tagIllustratedA Sister Surprise: Cute Cheerleader

A Sister Surprise: Cute Cheerleader


Summary: Sister & brother have 3some with head cheerleader.

Note 1: Thanks to Tex Beethoven, Robert, and David for editing this chapter.

Note 2: All characters are at least 18-years-old.


This is the third chapter of the story of Joey (who'd been a virgin before attending last night's Halloween party with his sister), and of Sarah (his older college sister who primarily lives at a sorority over an hour away).

In part 1, Joey is convinced to go to a party dressed as the Joker to be his hot sister's anonymous date for the evening. Joey has had a crush on his sister forever and once Sarah realizes how well-endowed her brother is, the cat and mouse game of will they or won't they begins. Spoiler alert: yes, they did.

In part 2, A Kinky Afternoon, Sarah rocks Joey's world the next morning with the best wake-up call in the world... a blow job from his sister. Joey is thrilled to learn that as far as his sister is concerned, last night's sexual explorations are worth continuing, and the day then unfolds with marathon sex between the siblings, including Joey taking the last of his sister's three holes while she's dressed as a cheerleader (Part 2 was illustrated).

The story now continues immediately after a quickie fuck that had Joey deposit his fourth load of the day... (first down his sister's throat, second in her cunt, third all over her face and the most recent on her glistening pussy lips). Joey dresses as Batman and Sarah as a naughty school girl (see chapter 2), and they plan to head to a Halloween party on Saturday October 29th which is hosted by Jane, the current head cheerleader of Joey's high school. Since last year Sarah had been head cheerleader at the same school, she has high status in a secret cheerleader society that has been going on for decades, and one of the perks of this status is that Jane is a submissive to her.

I put on the Batman costume Sarah had bought for me, but the pants were so big that they wouldn't remotely stay up on me. The shirt also was way too big, so I looked and saw it was size XL. I laughed, as I was barely a medium in most outfits.

Luckily, I had a cool medieval costume from a comic con last year and I figured other than a couple of my nerdy friends, no one had ever seen me wearing it. I headed out and saw my sister had also changed. She was now in a Wonder Woman outfit with the tightest t-shirt in world history proudly displaying every curve of her huge tits... including her perky hard nipples. She was also wearing the shortest leather skirt I had ever seen, and sexy red boots... with red thigh highs. The skirt was so short that unless she was standing very straight and still, I could even see her naked cunt. I couldn't imagine her wearing that in public.

As I drooled over her outfit, she asked, "You changed?"

"You too," I countered.

"You got some cum on my blouse," she pointed out.

"You bought me an extra-large outfit," I pointed out.

"Well, you can be my knight in shining armour anytime," she smiled, walking over to me.

"And you can be my damsel in distress," I playfully bantered back, reaching under her skirt and rescuing her honey pot from loneliness.

In the car on the drive to Jane's party, I said, "Thanks for this."

"Thanks for what?" Sarah asked.

"For the past twenty-four hours," I replied. "I still want to pinch myself: I can't believe it really happened."

She leaned over and pinched me.

"Ouch!" I said.

"Think of this as your own Disney fairy tale, except instead of a newly-discovered princess, it's about a big dicked prince being presented at court," she suggested.

"So Cinder-fucka?" I joked.

"Or Beauties and the Beast," she smiled, reaching over and squeezing my cock... which for once was actually flaccid. "Oh, that's a surprise... it can be soft."

"On occasion," I admitted.

"Well that is so disappointing," she dramatically sighed.

"I will always be ready and willing when you need cock or cum," I promised.

"Don't you mean cock and cum?" she corrected.

"Well, that goes without saying," I agreed, before singing, "You can't have one without the other."

"You're still a geek," she laughed.

"A big dicked geek," I corrected.

"Yes, a very big dicked geek," she concurred, rubbing my cock with her right hand, driving with the other.

"So what is the plan exactly?" I asked, knowing only that she planned to somehow set me up with the hottest cheerleader in my school: Jane.

"We're planning to get you a girlfriend named Jane and to get you laid," she answered, "are you up for it?" giving my cock another playful squeeze, stirring it back to life.

