An Ordinary Teenage Sex Life - Cover

An Ordinary Teenage Sex Life

Copyright© 2008 by bluedragon

Chapter 9: Sister

Coming of Age Sex Story: Chapter 9: Sister - A teenage boy learning about love and sex with his cute classmates, gorgeous cheerleaders, friends at summer camp, a beautiful neighbor, and even his own sisters.

Caution: This Coming of Age Sex Story contains strong sexual content, including mt/ft   mt/Fa   ft/ft   Mult   Consensual   Cheating   Incest   Brother   Sister   Group Sex   Oriental Female   First   Safe Sex   Oral Sex   Anal Sex   Pregnancy   Cream Pie   Big Breasts   School  

DECEMBER 2000, WINTER BREAK

"Mmmmmmph!" Cassidy pulled back and smiled at me. "I love you, Ben!"

"Love you too, Freckles. See you next year."

"Mmmmmmph!" Megan backed her lips away from mine and grinned. "I love you, Ben!"

"Love you too, Megan. Call me as soon as you get home."

"Will do."

And then I waved at both girls as they walked across the parking lot to their cars. I sighed. After four days straight of the most mind-blowing sex, thankfully absent of any further politicking between the girls, I was NOT looking forward to a week without either one of them. And despite the pleasantness of the past week, I knew that something in our relationships would be radically changing once they both got back and we all sat down to have our "talk".

But that was more than a week away. For now, it was just Winter Break and after the strain of finals I was looking forward to some time to just unwind. If nothing else, I actually missed hanging out with my sisters and Eden and Emma had been whining about how I paid them no attention this past week.

"Byeee, Bennieeee..." came the teasing female voice behind me. I turned to see Brooke miming kissing thin air with lots of tongue and I rolled my eyes. Well, SOME little sisters could be nothing but annoying.

"Come on," I waved her towards the parking lot. "Let's go home."


"So you got assigned taxi duty?" Brandi, my older sister, grinned at me. She was standing outside baggage claim at John Wayne Airport when I pulled up and then ran around to greet her with a friendly hug.

"Yeah. Mom and Dad said if they provide the car, I've got to drive wherever they want, whenever they want. I live to serve."

"Fine. You may take that, my good man." Brandi looked down her nose at me and pointed at her heavy suitcase.

Chuckling, I stepped over and hoisted the thing up, dropping it into my trunk. "Just don't expect me to hold your door open for you," I drawled before returning to the driver's side.

Brandi just grinned and hopped into the passenger side. Soon we were off for the short trip back to the house.

"When do you fly back up?" I asked as I merged with traffic for the loop back to MacArthur Blvd.

"Not until January 21. Cal is off for a full four weeks!" Brandi bragged.

"You suck," I moaned. High School resumed in two weeks.

"So how's the love life? You still with Megan?"

I grinned. "You wouldn't believe me if I told you."

"Try me."

"Okay, but you have to swear not to tell Mom and Dad. They don't know the details."

"Sure, whatever," Brandi waved carelessly towards the window.

"I'm dating both Megan and Cassidy."

Brandi snorted and gave me a look. "Both of them?"

I grinned and nodded.

"How the hell does THAT work?"

I sighed, remembering all the drama. "Honestly, not all that well sometimes."

"Good grief, Ben," Brandi chuckled while shaking her head. "Didn't you learn ANYTHING from Dawn and Dayna?"

I arched an eyebrow. "What do they have to do with anything?"

Brandi adopted her big sister look of wisdom. "Two girls is dangerous, Ben. I've seen some guys try to pull it off at Cal. DISASTER every time. You lucked out that Dayna was willing to step back for her little sister, otherwise Dawn might not be your best friend anymore right now. I don't know if you're going to be so lucky with these girls."

"And what do you know about dating? You seeing anybody right now?"

Brandi smiled. "Yeah ... there's this one guy..."

"You sleeping with him?"

"Ben! You can't ask me that!" My sister looked positively scandalized that her little brother would ask such a question.

I shrugged. "Hey, I'm more than happy to tell you I'm banging two chicks at once."

"That's because you're a GUY. You actually get bonus points for that. Girls just get labeled sluts for putting out too easily."

"Fine, fine," I rolled my eyes and focused on the road. Taxis always tried to cut people off on this turn getting to the 405.

