken marriage or not one at all.

Then you have your “strict overbearing” parents, unfortunately that’s the category my own fall under. They never take what I have to say in consideration, they have make plenty of money and think the clothes I like are “too expensive”. They think allowance is a form of communism, and they also hate everything I’m interested in. When I say them, I mean my dad. My mother is cool when Dad isn’t around, but unfortunately is pretty whipped when he is.

Finally, they don’t trust Hailey or I a bit! Which is the shocking part of the whole trip. Come to think of it, should I be worried? Oh and there is one more category. The “passive aggressive” parent, they are the biggest pansies in my opinion. Their kids walk all over them, and get everything they want otherwise all hell breaks loose. Ah yeah, wouldn’t that be nice. Sadly this often results in the same thing as “Happy medium”, but top it off with an alcohol or drug problem. Hell, it’s 2013, probably both. 

So I should tell you a little about their trip. Ten words are enough to sum up the important details: Two weeks’ island hopping, to Jamaica, Hawaii, and the Bermuda triangle. What if Mom and Dad just happen mysteriously disappear in the ol’ Bermuda? I thought. One can only dream I suppose. I’m kidding, a little. While I was caught in a daydream consisting of what I would do with such freedom, my Dad barged in my room, without knocking, as usual.

“Why is this kitchen such a mess, it’s not even eight o’clock and you’re already tearing up my house, and what’s that shit-eating grin for, Keith?”

I adjusted my face and posture, as I didn’t notice the smile that occurred from my deep thoughts. “Oh nothing, I was just thinking about how beautiful of a day it is,” I said nervously, with my eyes wide and shoulders hunched.

My father sneered inquisitively at me, as if he knew what I was up to already but I don’t even know what I am up to yet. To say the least, Dad is a scary individual. He is fit, 195 lbs. and built, and he’s where I get my sharp jaw line and piecing blue eyes from.

“Well it better not get too beautiful, and if I’m not being clear enough, I’m referring to anyone being over here while we’re gone,” he said with one hand on his hip and the other panning back and forth between Hailey and I.

This was a classic pose of my dad’s, I think he was under the impression he was conveying his assertiveness through this stance. Every time he did this I just imagined if his hand was positioned the opposite direction on his hip he would look mighty gay to me. This thought always had me struggling to hold back one of my “shit eating grins”, as Dad would put it.

“I want this kitchen cleaned before you leave for school, and remember, this weekend, no one is to be over! Better yet, so I know you’re not breaking curfew you guys have to be back by eight o’clock every night. I will be calling the house eight sharp and I better get an answer.”

My dad walked out of the room with this prissy shit eating grin of his own. I ignored his delusional control-freak attitude, and started wiping the counter top. 

“I will help you when I am done,” said Hailey, as she brought her chewing to half speed.

I raised an eyebrow at her. “Fine, I might as well make sure it’s done right,” she said stuffing the remaining bit of toast in her mouth which seemed to big.

“Pig,” I said playfully.

“Dick,” she replied, muffled by a mouthful of bread.

“Why do you care anyways? Dad won’t be here to check?” I asked.

“Well, because tonight is going to be the first time the girls have ever been able to come over!” she said excitedly while clapping her hands together.

“Hailey, you heard Dad, No one is to be over, like usual.”

My sister rolled her eyes at me. “Oh, Keith, live a little okay?” she said placing her hand on my chest and skipping away and up the stairs.

I sat there thinking about what she said. My parents were going to be across international waters, maybe I should stop being so paranoid.

“Hey! I thought you were going to help clean!” I yelled after realizing she just waltzed on out without even rinsing her plate off. I heard the upstairs bathroom door open and saw light shine across the railing.

My sister leaned over the railing. “I have to shower and do my hair. How about I make it up to you later,” she said winking at me.

“What? You going to finally hook me up with one of your cheer mates?” I said with a curious look.

“Maybe,” she said and just then, I noticed my sister was in her bra as she reached behind her back to unhook it.

