A Privileged Life Pt. 02

"No, don't, Billy. It's too sore and sensitive down there for that! You fucked me so hard last night my poor little pussy is raw. It was my first time, you know."

"I could always kiss it and make it better. A nice kiss from Mom always used to make my boo-boos feel better. Would you like for me to do that, Cassie? Would you like for me to kiss your sore little pussy and make it all better?"

"Let's get in my bed and give it a try."

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. He adds mild pressure to spread her legs. Cassie shivers in delight as his lips widen, and his tongue drags its way up one of her spread legs. She is not sure if she wants to risk his mouth on her sore pussy, and unconsciously reaches her hands down to stop his advances but with little effect. He can see just how wet she is and is delighted with the sight. He blows his hot breath on her raw pussy before switching to her other leg and once again kisses and licks her milky thigh as he pushes her legs farther apart.

When she senses his lips touch her delicate vagina, goosebumps run wild all over her body. 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 arm across her sore breasts to protect them from further assault. Her breathing begins to sound heavy, and a gentle squeal escapes her quivering lips as she shakes in ecstasy.

"No...! Wait, Billy! Please stop. I can't take it anymore. I'm just too sore down there. Please, I loved it when you licked me there last night, but it is just too tender today."

Billy is frustrated with his Sister. He doesn't want to stop feasting on her sweet nectar, but he also doesn't want to hurt her either. Out of frustration, Billy drops down and gives his little sister's asshole a nice tongue swabbing. Cassie giggles and releases her grip on his hair. She thrusts her butt against his tongue and trembles. Billy takes the hint and starts tongue fucking her musky tasting starfish.

"Oh my God, Billy. I love that! Please don't stop."

Billy ups his game by shoving his index finger two knuckles deep into her wrinkled constricted hole. Cassie's moans turn to throaty growls, and her sphincter muscle clamps down on Billy's finger. Her thrusting slows, and she holds her butt in the upward position longer. Billy feels her start to tremble. Then her body bursts open with orgasm. She screams out.

"Oh my God, Billy. You are making me cum! Oh... fuck... fuck... that's feels so fucking good!"

"You think that feels good, Sis? Just wait until you see what I want to do next. I promise it will blow your mind."

Cassie has a baffled look on her face when Billy tells her to get on all fours. She is apprehensive but follows her brother's instructions. Billy quickly retrieves a tube of Astro-gel from his bedroom. When he returns, he applies an excessive amount of the lubricant to her tight little hole. She watches him lube his throbbing hard cock with a look of hesitation. Billy understands his Sister is nervous, but she also appears curious and enthusiastic.

"What are you getting ready to do to me, Billy?"

"Just relax, Sis, and trust me. I promise you are going to love this."

"I hope you are not planning on putting that humongous thing of yours where I think you are!"

"I promise you, Cassie, it will feel awesome once you adapt to it."

"It's gonna hurt, isn't it."

"It probably will be painful at first, but I will let you control how fast and how deep we go. We can stop at any time you say."

Billy had read that the cowgirl position is beneficial for beginners because they can control penetration depth and speed. So, he rests on his back and tells Cassie to straddle him instead of doing it doggy style. His Sister obediently moves to mount up by placing her hands upon Billy's hairy chest. She lifts her butt a couple of inches while Billy reaches around behind her and grabs his slippery cock. He tells her to relax and then guides his cock toward her sensitive little hole. After some necessary "higher, lower, right there, lower," his swollen head presses against her puckered asshole. Billy begins pushing up as Cassie pushes down slowly onto his cock. Her anal ring fights to keep Billy's cock out.

Cassie looks down into her brother's eyes and says, "It's not going to work, Billy. It's too big to fit in me. Maybe we should stop."

Billy places his hands on her waist and abruptly pushes upward while pulling down. His bulbous head suddenly slides inside of her, eliciting a huge gasp, followed by an initial tensing and then a nervous smile from his sister. She is more surprised than anything else. Billy prompts her to relax and to kind of wiggle her butt. She does as he says and begins working his impressive length further and further inside of her, achingly slowly.

"Are you okay, Cassie?"