"And NO, I'm not sleeping with him," Brandi went on to clarify. "We just started seeing each other ... but ... I'm not that kind of girl. I'm not sure about him just yet, and I don't want to get a reputation. It's bad enough being associated with Dayna, Miss I'm-at-college-and-I-want-to-party-all-the-time. She's already on her fourth boyfriend in just one semester."

"Fair enough." I nodded.

It was more than a minute later when Brandi said softly, "Still ... it would've been really nice to get laid."


Our parents were suitably happy to see Brandi when we arrived, hugging her and talking about how they were oh-so-proud of their "college girl". Both parents then promptly sat Brandi down and grilled her for over an hour about all the changes made to the campus of their old alma mater.

Brandi moaned about the football team going 3-8 and losing the Big Game against Stanford 36-30, of which Mom and Dad were suitably depressed as well.

Sometime around the 45-minute mark, I wandered in and Brandi looked at me pleadingly to rescue her from our parents. I just grinned and kept walking, being the bastard of a little brother that I was.

Late that night, I finished up the video game I hadn't played in over a week. The rest of the house was quiet since it was close to midnight, and yawning I decided to finally take a shower and go to sleep.

Even thought I'd gotten laid more times than I could count in the past several days, I was still horny and terribly missing my girlfriends on this first Friday without either one of them. I knew I'd be in for quite the jerk-off session in the shower to relax myself before I went to sleep.

I was used to being the only one in the house still awake at this hour. And so it was without further thought that I crossed the hallway wearing nothing but a towel around my waist and went to open the bathroom door.

Only the knob wouldn't twist. It was locked from the inside and in confusion I jiggled the knob a few more times, wondering who the hell was in the bathroom at this hour. And as I stared dumbly at uncooperative knob, the door suddenly popped open to reveal my older sister standing there with wet hair and her own towel wrapped around her torso, tucked between her cleavage and just barely falling below her crotch. "Ben?"

"Oh, uh, sorry ... I didn't realize anyone else was still awake."

Brandi smiled at me. "College hours. I can't sleep before midnight anymore." And then her smile turned into a grin as she realized my eyes were roving hungrily up and down her body, trying to glimpse a little more flesh. I hadn't forgotten her occasional naked streaking across the hallway from the past summer.

"Hmph, same old Ben," Brandi chuckled. "It's too bad you were such a bastard before, not rescuing me from Mom and Dad when I needed you. If you had, I might've rewarded you tonight."

My jaw dropped and with that, Brandi strode out of the bathroom and calmly sashayed over to her bedroom. I turned and followed her with my eyes, and just before she closed the door, she turned her head sideways to make sure I was looking and then dropped the towel to the floor, flashing me a wonderful view of her naked back and exquisitely tight ass.

And then the door closed and she was gone.

I blinked several more times before finally stepping into the bathroom and turning the shower on. Now I had one more image in my head to jerk off to.


Saturday was the first full day of winter break, so I spent most of it asleep.

But once I did wake up, I found that everyone was splitting off in their own directions. Now that school was out, all us kids were eager to hang out with our friends in a purely social situation. Brandi had arranged to meet up with her old High School friends, I was playing basketball with Kenny, Daniel, and the boys; and the younger siblings were heading to the mall. Even Eden and Emma were going off to visit friends.

As the two kids with driver's licenses, Brandi and I were assigned to drop everyone off and arrange pickups before heading our separate ways. So my sister and I sat down and worked out all the scheduling while also commiserating over how much of a drag it was to have to chauffer the rugrats. And when my big sis lightly punched me in the arm as we parted, I couldn't help but realize ... she was FINALLY treating me as an equal.

Maybe it was because I was taller and heavier than her. Maybe it was simply because I had my own license. But I certainly remembered all the "big sister" condescension I used to get from her. In the old days, when Brandi and I were assigned to complete some chore together, she immediately took charge, made all the decisions, and then bossed me like an angry tyrant. But today, we worked out the schedule together and when Brandi asked me to drive clear across town to pick up the twins because she wanted to stay out an extra half-hour, I told her "no" and she simply shrugged and caved. The old Brandi would never have compromised.