She dipped out of sight just as the straps fell to her elbows. I heard the bathroom door shut followed by the sound of the pop music coming from behind it. You know, I knew it was wrong to look at your sister this way, but she had quite a sexy body. We were twins anyway. We were extremely close and had been naked around each other quite a bit throughout our lives. If any of her friends coming over tonight had half the looks she did, I wouldn’t mind a bit. 

About fifteen minutes passed and I was almost done with the sink full of dishes. Suddenly my face went flush, my heart sank into my stomach, and I got a serge of hot and cold through my body. The cause of this was my dad grasping my shoulder with an intimidating firm grip. I didn’t hear him on account of the dubstep blaring in my ears.

“What’d I tell you about listening to that shit so loud, I’ve been calling your name,” he said while grabbing an apple and banana off a clear dish on the island.

The adrenaline subsided as I noticed the backpack my dad was carrying. I quickly turned away from my dad to prevent him from seeing the uncontrollably excited set face I was making. Ranging from relief, to overwhelming joy, and finally salvation. I know, it sounds a little dramatic, but you know what they say, “Try walking a mile in my moccasins.”

I scrubbed my last plate clean, rinsed it, and before I knew it my my mom was racing down the stairs with a pair of shoes in both hands. She was in such a rush she almost tripped. My Dad was notorious for many things, and one of those was his ‘last minute call’. This was where he yelled obnoxiously that you had one minute exactly to be present down stairs, or you’d be left behind. My mom had good reason to be rushing, because he’d actually leave you. He once left me because I was grabbing a water bottle out of the fridge, and we were going to my soccer game. 

I turned off the sink and dried my hands. I anxiously sat on the arm of the couch staring at the garage door. The last bit of light faded from the crack of the door and the sound of the garage door touching back down rang through my ears. I had a little celebration, consisting of dancing and chanting the freedoms I would experience over the next two weeks. My sister threw open the door and started cheering, twirling and clapping herself.

“Not bad, did you prepare that?” I asked chuckling.

“Actually, I made that up the night I found out they were leaving.”

“Nice,” I said while we both busted up laughing.

“Hey! What happens this weekend stays between us okay?” my sister said, raising an eyebrow with her hand on her hip.

“You read my mind,” I replied. 

I started heading up stairs and I saw my sister casually walk from the bathroom to her bedroom. I also noticed she was wearing only the booty shorts she wore for cheer practice. My 17 year old hormones took over as I examined her nicely tanned back progressively moving toward her plump butt covered by a thin layer of bright yellow spandex. Again my ADHD sent me into another day dream, leaving me standing at the top of the staircase. I snapped out of it just as my sister walked through her doorway toward the bathroom. I got nervous, as if she knew what I was thinking. She still had nothing covering her chest and looked at me.

“This is going to be so much fun, you better get ready!” she said.

Not thinking to put the bra on she was holding my sister was a little more open with her body than I was. I was embarrassed to be naked in front of her because I thought she might think I had a small dick. I caught my sister downstairs at night completely naked at least once a week. She thought nothing of me being there. In fact, she once wrestled me over the last bowl of ice cream, with just a thong on. She won and I walked awkwardly upstairs avoiding having to face her, if you catch my drift. 

After getting dressed I went in my dad’s bathroom to use some of his cologne. I opened his medicine cabinet, making sure to keep everything in its place. My Dad had quite the eye, especially for his stuff! Next to this shiny silver bottle of cologne that caught my eye was a prescription bottle. I read the label and didn’t recognize the name. However, I did recognize the name the bottle said it was generic for.

“Viagra,” I gasped following with a grin.

No wonder he acted like he needed to prove his manhood, I thought while I had my laughs. I opened the bottle a poured out a few of these blue little guys.

“The bus is here!” I heard Hailey yell, which startled me enough to drop the prescription bottle into the sink.

The pills went everywhere. I gathered the majority thinking I would just clean up the rest later. I replaced the bottle and jetted out the door.

