A Privileged Life

"Yeah? And just what did she tell you was wrong."

"Billy... do you promise me you will listen to everything I have to say before you blow up and start acting like a crazy person?"

"Yeah... yeah, I promise!"

"Okay, don't kill the messenger."

"Alright, I won't kill the messenger. Now tell me what Cassie told you."

"Cassie told me she came to Homecoming tonight with the full intentions of getting her brains fucked out. She said she was not going home until that happens."

"Oh, and so you were going to help her with that little feat. You were going to fuck my little Sister's brains out. Am I right?"

"No! She didn't want to have sex with me, and I was just trying to keep her from hooking up with someone other than the person she genuinely does want to fuck."

"She told you who she wanted to fuck?"

"Dude... Cassie wants to fuck you!"

"No way! I'm her, Brother!"

"Yes, way! And I don't think she honestly cares that you are her Brother."

"Danny, you are so full of shit. What makes you think Cassie wants to have sex with me?"

"Well, for one thing, she asked me how big your cock is."

"Wait a minute, Danny. Are you telling me my little Sister really asked you how big my cock is?"

"Yep! That's exactly what I'm telling you."

"Why would she even think you would know how big my cock is?"

"I asked her the same thing, and she said that since we played sports together and share the same locker-room, we have probably seen each other's cock."

"That makes sense. So, what did you tell Cassie about my cock size?"

"I told her it was bigger than mine and that mine is considered a little bit above average."

"And what did she say when you told her that?"

"She asked me if I thought it would hurt when you put it in. So, I asked her when you put in where? And that is when she said, in her... in her pussy."

"Oh, my God! You better not be fucking with me, Danny. Where did you last see Cassie?"

"Duh... the same place you did. She was dancing with me until you charged over like a raging bull. Your guess is as good as mine where she is now."

"If you find her before I do, don't let her out of your sight."

Billy dashes away and enters the ballroom just as the band announces the last dance for the Homecoming evening. Cassie is standing at the edge of the dance floor, staring into space. Billy approaches her from the rear. He taps her on the shoulder and says in his best English accent, "May I have this dance, my fair lady?"

Cassie smiles nods her permission, and Billy leads her by the hand to the middle of the dance floor. He bows, and she curtsies. The band begins playing the traditional closing song, "Good Night Sweetheart." Billy pulls Cassie in close, and she buries her face in his chest. Neither says anything to the other. Billy can feel himself getting hard again. He tries to keep is away from his little sister. Cassie feels his hardness and grinds against it. Billy tries to pull away, but Cassie won't let him.

The band begins to pack their instruments. The students say their goodbyes to each other and depart for places known only to them and their dates. It's assumed that they all plan to follow a Homecoming tradition.

"I'm starving. Do you want to get something to eat before we head home, Cassie?"

"I don't want to go home right now. The night is still young, and I want to wind down first."

"Okay... We can go to someplace to eat and wind down while we eat something."

"Can we go up to the Penthouse Suite and wind down awhile, Billy?"

