Prissy Penelope
Chapter 1

Caution: This Coming of Age Sex Story contains strong sexual content, including Heterosexual, Gang Bang, Group Sex, Black Male, White Female,

Desc: Coming of Age Sex Story: Chapter 1 - A Rich little girl finds herself in sex...

Pepperdine Prep School had a reputation of turning out the finest upscale, trophy, daddy's little rich girls. The school was next to impossible to get into. If you had to ask you couldn't afford it. But, there was one young lady at Pepperdine with a naughty secrete.

Penelope Longfellow was the class president, on the deans list, straight A student and head cheerleader. She had the latest Mercedes, all the latest designer clothes, laptop and camera cell phone. Penelope had it all.

She was treated like royalty and she looked down on her subjects. She towered over the rest of the women, standing a perky five foot ten, firm real thirty six d's, long following high lighted hair. Penelope's has a picture perfect face with pouty lips, small waist, sweet hips and long sexy legs.

Penelope led a story book life except one event when she was a child that led to un-controlling desire. When she was a young girl needing her daddy's attention, she was woken from her sleep on the couch, where she often waited for her father when he worked late.

Clearing the sleep from her eyes she walked towards the dens cracked door, where she saw her father fucking the maid. She was bent over his desk with her panties around her ankles. Her breasts were exposed, nipples erect and her fathers hands were all over them. She watched as her father's cock slide in and out of the maid.

The look of desire on his face while he fucked her pussy was amazing. When he did open his eyes the passion he had caused her young pussy of nine to tingle. She wanted her father to touch and look upon her like that. His moans moved her in away his voice never did.

At first she thought how dirt and disgusting it was to see her father. Slap the maid on the ass. Watch him make the maid suck his thumb and when his thumb was wet. He would thrust it deep into her ass hole. The maid would scream out in what she would learn later to be high intense orgasm. She watched as his long dick fucked her very wet pussy. While his wiggling stiff thumb pumped her ass.

Penelope almost gagged and looked away when he removed his thumb, forced it back into the maid's mouth. She resisted at first, but, he demanded she suck his thumb. She quickly opened and hungrily sucked it into her mouth. The sound the two of them made cause her to turn back. The look on the two of there faces caused her young nipples to thump as well as her clit.

She watched as the orgasm engulfed them. Ran through them, kept there bodies pumping and working together. The orgasm added intensity and passion to there sex. The way he stroked her, caressed her and touched her. The way they looked at one another, Penelope never seen her father look at her mother like that and yes ... she seen them have sex as well.

But, this was dirty, nasty, raw and un-tamed fucking. She never saw a woman so, subdued, so giving and so satisfied. Her father surprised her with his roughness, his driving desire, his willingness to please. Being daddy's little girl she wanted this, she craved this. Witnessing this act changed her whole out look on sex and love. She knew her father loved her mother, but, her father desired the maid.

Penelope lost her virginity four years later. It was nothing like what her father and the maid had. He was a nice young man a couple yeasr older than her. He kept asking her if she was alright and was he hurting her. All the while she wanted to scream, fuck me. Treat me like a little bitch ... fuck my pussy, she wanted to tell him.

But, by this time her mother instilled in her to always be a lady. Never let your wild side take over. You're a warm and beautiful princess. Your always need to be treated genital and sweet. They would always set her up with boys like that as well.

Penelope kept on having sex, but, her frustration grew. She even ran a boy off when she commanded him to fuck her and treat her like the bitch she was. This went on until she was sixteen when little miss debutant took matters into her own hands. She put on the shortest, tightest mini-skirt she had. Off course she put on her do me pumps and ordered the limo driver to take her to the dirtiest, roughest bar he could find.

Penelope with her hips swaying from side to side, she walked into a dimly lit biker bar. The bar was full of sweaty smelly men who had been riding all day. When they got to Penelope there wasn't a soft cock in the house.

She made her way over to the bar and ordered a drink. She slammed it down and ordered another. She sipped on this one as three large men approached her. One man was about six one, clean shaven, nice built. His name was Paul. The next to Paul was Mike. He was about five ten, stocky with a five o'clock shadow. Then there was Billy the wild one of the three. He stood about five eight very well built and a smile that would set a woman's heart a fire.

