Jenifer Comes of Age Ch. 01

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Şub 23, 2021 // By:analsex // No Comment

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Author’s Note: This story contains group sex, and both female and male bisexual sex.
I’d like to thank my editor, 69writer, for his expert editing and advice.

Jenifer has always been a nymphomaniac, as a little girl she was always touching herself between her legs. Jenifer’s mother was constantly scolding her and tried in vain to instill some moral values with lectures of lady like behavior, and stories of wayward girls and the subsequent trouble they’d get into.

As Jenifer grew into her teen years she fell in love with masturbation, she spent a lot of time masturbating. She was precocious enough to understand social norms, but lusty enough to not stop masturbating every chance she could; she was aware she needed to hide her pleasure seeking ways. Jenifer’s mother knew though, she could hear Jenifer’s moans emanating from her bedroom after school and even late at night. Jen’s mom was so concerned she put her on birth control at the age of 17, even before Jen lost her virginity. Jen’s mom was conflicted about the birth control. She didn’t want to send her the wrong message, that she was condoning teenage sex but the idea of Jen having an unwanted pregnancy to deal with scared her even more.

Jen turned 18 a few weeks before the end of her senior year in high school. Jen was still a virgin, she had been in no hurry to lose her virginity since she was so in love with masturbating. She took care of her own needs sexually. Her mother’s constant pressure on her to be lady like added to her reluctance to experiment sexually with her boyfriend.

By the time of Jen’s 18th birthday she was growing into a beautiful young woman. Jen wasn’t a classic beauty, she’d be no model, her body was a knockout, but her face was more Plain Jane, girl next store; pretty, but not shockingly so. She was about 5′ 5” tall, thin, but shapely. Jen had red hair, not bright red, more stubble, a mix of strawberry blond and auburn. Her skin was smooth, silky, and creamy white, not as pale as some redheads. She had light freckles on her face that were barely visible, just enough to add a shadowing effect that gave her skin depth. Her light cute freckles disappeared on her skin through her neck and into her chest, yet the rest of her skin was creamy white. Her breasts were 34Cs and perfectly proportioned to her body, full and round with just a hint of breast swagger to them. She has large, light reddish brown almost translucent areola, not so large they detracted from the rest of her breasts, but big enough to make a presence. Jen’s waist was narrow and shapely, with just the right mix of muscle tone and roundness. Her ass was toned, shapely, but full. Her pubic hair matched her head hair color, but a little lighter and wispy thin as she had a trim, natural bikini line.

Turning 18, Jen started thinking of losing her virginity. A lot of the girls she knew in high school had already lost theirs and she didn’t want to go to college in the fall a virgin.

Jen had been dating a boy in high school, whose name was Brad, also 18, and still a virgin himself. Not because he wanted to wait, he didn’t. He was shy and hadn’t had many girlfriends in school. Jen thought he was cute, so she initiated the friendship. The friendship grew into more, soon they were kissing. From then on they were going together. Brad pressured Jen for sex, but respected her wanting to wait.

Jen’s senior year was over, the graduation ceremony had come and gone, her last summer before college had started. Jen was scheduled to take a three week residential summer program at a local university, some prep for college course her mother had signed her up for. She only had two weeks off before that summer program began. She’d be gone three weeks, then she was to work in a dress shop in town for the remainder of the summer before heading off to college. Jen decided she would lose her virginity during the two weeks before she attended the summer program.

Jen was already on the pill and once her mind decided to go for it, she wasted no time getting Brad up into her bedroom. There in her bedroom, one warm early summer afternoon, both Jen and Brad had their first time together. Jen’s first time with Brad was lovely, despite claims from friends to the contrary: that your first time would be painful, you would be emotionally confused, etc. Jen loved sex so much; she embraced her first fuck like a seasoned pro. Except for a little blood, she loved it and came hard with Brad. Jen was so turned on she begged Brad to do it again. He needed a little time to recover, so Jen masturbated to 3 orgasms right in front of him. Brad didn’t know what to make of this, he loved the fact that they just lost their virginity together, but she was looking pretty wild and slutty at this moment. This scared him.

The time for the three week summer program had arrived. In the two preceding weeks Jen and Brad made love everyday they could get away alone together. Jen was really going to miss Brad these next three weeks, of course she had her own hands to satisfy her needs. casino şirketleri The program was set up to be just like college life, Jen stayed in a dorm, she shared the dorm with another girl in the same program. Jen’s roommate’s name was Sally, a thin plain looking girl with brown hair, small breasts, but pretty eyes and a beautiful smile.

