Summary: Brother loses virginity to sister in one wild kinky night.
Note 1: This is a 2016 Halloween Contest Story so please vote.
Note 2: Thanks to TexBeethoven, Robert, Dave and Wayne for editing.
A Sister Surprise
“Please,” she pleaded again. Sarah was dressed in an incredibly sexy, very slutty Harley Quinn outfit, looking almost exactly like my favourite comic book character, but with a bonus. Her version of the fictitious character was enhanced by a sleek pair of thigh highs, and her sexy toes, adorned only in sheer silk, were in my clear view.
This Friday evening, three days before actual Halloween, she’d arrived home with a surprising request.
“But won’t they know I’m not Jake?” I pointed out. She was asking me to replace her ex-boyfriend for the evening. She was obviously desperate, since she’d driven an hour plus to get here from her sorority house and ask… no, she was actually begging me. She usually took everything that life threw her way in stride, but recent events had really gotten to her this time, and this evening’s Halloween party was very important to her.
“I don’t care. The asshole dumps me the day before Halloween, so I may as well let others know,” she answered, looking vulnerable and wounded behind her angry words… just like Harley Quinn often looked.
“I don’t know,” I said. I’d originally planned to be gaming online all night like I usually did.
“Please,” she begged, looking so fucking hot that my cock hardened… just like it often did when I checked out my super-hot older sister.
“Why do you even need me?” I asked her nylon-clad toes. Few people can brag of attractive feet, but there was something very special about hers, especially tonight. Especially in stockings.
“I can’t go to a Halloween party stag,” she explained. “I’ll get hit on all night by creeps who’ll think that since it’s Halloween, I’ll lower my standards all the way down to them.”
“Fine,” I replied all melodramatically, even though I’d already decided to do it the moment she’d asked. I mean she was inviting me to attend a college party… when truth be told, I’d never even been to a high school party, unless all-nighters playing ‘Call of Duty’ count. I agreed, making it look like I was super reluctant, “but you owe me, sis.”
“Anything,” she squeaked excitedly, bouncing up and down in front of me, her big tits bouncing, forcing me to shift my admiring gaze from her nylon-clad toes to her large breasts.
“I’ll keep you to that,” I warned, watching my sister’s tits jiggling.
If she wasn’t my sister, I’d be one of those creeps thinking that maybe – just maybe – I could get in
her panties, this close to ‘All Slut’s Night’, which is what I called Halloween. Not from personal
experience, but a guy can dream!
A night where society gives girls permission to ignore their morals and dignity, to dress like complete sluts.
Now I’m not complaining, far from it, and like I said, I had every intention of doing it for her… besides the chance to attend my first party that didn’t include a birthday cake, this was going to be an actual college party, I was dressing up like the Joker, and since no one would know we were related, I was going to get the status and envy of being the date for my hot sister… who was utterly beautiful… I mean a twelve out of ten… as besides outer beauty, she was a great person, and please don’t tell anybody, she was my best friend. I’m babbling, aren’t I? Have I mentioned my sister is really hot?
She was a cheerleader in college, and two-thirds of my nightly fantasies were about her… actually more like nine-tenths.
I know… I know… sick and twisted… but the truth. And again, please don’t tell anybody.
I mean, she regularly wore pantyhose or thigh highs, the lace tops which I admired on most days when she was home, since her skirts were quite short. I always knew when her period was, because she wore jeans (which made no sense to me except that she obviously didn’t feel sexy during that ‘god awful punishment God cursed on women’ as she called it).
Between her and my mother, a nurse, I grew up with nylons everywhere, and that was a good thing. They were easily my number one fetish, although I also got turned on by tits and asses… although a girl’s eyes, and her legs in nylon were the first two things I noticed in a girl. And my sister’s blue eyes were absolutely enchanting, making her look either innocent or sexy depending on how she wanted to be seen.
And dressed as Harley Quinn, her eyes had the opportunity of playing multiple roles. Harley mixed sweet and sexy better than anyone (go watch the new Suicide Squad movie and you’ll see exactly what I mean).
Still excited, she said, “I left the costume on your bed, hoping you’d do this for me.”
“Okay,” I nodded, really stressing the fiction that this was a major inconvenience by reminding her, “but you really owe me.”
“I promise, anything,” she repeated, looking so excited.
“Okay, I need to shower first though,” I said, needing to jerk off before we headed out… my sister as Harley Quinn, her bouncing tits and her feet in nylons really making my balls boil.