Billy's heart races. He realizes Danny wasn't jerking his chain when he said Cassie had her eye on him to hook up with. Billy's first impulse is to throw Cassie over his shoulder, Caveman style, and haul her up to the suite and fuck her brains out. His rational self-steps in and convinces him that is not what a big Brother should with his Little Sister. He is just before telling her no when he sees hopefulness and pleading in her eyes. He takes his sister by the hand and leads her to the elevators. Neither Billy nor Cassie say a word on the ride up.

~~~~~

Billy opens the door to their luxury hotel suite and allows Cassie to enter first. She quickly kicks her high heel shoes off and grumbles about how sore her feet are after dancing all night. Without thinking of the implications, Billy offers her a foot massage. He is surprised when Cassie turns suddenly and leaps into his arms. He is even more surprised when she locks her legs around his waist and her arms around his neck, planting hot kisses on his lips. Billy opens his mouth to say something and Cassie's tongue darts inside. By instinct, he sends his tongue into Cassie's mouth in return. After a minute, Cassie breaks the kiss and pulls back, she says. "Thank you for making this night so special for me, Big Brother."

It takes Billy an instant to recover from his little Sister's kisses. None of his girlfriends had ever kissed him that hot. Cassie hops down from his arms, turns her back to him, and asks him to unzip her gown. Billy's hands tremble as he impulsively obeys his little Sister's request. Her gown slides from her slender body and puddles at her feet. Billy is left staring at the backside of his practically nude little Sister. She only has on a pair of French cut powder blue panties.

Billy's mind involuntarily travels back to all the times he had wondered what his little Sister would look like naked. He even recalls all the times he had admonished himself for wanting to make raw lustful love to his innocent little Sister. He feels guilty for all the times he had masturbated while fantasizing about sliding his cock into his little Sister's wet pussy. He scolds himself for getting an erection while standing there, looking at his near-nude Sister. He doesn't know what to say or do next. His mind is searching for something to say that won't make him seem like a total fool.

"Where did you learn to kiss like that, Cassie?"

Cassie turns to face her big brother and says, "Some of my girlfriends taught me. We've been planning for our first time with a boy for over two years."

Billy is in awe as he gazes upon his Sister's beautiful young naked tits for the very first time. They are everything he dreamed they would be. "Are you telling me you are still a virgin, Cassie?"

"Does that make a difference to you, Billy?" Cassie looks like she is afraid Billy is going to back out.

"No! Not at all," Billy stammers. "I was just thinking; Maybe I should have you give kissing lessons to some of the other girls I date."

"Maybe you should," Cassie smiles. "They would probably enjoy it. I know I would, but we are not here to talk about your girlfriends."

"Oh, really? And just why are we here," Billy chuckles?

"You know damn well why we are here, Big Brother! Now get busy and make a sexually experienced woman out of me like the King of Homecoming is by tradition supposed to do."

Cassie turns toward the bedroom, leaving her Homecoming gown on the floor as she looks seductively back over her shoulder at her excited but nervous Brother. Cassie takes a step toward the king-size bed, but Billy wraps his arms around her waist and pulls her naked backside against his chest. Billy is still in shock and can't believe that he even agreed to go through with their Homecoming date, much less taking her to this luxury hotel suite. He can't believe that his beautiful little Sister really WANTS to have sex with him.

Billy presses his hard cock against his Sister's firm rear-end. She giggles and twerks her butt against his dick. Cassie's movement seems to excite Billy even more. He moves one hand from her waist up to her exposed left breast with the other hand drifting down her side, exploring her curves. He brushes his moist lips against the side of her neck as he holds her tight, still leaning his body firmly into hers. Billy keeps one hand wrapped around Cassie's waist as his tongue drags up the smooth surface of her neck to her waiting earlobe. He nibbles at her lobe before sucking it gently and then sliding his wet tongue deep into her ear.

Cassie is uttering sounds that are a cross between a high whimper and a low moan. She is becoming a bit nervous as she realizes that this is indeed going to happen, and her Brother's touch is making her flinch awkwardly. She can feel his hardness growing through his pants as he presses his bulge into her lower back. She makes an extra effort not to overreact to her Brother's hard cock, but her body is betraying her with her pale white skin now completely covered in goosebumps.

Billy rolls the nipple of his Sister's left breast between his thumb and index finger. Cassie again flinches but says nothing more. She stands up straight and tall with her body stiff and rigid. She wants this to happen but is beginning to have second thoughts. Besides the occasional gasp or yelp due to her Brother's touch, the only other sounds in the hotel room are the deep breathing and low rumbles of satisfaction from her Brother, her first-time lover.