School was slow but didn’t seem to bother me much. The thought of the house to myself afterward was too good for anything to squash. I figured I should invite at least one of my friends tonight. You know, a wing man. I couldn’t have too much meat at my place tonight, I wanted the odds in my favor. There was one guy who I trusted enough to assist me on this momentous occasion. Joey! My man. We had been friends since diapers. Our Moms met in birthing classes. He lived not two blocks away from me. After the bell rang for lunch I headed to Joey’s and my spot. I got a little anxious waiting for Joey because I hadn’t seen him all day and he was late. Finally Joey showed up.

“Joey you like shit, bro!” I said as nice as possible.

“Yeah bro, I knew last night I was going to wake up sick,” he replied.

“You can’t be sick today, I need you tonight bro!” I said franticly.

“What’s so important on a Thursday night?” he asked.

“Well, Hailey, just happened to have invited her cheer friends over tonight, plus you know I have been waiting for that two weeks of freedom I have been going on about. I need a wing man, bro!”

“I am feeling a little better, now that you have stated the need of my assistance,” he replied chuckling. My laughs followed.

Let’s fast forward a bit, to the end of the day. 

We picked up in my living room after school. Hailey was there when Joey and I got there. Her friend Ashley was there as well. She had dark brown hair, almost black, with hazel green eyes and the whitest teeth you’d ever come by. Her boobs were smaller than Hailey’s, but her ass was so fit. She wasn’t even my favorite of my sister’s friends.

“Hey, Keith,” said my sister quite pleasantly.

“Hey, Hails,” I replied.

“Hails? You haven’t called me that in forever,” she said giggling.

She was right. My sister and I normally got along pretty well when we were alone, but never in front of friends. It probably had to do with the lack of pressure due to mom and dad being gone, I thought.

“What’s wrong with Joey?” asked Hailey.

As I looked over to him, he seemed ten times worse than first thing this morning.

“I don’t know if I can do this tonight, bro.” Joey moaned.

“Nah, you will be fine we will just get you some Tussin and a nap and you will be good as new,” I pleaded.

“I don’t think cough syrup is going to do anything for what I am almost positive is stomach flu. I mean do you really want a barfing wing man,” Joey pleaded as well.

“Come on, bro, will you just take a nap at least and see how you feel. You can go home if you feel too shitty, I promise,” I proposed.

He accepted as he left without saying anything and made his way to the guest bedroom.

Chapter 2 

Pool Side beginnings 

While Joey slept and missed out, I was pool side with my sister and her hot friend. “So, Ashley, how long have you been a cheerleader?” I asked.

“Keith, your sister and I started at the same cheer camp. How could you not know that when my brother is your best friend?” she said laughing.

Oh! Did I forget to mention that Ashley and Joey are brother and sister as well? My bad, but that is quite convenient isn’t it?” I gave a obviously fake laugh to avoid being silent.

“Come on let’s go in the hot tub!” Hailey suggested.

The best idea all day, I thought to myself. I was the first one in. As I sunk to the cement seat, my bright blue bathing suit puffed in my crotch. I pushed it down with my hands and of course bubbles followed. But I don’t think the girls noticed the inflated crotch part. Just the bubbles surfacing next to me.They both chuckled, as I sunk till the water was between my chin and shoulders.

“Let’s just turn these on shall we,” said Hailey.

Suddenly a stream of hot water struck my back and thighs, soothing my nerves enormously. Hailey smiled and winked at me again before she got in. Was Hailey turning out to be my wing man? I thought. As the girls began to rant and gossip uncontrollably. I lay my head back against the stone edge of the hot tub. 

I opened my eyes and the girls were gone. I must have fallen asleep I thought. I rubbed my eyes and could tell I had been out a while due to the pruney texture to my fingers. I got out and ran to the back door because a steady gust of wind was making it rather nippy. I knocked on the back door, and after a cold five minutes Hailey came around the living room corner noticing me.

She put her hand over her mouth to hide her laughter. “How long have you been standing there?” she asked.

“Long enough,” I replied, as she grabbed a towel and threw it around me.

“Here take off those trunks, I will hang em up,” she said.

Great I thought, the one time I don’t where boxers underneath.

“Hello, do you I have to take them off myself? You will get warmer much faster!” she said laughing. “I’ll hold your towel,” she said.

