Taking My Sister’s Virginity by jasmine walker

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.”

Her legs buckled and she fell sideways to the ground. As she quivered on the ground, my balls about to erupt for a second time, I straddled her and shoved my cock in her mouth. The position was awkward, but I again fucked her face.

In only a few strokes, I deposited a second load down her throat. Spent, I pulled out and rolled beside her.

She weakly said, with a sly smile, “Apparently, I do swallow.”

“Apparently,” I laughed.

On the drive home, I asked, “Want to be my partner in crime?”

“You have me curious,” she replied.

“So do you want to help me with something rather risqué?” I continued.

“Still curious,” she said.

“Help me fuck my sister,” I revealed.

“Mmmmmmm,” she smiled, “I knew you wanted to fuck her.”

“Think she will?” I asked.

“Maybe,” she shrugged. “She desperately wants to break her cherry.”

“So you’ll help?” I asked.

“Can I watch?” she asked.

“You’re a very dirty girl,” I teased as I pulled onto her street.

“Says the boy that wants to take his sister’s virginity,” she quipped back, completely out of her shell after two intense orgasms.

“Touché,” I laughed.

As I parked, I asked, “So you in?”

“Hell, yeah,” she smiled. “Do you have a plan?”

“Not really?” I shrugged. “The idea only began after hearing you bring it up.”

“Hmmmm, I started your incest fantasies,” she smiled.

“And also my interest in you,” I added.

“Does that mean this will be more than a one-time thing?” she asked.

“Yes, but I don’t think Lisa can know,” I said.

“Agreed,” she nodded. “Let me think on it.”

“Great,” I nodded, giving her a quick kiss.

Once she was gone, I drove home with many ideas spinning in my head on how to seduce my sister.

…..

Over the next couple weeks, Andrea and I discussed many plans and fucked quite a few times, including in my bedroom during a sleepover after Lisa fell asleep.

It was early December when we formulated a plan…a brilliant one. Andrea set us up online, telling Lisa that I was her cousin and coming to visit during the Christmas holidays. Andrea stole a picture from some Facebook friend of a friend of a friend and Lisa and I started conversing through yahoo chat.

The first chat was a very generic get to know you chat, but each chat got more flirtatious and more personal. She never told me she was a virgin, but she did admit she liked oral sex. I told her we would be a great match as I really liked receiving oral sex. I knew she liked guys who challenged her, who were a bit of a bad boy; I promised I would indeed challenge her and that I was the epitome of a bad boy. I told her I expected my girl to dress sexy, be in nylons, and always wear her hair down (she always wore hers up). She told me she liked a man who knew what he wanted.

After a few chats where we got to know each other, me able to manipulate all I knew about my sister to get her to think she had met Mr. Perfect, Andrea suggested to Lisa that she invite fake me, Adam was my online name, to the Christmas party at her work.

Lisa1996: What day are you arriving again?

Adamistheman: Thursday afternoon.

Lisa1996: Would you be willing to be my date for a Christmas banquet at work on Thursday?

Adamistheman: I’d love to.

Lisa1996: it’s formal, dinner and then a Broadway show.

Adamistheman: is it Cats? I can’t do Cats.

Lisa1996: lol…no it’s The Phantom of the Opera

Adamistheman: in that case…definitely

Lisa1996: great

Adamistheman: is this a real date?

Lisa1996: if u want it to be

Adamistheman: and if u play your cards right I just might let u take advantage of me

We had been flirting ridiculously the past few chats, Lisa all but saying she wanted to give it up to me and I clearly implying I planned to give it to her.

Lisa1996: ohhh, I plan to take advantage of u whether I play my cards right or not

Adamistheman: you’re all talk

Lisa1996: wait a sec

I waited. Ironically, I was just below her as we both chatted with each other from our bedrooms.

Suddenly a photo popped up. I gasped, it was a picture of her shaved pussy. Even I was surprised by such a brazen act…this was very unlike my smart sister (this picture could be on the web in seconds if it was sent to the wrong person…thankfully, for her, I would never do such a thing).

Lisa1996: Like?

Playing cool, always pushing her into doing more I responded.

Adamistheman: that is an amazing pussy, but how do I know it’s yours?

Lisa1996: tell me what u want me to insert in it right now.

I gasped again, surprised. She really was going for broke. I had never been more turned on by any woman as I currently was by my sister. Deciding to call her bluff, I came up with an elaborate order.

Adamistheman: do you have any pantyhose?

Lisa1996: a couple of pairs

Adamistheman: put a pair on, actually I want you always in pantyhose when chatting with me.

Lisa1996: okay, give me a minute

Adamistheman: k

I waited. My fetish, likely because of mom, was nylon legs and feet. I don’t know why, but seeing a girl or woman in nylons always made my cock instantly hard. Lisa wore nylons a few times for her more formal events, but not too often. Mom, on the other hand, being a teacher, wore them almost every day and tended to stay in them all evening. I always wondered if Mom knew the impact her legs had on me.

Lisa1996: back

Adamistheman: take a picture of your legs and feet in nylons

Lisa1996: k

In our brief few chats it had become obvious that Lisa was submissive. I suspected as much as I reflected on her personality and her insatiable need to please other people…Andrea included. I also noticed she rarely questioned what I said and sensed that if I played my cards right I could end up fucking her.

A moment later the photo popped up. It was definitely her as I could see the same purple painted toenails I’d noticed today at breakfast, not to mention her brown carpet.

Lisa1996: well???

Adamistheman: Delicious…I expect you to be wearing pantyhose for our date.

Lisa1996: is that an order?

Again she was just a natural submissive and yet also incredibly playful. I decided to see how far I could push her.

Adamistheman: it is! Plus, I want that shaved pussy of yours to have easy access for me.

Lisa1996: <blush>

Adamistheman: do you own any thigh highs?

Lisa1996: what are they?

Adamistheman: like pantyhose, but they only go up to your thigh.

Lisa1996: oh, then no.

Adamistheman: get some for Thursday, when I say easy access to that beautiful cunt of yours, I mean completely available: so thigh high and no panties.

I wasn’t sure if I had gone too far, as she didn’t respond right away. Usually, her responses were very quick, as if she couldn’t wait to see what I was going to say next. Finally, she responded.

Lisa1996: I will find some thigh highs and keep my cunt ready for that cock of yours.

Although I had suspected she would obey, seeing her type in ‘cunt’ and ‘cock’ had my cock ready to erupt.

I texted Andrea.
Get your ass here ASAP.

Adamistheman: I hope you’re not just saying that.

Lisa1996: oh, Adam, I am a SURE THING!!!

Adamistheman: want to see a picture of my sure thing?

Lisa1996: God, yes.

I had snapped a picture of my fully erect cock after Andrea had sucked it for a few minutes back at my secret location a few days ago, so as not to have any background evidence from my room.

Andrea texted back:
Have your window open.

I quickly texted back:
It always is!!!