Dayummm ... she's tender, Billy announced. Wouldn't mind getting me a piece of that, was Paul's comment. I Bet, this spoil little rich bitch hasn't even been fucked right, yet, Mike added.

Little did he know how right he was, Penelope thought. She sat there, her pussy was already moist. Her body tremble as she felt there stares all over her. Penelope felt her nipples get stiff and raise the material that covered them. She was finally feeling dirty, she was learning what it felt like to be the object of desire.

Mike grabbed the bar stool and spun it around. They saw how erect her nipples were. They commented while Billy put his firm hand on her exposed thigh. A flush fell over Penelope as her pussy became wet.

The sheer panties she were wherein were soaked through as the masculine hand inched up her thigh. The guys watched in amazement and when her thighs parted. A hush surrounded the bar while more men were drawn over to the only woman in the place. The men gasped while there buddies hand went under her skirt.

She loved the feel of this man sure hand on her pussy. His hand invaded her wet pussy like he was meant to, sending thrills all through her. Not all dorky or clumsy, unsure if he was suppose to be there or not. Like the boys she was use to.

Billy's hand rubbed the outside of her panties. He moaned from the intensity of her wetness and heat. She's soaked boys, he hissed. Then he grabbed her sheer panties and ripped them off. Penelope came ... from the roughness, the force, the power and naughtiness. She loved the look of desire in there eyes and the lust on there faces.

There was a cheer when Bill held the wet panties to his nose and breath deeply. Billy never smelled such an erotic scent before. That's when Paul reached inside her top and set her thirty six d's free. The nipples stood proud as Penelope stuck them out for all to see.

There she was in front of men she didn't know. With her breast exposed, panties ripped off and a soaked pussy. Men wanting to put there cocks in her. They wanted grab her hips and squeeze her ass while they ram there dicks in and out of her.

Paul started things off when he closed his fingers around her perky nipples. Penelope moaned, as the sensation ran through her body to explode in her pussy. Her juices flowed and was ready to be entered.

Mike pushed Billy out of the way and pulled out the biggest cock she ever seen. Up until now her fathers dick was the largest Penelope had ever seen. Her father has an nine inch prick. But, Mike's cock had to be had to be ten inches long. With cheers from the crowd he guided his long dick to the opening of her soaked twat.

He ran the head of dick along her soft pussy lips, while Paul twisted and teased her nipples. Her body was on fire and she loved the attention she was getting. That's when Mike eased his dick into her wet pussy. Her tight coochie wrapped around his dick and drew a deep moan from him.

She is damm ... tight and wet to, Mike announced. Her pussy was hot, so, hot as he inched his long dick in this rich cunt. He watched her body quiver while Paul tweaked her nipples. He saw how totally turned on she was. He watched as she got her tight ass close to the edge of the bar stool. She also pulled her legs back to allow me deeper into her pussy.

Billy wanted in on the fun, so, he orchestrated the repositioning of Penelope. He told Mike to hook her under her thighs. They swung her around on the stool and Mike never took his penis out of her. They placed another stool under her, she laid across two stools.

Paul went back to massaging and teasing her young tender breast. This left only Penelope's hot mouth. Billy wasted no time pulling out his eight inch fat cock. He wasn't as long as Mike, but, he was much thicker. Penelope's mouth was stretched when he slammed his cock in it.

Billy was exactly what Penelope wanted, confident, rough and a big dick. She also wanted Mike with the longest cock she ever seen. She wasn't quite sure about Paul yet, but, he was giving her breast a good working over. Her mouth full of thick cock, her breast being fondled and her pussy being filled deeper than it had ever been before, the combination was too much for her. Penelope sucked deeply on Billy's cock. She arched her back to push her nipples forward for Paul's touch. While her pussy clamped down on Mike's long cock.

Billy and Mike moaned from the pleasure they were receiving as Paul put his mouth on each of her nipples. The feeling was titillating as he pushed her tities together and sucked both nipples at once. The sensation drove Penelope crazy, her pussy and mouth went crazy.

Dayammmm ... your mouth is sooooooooooooo ... HOT, Billy yelled, to the applause of the crowd. Not as hot as this sweeeeeeeeeet ... wet pusssssssscy, Mike told them. They couldn't help, but, to fuck her moth and pussy.

Mike put her legs on his shoulders and pounded his long cock deep into her cunt. She took every inch of his long dick while her pussy quivered over every inch. The long stroking of Penelope's pussy drove Mike wild. In-and out ... in -and out, he drove and pulled his cock.