I took a deep breath and and pulled my trunks to my ankles. When I stood up straight, Hailey totally double took looking at my dick.

She looked impressed. “Cleaned up the pubes I see,” said Hailey with a grin on her face.

“How do you know I trimmed up?” I asked looking confused.

“Same way you know my pussy is bald,” she said.

“We have a conjoined bathroom, and sometimes when I can’t sleep I lay on you recliner in your room, and you sleep naked,” she stated without hesitance.

I sat there slightly shocked, and my facial expression reflected so. “Come on don’t act like you never checked me out,” she said laughing. “Plus we are super close, I think it’s completely natural.”

“You’re right, and I mean we have seen each other’s bodies develop, so it’s not like there is anything we haven’t already seen.”

She nodded with a smile on her face and turned to walk up stairs. “Plus, seeing that tiny mole on you inner thigh under your right cheek, cracks me up. No pun intended,” I added. She snapped back looking at me laughing with her jaw down. “Wow you must of been looking pretty hard to find that, a couple of my boyfriends didn’t even notice that. She said with a smirk on her face. 

After putting on some dry clothes, Hailey and I returned down stairs to the living room. There were now about six more girls here and I was still without a wing man. I checked the guest room and Joey was sound asleep!

“Just relax,” Hailey said nudging me with her elbow.

We joined the group on out wrap around couch. My sister went through a lot of trouble. Because she had chips, salsa, veggies and dip on the coffee table.

“Dig in, I fixed that up while you were asleep,” Hailey said.

“Okay, Ashley helped too”, she added chuckling with Ashley.

“It is hot in here, Hailey,” said my sister’s friend, Kendra.

“I know right,” replied Hailey.

I offered to turn the A/C up, but when I approached the thermostat, it was flashing messages that said, “Freon too low. Perfect I thought, just after they leave. “I am so going to get blamed for this,” I muttered aloud to myself as Hailey snuck up behind me.

“D’you get that A/C turned on?” she asked.

“Well we have a problem. We are out of Freon,” I said rather bummed.

“What does that mean?” she asked.

“Freon’s what cools the air blowing through the vents, and without it. It’s only going to get hotter.”

“Well, what should we do?” she said with concern.

“I don’t know, we’ll have to call Dad,” I said regrettably. 

So after thirty more minutes, seven degrees hotter, and no way to cool the house or the winning coming from all the princess cheerleaders we decided to call Dad. I dialed the number and waited for the ringing to stop and the yelling to start.

My Dad answered, “Hey, son!”

I looked at the phone confused and brought the phone to my ear, muttering, “Hello?”

“Keith, my boy,” he shouted again.

It was definitely him , but it wasn’t my Dad, if you catch my drift. He was drunk and in a good mood. I told him the quandary and he said he would called a guy out to fix it the following day. “Just go out in the pool for a while, that will cool you off”! he suggested, which we did after two girls left because they ‘Couldn’t take the heat.’ That meant we were down to four girls now. We all were in the pool for about five minutes, before Stephanie said it was too cold. We switched to the hot tub. Then it was too hot. After two more increasingly annoying rotations the remainder of Hailey’s friends decided they were going to leave.

“Maybe tomorrow after you get the A/C fixed we can come back,” said Stephanie, as her and the other girls walked out the front door. Ashley was the only one who stayed. But she was about falling asleep on the couch already. So it wasn’t long before she joined her brother in the guest room.

Chapter 3 

It’s Getting Hotter and Hotter 

Hailey and I both sat on the couch with the obvious look of disappointment upon our faces.

“I thought I was going to get laid tonight,” I sighed.

“Hey, you’re not the only one Keith,” added Hailey.

“What? Were you going to hook up with Ashley or something?” I said not very seriously.

“No, there was this guy that was supposed to come over,” she said with a guilty smirk.

“Who?” I asked.

“Oh nobody really, his name is Justin,” she replied.

“You mean Justin Woodman?” I said like a smart ass.

“Yes,” she replied with a look that said she wished she had just kept her mouth shut.

