"Taking" My Sister's Virginity

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Older brother seduces and takes cute nerd sister's virginity.
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Summary: Older brother seduces and takes cute nerd sister's virginity.

Note: This is a Winter 2014 contest submission.

Note 2: Thanks to MAB7991, Robert and goamz86 for editing this story.

Note 3: All participants are at least eighteen years old.

"Taking" My Sister's Virginity

I wasn't necessarily eavesdropping, as they were drunk and not really talking quietly...I could hear them clearly from the vents that went from my room to hers.

That said, what I heard shocked me.

"I can't go through my whole senior year a virgin," Lisa, my sister, whined.

"It's only November," her best friend, Andrea, pointed out.

"It's almost December," Lisa countered, before singing playfully, "All I want for Christmas is to get laid."

"Does oral sex count?" Andrea questioned with a giggle. "Because if it does, you are a complete skank."

"I'm not sure giving head to seven guys counts," my sister countered, which shocked the shit out of me. My sister was the biggest nerd I had ever met: in both looks and personality. She wore pigtails every day, dressed like she was living in the sixties, and wore glasses that only added to her nerd persona. She also was always reading a book, was a member of the debate club, played the trumpet, and volunteered for the SPCA (which isn't nerdy, it just explains how sweet she is). So to hear that she had blown seven guys was almost impossible to believe.

I reached for my phone and pressed record just in time to hear Andrea's response, "True, but four were on the same day."

"Okay, I agree that was kind of slutty," my sister giggled.

"You swallowed four loads in an hour," Andrea pointed out, my own cock throbbing at the thought.

"At least I didn't take a facial like you did," Lisa countered.

"I don't like the taste," Andrea defended.

"It's an acquired taste," Lisa quipped.

"Yes, you're really a cum connoisseur," Andrea giggled.

"I hope to be," Lisa said back, before adding, "Although nothing tastes better than pussy."

I gasped. My sister was a virgin, but not only did she love sucking cock, she also ate pussy?

"You hungry again?" Andrea purred, her tone dripping with naughtiness.

"It's been a couple hours," Lisa responded, "plus it's after midnight, which means I haven't eaten that sweet cunt of yours today."

Hearing my sister use the word 'cunt' was also shocking, as I had never heard her swear...ever.

"You really are an insatiable little pussy pleaser," Andrea teased.

"I've never heard you complain," Lisa shot back, her tone also super sexy...a tone I never thought I would hear coming out of her mouth.

"Beg, bitch," Andrea ordered, her tone playful and firm.

"Oh please, let me lick that trimmed box of yours," Lisa begged, sounding both sexy and absurd.

"You do need to work on your dirty talk," Andrea teased.

"Just spread those legs and give me that pussy," Lisa demanded.

"Aggressive, I like that," Andrea said, before the talking stopped.

I listened intently, wanting to hear moans or dirty talk...something to tell me they were in an act of lesbianism.

After a couple of minutes of silence, Andrea finally began moaning, "That's it, suck on my clit."

I pulled my erect cock out and began stroking myself as I envisioned my sister eating her best friend's pussy.

I continued pumping my cock as I listened to the moans of Andrea at the hands and tongue of my cute nerdy sister.

"Oh shit, so close," Andrea moaned, and I imagined that she grabbed Lisa's head and held her buried deep in her cunt.

I tried to time my own orgasm to Andrea's, slowing down to keep me close but not come until I heard the inevitable word, "Yessss!"

A few seconds after Andrea came, I followed suit, shooting my cum straight up in the air.

I laid there, covered in my own cum, as I continued to eavesdrop hoping for more juicy secrets.

"Fuck, I love your cum," Lisa finally said.

"And I love your tongue," Andrea replied, her tone implying she hadn't completely recovered from her orgasm.

"I know you do," Lisa replied, as I imagined them kissing.

I was beginning to fade when I heard, " Do you think your brother has a big dick?"

"Gross," Lisa said, as I sat back up, suddenly very much awake.

"He's fucking hot," Andrea said, which didn't really surprise me as I had noticed her checking me out in the past.

I am not Brad Pitt good looking, but I have been favourably compared to Colin Farrell...which sure isn't a bad thing. Lisa and I are in many ways polar opposites. Although I am quite intelligent, I seldom used my intelligence to get good grades, seeing school as a monotonous waste of time...particularly since I planned to be a mechanic. Who cared about metaphors, geometry, limits, or Shakespeare? So I goofed off, skipped school a lot and got solid 60s, even though my teachers always told my parents I was capable of so much more (which, of course, I was...teachers are usual very good at assessing student's ability).