She doesn't speak but nods her approval. Billy maintains eye contact with her, watching her bite her lip and watching her eyes occasionally roll into the back of her head. Inch by inch, he feels his Sister's tight little hole clench around his shaft. It seems to be trying to fight the invasion off and, at the same time, trying to suck his cock in deeper. Occasionally, Billy lifts her high enough to feel his cock sliding out and then back in. He had read that would give her delightful chills as he pulls out. Cassie's nipples harden, and goosebumps cover her arms and legs. She begins to smile as she adapts to her brother's presence inside her virgin ass. Billy can see a mixture of pleasure and surprise on her face. He asks her if she is ok several times, and each time she nods yes and lets a quivering whimper escape her mouth.

"Is it all the way in?" she asks.

"It's about halfway," Billy lies. He doesn't want her to panic.

Cassie gives him a look that says, "Seriously?"

Billy adds, "You're taking this as a real champ right now, Sis."

"Jesus, you're fucking huge, Billy. I feel like it is about to come up through my throat. I'm not sure I can take much more. Can we just rest for a minute?"

Billy's initial reaction is that she's asking because she can't take anymore, and he is prepared to fuck her like that without going any deeper if that's what she wants. So, he replies, "Do you want me to stop or to go deeper?"

Without hesitation, Cassie replies, "Oh, absolutely."

"Well... Which is it? Stop or go deeper?"

"I can do this... Billy. I know I can. Please go deeper but go slower. Let me have more time to adjust. It's starting to feel good. It still hurts, but it's a good hurt."

Billy loves that Cassie is enjoying the challenge and that she is almost giddy that she can handle more cock than expected. It seems strange to admit to himself, but Billy is impressed that his little sister is taking his size like a champion. Cassie is a sister he had secretly lusted after, a sister who he thought would forever be off-limits, a sister who (until last night) he had never kissed on the lips is now taking his long, thick cock up her sweet little ass. He is so thrilled he almost dumps his load.

It takes at least another five full minutes before Billy is finally balls deep inside of her butt. When he let her know it is in, she smiles and says, "It's about time!"

Then she begins vigorously moving her hips up and down, causing him almost to slide out. He feels the chilly air on the exposed portion of his shaft each time she rises. There is also moisture on his balls. He lifts his hips, thrusting back into her just as she pushes her hips back to again impale herself on him. The contrast of the cold air in the room and the warmth inside her rectum is mind-blowing. He can feel the sap rising again and the beginning of an orgasm boiling in his balls. He needs to slow things down and make it last longer. He wants his sister's first anal experience to be fulfilling.

Cassie doesn't waste a single inch of his cock, grinding back down all the way each time, making sure she can feel him deep in her rectum. She begins moving more and more quickly until she is riding Billy as though he is in her pussy instead of her ass. Her perky tits are in his face, and he reaches behind her, pulling her hair to make her arch her back. He begins sucking and biting on her nipples as she ass fucks herself on his huge cock. She doesn't complain about her sore nipples. Billy loves that his Sister has adapted to ass fucking so quickly.

"You like that, don't you, Sis?"

"I love it, Big Brother. Aren't you happy you woke up when you did and joined me in the shower?"

"Yes, and can you believe that you almost passed on the chance to have my big cock balls deep in your ass? I could tell by the look on your face you were hesitant to give this a try."

"I promise never to doubt you in the future when you suggest kinky shit like this, Big Brother!"

"Ha... and you said it wasn't going to work, Sis? You said it would never fit in your tiny little butt hole. Aren't you glad you were wrong?"

Cassie is suddenly left utterly unable to speak. The pleasure has taken complete control of her mind and body. She just looks at her Brother with alternating looks of sheer lust, smiles, and looks that almost say, "Oooooo... fuck! If your dick weren't in my butt right now, I'd be so sad."

"Sis, your ass has adjusted nicely. Now I want to try a different position. Get on your hands and knees, and place your face in that pillow. Let's do this doggy-fashion for a while. I guarantee you will like that position even more."

Like everything Billy asks her to do, she trusts him implicitly and immediately puts her face down in the pillow, ass up in the air. Billy reapplies a generous amount of lube to his cock and presses it to her tender little starfish. He pauses to enjoy the sight of her firm bubble butt, her toned ass cheeks, and her glisteningly wet pussy. Cassie's freshly fucked asshole is inviting him to resume his very pleasurable assault.

It takes Billy's breath away when Cassie glances over her shoulder at him and says, "Kiss me, Billy. I need you to kiss me before we begin this new position."