Without Brad, Jen’s hands were busy between her legs, but Jen was concerned about keeping her masturbation sessions private. She became keenly aware of Sally’s schedule so she could get some alone time without getting caught with her hands in the pussy. Jen also needed to be vary discrete at night under the covers, muffling her moans was hard for Jen, but she bit her lips and held them in.

One day, only 3 days into her time at the summer program, Jen knew Sally would be at going for a run after school, so she went right back to her room and stripped naked. Jen was real horny that day and wasted no time fingering her pussy to orgasm. Jen was working on her second orgasm when the door opened, the door she forgot to lock! Sally, having skipped running because she sprained her ankle on the way to the track, got quite a sight as Jen, spread out naked on her bed, legs wide, one hand with three fingers deep in her pussy, the other hand working her clit. Jen never masturbated in front of anyone before, but when she saw Sally staring at her, she couldn’t stop. She was so turned on she just kept working her pussy.

What Jen didn’t know, Sally was a lesbian. Sally hadn’t talked about her sexual orientation to Jen. The subject never came up, in fact Jen hadn’t talked about sex at all with Sally, and she thought Sally was a bit of a prude. Sally, a little stunned, just looked on with what was at first shock, slowly turning into pleasure. Sally was getting more and more turned on watching Jen masturbate in front of her. Sally felt her loins burning with desire as she slowly let a hand move to her groin and started to massage her clit through her jeans. Jen, already on fire with passion, seeing Sally fingering herself just added fuel to her fire. Jen was riding an orgasmic high that kept ascending higher and higher, she didn’t say a word to Sally, just kept working her pussy and cumming and cumming, one wave after another. Sally sensed this and decided if she was going to get in on this she would need to make the first move. Sally herself rising to orgasm, quickly lowered her jeans and panties to her knees, not wanting to waste time removing her cloths and lose her rhythm, she quickly moved her hand to her now exposed pussy and lavished herself with her right hand. Jen and Sally looking intently at each other as they watched the other pleasure themselves. Sally’s left hand reached up under her blouse and was tweaking her left nipple as she brought herself to her first orgasm that day.

Jen was still riding her wave and could not stop no matter what. Sally, relaxing a little after her first orgasm removed her cloths and climbed on the bed with Jen. Sally moved between her roommates legs and licked her way up Jen’s left leg and then down the right one, stopping at Jen’s right foot to suck her toes for a while. Jen could not protest if she wanted to, Jen’s own mother could have walked into that room at that moment and Jen would have been helpless to stop masturbating, she was possessed. Sally licked her way back up Jen’s right leg and right up to the action happening at Jen’s snatch. Jen just kept rubbing her clit with her right hand and diving her left hand into her pussy while staring lustfully at Sally. Sally grabbed Jen’s right hand and moved it away from Jen’s clit, replacing Jen’s hand with her mouth she began tonguing her roommate’s clit. Jen never had another girl eat her pussy before, she had never been naked in the same bed with another girl before, she never gave it any thought really, she had always masturbated for the physical pleasure of it, when she did fantasize, and she mostly fantasized about Brad.

Jen was experiencing new sensations and she loved it. Brad, being new to love making, had not bothered to go down on Jen yet. Sally’s tongue was the first tongue Jen ever felt on her pussy and she loved it. It was warm, wet and alive with movement, and she didn’t have to orchestrate the action herself. Jen relaxed her left hand as she soaked up this new sensation and her fingers fell out of her pussy and grabbed Sally’s head and started stroking her hair. Sally sensed this and moved her right hand and 3 fingers into Jen’s vagina while lapping her clit with her tongue. Jen was approaching orgasm again, but this time it was different. This wave was deeper and stronger than the others she had worked up with her own hand, she was in total bliss as she rode out the best orgasm she had ever experienced. Jen even squirted a little, which she had never done by her own hand. As Jen came down off her sexual high she just shuddered and bucked while Sally administered more mouth to pussy resuscitation.