Cassie feels another shiver run through her body, as Billy groans in her ear while slowly grinding his body against hers. He releases his hand from her left breast and then begins to let it descend downward over her exposed tummy, before coming back up with both hands and lightly brushing his palms over the hard nipples protruding from her fleshy orbs. His trembling fingers lightly trace the exposed part of her breasts, running along the edge of her areola.

Cassie again recoils at his touch as he opens his hands wide and gently squeezes both of her large mounds together. Billy kisses her neck. She can't explain why, but her body suddenly seems to be super sensitive. There is something about her Brother's touch that is sending gentle electrical shocks throughout her entire body. She spins around and throws her arms around his neck and kisses him back. If you can believe it possible, that kiss is even hotter than the other one.

Billy moves his head down to suck and kiss Cassie's hard nipples. She shivers with delight. That is something no one has ever done to her, and she intends to enjoy every second of it. Billy nibbles on one nipple and then moves to the other. Cassie digs her nails into his arm and shakes with her first orgasm ever created by something or someone other than her fingers. It shakes her to her core. Billy knows what is happening and is delighted; he could do it for her so quickly. Billy's fear of disappointing his little Sister immediately fades.

Billy strips off his shirt and places his bare chest against Cassie's naked back and continues to intensify his tender assault on his little Sister's sensitive breasts. He firmly rolls both her nipples between his thumb and forefingers while squeezing both of her magnificent mounds together. He then slides one hand down her side, brushing lightly against her bare skin, as the other hand drifts to the top of her panty line. Slowly his hand descends over the thin blue fabric, cupping her mound, sliding his middle finger up and over the material before reaching her swelling nub. He then presses down on her swollen clit and begins with a slow circular motion as her hips gently sway in response.

The sweet sounds of wetness are heard as he places open mouth kisses on the back of her neck and shoulders, sending another stampede of goosebump racing all over her body as she pushes her ass into his hardness. She intuitively reacts to his expert touch. She places her hand over his to show her approval as he continues to work her now engorged clit through the thin fabric. Billy lets his middle finger glide down further over the material covering her sopping wet entrance, before pushing the fabric into her folds as it strains in vain around his finger to hold off the invader now threatening to enter her. Cassie's body is reacting overwhelmingly to her feminine senses as they intensify. Billy feels her wetness through her panties.

Billy quickly strips off the rest of his clothes and then stands gawking at his Sister's beautiful virgin body. She is more beautiful than he could have ever imagined. Billy's cock is so hard it feels as though it will burst. His balls are beginning to throb. Cassie is looking at her Brother with so much love and lust in her eyes; it makes him worry he might disappoint her. Billy had often wondered what his little Sister would look like when sexually aroused. - Now he knows!

Cassie's pussy is dripping, but she hands Billy some lube to put on his large cock, and then she crawls to the middle of the king-size bed, offering herself to her big Brother. She had heard tales about how painful the first time can be and wants her first time to be as painless as possible. Billy put the lube aside because he fears a premature ejaculation just touching himself if he ladles any lubricant amount over his cock.

Billy nervously stands at the foot of the king-size bed, contemplating his next move. He takes a deep breath, reaches out his trembling hand, and grips it around one of his Sister's ankles. He pushes it forward slightly, bending her leg at the knee, as his other hand slowly slides its way up the inside of her other leg below the knee. He adds gently pressure to spread her legs, exposing her now wet sex that is entirely soaked through the fabric of her panties. Billy slides into the bed with Cassie and kisses her on her left knee. Billy's touch is deliberate but soft as he leans in and kisses the inside of each thigh.

Cassie shivers in delight as his lips widen, and his tongue drags its way up one of her spread legs. No boy has ever had his head between her legs. She is not sure if she wants this, and instinctively reaches her hands down to the top of his head as she lightly pushes back to stop his advances with little effect.

Before Billy reaches Cassie's wet pussy, he can see just how wet his little Sister surprisingly is. He smiles at the sight before switching to her other leg and once again kisses and licks her milky thigh as he pushes her legs farther apart. She feels his lips touching her sensitive skin as goosebumps run wild all over her body. Her Brother's wet lips then kiss their way up her thigh and arrives at the fabric's edge, covering her wet honey pot. Billy is only using his hot breath to penetrate her soaked panties. That creates a tickling sensation in her crotch that threatens yet another orgasm. Cassie reaches one of her hands down and again grabs the hair on the back of Billy's head in a fruitless attempt to fend him off, with her other hand covering her mouth as her breath begins to sound heavy and gentle squeals escape her quivering lips as she shakes in ecstasy.