“Okay,” she nodded as she went to text someone, before adding, “Call me once you have the costume on. I’ll apply your make-up.”
“Okay,” I nodded, checking out her legs in thigh highs once more before heading to the bathroom.
I won’t bore you with my shower details, but it sure didn’t take long for me to unload all over the shower wall.
I cleaned up, put on deodorant, twice, and headed to my room in a towel. In my room I put on the costume, surprised at how tight the pants were… the shape of my cock was completely visible. I was staring at my cock in the mirror when Sarah came into my room and excitedly squealed, “Ready for meeeeeee?”
I looked up from the mirror and caught her staring at my crotch in the reflection.
“Oh my, um, that outfit is pretty tight,” she noticed as she looked up… her cheeks going red.
“I know,” I nodded, knowing that although I was kind of geeky looking, my arms and legs were actually pretty decently built.
Deciding to play mind games with my sister a bit more, I added “I’m not sure this is a good idea. This costume is super tight.”
Sarah was still gazing at my crotch as she argued, “You need to get out more, and a college party full of hot coeds will be good for you.”
I nodded, “That’s a great point,” my cock hardening in the tight pants as again I looked down at her sexy nylon-clad feet with her rainbow painted toenails… even as I pondered whether she was really staring at my bulge. I felt more like an eighties lead singer in leather pants than the Joker. My cock was so obviously hard, I had no choice but to shift my cock into a more comfortable position with my hand.
“Plus, bro, you get to be a bad boy for the night, and the girls all love a bad boy,” she said, avidly watching me adjust myself… this time making no bones (sorry) about the fact that she was checking out my crotch. She gained control of herself and ordered me to sit on the edge of my bed.
As I complied, I asked, “They do?” It should have been obvious to me if I just correlated who dated whom in high school, and how geeks like me were generally ignored.
“Oh yeah, girls love a bad boy,” she smiled in a tone dripping with naughtiness, beginning to apply my make-up.
As she worked on my face, I kept taking glances at her sexy nylon-clad feet… wishing I could touch them.
She noticed my footloose gaze as she did my make-up, and she unabashedly looked directly at my crotch ever so briefly before returning to my face.
She didn’t say anything, but wiggled her toes at me before saying, “You’re going to look incredible tonight.”
“Those are words no one has ever said about me,” I joked.
“Well, trust me, tonight’s a new beginning for you,” she promised.
Her thorough makeover of my face took over fifteen minutes before she declared, “I’m done. Go to my bedroom and take a look in the mirror.”
“Okay,” I nodded, my hard cock desperately needing another adjustment. I was curious whether the prominent bulge in my tight pants had been what had rattled her.
Although I’m a definitely a geek, I have a pretty big penis. Almost eight inches and thick, not that any girl would ever have a way of knowing this.
In her bedroom, I noticed a pair of pink panties hanging over the edge of her hamper which I was curious to smell (God I’m a pervert). I resisted the temptation, knowing she was following right behind me and instead adjusted my cock as I walked to her full length mirror.
“Amazing transformation, hey?” she said, as I stared at a super-villain in the mirror that didn’t look like me at all. Maybe tonight I could get away with being a ‘bad boy’.
“Yeah,” I nodded, thinking I looked a lot more like James the football quarterback, or Jake her ex-boyfriend, who was unintentionally responsible for my ‘dating’ my sister tonight.
“Seriously, you look hot,” she complimented, something I’d never expected to hear from my sister.
“Really?” I asked.
“Oh yeah,” she nodded, looking me over as if checking me out, admiring my crotch once again, while I returned the compliment to her feet. “Maybe it’s the bad boy look, but if you weren’t my brother I’d be all over you.”
“Nobody’s ever been ‘all over me’,” I pointed out, my cock twitching in my pants at her naughty words.
“Well, I have a hunch your fortune will be changing tonight,” she smiled, glancing at my crotch yet again, her eyes caressing a fully erect cock that these pants just couldn’t conceal.
“Well hopefully you’re not… joking,” I quipped neo-wittily, unable to resist the silly pun.
“Oh,” she smiled, her tone serious, permitting herself yet another glance at my crotch… she was definitely looking at my crotch… “there’s no joking here.”
This made my cock jerk again.
She noticed the movement too, but as her eyes broke away, she turned around and went to grab her boots. “So you ready to go?”
