Coming of Age
Copyright© 2026 by JackSpratt
Chapter 1
Erotica Sex Story: Chapter 1 - 14 year old Natalie is coming of age, watch as she and her mother fall prey to a 17 year old romeo with thoughts of indoctrination
Caution: This Erotica Sex Story contains strong sexual content, including mt/Fa ft/ft Fa/ft mt Blackmail Coercion Consensual Reluctant Fiction Sharing Mother Daughter Group Sex Anal Sex Analingus First Facial Oral Sex Petting Sex Toys Public Sex Small Breasts
Natalie Preston was a somewhat shy 14 year old girl, just beginning to transition into puberty. Her breasts were now substantially more than the mosquito bites she’d had for several years, 29A, just enough to measure and her mom had bought her the first bra she’d had since her training bra. Her period had recently shown itself and now she began to wonder about her body, spending time in the bath exploring her womanhood and the different pleasures she could show herself.
Her first orgasm that she brought upon herself had started innocently enough as she washed her vagina with the wash cloth, lingering over the little button she had found. That discovery had brought her much pleasure during bath time and sometimes late at night in her bed.
She lived with her mom, her dad had died in a car accident when she was just 10 years old, it had devastated her. Her mom had devoted herself to seeing to Natalie’s every need, her dad’s insurance had left them debt free. They had a nice house, in a nice neighborhood, a decent car and her mom helped her adjust to life without a father.
Karen Preston was a 32 year old woman, a much more developed version of her daughter. 34C breasts, a nice firm ass and a pretty face, framed with brunette locks, like Natalie. Karen worked part time, though they didn’t really need the money and she hated leaving Natalie alone. She had not dated since becoming a widow and basically kept to herself, looking after her daughter.
Unbeknownst to Karen, Natalie had obtained a boyfriend, a senior, 17 year old Jacob Andrews. Jacob was a virile young boy, who saw every girl as a conquest and he’d set his sights on Natalie. He was very well liked at school and all of Natalie’s girlfriends had told her how lucky she was and she felt that if she screwed up, they would willingly take her place.
Because she hadn’t told her mom about him, they sneaked around at first. They would meet in various empty rooms at school and there he began his conquest of her. He realized she was still a child, so he went easy on her. It was a month before she let him put his hand down her shirt and cup her small tits. In another two weeks, he had graduated to getting her off with his fingers in some dark area of the school, she loved how his fingers on her special button made her feel, but she had stopped him there.
She had gone home with him once, when her mom was working and his parents were gone too. He had persuaded her to get naked and managed to take a couple of pictures of her in the nude, he jerked off to those late at night. He too had stripped and saw the wonder in her eyes as she first laid eyes on an erect cock. He encouraged her to touch it and play with it, she reluctantly did so, but very shyly.
He laid a challenge before her, if she would kiss his cock, he would lick her pussy and if she thought fingering her little button felt good, his tongue on it would drive her nuts. She could just imagine what that would feel like, so she agreed, but told him no more, no fingers and definitely no cock inside of her. He arranged them in a 69 position with her on top and she hesitated to kiss his throbbing cock, until his fiery tongue landed on her button, her hips spasmed and she moaned.
Her pussy was on fire, his tongue knew all the right moves and before she knew it, not only did she kiss his cock, but the head was in her mouth and she sucked it like a hungry baby with a bottle. One, two, three orgasms and she had over half his cock in her mouth, oblivious to what would soon occur, sucking without even realizing it. She loved the way he made her feel, she never wanted it to end, but suddenly, as young boys do, his cock erupted in her mouth and she gagged and tried to spit it out, along with the slimy content it was depositing in her mouth.
His cum dribbled from her mouth, his cock steadily shooting more as she tried to breathe, unconsciously swallowing some of it. He renewed his assault on her clit and she burst forward with yet another orgasm, slickening his mouth with her own fluids. Natalie had experienced giving her first blow job, her friends had talked about it and had all said they swallowed it and she should do the same if it ever happened to her. They reminded her that they would be happy to have her boyfriend cum in their mouth and she had felt jealous.
Jacob had managed to get his cock back in her mouth as he ravaged her virgin pussy and she had reluctantly swallowed a good portion of his cum, a little salty, but not that bad. She did have it all over her face, when she had pulled off of it and he shot it all over her face and in her hair. As her last orgasm subsided and his deflating cock left her mouth, she rolled onto her side, panting.
“Damn that was hot, Baby! Your pussy tasted so good, I couldn’t help myself, but you swallowed like a true trooper, thanks Baby.”
