BEST PRESENT EVER: Cheerleader Orgy by jasmine walker

Note: Although not necessary, reading part one (Best Present Ever: Bitch Sister) will explain how Mathew goes from being a nerdy virgin to a dominant Master over his gorgeous, stuck-up cheerleading sister.

Note 2: A special thanks goes to Estragon for his dedication to copy editing my work and making me a better writer.

BEST PRESENT EVER: Cheerleader Orgy

Christmas was pretty anti-climactic after the gift I gave myself…my bitch sister.

With so much of the family arriving and staying with us for Christmas it was impossible to get any alone time to continue my training of my slave sister. I did make it clear that she was suppose to find a way for us to be together on Boxing Day, preferably with her friends.

While we were unwrapping presents with the whole nuclear family in the evening, a family tradition that goes back over 100 years, Sandra whispered in my ear, “I got us a rendezvous for tomorrow afternoon, Master.”

Calling me Master, even quietly, in a room full of family was fucking hot and had my cock revved up and ready to go. I gave her a nod that showed my approval and continued my Christmas unwrapping, my mind already looking ahead to tomorrow’s presents. I wondered if she got any of her subs to agree; if so, who? I also wondered if Beth would be there as she was the one I really wanted to fuck.

The next couple of hours were chaos, and it was past ten before I got to ask my sister any questions. “So slut, what is tomorrow’s plan?”

She smiled, being coy, “Boxing Day shopping, of course.”

I warned, “Don’t make me punish you.”

Her smile stayed. “Maybe I want to be punished.”

“I’ll remember that,” I responded, a devious plan of role-reversal already in my head.

“Anyway, Allison is out of town, and so is her family, but I have keys to her house,” my naughty sister revealed.

“She is your lab partner, right?”

“Yes, you and she might really hit it off. She is applying to Harvard as well,” my sister answered, thoughtfully.

“Interesting,” I replied, acting uninterested, even though I was very curious. This bio partner was obviously smart, which was a turn-on in its own way. I was instantly curious what she looked like and how someone so supposedly intelligent could succumb to my sister. The only logical explanation was insecurity. Pushing the curiosity to the back of my mind, I asked, “And Beth?”

“I told Beth everything and she is quite eager to watch you and me go at it.”

“She does realize I plan to fuck her, right?”

“I imagine she knows it is a possibility,” my sister responded, giving my cock a squeeze, before adding with a pouty face, “You are not hard.”

I shrugged, “And Della?”

“She will be there too,” my sister revealed.

“Excellent!” I exclaimed, a naughty, naughty plan unfolding in my head. “And what time is this gathering taking place?”

“I suggested two. Della has a family supper at her grandmother’s, Beth has shopping plans with her Mother in the morning and I, of course, would like to do a little Boxing Day shopping myself,” she explained rather thoroughly, which I liked. She clearly didn’t want to upset me.

I suggested, “And I expect you to buy something special for tomorrow.”

She blushed, “You are so naughty, Mathew.”

I winked, gave her voluptuous breasts one quick squeeze and went to the kitchen.

BOXING DAY

I too went shopping in the morning, buying a new digital camera in HD, the Lord of the Rings extended version box set on Blu-Ray and a choker for my sister, which I planned for her to always wear as a constant reminder of who owns her.

Sandra texted me the address where we were to meet and I arrived, on purpose, a few minutes late. I knocked on the front door of the stranger’s house and was greeted by chubby Della in her cheerleader’s outfit and beige thigh highs completely in view with her short cheerleading skirt not able to cover any part of them. Her pink painted toenails, so clearly visible in her sandal-foot stockings, had my cock instantly interested. She greeted me, “Come on in, Master.”

Clearly she had been given instructions from Sandra. I followed her into the living-room where Beth and Sandra were already sitting down. Della immediately went to my sister’s feet and between her stockinged legs. All three sexy girls had on the exact same stockings and cheerleading outfits. I watched quietly as Della licked my sister’s pussy, my sister still trying to keep the image of power she had in her clique. But that was about to change.

I ordered, “Slut, get over here.”

Both Della and my sister turned towards me. I said to Della, “Not you Della. I am talking to the biggest slut here…my slave sister.”

“Mathew,” she whispered, suddenly ashamed by the treatment she was being given; ironic considering it is how she treated Della, and I assume her other pets.

“What, slut?” I asked, my tone implying I wasn’t in the mood for disobedience.

“Nothing,” she retracted, walking over to me.

“On your knees,” I ordered.

She obeyed, looking back at Beth nervously.

I smiled, “I bet Beth loves watching you being put in your place.”

