A Privileged Life Pt. 04

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"It's no imposition at all, Beverly. I would be more than honored to pass on any useful tennis tips to Cindy. When would be a good time for you, Cindy?"

"Cindy, you don't have any plans for this week. Why don't you meet Bella back here at the country club tomorrow," Beverly quickly suggests?

Cindy shrugs her shoulder and agrees to meet Bella the next morning at ten o'clock.

~~~~~

Billy sits at his computer wearing only boxer shorts. He slowly strokes his cock as he watches a video of a mother and son double teaming his younger sister. The mom is sucking one of her daughter's tits, and the brother is sucking his sister's other tit. Both are fingering the young girl. Mom has two fingers, sawing in and out of her daughter's pussy, and the brother is fingering his sister's ass with his middle finger in her tight sphincter past his second knuckle. The daughter's eyes glazed in ecstasy.

Billy's orgasm is bubbling in his sack and just beginning its journey up his shaft when the shower goes on in the Jack n' Jill bathroom connecting his bedroom with his sister's. Billy quickly chokes off his orgasm and dashes to the bathroom. Cassie is in the shower. He can see her silhouette through the frosted shower glass. Billy watches Cassie's tits jiggle as she lathers shampoo into her long blond hair. He slips off his shorts and steps into the cascading water behind his sister. Cassie gasps as her brother's hands cup her tits. He presses his hard cock to his sister's butt and gentle nibbles on her earlobe.

"Billy, that feels wonderful, but I have a dental appointment. You are going to cause me to be late."

"I can't help it, Cassie. I am so horny for you this morning."

Cassie turns and gazes into her brother's eyes. The pleading expression melts her heart. "I have time to give you a quick blowjob. Okay?"

Billy places his hand on top of his sister's head and guides her down to his throbbing cock. Cassie takes it all into her mouth. When it hits the back of her throat, she holds it there for a moment. Cassie relaxes her throat muscles and allows the mushroom-shaped head to enter her throat. She begins to swallow, causing her throat muscles to squeeze and massage his cock. Billy can't take but a few seconds of that, and his orgasm resumes its journey up his shaft filling his sister's mouth with his thick salty crème.

Billy's legs go weak, and he slides down the shower wall to the floor. His balls are still pumping cum as Cassie resumes her shower. After rinsing, she turns off the shower, steps over her brother, and dries herself with a towel. "You can return the favor when I get back from the dentist," she says over her shoulder as she leaves the bathroom.

By the time Billy recovers and goes down for breakfast, he finds that Cassie has already left for the dentist. His Mom is sipping a cup of coffee and reading the morning paper. She is wearing a tennis outfit. Billy feels an erection starting to stir. He loves seeing her in that short tennis skirt, which shows off her long legs and firm round butt. He also loves the way her polo shirt hugs her 36C boobs.

"Are you playing tennis today, Mom?"

"What tipped you off, Honey," she smirks?

"I... I just... ugh... I..." Billy stammers.

"I'm just jerking your chain, Honey. I know what you mean by that remark, and I just felt like being a smartass. I'm going to meet Cindy Wittington at the country club and give her some tennis lessons."

"I thought Cindy already knew how to play tennis?"

"She does, but her mother asked me to work with her to improve her game, and I agreed to do so."

"Oooooo... ugh... I'd love to come to watch. Cindy always looks so sexy in those short tennis outfits.

Bella would rather have Cindy all to herself but can't say no to Billy. "Sure, feel free to tag along if you wish. I'm sure Cindy won't mind."

"Ugh... maybe next time. I promised Cassie I would do something with her when she returns from the dentist."

"Okay, Billy. You are welcome to come along if you change your mind," Bella happily replies as she hurries out the door.

~~~~~

When Bella arrives at the country club, she observes Cindy sitting on a bench by the tennis court talking to Danny Gilmore. Danny is working part-time at the country club during his summer break before starting college in the fall. Cindy's tennis outfit takes Bella's breath away. It's a bit different from what she wore the day before. Cindy's top is midriff and exposes her belly button. The hem of Cindy's tennis shirt hits at mid-distance between the lowest part of her breast and her navel. Her belly button shows, and the shirt is short enough that it will show off her abs prominently. That is not a problem for Cindy nor Bella. Cindy is proud of her abs, and Bella enjoys viewing them. Like most active young women of her generation, Cindy has spent some time with bodybuilding. She is proud to show this outcome of all the hard work and painful efforts. Bella feels tightness in her chest, starting with a tingling in her nipples, traveling down to twitching in her moist pussy.

