Mary had always been a bit of a tart. In fifth grade, her little brother Andy, then in fourth grade, had caught her with a boy behind a tree on the school grounds. They had shooed off her brother and her boyfriend had gone back to what they were doing until the bell rang ending recess. Despite this and many other playful encounters with boys, at 18 Mary was still a virgin, but a virgin with urges who loved spending time with boys flirting and petting whenever she could.
She especially liked to spend time with older boys, the seniors at the high school she attended. They liked to do wild exciting things and Mary enjoyed the attention they showed her. One night she had been out drinking and making out with one of the seniors, Mike. He had gotten her half naked and almost ready to fuck, but had ejaculated as she stroked his cock and ended their play. She had stayed out late that night, too late and when she came home after midnight smelling of beer was caught by her mom. Mary was grounded for a month, no dating, no parties, no after school anything! Her life ceased and she began trying to find ways to release her pent up energy. She tried masturbating and it helped some but she still felt the urges. She even experimented inserting various object into her pussy while she rubbed and it felt good though she had pain a couple times. After two weeks she was so hot she couldn’t stand it, she hatched a plan to get out of the house and see some boys. “Mom, can I take Andy to the movies tonight? He really wants to go” she pleaded. Her mother thought better of it but relented.
As they left the house she explained to her now 14 year old brother that they were not going to the movies, but would be going to have some fun with a friend or two. She had called Mike and told him to meet them at the park which was on the way to the theater. Andy could come along and he would get to drink some beer and hang out. He agreed it was OK. He liked to hang out with his sister and her friends. When they got to the park, there was Mike along with three other seniors, Pete, Jim and J.L. Mary was a little surprised but Mike explained that the four of them had already made plans to hang out before she had called. He couldn’t very well blow off three buddies for a sophomore. In reality, Mike had called the others after Mary had called him relating the story of how close he had come to fucking her on their last date and figured they could give Mary a “Train Ride”. Of course his three friends had jumped at the prospect so here they all were together at the park with a couple cases of beer in the trunk of Mike’s car.
“We can’t hang out and drink here” Mike told Mary “too many cops around. We’ll get busted. I know a place out by one of the canals, it’ll be fun. By the way who’s the kid?” “This is Andy, my little brother. He’ll be coming along. He wants to have some beer too. Don’t you Andy?” she replied, hoping the boys would let Andy come. Otherwise, she would have to take him home and wouldn’t be able to have fun with Mike. Mike thought about it. He didn’t like the idea of dragging a kid along, but he figured a couple guys could keep him occupied while the others were having a good time with Mary. An evil thought came to him and he grinned. “Are you cool Andy? You wanna hang out with us tonight?” he asked Andy. The 14 year old nodded, smiling. “OK then, everybody hop in. Andy you sit in the middle up front. Pete you drive. Mary you climb in the back with J.L. and me”. He went to the trunk and grabbed a couple six packs and returned hand each of the six a beer. He opened his and took a swig sliding in beside Mary while J.L. slid in on the other side. “Let’s head for the bee hives, the back way” he told Pete as they pulled away from the curb. This longer route to one of their favorite spots would give him time to get Mary going.
Mary sat in the back between Mike and J.L. She wore a short full skirt and button up blouse over her white bra and panties. She was a nice looking sophomore Mike had to admit with nice B cup boobs and shapely legs that now sitting in the car were mostly naked as her skirt was pulled up past mid-thigh. She watched Andy’s head as he tilted it back taking a sip of beer as the older boys encouraged him. Mike slipped his arm across the seat back behind Mary and rested his hand on her shoulder. He took another swig of beer and moved in to kiss Mary, holding the beer in his mouth. Mary accepted the kiss and was surprised as Mike released his drink into her mouth. She was surprised, but she accepted the beer and swallowed. She took another drink of her own beer and swallowed it as well. Mike took another swig and placed his beer bottle between his legs. He then turned once more to Mary to give her another beer kiss this time placing his right hand on her knee. The touch excited Mary, though she wondered about J.L. and the other boys. What would they think of her making out with Mike?
“J.L., give Mary some of your beer” Mike said, again surprising Mary. J.L. took a big swig and pulled Mary’s head to face him. Mary pressed her lips to his and accepted the beer from his mouth. His lips lingered on hers and his tongue slipped between her lips. His hand slid from her face down her body brushing against her boob and coming to rest on her other knee, opposite Mike’s. Mary wasn’t sure what was going on, but her pussy was dripping wet and the beer was relieving her inhibitions. She was enjoying every sensation. Mikes hand slid up her thigh to the hem of her skirt as he gave her another beer kiss, this time from her bottle. She had raised the bottle to his lips at his request as both his hands were busy caressing her shoulder and thigh. J.L.’s hand slid up her other thigh and slipped under the hem of her skirt. She parted her legs and J.L. could feel the heat emanating from further up. So could Mike. They continued giving Mary beer kisses from her bottle and J.L.’s. When hers was gone, Mike told her to grab his from between his legs. As she reached for it, she noticed the telltale bulge in the front of his pants. She glanced over at J.L. and saw a similar bulge. She was so hot she didn’t care. She knew she wouldn’t be a virgin after tonight.
