Lilly’s Fun-filled Evening

Lilly was jealous of Emma. Her 17-year-old sister seemed to have everything Lilly wanted: she was allowed to stay up late, to go to teenagers’ parties by herself, she was always surrounded by attractive older boys, and, not least of all, she had larger breasts. Not like the little orbs beginning to form on 14-year-old Lilly ‘s developing chest, but real, rounded, shapely, succulent teenage breasts that attracted all the boys.

Emma, on the other hand, viewed Lilly as more or less of a pain. She was constantly trying to get her little sister to stop following her around, so she could party with her friends — hang out and drink and smoke dope and make out with boys. Although still a virgin, she loved making out and letting boys fondle her breasts and rub and squeeze her nipples. She had even let a few . . . finger her pussy to orgasm and she had something of a reputation around the senior class in her high school . . . for giving great hand jobs.

Needless to say, Emma was extremely popular with the boys and there always seemed to be several around, whenever Lilly wanted to hang out with her big sister. The boys and Emma did their best to ignore Lilly, which only fueled her jealousy.

Not that Lilly wasn’t a very attractive girl, in her own right. Medium-length dark brown hair framed a perfectly proportioned face with slightly pouty lips and an adorable little nose. Lilly had deep brown eyes, an infectious giggle, and a bright smile that showed cute dimples. Though her breasts were small (but definitely in full development), Lilly ‘s legs would have been the envy of any older girl. Seeing her walk down the street, even grown men found themselves transfixed by the rising and falling hem of Lilly ‘s school uniform skirt, entranced by her shapely, smooth and perfectly formed golden calves and thighs (Lilly preferred the freedom of skirts and dresses to the confinement of pants).

Her petite, nubile figure certainly attracted the attention of some of the more aggressive boys in her eighth grade class, who sometimes tried to “cop” feels of her budding breasts and irresistible little behind. Lilly was definitely not interested in them, however. The high school senior boys her sister hung out with . . . seemed so much cooler and more mature, if only she could get them to pay attention to her.

Lilly knew that her sister made out with her boyfriends, but she didn’t give sex much thought until the day she accidentally spied on her sister giving a guy a hand job. She was shocked! She had hardly seen a penis before, and certainly not an erect one! Lilly watched, totally fascinated, as her sister’s slick hand caressed the boy’s shaft. It was so rigid, and seemed to have a life of its own.

Lilly gulped as Emma began to stroke more rapidly and firmly and the boy’s breaths grew shorter and more labored, becoming moans of pleasure and desire. All of a sudden, the boy groaned and his cum burst out into the air, landing in big white globs all over Emma ‘s face, hands and clothes. Lilly gasped in surprise and excitement. A shiver like an electric shock shot through Lilly’s entire body as she watched the white cum . . . spurt out of the boy’s cock again and again.

Lilly couldn’t stop replaying that scene in her mind. She began to fantasize about boy’s cocks. Although she knew what sex was, her innocent mind couldn’t quite picture what it was like, so Lilly’s fantasies centered around being surrounded by several hard cocks, and of having them rubbing all over her face and body. And most important of all . . . her titties and stiff nipples that were almost always at play.

While having these fantasies, Lilly noticed a strong tingly feeling building between her legs, and she instinctively pressed her legs together to intensify the feeling. Soon she discovered that she could feel even better if she rubbed herself down below, and not long after that . . . she was regularly bringing herself off while fantasizing about being surrounded and rubbed all over by hard, pulsating, lovely cocks.

One day, the girls’ parents told Emma they would be going off on a much-needed getaway weekend, leaving her in charge. Now that Emma was nearly 18, they felt comfortable doing so. Emma, like any self-respecting teenager, immediately made plans for a party at her house, while trying her best to persuade Lilly to sleep over at a friend’s house that night. But Lilly would have none of it. There was no way she was going to let herself be shut out of an unsupervised party at her own house. The very thought of being there . . . thrilled her no end.

Using the threat of telling their parents about the party, Lilly finally got Emma to reluctantly agree to let her stay. Emma was disappointed and resentful, and in response, came up with some rules that she thought would protect her self-interests and still let her have some fun with the boys.

“Okay, you can stay for the party, but no drinking liquor or smoking ANYTHING for you,” she told Lilly sternly. “Also, anything you see . . . stays with you. You are not to report anything to anyone, not even Rachel.” (Rachel was Lilly’s best friend.) “And finally . . . my bedroom is OFF LIMITS, period. You are not to set foot in there for any reason any time during the night. Do you understand?”

