Babysitters

by pointless

Copyright© 2004 by pointless

Erotica Sex Story: Andrea's friend Cindy helps her discover her true sexuality while mom is away and little brother sleeps.

Caution: This Erotica Sex Story contains strong sexual content, including ft/ft   Teenagers   Consensual   Drunk/Drugged   Lesbian   First   Oral Sex   Masturbation   Petting   .

It had been a normal, boring suburban day. Chilly and rainy with a wind that cut through you and made it feel at least twenty degrees colder than it really was. Andrea hadn't seen the sun in two days. Another gloomily October in Michigan.

It was only seven thirty and it was already dark. The only good thing about autumn was what was just beginning to happen to the trees all around. Beautiful colors forming from the dying of the leaves.

Of course, Andrea couldn't have cared less about all of that. Tonight was the night she'd be planning for all week. Tonight was the night that her best friend Cindy was going to spend the night and she'd been absolutely giddy all day. She and Cindy always had so much fun just hanging out in her room with the door locked and the shades drawn doing stuff her mom didn't even want to know about.

Usually that fact would be enough to keep her happy and smiling all day long, but not this evening. No, her mom had to go and mess it all up by suddenly developing a social life out of the thin air. Mom's can be such a pain at times.

"What do you mean I have to watch Philip?" Andrea was now whining to her mother as she touched up her lipstick in the bathroom mirror obviously trying her hardest to ignore her daughter who had just asked that question a mere two seconds ago. "Why can't you just get Aunt Rachel to watch him?"

"Andrea, we've already been through this," her Mom replied, her frustration restrained but still noticeable, "Rachel has watched your little brother enough this week. Besides, you're more than capable of taking care of your little brother for a few hours until he goes to bed."

"But Cindy..." Andrea started to protest only to be interrupted by her mother.

"Will just make it that much easier for you. Really, Andrea, you've taken care of your brother before. He likes you, he does what you say and all you'll have to do is give him a snack, put in a movie and then tuck him into bed at nine. After that you and Cindy will have the whole house to yourselves until two. If everything looks good when I get back you might even make twenty dollars so you and Cindy can go to the movies tomorrow and you won't have to rake the lawn until tomorrow. I really don't see why you're complaining about this," her mother said calmly but firmly making it clear that the discussion, whether Andrea wanted to admit or not, was over.

Andrea just crossed her arms across her chest and walked away in a huff to her room while her mother smiled softly to herself. It really had been awhile since she'd actually been able to go out and have fun. Lately it had been all work, parent/teacher conferences, grocery shopping and doctor appointments. When her old college roommate and best friend had called her out of the blue earlier with an invitation to a night of drunken debauchery she just had to accept. She hadn't had more than two beers since the divorce had been finalized two years ago. She was well over do.

That, and she really missed the fun she and Tiffany used to have back in college. That girl had taught her so much about sex and having fun and she was still the same old Tiffany from back in the day. Wild, crazy and flirtatious. She just knew they'd end up in a hotel room like the last time she'd been in town. Just the thought of it made her wet.

As Andrea reached the top of the stairs and found her way to her room she found it hard to resist slamming the door behind her. Deep down inside she knew she had no real reason to be pissed. Her mom was right. Watching Philip would be easy. For a five year old he was actually quite even tempered and he did listen to his big sister. She was actually the one who finally got him potty trained when her mom had all but given it up thinking it an impossible task. Watching her little brother would be cake.

Still, like any normal American child of the twenty-first century she would've preferred to have had her cake and eaten it too. A house to herself was a blessed event. A house to herself and her best friend would have been pure bliss. The loss of that rare opportunity was reason enough to pout for next fifteen minutes alone in her room while she waited for Cindy to be dropped off by her brother, so that's just what she did after she had finished flinging herself on her bed in dramatic fashion and rolled over to stare at the ceiling in weak anger.

It seemed like it was only seconds later that she was startled awake by a loud knocking on her door. She had apparently dozed off and it took her a few seconds to remember enough to ask who was there. The door swung open almost instantly to reveal Cindy standing in her doorway with her usual sarcastic smile firmly set on her cute, slightly tanned face.

