My Sister's Virginity: A Love Story

My Sister's Virginity: A Love Story (Very Kinky Love Story)

Summary: Comforting sister leads to wild sibling sex.

Note 1: This is a 2025 Valentine's Day Story so please vote.

Note 2: Thanks to Small_Island for editing and literally co-writing this story with me. Also Shuj and OhDave1 for last minute proofreading.

My Sister's Virginity: A Love Story (Very Kinky Love Story)

Seeing my sister looking so sad broke my heart.

Unlike most teenage brother and sister relationships, we got along... always had... perhaps it was because we spent nine months together in our mother's womb.

Even though fraternal rather than identical, we still seemed to share some of that mystical twin bond you hear so much about. I saw Sarah as my best friend. The one I could share all my secrets with, and she felt the same way about me.

As we passed the halfway point of our senior years in high school, we were also closing in on nineteen well ahead of the rest of our classmates, having started school a year late because Mom was a fashion model travelling the world at the time we should have been starting school.

Yet, no one would guess we were siblings, never mind twins, if they didn't know us. Yes, we both started tall and willowy like Mom, but I'd bulked up after puberty, while my sister seemed both skinny and bulky at the same time. I walked, perhaps even strutted, like the cocky athlete I was, while she tended to hunch in on herself; one moment she seemed a scarecrow and the next a shapeless blob. She seemed to have more of Mom's alluring features just under the surface of her face, while I had just enough to soften the rugged handsomeness I'd clearly drawn from our father.

Still, in the right lighting, with the right expression, the similarity was there, I'd seen it captured in two or three photos over the years. But our personalities, the way we carried ourselves, really set us apart and smothered any of the physical similarities.

I was outgoing, funny, and charismatic, if I do say so myself - a lot of other people did. All that led to me being a bit of a player as I matured. Then, to top it off, I was also a top jock. As I went through my final year of high school football, I was getting scholarship offers from a couple dozen schools because of my lightning speed and soft hands that managed to pull in any football I touched.

Sarah, on the other hand, also had dozens of scholarship offers but hers were all academic. She was a complete brain; an introvert, shy and sweet, who came across as a stereotypical uber-nerd. That said, when it was just the two of us, she had a foul mouth, like me, and was funny as fuck.

While I had been dating since my voice changed, Sarah had hardly scratched the surface of the dating world. But at the beginning of our senior year she began dating Blair, a nice guy nerd. I was happy for her, especially as I saw her start to come out of her shell. She began using light touches of make-up, occasionally letting her hair down, and added a few pieces to her wardrobe that made her look less like a 60-year-old spinster and more like a healthy teen who might just have a nice rack hiding under those loose blouses and baggy sweaters.

As those first months of school unravelled, I began to realize that my sister was not just cute, as I'd always thought, but downright pretty - damned pretty. And one warm Friday night when she and Blair came to cheer me on at a football game, she actually wore an outfit that confirmed that not only did she have a healthy chest, but she also had great legs... like our mom, who'd begun her modelling career as a leg model for a pantyhose company.

In fact, it was those legs (my mom's) that had certainly led to my long-held fascination with nylons. She wore them all the time and my mother was the ultimate MILF. I knew that every one of my buddies wanted to fuck her and I'd be lying if I denied that many of my stroke fantasies late at night were about my own mother. All that said, in recent years she'd gone fucking flaky on us and once we'd hit sixteen and got our drivers' licenses, was gone more than here, leaving my sister and I to fend for ourselves a lot, which had brought us even closer.

But in our senior year, once my sister started showcasing more of her body, my stroke fantasies began to shift from my mom to my sister.

It was suddenly clear that Sarah was a younger version of Mom, but a lot less shallow and vain than her. I mean, I love my mom, but she was hard to live with. Needy for attention and trying to live in a past that no longer existed. She also refused to let go of her youth.

I mean my mom was still hot and she knew it and used it to her advantage... truth was though, she was kind of a bitch and had become an even more absent mother since she started dating a musician only three years older than us. She had played the mom in his band's music video, 'I'd Rather Have Your Mom', which was exactly what the song title implies: a guy who wants to fuck his girlfriend's hot mom.

