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Will woke up with a raging boner. After dreaming all night about having sex with Sarah, his hot classmate from college, he needed some relief. He looks at the clock and sees it is 4:52am. He wonders, Who is going to relieve him so early on a Saturday morning? Well, he can’t touch Valerie yet, Melanie is at a sleepover, Megan is still upset with him for some reason and Kelly would kill him if he woke her up this early. He arrived at the only person who would unconditionally relieve him of his sexual pain.
He got out of his bed. Out of his room, he passes the other three bedrooms and reaches the stairs. The house is quiet, nobody ever wakes up early on a Saturday in this house. He reaches the bottom of the stairs and quietly shuffles to the back of the house where the other two bedrooms are located. The one on the right, he won’t dare open at this hour in the morning but the one on the left, he knows that is where is sexual release will be. Will quietly opens the door and instinctively finds the side of the bed he’s looking for.
He softly shakes the figure on the bed. The figure moves but it doesn’t respond. “Mom, Mom.” He quietly whispers. This time the figure turns to face him and removes the sheet from her face. The face of a beautiful woman appears. Catherine is in her mid forties but still looks like she’s in her late twenties, messy raven black hair, hazel eyes and full lips. She tiredly looked at him and asked:
“W-What’s wrong, honey?”
He got closer to her and answered in a low voice, “I have a problem that needs taken care of.” He slowly took her hand as he said so and placed it on his hard cock.
Catherine gently rubbed her hand over his pants. “Don’t worry honey, I’ll take care of it.” While still resting on the bed, his mother deftly removed his pants and took his cock in her hand. She felt his cock throbbing in her hands as she slowly started jerking him off. He let out a sigh of relief as he felt his mother’s soft hands gently massaging his needy penis. “What would it be today, baby?” she asked in a very sexy tired voice.
“I only need a blowjob.” he said. He then felt his mother’s tongue on the tip of his dick. She’s rolling her tongue around his head tasting the precum that leaked from his dream with Sarah. Then, her full lips part, taking half her son’s cock into her mouth. She expertly sucks the head as she jerks and twists his shaft. Will loves to feel the wetness of his mother’s mouth, she’s always been the go to one for blowjobs. Will is trying real hard to hold his moans as his mother is freely making as many gag noises and moaning.
“Mom, you’re gonna wake up dad if you keep moaning.” He looks over to see his dad, sleeping and facing the other way. She pops his cock from her sexy mouth, “It’s okay honey, you know your father is a heavy sleeper, he wouldn’t wake up even if the house fell on him.” She then took his cock in her mouth and, as if to make him finally moan, she deep throated every inch of him. This finally broke Will’s silence as he let out a guttural moan. Catherine kept choking herself with his cock until she finally felt the familiar pulsating in her mouth.
“Mom, I’m gonna cum.” Catherine kept going at it all the while his cum rushed from his dick down to her throat. Will grabbed her head and hump it as his mom dutifully waited until he was all empty. His mother then took him out of her mouth and lick all that was left around his tip. Catherine swallowed what was left and gave his penis a gentle kiss. He leaned in and gave his mother a kiss on the lips, “Thank you, mom.” he said gratefully.
“You’re welcome, honey. Consider that a nice Happy Birthday morning blowjob.”
Soon he left the room and went upstairs to sleep for a few more hours. He wondered as he drift off what his parents have planned for him and his twin sister Megan birthday today.
It was Will and Megan’s Eighteenth birthday. Will woke up at 9am, ready to celebrate his birthday. His parents have been teasing him all week long about a special surprise they have for him. He is suddenly hit by the wonderful smell of breakfast being made. He walks first to his twin sister’s bedroom to wish her a happy birthday. He knocks but she doesn’t answer, so he opens the door and finds the room empty and her bed made. “That’s weird, she always sleeps late.” Will said. “Is she still mad at me?” he wonders.
Will makes it downstairs when he is greeted by his sister Valerie (She is six years younger than him.), who is sitting at the couch watching cartoons. “Happy Birthday!” she exclaims as she hugs her big brother. “Thank you, sis. Have you seen Megan?”
“Yes, she left early today, her boyfriend picked her up,” she says.