Beth’s slight smile gave me the affirmative answer I was expecting.

I bent down and put the black choker around my sister’s neck. “This is to always be worn. It is a constant reminder of your place…as your brother’s personal fuck-toy slut. Is that understood?”

Her teary eyes showed hints of crying, but no tears flowed as she answered, “Yes, Master.”

“Now Della, let’s see those big tits,” I requested politely.

Showing no signs of nervousness, she quickly pulled her cheerleading uniform over her head, revealing a white bra and panties set. Her huge breasts were barely able to be held in check by the lace bra. I asked, “What size are your breasts, Della?”

“40DD,” she answered, just as she released them from captivity. Her breasts were completely captivating and mouth watering.

I walked over to her, leaving my sister on the floor, and said, “Do you like being a submissive to my sister?”

She broke eye contact with me and said, rather unconvincingly, “Yes.”

“Why do you obey her?” I asked.

Still refusing to make eye contact with me, she replied, “I don’t know.”

I chuckled, “You must know, Della. No one becomes a dyke slut without knowing why. So why?”

She whispered, “To be popular.”

“Ahhhhhh, the truth,” I proclaimed, pausing, “will set you free.”

I took one of her breasts in my hand and I felt her shiver, clearly uncomfortable with my touch. “Why are you letting me touch your breasts?”

“Because your sister told me to do whatever you asked,” the submissive girl admitted.

“So if asked you to bend over and take my cock in your ass, you would?”

“Yes,” she whispered, so quietly no one other than me could here.

“Would you enjoy it?” I asked.

“No,” she answered.

“Have you been fucked in the ass before, Della?”

“No.”

“But you would allow me to take your anal virginity, right here, right now?” I asked, attempting to make the submission as absurd as possible.

Della still had not made eye contact with me as she again confirmed her obedience with a slight nod.

I asked for confirmation, “And all this submission to my sister and Beth is simply to be popular?”

She shook her head yes and surprised me by looking up and defended herself. “You don’t understand. I have been treated badly based strictly on my weight.”

I interjected, “You are not fat, Della. You are chubby, or as Marilyn Monroe was described, voluptuous.”

She blushed, obviously flattered by a rare comment. “I used to be a lot larger,” she admitted.

I let go of her large breast and explained, “Della, I know exactly what it feels like to feel out of place. To be judged based on appearances. Actually, I assume you have judged me too. But I finally had enough of the judging and being treated like a doormat. Didn’t I, baby sister?”

My sister still on the floor answered, rather seductively, “Yeah, the mouse finally roared like a lion.”

I returned my gaze to Della and said, “Look at me, Della.”

She looked up into my eyes. Her blue-green misty eyes were beautiful. I attempted to build this insecure girl’s confidence, “Della, you are a beautiful woman with lots going for you, your eyes are enchanting, your smile is seductive and, of course, your breasts defy gravity.”

Clearly not used to flattery, she stammered, “T-t-thanks.”

“And I have a gift for you,” I said. I paused for dramatic effect before ordering, “Sandra, go take off your new Mistress’s panties.”

“What?” Sandra asked stunned by my order.

“I think my order was pretty clear. Get your whore ass over to Della,” I ordered. When she didn’t immediately obey I roared, “Now, slut!”

My sister gave the deadly glare that had crushed me so many times before. But I was no longer intimidated by her facade of power and I returned a glare just as menacing. A brief power struggle followed, but it was short lived as my sister began to stand up.

Making it clear that I was Master and she was the slave, I added to the humiliation, “Crawl.”

She fell back to her knees and crawled slowly. Her head down, avoiding eye contact, she obeyed my order, and eventually reached Della, who was unable to control her smile. Once my sister reached her chubby friend, I repeated my earlier command, “Baby sis, take off your new Mistress’s panties.”

My sister looked back at me her eyes pleading for a reprieve, one I refused to give. Sandra then slowly reached up and tentatively removed Della’s panties.

Once they were off, I spoke to Della, “Today, Sandra is your sub. Sandra beg Della for the privilege of being her dyke slut.”

Sandra was mortified by the turn of events, but looked up from her subservient position and asked, “Della, may I please be your sub?”

I scoffed, “That wasn’t believable, you can do much better than that.”

She sighed too, but upped the ante when she got nasty, “Della, may I please lick your pussy and pleasure you like you have me so many times?”

Della looked to me and then, her confidence building, just as mine had, she ordered, “Get licking, slave.”

Sandra had to reach up to reach Della’s pussy. The scene was oddly perverse and arousing. I glanced over to Beth, who was watching her best friend submit sexually to their joint sub.