Anyway, while Lisa looked sweet and innocent, I looked dark, handsome and brooding...a look I mastered. Aloof was my flirt style and it had worked most of the time...girls always say they want a nice guy, but that is bullshit...they all fantasize about the bad boy and I...am a bad boy.

"So I've been told," Lisa said, her tone implying she had heard these rumours about me before.

"You don't think he is hot?" Andrea asked, her tone incredulous.

"He's my brother," Lisa pointed out, not answering the question.

"If he was my brother, I'd be committing incest," Andrea said.

"You're twisted," Lisa replied.

"Says the girl who has eaten my pussy twice tonight," Andrea countered.

"Eating pussy and incest are two very opposite ends of the spectrum," Lisa replied back.

Incest had never popped into my head, but the seed planted, the thought of being Lisa's first suddenly popped into my head...although I had no idea how to make such a conquest a reality.

"Is it?" Andrea countered, "Cock is cock."

"So I should eat out my Mom then since cunt is cunt," Lisa countered, sarcastically.

"Your mom is also hot," Andrea replied.

"You're ridiculous," Lisa said.

"So back to my original question. Do you think your brother has a big dick?" Andrea asked again.

"Oh, I imagine it's a massive snake," Lisa replied, her words dripping with sarcasm.

"Those trunks he wears in the pool don't leave a lot to the imagination!" Andrea said. "Plus those tats are hot, as are his pecs."

"Why don't you go to this room and find out?" Lisa challenged, my eyes going wide.

"What, you want me to do some undercover spy slut recon for you?" Andrea teased.

"Yes, Andrea, I want my first to be my big brother," Lisa sarcastically retorted.

"Oh, you wouldn't reject him if his cock was here right now," Andrea challenged.

"Yes, I would drop to my knees and devour his cock before spreading my legs wide open and letting him fuck me senseless," Lisa replied, playing along.

"Fuck that is hot," Andrea moaned.

"Incest turns you on?" Lisa questioned.

"It doesn't you?" Andrea questioned.

"Of course not," Lisa replied, although something in her tone implied the thought wasn't as appalling as she first implied it was.

A moment later, my cock hard again, Andrea said, "Holy shit, you're drenched...incest does turn you on."

"No, eating your cunt turns me on," Lisa protested.

"Sure, sure," Andrea said, "I guess I should probably return the favour, or you'll probably go to your brother and ride his cock."

"I would not," Lisa replied playfully, adding, "but I bet you would."

"In a heartbeat," Andrea responded.

"Slut," Lisa teased.

"Brother lover," Andrea shot back.

I kept listening, but the talking stopped and I assumed Andrea was eating out my sister. Eventually I fell asleep, my head spinning with all my newfound knowledge.


Of course, I saw my sister differently after that shocking night. Yet, I couldn't bring it up. I suddenly wanted my sister. I wanted to be her first. I also wanted Andrea, which would be a lot easier to accomplish.

A few days later, the two girls were out sunbathing by the pool during a weekend in November, one of the many perks of living in Southern California, when I decided to begin the seduction of my sister...by seducing her best friend first.

I had already complimented both of them a couple of times the past few days and started walking around the house without a shirt, hoping my well-built body would be tempting.

I walked outside and greeted them, wearing only a tight speedo that left nothing to the imagination, "Good afternoon ladies."

Andrea, who was clearly distracted by my body and likely my well outlined package, stammered, "H-h-hi, Eddie."

"You should come for a dip instead of just getting skin cancer," I offered, as I went to the diving board and dove in.

I swam for a couple of minutes, before I heard a splash. I stopped my laps and smiled, "Glad you could join me."

"Well, it's cooler in here than out there," Andrea smiled, trying to flirt.

"I agree," I said with my charming smile, before splashing her.

She splashed me back and we began horsing around.

Suddenly Lisa jumped in too and it was two against one.

I picked Andrea up and tossed her into deeper water, then dunked Lisa. We horsed around some more and had a great time where I made sure while horsing around to get a good grip on Andrea's ass, brush her medium sized tits and dunk her so very briefly so that her head was at my crotch. I also did some more subtle touches to Lisa.

Eventually, we were all hungry and thirsty and got out of the pool. I suggested, in my big brother way, that Lisa go and get us some ice tea.