"Does the cheerleader secret society give you the ability to order cheerleaders to fuck guys?" I asked, trying to fathom how the society worked and how she possibly could think that a cheerleader who had always looked right through me was going to fuck me tonight.

She laughed, "No, I can only insist that she munch on me. But once she sees that dragon-slayer of yours, she'll be all over you."

"I can't imagine it being that easy," I said.

"Girls love a big cock," Sarah revealed. "And one like yours is almost impossible to resist."

"I should Instagram my cock then," I joked.

"You joke," she said, still slowly rubbing my cock, as if unable to keep her hands off it. "But if you actually did, you'd be bombarded by women who wanted it inside them. They'd send you back lots of pictures of their own."

"So size matters," I said.

"And how you use it," she added.

"Well then, I guess I need more practice," I declared, wanting to fuck my sister every chance I could get.

"Well, you're always welcome to practice on your big sister," she smiled, trying awkwardly to get my cock out of my costume without steering us off the road.

"You should focus on driving," I pointed out, when she swerved into oncoming traffic, prompting some squealing tires and angry horns.

"Fine," she sighed. "I should probably save some cum for Jane."

"Trust me, I have more than one load in this barrel," I promised, knowing I had a few more loads in me if needed.

"Well, I imagine there will be some double barrel shooting," she said, as she gave my cock one more squeeze before she pulled into a driveway that led to a massive house.

"She lives here?" I asked.

"Daddy is a senator," Sarah explained.

"I see," I nodded, her house four times the size of ours... and we were not poor.

"Ready to become legendary?" she asked.

"I'm ready for anything," I answered.

"Hmmmmmm," she purred, "that is the right answer. Get that seatbelt undone."

"Yes, ma'am," I joked, as I quickly did, hoping for a blow job.

"Ass up."

I did.

She tugged down the thin fabric holding my cock in and took my rod in her mouth, bobbing furiously for a couple of dozen strokes. She then added, "Remember, I always get first right of refusal."

"This is always available for you," I moaned, "lifetime guarantee," as she sat back up... just teasing me.

"Let's go," she said.

"It looks busy in there," I said.

"Halloween parties run by cheerleaders are always the stuff legends are built on," she said, getting out of the car.

"I always imagined," I nodded, as I got out too and followed her towards the front door.

She said, "Once we're inside I'm going to go and find Jane, so you go and have some fun."

My eyes went big under my mask. I had no idea how to have fun at such a party. These people were the crème de la crème of high school society! I suddenly found myself begging, "Please don't leave me alone."

Sarah smiled, "Look Joey, I owe you for being my last minute escort last night and I plan to repay you big time."

"I think I'm the one repaying you," I quipped back, before adding and stressing the words, "big time."

"That is the confidence you need," she nodded, stopping in front of the big front door. "Look Joey, high school is all about appearances. It's based strictly on looks, wealth and confidence. Or more precisely, the appearance of looks, wealth and confidence. So play the part. Treat the girls there with the same confidence you've shown since you fucked the hell out of me and my sorority sisters. Girls don't want to be put on a pedestal, they want to be seen as more than just beauty and money; they want to be sexual beings. They like guys who know what they want and go for it. They want to be seen as both beautiful, AND a slut. Does that make sense?"

"Only in porn movies," I said, trying to imagine Jane as both sweet and sexy.... And slutty. I'd always placed her on a pedestal, and my imagination decided that was a perfect place for me to look up her skirt. My imagination also told me she wasn't wearing panties and gave me a good long look.

"Trust me," Sarah continued, "every girl has an inner slut dying to get out... they just need the right man and the right cock." She then again grabbed my cock and purred, "And trust me, you do have the right cock."

Still nervous, I suggested, "Why don't we go back home and you can have my cock all night?"

She suddenly turned stern. "Enough, Joey. You are a good guy. You are a decent looking guy. You have a big cock. And you can be dominant. Use all your personality and just become the full package."

I joked, "My package is pretty full right now."

"Shit," she said, sighing. "Now, I want that cock. She looked around, grabbed my hand and decided, "Let's build you some more confidence."

I followed her to some trees as she continued, "Don't you understand just how special you are?"