Something had happened while she was away at college. I became the lead kid in the family, riding herd on my younger siblings. And Brandi had gone from the social elite of being a High School Senior in town to just another anonymous freshman at a big University with over 30,000 students. The way we interacted with people had simply changed. I'd grown a spine and she'd picked up some temperance.

It was a whole new relationship for the two of us.


Later on Saturday night, I found my hands getting a little twitchy as I played video games, and the twitches weren't coming from too much button mashing. I was horny. Hey, I was sixteen. I was ALWAYS horny.

The twins had fallen asleep long ago and Brooke had gone to bed around 11pm. It was just after midnight now, and I turned the volume down on the TV so that I could hear the upstairs shower running. There could only be one person up there, and with memories of the previous night and Brandi's summer teasing, I found myself yearning to be in that hallway when she emerged.

Abruptly, the shower turned off and the sound of water rushing through the pipes faded away. Without a second thought, I turned off the video game and hustled up to my bedroom to quickly strip down and wrap a towel around my waist. I figured my own need to take a shower would be my only reasonable excuse for why I was waiting in the hallway.

Sure enough, two minutes after I got myself into position, the door popped open and Brandi stepped out with her towel wrapped around her torso, coming to a sudden halt in surprise when she saw me waiting.

Trying to keep my eyes from wandering, I stammered, "Uh, just waiting for my turn." It was a line I'd mentally rehearsed three times already, and I winced as even I heard my weakly forced delivery.

"Riiight," Brandi drawled, clearly not buying my excuse. Then an impish smirk crossed her face and she quickly looked both ways down the hallway, making sure that all doors were closed. And in a soft voice, her eyelids half-closed as she murmured, "You're looking for another free peek."

I gulped and blushed, caught red-handed. The tent forming in my towel only added to my embarrassment.

When my eyes went back up, I saw that Brandi was looking a little flushed herself. Her dark eyes were stormy as she glanced over my body, ogling me just as much as I wanted to do to her. Her tongue darted out and crossed her upper-lip, a gesture that I remembered from Keira as one of the signs of arousal. And my heart started racing faster as I contemplated what that could mean.

Without another word, Brandi then stepped forward and grabbed my hand. She glanced around the hallway again to make sure the coast was clear, and then hurriedly she dragged me into her bedroom and shut the door.

Now my heart was pounding and I was breathing hard with anticipation and anxiety. I was in my sister's bedroom. Alone. Wearing nothing but a towel. Brandi turned to face me and in a husky voice, she said, "Here's the deal: you show me yours, I'll show you mine."

My eyebrows went up, but Brandi's gaze was entirely on my crotch, where the towel was being pushed out rather obscenely. "C'mon, Ben," she added when I didn't immediately respond. "Nothing we both haven't seen before."

In a husky voice of my own, I nodded and said, "Okay," and my hands went to the fold that was holding my towel around my waist.

Brandi picked her gaze up to my eyes in alarm, her chest rising as she was breathing hard as well. "But just to look. We're not touching or anything, got it?"

"No problem." And with a flick of my wrist, my towel dropped to the floor. Semi- consciously, I thrust out my pecs and tightened my abs, which had the side-effect of making my hard erection bob just a bit.

Biting her lip nervously while staring straight at my dick, Brandi flicked her wrist between her breasts and then her own towel fell, revealing those round tits that sat high on her chest, capped by small, dark nipples. Her tummy was toned and lightly muscled, and my gaze dropped all the way down to her shaven pussy and lithe legs. I think my dick grew an extra eighth of an inch.

I'm not sure how long we stood there and stared at each other. I did know that the longer I stared, the closer I wanted to get. Hell with closer, I wanted to get my dick INSIDE of her. Sister or not, Brandi was a babe.

But the instant my resolve crumbled and I took half a step forward, Brandi turned away and looked at the floor. Her whole body was shuddering and she said in a thready voice, "Go take your shower, Ben."

For a few seconds, there were no sounds but that of both of us breathing hard. Then with a sharp inhalation on my part, I grabbed my towel and left the room.

When I jerked off in the shower that night, Brandi was the only girl in my mind.


Sunday was calm enough. It was Christmas Eve and by family tradition, we all stayed home to hang out together.

We found some movies on cable and I soon found myself on the big couch, surrounded by little sisters as both Eden and Emma decided to use me as a backrest. Brooke took the opportunity to stretch out on the wing chair, draping her legs over the left armrest. My parents were on the loveseat together.