Natalie felt somewhat embarrassed, but also in awe that he had called her baby. The ejaculate had been a surprise and somewhat nasty, but was not something she would refuse to do again. She had learned in sex ed class that oral sex would prevent pregnancy, as well as anal sex, but that was a disgusting thought. Jacob led her into his bathroom and they showered together, he paid a lot of attention to her little button, bringing her off yet again.
Natalie couldn’t believe she had been introduced to sex, albeit oral sex and when he pushed down on her shoulders in the shower, she took the initiative and rubbed his cock over her lips. She took him between her lips and tongued his peehole, feeling his cock grow in her hands and he slowly pumped it into her mouth. He was deliberately going slow, he didn’t want to scare her off, this was more than he had hoped for.
She got adventurous and began to take more of him in her mouth. She set up a rhythm, accepting more and more until he reached the back of her mouth and she hesitated, running her tongue around his shaft while in her mouth. He lunged forward and she gagged and spit him out, coughing. He apologized and she took him again, this time not letting him get so deep. He held both sides of her head and began to fuck her mouth, she tried her best to accommodate him, knowing he was much more experienced in these matters than her.
“Get ready to swallow, Baby. Just keep swallowing and don’t stop!”
A torrent filled her mouth and she struggled to swallow it all down, some of it seeping from the corners of her mouth, but she wanted to please him. When his orgasm stopped, he let go of her head and slid out from her mouth, a long string of cum connecting his cock to her mouth. The string finally got too long and it broke, dropping onto her pert tits, the shower soon washing it away.
They dressed and she headed home, trying to beat her mother home, but she had decided that she would tell her about Jacob. He had been a secret long enough and she wanted her mom to know he was a wonderful boy. She brushed her teeth when she got home, afraid her mom would smell his cum on her breath. She was proud of herself, she had taken the initiative and giver her first real blow job and it really wasn’t all that bad. She had gotten used to the taste and she kind of liked the feel of his cock in her mouth and on her tongue, she would try to do it more often, she wanted to make Jacob feel good. His tongue on her had felt terrific as well and she hoped there could be more of that.
When Karen got home, Natalie had started dinner already and they both sat and ate. Karen noticed a difference in Natalie, though she didn’t know exactly what had caused it. Natalie made small talk then she told her mother about Jacob, Karen was not happy that he was 17 and was concerned about the possibility that Natalie might become sexually active, but she tried to push her concerns aside, after all Natalie was happier than she’d ever seen her. They made plans for Karen to meet Jacob, he was invited for dinner Saturday night.
Karen couldn’t help but to think about Natalie and sex, lord knows she sure missed it, but her battery operated boyfriend got a workout that night. Natalie had heard her mother’s moans late at night, but never put it together. Her mom’s sex life never entered her mind, but her own had taken center stage, her hand found her button as she relived the afternoon and she bit her pillow as she orgasmed.
Saturday came and Karen decided to dress nicely, to make a good impression on Jacob, but little did she know that Jacob already had an excellent impression of her. He had always wondered what having a mother/daughter threesome would be like and he had begun making plans to find out. He had talked to a friend of his who had hooked him up with some roofies and he was going to have a pleasant Saturday night indeed. He told his parents that he was spending the night with Tony, his best friend, so that he could have a night of pleasure and fun. He tucked the roofies into his pocket as he told his parents good bye and left for Natalie’s.
He was not at all disappointed when he met Natalie’s mom, she was the grown up version of Natalie, 34C tits and a nice ass, he couldn’t wait to see her naked. They made small talk over dinner and when they weren’t looking, he dropped the roofies in their drinks. It took not quite an hour for the pills to work and he tested them by making some out of the ordinary requests of the two females. They kind of had blank stares and were somewhat out of it, but didn’t hesitate when he asked them to undress each other. Soon the older and younger versions of Natalie stood naked in front of him, eager to do his bidding.
He had Natalie give him a blow job while he had her mom go get her battery operated boyfriend and put on a show. He was unsure which one he wanted to fuck more, but being a teen, he knew he could cum multiple times, so both would get a work out. Natalie was getting better at giving blow jobs and he was soon near the popping off spot, but he made Karen take her place and as he had suspected, she was adept at deep throat as he unloaded straight down into her stomach. Natalie stood by, watching her mother take the load she had worked for as she fingered her erect button to orgasm.