Billy leans down and presses his lips to hers. It's an awkward stretch, but he manages to do it. His heavily lubed dick pokes her in her right cheek as they eagerly suck at each other's lips.

Billy pulls away from their kiss, places his cock just outside of her anus, and penetrates her from behind. It is much easier this time since she has already stretched herself nice and deep and impressively quickly while she was straddling her Brother's lap. Billy still takes his time to make sure she is comfortable in this new position. Cassie's already sexy ass looks even more mind-blowing to Billy as he watches his cock vanishing in and out of it. He finds it almost hypnotizing as it slides easily into his Sister.

She soon begins to push back against him on each thrust, her ass cheeks slap against his pelvis. He tells her to spread her cheeks so she can feel every last inch of his cock. She promptly reaches back, spreading her cheeks while making primal, guttural moans that are beginning to coax her Brother's cum to the surface again.

Cassie reaches between her legs and begins to rub her clit as Billy fucks her ass with long, deep thrusts. He feels her asshole start to tighten around his shaft as she is clearly about to explode with her first intense anal orgasm ever, and Billy can't hold out any longer either. She begins almost to scream as her orgasm overtakes her, and her asshole begins to alternately squeeze and release Billy's cock, making her even tighter and making her Brother start to empty his balls into her rectum.

Billy shoots wave after wave of warm sticky cum deep into her butt for what feels like more than a minute. Cassie collapses forwards, and Billy lands on top of her back. His cock still inside of her. He teasingly keeps sliding in and out a little bit as his erection begins to shrink.

Cassie giggles yet again and manages, through her still panting breaths, to say, "Holy fucking shit. That was absolutely incredible."

Billy slides out of her and watches some of his creamy sperm drips from her freshly fucked asshole. That immediately makes him hard again. He glances at the clock to see if they have time for more exploration. Cassie had already surpassed his wildest expectations. It is almost four o'clock, and their parents would be returning from the country club soon. He decides not to push their luck.

"Mom and Dad will be home soon, Cassie. I guess we should clean the place up, so they don't get suspicious."