I sent the picture.

Lisa1996: is that really yours???

Adamistheman: the one God gave me

Lisa1996: how do I know that’s really yours?

Adamistheman: u will when I shove it in your mouth!

Lisa1996: promises, promises.

Adamistheman: I just hope u can take all seven inches in that pretty mouth of yours

Lisa1996: oh trust me, your cousin calls me a cum connoisseur

Adamistheman: she also tells me you’re a virgin.

Lisa1996: that bitch.

Adamistheman: no, trust me, that makes you even hotter.

Lisa1996: really?

Adamistheman: yes, I will train you to be a perfect little fuck toy

I continued to push her, sensing she was willing to do anything I demanded.

Lisa1996: <blush>

Adamistheman: do you want to be my fuck toy?

Lisa1996: God, yes.

Adamistheman: send me a picture with something in that cunt of yours, fucking yourself while we chat

Lisa1996: okay, give me a sec

Adamistheman: no, whatever is in arm’s reach

Lisa1996: all I have is a brush

Adamistheman: perfect

Lisa1996: really?

Adamistheman: do it now! Fuck yourself with that brush, imagining it’s my cock

Lisa1996: k

I could hear soft moans through the vent. She was obeying my command.

Adamistheman: are u fucking yourself?

Lisa1996: yessss

Adamistheman: take a picture with that makeshift cock in that cunt of yours

Lisa1996: kkkkk

A moment later, again obeying me, she took a picture of the brush in her cunt, her pantyhose tugged down. It was fucking hot.

Adamistheman: fuck, u r one hot little wannabe slut

She was still fucking herself, her moans getting heavier through the vents, just as Andrea snuck in my window.

I snapped my fingers and pointed to my crotch.

Like the good slut she was, she didn’t question, but obeyed, crawling onto the bed, fishing out my stiff cock and taking it in her mouth.

Lisa1996: I’m going to come soon

Adamistheman: STOP!

Lisa1996: what?!?!?!

Adamistheman: I want that pussy revved up and ready for me when I see you.

Lisa1996: I can’t come now?

Adamistheman: no…not until I see you. They say patience is a virtue.

Lisa1996: I’m not feeling too virtuous at the moment

Adamistheman: trust me, it will be worth it

Lisa1996: k <sad face>

Adamistheman: and no coming from my cousin’s tongue

Lisa1996: u know about that?????

Adamistheman: she told me everything

Lisa1996: oh God

Adamistheman: but u can still eat her out

Lisa1996: I don’t like u very much at the moment

I groaned as my balls were already ready to burst after just over a minute of deep throat cocksucking.

Adamistheman: five days and I will rock your world

Lisa1996: five days and I may shrivel up and die

Adamistheman: what doesn’t kill u makes u stronger

Lisa1996: what if it kills me?

Adamistheman: then u die a virgin

Lisa1996: that is a horrifying thought

Adamistheman: I’ll fix that nightmare on Thursday!

I shot my load deep down Andrea’s throat as the idea that I would soon deflower my sister filled my head.

Lisa1996: u better, u have me getting the female version of blue balls

Adamistheman: now that is funny

Lisa1996: not laughing

Adamistheman: I’ll have u screaming in pleasure soon

Lisa1996: u better!

Adamistheman: I got to go…now be a good girl, call my cousin over and eat her out in thanks for all she has done for u

Lisa1996: or kill her for telling u all my secrets

Adamistheman: it was the secrets that first drew me in

Lisa1996: okay, I’ll kill her and then bring her back to life

Adamistheman: night, my pretty little virgin

Lisa1996: good night, my virgin slayer

Adamistheman: virgin slayer, I like that

I signed off and said to Andrea, who was still slowly bobbing on my cock, “Everything is set.”

“I can’t believe you’re going to fuck your sister,” she said.

“I can’t believe it either,” I smiled, “but the wheels have been set in motion.”

Andrea’s phone rang.

She quickly grabbed it, the vent above potentially being able to pick up a sound, “Hello.”

Andrea winked at me. “I can be over ASAP, I’m just finishing up something.”

After hanging up, “Your sister seems frustrated.”

I handed her my computer and she read today’s conversation. “Oh! I am probably in for a long night.”

“I imagine you are,” I smiled, a devious idea suddenly popping into my head. I got out of my jeans and ordered, “Bend over.”

“Right now?” She asked.

“I’m going to fill that cunt of yours with cum and then you are going to have her eat out your just fucked box,” I revealed.

“You are soooo bad,” she smiled, flipping up her skirt.

I tugged her panties down and slid inside her cunt. I wished I would have thought of this before depositing a load in her mouth, as I was in for a long fuck.

After a few minutes, the idea of this being my sister soon, I shot a load in Andrea who was actually covering her mouth so as not to scream.

I generously pulled her panties back up for her and said, “Now go and have my sister suck my cum out of that wet cunt of yours.”

“I love your twisted mind,” she smiled, turning around and kissing me.

I slapped her ass and winked, “you’re not so bad yourself.”

She climbed back out the window, and a minute later I heard her talking with my sister.

Andrea said, “This better be a crisis because I was in the middle of getting laid.”

“By who?” Lisa asked.

“A college stud I met online,” she lied.

“Well, you could have finished first,” Lisa said.

“He did,” Andrea countered, before ordering, “and now you can finish me off.”

“Did he come in you?” Lisa asked.

“A full load,” Andrea said, before repeating the order, “now come and get me off, I’m fucking ready to burst.”

“Fine,” Lisa agreed, her tone implying she was still ready to burst too.

I listened as Andrea, learning from me that Lisa was submissive, was a bit more aggressive. “That’s it, lick Eddie’s cum from my cunt.”

Lisa questioned, “Eddie’s?”

“Yes, the college boy is named Eddie,” Andrea said, “now get back to licking.”

I wondered if she even remotely considered that it was me, but she didn’t say anything as I heard no more talking from her for a bit.

That said, Andrea, knowing she had an audience, did a lot of talking. “Fuck my cunt with that tongue,” and “Does the mixture of cum and pussy juice taste good?” and “Fuck, nobody eats cunt like you do.”

My earlier hard fucking, where she didn’t come, had her already revved up and in only a few minutes she moaned loudly, “I’m comiiiiiing.”

After a couple of minutes, Lisa said, “That was an interesting taste.”

“Pussy and cock cum all in one,” Andrea quipped.

“So who is this Eddie?” Lisa asked.

“Just a guy with a big dick,” Andrea answered.

“How big?” Lisa questioned.

“Seven long, thick inches,” Andrea answered, knowing I was listening. “Maybe I should hook you two up.”

“Are you two dating?”

“Not really, but I’m available for a booty call pretty much any time,” Andrea said, which definitely had been true. “If you hadn’t called I would have kept going until I came.”

“Sorry for calling, but read this,” Lisa said, “I may have gone too far.”

“You sent him those pics?” Andrea gasped, even though she already knew.

