Sibling Surprise

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Summary: Brother & sister foreplay escalates over time.

Note: This story is dedicated to Matt who requested it.

Note 2: All characters are at least 18 years of age.

Note 3: This is a NUDE DAY 2020 story so please vote.

Note 4: Thanks to Tex Beethoven, and Robert for editing this story.

Sibling Surprise

It was nice to be back home after my second year away at college. It was also nice to finally see my sister’s very hot friends live and in person. I’d been following my sister and her friends on her Instagram account all year, discovering that my sweet and popular sister had four amazingly sexy friends, who liked posting provocative pictures of themselves.

I’d spent the majority of my jerk off sessions reading erotica, which I found more stimulating than watching porn, but looking at pictures of ripe, cute eighteen-year-olds was also very arousing.

Amber had big tits that she found a way to perfectly showcase in every picture she was in.

Josie had a great figure that looked amazing in a bikini.

Shandra had her Latina booty going for her that resembled Beyoncé’s.

Cassie had amazingly long legs.

Allie, my sister, was almost always in the pictures, yet I didn’t really notice her.

No, I imagined myself jerking off all over Amber’s huge tits.

I imagined myself spewing a load all over Josie’s flat tummy.

I imagined myself exploding a load all over Shandra’s big booty.

I imagined spraying my load all over Cassie’s long legs… she was the only one who often wore nylons in the photos, other than my sister, who also often wore them… such a rarity among teens and college girls today.

Imagine being the key word here, since being painfully shy, I’d never even kissed a girl (except for my mom on the cheek sometimes), let alone ever done anything more adventurous.

I had hundreds of photos of the five of them, or any mix and match of them, saved on my computer: in cheerleader outfits, in bikinis, dressed up, and more. Yes, I know it’s a little pathetic stalking my sister and her friends on social media, instead of actually living my life at college… but like I said, I’m excessively shy, and my words get all jumbled up in my mouth whenever I try talking to a pretty girl.

So instead, I lived vicariously through my sister’s friends and my fleshlight… which is supposedly like the real thing, but I had to take their word for it.

I got up from my laptop and looked out the upstairs window into our backyard. I stared at Cassie tanning… her long legs looking even better live.

I also couldn’t help but stare at Amber’s tits as she sat on the edge of the pool, her feet dangling in the water.

Then I noticed my sister.

She’d always been in the photos… but only as background noise to her friends… not because she wasn’t cute, nor because she didn’t have a great body… but just because she was my sister.

Yet suddenly, at this moment, as I looked out my window, I saw my sister for the first time. Not as my sister, but as a beautiful girl.

Her cute, flat tummy.

Her tight ass.

Her long legs.

Her small, perky tits.

Her beautiful high arched feet.

Her legs in nylons in over half of the pictures.

Her cute perfectly manicured toes in a quarter of them… she’d never worn nylons when I lived at home… but she seemed to start doing so in her senior year of high school.

My seven-inch cock was raging as I realized my sister was a perfect blend of all her friends. The perfect package. How had I never noticed her before?

I began slowly stroking myself as I admired her from afar.

My balls were bubbling in a couple of minutes, before I spewed my load all over the wall… just as my sister looked up and saw me wearing my cum face.

I quickly moved away… but it was too late… I was busted.

I cleaned up my mess, shaking my head at the reality I’d jerked off to the sight of my kid sister.

I was disgusted at myself.

What kind of pervert would drool over his own sister?


I was just leaving my room to go and grab lunch, when Allie confronted me from out of nowhere, saying, “Stop perving on my friends.”

“I wasn’t,” I lied, as I noticed how her curly copper hair and green eyes were so hypnotic and so alluring.

“Yeah, right,” she said. “It’s creepy.”

I looked down at her small, perky tits, her nipples poking out through her blue flowered bikini. “I was just checking what it was like outside.”

“Yeah, whatever,” she said. “Why don’t you actually go outside, if you want to check the weather.”

“I will, I will,” I said, as she turned and walked away. I, of course, stared at her ass, so perfectly framed by her bikini.

I sighed at the fact that just a couple of minutes after cursing myself for jerking off over my sister, I was now staring at her ass, and my cock was hard again.

I was often hard.

Three jerk offs in a day was a ankara escort slow day for me.

I turned around, went back into my room and started flipping through photos, and this time I focused on my sister in every one of them… the other girls becoming the background noise.

I noticed Allie’s sweet smile.

I noticed her green eyes.