Once she was gone, I said, turning on the full charm, "So Andrea, you really have blossomed into one very good looking woman."

"R-r-really?" she stammered, clearly surprised by my words.

I put my hand on her leg, "Really."

I let the silence linger, before adding, going on the full offensive, "You have an amazing body, a sexy smile and lips to die for."

Andrea's face flushed, "Y-y-you really think so?"

"I know so," I said, my hand moving up her leg slowly.

Her whole body trembled just as we heard the door open. I gave her leg a meaningful squeeze before moving my hand away and adding, keeping my trademark smile, "I hope to get to know you much better, beautiful."

Her cheeks were so red I thought she may pass out from all the blood rushing to her head.

Lisa, oblivious to the sexual tension created between Andrea and I, said, "Here you go," and handed each of us an iced tea.

We chatted about the upcoming Christmas holiday plans, applying for scholarships...all generic fluff as I continued to give Andrea knowing looks.

I eventually excused myself and waited until a couple hours later when Lisa was in the washroom to ask Andrea, "Do you want to go up to Lakewood Point at midnight?"

"R-r-really?" She asked, so adorably in lust with me.

"Yes," I nodded. "Where should I pick you up?"

"At the 7-11 by my house," she eagerly replied

"See you then," I smiled, then left, not wanting to actually have a long conversation.


A few minutes after midnight, always leave them waiting and doubting, I rolled into the 7-11. She was waiting outside; shivering slightly as it does get cooler in the evenings this time of year, wearing a blue sundress which would make getting to that sweet cunt easier.

I pointed to the passenger side door and she scurried to my car. Once inside I complemented, "You look hot, Andrea." I had learned early on shy and nerdy girls don't want to be called cute, they want the most simplistic descriptor in the world: 'hot'

"Thank you," she blushed, clearly not used to getting compliments from boys. "You look hot yourself," she complimented back.

I joked, "I spent hours getting ready."

She laughed, "I've seen you in the morning and at bedtime, you always look hot."

"It's how God made me," I shrugged.

"Well, I am one to revel in the Lords work," she joked, surprisingly witty.

I put my hand on her leg. "Ever been up to Lakewood Point?"

"Not at night," she admitted, her leg quivering slightly at my touch.

"No boy has offered to take you up there yet?" I asked incredulously,

"Nope," she shook her head.

"Well, time to change that answer then," I smiled, giving her leg a squeeze.

A few minutes later, we were at the teen make out point. As I pulled to a stop, I said, "Let's go for a walk."

"Sure," she nodded, willing, I think, to agree to almost anything I suggested.

As we began walking the dark path, I took her hand. I explained, "I've never really been a make out in the car kind of guy."

"Oh, okay," she said, clearly curious where we were going.

"On the other hand," I said, "I know a great place for some privacy and a beautiful spot to check out the lights from town."

"Okay," she again agreed, assumedly knowing what I was expecting from her once we reached my secret make out spot.

We walked in silence through the trail, up a slight climb between two trees that no one else seemed to know about (I found it while walking with my family when I was just a kid) and to a remote spot that overlooked the town and lake.

"Wow!" She said impressed, obviously having been oblivious to its existence like everybody else.

"I know," I nodded, "it's a great place to relax."

"It's amazing," she said, looking at the gorgeous view.

"Yes, you are," I smoothly responded, leaning in and kissing her.

She responded with youthful exuberance as our tongues explored every crevice of each other's mouth.

Breaking the kiss, I decided to play with her mind, "I knew you would be a good kisser."

"You did?" She asked, surprised as she looked into my eyes.

"Well, I envisioned you were when I overheard you and Lisa the other night," I revealed.

Her face paled. "Y-y-you heard us? What did you hear?"

"It was pretty hot," I said, trying to relax her. "Shocking and hot."

"I can't believe you heard us," she said, clearly embarrassed.

I shrugged, "Hey, it's 2014, being a lesbian or bisexual is in."

"I just," she began, but I kissed her again. This time at first she was tentative, still shocked that I knew.

I kept kissing her until she responded with eagerness before I broke the kiss again.

"So, I also heard you don't swallow," I said, smiling.

Her face already flushed, went redder. "What else did you hear?"

"That my sister blew four guys in one day, she loves eating pussy, particularly yours and you're curious about the size of my cock," I listed.

"Oh my God," she gasped and giggled, like the school girl she was, "she is going to die if she finds out you know."