Finally Jen had to push Sally away from her pussy, she was too sensitive casino firmaları down there for any more stimulation. Sally kissed her way up Jen’s body, stopping at her breasts to suckle on each nipple before making her way up to Jen’s mouth. The two girls locked in a loving mouth embrace, lips and tongues mingled together for what seemed like an eternity. Jen was in another world, an out of body experience, as she came back to reality, she realized Sally needed a tongue on her pussy. Jen didn’t need any instruction, just has she had instinctively known how to enjoy her first fuck with Brad, she knew how to pleasure another woman , she was born for sex, it was part of her DNA, much to her mother’s chagrin. Jen moved slowly down Sally’s body wanting to savor the tastes and sensations on her tongue, she licked and kissed the nape of Sally’s neck, her shoulders, down her arm, over to Sally’s breasts, there she lingered for a long time. Jen’s first suckle of a breast since she was breast feed by her mother as an infant. Jen loved licking Sally’s aureole and sucking her nipples, she had a spontaneous, hands off, orgasm while sucking on her roommate’s breasts. Jen moved down to Sally’s belly button and stuck her tongue in and lapped at Sally’s indie. As she licked the skin around Sally’s belly, she moved a hand down to her roommate’s pussy and felt for the first time another woman’s folds of desire.

She played with Sally’s wet pussy for a seemed like an hour as she licked and smelled her new lover’s loins region. Jen’s tongue gave Sally a tongue bath all around her groin, her belly, her legs, her mound, all the while inhaling the smells, feeling the warmth emanating from Sally’s loins. Finally Jen reached Sally’s pussy with her mouth, she lapped and lapped at her new lovers beautiful pussy lips, diving her tongue in and out with abandon. She moved her tongue onto Sally’s clit and twirling and licking. Sally bucked and moaned as Jen lapped and licked. Jen shoved a finger into Sally’s love canal, then two and then three and groped for Sally’s magic spot. This is one place Jen’s instincts had no clue, where was Sally’s g-spot? It didn’t matter, Sally was too far gone to care if Jen hit her g-spot or not, she was riding high on orgasmic bliss, she was close to going over the top and she loved what Jen was doing to her. Jen began licking all the way up and down Sally’s pussy, from her clit to her vagina in fast forceful strokes with her tongue. Sally came like she was possessed, bucking wildly under Jen’s tongue.

Jen and Sally experienced many more sessions during Jen’s time at the university three week summer program. Both knew it was not a long term thing, Jen had Brad to go home to and Sally being a lesbian, it wouldn’t work; but they were female-female fuck buddies for those three weeks, and Jen loved being with another women – she vowed to always have a female lover on the side from here on out.

The three weeks were up and Jen and Sally went their separate ways. Jen came home and picked up where she left off with Brad. As the summer went on, Brad became increasing concerned with the level of Jen’s sex drive. Brad was content to have intercourse with Jen only once every time they got together, that is, if they could get alone. Jenifer, on the other hand wanted Brad to do it several times during their lovemaking sessions, and she would often masturbate in front of Brad, before, during, and after he made love to her. Sometimes he would catch her with her hand in her twat, whether it was in the car when he was driving her somewhere, or just sitting around the house. Brad was starting to think Jen was too much for him, and not of life partner material for him. He was thinking of breaking up with Jen when they both went away to college, this would give him freedom to date other girls, something he had been thinking a lot about anyway.

Jenifer also had wanderlust, she was thinking a lot about her time with Sally, and she was starting to get hungry for pussy. Jen also knew Brad was too boring in the bedroom for her; he always looked at her disapprovingly when she masturbated in front of him; that would never do. Masturbation was part of Jen’s life, she didn’t feel ashamed about it, she loved it; she couldn’t understand why everyone was so freaked out about showing off or touching their own bodies.

As the summer was went on the subject of splitting up when they went off to school was broached finally by Brad. Jen was relieved he brought it up and agreed it was for the best. Brad was happy they were both on the same wave length, he didn’t want a sob fest, now he could just think of Jen as a friend with benefits and enjoy the last of the summer before college.

Jenifer seduces her boss –

The summer was winding down and Jenifer would be off to college in a few weeks, it was a beautiful summer day today, clear, not too hot, perfect humidity. Jen was scheduled to work at the dress shop, she wanted the day off though, since it was going to be such a gorgeous day. She called up Lisa, the shop owner, güvenilir casino and asked for the day off. Lisa told her she needed her for at least the morning, she needed to run some paper work over to the accountant’s office and needed Jen to mind the shop. Jen didn’t have any plans anyway so she said she would come in for the morning and started to get dressed. Jen put on a short summer dress, she was feeling a little free spirited today, so she decided to go without panties on. She loved the feeling of the warm summer air wafting up under her dress caressing her pussy as she walked the mile from her house to the dress shop. Jen preferred walking to the dress shop on nice days like this. With her pussy free to the wind gently blowing up under her dress she was getting hornier with every step.

