"Taking" My Sister's Virginity

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.