I couldn’t hear her answer, but Andrea continued to speak loud and clear, “Don’t worry, I’ll make sure those photos don’t go any further.”

“I can’t believe you told your cousin I was a virgin,” Lisa said.

“He’s kind of a stud and I had to sell you to him by bringing up the big ‘V’, that is every guy’s dream,” Andrea explained.

“And that we lez out?” Lisa continued.

“That just slipped out,” Andrea defended. “And maybe, we’ll have to set you two up with Eddie. I bet he would love a threesome.” I loved how Andrea was talking about me all the while, hinting to my sister, yet Lisa was oblivious.

“You’ve already set me up with your cousin,” Lisa pointed out, “plus, a threesome seems kinda slutty.”

“But you are a slut,” Andrea countered.

“Says the girl who is fucking some college guy,” Lisa quipped back.

“Says the girl who ate my cunt and some college guy’s cum deposited in it,” Andrea shot right back.

“Okay, we’re both sluts,” Lisa concluded.

“Especially after you bang my cousin” Andrea added.

“I hope he isn’t all talk,” Lisa said, clearly looking forward to losing her big ‘V’.

They continued chatting, but eventually it became all touchy feely and I dozed off.

…..

The next day, when I knew she wasn’t home, I sent a chat message:

Adamistheman: three days until I take your cherry!

She responded a couple hours later:

Lisa1996: what a crazy countdown

Lisa1996: by the way, I can’t believe I sent u those pictures. U probably think I’m some crazy slut.

I didn’t respond that day as life got crazy when I went out with some buddies and got a bit shit-faced. That said, I didn’t take home the pretty blonde who I easily could have, deciding strangely enough that I would stay focused just on Andrea and hopefully my sister.

Adamistheman: 2 days!!! And no I don’t think u r a slut…I do think u have been holding back as u always try to be the good daughter, good student and so forth. The reality is u can have sex and still be a good person.

Lisa1996: I was worried I scared u off

Adamistheman: no u constantly turn me on

Lisa1996: I bought thigh highs

Adamistheman: what colour

Lisa1996: a black pair and a dark beige pair

Adamistheman: I can’t wait to see u in those

Lisa1996: I can’t wait to have them wrapped around u

Adamistheman: now that is a hot visual

Lisa1996: agreed

Adamistheman: so I know u like giving head, but now we get to the big question…

Lisa1996: spit or swallow?

Adamistheman: no…swallow or facial; all girls swallow now

Lisa1996: ur cousin doesn’t…lol

I smiled thinking, ‘oh, she does now’.

Adamistheman: I’ll have to talk to her about that.

Lisa1996: u two have a strange relationship

Adamistheman: u don’t know the half of it

Lisa1996: so on that note…do u eat pussy

Adamistheman: of course, I like to munch on a cunt all night long

Lisa1996: I want to marry u

Adamistheman: and I want to devour u whole

Lisa1996: my body is your canvas

Adamistheman: in that case you’re my Moana Lisa.

Lisa1996: haha..funny…shoot it’s dinner; chat later tonight?

Adamistheman: I have a lot of school work tonight…but I’ll try to get online

Lisa1996: k

Adamistheman: later, sexy

I logged out and went up to have dinner with the girl I was just seducing online…my life was becoming way too surreal.

I noticed that she was in nylons and I instantly wondered if they were thigh highs. She was also wearing her hair down.

I complimented her. “Lisa, you look very nice with your hair down. It makes you look older, more mature.”

“Thanks,” she replied, “I’m trying a new look.”

“Well, it’s working,” I nodded, before shifting to ask Dad if he was watching the hockey game tonight, not wanting to spend too much time on her and to make her remotely suspicious, yet wanting to keep her confidence up.

Mom was also wearing nylons still and I was in ADD stocking heaven as the evening went on and we all watched New Girl as a family, four sexy feet, both pairs perfectly manicured, both in sheer nylons, completely distracting me.

As soon as the TV show was over, I texted Andrea to get her ass over here again. She had only been wearing nylons for me when we were alone as to not make Lisa suspicious.

Twenty minutes later, she was bobbing on my cock when her phone rang. I said, “Get it and put it on speaker phone.”

She reached into her purse and as she said hello, I greeted her cunt hello as well. “hellooooooo.”

“Are you okay?” Lisa asked.

Andrea answered, “Yes, I’m Okaaaay. I’m in the middle of something can I call you baaaaack.”

“Are you getting fucked right now?” Lisa bluntly questioned.

“Kind of,” Andrea answered, as I slammed into her.

“You’re kind of getting fucked?” Lisa questioned.

“Oh fuck,” Andrea moaned, louder than usual. “I gotta go, I’ll call you back soon.”

Andrea hung up and said, “You bastard, you’ll get us caught before the plan comes to fruition.”

“Who says fruition?” I quipped, as I continued fucking her.

“Just keep fucking me,” she demanded.

“As you wish,” I replied.

Close to orgasm, she begged, “Harder, fuck my cunt harder,” before coming a minute later and barely holding in a scream.

I deposited a load all over her face a couple of minutes later.

“What is it with coming on a girl’s face?” She asked, as she remained on her knees coated in my cum.

“It’s the act of submission,” I shrugged.

“It seems like such a waste,” she said, as she scooped some off her cheek and put it in her mouth.

“Fair enough. For a girl who didn’t swallow, you sure can’t get enough of it now.”

“You got me addicted,” she replied, taking my cock back in her mouth.

After a couple more minutes, she said, “I better call her back.”

“You’re a bad friend, hanging up on her just to have an orgasm,” I teased.

“Says the brother fucking his sister’s best friend, while also planning to commit incest by taking her virginity,” she countered, as she stood up.

“Touché,” I shrugged. “Touché.”

…..

When I got home the next evening, I had this message waiting for me.

Lisa1996: One day and counting

I responded even though I knew she was out with Andrea buying new shoes for the dress she was wearing tomorrow.

Adamistheman: u still sure u want to go through with this?

Twenty minutes later I sent one more message:

Adamistheman: I’m hitting the hay early tonight. I’ve got a two hour flight tomorrow and a sexy slut to fuck…so I better get a good night’s sleep. See you tomorrow.

A few minutes after she got home, again she was wearing nylons, she went to her room and a couple of minutes later I received a notification on my phone saying I had a new message.

I clicked on it as I watched television with Mom and Dad, Mom annoyingly already in pajamas and out of her hosiery, and read the message:

Lisa1996: you probably are already asleep tonight and I won’t get an answer back, so I’m going to say exactly what I’m feeling. Tomorrow, once the party is over, I want you to treat me like a slut. I will do whatever you want me to do. Just please, for one day I want to be more than the cute girl, I want to be the hot girl. The one no one can resist, the one everyone wants to fuck.

As I read the message from my horny sister, I suddenly worried. Although every word made my cock stiff as a rock, I realized we may crush her completely when tomorrow came and Adam didn’t show up.