I noticed her body, splattered with freckles from head to toe… like mine.

I noticed her tits that although small, were so perfect for her petite frame.

I noticed her long, flaming, copper hair… that looked so much better on her than it did on me.

I noticed her firm ass, that now I’d had my epiphany, I just wanted to squeeze.

I noticed her legs, that accentuated the rest of her body so perfectly.

She was the perfect package.

Fuck, my newest crush was on my sister!


That afternoon I was watching television, binge watching Chuck, a greatly underrated show, when Allie came in and plopped down on the couch beside me.

This was a surprise.

My cock instantly hardened.

She asked, “Which friend of mine were you drooling over?”

“None of them,” I said, which was kind of true. I had been drooling over each of them, but only before targeting my attention on her.

“Yeah, right,” she scoffed, as she surprised me by swinging her feet onto my lap.

“W-w-what are you doing?” I stammered, as her heels were suddenly on my crotch, and her nylon-clad feet were suddenly front and centre. Why was she even wearing nylons in the middle of the afternoon on a 90° plus day?

“I’m demanding that you give me a foot massage,” she said, wiggling her toes and putting pressure on my hard cock. “And if you don’t, I’ll tell Mom and Dad you’re perving on my friends.”

It wasn’t much of a threat, since my parents wouldn’t likely give much merit to her accusation… I’d always been their perfectly well-behaved child. (Because I was too shy to be any other way.) Yet I wasn’t about to miss this opportunity to massage my sister’s cute feet, and to feel them through her nylons. One of my many unfulfilled fantasies was to feel nylons on a girl, and/or to get a nylon foot job.

Her toenails, painted a cute blue, looked even more tantalizing in her beige shade of nylons.

I grabbed her left foot and said, acting like this task was a huge inconvenience, “Fine, whatever.”

She switched the channel to some lame reality show, and played with her phone.

Her feet in these stockings were so, so very soft.

I massaged each foot for a few minutes, my cock rock hard, as I ignored the terrible television show that made me feel dumber anytime I happened to listen to them talking.

A couple times she moaned ever so softly, which turned me on, as it meant I was doing a good job, and I’d never heard a woman moan before… except in porn.

“Massage my toes, perv,” she ordered, as she continued pecking away on her phone.

“Whatever,” I said, although I was actually excited to get to do just that.

For a couple more minutes, I went through each individual toe. She moaned a few more times, and feeling a little confidence, I flinched my cock under her feet.

She didn’t seem to notice it at all.

Suddenly obsessed with her nylon-clad feet, I lifted her foot up to my lips, and sucked her pinky toe, needing to taste this nylon-clad foot.

“What the fuck are you doing?” she asked, her expression showing how disgusted she was.

“I-I-I,” I stammered, unsure of what to say. I couldn’t defend taking this liberty.

“You just sucked my toe,” she accused, although oddly not pulling her foot away.

“I don’t know what came over me,” I blathered, which was somewhat true. I really didn’t know why I did it other than it was there, and I was drawn to her perfectly manicured toes.

“You like feet, big brother?”

“Um, I like everything about girls,” I said, not wanting to be seen as a foot fetish perv.

“Or is it particularly my nylons?”

“They are nice,” I admitted.

She requested, seemingly amused, “Keep sucking on my toes, then. It felt nice.”

“You sure?” I asked, shocked.

“You obviously want to,” she said.

“Okay,” I said, sucking another toe into my mouth.

“So what else do you like about women?” she asked.

“Everything,” I said, as I sucked her toes and massaged her foot at the same time. “A woman’s smile, her breasts, ass, legs.”

“Not her pussy?”

“And her pussy,” I admitted.

“But you’ve never seen a pussy except in pictures, have you?” she asked, even though her tone told me she knew the answer.

“I have a problem even just talking to girls,” I admitted, trying to defend the reality of how pathetic I was sounding, or the even more obvious truth: that I was a virgin… unless you counted my three fleshlights, that I’d fucked many, many times.

“I have it on excellent authority that I’m a girl,” she pointed out, as she switched the foot for me to worship next.

“But you’re my sister,” I explained, even though it seemed we’d already crossed escort ankara that invisible line of taboo.

I realized at that moment that Allie was indeed the only pretty girl anywhere I was comfortable talking with.

“Am I not hot enough to get you stammering?” she asked, as I took her other foot in my hand.

“No, you’re definitely hot enough,” I said, in awe that this conversation had taken such a surprising detour.