By the time they arrived at the bee hives alongside the canal, Mary had drank most of three beers and was feeling buzzed. Mike had his hand rubbing her still panty covered pussy and J.L. was squeezing her titties through her shirt and bra. Pete had been watching the show in the rear view as he drove and Jim watched over the seat back. The only one oblivious to the goings on in the back seat was Andy, who being only 14 was also buzzed after two beers.
“You guys get out and have some fun” Mike told everyone as Pete parked the car. “Mary and I want to, uh, talk” he grinned, kissing Mary. He pushed her panties aside and slipped a finger into her steamy cunt hole. Mary moaned and spread her legs farther as the other boys got out. Mike pulled his finger out and began to unbutton Mary’s shirt. She didn’t resist, in fact helped him remove her shirt and bra. She moaned again as he fondled her naked teenage tits. Mike began kissing her hard and passionately as he pushed her back onto the car seat. When he slid his hands to the waistband of Mary’s panties, she raised her hips allowing him to easily remove them.
Mike pulled her panties off exposing Mary’s hot wet cunt. He could see her juices glistening on her pussy lips, which parted as she spread her legs welcoming what was to come. Mike wasted no time, he was not going to cum this time before getting his cock in that cunt. He opened his pants and slid them down to his knees along with his boxers. He crawled on top of Mary and positioned his six inch cock at the entrance of her cunt hole. Mary moaned as his cockhead entered her pussy. He pushed in, deeper and deeper. Finally he hit the barrier of her maidenhead. It was only partially intact having been punctured by some of Mary’s earlier experimentations. The pain she felt as he pushed through what remained of her hymen was quickly overshadowed by the pleasure she experienced as his cock buried itself deep in her virgin pussy. Mike began to quickly fuck her once virgin hole and Mary was quick to cum. She soon howled as her body shook with her orgasm. Mike could feel her pussy clamping down, but he kept fucking. In and out he pounded her cunt for another good ten minutes. Mary was once again on the verge of cumming when Mike groaned and let his hot seed pump into her hot cunt. She whimpered as he pulled his flaccid cock from her cunt and began pulling up his pants. Mary wanted more. She wanted badly to cum again. “Wait here a minute” Mike said as he got out of the car. Mary rubbed her pussy, trying to get herself another orgasm.
Mike got out of the car walked round to the trunk and grabbed a beer. “J.L., your turn” he called and J.L. came running to the car. He and the others had been standing on the canal bank throwing empty beer bottles in the water and then throwing rocks at them. To the seniors’ surprise Andy was hitting more bottles than the rest of them combined. He was a natural. Mary lay back rubbing her cunt when J.L. opened the car door and crawled in. She felt like a slut rubbing her cunt in front of him, but wanted to cum so bad she didn’t care. J.L. removed his pants revealing a cock equal to Mike’s and Mary reached for it, guiding it to the entrance of her womb. She cried out in relief as he pushed his turgid cock deep into her waiting cunt. An electric shock of pleasure jolted through her as his pubic bone mashed her clit to her own. He kept his cock deep and started grinding his pubes into hers. She soon cried out as she came once more and her cunt filled with more of her girl juice. J.L. felt her pussy clamp down on his cock and watched her face as it contorted in orgasmic bliss. He then began to pump in and out of her pussy pounding his pubis hard into hers. Both grunted with the exertion as Mary began to push her hips up to meet his thrusts. Mary reached the brink once more and eagerly fell over into the well of her orgasm, the shock waves emanating from her cunt out to her whole body. J.L. slowed for a moment allowing Mary to enjoy her climax, but soon began pounding her cunt once more with passion. In a few minutes he too was spilling his load deep in Mary’s hot cunt and slipping his now flaccid cock out. He picked up his pants and slid them on as Mary lay on the seat, cum seeping from her pussy down over her asshole and onto the seat. “Two down and two to go” J.L. said grinning at Mary as he got out of the car. He called to Pete who came running and then he joined the others on the canal bank.
Pete climbed in the car with Mary, who was beyond caring at this point. She just wanted more cock and more cum. She didn’t care who, she just wanted to be filled. Pete pulled his five inch pecker out and moved over on top of her. He pushed his prick into Mary and she groaned as pleasure once again filled her hole. Pete was excited when he first saw Mary spread on the seat before getting in the car and his excitement grew quickly as he began pumping his smallish cock in and out her slick, well used hole. He came in just a dozen thrusts, spewing his sticky juice into an already overflowing cum dump. Mary sighed and whimpered as he crawled off and got out of the car. It was Jim’s turn. Mary hoped he would give her the orgasm she still so badly needed. Jim got in and started pumping Mary’s hole she was once again lost in lust searching for a climax. Jim’s cock moved in and out of her easily, he was not as big as Mike but much more satisfying than Pete, and at least he was lasting. She began to encourage him to fuck her harder and faster, her heat was rising.