"Why?" I asked, "it's nice to know she isn't the nerdy prude she acts like."

"She has two personas," Andrea admitted. "Well, three truthfully. The family good girl one, the school academia one and then the sexy one she is just coming to grips with."

"Enough talk about my sister," I said, back into seduction mode, "let's focus on why we're here."

Her eyes went big as I stood up and said, "I think it's time for you to find out the answer to your question."

She was staring at the bulge in my tight jeans as I moved directly in front of her.

I said soothingly, "Go ahead, sexy, find out first-hand how big I am."

Her hands were trembling as she reached for my fly.

She fished out my thick seven inch cock and purred, "Mmmmmm, just as I imagined." She leaned forward and took it in her mouth.

I love watching a girl suck my cock. The way their adorable faces completely change when full of cock. I groaned, complimenting her knowing that was a way to get girls to do even more, "That's it, Andrea, your mouth feels so good."

She continued taking more of my cock in her mouth, my thick cock stretching her lips.

Planning to come twice, once in her mouth and a second time on her face after I fucked her, I hadn't touch myself all day. That meant, the first load wouldn't take long. After only a couple of minutes of this cute teen taking about four inches in her mouth with each sloppy bob, I was ready to shoot my load.

Being the aggressor, I grabbed her head and began fucking her face. I didn't force all seven inches down her throat, like I often did to cock hungry sluts, but I pumped fast for a few strokes before depositing my cum down her throat. She had no choice but to swallow as my cock kept pumping in and out of her mouth.

Once spent, I pulled out and said, in my bad boy tone, "Now you swallow."

She looked up at me with a mixture of shock and lust, before replying, clearly horny and lusting for me, "I'll swallow your load any time you want." Like many cute innocent girls, she wanted to be treated like a slut.

"Good to know," I nodded, as I moved to her.

Her body trembled at my touch, as I flipped up her sundress. On my knees between her legs, I pulled her panties down. Then remarked, "I see you trim."

"Your sister did that for me," she admitted.

"Is my sister trimmed?" I asked, trying to get more intel.

"Completely shaved now," she answered, "we did that before we hit the pool."

"Fuck, my sister is just full of surprises," I said.

"She is an enigma," Andrea agreed.

"As are you," I smiled, leaning forward and flicking her clit with my tongue, before adding, "especially after your teasing talk about incest."

"I forgot about that," she laughed, before adding, "we had drunk a whole bottle of wine."

"It was pretty hot," I said, "and got me thinking."

Her eyes went big. "You want to fuck Lisa?"

I gave her my trademark smile, "Actually I want to fuck you right now. Are you a virgin too?" I asked, leaning forward as she stood there and I licked her pussy.

"No, but I've never had anything close to as big as you in me," she said, a lust in her eyes that told me everything.

After a minute, I stood up, bent her over a tree and slid my cock in her wet cunt.

"Oh yes," she moaned, as my cock filled her tight cunt.

I don't make love to girls, I fuck them, and after a few strokes to get her used to my cock, I began slamming my cock into her.

"Oh shiiiit," she whimpered, as I drilled her cunt.

I loved the sound of my body slamming into hers; I love the sound of women in the heat of the moment; and I love the thrill of outdoor sex.

I fucked her deep and hard for a few minutes, in for the long haul after coming down her throat. I could tell she was close to coming, as her breathing increased.

"Come for me, my little high school slut," I ordered, knowing exactly when to start the name calling, knowing that all good girls secretly want to be used as sluts.

"Oh yes, fuck my cunt," she responded, talking nasty as soon as I opened the door for her.

"Now my new cum slut," I continued, "come like the little high school slut you are."

"Yes," she moaned, and after a couple more deep thrusts she screamed as she came, "I'm your slut!!!!"

I continued fucking her hard, and she held onto the oak tree for dear life, as her orgasm riddled her body.

"Oh, God," she barely got out, as I kept pounding her, working to find out if she could have multiple orgasms. Some can, some can't, but if they could it usually was from continual hard fucking.

I shouted, "Bounce on my cock," then ordered, "let's see if you can come again and again."

She pushed back and began riding my cock, placing both her hands flat on the tree. Watching her bounce back was hot, I love seeing a woman just give in to the unbridled lust that overtakes everything else.

Her breathing was erratic as she took all my cock in her tight pussy with each backwards bounce.

I was getting close to eruption myself when she screamed, "Fuuuuuck, I'm cominnnng again."