Thus, Sarah and I were often alone in a house way too big for two people. Our father, or as Mom referred to him, 'our sperm donor', we had never met because Mom said he didn't want anything to do with us, but I'm pretty confident she just had no idea who the father was. The stories of her pre-mom days were pretty wild... things most moms don't tell their children, but ours hadn't held back. So, I guess I can thank her not only for my nylons fetish, but my overall advanced expectations of sex.

Anyway, enough about us and how we got to this moment.

As 2025 began, it was me who was single and my sister who was attached.

I seldom kept a girlfriend for a long period of time as I always found flaws in them:

-too dumb

-too shallow

-too needy

-gave lousy head

-talked too much

I know that makes me shallow in turn, but I just could never connect with a girl on more than a sexual level... except for my sister.

Anyway, I walked into the house and saw Sarah crumpled into the corner of the couch, crying.

I immediately sat next to her and gathered her in my arms. "What's wrong, Sarah?" I asked as gently as I could.

"Blair, Blair, he..." she began to say through tears, "he, he, he dumped me."

"No way," I said, quite surprised by this. I mean, where the fuck was a nerd like Blair going to find someone not only as smart as him, but hot in her own right? Then it struck me that it was the day before Valentine's Day. Could you pick a meaner day to break up?

"And... and... and... cheated on me," she added, looking so vulnerable and sad at the same time.

"That asshole," I said, instantly getting mad.

"I-I-I...." She tried to speak but cried more.

I'd first wrapped my arms around her drawn-in body, but now I prized her open and pulled her in for a real hug. "It's okay, just let it out," I soothed. When I felt her finally begin to relax into me, it was impossible not to notice her firm breasts as they were suddenly pressing against my chest.

For a couple of minutes, I just held her in my arms, rubbing her back as she cried into my shoulder. Finally, she said, as she backed away and wiped the tears from her face, "And I was going to give him my virginity tomorrow."

"Oh, Sarah," I said, both horrified to hear that as you never want to hear about your sister getting fucked, but also devastated that she was rejected and dumped just the day before Valentine's Day. "Did he know?" I asked, thinking that while it would actually be the decent thing to break up and leave her cherry for a truer love, it might sting her even worse if she felt he broke it off because he didn't want to fuck her.

"It was going to be a surprise," she said, no longer crying.

"Well, the bastard," I said, "it's his loss."

"I even bought a special outfit and lingerie," she said.

"Well, again, that's his loss," I said, even as my mind registered the word lingerie. Then suddenly my hand was registering the same thing, as it drifted down to her leg and found, not the cotton of her long, plain skirt, but the smoothness of silk over the heat of skin. I peeked downward from the corner of my eye and saw that by balling herself up into the corner of the sofa, Sarah had caused her dress to hike up pretty high and expose a very surprising pair of nylons... just like our mother wore in real life and in my perverted fantasies. I know it was wrong to see my sister in a sexual way, doubly when I was trying to comfort her, but that was just where my mind went when I felt and saw the sexy material over a warm, firm calf.

"I can't believe he would do this," she said.

"Guys can be pigs," I said.

"So, I'm learning," she said, her facial expression shifting from sad to angry. The strong-willed, determined Sarah I knew suddenly coming back from the recesses of her sadness. "You're right, it's his loss."

"Plus, you should give your virginity to someone you care about deeply," I said.

"I thought that was him," she sighed. There was a pause before she asked, "Did you lose your virginity to someone you loved?"

I thought about my first time; it was almost a year ago now that I lost my formal penis-in-vagina virginity. It was actually with a woman down the street I did yard work for. It was a few days past my eighteenth and she invited me in for a glass of lemonade and a birthday gift. Before I knew it, she was sucking my dick. It literally felt like a porn scene. She swallowed my first load right in her kitchen since I didn't last long getting my first deep throat ever, but then I fucked her in the kitchen, the living room and her bedroom to multiple orgasms for her and another one for me. My second orgasm also hit her mouth, but only partially as my cock was outside of it as I stroked it after pulling out of her hot cunt and my cum was flying everywhere, painting her lovely MILF face. The thrill of coming on a woman's face started then and there. There is just something so incredibly hot about shooting a load on a girl's face. There is also something equally hot about a girl who will allow it. That image of my cum dripping from a lovely face seared itself into my brain and I've sought to repeat it ever since.