Mike looked over and saw the car rocking and knew Jim was fucking Mary, he needed to move quickly as he wasn’t sure how long Jim would last. “Why don’t you go see if your sister needs another beer?” he said to forteen year old Andy with a big grin. J.L and Pete looked at him in disbelief, but soon began smiling and telling Andy he should check on his sister. Andy complied walking slowly over to the rocking car. He looked in the window and saw Jim’s ass and balls as he pumped mercilessly at Mary’s cunt. He knew what they were doing, he’d seen pictures in his brother’s magazines. While his balls sported only sparse pubic down, his pecker began to rise as he watched his sister take Jim’s cock. He could hear her calling for Jim to fuck her harder and faster. As Jim pumped his seed into Mary’s cunt she opened her eyes and saw Andy’s face plastered to the car window. She was in full heat and whined as Jim pulled his shrinking prick out of her hole. She still wanted to cum. Mike looked down at Andy, surprised to see the bulge on the front of Andy’s pants. “Shit, the little fucker has a hard-on, he wants to fuck his sister” he called.
As Jim crawled out of the car Mike encouraged Andy to pull out his cock and climb in. “Look at her, she wants it” he said as Mary continued to finger her cunt looking for a final orgasm. She had gone well beyond caring who fucked her as long as she got fucked. Andy was drunk and his cock was thinking for him. He saw the naked pussy in front of him and pulled out his cock. “Fuck, he’s bigger than you, Jim! He’s gonna have a monster that one” Mike called out. Andy climbed in and put his cock at the entrance to his sister’s hot slick pussy. He could see the juices leaking out between the lips. He climbed on his sister and shoved his dick into her. Mary looked up to see who was fucking her now. “Oh fuck, it’s Andy” she thought. She realized how dirty and depraved it was and the thought of that excess put her over the edge. She began cumming harder than ever, and as her climax subsided it was followed by another and another. She was cumming so hard she couldn’t stand it. Andy kept pumping her cheered on by the four seniors behind him. After several minutes of Mary’s near constant orgasm Andy’s balls swelled and pushed his first cum deep into his sister’s hot pussy and she passed out at the culmination of a night’s pleasure.
When Mary came to, Mike was just finishing pumping a final load into her well oiled cunt. He had gotten hard watching Andy fuck his sister and fucked her unconscious body to get one last bit of relief. The others were sitting on the canal bank pouring beers down their gullets and feeding them to Andy who now sat in a drunken stupor. Mary finally got out of the car and walked to the front of it not bothering to cover herself. She squatted and peed what seemed a half gallon. Her lips were dry and she walked to the trunk grabbing the last of the beer. She gulped it down greedily then went and retrieved her clothes from the car and began to dress. She couldn’t believe she had done it. She had wanted to fool around with Mike and ended up fucking four seniors and then her own little brother, oh fuck, how wrong it was, but how good it had felt. She knew there was no turning back, she was going to end up fucking lots of guys now. Word would spread and they’d flock to her. She’d be able to pick and choose those who she’d let have her, but she’d probably fuck them all. And the thought excited her.
The next morning Andy woke with a terrible headache. Every sound felt like his head would burst. He flipped back the covers and was knocked back by the smell. His underwear seemed to be sticking to his privates and it smelled like someone had been cleaning fish in his bed. He grabbed some fresh underwear from the drawer and made his way to the bathroom. The shower felt great and relieved the ache in his head somewhat. All he remembered from last night was drinking some beer, and throwing some rocks. “This must be a hangover” he thought. “I’ll talk with Mary about it later”. He dried and put on his underwear then brushed his teeth and went to his room to dress. Mary was not so lucky as Andy. She remembered each and every detail of last night’s debauchery especially the part where she’d cum continuously as her little brother had fucked her and passed out as he spewed his load inside her. She had showered before going to bed, but her cunt still felt hot and sticky as she thought of all the fucking she had done. She lay in bed and began to stuff her fingers up her twat as she remembered Andy’s face as he came inside her. The memory of his face and the thought of how dirty and depraved it was rushed her quickly to climax and she moaned as her orgasm wracked her body.
After breakfast, when they were alone together, Andy asked Mary about last night. “Did we get drunk? Did we have a good time? What happened? All I can remember is drinking some beer and throwing some rocks at bottles” he said looking to see if she would tell him. “Oh, we all had a good time little brother, and you were the life of the party. The guys all think you’re cool and we’ll have to do it again real soon” she replied. Her pussy began leaking juices again as she thought of her little brother’s hard cock pounding her cunt. “Yes they would have to do it again” she thought.