The plan was for him not to show up, a flight delay, and then I would generously take his place and pretend to be her boyfriend at the party. Lisa had told all her coworkers, most of whom thought she was a lesbian, that she was bringing a guy to the party and, according to Andrea, a couple of her coworkers didn’t believe her.

Just then another message came.

Lisa1986: also, I haven’t touched my cunt as instructed, but I did just finish eating out your cousin in the changing room of a clothing store and then walked out with her pussy juice, no her cunt juice, on my face. Your cousin is a devious person too!!!

I got a text while reading Lisa’s message.

Wanna fuck? I’m in your bedroom.

My dick on fire, I wanted nothing else, other than maybe for the words to be coming from my sister.

I headed to my room and saw that Andrea was already on her knees on the floor waiting for my cock.

As I unbuckled my pants and slid my cock in her eager mouth, I wondered if I was going to get the best Christmas present ever…my sister.

…..

Lisa looked beautiful in her red dress, wearing beige thigh highs barely hidden by the shortness of it. She was also in three inch open toed high heels, so her pretty painted toenails were still in view. She was stressed because Adam was twenty minutes late. Which, of course, made perfect sense since he didn’t exist.

Mom tried to comfort her. “You look beautiful Lisa, with or without a man.”

“Mom, I really want to put a couple of those pretentious girls in their place,” Lisa said, just as the doorbell rang.

“Thank God,” Lisa sighed with relief as she went to the door. Opening it, she asked, her relief short lived, “Where’s Adam?”

“Flight is delayed,” Andrea said, “I’m so sorry.”

“Shit,” Lisa cursed, likely for the first time in front of our parents.

Dad looked up from the television, but knew better than to say anything.

“I can’t go to the party now, or to work ever again,” Lisa said over dramatically.

Andrea came in and said, looking at me briefly, “As I drove over here, I pondered what I could do to make this work.”

Lisa, near tears, said, “Get his plane to land.”

“Well, it hasn’t left yet, so that seems unlikely,” Andrea said, before adding, “but I did come up with an idea.”

“Turn back time so I didn’t say anything?” Lisa asked.

“No, but that would be a cool idea,” Andrea laughed. “Does anybody at your work know who your brother is?”

Lisa shook her head, “No, but why does that…wait are you suggesting I take my brother as my date?”

“I am, if he is willing,” Andrea said, all part of the plan. “He is kinda hot.”

“Thanks,” I smirked, “You’re kinda a nerd.”

Andrea shrugged, “He fits the profile.”

Lisa, talking in a way only Andrea was supposed to understand, said, “Trust me he doesn’t fit the profile.”

I stood up and said, “Lisa, if you want me to, I’ll do it.”

Lisa looked at me and said all hesitant, “I don’t know.”

Andrea pushed on, moving close enough to Lisa that no one else could hear, and said something.

Lisa finally said, “Fine! What have I got to lose.” Being kind of bossy, she instructed me, “Please shave first and then dress up in a suit and tie.”

“Yes, ma’am,” I sarcastically nodded.

I heard Mom say, as I headed downstairs, “That is incredibly sweet of him.”

I quickly shaved and got dressed and headed back upstairs, my cock already hard at the possibility, although sealing the deal was still going to be the toughest part. A part I really hadn’t thought through that well.

Andrea said, trying to stir the thought in Lisa’s head, “Wow, you sure clean up well.”

“Am I still only kinda hot?” I flirted.

“Stop flirting with my best friend,” Lisa scolded.

Mom said, “I want to take a picture first.”

“Seriously?” Lisa asked.

“My two children are all grown up,” Mom said, going for her camera.

I put my arm around her and she didn’t push it away as Mom took a few photos.

“Enjoy yourselves,” Mom said.

Andrea quipped back, “Yes, enjoy yourselves, you two.”

In the car, Lisa complained, “I can’t believe the flight got delayed. I finally thought I was going to….”

She stopped in mid-sentence.

“Going to what?” I asked.

“Put those girls in their place,” she covered.

“Lisa, if you want I’ll look like a lovelorn boy tonight,” I offered.

“That would be weird,” Lisa answered with a sigh.

“Weird, yes,” I agreed, “but only you and I will know that. Everyone else will think you have a hot guy in lust with you.”

“In lust with me?” She asked, looking at me.

“Yes,” I nodded, “someone who sees you as a beautiful girl he wants to devour whole.” Using my own internet words at the end definitely caused her cheeks to go red.

She sighed, “It’s just I was so really looking forward to this night, this date.”

“I understand,” I nodded, “but I’ll be him as best as I can.”

“Trust me,” she sighed again, “You can’t be him.”

“Trust me,” I countered, “I can be better.”

She then told me my background, which was all the things about the fake me, which was easy to do, since fake me was me.

There was awkward silence the rest of the way, and once we got there she said, “Please don’t embarrass me.”

“Lisa, I’ll be a perfect date tonight,” I smiled. “All the girls will be jealous of you.”

“I wish,” she sighed again before getting out of the car.

We walked into the fancy restaurant and I slyly took her hand in mine. She looked at me surprised, “We need to look like a couple.”

She just nodded, as I intertwined our fingers.

Once in the restaurant, a cute waitress wearing black pantyhose led us to a back room.

Lisa noticed me checking her out and whispered, “Could you not check out other girls while you’re pretending to be with me?”

“Sorry,” I sincerely apologized. “tonight my attention is strictly on you.”

“A bit creepy, but good,” Lisa said, before adding, “Begin acting now.”

We entered a room with about twenty people there, all dressed to the nines, some in nylons. I focused my attention on Lisa who immediately looked uncomfortable.

I whispered, “Remember, I’m here for you Lisa.”

Just then, a beautiful redhead walked over and greeted us, her tone dripping with mock surprise, “He’s real and yummy.”

I shot back, looking at her clearly fake tits, “And you’re 88% percent real.”

“What?” She gasped, even though she knew exactly what I was implying.

Lisa laughed, “Well, that answers one question I had about you, Emily.”

“You bitch,” she said through gritted teeth.

“Takes one to know one,” she countered, suddenly feeling confident.

Emily walked away in a huff and I apologized, “Sorry, I probably shouldn’t have said that, but no one insults my date.”

Lisa smiled for the first time since Andrea suggested I be her date, “No, that was awesome.”

The next hour and a half, we ate at a long table, thankfully Emily was at the opposite end, although her eyes shot daggers at us all through dinner. We visited politely and on a few occasions I put my arm around her. When I went to the restroom, I leaned over and kissed her cheek. Trying to make this look as authentic as possible, all the while trying to stir feelings inside her.

I went to the washroom and when I returned they were beginning to wrap up and prepare to head to the opera house. Apparently, limos were taking us there and bringing us back to the restaurant for a late night dessert.

I took Lisa’s hand and whispered, “Just so you know, you do look beautiful tonight.”