"Mmmmm," Billy moans as he deeply inhales his Sister's womanly scent of arousal.

"I love the smell of an aroused feminine beauty such as yourself, Sis. Your lips have opened wide for me, begging for my tongue to taste you. Let's remove this covering so that I can do you justice."

Billy reaches his fingers up high on her hips as he drags the soaked blue panties down her legs and then over her feet, letting them fall to the floor, exposing her naked pink flesh.

"Oh my God, Billy," Cassie softly whispers.

Billy lifts his head slightly upwards as he gazes at his Sister's beautiful pink pussy pooling with her sweet nectar. He descends on her with open lips as they make a perfect seal on her flowering bud before dipping his thick tongue into her wetness.

"Oh my God, Billy," Cassie gasps out loud as her breasts heave forward, and her nipples harden once again. She feels her Brother's tongue exploring her insides as his mouth expertly presses into her wet lips as if they were having a passionate kiss.

The mixed sensations of his hot breath, the primal feeling of his tongue darting inside her, and the tingling from his tongue on Cassie's womanhood has her moaning uncontrollably. Tears stream down his Sister's face as he begins lapping up her juices. Billy continues to lick deep inside her vaginal walls while dragging his mouth all over her now wanton pussy lips. Her legs open, further inviting him to dine on her wetness as her beautiful flowering lips naturally opened, begging to be touched. She feels her clit swelling as a primal urge floods her thoughts of it needing to be nurtured.

Cassie's head sways back and forth as her hands shift from his hair to gripping the sheets as she tries in vain not to scream out loud. Just then, Billy drags his tongue over her hard nub for the first time. She let out a loud gasp as her hips rise off the mattress to bring him in closer. He pauses for a moment before latching on to her clit and sucking it between his lips and tongue, drawing it into his mouth.

"Ohhhhhhhhh, fuck, fuck, fuck..." the words involuntarily leave Cassie's mouth in a sensual tone as she's lost in the moment.

Wet sucking sounds start to fill the room as Billy slurps. Cassie's now swollen clit begins to grow more in size at the delicious stimulation it is receiving, making it easy for him to latch on, bringing her closer to another orgasm. Billy continues his assault on her senses as her legs spread wide, giving him complete access. He senses his Sister is about to cum multiple times but backs off just before pushing her over the edge. He then shifts one of his hands that had been holding both of her curved hips steadily in place and drags it to her now slick folds. He extends his middle finger and slowly traces her pussy lips as he removes his mouth from her momentarily. This change in sensation causes Cassie to gasp as though just surfacing from being underwater and needing a breath.

"Stop it, please." She pleads. "I can't take much more of this, Billy. Please, no more. It's too sensitive down there," She begs as she continues to try and catch her breath, but her Brother says nothing.

Just then, Billy stiffens one of his long fingers and penetrates her sopping wet vagina as his mouth again descends on her swollen clit, sucking it firmly into his eager mouth.

"Oh my god!!" Cassie screams before covering her mouth with her hand as if trying to put back the words she just uttered.

Billy picks up his passion as he works her clit with more energy. He greedily sucks, kisses, and laps up her juices, as his finger expertly saws in and out her wetness. Cassie's hips rise off the mattress and her back arches. She begins to scream as her body rears wildly. She feels an explosion of wetness leave her as her vagina walls begin to pulsate and contract on Billy's invading finger. She grabs him by the hair again and pulls his head, forcefully onto her pussy as she throws her legs wide open as he sucks and laps her sweet feminine delights. Billy adds a second finger and slides both deep inside her, which causes her legs to contract and close tightly around his head as if holding on for dear life.

"Oh, my God! Oh, my God!! Ughhh, ughhh, I think I'm going to..., Oh fuck Billy, ughhh!" She screams as her wetness turns into a flood as waves of pleasure rush through her entire body. She inundates her Brother's face as her juices flow freely over and into his mouth, while he continues to lick deeply between her pink folds. Cassie's back is arching high off the bed as the sounds of sloppy wetness, and loud moaning fills the room.

"Oh, my God! Oh fuck, Billy! Oh, my God!" She screams shrilly as wave after wave of a roaring orgasm ripple within her young virgin body.

"Oh, Oh, please no more, no more. Please stop, Billy! I can't take anymore right now." She gasps as her orgasm begins to subside, and Billy starts to kiss down her inner thigh while relaxing his fingers before slowly withdrawing both.

Cassie lay gasping for air as she brings one arm up, covering her eyes with her forearm in embarrassment. She questions what her Brother may think of her at this point. She wonders if she has been behaving like a slut. Her chest heaves upward with each breath she takes, as she tries to compose herself.