Cindy and Andrea was different as night and day in so many ways it almost boggled the mind to think that they were friends. Andrea was the usual product of suburbia with her perfect dirty blonde hair in shoulder length cut framing a small cute, dimpled face with a delicate nose set below and between brightly innocent looking blue eyes. Her clothes always looked new and freshly cleaned as if she had a new outfit made everyday just for her.

She was short and would probably always be, but her body was already showing the signs of smooth, gentle curves that would make her the envy of her classmates for years to come. Her breasts were small, but well shaped. At her age she was already finding herself turning down guys almost twice her age. Not that she had a problem saying no. She reveled in the attention, but, frankly, she just had no interest in the attentions of the opposite sex regardless of age.

Cindy, on the other hand, always wore clothes that seemed to be handed down from her two older brothers and her sister, because the vast majority of them were. They all had that well worn quality about them. Often they even had holes or permanent stains. Her hair was black as the night and went seemingly wherever it pleased without appearing to be too messy or nappy. Her skin had the light brown tone she'd inherited from her father's side of the family and her eyes deep brown from the same side.

Her body was a little more firmly planted on the side of womanhood than her slightly younger friend. Her breasts were a little larger, her butt a little fuller and her hips a bit more pronounced. She was the envy of all the young girls from the trailer park where she lived and spent most of her free time avoiding. Cindy had no problem admitting her hatred of her roots. The only thing her parents were good for was easily stolen money and booze. Even at her young age Cindy was more than acquainted to the joys of alcohol among other things.

It wasn't all economics and physiology, though. Andrea was the cheery optimist to Cindy's dark cynic. When they had first met Andrea had been firm believer in the artistic value of bubblegum pop while Cindy spent most of her time stealing what passed for punk cd's nowadays. Cindy had managed to wean Andrea off of the worst of cd collection with a mixture of Sleater-Kinney she'd borrowed from her sister and some Dead Kennedy's she'd "liberated" from the local music store. Cindy was all about the old school. It was one of the benefits of having siblings up to twelve years her senior.

"What's up, sleepyhead?" Cindy teased as she shut the door behind her and walked over to Andrea's bed to have a seat.

"Nothing," replied Andrea as she rubbed her eyes, "Just waiting for you to get her to tell you the bad news."

"You mean the babysitting?" Cindy said with a frown and an eye roll as she shimmied her backpack off and onto the floor. Andrea just nodded and sneered in response as she sat up on her elbows.

"Yeah, my mom is going out with her old roommate or something. She won't be back until two."

"Old roommate, huh?" Cindy said with a wicked smile and raised eyebrows causing Andrea to giggle.

"Shut up," Andrea said as she got up from her bed, "Not everyone's a pervert like you."

"Moi?" Cindy responded doing her best to look innocent and failing miserably. Andrea giggled again. Cindy did that to her. For some reason she always felt so giddy around her.

"Yes, you. Like you didn't know, you lesbo,"

"I wouldn't talk, missy. You didn't seem to mind my fingers in your..." Cindy started, but was quickly interrupted by a gentle, yet firm push from Andrea.

"Shut up! I was drunk and you know it. That doesn't count. You took advantage of me, you slut." Andrea said adamantly, but somewhat unconvincingly to her still smirking friend.

"Like you didn't like it," countered Cindy calmly.

"That's beside the point. I'm no lesbian and you know it. Just remember that," Andrea said and then smiled meekly. Cindy's smirk was still there on her cute, deceptively angelic face. She knew the truth. All she needed was time and a little luck and Andrea would be hers.

The girls were forced to end their little game of hard to get by the sound of Andrea's mother yelling from downstairs. Andrea yelled her response and then returned her gaze to Cindy. Both girls frowned knowing that it meant that the most boring part of their night was about to begin.

As they made their way downstairs Andrea noticed her mother standing by the door looking at her watch and frowning. She was shocked by how beautiful her mother looked in her sleek, low-cut black dress that had been hanging in her closest since her last big date with the asshole cop she'd dated right after the divorce. It was absolutely amazing. This wasn't the same woman that had fixed her supper only a few hours earlier. This was a thirty-five year old goddess.

From the whistle she heard coming from Cindy she knew she wasn't the only one who thought so. For a second she thought that maybe Cindy had been right about what was going to happen tonight between her mother and this old roommate. She quickly let that thought exit her mind though. Her mom was no lesbian. Was she?