"Thanks for the wonderful afternoon, Billy."

~~~~~~

Billy and Cassie clean her bedroom and the Jack n Jill bathroom before going down to the family room. They are watching TV when their parents return home from the country club.

"Well, I see that the King and Queen of Homecoming are finally up. Are you both rested now," Mom asks?

Billy only grunts, but Cassie smiles and says, "We both had a wonderful time last night. Billy may not want to admit it, but he had more fun than he would ever admit. Isn't that right, Billy?"

Billy feels the pressure to speak up. He doesn't want to create suspicions by overplaying his hand, so he finally says, "Yessssssssssssss. I did have fun, Mom, and yessss it was more fun than I initially anticipated. Why is everyone so concerned if I had fun?"

"You didn't have much to say when you got home," Dad replies. "Cassie said it was because you were tired, but your Mom had a different take on your mood."

"Well, Cassie should know. It was all the strenuous activities she put me through that made me so tired!"

Cassie hits him on the shoulder with her fist. Billy flinches and rubs his shoulder. He looks at his Sister as though to say, "Why in the hell did you hit me?" Their Mom smiles but looks at Cassie with a skeptical expression.

Billy realizes how sexually suspicious that sounds and blushes before stammering, "Cassie thought being the Queen put her in control and her demands are what tired me out."

That explanation doesn't sound any less suspicious, considering what did happen at Homecoming. Still, before he can put his foot any further in his mouth, Cassie decides to come to his rescue.

"I just made sure he lived up to all the responsibilities of the Homecoming King."

That explanation sounds even worse, and both Billy and Cassie turn crimson red. Mom has a knowing smile on her face. Dad has a blank expression and says, "Well, I'm glad you both had a good time at the dance. I'm going to be in my workshop. Call me when dinner is ready."

"I'm going to take a quick shower before I prepare dinner," Mom says before ambling toward her bedroom. Billy stares at her butt as she walks down the hallway. Cassie punches Billy in the arm.

"You do want to fuck Mom, don't you, Billy!"

"I do not!"

"Yes... you do, Billy. You were just looking at her ass like you wanted to stick your tongue up it just like you did mine earlier."

"Give it a rest, Cassie! And stop punching me in the arm."

"It's okay if you do want to fuck Mom, Billy. She has a nice-looking ass. I can understand you looking at her like that. She's a beautiful woman. And if you want to fuck her, I will help you achieve that goal."

"Am I that obvious, Cassie? Do you think Mom is aware of my feelings toward her? Does she know I am looking at her in that way?"

"Yes. Yes. And Yes. You do look at Mom that way, and yes, she is aware you are looking! And I am pretty sure she knows you want to ravage her."

"Oh shit, Cassie. Why didn't I realize I was so obvious? Why wasn't I aware she knew I was lusting for her?"

"You're a man, Billy. Men are always checking out a woman's ass and tits, but they should also be watching the woman's eyes. If you took the time to watch Mom's eyes, you would see she has checked out your butt a few times. And she has also noticed that monstrous bulge you get in your pants while you drool over her cute little bottom."

"How do you know that?"

"Well... unlike you, Billy, I pay attention to things like that. I told you before, the way you were looking at Mom, and the way she was responding is what gave me the desire to have sex with you."

"Cassie...? Do you honestly think Mom would let me or anyone else fuck her?"

"Yes. But you would have to seduce Mom first, and if you conducted the seduction correctly, your chances are pretty high."

"No, not Mom. I can't see anyone making love to Mom but Dad. She's not that kind of woman."

"That kind of woman? Billy, practically any woman can be seduced by any man, or woman for that matter, if she has an unfulfilled need and the seduction is done properly."

"Don't bullshit me, Sis, and don't prank me. You, honestly, believe someone other than our Dad can seduce our Mom?"

"I do. If the seduction is done properly."

"Well...that's the key phrase; if it is done properly," Billy says. "I don't have any idea how to seduce a woman, much less my Mom."

"That's where I come in, Billy. I am going to coach you through the essential steps to seduce Mom appropriately. When I am through, you will have the skills necessary to seduce any woman."

"Any woman?"

"Let's just concentrate on Mom first. And while I am thinking about it, you will never get to first base with any woman if you stare at her body like a hungry wolf eyeing fresh meat. An admiring casual glance is okay and is often taken as a compliment, but lustful staring is a real no, no."

"I never thought of it that way, Sis," Billy replies.

"And remember, Mom is not a slut, so don't expect to talk her into your bed in a few short weeks. Seduction is all about paying attention to someone else's needs and moving forward accordingly. If you truly want to seduce a woman, spend time getting to know her and her body language. Set an appropriate atmosphere for the seduction, and move slowly, very slowly before getting too physical."

"What should I do first?"

"Well, you already hug Mom occasionally. I suggest instead of gawky; you hug Mom more often and maybe follow up the hug with a kiss on the nape of her neck. The neck and ears have many nerve endings and are generally not touched as often as they should be. I love it when someone kisses my neck, where it intersects with my shoulder. Nibbling on a woman's earlobe is a real turn on for her, but that's not something you want to do right away. Let Mom get used to gentle kisses on her neck before you move to an advanced technique such as earlobe nibbling. Remember to go slow and pay attention to how she responds to different things."

"Cassie, just how often have you let boys kiss you on the nape of your and how often have they nibbled on your earlobe?"

"Shut the fuck up, Billy. No one likes a smart ass!"

Wisely changing the subject, Billy asks, "Do you think Dad is aware of my lusting for Mom?"

"No... Not at all! He's a man and is no more aware of what's happening around him than you are."

"Cassie, are you telling me that Dad doesn't notice that other men look at Mom with lust in their eyes? Because I notice men looking at her like that all the time. Every time she wears a bathing suit or tennis outfit at the country club, men stubble all over the place, ogling her body."

"Oh, he notices other men looking. I just don't think he's noticed you looking because of the mother/son relationship. If Dad has noticed you, I think he is probably relying on Mom to keep everything under control."

"Cassie, I would love to know what Mom thinks about me looking at her that way. She's never said anything to me about it."

"Do you know anything about body language, Billy?"

"I've read about it on the internet. Why?"

"When a woman IS attracted to a man, it's often way too subtle for him to pick up. But...don't worry, because there are a few female body language signs that indicate she's attracted to him. However, the man must pay real close attention to them because many of the signals aren't very clear. You mainly need to watch a woman's eyes. If you are busy gawking at her tits, you will miss the signs. You will also run the risk of turning her off. You come off looking like a creep if you constantly stare at her tits."