Boys Will Play

Jim sat on his bed wondering if this Saturday night would be any different to every other Saturday night in his 18 years on the planet. Sure it was his 18th birthday and sure he was throwing a party that night but what could possibly happen that would make his life different? "I could have sex, for starters" he thought to himself. Jim was still a virgin, even at the age of 18. As far as he knew nearly all of his friends had had sex at least once, he had even caught some of them in the act. And they all made it known that they had done it, who they had done it with and what they did exactly. He felt like he would never get laid.

"Tonight," he whispered to himself, "tonight's the night."

At 8:00pm the first guests started to arrive, all carrying cases of beer and bottles of spirits just in case the alcohol Jim was providing ran out. Jim's mother and father were away unfortunately but they had asked some family friends to chaperone, even though they trusted him they knew he couldn't be everywhere at once. The family friends were their neighbours, Jack and Carol Dawson, whose daughter Erica was at school with Jim, and Mike and Kim Willis whose son Tristan was in Jim's football team.

Carol Dawson was the epitome of the term M.I.L.F. She was 42, 5'4," 135 lbs with dirty blonde, shoulder length hair and deep blue eyes. Her breasts would have been close to a 34D before she had children (Jim had seen pictures) now they were enormous and had a slight sag that somehow made them even sexier. Her waist was still narrow and her figure tapered out to her luscious ass which was perhaps her best feature. And what a feature it was! It was like God had made a giant peach and put it where her ass was, it was just perfect. Kim was almost as sexy. She was 40, 5'2," 120lbs with very short dark brown hair which she always wore messy. Her figure was second only to Carol's; she had 32C breasts that were still perky (Tristan had been adopted), a very slim waist probably only 9 or 10" across and the cutest, perkiest ass in the history of asses.

By 9:00pm the party was starting to heat up, Jim was being given birthday kisses by girl after girl, maybe his luck was improving. He made his way past the guys doing tequila slammers to the lounge-cum-dance floor. The lights were dimmed and the music was pumping, there must have been 50 people crowded into the small room and the sexual energy was pumping through the crowd. He found himself dancing with Erica which surprised him because she had never really spoken to him all that much before. Her young firm tits jiggled in front of him as the pair (along with everyone else) bounced to the rhythm. Then he saw it, his gaze drifted over Erica's shoulder to see her mother and Kim pounding back some drinks. Carol's low cut top parted in just the right spot revealing two things, one was that she wasn't wearing a bra, the other was her nipple. The sight gave Jim a boner the size of the Eiffel Tower and Erica seemed to think it was because of her, so in her highly inebriated state she took him upstairs to get closer. They kissed all the way up the stairs, stepping on other couples and feeling their way to the nearest empty room. Just as she opened the door she broke the kiss and with wide eyes she said,

"I'm gonna throw up!"

luckily the room was a bathroom. Unluckily for Jim it looked like Erica was going to be out of action for the rest of the night. He made his way down the stairs and past the other couples, then into the kitchen where he took a shot glass and a bottle of Vodka and went to sit outside. The chilly autumn breeze whipped at his face but he couldn't feel it. He downed his first shot. The straight vodka burned his throat but he didn't care, he just wanted to get drunk. "I really thought that was it," he said quietly to himself, "I guess there really isn't any one out there for me." He downed his second shot and felt a hand on his shoulder. "Would u mind if I take a seat, Jim?" Carol asked. "Uh no, go right ahead." He replied. She sat down and poured some of the vodka into her drink, she was already very drunk. Jim poured his third shot of vodka. Carol started making chit-chat about life and school and work. Several shots later the topic of conversation moved to Jim's love life.

"Well I don't exactly have a 'girlfriend' right now, no" he said.

"That's a shame, is there anyone you've had your eye on?" Carol asked.

"Hmm, not really. I was dancing with Erica for a little bit but she didn't feel too good."

"Yes, unfortunately Erica can't quite hold her drink yet," she giggled, "But do you like her? I mean would you fuck her?"

Jim was taken aback by this brazen use of the word 'fuck', not to mention the question.

"Uh, I guess so...if the opportunity arose. Hell, I'd probably fuck anyone about now, I'm so horny!" Jim blurted out.

