Hello this is my first Fanfiction, This is for one of my favorite pairings in Pokemon that being Ash X May also known as Advanceshipping. I hope you enjoy.


It was the end of the Indigo Pokemon League competition, and Ash Ketchum had won the whole event after a fierce battle. He was cheered on by May who had been traveling with him through Kanto so he could re-challenge the Kanto league and she re-challenged the Kanto contest circuit and won the grand festival

Ash had told May his feelings about 2 years ago when he went to visit her in Hoenn. The 2 soon started dating and traveled through Hoenn again, with Ash coming out on top in the Hoenn League and May in the Hoenn Grand Festival respectively. A year later Ash asked May if she'd travel around Kanto again with him, May happily accepted and they traveled through Kanto again.


Ash and May were both now 18 and their appearances had changed quite a bit. Ash had grown a lot taller and was muscular due to working out a lot, other than that he looked mostly the same. May still wore her usual outfit and bandana but her hair was a bit longer, she was a little taller, had a slightly more athletic build and had become very busty in all the places the guys would like


After going onto the stage to get his trophy, May had come up to him and kissed him on the cheek


May: You did it Ash, I told you that you could win. May shouted in Happiness


May hugged Ash tightly almost squeezing him


Ash: T..thank you May, (he hugs her back)


May: oh Ashy that was wonderful


Ash: He-he it was nothing May honestly, I couldn't have done it without you, Pikachu and the others


May: oh Ash you're so sweet


Ash: It's just how I am Mayday


Ash and May leaned in closer and eventually their lips connected, engaging in a beautiful and passionate kiss. May Moaned in great pleasure


May: Oh ash, follow me I know how to celebrate your big win


Ash: Alright May, lead the way


May grabbed ash's hand and led him to the Pokemon center


Nurse joy: Hello you 2 congrats on your big wins


Ash and May: Thanks Nurse Joy


Nurse Joy: What would you 2 like for me to do for you?


May: We need a single big sized room if it's available please


Nurse Joy: Oh it's certainly no problem, we already have one reserved for the Champion. Follow me


They followed Nurse Joy down the hall and into the room


Nurse Joy: Here you two are enjoy your stay tonight


Ash and May: Thanks Nurse joy


Nurse Joy: Anything for the Champion and the Princess of Hoenn


Nurse Joy left the two alone


Ash and May walked to their room, unlocked the door and got inside. May locked the door, and went up to Ash giving him another embrace. Ash embraced her back and then asked her a question


Ash: So May how were we going to celebr- mmf


Ash was cut off by May's lips


May: I'm going to give you the best present Ashy you deserve this after all the stress you endured


Ash was Surprised by May's statement, He looked into her eyes and could see the lust


Ash: O-okay May show me


Was all Ash could mutter before May kissed him fiercely on the lips again and began the celebration for her beloved Ashy. May and Ash continued to Kiss and May started to move her hands all over Ash's body as Did Ash. May soon worked her hands down ash's body and stopped at his crotch. After kissing him once more she grabbed at Ash's crotch and began to rub it through his Pants. Ash moaned at the touch of May's hands on his Penis, her hands felt warm and wonderful


Ash: Oh May that feels good please don't stop


May continued to rub at Ash's crotch making him feel great pleasure, suddenly May stopped


Ash: Why did you stop May?


May: How about I make this easier for Me


Ash: Wha?


May then pulled down Ash's pants and left him in his boxers. May instantly noticed the bulge in Ash's Boxers and was shocked at how huge it was and then began to giggle


May: Woah Ash is that a Metapod in your boxers or are you just that happy to see me?


Ash blushed at the sight of his erection, truth be told May really just turned him on that much. May then got on her knees so Ash's bulge was facing her, She continued to rub his penis more and more, the more she did so the more Ash Moaned in Pleasure. After a while May stopped and looked at the bulge, She knew what She wanted to do next. May then looked up at Ash for approval. Ash nodded at May, telling her that She could proceed. Upon seeing Ash Nod, May pulled his boxers down revealing his big Metapod


May: Holy crap Ash this thing is huge


May Was surprised at how big his member was, it looked to be 7 inches long


May was in awe at the size, soon her hormones kicked in, she wanted it more than ever now


May then asked Ash


May: May I suck it?