“Damn, then she really is mad at me. Our birthdays have always been special between us and for her to disregard it like that is not like her.” Will thought as he walked into the kitchen where his mom, Catherine, was finishing up cooking. After happy wishes and a little chit chat, the food was done. “Honey, go get your father and Kelly so they can come eat.” Will gets up and goes to Kelly’s room. Once he’s at the door, he hears moaning coming from the room. He quietly opens the door and peeks his head in. He sees Kelly in all fours on the bed, her huge tits rocking back and forth. She’s 24 years old the oldest sibling of five, long black hair, beautiful green eyes and a body to die for, just like her mother. “Oh fuck yes, harder… deeper.” Her upper body drops on the bed, making her ass curve upward, granting access to deeper parts of her pussy. The man behind her grabbed her by the hips, slamming her ass on to him. “Fuck, Fuck Fuuuuuck ahhh.” moaned Kelly as her orgasm rocked her body. Soon enough the man behind her was going to cum too.
“Where do you want my cum, princess?” asked the man.
Kelly got on her knees in front of the man. She was jerking his cock and aimed it at her face, “All over my face, dad.” Kelly hungrily jerked his cock until John exploded his jizz all over his beautiful daughter’s face. After witnessing the show, Will cleared his throat letting them know of his presence. “Mom says breakfast is ready.”
Soon after that Melanie (who is four years younger than Will) arrived from her sleepover and they all had breakfast together minus Megan. Mom and Dad spoke about the special gift they had Will for his birthday. It had to wait because Catherine wanted to set the mood and prepare the gift. So John decided to take his son Will on a boy’s day out until the time was right. Will was excited. What the hell could it be? He knew it wasn’t a new car because he has one, and he doesn’t lack of anything because his family is well off financially. Also, what could it be that they are only giving it to him and not Megan his twin sister?
All these questions turned his head as he was around town with his father until he received a message and told him: “It’s ready.”
They arrived home in the evening. When they went inside Will’s dad pointed upstairs: “In your room.” he said. Will sprinted up the stairs, excitedly got to the door, swung it open and he found … his mom. She was standing in the middle of the room smiling and then suddenly she moved aside to reveal his youngest sister, Valerie, that was right behind her. She was wearing a pink dress a big red ribbon on her head with a tag hanging from it that said: From: Mom & Dad To: Will.
“Ta Da.” Catherine said excitedly. “Here’s your gift, Your sister! Or to be more specific your sister’s virginity.”
Will was in shock. In Will’s family, there’s only one person who has a right to deflower Will’s sister’s virginity, his dad John. John took Kelly, Megan and Melanie’s virginities as soon as they had their first period. Kelly is 24 years old now but her virginity was taken in her first year as a teen. Megan’s was taken a year before being a teen and Melanie lost her virginity only two years ago. After dad takes their virginity, he has his daughter exclusively for a month to do what he wants with her before she’s given to the rest of the family. No one is to sexually touch or perform acts of sex on her, she is off limits until she gets her period and the month with their dad.
“I thought only dad could do that.” Will said confusedly.
“Well, you are right son.” His dad said behind him. He walks in the room and stands next to Will, putting an arm around his shoulder. “But, now that you are 18 years old you are a man, and what better way to celebrate that by now giving you the responsibility of deflowering your youngest sister.” He said proudly. “She will be sleeping with you here for the next month, so your job is to use her however you want and train her however you want.”
Will is ecstatic. He can’t believe he’s about to be his sister’s first. She’s such a pretty thing too, long auburn hair (Valerie, Will and Megan have their hair color from their father’s side), hazel eyes and an angelic face. Her body is slim, her skin light just like her mother, curves in development, small breasts and beautiful long legs. Although he’s fucked his sisters and his mom, Valerie has been one that he’s been praying for years to fuck. He even broke the rule once a year ago, when he secretly and quietly sneaked in to Valerie’s room when she was sleeping and masturbated next to her. He wanted to cum all over her face but he didn't risk it.
“So, son. Mom and I will leave you now to do what you have to do.” John and Catherine walked to the door and before he closed the door he said: “Have fun, son.”
Will found himself alone in his room with his sister. For a moment his mind went blank. Only when his sister spoke it snapped him back to the moment.
“So what do you want me to do?” Valerie asked shyly, bringing herself closer to Will.
“Take off your dress.” Valerie then awkwardly took off her dress and let it drop to the floor. She stood there wearing matching pink bra and panties. Her small curves and cutely shy face was making Will’s cock hard. Will got closer to her, slowly caressing her face bringing his hand down her neck to her curves and then resting it on her breast. They were tiny but still something to grab. He then slid his hand under her bra, massaging the tiny breast. With his other hand he took the back of her head and brought it forward, locking lips with her. They kissed as his hand slid down from her breast until he found her young pussy. She jumped a little but calmed down. Will was surprised that his sister was a good kisser, no doubt their mom coached Valerie in a few things. He found her clit and stimulated it: making her moan into his mouth. He slowly walked her to the bed as they embraced each other. Once next to the bed, Will gently sat Valerie down. He released his hand from her pussy unlocked lips with her.