The scene lasted a couple of minutes before Della, clearly uncomfortable standing, ordered, “Sandra, crawl to the couch.”

Sandra obeyed, her face slightly shiny from Della’s juice.

Della, beginning to get more comfortable with her new position of power, ordered, “Clean my soles with your tongue.”

Sandra’s look showed her unhappiness with the order and her new position, but she obeyed lifting Della’s right foot up to her face.

I looked at Beth, who was avidly watching the power shift, and walked over to her and said, “Are you enjoying the show, my sweetness?”

She looked up at me and asked demurely, “And why do you want to know?”

I was suddenly nervous. I know I could fuck Sandra or Della now, but it was Beth I craved. I attempted to be suave. “Because someone looks like she needs a late Christmas present.”

“I do, do I?” she answered, with a coy smile, her British accent adding to the playful seduction. Her hand went to my stiff cock, “Is this my gift here?”

“Yes,” I answered, “and it is a present that keeps on giving.”

“Really?” she teased, rubbing my cock. “Can I unwrap it?”

I nodded, a mixture of excitement and nervousness overwhelming me.”

She smiled and unzipped my pants and allowed them to drop to my knees. Grabbing my cock in her small hand, she teased, “What a big present! I’d better wrap it back up.”

She leaned forward and took my cock in her pretty little mouth, wrapping it back up. Watching my biggest stroke fantasy with her mouth full of my cock was amazing. Having not come yet today, I knew my first load would come quick. Her sweet mouth and the way she slobbered up my cock, creating a whirlwind of sensations also accelerated my quick release. Within less than two minutes, I shot my load down Beth’s throat. The great cocksucker that she was, she swallowed every drop and kept bobbing up and down.

Nearby, Della, getting into her new role of power, demanded, “Eat my pussy, captain,” her tone bitter and sarcastic. I glanced over in time to see my sister’s head disappear between Della’s slightly chubby legs.

Once my orgasm was completely done, I pushed her onto the couch and spread her legs. She was wearing pantyhose with a hole where her pussy was and no panties. I didn’t even know such things existed. I kissed her pantyhose clad thighs as she moaned softly. Nearby, I could hear Della’s increased breathing. I was tempted to bury my face between the British goddess’ legs but wanted to saviour this dream come true. I also wanted to get her excited enough to beg me to fuck her. I moved across her uncovered and slightly glistening pussy, my hot breath deliberately making my presence felt, but kept moving until I reached her other thigh. I kissed, nibbled and licked all over her leg, teasing her relentlessly. Her moans became a constant rhythm and increased the second shy sweet Della screamed, “I’m coming slut, keep licking me!”

Seconds later, Della’s undeniable orgasmic scream filled the room and spurred Beth on. “Enough of the fucking foreplay stud. I want that big cock of yours in me.” Having any girl say that to me was hot, but in Beth’s British accent it was even hotter.

I looked up and smiled, teasing her the way she used to tease me when I was just Sandra’s nerdy older brother, “All in good time, my girl.”

Instead I moved to her glistening wet pussy and began licking. Slow at first, just barely making contact with her swollen pussy lips. She lifted her ass, up attempting to make contact, but I backed away. I wanted it clear I was in control here.

She whimpered, “Please, just shove that big cock of yours in me.”

Instead, I sucked her clit into my mouth in one sudden movement.

She screamed, “Oh God, yes!”

Just as sudden, I let it go and returned to a slow tease.

Della, nearby, ordered, “Go get your brother ready to fuck Beth.”

I continued my teasing pussy-pleasing without looking up.

My sister asked, her tone humble and obedient, “Master can you open your legs so I can crawl between?”

Without moving my head, I opened my legs and felt my sister crawl between them. It must have been an absurd scene. A broad smile crossed my face as I reflected how quickly things had changed between her and me. As I began to put more pressure on Beth’s delicious pussy lips, Della joined making my original twosome a foursome. Della concentrated her attention on Beth’s perky breasts while I teased and pleased her down below.

Her moaning increased to heavy panting and she begged desperately this time, “Please, Mathew, I need your cock in my cunt so fucking bad.”

Smiling at her desperation, I tested her resolve, “All you have to do to feel my big hard cock in you is beg Della to straddle your pretty face so I can watch you eat pussy.”

Beth, who I knew from conversations with Sandra, had allowed Della and a couple of others to please her, had never returned the favour, although Beth and my sister had made out at a party for their boyfriends once.

Beth looked at me with a look of frustrated desperation before giving in completely, “Della, can I please lick your pussy?”