Without hesitation, Ash replied to May


Ash: Go ahead May


After receiving approval, May put her hands on his member and started kissing it lightly, she was only warming up for what was to come. May stopped kissing Ash's member and got in position, She began to lick it like a lollipop for a bit, after this She took his member in her hands and was ready. May then began to slowly suck Ash's member, Ash moaned on the contact of May's mouth on his member. After a little bit, May began to move his penis in and out of her mouth faster. She got the hang of it pretty quickly, Ash was moaning in pleasure, May knew she was doing good


Ash: Oh god May that's good don't stop


May then started to bob her head up and down on Ash's member fitting all of it in her mouth. Ash was stunned by how well May was doing, She was like an angel


Ash: Wow May, You said this is your first time?


May suddenly took Ash's dick out of her mouth to answer him


May: It is my first time, am I doing okay Ash?


Ash: Yes May, You're doing wonderful, please don't stop


With that May resumed sucking ash off, for a beginner She was sure doing it like a pro


Ash: OH MY


Ash screamed in delight, May had found a sweet spot


Ash: Oh yes May right there, right there May


Ash: UGH MAY I'M GOING TO..


May looked confused but suddenly Ash had reached his climax. Ash came into May's mouth, his seed going down her throat. Ash looked at May with a worried expression, May didn't look very pleased at what had just transpired


Ash: Oh geez I'm sorry May I didn't mean i-


Ash was cut off by May putting her finger on his lips


May: It's fine Ash, I wanted that.


May then began to lick up the cum on her face, She admired at how good it tasted. After being reassured by May, Ash had calmed down, though May noticed that he still felt a bit uneasy. May then embraced him once more in an attempt to calm him down, she brought him to the bed and she laid down on the bed


May: It's your turn Ash


Ash: Alright then, time to go deep


Ash kissed May once again and began to rub May's Breasts while he did so. Ash then tugged at May's shirt and pulled it off and then undid her bra, revealing her pretty big boobs


May: Go ahead Ash, You have my permission


Ash grabbed at May's boobs and squished them a bit, making May moan. Ash then started sucking on May's nipples as she moaned loudly


May: Oh Ash your so good


Ash then began to pinch her nipples making her moan even louder


May: AHH ASH


Ash continued to play with May's breasts, May held onto Ash as he did so


May: Oh man Ash, that feels so good


Ash continued to suckle on May's nipples before he finally stopped. Ash went to pull down May's pants, before he did he looked up at May for permission


May: Go ahead Ash, I trust you


With permission given to him, Ash then pulled down May's pants and panties. He stared at her pussy, admiring it's features, it looked so pretty and perfect, he could also see that May shaved. Ash then took his finger and inserted it into her Skitty, he realized that she was very wet


Ash: May you're pretty wet down here


May: Hehe well I couldn't help it Ash, you really turn me on sweetie


Ash continued to finger May's pussy, it felt really nice and soft


May: Oh Ash, that feels great, keep going please


Ash continued to finger May's vagina but at a faster rate, he began to use his other hands to massage her breasts


May: OH ASH YES


May: OMG ASH THAT FEELS WONDERFUL


May: ASH I'M GOING TO CUM


May then squirted her juices on Ash. After licking May's juices off his face, Ash had moved closer to her, his member close to her Pussy. May had a worried look but knew

that she'd be okay because Ash wouldn't let her get hurt


Ash: May..are you ready?


May: Ash..I..I think I'm ready


Ash could sense May's worry from a mile away, he leaned down and kissed her on the lips in an attempt to calm her down. May then laid down and braced herself for Ash to enter


Ash: Okay May I'm going to enter now


Ash then entered his member into May's pussy


May: Owww it hurts: May winced out in pain


Ash looked concerned and stopped sliding in and out of May


Ash: May do you want me to stop? Ash asked concerned about May


May: No it's okay Ash keep going


Ash: Are you sure?