Cindy doesn't have large breasts, but her slender frame causes them to appear larger. She is maybe a firm 34B, but her tennis shirt's built-in bra barely provides enough support when moving around the tennis court. Bella suspects that Cindy's boobs will have a lot of movement when running around on the court, so she plans to return the ball to Cindy in a way to create as much activity as possible.

After the usual hugs and a quick peck on the cheeks, they take to the tennis court. They hit a few practice volleys. Bella studies the young girl's body and movements as she moves around the court. Bella tries to watch Cindy's backhand and forehand but pays more attention to her breasts' bounce and jiggle. Bella can't fight off the images of sucking on Cindy's youthful hard nipples.

Bella suggests she examine Cindy's grip on the racket. Cindy leaps over the net and approaches Bella. Her right breast escapes the built-in bra, and a dark pink nipple appears. Danny, who is working nearby, is the first to see her exposed nipple. Cindy is unaware of her exposure until she notices Bella's expression and the focus of her attention. She quickly tucks her breast back in place. Bella pretends it never happened and steps closer to Cindy to study her grip. The perfume Cindy is wearing makes Bella feel light-headed and excited. Bella's hand trembles and her voice slightly quakes as she displays a better grip.

Cindy notices Bella's nervousness and feels electricity between the two of them. Cindy was always attracted to Bella but never acted on it because Bella is her best friend's mother. Cindy didn't want to do anything that would jeopardize her friendship with Cassie. Cindy's panties moisten, but she fights off the urge to make a sexual move on her best friend's mother.

Bella suggests they play a match to gauge Cindy's abilities further. The first two matches go well, but both Bella and Cindy are not fully concentrating on the match. Cindy keeps visualizing Bella naked, and Bella continues to recall the nipple flash Cindy had displayed earlier. The noon sun glistens and gleams off the ripple of Cindy's sweat covered abs. Bella's panties flood again as she imagines herself, licking the sweat from around Cindy's youthful navel. The scene is so vivid in Bella's mind; it causes her to default on an easy return. Bella was on the tennis team in college and is not easily distracted, but Cindy's lithe young body is proving to be more than she can handle.

It is the last match of the set, and Bella shouts encouragement to Cindy, but it distracts her. Cindy tries to change direction, and her foot twists awkwardly beneath her, and she falls to the ground writhing in pain. When Bella reaches her, Cindy's left ankle is already beginning to swell. Danny Gilmore also dashes onto the tennis court. Danny scoops Cindy up into his arms after a brief assessment of her ankle and carries her to an empty bench. Bella is very conscious of Danny's hand, cradling Cindy's thighs. His hand is too close to Cindy's crotch to suit Bella. Those smooth shapely thighs had been in Bella's dreams a lot lately, and she wishes she could find a legitimate reason to touch them like Danny is now. Bella's anger slowly grows as she jealously watches his hand rest so very near to Cindy's young pussy, but she can keep her rage under control.

"Enjoy it while you can, Danny Gilmore," Bella thinks to herself as he gently places Cindy on the bench. "That is as close as you're ever going to get to her young pussy if I have anything to say about it," Bella grumbles to herself. She is careful not to reveal her thoughts out loud.

"Should I call an ambulance," Danny asks?

"I don't need an ambulance, Mrs. Davis. It just a twisted ankle."

"No, I think it's just a sprain," Bella replies. "I do think it would be a good idea if we can find someplace she can lie down for a while. We need to take as much pressure off that ankle as possible."

"The tennis pro is out of town this week, and there is a couch in his office where she can rest. I have a key to his office, and I would be more than happy to carry her there if you would like," Danny offers.

"That's an excellent idea," Bella replies.

Danny hands Bella the key to the tennis pro's office and then scoops Cindy back up into his arms once more. They make their way to the office, where Bella nervously fumbles with the lock. When the door opens, Danny gently places Cindy on the couch. He turns to Bella and asks, "Is there anything else I can do, Mrs. Davis?"

Bella hands him the office key and says, "You can lock the door on your way out, Danny."

"Yes, Ma'am," he replies, taking the key. "If you find you need anything else, just call the business office, and they will send me to take care of it."

Danny closes the door behind him, and there is a loud click when the locking mechanism falls in place. Bella checks the door to ensure it is secure and then goes over to the sofa and sits next to the injured girl. Cindy gazes at Bella in anticipation. She is not sure what to expect.

