"Taking" My Sister's Virginity

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