Lilly readily agreed to Emma ‘s terms. She had no particular interest in drinking or smoking dope. Having never been to a party given by older kids, she didn’t really have any idea what might go on there. She was happy just being allowed to hang out at a party with Emma and her friends. She rejoiced in the anticipation of staying up late like her sister . . . and having fun hanging out with the older kids. And maybe some of Emma ‘s cool high school senior friends . . . especially the boys . . . would talk to her.

On the day of the party, both girls were nervous and excited. She had asked her friends to dress up for the party. As a result, Emma put on her slinkiest, sexiest dress. She was looking forward to having her pick of boys to flirt and make out with, to feel her up and maybe even make each other cum . . . hopefully several times. To Emma ‘s annoyance, Lilly kept hanging around as the older girl dressed and put on her makeup.

Lilly thought Emma looked stunning! Lilly begged her older sister to let her put on some of Emma ‘s makeup too. At first, Emma refused. But, after tiring of Lilly’s continual pleading, she finally relented.

“Okay, Lilly, but just a little bit. We don’t want you looking like a little slut. Here, let me put it on for you.” Lilly was happy that her sister was willing to help her, not only because Emma was an expert makeup artist, but also because she had been nasty and curt to Lilly all day.



When Emma was done, Lilly looked at her face in the mirror. It was perfect! Emma had applied just the right amount of blush and lip gloss to give Lilly’s pretty face a definitely sexy, yet demure and innocent look. Lilly felt so much older and more mature looking in the mirror. ‘God, I could pass for sixteen,’ she thought excitedly.

“Oh, thank you, thank you!” cried Lilly, hugging her older sister.

“Yeah, yeah, okay,” replied Emma, grudgingly accepting her sister’s gratitude. “If you really want to thank me, just remember my rules.”

“I will,” replied Lilly solemnly. The party took a little while to warm up, but soon there were lots of kids dancing, talking and having a good time. Lilly was excited to be part of it, but was a little surprised at how out of it, she felt. She stayed close to Emma as much as she could. But around 10:00 (Lilly’s usual bedtime), her older sister disappeared with a guy into her bedroom and Lilly was on her own.

She wandered aimlessly around the party. She knew some of the guys and girls there, but none of them were interested in dancing with her or giving her more than a friendly, if patronizing, hello. Anyway, the music was too loud and wild for her. Lilly knew she had promised her sister no drinking, but out of nervousness and boredom she sneaked a few sips of wine from some of the kids’ glasses when they weren’t looking. Lilly wasn’t used to alcohol . . . since she had only had it a few times on special occasions. She liked the effect the wine was having on her, making her feel more relaxed, attractive, and even sexy.

But after a while, she also felt a little tired. She decided to go upstairs to her room for a while to get away from the party, which was turning out to be a big disappointment for her. On her way to the stairs, she passed the TV room. The lights were low in there, but glancing in, she could clearly see two couples making out. On the love seat, a boy and girl were amorously entwined, French-kissing and wriggling against each other, while on the sofa another couple was doing pretty much the same. Lilly stood in the doorway, unable to stop herself from looking in on the scene unfolding before her.

The couples in the room seemed oblivious to her presence. Lilly wasn’t sure, but she thought the girl on the love seat might be Emma ‘s friend Kelly, a pretty 16-year-old junior. Her long blonde hair fell down across her face as she sat across her guy’s lap, passionately kissing him. Lilly could see the boy’s hand slowly sliding up and down the Young girl’s thigh. She thought she heard a throaty moan as he began softly caressing her breast through her dress with his other hand.

Lilly gulped as she saw his hand travel up under her dress. The girl pushed the boy’s hand away twice, but when it returned a third time, she let him continue. Lilly watched spellbound as the girl allowed her dress to be hiked further and further up her shapely young legs, until her pink panties were visible. Soon the girl’s thighs were parting . . . as the boy’s hand disappeared into her pussy. Lilly shivered with desire, wishing it was her sitting on his lap.

Meanwhile, the pair on the sofa seemed to have progressed even further than the first couple. Lilly recognized them as Bobby and Melissa, who were in Emma’s class. She could see that Melissa’s top was fully undone, revealing one small, very bare breast. Her exposed nipple glistened slightly in the soft light, and she knew it must have been sucked recently. But Bobby’s attention seemed to be elsewhere. As they kissed, Lilly noticed that Melissa’s jeans were unzipped and that Bobby’s hand seemed to be buried in the girl’s crotch. Soon the thin fabric of her panties were pulled aside as the teenage boy’s busy hand, caressed her.

Lilly found herself imagining what it would be like to feel what Melissa was feeling at that moment, and she caught her breath as she felt a familiar warmth building in her own pussy.