He began to undo his pants to release his aching cock. Once it sprung out Valerie’s eyes went wide as it locked sight with his cock. “Mom taught you a little on how to handle a penis, right?” he asked. She nodded still her eyes transfixed on it. “Did she teach you how to suck it?”
“Yeah, she taught me how to do it.” she said.
“Good, you were taught by the best cocksucker in the house. Now grab it and show me what you have learned.”
Valerie did as she was told. She took a firm grip at the base as she took the tip of his cock into her tiny mouth. She rolled her tongue on his head inside her mouth as she firmly jerk his cock with her small hands. Slowly feeding inches into her mouth she sucked and bobbed on it. Will still couldn’t believe this was happening: the youngest of the house giving him a blowjob and being the first in there for a kick! She had half his cock in her mouth, she couldn’t deep throat just yet but she showed promise. She alternated from sucking to licking to stroking his cock as she took his balls in her mouth. She took each testicle and awkwardly but lovingly suck and licked them. Once done, she licked her way up the shaft until she had his tip in her mouth again. “Look up at me.” he ordered.
Her beautiful tiny face looked up at him: her lovely lips wrapped around him, little tears on her eyes. Her mouth was spectacular, small and tight, silky soft and wet. Her hands knew what they were doing, her fingers rolling the testicles as if trying to produce semen and the other feeding the shaft into her mouth. Will was in another world, his sister learned well on how to give oral pleasure. Now it is time for him to show her his gratitude.
“I’m going to cum in your mouth Valerie, it is time for you to learn how to swallow.” He took hold of her head and started to pump himself into her mouth. Valerie’s eyes rolled backwards as Will massively exploded in her mouth. She gagged and choked on his cum as it hit the back of her throat. When Will finally took out his dick Valerie coughed up cum but was able to swallow some out it. Will relaxed on the bed and patted the bed so Valerie could lay next to him. Valerie snuggled up so Will could wrap his arm and leg around her to spoon her.
Will and Valerie laid there spooning and in a few minutes Will finally started getting hard again. He started grinding his penis on Valerie’s ass and she responded by wiggling her ass back.
“You know what comes next, right?” he whispered into her ear.
“Y-Yes.” she quietly responded.
“Mom told you it will hurt, right?” he asked
“She said it will hurt but it will stop hurting and I’ll start liking it.” she said in a low voice, a little bit of doubt behind it.
“Well, don’t worry too much. Mom is right, it will hurt once I break your hymen but it will get better once your pussy adjusts to my penis. I will be gentle with you so just let me know when it hurts.”
While still spooning, Will takes off Valerie’s pretty panties off and slides his penis between Val’s thighs. He pumps in and out with one hand on her hips. Will moves his penis up to make contact with Val’s vulva. He keeps pumping between her legs grinding against her to make her wet. Slow and surely Valerie is starting to pant and she’s responding to his humping. He feels her wetness start to cover his cock.
“Are you ready?” he asks.
“Uh Huh.” Valerie says in short breathes.
Will lifts Valerie’s leg and takes his cock to find her vaginal opening. He presses his head to her opening, her vagina is small but it’s ready for its first time. He presses the tip in and Valerie groans. Will has to push a little harder and she winces and sucks in air.
“It hurts. Take it out.” she says, little tears forming in her eyes.
He takes it out and has to think of another approach. He thinks that If he goes slowly this will take all night until he finally gets it in. There’s only one way to do this and he feels very bad about doing it to her. But, he has to do it, it is his responsibility now to take his sister’s virginity, to train her to be a woman. He gets up and instructs her to lay on her back. He takes a pillow and places it underneath her to lift her bottom in a comfortable position. She looks so cute on her back, her beautiful hair splashed around her head, her beautiful eyes looking up timidly at her brother and her legs spread presenting her hairless pussy for her big brother to enjoy.
Will aligns his cock to her tiny entrance. This one is going to take a hard push. “Val, the only way we are going to do this is if I do it quick.”
“I’m scared.” she says tears rolling down her cheeks.
“Don’t worry, just suck in air and bite this pillow, it will pass. Count to three with me.”
“One.” Will takes his cock in one hand and the other places it on his sister’s waist.
“Two.” And before Valerie finishes saying it, Will’s cock invades her insides in a quick motion. He tears her hymen and his cock goes all the way. She lets out a high pitched noise like a wounded a****l. He has to keep pumping in and out of her so her pussy gets accustomed to his length. Valerie is very tight and she feels amazing, her young cunt squeezing Will’s cock into pleasure. He leans on her and embraces her for comfort. She’s crying and groaning through pillow covered clenched teeth. Will keeps going at her, whispering into her ear: “You are doing great, just hold on.”
