A/N: I'm just going to skip to the story and you'll be surprised on who the pairing is. Also before I go into the story, I was dared into writing this story by a friend who I believe is a pervert and I hate him for making me write this, but oh well.

One Drunken Night

The home of the Maples was loud and flashing with light as a party that began at eight entered into its eight hour. The noise was loud enough that it angered many of the neighbors, but none of them called the police because they feared what a drunken Norman would do to them. Everyone who was everyone was there. The Maples, Ash and Delia Ketchum, Brock, Misty, Tracey, Professor Oak, Professor Birch, Dawn and even her mother was there as they continued to party.

Ash and his friends were fifteen, but by the second hour the party was so intense that the grownups did not know what they were doing. The grownups began to act crazy and the next thing the fifteen year olds were doing was drinking alcohol like crazy. Brock was even forced to jug about a keg full of beer down his throat with everyone yelling out, "Jug, jug, jug, jug!"

After Brock was done, he passed out as a light and fell to the floor unconscious from drinking all that beer. As of the third hour, everyone at the house was drunk and some were even passed out. Dawn was found kissing Max on the couch with her mom passed out on the couch with a bottle of beer in her hand. After a few minutes of kissing, both of them passed out on the couch with Dawn on top of Max sleeping on his chest.

Misty was next to Ash demanding him to kiss her, but Ash who was not as drunk as everyone else declined as he didn't want to do something he didn't want to regret. After minutes of Misty demanding Ash, she finally stopped and fell asleep on the armchair she slumped herself down on.

Norman and the Professors all walked outside around the second and half hour and have not come back since. They were later found knocked out by a drunken Caroline in the kitchen after they drank about three bottles of vodka each. About minutes after the second hour, Delia was stuck in the bathroom emptying her stomach out after two bottles of vodka. She then passed out right after Brock did leaving her stuck asleep in the bathroom.

May and Drew made out with each other before entering a room leaving them alone, but were later found out to be sleeping with each other underneath a sheet. Norman was furious, but found that they had their clothes on and just slept together ceasing his anger. After about the fourth hour, everyone was knocked out or asleep except for two people. Ash who was not as drunk as the others was sitting on the couch and looking around trying to stay awake. However, Caroline who was very drunk had different plans for the young Pokemon Master-to-be.

Caroline made her way to Ash, who turned to her, but was shocked to see Caroline setting herself on Ash's lap and kissed him right on the lips.

Ash eyes widened in shock as Caroline continued to kiss him waiting for some type of response from the young boy. Ash final gave in as he kissed her, putting his hands on her hips as he demanded entrance into her mouth, which she obliged. Ash slid his tongue into her mouth as they battled for dominance. Caroline broke the kiss as both began breathing for air with their foreheads touching each other. Ash then attacked her lips again as they continued to make out. Ash then felt his hormones take in as he sat up from the couch while holding Caroline by her waist and began heading toward the stairs. Ash began his climb up the stairs as they both continued to make out and Caroline put her arms around Ash's neck and crossed her legs over his waist.

Ash made his way toward a vacant room and locked the door behind him as he then laid Caroline onto the bed. He then crawled on top of her and kissed her passionately again as she put her arms around his neck. Ash broke the kiss as he began to trail his kisses down her neck and stopping at her collarbone before going back to her lips. Caroline broke the kiss as she began to take off Ash's sweater and then his black shirt to reveal his very tone and muscular body. The locked lips again and Caroline began to trace his body with her hand as Ash slowly began to unbutton the shirt she was wearing.

After he finished, he tossed the shirt away and saw the black bra that she wore, but resisted touching her breasts as he locked lips with her again. Caroline moaned into his mouth as he grabbed one of her breasts as they continued to kiss passionately. Caroline broke the kiss this time as she reached behind and unclasped the bra and threw it away to reveal her perfect breasts. Ash stared in amazement as he slowly descended and put her left breast into his mouth, while massaging her other breast with his hand. He began to swirl her nipple with his tongue causing the mature women to moan loudly as she felt pleasure course throughout her body. Ash then moved to the other breast and repeated the same motions causing Caroline to moan much louder.

