Summary: Brother finds nude cheerleader pictures including his sister
Brother blackmails sister with nude photos found on phone
Note 1: This is a NUDE DAY 2015 Contest story.
Note 2: Thanks to Robert, goamz86, Wayne and Wordsmith1950 for editing this story.
My bitch cheerleader sister stormed into my room while I was in my bed, on my laptop watching, ironically, cheerleader porn, and jerking off. “Oh shit, wrong room.”
I gasped, dick in hand, completely humiliated to be caught jerking off, “Get out!”
“Oh shit,” she laughed, clearly quite drunk but realizing what I was doing. After a pause, she added, looking at my fully erect dick, and smiling, “Nice package you’ve been hiding, little brother.”
I am only three minutes younger than her. Although we are twins we are complete opposites.
She got the looks, I got the brains.
She’s a bitch, I’m a nice guy.
I repeated my demand, as I hid my raging hard on, behind my computer “Get out.”
“Oh, I’ve seen many dicks before,” she quipped.
“I imagine tonight alone that is true,” I shot back.
“What ya watching?” she asked, moving closer to me. “Anime porn?”
“Just leave,” I demanded, still mortified to be caught in such a compromising position.
She grabbed my computer, staring at what I was watching, which was a cheerleader getting triple teamed. “Oh, does my little brother have a woody for my cheerleader teammates?”
I stammered, “P-p-please leave.”
“Who is it? Kara? Sophia? Emily? Caroline?” She listed off.
The truth it was none of those, but rather Janice, although truth be told I had stroked off to every one of them at some point.
I suppose being the least athletic guy there is, and with absolutely no chance to ever score a cheerleader, I would tragically be in love with all of them.
Although they were all stuck up, pretentious bitches, except for Janice, I crushed after all of them. You always want what you can’t have….
“Leave,” I pleaded.
“Or was it your big sister?” she questioned, as she put the computer on the edge of the bed, suddenly shifting to an oddly sexy pout.
I was speechless.
I remained speechless as she moved right next to me and asked, “Does my baby brother fantasize about his big sister when he jerks off?”
“N-n-no,” I stammered, which was true, yet my awkward reaction made it look like I do.
“I think you do,” she purred, moving her hand to her skirt and pulling it up to show me her red panty-clad crotch. “Want to see big sister’s pussy?”
In a couple of seconds, my legs stiffened and my cum rocketed out, as I groaned, “Oh, fuck.”
“You really are pathetic,” she laughed.
“Get out,” I demanded.
“Gladly, perv,” she laughed, sauntering out.
As I lay in my own cum, humiliated in ways I had never imagined, I couldn’t get Samantha’s pussy lips, which I could see clearly through her thin panties, out of my head.
I cleaned myself up and went to bed hating my sister even more than I usually did, mortified by the humiliation I had experienced.
Next afternoon, I was playing Clash of Clans on my iPad while simultaneously watching Dr. Who when princess bitch staggered awake.
I cringed at what she may say. But to my surprise she asked, not mentioning last night at all, “Can you fix my phone?”
“What happened to it?” I asked, looking at her. Other than hungover, she didn’t look smug or anything, maybe forgetting about last night in her drunken stupor.
“I don’t remember,” she said, “I don’t even remember how I got home.”
“You don’t remember anything else when you got home?” I asked.
“No,” she said, “I really need to stop drinking gin.”
“That’s good advice,” I nodded, a huge relief she didn’t remember last night at all. “I’ll take a look at it,” I said, taking her phone, “but I’ll need your password.”
“Brad,” she answered.
“Very creative,” I quipped, Brad being her boyfriend’s name.
“Thanks,” she said, oblivious to my sarcasm, before heading into the kitchen for breakfast…at lunchtime.
I took her phone upstairs to my room, plugged it into my computer to see if it was simply dead.
I had to play with it for a bit, but long story short, it had simply frozen.
Curious, and thinking I likely had time, I decided to snoop. I quickly downloaded all her photos, hoping to find some sexy shots of her many hot friends.
As I did, I decided to read her most recent texts, for amusement. But, what I read shocked me to the core.
Her last few texts were after she caught me in the act and were to Sophia and were about me… my dick precisely.
I began reading from when it began to be about me.