"Nice dress, Miss Evans. You look awesome," Andrea heard her friend say as they reached the bottom of the stairs. Her mother just smiled broadly and thanked Cindy politely before returning instantly to her role as mother to give Andrea her instructions for the evening. It was all stuff Andrea had heard a thousand times before.

"And remember," her mother finished, "If everything looks good and I don't hear anything bad from your little brother or," and she placed emphasis on this part and looked at both girls with a stern expression on her face, "from the neighbors there'll be some money in this for you both. Understand?" Both girls nodded their agreement.

"Don't worry Mom," Andrea said in her best reassuring tone, "everything will be fine."

"Good, now your brother is the living room watching Finding Nemo. Once it's over I want him in bed, so you might get working on that snack. Now, give me a kiss and I'll see you in the morning if you're not up, which you'd better not be." Andrea kissed her mom on the cheek and said good-bye as her mom went out the door.

"Someone's going to get some pussy..." Andrea heard Cindy say in a sing-song voice behind her. She turned around to see her friend smiling a knowing smile and Andrea just rolled her eyes at her.

"Come on, let's go make that snack. We only have an hour and then we can have fun."

For the next hour the girls tended to the minimal needs of Andrea's younger brother. Well, Andrea did while Cindy made herself at home on the couch and enjoyed the movie and chatted with Philip about his day at kindergarten when he wasn't staring blankly at the screen watching computerized anthropomorphized fish do their thing. Not that Andrea cared. Throwing a bag of popcorn in the microwave was hardly a two person job.

Finally, nine o' clock rolled around. The cute, little clown fish was reunited with his father and all was right on the reef and Phillip was already yawning and having trouble staying awake. As the final credits rolled on the screen Andrea picked up her little brother and carried him upstairs to his bed. She tucked him in and gave him kiss goodnight. He was out before she even got to the door.

"He's asleep," Andrea said as her bare feet hit the cool tile of the breezeway to Cindy who was standing in front of the entertainment center DVD in hand.

"Awesome," Cindy said as she bent over a bit and put the disc in the player. "Now I can watch you piss your pants in fear."

"Please. Like I've never seen a zombie movie before," came the flippantly indignant reply from Andrea as she planted herself on the couch. She was quickly joined by Cindy who sat down right next to her despite the abundance of room on the massive sofa.

"Don't try to act all brave like I don't know any better," teased Cindy as she snuggled up to her friend and pulled an afghan off the back of the couch and threw it over both of their legs. Cindy's arm quickly found it's way around Andrea's shoulder. Andrea's head found it's natural spot on resting on Cindy's shoulder with a resigned sigh.

"Oh, shut up," Andrea replied quietly as she made herself comfortable leaning against Cindy's soft body, "the movie's starting."

As they watched the movie the girls remained close only shifting when it was necessary, but never losing contact with each other. Andrea would never admit it, but loved the feel of Cindy's body touching hers. The soft skin, her warmth, her smell. It was all so comfortable and right.

It was weird. She was hardly a touchy feely person. Far from it in fact. She hadn't hugged or kissed her mother in ages. She'd lost every boyfriend she'd ever had (all three of them) because she'd just never been comfortable enough with them. Sure, she made out with them, one even got as far as feeling up her breasts, but it just never felt right.

Not that she was lesbian. At least she didn't think she was. She was just curious. Besides, fingering a girl didn't make her a lesbian. She was just returning a favor anyway. It was more like a drunken experiment than actual sex, right?

That night had been a lot like this one. Cindy had come over to spend the night while Andrea's mom had gone out with her girlfriends for a drink. Philip had been spending the night at his dad's like he did a couple of times a month. They didn't have the same father. Not that it mattered to Andrea. He was still her little brother.

The plan had been to watch a couple of movies then go to bed and wake up the next morning and go to the mall so Cindy could help Andrea spend what was left of her birthday money on some cd's. Andrea was getting bored with the teeny bopper crap she'd been listening to and, though she hated to admit it, Cindy had great taste in music and had knowledge of bands that Andrea had never even heard of. The girl knew her pop culture.