Ash removed his mouth from her breast and locked lips with Caroline again as she moaned into his mouth. Ash broke the kiss as he began to trail down her neck leaving kisses behind. He kissed each breast before going down kissing her stomach and then her bellybutton, until he stopped at the skirt that blocked the most sensitive part of her body. He looked at her and watched her smile as he began to remove the skirt that revealed her black panties. He then removed the black panties to reveal her wet pussy. He leaned down to her pussy and stuck his tongue inside her vagina causing her to moan loudly with pleasure. He then put a finger inside her pussy as he continued to lick her vagina, before putting another finger in her vagina. Ash finally put in three fingers as Caroline moaned louder and he began to suck on her clit. Caroline felt nothing but pleasure as Ash continued to suck on her clit, now with tongue motion, and thrusting his fingers in her pussy.

Ash stopped playing with her pussy and went back up to kiss her on the lips as she wrapped her arms around his neck. She then felt something touch her sensitive spot as she knew it was Ash's cock. She moaned into his mouth and Ash knew what she wanted. He broke the kiss as he stood on her knees and began to take off the jeans he was wearing. He stopped when he saw Caroline take over as she began to remove Ash's jeans to reveal his boxers and his hard member that stuck out. She smiled at how big it was as she took off the last remaining piece of clothing on Ash's body. She then took his hard dick and began to stroke it with her hand as Ash moaned in pleasure. She was glad that Ash loved the way she stroked his member and knew he would love what she did next. She then began to lick the tip of his cock that made Ash moan louder. He sure never felt anything like this before and moaned even louder when Caroline took his whole member into her mouth. He moaned out her name as she bobbed her head up and down as she spit saliva on the tip and then putting his cock back into her mouth.

Ash felt like bursting, but before he could Caroline stopped sucking on his cock and laid back on the bed as he looked at her. She then opened her legs to reveal her wet pussy and motioned Ash to put his member inside her pussy. Ash gulped in nervousness as he positioned himself between her legs and rubbed his shaft with her vagina and looked up at her. She smiled and nodded as Ash entered her slowly as Caroline screamed and moaned in pleasure. She moaned louder when Ash's shaft went deeper inside, until Ash decided to take it out causing Caroline to whine. However, Ash entered her again as he began to thrust his cock in and out. He never thought that he would lose his virginity to his friend's mom, but his hormones caused him to continue as he continued to thrust. Ash locked lips with Caroline as she wrapped her arms around his neck and then wrapped her legs around his waist as he continued to thrust inside her.

"Faster..." She moaned as Ash thrust in a quicker pace as she moaned loudly at the pleasure the young boy was giving her. She couldn't believe the sex that she was getting from one of May's friends as he continued to thrust, but went faster when Caroline asked him to. Soon, both her hips and his began to be in unison as she moaned and he groaned. Ash kissed Caroline again as he continued to thrust inside as he tasted the cherry lipstick that she wore. He also tasted the alcohol that she drank, but the cherry lipstick soon made the taste of alcohol disappear. Ash then broke the kiss and went to suck on her breast as he continued to enter her. She now felt like she was in heaven when Ash sucked on her breast and didn't want it to stop.

However, every good moment in life had to end. Ash felt the same sensation when Caroline gave his cock a blowjob and he knew what it meant. "I'm..gonna..cum!" He told her as he continued to thrust.

"Me…too…" Caroline replied as she locked lips with Ash one more time. Then they both screamed into each other's mouth as they both climaxed with Ash's seed shooting insider her and her juices flowing all over his cock and onto the bed sheet. They continued to kiss even after their climaxes receded, until Ash broke the kiss. They both began to catch their breath as Ash slid his penis out of her and laid down on top of her. They both then fell asleep with each other in their arms, and boy were they in for a surprise the next morning.

Author Notes 2: I hope you guys don't think I'm a pervert. I blame my friend for making me write this and his stupid dare. Of course I could have said no, but we took an oath that we had to do each dare no matter what it was. Let me tell you, the next dare I'm going to give him I'll make it hurt lol. Remember Ash and Caroline were drunk, but Ash wasn't as drunk as Caroline and he could have stopped it, but his hormones got the best of him. Damn hormones, I blame science.