Lisa blushed, “Thank you, you’re quite handsome yourself.”

“I clean up well,” I joked.

“Yes, you do,” she nodded, although not in the flirty way women often talk to me.

“If you weren’t my sister I would be all over you,” I said, trying to advance my agenda.

Lisa laughed, before smiling ever so coyly, “And I just may let you.”

Her tone and smile made my cock stiffen as I led her out into the fresh fall air and into the second limo in line. As we sat down, the boss and his wife, who were sitting across from us, both pointed up.

We both looked up and saw the mistletoe.

I smiled, thinking someone above was watching out for me. I leaned in, Lisa’s eyes were big with nervousness, and kissed her. It wasn’t a passionate, tongue exploring kiss, but it wasn’t a sister and brother kiss either. I pulled her head to mine, so she wouldn’t move away after a brief second and kissed her tenderly, hoping to stir some heat down below and confusion upstairs.

Breaking the kiss, her boss’s wife quipped, “Oh, to be young again.”

I looked at Lisa, who had a completely unreadable look on her face. Clearly, the kiss had impacted her, although I couldn’t tell how. Was it enough to have her thinking what I wanted her to be thinking? Only time would tell.

My fingers entwined hers and my thumb made soft circles on her hand as the drive continued and we engaged in small talk with her friendly boss and his equally friendly wife.

We reached the theatre and again we were hand in hand, this time she took mine, as we walked into the beautiful theatre.

Again mistletoe was above a doorway. I turned to her and was about to ask her if we should kiss again when she leaned in and kissed me. This kiss had a little more urgency, a little more passion than the first one, although we both refrained from shoving our tongues down each other’s throats. It was a very intimate kiss, the kind that one has early in a relationship when everything is new and exciting. The tent in my pants implied it was indeed new and exciting.

Breaking the kiss, I purposely adjusted myself and she noticed and asked, ever so slyly, dripping with flirtation, Lisa clearly a different girl than the one I had known my whole life, “Is that because of me?”

“If you weren’t my sister,” I countered, “this date would have a very different ending.”

“How so?” She questioned, taking my hand.

“You don’t want to know the answer to that,” I replied, wanting to draw her in.

“Maybe I do,” she countered, as we continued walking.

“But you’re my sister,” I pointed out.

“And if I wasn’t?” She asked.

“Your mouth would be full right now,” I bluntly said, going for broke.

“With what?” She asked, actually batting her eyes, obviously knowing exactly what I was implying,

“Lisa!” I faked gasped, looking shocked.

“You started it with your big stud talk,” she countered, before shocking me as she moved her hand to my crotch and gave it a squeeze. She explained, “Just doing some recon for Andrea, she wanted to know how big you are.”

I stammered, actually stunned by her forward behaviour, “L-L-Lisa!”

She smiled, giving another firm squeeze before saying, “if you weren’t my brother you would be moaning those words, instead of stammering them.”

Before I could respond, she leaned in kissed me quickly on the lips, and said, “I need to use the ladies room before the show starts.”

I watched her walk away in complete awe of what just transpired…I had just gone from being the hunter to feeling I was suddenly the prey.

I quickly used the restroom too, throwing some cold water on my face, trying to cool down both figuratively and literally, as I focused on the end game plan. It seemed to be working even better than I anticipated…and the plausibility of success had just increased exponentially from the slim percentage the evening started at.

I returned to the lobby and waited another five minutes before Lisa returned, talking on her phone.

When she reached me, she hung up and I asked, “Who you talking to?”

“Andrea,” she answered, “she was checking to see if you were being a good date.”

“And what did you tell her?” I asked, playfully.

“That the jury was still out on how the night would end,” she replied, more innuendo.

She took my hand and led me into the theatre as I said, “You did not.”

“I did too,” she answered, a sly smile on her face, before adding, stressing every word, just as we got to the aisle, “We tell each other everything.”

My eyes went big. What was she implying? That she thought she and Andrea tell each other everything, or that she and Andrea actually do tell each other everything? Did Lisa know Andrea and I were fucking? Did she know that this was all an elaborate plan to fuck her? Did she want me to fuck her? All these questions seemed ludicrous and yet based on her last few statements and her sudden shift in behaviour it wasn’t out of the realm of possibility.

Usually in charge, I was suddenly flustered and doubting myself. Yet, I couldn’t ask more questions as she led me past other patrons and to our seats.

Once seated, her legs crossed and her heel dangling from her foot, another constant distraction, I tried to figure out what exactly she knew and how I could find out for sure.

She asked, “What’re you thinking?” Yet her tone implied she knew exactly what I was thinking.

I lied, trying to play it cool, and unable to say anything I wanted to say with people all around us, the show about to start, “Just wondering what’s gotten into you.”

She leaned towards my ear, “I’ll tell you what hasn’t gotten into me.”

Her hot breath and her implied implications made my cock instantly rise.

Just then her shoe dropped to the floor. I glanced down and stared at her beautiful stocking-clad foot. Her toes perfectly manicured and looking so sexy wrapped in sheer silk.

She wiggled her toes and said, “Adam is a nylon guy.”

I clarified, while still staring at her foot, “All guys are nylon guys.”

“Really?” she asked, moving her foot up onto my knee, “Why?”

“The look, the feel, the allure,” I answered, although I could truthfully never understand what actually turned me on about them.

“These are twenty dollar nylons,” Lisa said, putting her hand on her ankle and moving slowly up. “They are super soft.”

“They do really accentuate your legs and feet,” I complimented.

“Feel it,” she offered.

I couldn’t resist such an offer, such a temptation, as I put my hand on the top of her foot and slowly slid it up to her ankle and calf.

“I’ve noticed you staring at mom’s legs and feet often,” she revealed a moment later, just as the lights began dimming and the music started.

She moved her foot away, leaving my head spinning with what had just transpired over the past fifteen minutes. The next hour plus I vaguely watched the Broadway production, which was amazing, all the while thinking I was the Phantom and she Christine…although it seemed she had already taken off my mask.

As the lights came on for intermission, Lisa’s boss asked, “Enjoying the show?”

Lisa answered, “It was pretty hot,” as she squeezed my hand as if implying she was talking about something else.

I added, “Yes, the play is full of complex characters.”

Lisa added, looking directly at me, “Yes, you need to see past the outer appearance to really get to know them.”

The boss’s wife laughed, “I think you two are having one of those inside joke conversations.”

Lisa laughed, “Sorry, we’re still in that early stage of our relationship.”

The boss quipped, “Oh, I remember those days.”

“Shut up, Frank,” the wife playfully joked.

“Just saying, we were pretty wild back then,” he continued.

“And I’m not now?” She questioned.

“I plead the fifth,” he said, putting his hands up, knowing he was only digging himself into a deeper hole.

“Well, we haven’t gotten to the wild stuff yet,” I said, hinting to Lisa.

Lisa quipped back, “But the night is still young.”