Jacob had only had one girl who could deep throat him, because of his size and Karen had met his expectations, he would have to get her to teach Natalie. He questioned Karen about her sexual exploits to gauge what he could make them do. Karen had tried lesbian sex in college and was not against it, but she loved cock too much to become a devoted lesbian. Jacob learned that she hadn’t had sex in the four years since her husband’s death and he saw an opportunity to correct that.
He also elicited from Natalie that, as he had suspected, she was still cherry in two of her three holes, he had taken her oral cherry. He had Karen lay down on her back and had Natalie straddle her face and instructed her to pleasure her daughter while he pleasured her. Both females obeyed and Natalie was soon riding her mom’s face and Jacob moved between her outstretched thighs. He notice that both females had neatly trimmed landing strips over their pussies and he vowed that he would have them shave each other bare before the drug wore off.
Karen flinched when Jacob’s 8 inch cock connected with her labia, she had used her vibrator many times, but the real thing was always preferred in her mind. He rubbed himself up and down her labia, coating himself with her copious juices, before slowly inserting himself. Natalie squealed as her mother evidently concentrated on her button as Jacob slid inside fully. He grabbed two handfuls of Karen’s tits as he began to move in and out of her slickened pussy and leaned forward to capture one of Natalie’s pert nipples with his mouth, biting and chewing on the elastic nub. He tried to stave off the impending orgasm, but the mature pussy was too much for him, she controlled her inner muscles the way no girl ever had and he found himself shooting jet after jet into her waiting womb.
His orgasm triggered two others and soon everyone was in ecstasy in their threesome. As everyone began to come down, he slid out of Karen, watching some of his cum ooze out of her red, underused vagina and he saw Natalie slide off her mom’s face, leaving a slickened trail over her chin.
“Natalie, have you ever thought about eating another girl’s pussy?” he asked matter of factly.
“I did once at a sleepover. We got so excited that we paired up and ate each other, that’s why I liked it so much when you did me.”
“Come on over here and eat your mom’s pussy, clean all my cum out of her, you need to taste me again, I’m sure.”
She obediently got down between her mom’s thighs and licked the puddle of cum off the floor, then concentrated on its source, Karen was groaning in pleasure. Jacob offered his cock to Karen and she dutifully sucked it clean, causing another erection. Since Natalie had earned the last bonus of the blow job, but he had given it to her mother, Jacob gave this one to Natalie, she swallowed it hungrily. He told her not to swallow it all and to save some to share with mommy, which she did. It was wonderful watching a mother and daughter share my cum, this was going to be a wonderful relationship, he got out the movie camera and set it on the tripod, aimed at the adulterous gathering.
It was still early and he had a night full of sex planned and he wanted to capture Natalie’s deflowering on camera as well as his first taste of anal sex with Karen. He allowed a brief rest period, while he encouraged them to explore each other’s bodies, emboldened by the fact that this would definitely be a night to remember. He felt himself hardening just thinking about it, a 17 year old cock knew no boundaries and had many lives left for the night. He asked Karen about anal sex and she told him that her and her husband had found it quite erotic at times, but that vaginal sex had always won out. He asked her if she thought Natalie could handle it and to his surprise she answered in the affirmative, but added with adequate coaching and lubrication.
He decided that Natalie’s anus would wait for another session and set about herding the females into the shower and had them both bathe him, then each other, it’s a good thing he had a short reload time, because the two of them had ganged up on his cock and they had shared the load afterwards. He settled on the mother/daughter angle for awhile and videoed them pleasuring each other while he stroked his overworked cock and felt it grow again. Karen drooled, it had been so long since her teen years and the never ending male orgasms of youth.
Karen crawled over on hands and knees and took his cock into her mouth while she sucked on it, Natalie took up a position behind her mom and Jacob instructed her to eat her mom’s ass while finger fucking her, as the camera whirred on capturing all of the debauchery. His video was going to make the roofies no longer necessary as he blackmailed the two of them, once his cock was good and hard, he had Karen turn around and eat Natalie while he lined up with her slickened ass, Natalie had left plenty of saliva behind.
Even with Natalie’s spittle, he still had a tough time popping through her anal ring, but once he managed that, he quickly fed her his whole 8 inches pausing as his balls rested against her labia, Karen had never felt so full in her life, her husband had only been just under 6 inches, Jacob had surely filled her up. She worked her sphincter to massage his big cock and Jacob loved it, soon she was doing it as she pulled and pushed on the big invader. She reached back and fingered herself as the fullness of her back passage pushed her into an orgasm, clamping down on Jacobs cock and sending Natalie into her own orgasm with her mouth.
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