A Privileged Life Pt. 05

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This is a five-part story. The same characters are used throughout, and it would be very beneficial for you to read the other four parts to understand what happens and why in this part fully. The story is a bit long and contains a lot of sex. If you are opposed to incest, anal sex, wives sharing their husbands, girl-on-girl sex, or threesomes, you should move on to another story because this story contains all of the above. I love to receive comments and suggestions from readers, but this story is not intended to open a debate on acceptable behavior between consenting adults. This is for entertainment only!

The smell of freshly-brewed coffee and sizzling bacon draws Billy down to the kitchen. He sneaks behind his sexy Mom and caresses her breast while pressing his morning woody against her butt. His Mom’s nipples instantly stiffen at the feel of her son’s hands, and she pushes her butt against his hard cock. Billy moves one of his hands under his Mom’s robe and cups her dripping wet pussy.

“Oh… I see you are ready for me, Mom.”

“Yes, and no… Maybe later, Sweetheart, because your sister will be waltzing in here in a few minutes, and you know how she is if she thinks we are not including her.”

“I don’t mind getting her off with my tongue if she shows up before I have time to recharge,” Billy pleads.

“We can’t, Honey. Your Dad is upstairs sleeping. Maybe we can sneak something in later this afternoon.”

“What’s Dad doing home? He should be at the hospital right now!”

“Your Dad was called to the hospital last night to perform an emergency cardiac surgery procedure and didn’t get back home until well after 4:00 AM. And since it’s Friday, he’s decided to take the rest of the day off and catch up on his rest.”

Billy’s cell phone rings, and he can see by the caller ID it’s Danny Gilmore calling. Danny wants to come over and hang for the day. Billy glances at his Mom with a questioning look, and she nods her approval but warns they have to be quiet and not disturb his Dad. Billy gives Danny the okay and clears his breakfast dishes from the table. Cassie comes down for breakfast just as Billy is stacking his dirty dishes in the sink. She is still wearing her cotton nightshirt, and her stiff nipples are prominently pressing against the soft fabric. Billy’s eyes shift to her pointed nipples like a magnet to its polar opposite. She ignores Billy but hugs her mother then pours herself a cup of hot coffee. Cassie inhales the coffee’s aroma before taking a sip and signals her approval with an “Mmmmmm… ”

“You must have partied late last night, Cassie. You look like crap this morning,” Billy smirks.

“Thanks for the compliment, ‘Shithead,’ you look great too!”

Billy laughs and heads for his room. Mom puts a plate of eggs and bacon in front of Cassie and pours herself another cup of coffee. They chat for a while, and then Mom points out that Danny is on his way over to visit. She suggests Cassie go to her room and change into something more decent.

“I’m not worried about Danny seeing me in my nightclothes. He is practically like a brother.”

“I hope that doesn’t mean you are fucking him too.”

“Mommmm… that wasn’t a very nice thing to say.”

“I know, Sweetie, I just felt a bit devious for a moment.”

“Well, for the record… Danny and I have helped each other out with certain needs on a few occasions.”

“I don’t want to hear about it, young lady. I need to get busy with my house cleaning. And when you go back upstairs, get my dirty lingerie from the hamper in my bathroom and bring it down. I am going to do some laundry in a bit, so if you have dirty panties or bras, bring them down too.”

“I may have some soiled panties. I did go out partying last night as Billy so rudely pointed out.”

“Oh… and be quiet when you go into my bedroom. Your Dad is asleep because of a long surgery last night and didn’t get to bed before four o’clock this morning.”


Cassie eases the door to her parent’s bedroom open and observes her Dad sleeping on his left side. He is wearing only boxer shorts. She tip-toes quietly into their bathroom. When she lifts the clothes hampers’ lid, a pair of her Mom’s panties are on top of the pile. There is a damp spot around the crotch. When Cassie examines them, she finds a creamy white glob nestled in the gusset. She thinks she knows what it is, but she dips a finger in it and brings it to her tongue. She is right in her assumption. It is definitely a specimen of male sperm. Probably her Daddy’s sperm. The thought of tasting Daddy’s sperm excites her, and she licks the remaining traces from the gusset of her Mom’s panties. The salty taste gives her an erotic thrill. She had often wondered how her Daddy’s cum would taste. She never dreamed she would ever get to taste it.