“But my tits are smaller than Amber’s,” she said, as I sucked on her cute pinky toe.

“I suppose, yet yours are the perfect size,” I said, having already resolved that issue to my own satisfaction earlier today.

“You’re sure about that?” she asked, as she raised her shirt to reveal she wasn’t wearing a bra. Her hard nipples were looking right at me.

“I-I-I’m v-very sure,” I stammered, staring at my sister’s perkily perfect tits. My cock was raging in my pants as I held her foot in my hand.

“So you’re telling me you like your baby sister’s tits?” she probed, seeming to love teasing me so relentlessly.

“They’re perfect,” I answered, my eyes fixated on them.

She pulled her shirt back down and asked, “Do you think my legs are as hot as Cassie’s?”

“In these nylons, definitely,” I said, sucking on another toe.

“You like these nylons?” she asked, as she placed both her feet directly on my crotch.

“Yes,” I groaned.

“Ooooooh, is this hard on because of me?” she asked wickedly.

“It’s not not because of you,” I answered, letting out another moan, as she began playfully rubbing her feet back and forth over my cock.

“This feels pretty big, big brother,” she said, still rubbing my cock.

“Oh, God,” I moaned, about to come already.

“Is my big brother packing a big dick?” she queried, continuing to rub my cock.

“Ooooooooh,” I moaned, as I spasmed, and OMG… came in my pants!

“Did I just make you come?”

“S-s-sorry,” I replied weakly, as my orgasm overwhelmed me, even as shame at coming so quickly also hit me.

“That was fun,” she shrugged, jumping up and walking away… leaving me to wallow in my own cum, and completely shocked.

As I sat there bewildered, I said to myself, “Well that was unexpected!”


The rest of the day was a whirlwind of confusion.

I actually pinched myself to make sure I was really awake, and that this wasn’t some crazy dream.

I replayed the day over and over.

In awe of what had happened.

Allie went out for a little after the surprise foot job, and she didn’t return.

I was in bed, on my laptop, flipping through pretty much every photo of my sister… now completely ignoring whoever else was in the photo.

I couldn’t imagine how I hadn’t noticed her for all this time.

She was absolutely gorgeous!

Her smile.

Her eyes.

Her hair.

Her tits.

Her hips.

Her ass.

Her legs.

Her feet.


I had my cock inside my fleshlight and was slowly fucking myself, when I was interrupted by my sister.

“Oh my,” she gasped as she closed the door behind her that evening… wearing a blue dress and the same nylons as this afternoon… or so I assumed, since they were the same colour.

I snapped the laptop shut, not wanting her to see what I was looking at. Yet my cock was still inside the fleshlight.

“Is this because of me?” she asked, walking over to the bed.

“What? No… I,” I babbled.

“Mmmmmmmm,” she said, reaching for the fleshlight. “I’ve been curious about how big you are, ever since this afternoon’s little foot job.”

“I… um… well… I…” I continued sounding like the totally inexperienced guy I was.

She pulled the fleshlight off my cock, making me groan with pleasure, and gasped, “Well… wow! My big brother is BIG!”

“After how quick Joey came inside me tonight, if you weren’t my brother, I’d straddle this big dick and go for a ride,” she said, staring at my dick similarly to how I’d stared at her tits earlier. Joey was her linebacker boyfriend.

My cock continued saluting my baby sister, as she suddenly grabbed my computer and asked rhetorically, “And what was big brother stroking himself to?”

“Please Allie, give me back my computer,” I begged, reaching out with one hand while covering my dick with the other… finally.

“Don’t hide that monster away on my account,” she said, tugging my blanket hard, and revealing my hard dick again.

“Mom and Dad are home,” I protested, although I wasn’t really concerned about their having sex… they slept like logs.

She opened my laptop, and she froze. Obviously this wasn’t what she was expecting to find. I imagine she was anticipating seeing porn of some sort.

I stammered, “I-I-I can explain.”

“Can you?” she asked, as she flipped through the photos.

“Um, I, well,” I said, not sounding like a college guy on a full ride academic scholarship, but like an uneducated hillbilly.

“These pics are all of me,” she said, her tone inexplicable. She sounded shocked, flattered ankara escort bayan and annoyed, all at once.

“And of your friends,” I added, which I wasn’t sure if that made it more or less pathetic.

“How long have you been collecting these?” she asked, still giving me no clue to what she was feeling or thinking.

“All semester,” I admitted, feeling shame course through me at how pathetic I must look to her.