"No," I admitted, still in awe of my sister's lust for me.

"Your cock is utterly irresistible," she admitted, bending down. "I can't stop thinking about it. I can't stop craving it."

I listened to her words in awe, as I watched her take my cock in her mouth. God, her mouth felt so good! And she was right. If I could fuck my gorgeous sister, and treat her like a slut... the woman I most put on a pedestal... I should be able to do the same to Jane or any other cheerleader slut who had ignored me for over three years.

I groaned, taking control, "That's it, you cock hungry slut, suck on your brother's big, fat, cock."

She moaned on my cock in response, showing me she liked my dirty talk, the humming vibrations sending more pleasure through me.

"Hands behind your back," I ordered firmly, in awe of how quickly she obeyed me.

I then put my hand on the back of her head and pulled her down on my long dick. I had imagined this only worked in porn, but here was my hot sister obeying me and sucking me like a pro.

"You like being my sister slut, Sarah?" I questioned. After a couple of minutes of an amazing blow job, I moved my hand away and pulled my cock out of her mouth, deciding to take complete control like she suggested... testing her own theory on her.

She looked up at me with lust, "God, yes, baby, I'll do anything for my little brother's big cock."

Fuck, the look of lust in her eyes was hot!

Fuck, her nasty words and declaration were hot!

Yet, deciding I wanted complete control, I ordered, "Go to the tree over there and bend over."

"You want to fuck me, baby brother?" she asked, standing up immediately and striding away to obey my order.

"I'm not just going to fuck you," I responded, "I'm going to slay that peach in half."

"Oh yes, split me in half with your massive sword," she purred, playing along.

I again noticed she wasn't wearing any panties, as I lifted up her skirt. "I see your maidenhood is flagrantly unprotected against dragons."

"Claim it with your lance, my knight," she said, looking back at me.

And I slid my hard cock in her. "Oh yes," she moaned, as I buried my cock in her wet pussy. "Fuck me with your big cock."

I planned to fuck her until I deposited another load in her, but after a couple dozen strokes, a wicked idea popped into my head.

Abruptly I pulled out and said, "We should get to the party."

"You're stopping?" asked my sister, suddenly shocked and frustrated.

"Always leave them wanting more," I shrugged, loudly slapping her ass.

"Asshole," she retorted, still bent over and expecting me to slide back into her.

"Maybe later," I quipped back, enjoying having such power... impressed by my own restraint. I grabbed her shoulder, spun her around and kissed her hard.

She was surprised, but kissed me back.

Breaking the kiss, I smiled, "I think I've found my confidence."

"Fuck yeah, you have," she said, impressed, her cheeks flushed. "But I can't believe you quit."

"I'll make it worth the wait," I promised, as we headed back out of the covered area and towards the party.

"You fucking better," she said annoyed, "I fucking have pussy juice leaking down my leg."

"That's less obvious than a load of cum." I countered.

"Says you," she said, shaking her head.

As we reached the door, she recovered her moxie and asked, "Ready, stud?"

"As I'll ever be," I nodded, thinking it was now or never... my confidence was at an all-time high.

She opened the door and we walked inside... the house full of people... some I recognized, some I didn't. We weren't even there two minutes before I saw Jane. She was dressed as an airline stewardess... not as slutty as most outfits I was seeing.... but damn sexy... and she instantly had my temperature rising... my already hard cock throbbing. It also helped she was wearing thigh high stockings (green, of all colours), completely in view, and even after the wild day of sex with my hot kinky sister, I was already ready to be knighted as Sir Stud when I lanced the ultimate conquest: the head cheerleader.

No longer a virgin, my eyes opened wide to the reality that girls like sex as much as guys... and that my cock was bigger than most and would be a major benefit for me... I was ready to slay the metaphorical dragon that had kept me at the bottom of the hierarchy... I had been a peasant... I was now a knight... soon I planned to be the king.

Jane walked over to Sarah and smiled warmly, "I'm so glad you could make it."

"It's good to be back," Sarah nodded, as Jane looked at me.

It took her a moment, but she recognized me. "Is that you, Joey?"

