"Taking" My Sister's Virginity

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."