Billy had a hand full of Penelope's hair. Holding and controlling her head as he fucked her mouth. There was pain with the pleasure. Every time he yanked her by her hair, she would rake teeth along the shaft of his prick. Penelope loved the taste of his cock. Billy cooed from the suction.

Paul finally pulled out his dick and put his meat in Penelope's hand. Her soft delicate hand went right to work on his seven inch cock. Yanking on it, pulling it and caressing it. She had pre-cumm seeping out of his one eye in no time.

Penelope loved having dick in her mouth, her hand and her tight pussy. She felt so naughty and sleazy as they used her the way the wanted to. Just like her daddy used the maid the way he wanted to. She remembered the look on the maids face. The look of intense gratification with a deep desire, Penelope was having those same feelings.

Mike couldn't take any more of the soft tight pussy he was fucking. Her pussy did things to his dick he had not felt before. Clutching and then double clutching his penis. Most times her coochie would clamp down on his cock half way out. Her twat wouldn't release his shaft until only the tip was left in her. That's when her pussy double clutched around the rim of his cock. The sensation caused his nut to release the man juice he had built up. Slamming his dick deep as he could. He roared out, I'm coming deep in this prissy bitches pusssssssssssssscy.

The crowed chanted ... Mike ... Mike as his sperm filled her up. Her pussy jumped some more. Squeezing out every drop of his cumm as it could get. He filled her so much that it seeped out the sides of Penelope tight pussy. It flowed down her ass dropped to the floor and formed a puddle.

Penelope marveled as the dick fucked her pussy. She could feel him become more ridged while he slammed his cock in and out. In and out ... her inner pussy muscles couldn't help, but, grasp his cock. She also felt her pussy clutching the rim of his dick head, igniting his powerful surge into her tight pussy. The erotic pleasure she felt as his penis touched places no other man had touched before. Her own powerful climax was achieved when she felt his hot orgasm splashed her insides. As soon as Mike's slipped out of her another hard dick was pushing in her. Penelope loved the way she was getting used.

Billy's was on his way to climax as Paul replaced Mike in between Penelope's sexy thighs. Penelope increased the suction on his cock when her climax reached its peak. Her tender mouth and suction pulled his fore skin over the head of his penis. This drove Billy wild because of the sensitive nerves in his fore skin. His balls tightened and she sucked his jism right out of his twitching dick.

Her mouth filled with man juice to the point her cheeks puffed out, as her hand was stroking Mike's long cock back to life. Her pussy was being fucked by Paul's nice size dick. Penelope was in ecstasy and she loved it.

The crowds roar was way too loud for any one to hear Billy's eruption. But, the roar became feverish and down right crazy. When they saw a few drops of semen seep from the corner of her mouth. They knew she sucked his balls bone dry.

Mike started directing people once again. By this time Mike was fully erect and Paul pouted. Because, Billy made him pull out of Penelope's sweet tender pussy, Penelope was still trembling from her multiple orgasms. When Billy instructed Mike to flip Penelope on the bar stool, there she was bent over a bar stool with a room full of people looking up her wet, dripping, hot pussy.

She came some much along with Mike's cumm her asshole was completed coated. Mike couldn't resist her tight virgin butt hole. He stepped up with a hush over the crowed and wet the head of his cock in there mixture. Every one there knew he was getting ready to take her cherry ass.

Penelope didn't even tightened up when she felt his dick head at her brown hole. She wanted this, it would complete her tutorial as a truly desirable promiscuous young woman. Her lips parted and her eyes closed as the penis pushed into the orifice. Mike was gentle, taking his time not to rip her apart.

Once the tip of his cock was in he took a break. The pain wasn't as bad as she thought. In fact the pain let her know she was alive, hungry for sex, passion and affection. He inched his dick even further into her ass, Penelope's mouth was wide open now. Not a sound came from her as the pain and pleasure gripped her like a vise.

With half of his long dick in her ass, Penelope's ass puckered and she came like it was the end of the world. Her passion screech was heard through out the whole bar. Her back arched, her nipples thumped, her pussy exploded and she wanted more. That wasssssss ... fuckinnnnnnng AWESOME, she yelled. Please, pleaeeeeeeeeeeeeeeeeeeeeeeese ... fuck my assssssssssss, she begged.