Cassie gathers the rest of her mother’s dirty lingerie and prepares to leave, but her eye catches something that draws her interest. hiltonbet giriş Her father’s flaccid cock is hanging out of the slit in his boxer shorts. Cassie’s heart starts to race with excitement, and within seconds her hammering pulse is centered between her legs. Cassie can barely move; her thighs drift open, and her hand drifts to her pussy, which is aching with an overwhelming reaction. The sight of her Daddy’s cock is making her feel too weak and shaky to move. Part of her feels ashamed and embarrassed, but another part of her is aroused by the sight of his cock. There is a moist heat swarming through her pussy now. Cassie wants to touch her Daddy’s cock. She can’t fight the temptation and soon gives up on whatever will she had left to fight it.

Cassie knows she should leave the room because this is her father, and purposely touching his cock is the last thing a daughter should do, no matter how much she is dying to feel it. Meanwhile, the moist heat keeps building in her pussy, wearing down her better judgment. She spends a long time just staring at the shape hanging from her Daddy’s briefs. Cassie feels like she is gazing at a beautiful piece of sculpture. It is so long and slender, and the mushroom-shaped head looks so shapely as the ridge flares around the upper end of his shaft. She estimates it to be at least six inches long in its flaccid state.

There is no question that Cassie’s pussy is now soaking through her panties and trickling down her thighs. It didn’t seem fair that her own father should have such a perfect cock. She wants it, pure and simple, but it belongs to her mother and is the one cock in the entire world she should never covet. It would be so simple to move her head down and take that large, delicious-looking cock head into her mouth and suck. She tries to imagine how it would feel to have his cock pulsing in her mouth as he pumps her a creamy load of cum.

Cassie has no real hope of ever touching it, but on the other hand, it doesn’t seem so awful only to look. She lifts the band of her father’s briefs to get a better view of his beautiful cock and hairy balls. His balls are large and round and covered with thick dark hair. She peers into his briefs for as long as she dares. At the same time, her pussy is aching for attention. She would love nothing more than to have that huge cock pumping deep and hard into her soaked cunt, but she knows that imagined ecstasy is only a fantasy that would never happen.

Cassie keeps staring at the full, round head while she carefully slips her hand down inside her panties. Her fingers then slip down farther, into her panties and onto her pussy mound. Cassie’s hand burrows a little deeper so she can stroke the hairy lips of her dripping pussy while she stares at the ripe, rigid cock sticking up out of her Daddy’s briefs. Her hand wedges between her thighs, and she is trying to be careful not to wake up her father. What would he think if he suddenly opened his eyes to discover his cock sticking out of his briefs while his daughter is right against the side of his bed rubbing her pussy?

As Cassie’s fingers slipped and slid over her wet, slick pussy, she quickly loses her ability to think straight. If she could’ve brought her mouth to her father’s cock without waking him up, she would’ve done it, but the idea of getting caught horrifies her. The chances she has already taken is terrible enough, but she never dreamed she would ever enjoy the sight of her Dad’s gorgeous cock.

The impossibly horny daughter forces herself to make as little movement and noise as possible while she attacks her swollen clit with her fingers. She rubs her slippery nub as hard and fast as she dared while she keeps her eyes on her Daddy’s cock and again imagines how it would feel inside her mouth. Shivers of forbidden pleasure grow in her body until she finds herself on the edge of an orgasm. It is so delightful and shameful all at the same time. She feels the waves of pleasure racing toward a magnificent orgasmic crescendo.

Wave after wave of orgasmic joy ripples through her inflamed body as she fights to keep from making any sudden noises or movements. The hot pleasure is overpowering, and when the explosion finally happens, she has no idea how she can keep from screaming her delight. Her father continues to sleep the whole time peacefully.

She finally pulls her hand out of her panties and sucks each of her wet fingers clean. After that, she lay her head against the side of her father’s bed, only inches from his cock. Cassie is so close to the tip of his penis she could literally stick her tongue out and touch it. She knows that she needs to slip away before her father becomes aware of her presence, but she wants to stay there forever. Cassie finally comes to terms with the fact that she has to go. She gazes down at his cock with a girlish smile on her lips, and before she knows it, she is closing her lips around the soft spongy head. Her father continues to sleep as she circles the head of his cock with her tongue hiltonbet yeni giriş before quietly retreating toward the door. Henry opens one eye and admires his daughter’s firm round butt as she makes her way to the door. She turns to take a last look, and her Dad quickly shut his eye. If Cassie thinks her father is totally unaware of her ever being there. She is wrong.