Soon enough her crying subsided, and it seems that it was getting pleasurable for Valerie. She stopped groaning and the new sounds she was making were moans. Deep moans as she then started responding back to Will’s thrusts. He started going faster inside of her, feeling that soon enough he was going to cum. Her legs wrapped around his waist, inviting him even deeper into her. His virginal little sister was no more. He saw the potential his little sister had, just like her other sisters, to learn to become a woman able to sexually satisfy any man. Will was proud to be her first, to be her teacher and master for a month.
His sister’s back started to arch and her vaginal walls started to squeeze him harder. Valerie was having an orgasm. He started to ease up on his thrusts but she spoke up: “No… faster.”
Faster he went until she was done and soon enough he was cumming too. He released his semen deep inside her, cumming inside such a tight and wonderful pussy. Once they were done, they both laid in bed silent, taking deep breaths and recovering from that first fuck between them. Valerie kept her legs spread wide open, her genitals and insides in pain. Although it was painful for her, she admits to herself that it felt real good at the end. She finally is a woman, just like Catherine told her she will be once she flowered and was given to her big brother for him to pluck. She was always jealous of her big sisters and she begged her mom since she was younger for daddy to come and give her the gift of womanhood.
But Catherine always said no, it wasn’t her turn. She had to wait for Melanie to flower and then she would be next. She remembers the day Melanie flowered, how happy she had been and was rubbing it on Valerie’s face. That night, as is tradition, the daughter is showered and dressed and then Mom brings her to the parent’s room to be presented to the Dad. Once it is done, Mom would go to sleep to the daughter’s room or any other room in the house for a month while Dad taught his daughter everything she needed to know about sex.
When Melanie assumed that everyone else was sleeping in the house she snuck out of her room and quietly went downstairs to peep into her parent’s room. She saw the door ajar and light coming out of it. She tiptoed to the door and with one eye peeped in. What she saw gave her the tingles she didn’t quite yet understand in between her legs. Melanie was on all fours while her dad John was behind her, a tiny girl with such a massive man behind her, pounding away against her ass while tears streamed down her face. After that, she tiptoed back upstairs and heard some moans coming from her big brother’s room. She peeps again and finds her mother riding reverse cowgirl on top of Will, while Megan is sitting on his face getting her pussy eaten. Melanie pouts and goes to her room, jealous that everyone else gets to have fun and be an adult in the house except her. Later in bed, as she tries to go to sleep she discovers her clitoris and how pleasurable it is. After she’s done, she sleeps with a smile on her face.
After that day, she was next, which means now her mom has to give her lessons. Like her sisters before her, their mom Catherine gets them ready for sex. She explains the tradition, what their role is and what to expect, how sex works (without never breaking their hymen) and how to perform the best fellatio. After a year of this, Valerie was getting frustrated that she wasn't getting her period. So frustrated in fact, that one night she snuck into her parent’s room to see if her dad would finally make her a woman.
She got on the bed and started to pull on her father’s pants. She got them off and found her dad’s penis. She grabbed it and just as she was about to put to practice all that her mom taught her with her mouth, she felt a hand on her hair and pulled her back. Catherine scolded her.
“Why does it matter? We are going to do it anyway might as well do it now!” Valerie tried to reason with her mom.
“You don’t understand honey your virginity is for…” Catherine trailed off and never told Valerie. Two months ago, she finally had her period but the Big Night never came. Her mom told her to be quiet about it that they had something special coming up.
Now Valerie understood. Her virginity was for her brother. This is a rite of passage for women and an important day for her but also a very important day for her brother too. Today, He’s Eighteen years old which makes him a man and a man can only make a woman. Her thoughts disappear as she feels the hands of her brother on her body, caressing her tiny boobs, her butt and all the way down to her young cunt. Will mounts her again. This time she’s in all fours just like Melanie was that day but her vagina hurts less and as the night goes it hurts even less and starts to get more pleasurable.
As exhaustion took over them before they fell asleep Will said: “Today you learned a lot about two types of sex, Oral sex and vaginal sex but we didn’t get to one today.” he said with a huge yawn followed.
“Which one?” Valerie was curious, she didn’t know there could be another type of sex.
“Wait, Mom didn’t tell you about anal sex?” Will was surprised.
“What’s anal sex?”
Will laughed internally. He won’t explain it now, it would be much more fun to explain it tomorrow morning and look at her dumbfounded face.