Della glanced over at me with a smile, before straddling Beth’s pretty face.

I watched as Beth extended her tongue and tasted her first pussy. Keeping my word, I took my cock out of my sister’s sweet mouth and repositioned myself so I was ready to fuck my British dream girl. I tapped my cock on her clit, which triggered uncontrollable moans and twitches.

She whimpered between licks of Della’s pussy, “Please, Mathew, I need your cock in me so fucking bad.”

I finally obliged her wanton lust and made her begging and my fantasy come true at the same time. I pulled my cock out of my sister’s sweet lips and slid it between Beth’s pussy lips. The second I slipped between her glistening pussy lips I was in heaven. Her warmth numbed me as I slowly filled her pussy with my cock. Once all in, I began to slowly fuck her, taking my time as I wanted to savour every second inside her oasis of juice.

Her moans only enhanced the sensations I was feeling, knowing I was responsible for those moans of sexual pleasure. After a couple of minutes of slow and steady fucking, I ordered my sister, who was watching this perverted threesome, “Come suck on Beth’s clit while I fuck her, baby sis.”

Without hesitation, my sexy sister moved bedside her best friend and took Beth’s swollen clit in her mouth.

The double sensation had Beth writhing in pleasure as I shifted from slow steady thrusts to deep fast thrusts. The scene was porno movie hot and within a couple of minutes of the double pleasure Beth screamed bloody murder as an orgasm tore through her body. Both Sandra and I continued our focused pleasing all throughout Beth’s orgasm.

Once I thought she was done, I demanded, my confidence brimming, “Let’s reposition ourselves. On your knees on the floor, Beth. Della sit on the couch and offer our British slut your sweet cunt. Sandra crawl underneath Beth and suck on her sweet cunt.”

Very quickly, I watched as my directions were followed faithfully. Once the three were in position, I watched the lesbian threesome with manly satisfaction. A few minutes later, with both Beth and Della moaning louder, I moved behind Beth and slid my cock back into her pussy. Unlike my slow thrusts the first time, this time it was about getting me off. Each hard thrust forward had Beth’s face slammed into Della’s cunt.

I was just beginning to get in a proper rhythm when Beth begged, “My arse, fuck my arse, baby.”

It took a moment to figure out what she was begging for, for me to fuck her sweet ass. My dream come true just kept getting better and better. I slid my cock out and rubbed it between her ass cheeks. She begged again, “Don’t tease me baby, just fill my arse with your cock.”

Now desperate to do just that, I spread her ass cheeks apart, found her tiny rosebud and wondered how the hell my cock would fit inside such a small hole.

I placed it at her anal entrance and slowly pushed forward. It was so tight and that penetration seemed impossible. I paused with just the very tip of my cock inside her. Suddenly she pushed back and my cock slowly disappeared inside her ass. It was so tight I wasn’t convinced I would be able to fuck her. The decision was made for me when pretty British Beth began to fuck herself on my cock. She started slow as her tight ass got comfortable with my big cock. The tightness was the most incredible feeling ever and because she fucked me slowly it kept me revved up but not close to climax.

Beth’s moans increased again as she got accustomed to the cock in her ass and the pressure on her clit from her best friend. Time seemed to stand still as I experienced my first foursome. Once in a comfortable rhythm, Della pulled Beth back to her pussy. The naughty foursome continued for a long time before Della reached her second orgasm, soon followed by Beth having her second orgasm from me as she screamed, “Oh god yes, your cock feels so fucking good in my arse, baby. Yes, oh yes, oh yes, oh-oh-oh-oh fuuuuuuuck, I’m coming from your arse-fuuuuucking!”

Her body quaked around my cock and enhanced the sensation and I knew I would soon follow. I grabbed her ass and began to pound her hard even as her orgasm continued to thunder through her. Finally close, I pulled out of Beth’s ass and shoved my cock into my sister’s mouth. I fucked her face like it was a pussy and unloaded a full stream of cum in her mouth. Once spent, I fell back onto the couch to catch my breath. I snapped my fingers and my sister obediently crawled between my legs and cleaned my cock.

Beth beside me said, “That was fucking amazing.”

I smiled, “You were not bad yourself.”

She slapped me teasingly.

Della, surprising all three of us, said, “I hope you have enough left for me.”

I smiled, “Of course, Della, I definitely would love to titty-fuck you.”

Della smiling, moved between my legs and replaced my sister, taking my still hard cock in her mouth.

Beth, surprising me as well, demanded, “Sandra, get over here and lick my pussy like a good slut.”