May: I'm sure Ash


Ash then slowly began thrusting in and out of May again. Eventually the pain went away. Once it did, May started to feel great pleasure


May: Oh ash that feels great. May Moaned


Ash then sped up the pace moving in and out of May at a lightning fast speed


May: OH ASH YES RIGHT THERE


Ash had found a good spot and was loving every second of this


Ash: Oh may I'm going to cum again


May: No Ash pull out


Ash pulled out of May, and took a break to catch his breath. May laid there with him catching her breath before they continued. May cuddled up to Ash so she could not only rest a bit but because she wanted to feel his "sexy" body. May and Ash kissed for a bit before May was finally ready to continue


May: Ash I'm going to get on top of you okay?


Ash nodded in agreement as May sat on his member. May began to bounce up and down on his member as Ash began to grab her boobs and fondle them


May: Ahh ash


Ash: God May you are so good at this


May continued to ride ash but then she had an idea. She stopped bouncing up and down, confusing Ash


Ash: Why did you stop May? Was I to rough?


May: No Ashy I just wanted to turn around and ride you with me facing away from you


Ash: Oh well alright then May


May then got on Ash from behind with her Ass facing him. Ash was in love at the sight of her amazing Ass, he wanted to feel it. Ash then smacked her Ass


May: Oh ash your being a naughty boy


Ash: Sorry May, you just have an amazing Ass


May: Hehe I know I do, I'm glad you love it Ash


May then started bouncing up and down his member again but surprisingly at a faster pace. Ash then grabbed her ass and started Squeezing it. Ash kept playing with

May's ass, it was as if it was hypnotizing him


May: oh Ash don't stop


May was enjoying every second of this, she loved it when Ash played with her ass, his hands felt warm and soft. Ash continued to squeeze and spank May's ass. May continued to bounce up and down on Ash's member, eventually she sensed that he was going to cum again, so she got off him


May: I don't want you to cum yet ok Ash?


Ash nodded in agreement


May: Ash...that was wonderful. May said as she got off him


After getting off of ash, She needed another break, she once again snuggled up close to Ash. Ash welcomed her and brought her in with a strong embrace, he felt all around her body. To Ash her body was just perfect, her ass, her breasts, her flat stomach, her curves, her soft and cute looking pussy and those ever so sexy legs. Ash just worshiped her body, in his eyes it made May the perfect girl, her cute and sweet personality combined with her sexy body was a match made in heaven


May loved And worshiped Ash's body as well, he had grown taller and muscular over the years, she also adored his caring and goofy personality, her Ashy was the perfect guy for her


Ash continued to feel around May's body, occasionally spanking and squeezing her ass as well as groping her breasts. May loved it when he did, it made her feel great pleasure and she enjoyed every second of it. Suddenly May got on top of Ash again, and they started to make out. During this make out session, Ash continued to play with May's ass, and May started to kiss all over Ash's body, even sucking on his nipple. Eventually May got off Ash and went back to cuddling with him, they cuddled for what seemed like hours


After a few more minutes of cuddling, May had stood up on the bed, Ash was lost on what she was doing


Ash: what are you doing May?


May: Ash there is one more thing I want to try


Ash: What's that Dear?


May then put her ass in front of him and pointed at her hole


May: I want you to fuck me in my ass Ash


Ash was stunned at What May had asked him, he was also very anxious about it


Ash: A-are you sure May?


May: I'm sure Ash, don't worry it'll be okay


Ash: well..okay I don't want to hurt you though, I'd never forgive myself if I did


May: Silly that's what the lube is for, I'll be ok I promise Ashy


May handed ash the lube and got on all fours, she was ready but also a bit scared as it was her first time but she knew Ash wouldn't hurt her. Before ash applied the lube he decided have some fun with May by teasing her. Ash licked May's asshole, surprising her greatly. She let out a loud moan, then decided to tease him


May: Oh Ash you little pervert: May said teasingly


Ash couldn't help but smile, as he started putting his tongue into her asshole


May: oh my god ash, that feels wonderful


Ash then stopped, he felt as if he had teased her long enough and was ready to fuck her asshole


Ash: Alright May I'm going to insert it now, are you ready?