“It’s nothing much, I’ll explain it tomorrow. Let’s sleep, I’m tired.”
They cuddled up and soon fell asleep.
He got out of his bed. Out of his room, he passes the other three bedrooms and reaches the stairs. The house is quiet, nobody ever wakes up early on a Saturday in this house. He reaches the bottom of the stairs and quietly shuffles to the back of the house where the other two bedrooms are located. The one on the right, he won’t dare open at this hour in the morning but the one on the left, he knows that is where is sexual release will be. Will quietly opens the door and instinctively finds the side of the bed he’s looking for.
He softly shakes the figure on the bed. The figure moves but it doesn’t respond. “Mom, Mom.” He quietly whispers. This time the figure turns to face him and removes the sheet from her face. The face of a beautiful woman appears. Catherine is in her mid forties but still looks like she’s in her late twenties, messy raven black hair, hazel eyes and full lips. She tiredly looked at him and asked:
“W-What’s wrong, honey?”
He got closer to her and answered in a low voice, “I have a problem that needs taken care of.” He slowly took her hand as he said so and placed it on his hard cock.
Catherine gently rubbed her hand over his pants. “Don’t worry honey, I’ll take care of it.” While still resting on the bed, his mother deftly removed his pants and took his cock in her hand. She felt his cock throbbing in her hands as she slowly started jerking him off. He let out a sigh of relief as he felt his mother’s soft hands gently massaging his needy penis. “What would it be today, baby?” she asked in a very sexy tired voice.
“I only need a blowjob.” he said. He then felt his mother’s tongue on the tip of his dick. She’s rolling her tongue around his head tasting the precum that leaked from his dream with Sarah. Then, her full lips part, taking half her son’s cock into her mouth. She expertly sucks the head as she jerks and twists his shaft. Will loves to feel the wetness of his mother’s mouth, she’s always been the go to one for blowjobs. Will is trying real hard to hold his moans as his mother is freely making as many gag noises and moaning.
“Mom, you’re gonna wake up dad if you keep moaning.” He looks over to see his dad, sleeping and facing the other way. She pops his cock from her sexy mouth, “It’s okay honey, you know your father is a heavy sleeper, he wouldn’t wake up even if the house fell on him.” She then took his cock in her mouth and, as if to make him finally moan, she deep throated every inch of him. This finally broke Will’s silence as he let out a guttural moan. Catherine kept choking herself with his cock until she finally felt the familiar pulsating in her mouth.
“Mom, I’m gonna cum.” Catherine kept going at it all the while his cum rushed from his dick down to her throat. Will grabbed her head and hump it as his mom dutifully waited until he was all empty. His mother then took him out of her mouth and lick all that was left around his tip. Catherine swallowed what was left and gave his penis a gentle kiss. He leaned in and gave his mother a kiss on the lips, “Thank you, mom.” he said gratefully.
“You’re welcome, honey. Consider that a nice Happy Birthday morning blowjob.”
Soon he left the room and went upstairs to sleep for a few more hours. He wondered as he drift off what his parents have planned for him and his twin sister Megan birthday today.
It was Will and Megan’s Eighteenth birthday. Will woke up at 9am, ready to celebrate his birthday. His parents have been teasing him all week long about a special surprise they have for him. He is suddenly hit by the wonderful smell of breakfast being made. He walks first to his twin sister’s bedroom to wish her a happy birthday. He knocks but she doesn’t answer, so he opens the door and finds the room empty and her bed made. “That’s weird, she always sleeps late.” Will said. “Is she still mad at me?” he wonders.
Will makes it downstairs when he is greeted by his sister Valerie (She is six years younger than him.), who is sitting at the couch watching cartoons. “Happy Birthday!” she exclaims as she hugs her big brother. “Thank you, sis. Have you seen Megan?”
“Yes, she left early today, her boyfriend picked her up,” she says.
“Damn, then she really is mad at me. Our birthdays have always been special between us and for her to disregard it like that is not like her.” Will thought as he walked into the kitchen where his mom, Catherine, was finishing up cooking. After happy wishes and a little chit chat, the food was done. “Honey, go get your father and Kelly so they can come eat.” Will gets up and goes to Kelly’s room. Once he’s at the door, he hears moaning coming from the room. He quietly opens the door and peeks his head in. He sees Kelly in all fours on the bed, her huge tits rocking back and forth. She’s 24 years old the oldest sibling of five, long black hair, beautiful green eyes and a body to die for, just like her mother. “Oh fuck yes, harder… deeper.” Her upper body drops on the bed, making her ass curve upward, granting access to deeper parts of her pussy. The man behind her grabbed her by the hips, slamming her ass on to him. “Fuck, Fuck Fuuuuuck ahhh.” moaned Kelly as her orgasm rocked her body. Soon enough the man behind her was going to cum too.