"Really, why's that?" Carol enquired.

"Well to be honest, I've never...really...fucked anyone before."

Carol's eyes suddenly sparkled like diamonds. "Really, what about blowjobs?" she asked.

"Um...no, never had one of those either." Jim replied.

"Hmm, interesting..."

For the next 20 minutes the conversation Jim and Carol talked about nothing in particular, then all of a sudden (and when she noticed the vodka bottle was empty) Carol stood up and said that she wanted to dance, and Jim was all too happy to oblige. They made their way into the kitchen, Carol supporting her self on Jim, where they bumped into Kim who said that as the party was starting to wind down Mike and Jack had gone home. Carol whispered something in Kim's ear and soon she too was making her way with her arm around Jim to the dance floor. It was almost deserted, except for a few couples slow dancing in the corner the three of them were alone. They began to dance in a little triangle but soon it turned into more of a cluster of legs and arms moving slowly to the music. Carol put her arms around Jim's neck she looked into his eyes, and then started to kiss him. He was surprised but kissed her back, after all she was the M.I.L.F. to end all M.I.L.F.'s. Carol's lips were suddenly pulled away and replaced with Kim's. He could tell how drunk she was by the sloppy wet kiss she gave him, it left a trace of saliva around his mouth. He then found Carol was kissing him again but she was licking Kim's saliva off the outside of his mouth. He reached out and felt her big soft tits, they felt amazing! He could also feel a hand feeling his ass and even a hand feeling his growing crotch.

"Let's go upstairs," whispered Carol. She led Jim by the hand and he in turn led Kim.

When they started kissing again, Jim realised they were in his parents bedroom. Kim dimmed the lights then came over to join them on the bed. They all kissed and touched for a little while before Carol got up and began to undress. She removed her low cut top, exposing her breasts and the slipped off her skirt revealing that she was wearing to panties. Her pussy was covered with a thick bush of pubic hair. Kim cackled at how naughty her friend was. Kim got up as well and began to strip revealing her perky tits and awesome ass. She had a neatly trimmed little bush covering her cute cunt. The pair giggled and caressed each other in front of Jim. Then when they saw his cock trying to break free of his pants they wandered over, sexily. They both dropped to their knees and Carol unzipped Jim's pants, then she reached in and pulled out his 7" hard on. She began to stroke it slowly and lightly but due to his inexperience and the incredible sexiness of these two women, he came almost immediately. Carol caught most of his cum in her mouth but some sprayed on her face, this was licked off promptly by Kim.

"It's true the first one does taste the best!" Kim cried. They ladies took Jim's clothes off and turned their attention back to his still hard cock. Kim jerked it while Carol licked and kissed the tip and sucked his balls.

"Do you like having your cock sucked?" she asked in a deep sexy voice.

"Yes, ma'am." Jim replied.

"It sure beats jerking off doesn't it?" said Carol in between sucking.

"Oh god, yes!" Jim cried.

"Do you jerk this hard cock much? I bet you jerk it all the time," said Kim as she pumped his cock, "tell me all the filthy things you think about while you jerk this fat cock off, you dirty little boy!" Jim started to tell the ladies all the dirty things that excited him and they seemed to get just as excited. Carol started to deepthroat Jim's cock as she got more excited. He was about to cum and both women could sense it.

"Yeah cum right down her throat, make her your whore. Make us both your whores!" Kim cried. Jim did as he was told a quickly came down Carol's throat. It felt like he pumped gallons of cum into her and he started to pull out so he could leave a little bit in her mouth. As his cock left Carol's mouth Kim's tongue entered and they shared a sticky wet kiss, licking each other until all of Jim's cum was gone. Then without a word Carol pushed Jim onto his back and crawled up next to his head and straddled his face.