“I’ve never seen this side of you,” Frank said, as we made our way out to the lobby.

Lisa shrugged, again squeezing my hand, “All of us are more than we are perceived.”

“Well, I like the more outgoing you,” he approved.

“I do too,” she nodded, before she and Frank’s wife went to the restroom to freshen up.

Frank and I talked sports, grabbed a couple drinks on him, and waited for the women to do whatever women do when they go to the restroom. For the record, men like to think you’re having lesbian trysts, but we know it’s more likely you’re just talking about us.

I had finished my first drink and was sipping on the other when the ladies returned giggling. The boss’s wife said, “I can’t believe you haven’t made a move on her yet.”

“P-p-pardon,” I stammered.

“Lisa was telling me that you’ve known her forever, but that your first kiss was just today because of mistletoe in the limo,” she explained.

My face probably showed my shock, but I recovered quickly. “Well, I’m a gentleman.”

The tipsy wife leaned towards me and whispered, although it was loud enough for Lisa to hear, “Sometimes a lady needs a man who knows what he wants and just takes it.”

“Is that so?” I asked, glancing at Lisa who was watching and listening intently.

Lisa nodded, moving closer to me so only I could hear her, “Sometimes a lady wants to be a tramp.”

My already hard cock flinched, as she walked away and went to get a drink with the boss’s wife, who apparently didn’t mind buying alcohol for a minor.

Frank quipped, “Looks like you’re getting some action tonight.”

I laughed, “I think the wine is getting to her.”

“Tammy always gets wild with some scotch,” Frank said.

“Well, make sure she is getting a scotch,” I suggested, both Frank and Tammy still a very attractive couple in their late forties.

“Get her into the scotch and she may want more than just me,” he quipped.

“Oh, the beautiful power of booze,” I quipped back.

“Indeed, it is the great equalizer,” he nodded, finishing his drink, just as the announcement that the show would begin in five minutes was made.

The ladies came back a couple minutes later and I asked, their drinks clearly not wine, “What are you two lovely ladies drinking?”

“Liquid courage,” Tammy answered, downing her drink.

Lisa added, as she put something made of cloth and slightly damp in my hand, “Tammy calls this panty remover. I know I wasn’t supposed to wear any, but I figured this tiny thing didn’t really count.” She downed the drink as I glanced down to realize she had just given me her very skimpy thong.

I gasped.

“Shall we return?” Frank asked.

“To the limo?” Tammy questioned, clearly frisky.

“Oh, you and scotch,” he said, shaking his head.

“You’ve never complained before,” she relied, moving close to him.

He took her hand and led her back to the theatre and I did the same with Lisa, no longer wondering if all her flirtation and innuendo was a coincidence. She definitely wanted to fuck me and now it was me having second thoughts, even as my free hand held onto her damp panties in my pocket.

Sitting back down, all my assumptions definitely true, my fantasy now within reach, I was a mess. Usually, I was in charge. I was the man. Yet, having my sister be so aggressive had thrown me a bit.

This sudden insecurity was compounded as the first song played and Lisa’s hand slid up my leg and rested harmlessly on my crotch. She didn’t squeeze, or rub, she just rested her hand on my very stiff cock.

Her hand lingering there drove me nuts. Song after song played, her hand not moving, a constant distraction, a frustrating tease. It was driving me nuts, I couldn’t help it any longer as I began to flick my cock in my dress pants, like a dog putting his head under someone’s hand for a pet.

She smiled slightly, but didn’t look at me or take the hint, instead keeping her gaze on the stage and her hand resting on my dick.

The last few songs, although beautiful, were excruciating as my dick begged for attention. I wanted to pull my dick out and make her suck me; I wanted to make her straddle me and ride my cock while both we and the show reached a climactic end; I wanted to throw her on the stage, spread her legs and pull her ankles to her ears as I buried my cock deep in her. These thoughts only made my cock want attention more.

When the show finally ended, she gave my cock a firm squeeze and whispered, “You should probably take care of that poor thing,” before standing up for the standing ovation.

I took a moment, stood up, adjusted myself and joined the rest of the audience in their admiration of the brilliant show we had all just witnessed. Yet, I was already envisioning my own after show, one where the crazy incest plan of mine came to fruition.

Eventually, we all filtered out of the theatre, everyone talking about how great it was. Lisa’s hand was again in mine, and I couldn’t explain why it felt so right.

We returned back to the limo and as the driver began driving, I noticed that Tammy was not so slyly rubbing Frank’s cock. Frank shifted himself to try and hide the act, but it was pretty obvious.

He asked, “How did you two enjoy the show?”

“It was amazing,” Lisa said, slipping out of her heels, again teasing me with her stocking-clad feet. “I’ve seen the movie and fantasized about seeing it live forever, but actually witnessing it was the ultimate experience.”

I agreed, answering with two separate meanings, “I felt I was on the edge the whole show.”

Tammy added, “The Phantom was hot.”

Lisa agreed, putting both her legs across my lap, “I’d let him take me to his underground love dungeon and have his way with me.”

Wanting full clarity, I asked, as I instinctively began massaging her left foot, “You want to be taken captive and made a love slave?”

“God, yes,” Lisa agreed, “I want a man who wants me more than anything else and then takes what he wants.”

“We all want that,” Tammy added, giving a look to her husband.

Frank said, “I told you…scotch.”

“It liberates my inhibitions,” Tammy, quite drunk, declared, as she suddenly began trying to fish out his cock.

“Tammy!” Frank gasped, “We have guests.”

“They want to fuck, too,” Tammy said, continuing to attempt to get his cock, although she wasn’t successful.

“We can resume this once we get home,” Frank said.

“Promise?” She asked, siting back up.

“Of course,” he nodded, although giving me a look that implied that she would likely pass out before that.

As if on cue, the drunk wife just passed out, falling into his shoulder.

Frank apologized, “I’m sorry, she can get very adventurous when she drinks.”

Lisa said, “It’s good to let loose once and in a while.”

“Agreed,” Frank nodded, “but not in front of our employees.”

“We won’t tell,” Lisa smiled, giving him a wink.

“Would you two lovebirds like to go for a drive around the city on your own tonight?” Frank asked.

“Really?” Lisa asked.

“Sure,” he said. “I paid for them until 2am so no one drove home intoxicated.”

“That would be great,” Lisa said, giving me a look that dripped with intention.

Frank, knowing exactly what we were both thinking, added, “The driver can stop wherever you want, take you wherever you want or just drive around.”

“Thanks, Frank,” Lisa acknowledged.

“Yes, that is very generous,” I added, my mind still spinning with the possibility of what likely was about to happen, as I switched to massaging her right foot. The feel of her foot, the silk, had me completely smitten with Lisa not as my sister, not as another conquest, but as someone I desperately wanted…needed.

“Press that button there,” he pointed, pressing a button, “if you want the window locked and the volume blocked.”