“Where do you want my cum, princess?” asked the man.
Kelly got on her knees in front of the man. She was jerking his cock and aimed it at her face, “All over my face, dad.” Kelly hungrily jerked his cock until John exploded his jizz all over his beautiful daughter’s face. After witnessing the show, Will cleared his throat letting them know of his presence. “Mom says breakfast is ready.”
Soon after that Melanie (who is four years younger than Will) arrived from her sleepover and they all had breakfast together minus Megan. Mom and Dad spoke about the special gift they had Will for his birthday. It had to wait because Catherine wanted to set the mood and prepare the gift. So John decided to take his son Will on a boy’s day out until the time was right. Will was excited. What the hell could it be? He knew it wasn’t a new car because he has one, and he doesn’t lack of anything because his family is well off financially. Also, what could it be that they are only giving it to him and not Megan his twin sister?
All these questions turned his head as he was around town with his father until he received a message and told him: “It’s ready.”
They arrived home in the evening. When they went inside Will’s dad pointed upstairs: “In your room.” he said. Will sprinted up the stairs, excitedly got to the door, swung it open and he found … his mom. She was standing in the middle of the room smiling and then suddenly she moved aside to reveal his youngest sister, Valerie, that was right behind her. She was wearing a pink dress a big red ribbon on her head with a tag hanging from it that said: From: Mom & Dad To: Will.
“Ta Da.” Catherine said excitedly. “Here’s your gift, Your sister! Or to be more specific your sister’s virginity.”
Will was in shock. In Will’s family, there’s only one person who has a right to deflower Will’s sister’s virginity, his dad John. John took Kelly, Megan and Melanie’s virginities as soon as they had their first period. Kelly is 24 years old now but her virginity was taken in her first year as a teen. Megan’s was taken a year before being a teen and Melanie lost her virginity only two years ago. After dad takes their virginity, he has his daughter exclusively for a month to do what he wants with her before she’s given to the rest of the family. No one is to sexually touch or perform acts of sex on her, she is off limits until she gets her period and the month with their dad.
“I thought only dad could do that.” Will said confusedly.
“Well, you are right son.” His dad said behind him. He walks in the room and stands next to Will, putting an arm around his shoulder. “But, now that you are 18 years old you are a man, and what better way to celebrate that by now giving you the responsibility of deflowering your youngest sister.” He said proudly. “She will be sleeping with you here for the next month, so your job is to use her however you want and train her however you want.”
Will is ecstatic. He can’t believe he’s about to be his sister’s first. She’s such a pretty thing too, long auburn hair (Valerie, Will and Megan have their hair color from their father’s side), hazel eyes and an angelic face. Her body is slim, her skin light just like her mother, curves in development, small breasts and beautiful long legs. Although he’s fucked his sisters and his mom, Valerie has been one that he’s been praying for years to fuck. He even broke the rule once a year ago, when he secretly and quietly sneaked in to Valerie’s room when she was sleeping and masturbated next to her. He wanted to cum all over her face but he didn't risk it.
“So, son. Mom and I will leave you now to do what you have to do.” John and Catherine walked to the door and before he closed the door he said: “Have fun, son.”
Will found himself alone in his room with his sister. For a moment his mind went blank. Only when his sister spoke it snapped him back to the moment.
“So what do you want me to do?” Valerie asked shyly, bringing herself closer to Will.
“Take off your dress.” Valerie then awkwardly took off her dress and let it drop to the floor. She stood there wearing matching pink bra and panties. Her small curves and cutely shy face was making Will’s cock hard. Will got closer to her, slowly caressing her face bringing his hand down her neck to her curves and then resting it on her breast. They were tiny but still something to grab. He then slid his hand under her bra, massaging the tiny breast. With his other hand he took the back of her head and brought it forward, locking lips with her. They kissed as his hand slid down from her breast until he found her young pussy. She jumped a little but calmed down. Will was surprised that his sister was a good kisser, no doubt their mom coached Valerie in a few things. He found her clit and stimulated it: making her moan into his mouth. He slowly walked her to the bed as they embraced each other. Once next to the bed, Will gently sat Valerie down. He released his hand from her pussy unlocked lips with her.