Bella is running the vacuum in the front living room and doesn’t hear Danny knocking on the front door. After three unanswered knocks, Danny opens the door and walks in. Bella has her back to the door and is unaware of his presence until he kisses her on the neck.

“Damn it, Danny! Don’t sneak up on me like that,” She screams through clenched teeth!

“You look really Hot today, Bella.”

She puts her forefinger to his lips and whispers, “Don’t call me Bella when my family is around, Danny. Please, let’s just stick with Mrs. Davis except when we are alone together doing what you are really good at, okay?”

“Yes, Ma’am, Mrs. Davis,” Danny answers like a scolded child and proceeds towards the stairs.

“Oh… And Danny, I look forward to our next rendezvous as much as you do, but I do need to keep it a secret from my family, okay?”

Danny nods his okay and continues to Billy’s room while recalling each delicious moment he spent with Bella a few days ago. He remembers the feel of her firm breasts in the palms of his hands. The taste of her feminine juices on his tongue is still on his mind, as well as the magnificent massage her vaginal muscles had given his teenage cock. Bella admires his firm ass as she watches him climb the stairs and then goes to the laundry room to fold sheets and towels.

Billy is in his bedroom awaiting Danny’s arrival and savoring the memory of his first time with Helen Gilmore, Danny’s Mom. Helen is a knockout, and in Billy’s opinion, she is the ultimate MILF. Billy will never forget that first time he had sex with Helen Gilmore. As soon as Billy hit adolescence and learned about the opposite sex, he was drawn to Danny’s Mom. It has always been a challenge for Billy not to stare at her or ogle her. The older he has gotten, the better his self-control around her has become. However, she is so pretty that whenever she smiles at him with her brilliant smile, his knees still go weak. She is truly stunning, and the only thing nicer than her smile is her body. It’s perfect, and Billy loves everything about her gorgeous body.

For as long as Billy can remember, Helen Gilmore has played a significant role in all of his sexual fantasies. Danny’s Mom has frequently invaded Billy’s masturbation fantasies for as long as he can remember. Ever since Billy entered his teenage years, Helen Gilmore has been the star of all his pornographic wet dreams. Billy could only drool and wonder what it would be like to touch her silky-smooth body and gaze into her enchanting eyes while making love to her. That is until Danny and his Mom, Helen, invited Billy to go along with them on a weekend trip to the family’s mountain cabin. Billy leaped at the chance to be near her for an entire weekend. Billy loves the outdoors almost as much as he loves being around Helen Gilmore. So, Danny, his mother, Helen, and Billy piled into the Gilmore family car, and off they went to the mountains. And you guessed it before that weekend was over, Billy had fucked his fantasy MILF.

There was fresh snow on the mountain, and the weather couldn’t have been better that weekend. The rooms in the Gilmore family’s cabin were cozy and welcoming. On their first day at the place, Danny and Billy hiked until they were almost too exhausted to walk. Then they returned to the cabin where Helen had built a warm fire in the fireplace and prepared hot cocoa for them. A delicious dinner followed the hot cocoa. It was the start of a perfect weekend.

There is a luxury ski resort, a short car ride away from the cabin with a couple of bars and night clubs that offer nightly entertainment. Most nights, there are some very attractive women at the resort. Some are young college girls, but many women are either married or older than Danny and Billy. The two best friends look like college guys but didn’t have ID’s that could stand the scrutiny of a wise bartender. Knowing the otherwise unattached college girls would not want anything to do with a couple of high school nerds. They won’t be college freshmen for another couple of months. Billy and Danny had to be content with just eyeing the pretty college girls and drinking the beers Danny’s mother bought for them.

They enjoyed watching the college chicks moving around the dance floor, but to tell the truth, the most alluring and sexy female in that place is Danny’s Mom, and she is sitting at their table. Billy feels like a big shot when he notices men of all ages ogling Helen with lustful envy. He tries not to stare at her, but she is just so damn sexy that it makes his heart race only to be near her.

Danny and Billy aren’t used to hiltonbet güvenilirmi drinking much, so they are both fairly plastered after four or five beers. Helen drives them back to the cabin, and Billy goes straight to bed. He falls asleep instantly and sleeps like a log until he wakes up about an hour later, needing to take a colossal piss. The beers had gone right through him and filled his bladder. Billy gets up quietly and goes into the bathroom to relieve himself. On his way back to bed, he looks over at Danny’s bed to be sure he hadn’t awakened him and finds that his bed is empty. Danny isn’t there now, but it’s obvious he had been.