“You wanted that guy tonight? I could do ten times better of a job than him,” I said without thinking twice.

“You could do what ten times better?” she questioned with her arms crossed and eye brows razed.

I couldn’t think of how I should respond, I just stood there staring at the smirk she was giving me. Then she asked me flat out, “You think you could fuck me ten times better than Justin.?” We both busted up laughing.

“That’s crazy,” I stated in the midst of our laugh.

“Yeah, your dick’s only a little bigger than his, what difference could it make?” she said casually.

My laughing began too slow. “You think my dick is big?” I asked trying to reserve some of the eagerness in my question.

“I didn’t say that, I said it’s bigger. I could think Justin has a small dick.” I sat there a little embarrassed. “I’m kidding,” she said as she threw herself into me placing her hand against my chest. She stood up and walked toward the fridge. “You want some lemonade?” she asked while taking her shirt off, revealing a baby blue lace bra underneath. “It’s so hot!” she added.

“Sure,” I muttered as a frog in my throat began to fester. Her back was facing me as she filled our cups. The light shining from the fridge’s open door contrasted her ass with the darkness surrounding her in the kitchen. She was wearing the same spandex shorts as early this morning, only these once matched her bra. She return to the couch handing me my drink. I brought the glass to my mouth, detecting a faint scent of alcohol before I took a swig.

“Trying to get me drunk are you?” I said jokingly.

“I thought you might enjoy a relaxant after the crazy night,” she replied while lying back and throwing her her leg over my lap.

Suddenly, I felt excited, you know the way you’re not supposed to from your sister. My heart started to race as I looked over at her. She was drinking quite steadily, which was probably good at this point. Any numbing of her calf would be obliged, I thought. I could feel the blood rushing. Unfortunately it was in no control of mine to stop it. I sat there hoping she would not notice.

I didn’t want her to feel me getting a boner, but for some reason the risk of that occurring was worth the excitement I was receiving from this. Suddenly she rolled onto her side and reached toward the coffee table to set down her now empty glass. I then noticed that I hadn’t even touched mine, I had been a little distracted. So I felt chugging the whole glass at once would be the most logical course of action to carry out next. Which I did, and experienced series of faint heaves and shivers.

As I pulled the glass from my lips, I looked over at Hailey and noticed she never turned on her back after she set her glass down. She just lay there on her side with her leg across my still rising member, her ass silhouetted by the television with flickering colors scattering over perfectly tan skin. 

The alcohol started to kick in and soon after I was pretty buzzed! We lay there for a while not saying a thing. Just when the silence began to feel comfortable she made things even harder if you catch my drift. She rolled off her side onto her back, throwing her legs into the air.

“Correct me if I’m wrong, but it’s just getting worse,” she said sliding her spandex shorts under her ass and up to her ankles.

I look down at my now exposed boner, looked back over at her only to be greeted with the sight of camel toed lips beneath her thong.

“You don’t even know,” I replied wiping my hand across my forehead.

She might as well have not been wearing panties with the detail of her downstairs dimensions. It seemed to take forever for her legs to descend from over her head. Once they did, both of them were now on my lap. The gap between her legs was where my rock hard dick hid. She began flipping through the TV guide. “Where are the pay per view channels?” she asked.

“I don’t know, but do you think that is a good idea to order something, Dad will see,” I said feeling like a party pooper. “What were you trying to watch anyway?” I asked.

“I don’t know, maybe a comedy, horror, or some porn,” she said with a face that implicated no sense of humor in the her suggestion.

I was getting another frog in my throat. Before I could think of something to break the silence, she did just that.

“So, what type of porn are you into because we have a lot to choose from,” she said pointing at the screen with the remote.

I looked up at the screen breaking eye contact with her body for the first time since she took her shorts off. I noticed we were in a catalog of porn.

“Teens, Mature, Amateur, MILFs, Taboo. Taboo, huh?” she said after finishing her increasingly erotic listing.

“I wonder what that is,” she said choosing to continue into that selection 

She read the first title aloud, “Sister caught masturbating by brother.”