He began to undo his pants to release his aching cock. Once it sprung out Valerie’s eyes went wide as it locked sight with his cock. “Mom taught you a little on how to handle a penis, right?” he asked. She nodded still her eyes transfixed on it. “Did she teach you how to suck it?”
“Yeah, she taught me how to do it.” she said.
“Good, you were taught by the best cocksucker in the house. Now grab it and show me what you have learned.”
Valerie did as she was told. She took a firm grip at the base as she took the tip of his cock into her tiny mouth. She rolled her tongue on his head inside her mouth as she firmly jerk his cock with her small hands. Slowly feeding inches into her mouth she sucked and bobbed on it. Will still couldn’t believe this was happening: the youngest of the house giving him a blowjob and being the first in there for a kick! She had half his cock in her mouth, she couldn’t deep throat just yet but she showed promise. She alternated from sucking to licking to stroking his cock as she took his balls in her mouth. She took each testicle and awkwardly but lovingly suck and licked them. Once done, she licked her way up the shaft until she had his tip in her mouth again. “Look up at me.” he ordered.
Her beautiful tiny face looked up at him: her lovely lips wrapped around him, little tears on her eyes. Her mouth was spectacular, small and tight, silky soft and wet. Her hands knew what they were doing, her fingers rolling the testicles as if trying to produce semen and the other feeding the shaft into her mouth. Will was in another world, his sister learned well on how to give oral pleasure. Now it is time for him to show her his gratitude.
“I’m going to cum in your mouth Valerie, it is time for you to learn how to swallow.” He took hold of her head and started to pump himself into her mouth. Valerie’s eyes rolled backwards as Will massively exploded in her mouth. She gagged and choked on his cum as it hit the back of her throat. When Will finally took out his dick Valerie coughed up cum but was able to swallow some out it. Will relaxed on the bed and patted the bed so Valerie could lay next to him. Valerie snuggled up so Will could wrap his arm and leg around her to spoon her.
Will and Valerie laid there spooning and in a few minutes Will finally started getting hard again. He started grinding his penis on Valerie’s ass and she responded by wiggling her ass back.
“You know what comes next, right?” he whispered into her ear.
“Y-Yes.” she quietly responded.
“Mom told you it will hurt, right?” he asked
“She said it will hurt but it will stop hurting and I’ll start liking it.” she said in a low voice, a little bit of doubt behind it.
“Well, don’t worry too much. Mom is right, it will hurt once I break your hymen but it will get better once your pussy adjusts to my penis. I will be gentle with you so just let me know when it hurts.”
While still spooning, Will takes off Valerie’s pretty panties off and slides his penis between Val’s thighs. He pumps in and out with one hand on her hips. Will moves his penis up to make contact with Val’s vulva. He keeps pumping between her legs grinding against her to make her wet. Slow and surely Valerie is starting to pant and she’s responding to his humping. He feels her wetness start to cover his cock.
“Are you ready?” he asks.
“Uh Huh.” Valerie says in short breathes.
Will lifts Valerie’s leg and takes his cock to find her vaginal opening. He presses his head to her opening, her vagina is small but it’s ready for its first time. He presses the tip in and Valerie groans. Will has to push a little harder and she winces and sucks in air.
“It hurts. Take it out.” she says, little tears forming in her eyes.
He takes it out and has to think of another approach. He thinks that If he goes slowly this will take all night until he finally gets it in. There’s only one way to do this and he feels very bad about doing it to her. But, he has to do it, it is his responsibility now to take his sister’s virginity, to train her to be a woman. He gets up and instructs her to lay on her back. He takes a pillow and places it underneath her to lift her bottom in a comfortable position. She looks so cute on her back, her beautiful hair splashed around her head, her beautiful eyes looking up timidly at her brother and her legs spread presenting her hairless pussy for her big brother to enjoy.
Will aligns his cock to her tiny entrance. This one is going to take a hard push. “Val, the only way we are going to do this is if I do it quick.”
“I’m scared.” she says tears rolling down her cheeks.
“Don’t worry, just suck in air and bite this pillow, it will pass. Count to three with me.”
“One.” Will takes his cock in one hand and the other places it on his sister’s waist.
“Two.” And before Valerie finishes saying it, Will’s cock invades her insides in a quick motion. He tears her hymen and his cock goes all the way. She lets out a high pitched noise like a wounded a****l. He has to keep pumping in and out of her so her pussy gets accustomed to his length. Valerie is very tight and she feels amazing, her young cunt squeezing Will’s cock into pleasure. He leans on her and embraces her for comfort. She’s crying and groaning through pillow covered clenched teeth. Will keeps going at her, whispering into her ear: “You are doing great, just hold on.”