The plan had gone great for awhile. They watched the first movie, some boring teeny movie Andrea had picked out on a whim much to Cindy's dismay. Then they watched the second one, a sad, sappy movie of Cindy's choosing which also sucked.

It was half through the second movie that Cindy had brought out the bottle of irish cream and had non-chalantly took a swig and passed it to Andrea.

"What the hell is this?" Andrea asked as she sniffed the bottle. It smelled sweet and definitely alcoholic. She'd smelled her mom's rum before. This wasn't half as bad, but it was definitely booze.

"Irish cream," Cindy said, still playing it cool, "Drink it. It's good. You'll like it. It might help make this movie interesting."

"But isn't this alcohol?" Andrea asked quietly as if she was afraid of being caught despite the absence of an adult presence.

"Yeah," Cindy had replied a little sarcastically, "Just drink it, Andrea. It aint gonna kill you or anything. It tastes good. You'll like it. Trust me."

That did it. If Andrea had one weakness it was peer pressure. She couldn't stand to be viewed as a wet blanket ruining anybody's fun. It also helped to know that regardless of whether she drank any or not Cindy was going to get drunk. She actually seen her drink before and she'd tried to talk Andrea into joining in then too. Luckily( or unluckily) Andrea had had to go home early that first night so she had an easy out. She didn't have that luxury that night.

So Andrea swallowed her fears as she took a swig from the bell shaped bottle of sweet liqueur and gagged. Cindy laughed at her and urged to take another swig. Andrea looked at her a bit incredulously, but obeyed. This time she took a smaller drink and avoided smelling it. To her surprise it actually tasted pretty good after you got past the slight tinge of alcohol. Like a sweet chocolate milk, but entirely different. Without being urged she took another swig before handing it back to back to a smiling Cindy.

"It's good isn't it?" Cindy asked before taking drink herself. Andrea just nodded as she grabbed the bottle from Cindy and took another gulp. The girls kept passing it back and forth until they emptied the bottle of every last drop of it's contents. By the time they were done Andrea had downed more than her share, but Cindy didn't seem to mind. In fact, she just pulled another bottle from her bag and the girls managed to finish it off before the credits rolled on the second and, as it turned out, final movie.

By the time they were done drinking both girls were a loud, giggly mess. Andrea was spouting off anything that came to her mind and Cindy wasn't any better. Andrea still wasn't quite sure how the subject of sex had come about, but she knew that once it was brought up it became the sole subject of discussion.

Cindy did most of the talking considering that between the two of them she was the only one with any real experience. Andrea remembered her friend going into great detail about the time she let her oldest brother's best friend eat her pussy because she was bored. Her love of detail caused Andrea to giggle like a fool. Apparently he was rather unimpressive.

When Cindy started talking about her experiences with girls Andrea stopped laughing. Instead she listened with rapt attention to every detail they came from Cindy's expressively dirty mouth. Even at her young age Cindy had had quite a few experiences with girls. Many Andrea knew and more then a few came as quite shock. One in particular caught her attention.

"You fucked Becky Silverman?" Andrea had asked in disbelief.

"Hell yeah, she was good too. Why? Did you know her something?" Cindy had responded.

"She was my best friend back in seveanth grade. I can't believe you fucked her. She was always such a prude. She wouldn't even masturbate in front of m..." Andrea suddenly stopped herself, but it was too late. Cindy had her and pounced upon her admission.

"You, little miss virgin prude, have masturbated in front of people? You're fucking kidding me!" Cindy nearly yelled as she smiled broadly. Andrea just blushed and froze. She'd never told anybody about that and she had never planned on it.

"Oh, come on. Don't be all embarrassed," Cindy chided her. "I just told you a bunch of shit and you can't talk about the one time you masturbated in front of some girl? Don't be a pussy, Andrea."

"We didn't do it," Andrea said quietly distressed by the fact that her past was now the focus of the conversation.

"Well, why not?" Cindy had pressed on, "Come on don't be shy. I was just teasing you. I'm your best friend. I'm not going to make fun of you."

"I don't know," Andrea sighed, "She didn't want to."

"But you did, huh?" Cindy asked.

"Well, yeah," Andrea admitted openly, "It was my idea."

"Did you do it anyway?" Cindy pushed the questioning further. The subject intrigued her and turned her on.