Samantha: You won’t believe what just happened!!!
Sophie: What? Did Brad ‘accidentally’ fuck your ass again?
‘Wow, sis takes it up the ass,’ I thought to myself, my cock getting stiff immediately.
Samantha: No, LOL. Plus, truth be told, I kind of liked it.
Samantha: Says the slut who got a bukkake last weekend.
Sophie: Hey, cum is supposedly good for avoiding zits.
The idea of Sophie’s face coated with cum was incredibly hot.
Samantha: Then you should have a perfect complexion.
Sophie: And I do! So what is the big news then?
Samantha: I walked in on Eddie stroking to cheerleader porn.
Sophie: That is not a surprise.
Samantha: His dick is like 9 inches.
Sophie: fuck off
Samantha: I’m serious, if he wasn’t my brother I would have straddled that big dick and gone for a ride.
I couldn’t believe what I was reading… my sister was talking about fucking me.
Sophie: 9 inches, that seems almost too big
Samantha: only one way to find out, LOL
Sophie: that’s true. I may have to bang your brother.
Sophie: ass whore
Samantha: cum bucket
Sophie: shit, now I need a cock
Samantha: me too
Sophie: you have one in the room right beside you LOL
Samantha: you’re sick
Sophie: u know it
Samantha: oh crap, I should never have gin….I got to go.
Thus ended the surreal, cock hardening, text conversation.
After having her flash her pussy at me, and now this, I began to think of my sister in a very non-sisterly sort of way.
I quickly downloaded all her text messages and then took her phone back to her.
I said, as she finished eating some toast, “All fixed.”
“Thanks,” she replied, not looking up and not asking what was wrong. She was just used to having things taken care of when they went astray…oh the life of the beautiful.
I shook my head at her, but, of course, she was oblivious to my contempt of her.
I returned to my room to snoop through her pictures.
The majority were selfies, another reminder of how vain she is, although some included some of her other hot friends.
There were some of her and her fellow cheerleaders at a recent competition and then some from the hotel that night with them in even less clothing that got me incredibly erect again.
Then I noticed a file called homework. I immediately got suspicious, she would never have such a file… she didn’t do homework.
I clicked on the file and almost instantly came in my pants. There were over a 100 photos of my sister and a couple of her cheerleading friends naked and in some very compromising positions.
I took my time going through each photo. The first few were each cheerleader topless where I analyzed each girl’s breasts individually.
It was amazing how different each girl’s breasts were.
Kara’s were incredibly large, which isn’t surprising as she is the only chunky girl on the team, with big areola and yet oddly small, although erect nipples. Being the only black girl on the team, her black skin seemed rather exotic to me. I wanted to cup those big jugs with my hands, curious how heavy they would be.
Janice, on the other hand, the one cheerleader who was remotely nice, had small firm tits. Her nipples were huge and stiff and seemed to call out for attention. Although Kara was smiling and posing sexily for her picture, Janice seemed nervous and uncomfortable.
Sophia had really small tits, yet with a large areola region that showcased her small nipples and I wondered, being the geek that I was, the actual weight of her breasts in comparison to Kara’s massive ones.
And then I saw my sister’s breasts.
And then I stared at my sister’s breasts.
And then I drooled over my sister’s breasts.
They were perfect.
Not too big.
Not too small.
They were a perfect handful.
Being the geek I am, I had researched online the perfect breasts and hers fit the concept completely. The whole 45% breast tissue above the nipple line and 55% below… the perfect natural shape… something implants can never do.
Her nipples seemed to be ripe berries ready to be plucked with a perfect circular areola to showcase it.
My cock was dying for attention. Recalling last night, I moved to lock my door… I wasn’t going to have a rerun of last night’s ‘caught in the act’.
Returning to my laptop, I slowly flipped through a few more breast pics of the four of them cupping them playfully before things got even more interesting.
There were pictures of Janice sucking each of the other three’s nipples. Each one its own piece of art.
Janice’s pure white skin against Kara’s chocolate black skin was a jarring contrast. A beautiful contrast of black against white. I flipped through a few more pictures of Janice pleasuring Kara’s breasts and noticed that Janice’s face didn’t show the same embarrassment as she did when she was getting photographed with her breasts… no, her eyes were glazed over as if she was in utter awe of the beauty of the black breasts she was pleasing.