Sometime around 2pm, Brandi awoke and meandered in during the movie with a steaming cup of coffee. Without a word, she squished Emma closer to my side and then settled into the vacant spot. When I glanced at her, she just smiled casually and without any tension between us. It was as if our little moment last night didn't matter.

I smiled back and looked around at my siblings and parents, all relaxing and enjoying a movie together. It was a pleasant little 21st century family moment.

Afterwards we played some board games and generally killed time while waiting for midnight. Family tradition said that we could all open one present at 12:01am on Christmas Day, and then we had to let our parents sleep in until 10am in the morning. Mom and Dad said it was because Brandi and I had gotten into the habit of waking them up at 5am when we were little, arguing that since it was already Christmas morning we could open our presents.

Eden and Emma actually dropped off to sleep for a couple hours, but we woke them long enough for them to open up some books they'd been dying to read. I got a new game for my Playstation and then we all hit the sack.

Unfortunately, neither Brandi nor I had the energy nor drive for another show-me- yours encounter.


Christmas turned out to be a flurry of activity, at least as far as the phone lines were concerned. The parents made various calls to friends and family to wish them Merry Christmas. And I got surprise calls from both Megan and Cassidy, who reminded me that they loved me along with their Christmas greetings. I was pleasantly surprised. It never would have occurred to me to try calling them.

Just after lunch, Keira McNeil walked over with a thank you note written on the back of a 5"x7" photograph of her newly remodeled home, and I got to chat with her for a minute where she told me how things were going well with Stuart and that she was happy I seemed to be enjoying good relationships with girls my own age.

And then to my everlasting joy and surprise, Dawn Evans also called me, and we spent an hour catching up with each other. She'd broken up with Mark and wasn't currently seeing anyone. She professed how much she missed me and couldn't wait for the summer. I missed my friend as well and in my taciturn teenaged male way, I think I managed to communicate that.

Brandi also got calls from friends, and in the evening, she got one particular call for which she got really hushed and ran into her bedroom. And when Brooke and I noticed how secretive our older sister had gotten, we got evil grins on our faces and I gestured for her to come into my room.

Brooke and I both settled onto my bed, and with a finger over my lips to remind her to stay quiet, I reached over and tapped the speaker button on my phone. Quietly, we then eavesdropped on Brandi's conversation.

It started with Brandi giggling. "You're so bad!"

"Can't help it, Brandi," came back the male voice. "You're so hot I can't help myself."

"Right now, Brian? You're jerking off right now?"

"Yeah ... I can't get your last kiss out of my mind. You smelled so good; and all I could do was imagine running my hands all over your naked body."

"Mmm..." Brandi moaned.

"Can I give you a massage when you get back? I won't try to fuck you, I promise. I just want to massage you, touch your muscles. I'll rub this hot oil all over your body, stroking your soft skin and rubbing you ... everywhere."

"Everywhere?" Brandi's voice picked up in pitch.

"Everywhere. I'll rub your back. I'll massage your arms. I'll rub your legs, and even firmly press my palms into your firm buttcheeks ... Ohhh, Brandi, I'm so hard for you. And when you're good and relaxed, I'll move my hands between your legs. I've very good with my hands, Brandi."

"Really?" Brandi's voice caught as she gasped.

"Very good..." he said in a low voice.

I started to get alarmed with where the conversation was going, and I flicked my gaze to 14-year-old Brooke. This was probably a little too risqué for the younger girl and I moved my hand over to turn off the speakerphone.

But Brooke darted her hand to my wrist and stopped me, shaking her head while looking at me with wide eyes. I wanted to hear the rest myself, so I quietly nodded and pulled my hand back.

"What then, Brian?"

"After I make you cum, I'll slowly turn you over onto your back. And then I'll spend an hour massaging your front. I won't even try to get you off, just stroking, rubbing, massaging everywhere. I'll oil up your wonderful breasts, just rubbing, nothing sexual. I'll massage your legs and your belly and by the time I'm done with you, you'll be a limp, unconscious, puddle of flesh, just floating on a cloud of happiness."

"Ohhh ... Brian ... You're going to make me cum just talking to you."

"Are you playing with yourself, Brandi?"

"Yes! Ohhh..." my sister moaned.