"No, but if I could go back in time, I would do things differently," I lied. The truth was, I wouldn't change a thing. It turned out that sexy lady wasn't the only MILF in the neighbourhood who'd been waiting for me to turn legal... and they weren't all single mothers. I'd learned a hell of a lot from them and had used those skills to seriously up my game with girls at my school. From the last few months of junior year, across the intervening summer, and on through the first half of senior year, I'd fucked over a dozen of my classmates and had continued with a few MILFs. My sister didn't know about the older women, but she did know I had a reputation at school as a player.

"I don't believe that," she said, reading me well.

"Okay, I'm a guy," I shrugged, "what can I say?"

"Plus, I know more about your reputation than you think," she added, with a raised eyebrow.

"Oh, and what is that?" I asked innocently, my hand still resting on her nylon-clad leg; I had unconsciously slid it up to her knee. The temptation to move my hand up and down and caress the nylon was hard to resist.

"Do you really want to know?" she asked, her tone unreadable.

"I'm a little scared, but sure, fire away," I said, assuming my reputation was as a male slut. One I could live with knowing I was moving far away from here in a few months.

"You have a big dick and fuck like a stud," she bluntly said, surprising me.

"Sarah!" I gasped, flattered by the words and happy to hear the ladies enjoyed me, but hearing it come out of my sweet sister's mouth was quite surreal and perversely quite a turn-on... my dick suddenly hard as a rock.

"That's what the girls say," she shrugged.

"Well, there could be worse rumours about me," I said with a laugh.

"There are some of those too," she said.

"There are?" I asked.

"Yeah, that you're kind of a male slut," she said. "Fuck 'em and dump 'em."

"Oh," I said, never having thought of it that way. I just wasn't into serious dating when I knew I was leaving here for college in the fall, plus as mentioned before, I'd just never really connected with a girl in a real raw way... that was perhaps partly my sister's fault because we were so close and I wanted a relationship of trust and honesty like I had with Sarah. That said, I was all up for fun and great sex... or average sex... I mean sex is sex.

I explained, "Yeah, I guess I just don't usually see enough in a girl to be in an actual relationship. Plus, what's the point, I'm moving far away from here soon."

"Don't feel too bad, the girls don't actually seem to mind," she said, then smiled. "Sure, a couple of them would like you to themselves, but they all appreciate that you don't lie about being in love just to get into their pants. And they all really appreciate what you do when they let you in." She waggled her eyebrows as she emphasized the word, really.

"Oh?" I questioned, shocked at how this had gone from comforting my devastated sister to her telling me the sex gossip about me.

"Yeah, some of the girls said you are the first guy to make them come," she bluntly said.

Of course, I was flattered. I mean this was mostly a pretty good rep to have. I was a strong believer in making sure a woman was satisfied. While some women could fake it, which I knew from reading online, I tried my best to make sure they truly came as I wanted them to have as good a time as I had. Half the time I made them come through fucking and half the time through oral. If a girl went down on me, I went down on her... I was a gentleman that way. Plus, hearing a woman beg to be fucked harder and hearing them scream with rapture was a real turn-on. I may be a male whore, but I am an orgasm-giving, considerate male whore.

Yet, I was bewildered other girls would tell my sister about my dick and my skills. "How do these conversations even come up?" I asked.

"Mostly second-hand from Beth and Avery," Sarah said. "They're my best conduit to the in-crowd where you seem to draw most of your conquests from and those girls apparently aren't shy about sharing notes on duds versus studs." Well, this was a surprising truth about girls I squirrelled away for future use.

"I seriously thought that was only a guy thing," I said, then clarified, "Although I have never fucked and told."

"Such a gentleman," she smirked.

"I try," I said.

"Thanks for cheering me up," she said, this surreal conversation seemingly coming to an end.

Then an idea popped into my head. I don't know where it came from, but as soon as it did, I knew it was a good one. Since I wasn't going steady with anyone, I had purposely not asked anyone out for Valentine's Day, I didn't want any girl to get the wrong impression that I wanted a long-term, loving relationship. "Hey, why don't you and I go out tomorrow?"

