The Family

Story Info
Family tale of incest, crossdressing and FLR.
2.9k words
3.96
11.4k
14
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

... a story of a family I know well... this involves crossdressing, humiliation, and incest between parents and their adult children...

Shaking hands and offering a tender hug to Pastor Paul, the well-dressed and groomed, mid-sixties couple smile and thank him for a spiritually rewarding Sunday service. They walk hand-in-hand from their place of worship to the gleaming 7-series luxury sedan parked at the front of the lot due to their significance within the congregation.

Whitney and Charles ... the short drive from church to home is a quiet drive with only Whitney speaking of a few passages shared by Pastor Paul. Just before pulling into the long driveway, the gentle chimes of Whitney's phone rings. "Yes, honey ... Mother is listening," is Whitney speaking to the younger of their two male children. Charles pulls into the driveway and silences the auto. He slips from the drivers seat, opens Whitney's door but moves away as she speaks on the phone and shows no sign of exiting.

Charles passes through the living room to the back of their home and the Mistress bedroom as it has been renamed. He slips off his expensive suit coat and unfastens his tie as he looks in the full-length mirror. His skin-smooth bald head glints with the morning sun shining through the large window. "I will tell your father that you love him," Whitney signs off and silences the phone. "Michael is having marital problems. Danielle asked if they could take a break so Michael will be staying with us for a time."

Charles turns, his belt unfastened with tailored dress shirt and tie already removed. His white lace brassiere covering his torso with the garter belt evident in open trousers if Whitney had taken the moment to notice. Their older son, Andrew, had recently decided to move back from New York and had asked to stay with them until he was settled. Charles slipped off his trousers and proceeded to hang them with his suit coat in the expansive closet. Exiting the closet, he now stands before Whitney in white lace bra with matching garter and thong, sheer nude stockings and open-toed heels.

"Having both the boys at home will unsettle our routine just a little bit but we will persevere for them. It's not as if we have ever kept our personal lives a secret from them. And they will need our love and care as they both are going through bumps in their lives," Whitney said to Charles before gently caressing his panty and feeling the bump of steel that traps his penis. Whitney's hand slips away and turns so Charles may undress her as if he is Whitney's chambermaid.

***

Pastor Paul has joined Whitney and Charles for Sunday evening supper as is the twice-a-month tradition. Paul is married to Charles's sister but she sits at home waiting for her husband to return. Charles moves about the kitchen preparing the meal while his wife and brother-in-law sip red wine and discuss the mornings sermon. Charles now wears a shoulder length black wig with bangs. He wears a conservative grey sweater dress with his heels and feels much more comfortable for his appearance.

Both Paul and Whitney are respectably dressed though Whitney does not wear a bra and her heavy breasts and fat nipples are evident. They sit on the couch holding hands and speaking softly to one another. Dinner in the formal dining room is served by Charles. Then he takes his place at the far end of the table, almost an observer to the meal. Acting also as the traditional 'woman of the house', he will rise to refill their wine glasses without being asked.

With dinner complete, Charles tends to clearing the table and cleaning up the kitchen. As Whitney tends to Paul. They have adjourned to the Mistress bedroom. Whitney has shed her dress and panty's, now only in garter and stockings and heels. Paul carefully removes his suit and underwear then turns to Whitney as she sits on the edge of the bed. Her hands slide around his hips to dig manicured nails into his asscheeks. Taking his soft uncut cock into her mouth, she feels him begin to grow.

Unlike the smooth all-over appearance of her husband, Paul is a hirsute man with dark hair though some of it now grey. As his cock grows, his head now pushes to Whitney's throat. She pulls on his foreskin to expose him and press her lips about his shaft. Her left hand presses against her bald cunt, fingering her wetness and teasing her aroused clitoris. With Paul now erect, Whitney slips her mouth from him and lays back on the large bed. Her legs open, her cunt glistening for him.

Pastor Paul moves between her thighs and mounts his sister-in-law in the classic missionary position. His mouth drops to suckle her right nipple, pulling her fat nub deep. His cock presses and Whitney gasps loudly as his thick cock plows her pussy. Her body pushes upwards to take his cock. Dropping her tit from his lips, Paul begins to fornicate with his favorite parishioner. For nearly ten minutes his cock rides deep within her body and brings her to multiple orgasms. As perspiration drips from his brow, he pushes fast and deep with his cock. Eyes close as he feels the rush of semen flooding Whitney's cunt before collapsing atop her with a soft "Amen".

***

A simple lavender lace nightie with thong panty, Charles slips into the dark bedroom. Closing the door behind him, he walks to the bed and gently pulls back the sheets to slip in beside his eldest son. Andrew had not yet fallen asleep though the day of travel had him weary. He opens his brown doe-like eyes to see his father in nightie joining him in his bed. "Your Mother - always concerned about you - thought you might need some help relaxing." Charles's voice was soft, his hand reaching out to feel his son's soft cock twitch.