There were a couple of pictures of Janice kissing Sophia’s small breasts, the smug smile on Sophia’s face and her hands on the back of Janice’s head. In each of these, Janice had her eyes closed… which made her look so cute and vulnerable.
Then Janice was cupping my sister’s perfect tits. Seemingly looking at them in the same awestruck way that I had a few pictures earlier. Her eyes were big as she extended her tongue to my sister’s stiff nipple. A couple more pictures of Janice pleasuring my sister’s tits had my cock ready to burst.
I fished out my dick to liberate it from my tight jeans.
Yet, I didn’t stroke it as I continued to flip through more pictures.
The next ones were of each girl’s pussy. The first was Janice’s. Her look of insecurity returned as she spread her legs and looked down, not making eye contact with the camera.
Yet, Janice’s pussy was beautiful. I had stared at lots of internet pictures of pussies, but somehow it was like I was seeing one for the first time. I stared at it like it was an art exhibit. She had a light bush of red hair, apparently she was a natural redhead, which seemed to give shade to her long, asymmetrical pussy lips that stuck out just past her labia. Her clit was hidden by her hood begging to be pleased… for someone to open it up and find her clit.
Unfortunately, there was only one pussy picture of Janice before I saw one of Kara. Her pink pussy, such a contrast with her dark skin, was like a gift from God… a beauty only HE could create. She had no hair on her pussy, but a small triangle above her hooded clit. Her puffy pussy lips looked already stimulated and a slight gleam showed on them. Two more pictures of her cunt, with her fingers spreading her pussy open wide, drew me in. I imagined burying my face in her pink inviting opening.
I wanted to stroke my cock, but continued to refuse as I wanted to see all the pictures.
Next were half a dozen pictures of Sophia’s pussy, which I flipped through rather quickly, partly because I found it less appealing for some reason (she was very hairy, which hid her pussy and her labia was quite plump which seemed out of place in her tiny body), and because, truthfully, I wanted to see my sister’s cunt.
Can a pussy be perfect?
Maybe it was her tits, which were still firmly in view.
Maybe it was her confident smile. Her long blonde hair or blue eyes, all put together to create the perfect package.
Either way, her completely shaved cunt, not a hair anywhere, stared at me as if beckoning me in… as if saying, ‘This is what you can never have’. Her cunt was lush. Her clit was exposed, but not prominently, as if playing peek-a-boo. Her outer lips were pretty plump, as if she was already excited, and I imagined, forgetting she was my sister, burying my cock in her tempting perfection.
I was now slowly stroking my cock, knowing there was no way I was going to last through all the pictures when there was a crash at my door.
“Fuck, Eddie, why the hell would you lock the door,” Samantha cursed.
I quickly put my cock away, closed my laptop as I said, “To get some privacy.”
“Open up,” she demanded.
I was curious what she wanted as there would be no way for her to know that I had downloaded her photos.
I opened the door and asked annoyed, “What?”
“What were you doing?” she asked, in her usual condescending tone.
“Writing my memoirs,” I sarcastically quipped.
“Whatever,” she said, waving her hand to make it clear she didn’t really care. She then asked, “Did I come in here last night?”
“No,” I lied.
“You sure?” she asked, as she had obviously read the texts she wrote last night.
“Yes,” I said, “Unless you came in here after I was asleep. I wasn’t feeling great last night and was in bed before midnight.”
“Oh, okay,” she said, looking both confused and relieved.
“Why?” I asked, deciding to have some fun with this.
“Oh, nothing,” she shrugged.
“Okay,” I shrugged back. “Is there anything else?”
She looked down at my crotch area ever so quickly, not something I would usually notice if I didn’t know what I already knew, before turning around and walking away.
I shook my head, closed my door, locked it and smiled… an idea suddenly popping into my head.
I could blackmail my sister to make her be nicer to me, maybe do my chores, maybe set me up with Janice… the only cheerleader who may go out with me… the rest all being bitches.
I returned to the photos curious what else they took pictures of, realizing what I had seen so far was just the tip of the iceberg.