May: I'm ready ash


May replied with an obvious tone of worry in her otherwise sweet voice. Ash didn't like when her voice wasn't in her usual sweet tone, it made him feel very uneasy.

Ash hesitated to go on, out of fear of hurting his beloved Mayday


Ash: M-May I don't know if We should do this


May: What's wrong Ash?


May looked back at Ash, one look at his eyes and she instantly knew what was wrong, she saw the worry in Ash's eyes. Thinking fast she went up to him and hugged

him tightly, she wanted him to calm down


May: Ash..don't worry you won't harm me


Ash: I don't know May, I mean I hear this is very painful.


May quickly kissed Ash to shut him up and reassure him


May: Ash look at me


Ash looked at May, waiting for her to speak


May: Ash you are the sweetest and most caring person I know, you won't harm me I promise


Ash didn't respond, as he knew she had something else to say


May: Ash I trust you ok?


Ash: Alright then May, Let's do it


May: Let's get started then


Ash felt much better now and was ready to do this, May got back into position. Ash applied the lube onto his penis and into May's Asshole, to ensure that he wouldn't

hurt her. After waiting for a few seconds to calm himself down, ash was ready. Ash then inserted his member into May's Asshole, she gasped in pain


May: Owww it hurts


Ash: May are you ok?


Ash had suddenly stopped


May: No it's okay ash, continue honey please


Ash wasn't so sure, but he was willing to do anything to make May happy, he himself also wanted to do this, so he pressed on. Ash then began to thrust in and out of

May's anus slowly. May soon felt less Pain and eventually none at all, the pain had been replaced with pleasure


May: Ash you can go a bit faster now


Ash: Suit yourself May


Ash sped up his thrusts, May was loving it, they both were. May could really feel Ash's member in this position, and decided to make a comment about it


May: Oh wow Ash You're so big


Ash: I know I am May


Ash responded pretty proudly to her, and he kept on fucking her in her Ass. Ash began to spank her ass once again, May was of course very pleased with this course of action. Ash to thrust in and out of her, speeding up his thrusts every now and then. Ash Spanked May's ass really hard, making her scream in pleasure


May: YES SPANK MY ASS ASH


Ash: Hehe your ass is mine May


May: IT'S YOURS ASH YOU CAN DO WHAT YOU WANT WITH IT


Ash had really gotten May riled up, and had not realized how loud they had been. Ash then remembered that the Pokemon center rooms really muffled out the sound. Ash continued to fuck May in her sweet and juicy asshole


May: Oh my god Ash keep going YES YES


May felt like she was at her climax


Ash: M-May I'm going to cum


May: IT'S OK ASH DO IT INSIDE ME


Ash: MAYYYYYY


Ash screamed as he climaxed into May's Asshole. Ash took his member out of May and collapsed on the bed and she curled up next to him. They embraced each other, pretty tightly at that


May: Oh Ash that was..wonderful


Ash: It sure was heh


May: You have quite exceptional stamina Ashy


Ash: As do you Mayday


They laid there for about a minute more before May spoke again to break the silence


May: Ash?


Ash: Yes May?


May: I love you Ash


Ash: I love you too my sweet May, this has been one hell of a night for me, thank you


May: You're Welcome Ash, you deserve it, You're the Champion after all, my Champion. May Giggled


May then got on top of Ash, and embraced him again, wanting to sleep on top of him


May: Ash can I sleep on top of you?


Ash: Of course May, I don't mind


With that May laid on top of him, put her arms around Ash and closed her eyes ready to sleep. They kissed one last time as they then fell asleep in each others arms naked


It truly was a night worth celebrating, Ash had it all


Thanks For Reading, I've had this story written since around 2018 or so and haven't published it till now, I hope you enjoyed.