Bella instructs Cindy to lie back on the couch while she removes her tennis shoes and socks. Cindy's toenails are bright red, matching her lipstick. Bella thinks her tiny feet look delicious and the temptation to suck each precious little toe. The left ankle is red and swollen, and tender to the touch. Bella gently massages Cindy's whole foot. She runs her palm along the length of Cindy's soft under sole. Cindy giggles and tells Bella she is ticklish on the soles of her feet.

"Is your ankle tender where I massaged it, Sweetheart?"

"It's painful to the touch, but it also feels good when you massage it."

"I used to kiss my children's booboos when they were younger, and it always made the hurt go away," Bella smiles. "Would you like for me to kiss your ankle and make the hurt go away?"

Cindy gazes into Bella's eyes and slowly shakes her head, yes. Cindy's eager anticipation is evident. Bella feels a growing desire to hold Cindy in her arms but instead, kneels on the floor by the couch and positions herself for easy access to the parts she wants to favor.

Keeping eye contact, Bella kisses Cindy's ankle, foreleg, knee, and the rest of the way up Cindy's smooth thigh. Goosebumps blanket Cindy's thighs, and the scent of aroused teenaged cunt reaches Bella's nostrils. It makes her mouth water. She licks the tender flesh on either side of Cindy's panty covered pussy, then presses her mouth directly over the young girl's clit and licks the fabric itself. Bella presses her tongue hard against Cindy's clit and watches as Cindy's mouth opens and then sucks in a deep breath. Grasping the teenager's panties' waistband, Bella tugs them down, and Cindy raises her hips to accommodate her. Bella holds the girl's panties to her nose and inhales the aroma.

Cindy sucks in a deep breath and holds it. Bella stares at Cindy's naked treasure. It lay there pulsating, a feast for Bella's senses, and utterly forbidden. Cindy's pussy is plump like a teenage girl's, the inner lips completely hidden. The mound is thinly covered with blonde hairs so soft and fine they might have been peach fuzz. The outer lips are rosy pink and swollen. In short, Bella views it as fucking gorgeous. Cindy is still holding her breath. Bella pushes Cindy's legs apart and gazes into her eyes as she leans forward, tasting the young teen for the first time.

"Oooooo," Cindy coos. Before closing her eyes.

Reaching between the young teen's thighs, Bella pulls her slit open with her fingertips. Cindy's nectar coats her labia. Bella traces the folds of the young girl's delicate inner lips with her tongue and then spears her honey pot, tasting her sugary vaginal juices. Cindy drapes her legs over Bella's shoulder and rests her bare feet on Bella's back. That has the effect of pulling Bella deeper into the young girl's wetness.

Bella takes long, slow licks through Cindy's slit from bottom to top, savoring her taste. Cindy squeals each time Bella strokes her clit. Bella sucks the hood of her clit into her mouth and licks her little nub as fast as she can. Cindy explodes with her first orgasm and grabs Bella's hair, and squeals; her ass bounces up off the couch.

"Oh my god!" Cindy shrieks. "OH MY GOD OH MY GOD OH MY GOD!"

Bella dips her tongue into the teen's cavity to drink her juices and then ravishes her clit some more. Cindy orgasms again, and it is even more astounding. She is actually sobbing with pleasure. Her face contorts, and her mouth forms an 'O'. Cindy's thighs squeeze Bella's head, and Bella can feel Cindy's feet sliding up and down her back.

Bella brings her off twice more before Cindy begs her to stop. The little blonde rolls into a fetal position, her body twitching. She isn't likely to forget this orgasm any time soon. Bella rubs Cindy's back and soothes her through the orgasmic episode.

After a minute or two, Cindy stirs and sits up. When her eyes finally focus, she looks at Bella like she can't understand what had happened to her. Once Cindy is reasonably calm, Bella suggests she get dressed so she can take her home.

"What the fuck did you just do to me, Mrs. Davis," Cindy asks?

"I just made you cum, that's all."

"That's all? I thought I was gonna die. I've cum before, but I've never felt anything that amazing before."

"I'm glad you enjoyed it, Cindy."

"What about you," Cindy asks? "Don't you want me to make you cum a few times before we go home?"

"Honey, I have cum so many times while I was devouring your young tasty pussy, I don't think I could handle another orgasm right now. Let's save it for next time, and you can make me cum all over your sweet little tongue."