“I see,” she said, looking at me for the first time since discovering the photos.

“I’m sorry,” I repeated.

“Does that thing ever go down?” she asked, closing my laptop.

For a second time she wasn’t as mad as she should have been. I replied, “It has a mind of its own.”

“What’s it thinking right now?”

“That it needs to come again,” I answered, figuring there was no reason to hide behind false pretenses anymore.

“Want me to help?”

“Really?” I asked, still feeling like I was living in a dream world.

“Yeah, I want to see how this thing works,” she said, as she grabbed my hard cock and lowered the fleshlight onto it.

“Oh, fuck,” I moaned, knowing this was going to be another quick eruption.

“What are you fantasising about?” she asked, as she began masturbating me with the toy.

“You,” I admitted.

“Me? Okay, me doing what?” she asked in a sexy voice.

“Everything,” I answered.

“You can be more explicit than that, college boy,” she said, pausing her slow masturbation with the fleshlight.

Desperate to come, I answered, “What everything means, is that I want to face fuck your pretty mouth, suck on your tits, eat your pussy, suck on your nylon-clad feet, fuck your stocking feet, and to just plain fuck you.”

“Oh my,” she purred, as she resumed slowly masturbating me. “You really want to fuck your baby sister with your big cock?”

“God, yes,” I moaned.

“That’s so bad, big brother,” she purred, so sensual.

“Oh, fuck,” I groaned, so close to coming.

“You know… you’re a couple inches bigger than Joey,” she added before she ordered, “Come for me big brother, come inside this toy pussy, imagining it’s me.”

“Oh, fuck,” I trembled, before immediately erupting my load into the fake pussy… which felt so much more erotic when someone else, especially my hot sister, was manipulating the toy instead of me.

“Good boy,” she purred, as she continued milking my cock throughout my orgasm.

When I was finished, she pulled the toy off and observed, “You have a great cock, big brother.”

“Thanks,” I said, that being the most amazing compliment I’d ever received from anyone.

“The fact that Joey didn’t get me off earlier, added to your yummy big dick, has my pussy all wet,” she said, staring at my cock.

Was she thinking of straddling me? I wasn’t about to get soft anytime soon.

“What can I do for you?” I asked, trying to sound suave, when I was really giddy with excitement.

“Fuck me,” she said, shocking me to the core. Before I had time to say anything, she added, grabbing a Coke bottle I’d recently finished, “with this.”

She handed me the bottle, got onto the bed opposite me, lifted up her dress revealing she wasn’t in pantyhose but thigh highs, and spread her legs.

My eyes went wide at the thigh highs, and the fact she wasn’t wearing any underwear, and her completely shaved pussy was in plain sight right before me.

“Wow!” I said, captivated by what I was staring at.

“I only wear thigh highs,” she said. “Easier access to my pussy.”

“Wow!” I repeated, not yet moving, even though I should have been quickly moving between her legs.

“Like my shaved snatch, big brother?” she asked.

“It’s beautiful,” I said, still staring in awe.

“Are you going to fuck me or what?” she asked, as she moved her hand to her clit and began slowly rubbing herself.

“Yes, sorry,” I apologized, spinning around to move to her. “I’m just captivated by you.”

“How sweet,” she said, and then added, “now fuck your baby sister with that bottle.”

I moved between her legs, feeling a little brazen, and glided my hands up both of her nylon-clad legs.

As I was now staring at her pussy from very close, I grabbed the bottle and moved it very cautiously between my sister’s pussy lips, which were literally glistening.

“Just shove it in my pussy big brother, and fuck me,” she moaned, clearly turned on by the taboo incest thing, as she repeatedly called me big brother.

“As you wish,” I said in a complete daze, sliding the coke bottle inside my sister’s pussy and able to smell just the slightest exotic scent.

“Oh yes, shove it all the way in,” she moaned.

I did as she requested, and then began to slowly fuck her with it… captivated by watching the coke bottle going in and out of my sister’s pussy.

I wanted to eat her pussy.

I wanted to suck on that swollen clit.

I wanted to taste her wetness.

Yet I just enjoyed the privilege of fucking her with the bottle, and admiring her sweet pussy.

She began moaning louder as she demanded, “Harder, fuck me harder, big brother. Give it to me like you imagine doing when you jerk off.”

I pumped the Coke bottle in and out of her faster, as the sexy sounds of pleasure escaped her lips and made my still hard cock flinch.

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