For reasons he did not understand, Charles was pleased to find Andrew sleeping nude. He put his hand on the smooth chest before moving slowly and tenderly over Andrew's belly before feeling his mound of pubes then his soft cock. His hand slips around his son's cock and begins to slowly massage with his fingers and thumb. Andrew's long blonde hair falls across his face as he rolls slowly onto his back. He now feels the weight of his father's torso move across his upper thigh and lips kissing on his belly and groin.

This is not the first time for Charles with Andrew but it has been years - it was before Andrew had moved across country to live. He wished that Whitney had allowed him a wig tonight but she was clear that he would go to their son with his bald head. She knew this always humiliated her husband to not look so feminine when being asked to be. As Andrew's cock began to stiffen, Charles presses his lips around the head and began to suck. His hand continues to stroke from balls to his own lips making Andrew hard.

In the next bedroom down the hall, Whitney had entered shortly after Charles had done the same. Michael was still awake and scrolling through his phone. He looked up when the door opened and was not completely surprised to see his mother standing in the doorway. Her large, creamy breasts hang softly under the sheer material tied only at the waist. She walks towards her younger son on heeled slippers with sheer thong barely concealing her smooth vagina. Michael sets down his phone and pulls back the covers.

His cock soft as his Mother gazed at his nude body. His chin covered with a couple days stubble making him appear a few years older than he is. Whitney sits on the bed near the mid-section of Michael, her hand gently stroking his cheek. Michael's eyes flicked from her face to her heavy breasts and back to her eyes. Whitney, ever seductive, casually pulled on the tie to expose her torso and breasts to Michael. "Now, my handsome Michael, lay back and let Mother take care of you."

She had known of his issues with Danielle - both out of and in the bedroom. He had confided with her that he had not enjoyed an erection in more than three months and was worried it was him. Now, just seeing his Mother's large, creamy breasts gave him a twitch that he has not felt in what felt like forever. Whitney slipped off the nightie and eased the thong from between her shaven snatch. She leaned down and softly kissed her younger son's lips. Lingering, he lifted his head to kiss her back as his hand slipped behind her head and pulled her close. Tongues twisted as Michael now felt her hand slipping over his crotch.

Neatly trimmed, blonde pubes highlighted the shape of his pink cock. Whitney's mid-60's year-old body now lay against her son's 31 year-old nude body. Her hand rubbing his balls and softly stroking his softness as they continue to kiss. After a few minutes, she feels it. She feels his cock begin to stiffen. Michael's hands are now rubbing and kneading her heavy breasts as they still kiss with tongues. She breaks the kiss and feels Michael shift so his lips are now surrounding her fat left nipple.

He closes his lips and pulls as Whitney begins to softly moan. She can feel her pussy grow wet. Her hand softly stroking his cock as he begins to elongate in his Mother's hand. An erection that he has desired for months and unable to achieve with his wife.

Andrew begins to softly moan as his father's mouth surrounded his cock. Charles was now deep throating the eight inch erection. His face now pressed into the thick mound of pubes. Charles's body now between Andrew's thighs. His index finger teasing the sweaty anus pressed to the sheets. His right hand still rolling Andrew's heavy ball sac as he sucked cock. Taking him deep into his throat as he had been taught by Whitney so many years ago.

Andrew was sure his Mother was in his younger brother's bedroom taking care of his cock. He reflected back on his years in New York where he spent many nights with a variety of partners, both those with pussy and those with cock. His long hair draped over his chest as his left hand caressed the bald head of his father. His father wearing a lavender nightie and sucking his cock. He could feel himself edging closer to his orgasm but wanted more than a tight throat.

Andrew's hand pulled Charles' face from his cock. A long string of drool connected them as his cock flopped onto his pubic mound. "I know Mother has taught her chambermaid many skills since I left home," Andrew said to his father. He knew his words would embarrass and humiliate. And make him even more needy. Charles raised up to his knees as his nighty fell around his thighs. He really wished his smooth skull was covered by one of his wigs. He looked up the bed at his beautiful son. His skin soft, his facial features so smooth and effeminate - the look that confused most people about his gender.

Then Charles looked down at the eight-inch erection that he just had in his mouth. "Yes, my son, your father has learned many skills since you left home." He moved alongside his son and got on his hands and knees. Andrew gave him a quick kiss on the mouth then moved to the foot of the bed and got between his father's parted legs. Andrew's thin, yet toned, body contrasted with the middle age sag of his father's skin. He lifted the hem of the nightie to expose the lavender thong tucked tightly between smooth cheeks.

Andrew's hand slipped between Charles' thighs and caressed the front of the thong. His father was soft, only a small bulge unable to achieve any sense of erection anymore. He pulled the thong from between the cheeks and exposed the smooth pink anus of the sixty-seven year-old man in his bed. Andrew spat into his hand then drooled between the cheeks. His fingers pressed the slime to the puckered anus then stroked his erect cock.