"No!" Andrea said loudly. "What do you think I am, a perv?"

"Apparently," Cindy cracked and Andrea blushed causing Cindy laugh gently at her friend. "Oh, come on. If you're a pervert for wanting to watch a girl masturbate and I actually had sex with her what does that make me?" Cindy said as she leaned over slightly as she put her hand on Andrea's arm.

Andrea just kept blushing. She didn't know why she even mentioned it. She had never told anyone about that night before. She had really wanted it to happen. Andrea couldn't have admitted it then and still wouldn't now, but she had been attracted to Becky like she had never been attracted to anyone else before. She'd cried the next morning after Becky had gone home. Not just because she'd failed to see her friend masturbate, but because she knew that it meant the end of their friendship. It did. Becky made herself scarce soon after that.

And now here she was hearing how her new best friend had sex with her old best friend. It was weird and confusing to say the least. Damn it, she was jealous even though she knew she shouldn't be. The booze was definitely getting to her head.

While Andrea sat there blushing and worrying about her sexual identity Cindy's drunken mind was forming a plan. She knew exactly what was going on in Andrea's head. She witnessed it several times and, like a lot of girls of her persuasion, she had moments like these herself. She'd been able to work it out, but not everyone was able to. Some people needed a little help. Cindy was in a helpful mood.

"Come on," Cindy said as she got up and looked down at Andrea. Andrea just looked at her friend confused.

"What?" Andrea said after a pause that seemed to last an eternity. Cindy just responded by grabbing her friends hand and pulling her to her feet.

"Come on," She said as she began to lead her upstairs, "I have something to show you."

Andrea followed wondering what exactly was going on. If she had known at the time she probably would've ran the other way and regretted it for the rest of her life. When they got her room and Cindy began unbuttoning her pants Andrea almost did just that. The only thing that stopped her was fear of missing out on something she'd wanted for so long.

"What are you waiting for?" Cindy asked as she pulled off her jeans and panties in one tug, "Get undressed."

"What... what are you doing?" Andrea asked in a shaky voice even though she knew exactly what Cindy was going to do. The butterflies in her stomach were going crazy even as her pussy began to tingle and moisten at the sight of Cindy's trimmed sex. The butterflies nearly flew out of her stomach when Cindy stepped up to her and grabbed her hands again before placing a soft kiss on her lips.

"I'm going to show what you missed out on, silly," Cindy said with a wink as she reached down to help Andrea rid herself of her cargo pants. Andrea was lost in her thoughts. She was both scared and unbelievably aroused. She wanted to move, to either run out of the room or help Cindy remove her pants; she wasn't sure, but she was frozen.

Cindy didn't seem to notice as she finished unbuckling, unbuttoning and unzipping and began to tug Andrea's pants and panties done in the same manner she had her own. As she lowered herself down to her knees to help the clothes on their way down she found herself staring at Andrea's beautiful pussy. The scent filled her nose. She could almost taste her friends arousal and she almost did, but she kept her urges under control. No need to scare Andrea away by being too forward. With any luck there would be plenty of time for that later.

"Come on," Cindy said as she took back up and smiled softly at Andrea. She grabbed her friends shaking hand and led to her own queen size bed and guided her to take a seat against the headboard. Andrea allowed herself to be led and positioned almost as if she was in a trance. Really, she was. She was simply entranced by the sight of Cindy's pussy.

Once she was comfortable Cindy simply spread her legs and began to slowly massage her pussy as Andrea gasped and stared at her friend in awe. She somehow hadn't expected Cindy to just start touching herself like that. She'd almost thought it was all just an elaborate joke, but the sight of Cindy's long fingers slowly sliding between her already slick pussy lips as her other hand caressed her breasts through the thin material of her t-shirt proved to her that this was for real and, more importantly, this was beautiful.

Cindy's eyes were closed as she patiently began to work her fingers over her sex. She was obviously a girl who knew what she liked. Her trimmed fingers took their time rubbing her swollen lips as her thumb made slow, tight circles around clit. The moisture of her sex glistened in the soft light of Andrea's room as she softly moaned letting Andrea know she was enjoying herself immensely.