I turned and watched her sexy nylon-clad feet for as long as I could before they disappeared into a pair of sexy black boots, and I answered, “Sure.”
“Tonight you’re not my brother Joey,” she said, as she sat on the edge of her bed and slipped a foot sadly out of sight inside the first boot.
“No, I’m the Joker,” I nodded.
As she zipped up the first boot, her left nylon-clad foot still in full view, she clarified, “Yes, that too. But I want you to be Joe. I want you to be a guy with confidence, a guy who can speak to the ladies with charm, poise, and an edge. Own the Joker persona and use it to break out of your shyness.”
“Is it that easy?” I asked, never able to talk to girls… even when they were just my lab partners.
“Imagine they’re all me,” she suggested, “you have no problem talking to me, and I’m even frighteningly pretty.”
“But you’re different, you’re my sister,” I pointed out, even though for several years I’d had more sex fantasies about Sarah than about every other girl in the world combined. Although every other girl combined wouldn’t be very sexy; for a start she’d weigh zillions of tons. Sorry, that was a really stupid aside, but the point is that I’d secretly been in lust with my sister for a very long time.
“Tonight, I’m not your sister,” she declared. “I’m your date.”
“Really?” I asked.
“Yes,” she nodded as she dropped the second boot. I quickly walked over to her, dropped to my knees and grabbed the boot without thinking. Happily my instincts had bypassed my brain to put me in a position I really liked, and I took it from there.
“May I, my lady?” I smiled up at her, offering to put the boot on her.
“You may,” she laughed, as I grabbed her silky ankle with one hand, in awe of the softness (a fantasy coming true) and slowly slid on her other boot… staring fondly at her rainbow painted toenails until they disappeared into the dark hole of the boot.
I pulled the boot up, zipped it, and stood back up, my hard cock dying to get out of these pants… literally bursting at the seams.
I realized my crotch was almost directly at her eye level and there was no way she could miss seeing the full outline of my hard cock in these revealing pants.
She accepted my unintended invitation, smiling as she stared for a few seconds, before she reassured me, “Trust me bro… umm, Joe, you’re going to be very popular tonight. Very, very, popular.”
She shook her head a bit, as if erasing a naughty thought in her head (was she as intrigued by my cock as I was by her everything?). She stood up and said, “Let’s get going, we’re late.”
“Yes, dear,” I joked, as if we were an old couple.
She shook her head, “We’re not married, Joe. Call me Sarah or something sexy.”
“Goddess,” I suggested.
“Hard not to like that one,” she grinned appreciatively, as we left her room.
I followed like the lovesick puppy I was. Both because my sister/date was the hottest girl I knew, and also because Harley Quinn was my favourite comic book female… thus my two favourite women had now joined forces as one semi-fictitious hottie.
Having already had a couple of drinks, Sarah had me drive the hour plus drive to her sorority house while we chatted about school, hers and mine, Christmas, our parents, and especially Mom and how she was going to lose it when I went away to college next year, unfortunately turning her into an empty nester. I was definitely leaving the city, unlike my sister, and going to attend Harvard or Princeton or Yale… not sure which one I preferred yet.
When we arrived, she asked, “Ready, Joker?”
“Yes, Harley,” I nodded, imagining Suicide Squad and the wild, kinky sex they would have had.
We got out, and to my surprise she took my hand in hers. I sure didn’t resist, the handholding so intimate that although my cock had briefly gone to slumber during the drive, it instantly stirred to salute my… I still couldn’t believe it… my date.
She led me into the large house and my head started spinning. There were girls everywhere, and every one of them without exception was dressed in a skimpy outfit. There were tits, asses and legs everywhere… although almost no pantyhose or stockings… some fishnets, but only a couple, like my sis… my date!… wearing actual nylons.
“You’re a leg guy aren’t you, Joker?” she asked, seeing my head turning every which way.
“More a nylons guy,” I admitted, figuring no risk in letting her know that.
“So I dressed up perfectly for my man tonight,” she smiled, placing her hands on her legs and tracing them upwards as if smoothing wrinkles out of the silk. She watched me watching, and winked saucily.
“You always do,” I answered and then realized the implication of my response and stammered to correct myself, “I mean you always dress nice.”
“You mean in nylons?” she asked, smiling wickedly.
“Um, yeah,” I admitted, figuring the cat was out of the bag and although I was academically brilliant, my social game was definitely scored an ‘F’.
