Yes, there are quite a few. You can start by looking on fanfiction websites like FanFiction.net or Archive of Our Own. Just search for 'pokemon ash and may date' and you'll find a variety of stories with different takes on their relationship.
One great Ash and May date fanfic is 'A Day in the Park'. It beautifully depicts their day out, with Ash being a bit clumsy but endearing, and May enjoying every moment. Another is 'Under the Starlit Sky' which has a more romantic setting for their date. It shows their relationship evolving in a very sweet way.
You can expect different things. Some might have a lot of cute moments between Ash and May, like them sharing a meal or walking together in a beautiful Pokemon - filled landscape. There could also be some conflict, perhaps from other characters who don't approve of their relationship at first.
One possible fanfiction could be about Ash's adventures in Hoenn during the month of May. Maybe he discovers a new Pokémon species that is only active during this time of the year. He could be traveling with his usual companions and facing challenges specific to the Hoenn region.
Maybe Dawn could be Ash's date. They have a great friendship and have journeyed together. Their knowledge of Pokemon contests and battles could be a fun part of their date during the trip. Also, Anabel from the Battle Frontier is a possibility. She's a strong trainer, and Ash has had interactions with her. A date with her during a trip to the Battle Frontier or another region could bring some new and exciting dynamics to the story.
You can start by searching on popular fanfic websites like FanFiction.net or Archive of Our Own. Just type in 'Ash and May date' in the search bar and you'll get a list of relevant fanfics. You can also join Pokémon - related forums and ask other fans if they know of any good ones.
Often, these fanfictions will take the characters out of their normal settings. For example, they might end up in a different time period or a strange new land. This allows for a lot of creativity in the storylines. And the character development of May and Ash is usually a big part of it, showing how they grow and change throughout the story.
Yes, there might be. Fanfiction covers a wide range of scenarios and relationships, so it's possible that someone has written a story where May cheats on Ash. You can try searching on popular fanfiction websites.
A possible fanfiction plot could be that Ash, Serena, and May are invited to a mysterious island full of unknown Pokemon. They have to work together to survive and discover the secrets of the island. Ash's leadership, Serena's ability to communicate with Pokemon, and May's quick decision - making skills would be crucial.
It could be a rival trainer. Rival trainers are often very competitive in the Pokémon world. Maybe this rival is jealous of Ash and May's progress and decides to betray them to slow them down. They might spread false rumors about Ash and May, causing other trainers to be distrustful of them.