Whitney rose up to seemingly tower over her son. Her legs straddle his thighs as she grips his cock and presses it to her pussy. Teasing herself by rubbing his head against her wet folds and making Michael's cock throb. Lowering herself, she felt his thick cock push between her labia. Her eyes lock on her son's as she feels herself fully consume his erection. His hands reach up for her heavy breasts and she feels his hands grope. Her fat nipples throb and ache as his hands squeeze and release. Whitney begins to lift and descend on the thick cock.

Michael's face, on his back and watching his Mother ride his cock, breaks into a wide smile. He begins to push up as his Mother rides his cock. He feels alive at this moment. Her pussy is hot and wet and the squish of wet folds begins to fill the bedroom as they fuck.

In the next room, not more than twenty feet away, is a similar scene. Andrew lines up his cock to his father's asshole and presses. The ring expands and gives away to the fat head of his cock. Andrew puts his hands on his father's hips as he slowly begins to penetrate his asshole. Charles's head drops to the pillow as the familiar ache of being penetrated is felt from toes to nose. The wide mushroom head pops inside and Andrew rides his shaft inside the tight, sweaty asshole. His mound tickles the cheeks before burying himself completely.

Over his prostate, Andrew begins to fuck his Mother's chambermaid. Long, deep strokes at a measured rate. It's been a couple weeks since he's had sex and he can feel his heart beat a little quicker at the thought of draining his balls in his father's hole. Charles can feel his soft penis begin to leak as his body is continually stimulated by cock. Andrew's long, blonde hair tosses over his shoulders and chest as he strokes his cock in the tight asshole.

Panting, Andrew can feel his balls tighten as his orgasm nears. Charles knows his cheeks are pink with the embarrassment of being so aroused by taking cock. His son's cock in his hole. A soft cry slips from his lips as his anus clenches and cum dribbles from his penis filling his thong with sticky. The clench sets Andrew off and he cries out softly as well though his orgasm is strong and intense. His cock pounds into Charles and cum shoots deep into his father's rectum. Holding himself against his asscheeks until his balls have drained then he slips out and collapses on the bed.

Next door, Whitney is panting and her breasts are bouncing now as she rides her son's thick cock. Michael is squirming on the sheets under his Mother as she rides him. His balls ache then his cock erupts inside her. Whitney slams down hard on his groin and smiles as her orgasm shakes her body. She fills him gushing and squirting up inside her until she knows he is drained. Resting a moment then she slips from his cock and kisses him softly on the lips. She slips on her panty and exits as quietly as she entered.

Meeting Charles in the hallway, she slips her hand in his and walks quickly with clenched thighs to the bedroom. Quickly, she rolls onto her back and lifts her legs. "Your youngest son gifted you, my dear." Charles understands completely. Whitney motioned to the bureau for him to fetch a wig. He quickly chose a short, black-haired wig and quickly fastened to his bald scalp. Charles slipped the panty from her. Her vaginal lips are pink and slightly swollen from the ride. Her pussy is slick and glistens in the soft light. Between her thighs, he buries his face.

He could smell her strong pussy scent and that of a new man. His tongue lavishes her pussy with quick stabbing motions and long strokes. The taste of semen was strong as he cleans his wife's pussy as he has now done on hundreds of occasions. The wig made him feel better about himself and Whitney always likes him to look this way when he is not in trouble. With his ass up, he could feel Andrew's semen seep from him and run down is inner thighs.

The family is once again all under one roof. Yes, Michael's marriage is on the rocks and Andrew does not know where he will work or live, but those things will all work out in time. For now, the family is intact. Charles was the first to wake the following morning. Whitney had put him back in chastity before they fell asleep. He had made the mistake of telling her that Andrew called him the chambermaid. So this morning, that's how he dresses - as the maid.

Charles wears a short, dark-haired wig with simple white blouse and a black latex skirt that barely covers his asscheeks. He wears a bra with C-cup false boobs and two-inch black heels. Michael is first to wake., then Andrew and a bit later, Whitney. Charles has made cinnamon rolls and coffee before preparing breakfast for the family. If a stranger were to happen by, they would have no idea about the family dynamic or any of the happenings from the previous night.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
BrendaNWBrendaNW5 months ago

I prefer fun and love not so much submission, we'll written but not really my thing,

Share this Story

Similar Stories

Crossdressing Son and Dad Dad unknowingly fucks crossdressing Son.in Incest/Taboo
Initiation - Father - First Night Caught spying on Dad in the shower, I begin my initiation.in Incest/Taboo
Surprise Father and Son sex when Mom comes home early.in Incest/Taboo
Growing up as a Pastor's Son A preacher's son finds out the truth the hard way.in Gay Male
A Cum Factory for My Lil Bro Having a gay bro gives me and my big cock a big advantage.in Incest/Taboo
More Stories