"Go out where?" she asked.

"Well, you said you got a new dress for tomorrow and I have a suit that's just been sitting in my closet since Cousin Greg's wedding last year," I said.

"You want to go on a date?" she asked, sounding perplexed.

"Not a date-date," I attempted to clarify, "but a date."

"Well, that clears things up," she laughed.

"I'll get a reservation at a top restaurant in Bakersfield and we'll get all dressed up and go out for a great meal, maybe go to a movie, forget about fuckhead and have fun," I suggested, although a secret part of me was perversely wondering what kind of lingerie she had purchased for her now ex-boyfriend... not that she would wear it tomorrow on a 'date' with her brother.

"Why not?" she shrugged, "I don't want to be home alone on yet another Valentine's Day."

"Yeah, exactly, no reason we should both stay at home on Valentine's Day," I said.

"Hey, why doesn't Super-Stud already have a Valentine's Day date?"

I looked deep into her eyes, actually quite mesmerizing eyes now that I'd taken off my brother filter and said, "Truth? I don't want to fake one of my girlfriends into thinking she has my heart when she only has my dick."

She paused only a second, then smiled. "That is such an asshole thing to say, but also saintly. I'm so glad we can speak honestly with each other. Please promise me that won't ever stop."

"Never," I assured her, even while I questioned my own veracity; if I was really being truthful, shouldn't I share how I'd lusted after our mother's nylon-clad legs and had begun to transfer that obsession to Sarah? Nah, not today.

"I was kinda bummed about being dateless on Valentine's Day," I said, "but if that left me free to help the woman who really is the most important in my life, then I'll put it down to Kismet and say thank you."

"You are a great brother," she said, hugging me more tightly, with more energy, her big breasts really pressing up against me.

"I really am," I agreed.

"Although a bit of a conceited asshole," she added, backing away.

"Hey," I said. "Not that you're wrong."

"But one who can back it up," she smiled, then looked directly at my crotch area. Apparently, while I'd been enjoying the pressure of her soft breasts against my chest, she'd been focused on my hard cock pressing against her. If she wasn't my sister, I would have taken that as a sign to move things to the next level.

"I do my best to never leave a woman unsatisfied," I replied, my hard dick begging for attention as it was throbbing even more now from her strange glance and her big tits.

"That is what I need," Sarah said, standing up. Unfortunately, that meant her long, loose skirt covered up her firm legs, but I still had a good view of her nylon-clad feet and pink-painted toenails. "A man who can sexually satisfy me."

"Sarah!" I said, legitimately shocked, even as I imagined giving her the attention she obviously craved from a man. I knew I could make her come and have the orgasm of her young life. Sure, since she was a virgin, the bar would have been pretty low, but I would definitely raise it for whoever came after me.

"What? A vibrator only does so much," she said, smiling as she wiggled her toes, drawing me to them.

"Too much information," I said jokingly, covering my ears even as I imagined her fucking herself.

"You think that's TMI? Hey, I know your dick is nine inches, I know you eat pussy until a girl comes, I know you like to talk nasty when you are fucking someone and even that you have ass-fucked at least one of our fellow seniors," she wildly listed off.

"Two actually," I said casually, trying to not look stunned by her wicked words that had my dick aching. Girls really did talk. "And it's nine-and-a-quarter inches if we're being accurate."

"Jesus," she said, again looking at my crotch area. "Blair was barely five. Actually, he may not have even been five."

Okay, so she may be a virgin but clearly not totally innocent. "Then he did you a favour," I said.

"Yeah, my vibe is bigger than him," she said.

"Well, don't worry, you'll find a guy with a nice-sized dick who treats you well."

"I want a man who can wait until I'm ready but then give me a really good fucking when I am," she said.

"This conversation is going so off-script," I joked. But then kept it going that way with my next question. "So, if you were making him wait, how do you know he was five inches?"

"He was whining so much about blue balls that I finally agreed to give him a hand job. But of course, as soon as it was through his fly he wanted me to blow him," she sneered.

"Well, he offered to return the favour, didn't he?"

"No, he said it was gross," she said.