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.