Soon enough her crying subsided, and it seems that it was getting pleasurable for Valerie. She stopped groaning and the new sounds she was making were moans. Deep moans as she then started responding back to Will’s thrusts. He started going faster inside of her, feeling that soon enough he was going to cum. Her legs wrapped around his waist, inviting him even deeper into her. His virginal little sister was no more. He saw the potential his little sister had, just like her other sisters, to learn to become a woman able to sexually satisfy any man. Will was proud to be her first, to be her teacher and master for a month.
His sister’s back started to arch and her vaginal walls started to squeeze him harder. Valerie was having an orgasm. He started to ease up on his thrusts but she spoke up: “No… faster.”
Faster he went until she was done and soon enough he was cumming too. He released his semen deep inside her, cumming inside such a tight and wonderful pussy. Once they were done, they both laid in bed silent, taking deep breaths and recovering from that first fuck between them. Valerie kept her legs spread wide open, her genitals and insides in pain. Although it was painful for her, she admits to herself that it felt real good at the end. She finally is a woman, just like Catherine told her she will be once she flowered and was given to her big brother for him to pluck. She was always jealous of her big sisters and she begged her mom since she was younger for daddy to come and give her the gift of womanhood.
But Catherine always said no, it wasn’t her turn. She had to wait for Melanie to flower and then she would be next. She remembers the day Melanie flowered, how happy she had been and was rubbing it on Valerie’s face. That night, as is tradition, the daughter is showered and dressed and then Mom brings her to the parent’s room to be presented to the Dad. Once it is done, Mom would go to sleep to the daughter’s room or any other room in the house for a month while Dad taught his daughter everything she needed to know about sex.
When Melanie assumed that everyone else was sleeping in the house she snuck out of her room and quietly went downstairs to peep into her parent’s room. She saw the door ajar and light coming out of it. She tiptoed to the door and with one eye peeped in. What she saw gave her the tingles she didn’t quite yet understand in between her legs. Melanie was on all fours while her dad John was behind her, a tiny girl with such a massive man behind her, pounding away against her ass while tears streamed down her face. After that, she tiptoed back upstairs and heard some moans coming from her big brother’s room. She peeps again and finds her mother riding reverse cowgirl on top of Will, while Megan is sitting on his face getting her pussy eaten. Melanie pouts and goes to her room, jealous that everyone else gets to have fun and be an adult in the house except her. Later in bed, as she tries to go to sleep she discovers her clitoris and how pleasurable it is. After she’s done, she sleeps with a smile on her face.
After that day, she was next, which means now her mom has to give her lessons. Like her sisters before her, their mom Catherine gets them ready for sex. She explains the tradition, what their role is and what to expect, how sex works (without never breaking their hymen) and how to perform the best fellatio. After a year of this, Valerie was getting frustrated that she wasn't getting her period. So frustrated in fact, that one night she snuck into her parent’s room to see if her dad would finally make her a woman.
She got on the bed and started to pull on her father’s pants. She got them off and found her dad’s penis. She grabbed it and just as she was about to put to practice all that her mom taught her with her mouth, she felt a hand on her hair and pulled her back. Catherine scolded her.
“Why does it matter? We are going to do it anyway might as well do it now!” Valerie tried to reason with her mom.
“You don’t understand honey your virginity is for…” Catherine trailed off and never told Valerie. Two months ago, she finally had her period but the Big Night never came. Her mom told her to be quiet about it that they had something special coming up.
Now Valerie understood. Her virginity was for her brother. This is a rite of passage for women and an important day for her but also a very important day for her brother too. Today, He’s Eighteen years old which makes him a man and a man can only make a woman. Her thoughts disappear as she feels the hands of her brother on her body, caressing her tiny boobs, her butt and all the way down to her young cunt. Will mounts her again. This time she’s in all fours just like Melanie was that day but her vagina hurts less and as the night goes it hurts even less and starts to get more pleasurable.
As exhaustion took over them before they fell asleep Will said: “Today you learned a lot about two types of sex, Oral sex and vaginal sex but we didn’t get to one today.” he said with a huge yawn followed.
“Which one?” Valerie was curious, she didn’t know there could be another type of sex.
“Wait, Mom didn’t tell you about anal sex?” Will was surprised.
“What’s anal sex?”
Will laughed internally. He won’t explain it now, it would be much more fun to explain it tomorrow morning and look at her dumbfounded face.
“It’s nothing much, I’ll explain it tomorrow. Let’s sleep, I’m tired.”
They cuddled up and soon fell asleep.
Stevie
- 02.07.2020
- 8
- 0