When she walked into the shop her boss greeted her with a big smile, “Sorry to make you come in dear, I just need to get this paper work in to the accountant.”

Lisa left Jen in charge and headed out for the accountant’s office. As Lisa left she sashayed away from the shop, her ass moving in a seductive motion. Jen noticed her boss’s ass sashay as she watched through the window of the shop. Lisa was about 35, was in great shape, she worked out at the gym and watched what she eat. She had blond hair, green eyes. Jen sized her breasts up to be about a 36C cup, she had a slim waist, and hour glass shape with a nice ass. Jen had been working at the dress shop most of the summer, but never thought of Lisa in any kind of sexual way, she was always just her boss.

The store was dead, not a single customer and she was bored. So she decided to look around in Lisa’s back office, she would hear the bell go off if a customer came in. Jen started pulling open desk drawers and file cabinets, she wasn’t really looking for anything in particular, just bored. She pulled the bottom right drawer of the desk and saw a round long fleshy looking object, she pulled it out. There in her hands was a 7 inch dildo in the life size shape of a real cock, it had fake veins and everything.

“Why you old vixen” she said out load. Jen thought about using it on herself, but was afraid someone would come in to the shop while she had that thing in her pussy. Jen went back out to the front of the store and sat at the register counter. Jen started thinking of Lisa using that dildo on herself and began to get a little wet between her legs. She was thinking she would love to see Lisa use that dildo on herself, and she imagined Lisa using it on Jen also. Her hand slipped down to under her dress and she started slowing stroking her clit. She knew she had to behave, if a customer came, she couldn’t be indisposed.

About an hour after Lisa left, she returned.

“Turns out there was an emergency at the accountant’s office, so I didn’t get a chance to talk to him anyway, so I just left the paperwork with him, I’ll have to call him later. Damn taxes are a pain. Any customers?”

“Not a one” said Jen as she looked knowingly at her boss, she again pictured that dildo in her hand shoving it in and out of her pussy. Jen wondered what Lisa’s pussy looked like, she had only seen her own and Sally’s up close. Jen had seen other girls in the gym shower, but their legs weren’t spread. Was an older woman’s pussy different, she wondered?

“I guess it’s going to be a slow day today, if you want to go, I’ll pay you for the whole morning.” Lisa said, smiling at Jen. “Oh wait,” Lisa suddenly said “I have an idea. I’d like to give you a dress, I was going to give it to you as a going away present, an off-to-college present. I wanted to wait until your last day next week, but since the shop is slow, why don’t you try on some dresses now and pick one out?”

Jen was ecstatic with the idea of trying on dresses, she was eying a few all summer, but felt funny about shopping where she worked. Jen grabbed several dresses off the racks and said “I’d like to try these”.

“Good,” Lisa said “I’ll close the shop and help you pick out a good one, I can even help fit it for you” Lisa locked the door and put the closed sign out.

The shop didn’t have a dressing room, customers were led through a curtain to the back office. Lisa led Jen through the curtain into the back office as she had done with her customers, but this time she stayed in the back room with Jen thinking nothing of it; they were both women, Lisa wanted to help fit the dress.

Jen, not thinking, pulled her little summer dress off, she forgot for a moment she didn’t have any panties on, she now stood there with only a thin lacy bra on. Lisa’s eyes went wide and she uttered “Whoa, you don’t have any panties on.”

“Oh sorry”, Jen blushed, and made up a lame story about being in a hurry to get here this morning she must of forgot. Lisa really wanted to work with her on fitting the dresses, so she didn’t want to leave the back room, but she was a little embarrassed herself, she offered to get Jen a pair from the shop floor, but Jen said “Don’t bother, I don’t mind, and besides you’ve already seen me bottomless, no point in covering up now.” You’re supposed to have underwear on when you try on clothes Lisa thought nervously, then she eased up about it remembering Jen was trying on dresses not pants, so it shouldn’t be a problem.

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