Penelope began bucking back on his rod, ushering his penis deeper into her tight ass. Penelope became wanton; her whole body was bath in eroticism as the last few inches were forced in her butt. The climax was just as intense as the last one. With just a few differences, Mike's balls rested on the nap of her ass. Mike was ejecting his man juice deep in her tight ass and Penelope shook from the orgasm.

This left the two of them panting, sucking for air as Mike's dick deflated and eased out of her tight ass. Her hips gyrated, begging and demanding for more dick. Paul who hadn't cumm yet, grabbed Penelope's rotating hips to study them. He wet the tip of his cock in all of her cumm. He began to ease his cock into her tight ass.

The crowd yelled; FUCK HER ASS ... FUCK HER ASS. He was too excited to be gentle like Mike. But, he left it loose enough that Paul couldn't hurt her. His dick rushed in and she slammed her hips back. Her ass clamped down around his cock. Setting off an eruption in Paul's nut sack, he lost all dick control when her tender ass milked his balls.

Although Paul was quick he remained hard. He locked on to Penelope's hips and jack hammered her sweet ass. His cumm coated her ass tunnel real well, making it a lot sweeter to fuck her tight ass. The crowed clapped with every slap of Paul's pelvis into Penelope's tight, soft ass.

Billy was done directing yet. He told Paul to sit on the other stool. Paul said, alright, but, this time he pulled Penelope with him. He sat on the stool with Penelope's hot ass wrapped around his dick. Her legs spread over each of his for everyone to get a nice view of her tender, young pussy.

The view didn't last long thou, as Billy put his thick dick in her pussy. With her ass and pussy full of cock, Penelope was nearing another climax. She knew she was going to get down and dirty tonight. But, two cocks in each hole with another on stand by. At least a half a dozen orgasms and the best sex of her life, in front of a crowd of people she doesn't even know. The thought intensified her climax further as her pussy gripped the cocks in her ass and cunt.

The two men grunted in pleasure as her highway and twat tried to milk there nuts for there jism. It took them a few minutes to get in sync with one another. But, once they found a grove the two men was fucking Penelope orgasm after orgasm. Her moans were evident that she needed, wanted and desired to be used like this.

Mike was not going to be left out of this. He got two chairs and stood up on them. Then he told Paul to stand up with Penelope, Paul did. Neither he nor Billy wanted to get out of her pussy or ass. So, they work together so Penelope could suck Mike's cock. The crowd went crazy while all three men fucked her mouth, her ass and her pussy.

Penelope was overwhelmed at first with all the three cocks. But, once she got in tuned with each sensation, she went to work. The cock in her mouth gave her the sweet tastes of fucking. She could taste his salty semen, her sweet nectar with a slight hint of highway, what a concoction.

Then there was Billy's thick cock stretching the walls of her coochie. That every time he pumped his dick in her, his wide penis would pull her clit in and stroke it. Driving Penelope to the edge of climax, then pulling his cock out just before her clit throws the switch.

Getting her ass fucked was a totally new sensation for Penelope. It was painful, erotic, dirty, good and bad mix all into one. She enjoyed the feel of a dick up her ass and the warm cumm that ran out. She loved the feel of one cock then a second. The feel of a hot nut, but, the dick still hard and fucking her ass. It was a new sensation ... it was new.

The four of them worked together with an encouraging crowd to reach ultimate gratification. The tasting of sweet fucking while he fucked her sweet mouth, the rolling of her clit as her pussy was being invaded by a fat cock. Thrusting and pulling while her cumm ran down her inner thigh, the taking of her last cherry, having her highway coat with warm semen, while the dick ran up and down her canal. Touching spots and igniting sensation she never knew she had.

When Penelope reached ecstasy she inhaled and put suction on Mike's cock which caused him to pump his cumm in to Penelope's sweet mouth. Her pussy gripped Billy's fat cock, massaged it and drained it of all its hot jism. Her ass puckered around Paul's cock, causing it to get ridged and fuck her ass hard. Her ass puckered again milking him of his man juice into her tender ass.

Penelope had cumm dripping from the corners of her mouth, seeping from her pussy and oozing from her newly fucked ass. The crowd clapped there approval as the pricks returned to normal. Her faithful limo driver was there to cover her up and whisk her away. But, Penelope had many more bars to visit...

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