Lisa smiled, as she lifted her left leg up and placed her foot directly on my dick, “And why would we need to do that?”

“No reason,” he smiled back, clearly getting a full view of Lisa’s thigh high stockings, “just saying it’s an option if you two need some privacy.”

It was obvious we were both ready to burst at the seams the second the limo pulled back up to the restaurant. Frank woke Tammy up, who groggily climbed out of the limo and waved goodbye while winking at Lisa.

Frank briefly talked to the driver, before putting his head back in and saying, “I told him to just drive. If you want him to do anything else, let him know.”

“Thanks,” we both too quickly replied, both thinking the exact same thing.

“Have fun,” he said, before closing the door.

The second the limo started driving, we turned to each other and melted into one another. Our kisses this time were urgent, desperate, and hungry. My hand cupped her breast, her hand went to my cock. We were like two wild animals captivity at the zoo finally let out of our cages.

After a couple minutes of tongues exploring, hands roaming, I broke the kiss and asked, “Are you sure about this?”

“I’ve never been more sure about anything,” she answered, melting back into me.

Time became irrelevant as we began our journey of pleasure. She pulled off my tie, never once breaking from kissing me. She tugged off my suit jacket, breaking the kiss long enough for me to see the insatiable lust in her eyes. She wanted me more than any woman ever had before.

Once my suit jacket was off, she grabbed my dress shirt and ripped it open, her cavernous basic hunger written all over her actions.

I joked, “That was a forty dollar shirt.”

She moved her foot up to my chest, rubbing me with her silk foot as she quipped, “These are twenty dollars each and I bought two pairs.”

“Money well spent,” I nodded, my sister being the first to use my stocking fetish to entice me.

She rubbed her nylon feet on my chest and asked, “Isn’t this what you wanted?”

I whimpered, her sexy tone and foot play turning my brain into mush. “Yes, but I don’t want to force anything on you.”

Her right foot slid down my chest and rested firmly on my stiff cock in my pants. “Do I seem like I am having doubts?” She asked, demurely.

“When did you know?” I asked, as I took her left foot and took her stocking-toes in my mouth.

It was her time to whimper. “I was pretty sure you and Andrea were fucking, and then she slipped up about who she was fucking while I was apparently retrieving your cum from her cunt.”

I chuckled, as I made my way through her toes, “Yes, that was a little twisted I must admit.”

“After she left, I began to really replay the past couple of months, reread the chats, especially the one where you insisted I wear pantyhose, long knowing that you had a fetish by the way Mom’s legs in nylons always distracted you,” she continued.

Suddenly I wondered worriedly, “Do you think Mom has a clue?”

“I don’t see how she can’t,” she shrugged. “You practically stare and drool every time see is walking around in stocking-clad feet, especially when we are watching television.”

“Shit,” I sighed.

“If she does know, which I’m sure she does,” she continued, moving her other foot to my lips, while replacing the other on my cock, “she enjoys teasing you.”

“How do you figure that?” I asked, Mom my most common stroke fantasy, like many guys I imagine.

“Why would she stay in them all evening?” She asked, as I replicated the toe attention on her other foot.

“I’ve never thought about it,” I shrugged, “although she is definitely the reason for my nylon fetish.”

“Do you want to fuck Mom?” She asked, surprising me once again.

“What?” I asked.

“It’s a pretty straight forward question,” she continued, “do you want to fuck Mom?”

Figuring I was about to fuck my sister, being honest about my attraction to our mother wasn’t anything more twisted then we both were already committing. “Of course,” I admitted.

Shocking me once again, as she moved her feet back to the floor and moved to unbuckle my pants, she revealed, “Me too.”

“Seriously?” I asked, while I watched my once nerdy sister fish out my cock.

“Mmm-hmmm,” she purred, as she took it in her hands, “it’s as big as Andrea said it was.”

“So you knew of my intentions all day?” I asked, even though the answer was obvious.

She leaned forward and took my cock in her mouth. And bobbed up and down for a few seconds before asking, “Is that bad?”

She returned to sucking my cock as I agreed, “Yes, that is very, very bad.”

She continued sucking my cock before again stopping, my balls already on the brink of eruption, “Is sucking my brother’s big cock also bad?” She asked, looking up at me with such an innocent look the whole surreal situation had me overwhelmed.

I groaned, as she began taking all seven inches in her mouth with ease, something very few women had been able to do, “You’re a very bad girrrrl.”

She continued sucking and I knew my first load was about to erupt out of me, deciding I wanted to take control of the situation, something I wasn’t currently, I pulled out milliseconds before I was to come and grunted, “Open wide, little sister slut.”

She eagerly obeyed, opening her mouth and waiting for my cum. It was so hot as my cum rocketed out of me and splattered all over her face. Having not come all day, my first load was a big one. My cum hit her hair, forehead, cheek and lips, while a small amount hit the actual target.

As soon as my cum stopped shooting out of me like a cannon, she leaned forward and took my cock back into her mouth, like the cum hungry slut she wanted to be.

Wanting to return the favour, to taste her, I pushed her onto her back, and dove into her completely shaved cunt. Unlike most guys, I enjoyed eating pussy, my first girlfriend couldn’t come from getting fucked instead only from a good pussy munching. I not only knew how to use my tongue, but could find that needle in a haystack, the g-spot.

She was incredibly wet and she moaned the instant my tongue made contact with her. “Oh Goddddd.”

The mistake guys make about eating pussy is they think it is just a quick task to get to the main act…fucking. I see it as a critical part of the whole sexual relationship. I mean, why do women come back to me? Sure, I am pretty good looking, but the reality is there are lots of guys better looking than me. No, my allure is my ability to understand what women want and give it to them; it is also the ability to understand that the way to a woman’s sexual heart is through listening to them, understanding their needs, and truthfully, going down on them. Even all the chats with Lisa were about getting to know what she wanted.

My tongue explored her wet pussy lips, and teased her clit, constantly roaming like an explorer, being more of a teaser than a pleaser. Her breathing got heavy quickly; like me, her orgasm had been building and begging for release.

“Oh God, Eddie,” she moaned, clearly close to eruption.

I purred, putting her swollen clit between my lips, “Does baby sis want to come.”

“Pleasssssse,” she whimpered, my lips vibrating on her clit making her twitch.

I slid my finger inside her, searched and found her g-spot, and began tapping it like a drum while simultaneously flicking her clit with my tongue.

In seconds she was screaming and coming, “Fuuuuuuuuuuck!”

I continued the simultaneous double pleasure throughout her orgasm, her pussy juice somehow tasting like the sweetest I had ever tasted, Maybe it was or maybe it was just the reality of whose cunt I was savouring, but I kept lapping up her pussy cum, just like she had taken my cock back in her mouth after I covered her face.

Finally, she begged, still trembling, “Fuck me, Eddie, please, I have wanted this for so long.”

I wondered if she meant fucking me or getting fucked, but I wasn’t going to ask, my cock hard and ready for round two.