"Now Jim I want you to eat me out, pay close attention to that little thing that sticks out, that's my clit and don't forget to stick your tongue in my hole." She lowered herself onto his mouth and let him taste his first cunt. He loved the fact that she was so hairy, it really turned him on and while this was going on, Kim had started licking his cock and sucking his balls trying to get him hard again. She didn't have to wait long. Soon she was stroking a proud, hard, throbbing young cock with her soft mature hand. The air was filled with Jim's moans and Carol's cries of

"Oh yes Jim! That's amazing! Keep going! Tongue your old slut's hairy cunt!" Kim positioned her pussy lips above Jim's hard young prick and teased it by pushing it forward and rubbing her clit along its length. Carol was getting hysterical as she reached climax, "UH YEAH TONGUE-FUCK ME! THAT'S IT MAKE MOMMA CUM! GOT IT'S BEEN SO LONG! IM CUM....CUM....CUUUUMMMING!!!"

Carol rolled off Jim's face when her orgasm had subsided and she was able to move again. Kim was still teasing Jim's dick with her clit and the both of them were just about ready for Jim's first cunt. She leaned forward and kissed him, tasting her friend's cum on his lips, then sat up and positioned herself just inches above his throbbing, pre-cum dripping cock. She parted her soaking wet lips and plunged herself down onto his cock. It was amazing! She drew herself up again then impaled herself once again. Jim could barely comprehend how great it felt. Her cunt was so hot and wet and soft, and the muscles contracting around his prick felt fantastic. Kim was already about to cum, after only 30 seconds fucking. Jim rolled over on top of her as she hooked her legs around his ass and pulled him into her chasm. Her orgasm subsided but he kept fucking her. She had never kept fucking after an orgasm; she told him to stop but her second orgasm quickly shut her up.

"Oh fuck yeah, keep pumping me with your hot cock! I'm your mature whore, make me your fuckslut! Cum in my holes like I'm nothing to you! USE ME LIKE A FUCKING PIECE OF SHIT! UH! UUUH! OH FUUUUUUCK!!!!" screamed Kim. The two of them were dripping with sweat and Kim's tits were heaving. Carol was now back in the game and she was horny again. She pulled Jim out of Kim's cunt and they left her there to sleep. She led him down the hall to his bedroom. His cock was still hard and he had not cum in a cunt yet so he was trying hard not to jerk off. She laid him down on his bed and left the room, only to return a few minutes later wearing one of his mother's dresses.

She staggered over to him, "Oh my Jimmy, what a big penis. Want momma to help make it feel good?" she said.

"Yes mommy. I want to put it in your hairy wet cunt." Jim replied.

She lay down next to him and said "Get on top of me and fuck me like that slutty whore mother of yours." Jim didn't need to be told twice. He got between her legs and slid his hot shaft into her bushy soaking twat. She moaned like a whore as Jim fucked her cunt, and both fucking her in his own bed and fucking her while she was in his mother's dress made it even more erotic. It didn't take him long to cum inside this hot little nympho and she was ready to climax too. They rocked back and forth as they screamed and moaned in ecstasy. They took a short break so that Carol could have a cigarette and Jim could have a drink. When he came back from the kitchen Jim saw that Carol had found a jar of Vaseline in his draw and she was liberally applying it to her puckered asshole.

"You're gonna fuck my asshole, stud" she told him. He ran over to the bed and put some Vaseline on his hard schlong. Carol got up on her hands and knees letting Jim get up close behind her. "Now you be careful back there, hon" warned Carol. He pushed his slippery purple cock head into her pink asshole and inched his way up her back passage. As Jim moved into Carol's warm body, her hole stretched wider and wider and she moaned louder and dirtier,

"God yeah! That's it! Fuck my tight ass, I can feel the hole stretching around your thick, hot young manhood! MMM!"

She started frigging her clit and shaking about on the bed, she was screaming with pleasure her ass was contracting around his dick as he pumped in and out of her wide-stretched hole. He could feel his orgasm building and he grabbed two big handfuls of flesh and he fucked her harder and faster, he was sweating and panting but having the time of his life. She too was bucking into her lover and sweating as she screamed and came to an earth shattering orgasm. Jim let his seed flow into her as they collapsed on their side still joined in sexual ecstasy.

Jim woke the next morning to find himself still inside his lover almost 30 years his senior. He waited for her to wake up and then they showered and made their way downstairs, Carol walking somewhat gingerly due to their activities the previous night. They walked into the kitchen but their smiles faded when they saw jims parent sitting around the table with Kim...