"Do you promise there will be a next time, Mrs. Davis?"

"I guarantee there will be a next time and a next time and probably many more times after that, but please don't call me Mrs. Davis. I think we know each other well enough now for you to call me Bella."

"Okay, Bella, when can we do this again?"

"Patience, my dear, patience. I promise it will be soon."

~~~~~~

Cassie walks through the bathroom that connects her bedroom with her brother's bedroom. She finds Billy sitting in his boxer shorts at his computer watching a porn video. He has earphones on and is unaware of his sister's presence. Billy slowly strokes his hard cock, which is protruding through the slit in his shorts. Cassie peers over his shoulder and studies the action on his computer screen. A middle-aged woman, who resembles her mother, has her face buried in a teenaged girl's pussy. A young teenaged boy is eagerly hammering the woman doggie-style from behind.

Billy is startled when Cassie reaches around his waist and takes over, stroking his cock. "Oh, shit... Cassie! Don't sneak up on me like that! I almost had a heart attack!"

"Wow, big Brother, you really are obsessed with having a threesome with Mom and me, aren't you?"

"Damn it, Cassie, I was on the verge of a perfect orgasm, and you startled me so bad I will have to start over again."

"I'm sorry, Billy. Here let me get you off quickly with one of my amazing blowjobs," Cassie giggled as she kneels between her brother's thighs.

Cassie takes her brother's cock to the back of her mouth and holds it there a moment before forcing it further into her throat. She swallows a couple of times, causing her throat to squeeze the head of his cock. Billy was already close to an orgasm, and it only takes a few rapid bobs of her head to bring him off. One massive spurt followed two smaller quirts, and Billy slumps exhausted in his chair, and Cassie swallows an enormous dose of his potent creamy cum.

"Oh shit, Sis, you have the most amazing mouth and tongue."

"So, I've been told on more than one occasion. No one has ever complained about my oral services.

Have you ever given Danny a blowjob, Sis?"

"Why in the hell did you ask me that?"

"Well... I have been thinking... The night of Homecoming, you were dancing with him, and I saw you stroking his cock through his pants."

"So, what if I was? You were acting like a dick to me that night."

"What do you mean I was acting like a dick? You were the one stroking Danny's cock on the dance floor. You are my little sister, and it upset me to see you acting like a slut."

"So, it was okay for you to grope the ass and tits of every girl you danced with, but if I stroke Danny's cock, I'm a slut? Just how did you arrive at that brilliant deduction?"

"Cassie, don't be that way. You are my sister, and I didn't want to see you cheapen yourself by acting like a slut. Hell... everyone there thought you were going to fuck him right there on the dance floor."

"And I would have fucked him later that night if you hadn't come through at the last minute and man up enough to do the job yourself!"

"Man up? Is that what you call it? Cassie... you practically raped me that night. I got the impression you went to Homecoming with the intentions of fucking me, your very own brother."

"That's exactly what I wanted, Billy. I was a virgin in a high school full of girls who had already experienced the joy of sex with a boy. And in many of those cases, the boy they were experiencing sex with was my big brother. Do you have any idea how embarrassing that was for me?"

"And I told you that night I didn't know you felt that way until you admitted wanting to come to my room and mount my cock. You should've come to me and explain what was going on in your head."

"Oh, yeah! I can just imagine how that would've gone over. I can see me coming to you and pleading with you to take my virginity because I didn't trust anyone enough to let them do it."

"Yes... I... I would've done it for you, Cassie. You are my sister, and I love you very much. I would've probably felt guilty about it later, but I would've done it for you."

"Do you feel guilty about it now?"

"No... not at all!"

"Well then, big brother, problem solved, and we live happily ever after," Cassie laughs. "And by the way, don't worry about Danny, I called him a week after homecoming, and we went down by the river, and we fucked for over an hour."

"I kind of suspected you two got together later. Was Danny as good as me?"

"He was different than you."

"Different how?"

He was rough. I like your gentleness better. But every once in a while, when I am really horny, I do like a good rough fucking like Danny offers."

"I can be rough if you want."

"Don't you dare change, big brother? I like you just the way you are, and besides, you can be satisfied with just a blowjob when I don't feel like getting down and dirty with you."

"You are truly skilled at oral sex. I can give you that much. Have you ever been with another girl, Sis?"

"Yes. I told you the night of Homecoming I learned how to kiss by practicing with other girls."