Billy thinks it is strange but figures that Danny is probably getting something to eat in the kitchen, so he just goes back to bed and prepares to sleep off a very long and tiring day. Just as he is drifting off again, he hears some odd sounds. It sounds like muffled voices and light bumping sounds coming from the bedroom next door, the bedroom where Danny’s Mom is sleeping. Billy is suddenly concerned that maybe something is wrong with Helen. But the more he listens, the more he becomes convinced that the sounds he is hearing are the noises of two people having sex. He hears grunting and groaning and an occasional, “Yes, yes, Oh my god, yes.”

Billy assumes that Helen must have gone back to the night club after dropping him and Danny off. There had been several men flirting with Helen, and she had flirted back with some. Billy didn’t want to acknowledge it, but Helen may have invited one of those men to come to her cabin. He reckons some guy is probably getting lucky with Helen; VERY lucky. Billy would have given anything to be the one with her. Billy instantly develops a raging hard-on that won’t let him go back to sleep. Billy doesn’t want to jack off in bed as he assumes Danny will be back from the kitchen at any moment, and it would be somewhat embarrassing to get caught playing with himself. So, he decides to get up and go down to the kitchen with Danny and maybe eat something.

Billy has to pass by Helen’s bedroom door on the way down to the kitchen, and as he does, he is suddenly shocked by what he hears and freezes right there in his tracks. The voice he hears, coming from Helen’s bedroom is Danny’s. Billy can listen to what is going on in the room now that he is closer to the door. And it does indeed sound a lot like two people in the throes of passion. The grunts and groans are louder, and the bed is squeaking and bumping. There is no doubt that two people are fucking like crazy behind Helen’s bedroom door in Billy’s mind. Billy knows in his heart that it is not Danny in Helen’s bedroom. It can’t be. He is her son. Billy refuses to believe that Helen Gilmore is fucking her son.

Billy rushes downstairs and quickly checks the kitchen and the den but no Danny. Billy has to sit down in the nearest chair to gather his wits. Danny? And his Mom? No way! No fucking way, Billy thinks to himself. But, the evidence seems to support his initial suspicions, leaving little room for doubt in Billy’s mind. Billy can hear Danny’s voice … and his mother’s voice. It had to be Danny in that room. Even though Billy is in shock, his boner is unabated. It pokes against his shorts, making a wet spot at the top of the tent.

The thought of Danny fucking his Mom is more than Billy can fathom. Billy couldn’t have stopped himself from doing what he does next if his life depended on it. His hard cock is spurring him on. Billy sneaks back upstairs and creeps up to Helen’s bedroom door. Then, with little or no hesitation, he crouches down on his knees and puts his ear to the door. It isn’t long before he hears Helen. She gasps, “Oh … my … god!”

It is them alright. And from the sounds Billy is hearing, they are indeed fucking. Billy thinks his big and little heads would both explode at the same time. But, as aroused as he is by what seems to be happening, there is something very odd about what he is hearing. Billy can just make out Danny is calling Helen, ‘Mom.’ But Helen isn’t calling Danny ‘Danny,’ or even ‘son.’ For some bizarre reason, she is calling him ‘Daddy.’ At first, Billy thinks he is still a bit drunk, but the more he listens, the more he is sure. Helen Gilmore is calling her son, ‘Daddy.’

Billy is so stunned that he involuntarily gasps a little too loud, and the next thing he knows, the bedroom door opens, and Danny is standing there looking down at him. Danny’s cock is erect and sticking out straight in front of him. It is right in front of Billy’s face and covered with moisture that smells a lot like pussy. There is no doubt left at that point, Danny had been fucking his Mom. Billy half expects Danny to be mad at him and take a punch at him or something, but Danny just looks down at him, crouching in the hallway.

With a kind of gloomy look on his face, Danny sighs and says, “Come on in, Billy. You can watch.”

As those words scorched their way into Billy’s brain, he can’t help but look past Danny to the bed. He observes the incredibly sexy and juicy Helen Gilmore lying naked on her back with her thighs spread as wide as a prostitute’s. Billy is speechless. Seeing Billy’s shock at the sight of Helen’s glorious body stripped bare, Danny just reaches out and takes Billy by the arm and gently leads him into the bedroom.

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