While Andrea's eyes were glued to the sight of Cindy's exhibition her own hands lost their lethargy and began to almost unconsciously began to work their way to her pussy. As her fingers grazed her clit Andrea let out a hissing sigh and a shiver ripped through her body. She closed her eyes for a brief second as the pleasure of the mini orgasm coursed through her, but once it faded her eyes instantly returned to the sight before her.

The pure beauty of Cindy's fingers working in and around her pussy as her hips slowly gyrated against the stimulation was absolutely spellbinding. Andrea did her best to mimic her friends movements. When Cindy Rubbed her clit Andrea did the same. When Cindy slowly dipped her index fingers into her depths Andrea followed her lead and let out a quavering moan. The smell of the mutual arousal filled both girls' nostrils.

Cindy's eyes slowly opened as she felt herself approach her first orgasm. Her eyes went from Andrea's fingers madly pumping away at her tight, slick flower up her tight belly that was exposed by Andrea's arm as Andrea savagely molested her tiny breasts under her thin t-shirt to her exquisitely contorted face obviously focused on Cindy's sex. The sight made her want to come that much more. Beauty, pure beauty.

"Oh god, Andrea," Cindy panted to her friend causing Andrea to remove her gaze from her handy work to Cindy's face, "I'm going to come, baby. Come with me. Oh God, come with me."

Andrea just groaned as she redoubled her efforts to obey Cindy's command. She'd never been this aroused. It was unbelievable. At the moment she realized that Cindy was the best friend she had ever had and ever would.

And with that thought she felt her orgasm begin to build and her breathing came in quick pants until she felt her whole being enveloped by a surge of pleasure unlike anything she'd ever experienced before. She screamed with ecstatic joy as bliss shredded her mind and her body tensed up and became rigid.

The sight of Andrea coming was more than enough to push Cindy over the edge as she came with a shivering squeal as her eyes squeezed shut. She saw stars as Andrea's screams of joy echoed through her brain. It was glorious.

Neither girl's hand left their work as they came down from their orgasm. They were too keyed up to stop now. Andrea's fingers were still wantonly pounding away at her wet, throbbing pussy. It was now Cindy's turn to stare in amazement. Cindy, however, was not content to just watch.

Andrea nearly screamed when she felt her fingers being joined by her friends, but her scream was silenced by Cindy's mouth on hers. The feeling of Cindy's fingers working her pussy and her soft lips against her own left Andrea weak. Any desire to protest quickly melted away.

Cindy's fingers were like magic on Andrea's pussy. She was pure putty in her friends skilled hands. She didn't even notice at first when Cindy began to guide her left hand to the moist junction of Cindy's thighs, but once she felt that slick fur touch her finger tips she wasted no time in getting to work.

The girls shifted position until they were on their sides facing each other, bodies close together as they kissed and did their best to bring each other to another glorious orgasm. The scent, the feel, everything was so perfect. Cindy's tongue felt so right in Andrea's mouth. Her warm body felt so good pressed against Andrea.

Cindy's thumb was making tight circles around Andrea's clit as she worked her index and middle fingers in and out of her friends tight sex. Andrea did her best to keep up with Cindy as she tried to keep her head, but as Cindy hit spots she didn't even know existed she had a hard time just keeping her fingers inside of Cindy's sticky hole.

Not that Cindy minded. She was so turned on that even the clumsy ministrations of her inexperienced friend were enough. She ground herself against Andrea's palm. Her main task was bringing Andrea to her second orgasm of the night anyway. Her own pleasure could wait.

Andrea was getting close. Those glorious fingers were driving her mad. Her moans easily escaped the deep kiss she shared with Cindy. Her pelvis pounded wildly against Cindy's hand as she felt it building and then with another scream she came again.

"That's it," Cindy whispered into Andrea's ear as she quivered against the invading fingers that were now thoroughly soaked with girl come, "Come for me. You're so beautiful... So beautiful."

Andrea's hand came out from Cindy's pussy as she wrapped her arms around her best friend and kissed her hard while Cindy continued to play with her through the entire orgasm.

"Oh, god. That was gr..." Andrea started to say as she finally came down from orgasmic high and broke the kiss with Cindy, but the sound of the garage door opening suddenly made her realize that she and Cindy weren't the only people in the world.

 
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