Sandra looked surprised by Beth’s dominant attitude, but obeyed, crawling between Beth’s legs.

Beth and I looked at each other and smiled, secretly sharing a moment. We both allowed ourselves to be slowly teased and primed for more over the next fifteen minutes.

Della finally took my cock out of her mouth and straddled me on the couch. She easily swallowed my cock with her wet cunt and began to slowly ride me, her massive breasts directly in my face. My mouth watered and I took her right nipple in my mouth and sucked on it eagerly.

Beside me, Beth attempted to prove her newfound power over her best friend by demanding, “Lick my arsehole, Sandra.”

I glanced over and saw Sandra’s disgusted face, but as Beth assumed, Sandra did as she was told. I smiled at my sister’s utter collapse in her social hierarchy, before returning my focus to Della’s voluptuous tits.

Time seemed to stand still yet again, as Della slowly milked my cock and I milked her tits.

Beth moans increased, and I saw she was fingering herself while my sister rimmed her arse.

Della’s moans increased simultaneously as Beth’s did and she began riding me faster.

Both girls started moaning louder in unison and came together a minute later. Della was clearer a squirter. I felt her juice leak onto me as she continued riding my cock through her orgasm. Once her orgasm had subsided, I flipped her onto her back and slid my cock, wet from her juices, between her luscious breasts. She squeezed her tits together and I fucked her melons. It wasn’t as amazing as a pussy or an ass, but the obscene act was enough to get my balls boiling. Della, who had said very little to me all day, suddenly talked dirty. “Shoot your cum on my tits, Mathew. I want to feel your hot cum between my tits.”

I granted her request a few seconds later as my third orgasm shot out of me. My cum covered her tits as I finished pumping all over her voluptuous breasts. Once done, I watched as Della scooped up my cum and bathed her breasts with my cum. It was fucking hot.

The four of us exhausted, having all had multiple orgasms, except for my sister who had yet to reach orgasmic bliss, sat on the couch speechless.

Sandra broke the silence begging, “Master I need to cum.”

I got up, went to the kitchen and returned with a long, thick cucumber. I handed it to her, “Have at it, slut.”

Realizing that was her only option to having her long withheld orgasm, she opened her legs and began fucking herself with the cucumber. She closed her eyes and pumped her cunt furiously. Suddenly Della leaned forward and sucked on Sandra’s left breast. Beth too joined in, leaning down and licking my sister’s swollen clit. The triple sensation was the final push that broke her dam and she reached orgasm with a tidal wave of juice. Her scream echoed through the room, as she frantically fucked herself through a much-needed orgasm.

I watched the act in voyeuristic glee as I started to get dressed.

All three girls collapsed again on the couch and all three looked up at me as if awaiting their next orders.

I looked away to the pictures on the wall. An eight-by-ten on the wall, of a cute, nerdy, brunette stared at me hypnotically. She was so cute. I asked Sandra, “Is that your science partner?”

Sandra nodded, “Yes, that is Allison. She is a female you.”

“How so?” I asked, curiously.

“Well, until this week anyways when you changed. She is a genius, incredibly timid, easy to manipulate and a very quick learner,” Sandra explained. “I even offered her a tour of your college that you would give her sometime…she wants to major in psychology too.”

“I see,” I replied distantly, my mind already pondering my next move. “And she is your sub too?”

“Yes,” Sandra asked, adding, “but not in the same way as Della or Mrs. Raske. She was just looking for somebody to show interest in her and to treat her like a sexual being and not just a brain. She was easy to seduce, but both times we’ve been together she has eagerly obeyed my orders.”

“Hmmmm,” I mindlessly responded, pondering how Allison and I could work. I asked, “When does she return?”

“On the 30th, I believe,” my sister informed me.

“I want to meet her,” I announced.

“That could be arranged,” my sister smiled, but added, “she is not a slut like Beth, Della and me though. Plus, she is a virgin.”

“I don’t want her to know about your submission to me, is that understood?”

“Of course,” Sandra replied.

“Good,” I finished, “I am out of here. You three feel free to play as you wish.”

I was just leaving when my sister informed me, “There is a New Year’s Party next door on the 31st and I definitely think you should come with us.”

“Who is hosting it?” I asked.

“Tyson,” my sister answered, but added, “Mrs. Raske will be chaperoning.”

I smiled. “Excellent.” I winked to all three and left them alone hearing Della demand, “You two, massage my feet.” I turned back to see both popular perfect bodied cheerleaders fall on the floor and to the feet of their former sub.

I closed the door smiling…many more devious ideas spinning in my head.

The End…for now….