We both looked at each other, her less worried than me as she began to laugh. I laughed as well to prevent any more uncomfortable tension from arising. Oh, speaking of rising, she was starting rub her legs back and forth on my lap and she grazed my head every time. The video finished buffering and we saw a teen girl dancing in front of her webcam naked. She had music on and a chair in the middle of the room. After grinding against the chair for a bit she grabbed a purple dildo off screen and started rubbing it on her pussy lips.

“Ooh purple, same color as mine!” said Hailey.

My cock began to throb and pulsate between her legs so much that she said, “Someone’s enjoying the video, I see,” giggling adorably.

The girl on the video then sat on the dildo and started a full-on penetrating ride. Up and down she thrust herself, striving for the base of her toy. Suddenly, a guy her age opened the door. He looked shocked, as did she, putting her hands between her legs and rushing to turn off the music. You couldn’t hear but the brother said something to the sister and the video ended. Hailey and I start laughing. “I wonder what happened after that webcam stopped,” she said.

“What do you mean?” I replied.

“Well I mean, did she feel extremely uncomfortable and avoid him, did she get to finish.. Did she let him help her finish?” That last question made me look her directly in the eye. She smiled.

“Let him help?” I asked.

“Yeah, I mean if she was maybe lonely and needed someone to console her, fulfill her needs. I think that falls under brotherly duty. You know making your sister happy. Don’t you?” she asked.

“Yeah I think so,” I replied unsure of what she wanted me to say.

“Kind of like how tonight you were supposed to get laid. I Brought so many friends over tonight to help you. Because that is what sisters do, fulfill your brothers needs, but now you’re just sitting here with me with a hard on and no pussy you want to fuck.”

Every word that left her mouth made me just want to tell her what I really wanted, but as usual she beat me to the punch. “I mean, there is more I can do to help, but I don’t know if you would even consider it.”

My heart leapt as I almost shouted, “What!”

“Well, I have been on birth control for a while now, so I could safely relieve the tension.”

I sat there shocked that this conversation was occurring. Without a reply from me she raised her legs above her head again. She pulled her thong toward her ankles revealing a moist and tight pair of lips. I could she her juices drip down her. She leaned up and flipped on her stomach facing me. She pulled my shorts down below my dick. I had no time to react. Her tongue was pacing across my head and shaft, while her lips reached toward the base of my dick. She pulled my dick out of her mouth slowly, swirling her tongue over the tip of my dick.

I squirmed a little shocked from the sensation. I figured I’d better relax and let it happen. She ran the tip of her tongue up and down the backside of my dick, occasionally blowing in and then submersing my head to the back of her throat.

Finally I felt her stop, I kept my eyes closed, laying on my back. I could feel her re-positioning herself. Suddenly I felt her legs on both sides of my waist. As I looked up she plunged down on my dick. I sank deep inside her. She went down as far as she possibly could before pulling her ass back up.

I could feel how bad she wanted it. Her pussy tugged on the surface of my dick, swallowing me deeper again and again. Finally I wanted to call some shots so I grabbed her hips and plowed myself into her rapidly, pulling her away and toward me. I was fucking her so fast my balls started slapping her ass.

When her moan was almost done turning into a squeal, I thrust once more deep inside of her holding there for minutes it felt like. I could feel her pussy throbbing around my cock. She lay across my chest with her arms close between us. I had my arms wrapped around her still pulling her down on my dick. The tip of my dick got real warm all of a sudden and she her thighs began to quiver.

She moaned quietly but very passionately. She dug her nails in my chest and continued to convulse on my dick. Just before she was able to calm down. I felt my sensations get increasingly intense. My jaw dropped as I contemplated telling her. I slowly started thrusting ever so gently, and then it happened. I pulled myself into her again this time, filling her with the warmest fattest load I have ever experienced.

She began to shake more intensely. Finally she lifted her pussy up off my dick, moaning loudly as she squirted all over my dick. She fell into my chest crying in pleasure. She continued to drip all over my balls. It was so warm. My drenched dick lay between the crease of her pussy. That concluded our first night alone with out Mom and Dad.

To be continued ….