The next dozen pictures were all of Janice again with her head buried between each of the three girl’s legs. The pictures didn’t get close enough to see any of the girl’s cunts or Janice’s tongue. I imagined she was licking away. Some were close-ups of Janice’s head between their legs (the couple shots of Janice between Kara’s again looking incredibly cool). Some showed the girl’s lips pursed or moaning, only confirming my original deduction Janice was lapping away.
I read enough lesbian stories to know Janice was either blackmailed or was submissive… or likely a mixture of both.
There was then a close-up picture of Janice’s face glistening with wetness. I wondered had she gotten all three off. I wondered if this was the first time this happened. I wondered if Janice was a lesbian.
I fished my still stiff cock out of my pants again and continued going through pictures.
The next one was of my sister with a strap-on cock. She was holding her cock with one hand while her other hand was on her hip posing.
I was curious who she planned to use it on.
The next picture had all three girls on the floor, on all fours with their asses up. Kara was in the middle of the two white girls. The contrast was amazing both in black vs white and big butt vs not. Kara’s ass was wide and looked like something you could grab onto and really go to town with… as if her body was made for pleasure. Sophia, on the other hand, whom I always thought was skinny, looked like you could break her if you fucked her too hard… I realized immediately that I’d rather fuck her face than her cunt. Lastly, Janice. Not too big or small, not fat or skinny, was enticing… an example of what simple beauty is, not the fake generic anorexic look showcased by today’s models.
I pondered whom I would fuck if given the chance. Oh, I would definitely date Janice if the option was there, but in regards to fucking and losing my virginity… well that wasn’t as black and white (pun intended). I stared at their asses like I was at the Louvre trying to decide which my favourite was: the La Grande Odalisque painting or the Sleeping Hermaphrodites sculpture; as well as my biggest disappointment, the Akhenaten which didn’t live up to my expectations. (yes, I went to France on my grade 11 travel tour). I couldn’t pick a favorite, each painting, each sculpture being so symbolic and distinct on its own, defining a time in history. I couldn’t choose between two completely different women, although I compared Sophia to the Akhenaten, a little disappointing when seen up close. Yet, Kara was the Sleeping Hermaphrodites (looking so enticing) and Janice the La Grande Odalisque (looking so innocent and yet sensuous) and I wanted to revel at and in both.
I flipped through a few more pictures which were poorly taken as my sister obviously took them as she moved behind and fucked each one. I wanted to see their faces, their eyes, their lips. I wanted to hear their moans and whimpers. Did they talk dirty? Did they beg for more? Did they moan or scream?
So many unanswered questions, pictures unfortunately not really able to speak a thousand words.
There was a picture of Janice with the strap-on in her mouth, taken by Sophia as Kara’s black feet were in the picture.
Again, Janice’s look was one of reluctant submission, like she was forced to do this, or she couldn’t stand up for herself.
It made me wonder.
Janice wasn’t a cheerleader in her freshman, sophomore or junior years, actually being in debate club and the world UN. Yet, in her senior year she came back dressing sexier in short skirts or dresses, wearing make-up and hanging out with the cheerleaders. She also quit the so-called nerd clubs… clubs I was in.
It made me wonder what led to the transformation.
This wasn’t a Disney channel movie starring a pre-slutty Miley Cyrus.
A couple more pictures of Janice sucking a plastic cock, one with it completely in her mouth, her eyes wide and what looked like a tear forming in her eye.
I couldn’t tell for sure. It sure didn’t seem like she was enjoying this.
The next few pictures only blurred the lines more as Janice was on a bed now with both Kara and Sophie. Her breasts were sucked, her pussy fingered. One even had Kara’s black finger in Janice’s ass. I was confident Janice was blackmailed or forced to be their sex-toy.
The next couple of pictures had Janice still on her back, Sophia straddling her face. That was followed by a picture of Kara straddling her face. I wondered if each were having multiple orgasms or if they put each other in compromising position after compromising position.
I realized there hadn’t been any pictures of Samantha for a while.
I flipped through a couple more of Kara cupping her tits as she seemingly got off on Janice’s face and tongue, before there was more of my sister.
This time she was on the edge of the bed, legs spread open, and pointing down to her shaved pussy. She looked so hot I slowly stroked my cock.
The next one had Kara kissing one of her feet, while Janice kissed the other.
The next one had Kara between her legs while Janice sucked on her tits.