"You're so sexy. I didn't tell you that enough when we went out. I couldn't believe I was dating a stone fox with such a hot body! You're unbelievably sexy, Brandi."

"Mmm ... tell me more..."

"I love your ass. You have the most dynamite ass I've ever seen. I just want to stick my face in between your cheeks and lick you and suck you and squeeze you until you're cumming all over my face."

"Ohhh ... Brian!"

"Cum for me, baby. I wish I could be there to see it. I wish we could have done this in person. But I'll see you happy any way I can. Cum for me! Let me hear it! I'm gonna cum too! I'm gonna spurt, Brandi!"

"Oh! Oh! OHHH!!!" Brandi gasped into the phone, clearly in the throes of her orgasm. The sound was soon met by male grunting, and Brandi seemed to moan even louder as she heard Brian's noises.

I glanced over to Brooke and found that my little sister had a hand in her own shorts and she was wincing as if in pain, biting down on her lip to prevent herself from moaning out and giving us away. But even when she realized I was staring at her, she didn't stop frigging herself and in fact, her pace seemed to speed up.

I recognized the look on Brooke's face. She looked just like Megan did right before she came. And with quick thinking, I reached over and stabbed the speaker button, cutting off the sound of Brandi's and Brian's orgasms.

I was just in time, Brooke couldn't hold back her own moan as she stiffened up and came, her eyes watering as she stared back at me and then she gasped for oxygen as the first contraction left her body. Unable to hold herself upright anymore, my little sister tilted over and collapsed against my side, burying her face against my chest while I instinctively wrapped my arm around her back to hold her up. And in my arms, Brooke shuddered and whimpered as her orgasm swept through her body.

When she was done, Brooke's eyes went wide open and she jerked herself away from me in embarrassment. But I just smiled and held my finger to my lips to remind her to keep quiet. Any louder noises and Brandi might realize we were just in the next bedroom.

After another minute, Brooke realized I wasn't upset with her for masturbating. So she cuddled herself against me while she came down from her sexual high. And still curious about Brandi's phone sex, I reached over and hit the speakerphone again.

"I'm still so horny, Brian," Brandi moaned. "I need your cock ... right now. Gawd what I wouldn't give to get fucked right now!"

"I wish I was there, baby. I'll see you as soon as you fly back. Maybe I'll ride with Dayna and meet you at the airport."

"You do that Brian, and you're gonna get very lucky that night."

"Ohhh, I can't wait, Brandi."

"Me, neither. I'm so glad you called. Merry Christmas, Brian."

"Merry Christmas."


Tuesday was Eden and Emma's 11th birthday. Even though it was December 26th, Mom called them her Christmas presents since she actually started labor late on Christmas night. I still had a vague memory of being five-and-a-half and wondering what the heck was going on when Mom stood up in the middle of Christmas dinner and started yelling that her water broke.

Unfortunately for the twins, this meant they only got one set of presents every year. Fortunately for the twins, being the babies of the family meant that mom and dad more than compensated with additional gifts and toys sprinkled throughout the year.

Still, given a choice, I'm sure the girls would have preferred a birthday farther removed from such a major holiday. For one, all the prime birthday spots like roller skating rinks, miniature golf centers, and bowling alleys were always packed with kids on Winter Break. But more importantly, a lot of families took vacation at this time of year and only about half their friends were ever available to attend their birthday parties.

I could only imagine how crazy things would have gotten if all their friends actually came to a party. Eden and Emma were quite popular and they still had dozens of other 10 and 11-year-olds coming to this year's birthday party the day after Christmas.

Some brought brand new toys with them. Some were showing off new clothing they'd just received. And all of them had bundles of extra energy from the holiday season.

And guess who had to play chaperone for a few dozen 10/11-year-olds who believed they were too old to be supervised?

To be fair, it WAS all three older siblings who had responsibility. We were at a bowling alley and Brandi was over by lane 5 trying to keep the kids from bowling four balls at the same time. Brooke was at lane 8 trying to impose her will over kids who were only three years younger than her and unwilling to accept her authority. And my mom was fussing over a young girl who'd dropped a 20-pound ball on her toe and was bawling her eyes out.