She was about to say something else when a redhead dressed as the sluttiest Pippi Longstocking ever, I think that was what she was going for, came up and gave Sarah a big hug.
“I’m happy you’re here,” the redhead burbled excitedly, clearly already a few drinks in.
“Sorry I’m late,” Sarah apologized.
“At least you’re here,” the redhead forgave, sounding relieved. “Andy’s here.”
“Have you talked to him?” Sarah asked.
“No, but I’ve been super tempted,” the Pippi twin answered.
“I’ve told you, you need to play hard to get,” Sarah advised, having given this advice before.
“Easy for you to say, you have Jake,” the redhead said, finally looking at me and after really looking at me added, “Waitaminit, you’re not Jake.”
Sarah answered, “I upgraded.”
“What?” The redhead asked.
Sarah, shocking me but clearly answering my question that yes indeed she’d noticed the size of my cock, she proudly pointed out the cock in my pants with a flamboyant gesture as if she were a gameshow model drawing attention to something wonderful behind a curtain. My cock’s shape was clearly defined, and was impressive, and the Pippi did indeed respond to it as something wonderful.
“Oooooh!” she giggled, staring.
“Yeah,” Sarah added, giving my… my… no, you perv… giving my hand a squeeze, “Size does matter.”
Ignoring my irrelevant hand and staring fixedly at the outline of my hard-on, the redhead replied, “I couldn’t agree more.” She finally looked up to my (also irrelevant) face and greeted, “Hi, I’m Amy.”
“I’m the Joker,” I replied, flattered that she seemed so impressed with my dick and enjoying the safety of the costume where I wasn’t a geek virgin, but maybe could be a suave stud.
“Well,” Amy smiled, returning her stare to its home in my crotch, “that’s no joke.”
I don’t know why I said it. A sudden burst of confidence or a desire to impress Amy or even to impress Sarah, but I replied, “You should see it when I unleash it to play.”
Amy flirted, “I imagine you can really ‘Pow Bam Pow’ with that thing.”
I loved how she was referencing the old Batman cartoons. I chuckled, “I do like to Boff Bam Pow.”
“I bet you do,” Amy purred, clearly flirting with me.
“He’s mine,” Sarah interjected, surprising me with a flash of possessiveness as she pulled me away from the first girl to ever flirt with me.
“Can’t we share?” Amy pursued, her eyes not leaving my cock.
“You’re insatiable,” my sister rebuked her with a smile, shaking her head to deny the blatant request, as she took my hand and began guiding me away through the throngs of people.
As I walked past the redhead, she reached over and grabbed my cock, making me gasp… I’d been here only three minutes, and I’d already broken my own record of girls touching my dick with a new count of one.
Sarah warned, “I’m pretty sure Amy has a few sexual diseases.”
“She grabbed my dick,” I pointed out, annoyed but not very, that I’d been pulled away from what seemed like a sure thing.
To my astonishment, Sarah stopped, turned around and grabbed my cock! And actually held onto it for a long moment while she said distinctly in a no-nonsense tone of voice, “You’re my date tonight. So this is mine.”
“Really?” I asked, stunned and thrilled to have my hot sister squeezing my dick.
“Yes really,” she nodded, her hand moving away. “We need to look like a couple. I can’t have people thinking I can’t get a date for Halloween, and they obviously can’t learn that you’re my brother.”
“Okay, okay,” I nodded. “I totally agree. But for the record, until two minutes ago no one had ever touched my dick.”
“No one? Ever?” she asked, looking surprised.
“Nope,” I nodded.
“Are you then,” she began, before pausing, “a virgin?”
I joked, “Yes, unless my own hand counts. If it does, I’m a very well experienced stud.”
“Oh,” she said, her expression a cross between saddened and intrigued. After a pause, she smiled, “Well, Joker, we can’t allow that sad condition to continue.”
My mouth fell open, and before I could manage to close it and ask what she meant, we started walking again as she led me through the throngs of costumed college people.
My cock was hard and impossible to conceal as I drooled at the many hot coeds dressed so sluttily.
Eventually we arrived in a kitchen with lots of booze and Sarah asked, “What do you like?”
“I have no idea,” I answered honestly, having tried beer and hated it. “But I hate beer.”
“Hmmmm,” she pondered, as she grabbed a bottle. “Let’s get you drunk so some sexy lady can take advantage of you.”
I don’t know why I allowed it to escape my lips, but I responded sincerely, “But you’re already the hottest one here.”