My first thought was 'she knows my name?', but I didn't say that. Instead, I smiled, trying to remain confident, even as I was nervous as hell inside, "You look amazing, Jane."

"You look very different," she said, as she looked at me... not through me... but at me... as if seeing me for the first time.

"No glasses," I explained... somewhat blind without them, but they sure didn't go with the outfit.

"Maybe that's it," Jane nodded, as she then took an undeniable look at my crotch.

"Drinks?" Sarah asked.

Jane was pulled out of a brief daze (had Sarah told her how big I was, or was my outfit tight enough to showcase the hard-on I was sporting?). "Um, yeah, this way."

Sarah and I followed Jane through the throng of teenagers, each guy staring at Sarah with the jaw-dropped-to-the-floor look she always gets (the skin-tight Wonder Woman outfit making her even more of a magnet to horny boys).

In the kitchen Jane asked, "What's your poison?"

Sarah said, "Gin."

"You trying to get drunk and silly?" Jane smiled.

"Drunk and wild," Sarah countered, giving Jane a wicked smile.

And for the next hour, we drank... me for the first time other than a couple sips of beer. I chatted with people I'd never ever talked to before: football players, cheerleaders, the cool kids.

No one treated me like the nerd I always felt like at school.

A few girls even seemed to be checking me out... the new me a lot more confident, funny and charming.

Jane surprised me by appearing out of nowhere, grabbing my hand and saying, "Come with me, stud."

Sarah, to my surprise, saw us leaving and followed, as we went past a few rooms (I wondered how many bedrooms this house had), before going into the last room down the long hallway.

The room was huge. It actually had two floors, as it had a loft at the back of the house. I gasped, "Who lives in here?"

"My parents, when they're home," Jane said, as she went over to a table and grabbed the remote.

Sarah asked, "Are the cameras filming?"

"Of course," Jane nodded, as she turned the television on.

"Action already?" Sarah asked.

"Likely," Jane nodded, as suddenly I was watching two jocks I couldn't name but recognized, double penetrating Shelly (our school President).

I gasped, even though I knew the answer to my question, "Is that Shelly Hamilton?"

Jane laughed, as she moved to me and put her hand directly on my crotch, "Me, I'm more a one juicy cunt or one big cock type of girl."

"Well, good news," Sarah said, as my eyes went wide at the reality that Jane's hand was actually, really truly, on my cock, "there is one very wet, juicy cunt in this room for you and one big hard cock here too."

Jane agreed, "Shit, he really is as big as you said."

"I know," Sarah agreed, shocking me that my sister had told Jane about my cock... apparently revealing our incest. Sarah then added, "If he wasn't my brother I'd be all over it."

"I imagine," Jane nodded, as she tossed the remote to Sarah, who had just moved to the bed and dropped to her knees in front of me. "I need to see this up close and personal," Jane declared, as I watched in awe... awe being the three letter word that described perfectly the past twenty-four hours. I glanced over to the television and saw Shelly really riding the cock in her ass, before I turned my focus to the perfect Jane who had now taken my cock out and was stroking it.

"Wow!" Jane said, seeming to be in the same awe as I was. "This cock is perfect."

"I told you," Sarah agreed, as she spread her legs and began to slowly rub herself, as she switched to a different room in the house.

I was suddenly in visual overload.

Jane on her knees in front of me stroking my cock.

My sister slowly rubbing her perfect peach.

And now, on the screen, the goth Chelsey had her legs spread and the blonde angel Patty (literally) was between her legs licking away.

The shocks just kept coming....

"Isn't that your room?" Sarah asked.

"Yeah," Jane nodded, swirling her tongue around my cock head.

"Isn't that your co-captain Patty?" Sarah queried.

"Yeah, she's a natural submissive and a complete lesbian," Jane said, before she leaned forward and took my cock in her mouth.

I moaned.

Sarah asked, "Is this all you imagined, baby brother?" Sarah asked.

"Oh God, I can't believe it," I said. Jane, my high school fantasy girl, was living up to her title of 'head cheerleader' by sucking my cock, while the most beautiful girl I knew, my sister, was watching avidly while she played with herself.

Jane took my cock out of her mouth just long enough to add, "I can't believe it either," referring to my big cock.

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