Me? I lucked out and the kids I was watching over were pretty mellow. So I left them to their own devices for a bit while I marched over to Brooke's crew and calmed them down, the young girls more willing to accept the authority of a 5'10"+ male.

Then I dropped by Brandi's group and managed to convince her charges to quit screwing around because MY group was doing a better job bowling and the highest scores would get to be first in line at the pizza lunch. The youngsters immediately focused on bowling one at a time.

A minute later, Brandi was standing with me behind the lanes while we looked over her kids. "Thanks, Ben. You know, I remember when you were just another little twerp like them."

I just shrugged.

"You've grown up into a fine young man, Ben. Megan and Cassidy are lucky girls." Brandi patted my shoulder.

I just smiled and then belatedly realized that Brandi still had her hand on my shoulder. She was a few inches shorter than me, and when I turned to look, I found that she was staring straight at my bicep as she experimentally squeezed it, feeling the dense musculature there. I wasn't the kind of guy who hit the gym or anything, but I'd always had a good metabolism and I got a lot of exercise, both from common activities like basketball and from my recent sexual escapades.

Not quite sure how to react, I said nothing nor moved to stop her. Brandi was still holding my arm with one hand when she brought up her other hand to gently touch my chest, finding it as firm as my arm had been. Ever so gently, she kept trying to squeeze me while her breathing got rougher. And then I saw that subconscious reflex as her tongue came out and snaked across her upper lip.

"Hey Brandi!" one of the kids called. And like a switch had been thrown, Brandi abruptly jerked her hands away from me and blinked several times as if not understanding what she'd been doing.

Without another word, she turned and stepped back down to the lane.


That night, I'd absorbed myself in one of my new video games and completely lost track of time. It was after midnight when I turned the Playstation off and went upstairs, going through my usual routine of brushing my teeth and taking a shower. The coast was clear and the lights were out, so I assumed that everyone had gone to sleep.

I dried off in the bathroom and then wrapped my damp towel around my waist for the return trip to my bedroom. And then out of habit, I walked in the door and closed it behind me, dropping my towel to the floor while I headed to my dresser that had all my underwear and my pajama pants.

That's when I saw that my room wasn't empty. Brandi was reclining on my bed, wearing just a thin robe over her panties, and with no bra. Her eyes were locked onto my naked midsection while she dug her fingers inside her panties and rubbed herself.

"Jeez! Brandi!" I sputtered in surprise and immediately ducked to grab my towel and pull it to cover me.

"No, don't!" she quickly pleaded, motioning for me not to cover up. And then as I stared in disbelief at her, Brandi parted her robe to the sides to reveal her naked breasts.

Per usual, I'd jerked myself off in the shower to a medley of fantasies that ranged from Dawn to Dayna and to my current girlfriends. I'd managed to avoid the Brandi fantasies this time, but now that I was seeing my sister half-naked on my bed, I was certain she'd be in my fantasy tomorrow.

"Come here, Ben."

Half-nervous and half-excited, my desire to see her tits from closer up outweighed my embarrassment at my own nakedness, so I walked up next to the bed while Brandi stared hungrily at my cock, which had begun to rise while I ogled my older sister's tits.

"I just had to see it again," Brandi breathed. "Dayna was right. You have a beautiful dick."

"Uh, thanks," I stammered. "Uh, you've got really nice tits," I replied lamely.

Still frigging her clit, Brandi was breathing hard as she let her eyes rove around my naked body in little visual excursions that always returned back to my erect prick. She sighed and frowned, "I am such an idiot. I should have fucked Brian before I left. Then I wouldn't have this anticipation all Winter Break and I wouldn't be so fucking horny!"

I didn't know how to respond to that so I didn't say anything. I was too mesmerized looking at the lustful expression on Brandi's face anyways. She had the same half-torn/half-aroused look I'd first seen in that clearing at camp, where the Evans sisters effectively brought Brandi and me to a foursome on our last day. She and I had crossed a line that day. I wasn't sure if it was about to happen again.

"You're so lucky, Ben," Brandi moaned forlornly. "Megan's coming home on Saturday and Cassidy next Tuesday. I've got to wait three more weeks to see Brian."

"Uh, sorry..." I tried to say in sympathy.

"Can I touch it?" For the first time, Brandi's gaze swiveled up to my eyes. She had a look of such desperate pleading that all I could do was nod affirmatively.

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