I pulled off my pants, moved between her nylon-clad legs and slammed into her with a raw lust that only happens a couple times in a man’s life.

“Oh Godddddd,” she moaned, as all seven inches of my thick cock filled her.

“So tiiiiiight,” I groaned, knowing I was the first cock to fill her.

“So biiiiiiig,” she moaned back.

Knowing she wanted to be fucked, not made love to, I slammed into her, the sounds of our two bodies crashing into each other echoing through the small space.

For minutes, both of us already having come, we fucked hard, not talking, just fucking, enjoying the immense pleasure we were giving each other.

When she did finally speak, she also wrapped her legs around me, and begged, “Deeper, baby, fill me deeper.”

The feeling of having her nylon-clad legs around me, only enhanced the already amazing sensation of fucking her, as I shifted from long strokes, to quicker deep thrusts trying to oblige her request.

“Oh yes,” she moaned, “soooo good.”

She lifted up her ass and began bucking forward, desperate to be filled deeper.

This position made for intense fucking, had sweat pouring down my brow as we gave each other quite a work out.

Another minute in this crazy position, my thighs getting tight, I grabbed her ankles, pulled them all the way to her ears, and leaned into her, reaching the new depths she desperately wanted.

“Ohhhhh fuckkkkkk, so fucking deeeeeeeep,” she screamed, as I watched her facial expressions of pleasure, something that always turned me on. I always loved to see the vulnerable moment of euphoria in a woman’s face when I made her come, and seeing it my sister was the ultimate moment of sexy sweetness when she came a second time after only a few deep thrusts.

“Yesssssssss!!!” she screamed, her body bending backwards even as I continued thrusting into her.

My own orgasm was building too, I continued to pound her as hard and deep as I could.

“Come in my cunt, big brother,” she demanded, “I want to feel you fill my cunt with your cum.”

I was just pondering where I was going to come, and hearing her beg for me to fill her with my load was all it took for me to make my decision, not thinking about the potential consequences, but rather the heat of the moment.

“Please, baby, I need your cum so bad,” she pleaded, staring at me with an insatiable hunger that made my balls erupt.

“Here it comes!!!” I grunted as I filled my sister’s cunt.

“Yes!!!!!!” she moaned, her eyes never leaving mine as I filled her.

This wasn’t just fucking, I thought to myself as I kept her gaze, this was an intimacy that was unlike any I had ever experienced before. Although I had liked many of the women I had been with, I had never loved them. This was a love that was much more than just a brother and sister, but I couldn’t explain it any better than that.

Finally, I pulled out of her, watching the cream pie in her cunt slowly slither out, as she weakly said, “Holy shit.”

“Any regrets?” I asked.

“That we didn’t do this sooner,” she smiled.

“Well, we can definitely make up for lost time,” I countered, sitting beside her.

“Promise?” she asked, her hands moving to my finally shrinking dick.

“Definitely,” I chuckled, as I watched her lean forward and take my cock back in her mouth.

The third load ended up going down her throat as she slowly sucked me for a good half hour, sucking on my balls, licking my long shaft and just pleasuring my cock.

The limo finally returned to the restaurant, we got ourselves dressed and returned to our car, both of us too tired to socialize.

Getting home, both our parents were asleep and after one last kiss, we went our separate ways.

We fucked every day until Christmas, including a threesome with Andrea at my secret rendezvous spot. Watching my sister eat pussy was damn hot, as was having both of them suck my cock together.

On Christmas day, well Christmas evening, after my dad had passed out like he always did during family gatherings, I was giving Lisa her great big Christmas present, banging her from behind as she leaned on her bed for support, when Mom walked in and caught us in the act.

I froze, my cock buried deep in my sister, as Lisa smiled and said, “About time, Mommy, get your ass in here.”

I gasped, as Mom closed the door, dropped her robe, revealing she was only in thigh high stockings, and walked over to us.

I stared in utter shock, as Mom dropped to her knees in front of me, pulled my cock out of her daughter and took it, sticky with pussy juice, into her mouth.

Lisa smiled as she turned around, “Merry Christmas, big brother.”

I was speechless. I couldn’t fathom when Lisa could have possibly seduced Mom in the week since I had taken her virginity. Yet obviously she had, as Mom was now bobbing on my cock.

“I’ll tell you the story later,” Lisa smiled, dropping onto her knees too.

I watched as Mom and Lisa took turns sucking my cock.

As Lisa deep throated me, Mom purred, “It’s as big as you said it was.”

Lisa moaned on my cock in response, as Mom moved and began sucking on my balls.

“Shittt,” I groaned, unable to say anything else.

A couple of minutes later, I warned, “I’m going to come soon.”

Both girls knelt before me, mouths wide open, as I stroked my cock.

Looking down at my two eager women, I shot my load directly at my Mom, another fantasy suddenly becoming a reality.

As soon as I was done, my sister and my Mom started making out, Lisa retrieving as much of my cum as she could.

When they broke the kiss, Mom looked up at me and asked, “Does my son want to fuck his mother?”

I replied by pulling her up, pushing her onto the bed, spreading her nylon-clad legs open and sliding into her trimmed, but not completely shaved, pussy.

“Oh yes, sonnnnnn,” she moaned, as I filled her.

Lisa straddled Mom’s face and ordered, “Get licking, Mommy-slut.”

I was in awe of Lisa calling our mother a ‘Mommy-slut’ and watched as our mother began licking Lisa.

“Keep fucking her,” Lisa ordered me, as I had stopped to watch the incestuous lesbian act.

I laughed, “Sorry, hard to stay focused.”

She smiled, “Men really can’t multitask.”

After a few minutes, Mom coming twice from my cock, I was about to erupt when Lisa demanded, “Fill Mom’s cunt with cum.”

Mom moaned, between licks, “Yes, baby, fill Mommy’s cunt.”

I wasn’t going to argue, as I spewed my seed deep inside her.

Soon after, Lisa came also from Mom’s tongue and we all collapsed on the bed.

“Merry Christmas,” Lisa quipped, after a couple of minutes of recovery silence.

“Indeed,” I laughed, my cock still hard, as I moved to Mom’s mouth.

“Merry Christmas to me,” she smiled, opening her mouth and taking my cock in.

Lisa smiled, watching Mom slowly suck my cock, and asked, “So, should we try to get Aunt Beverly to join us on New Year’s Eve?”

I laughed, Aunt Beverley being Mom’s younger, bustier, sister, “I think I’ve awakened a monster.”

Lisa leaned over Mom and took my cock, “Speaking of a monster,” she added, before taking it in her mouth.

They shared my cock for one more load, both bent on all fours as I took turns fucking them from behind, before coming inside Mom a second time.

Lisa retrieved my cum from Mom’s cunt as they got into a sixty-nine, getting each other off one final time.

As I watched, I said, more to myself than anyone else, “This is definitely the best Christmas ever.”

THE END