Okay, so yeah, there's a bit of a disconnect between between the times. First Misty, then right to Brock, then all the way to May, and now here we are at an un-specified time after Gary stopped being a dick and started being kind of awesome (that was a stark 180 with little-to no explanation, and frankly it's the only one I've ever seen that I approve of.) So yeah, these are very loose, undetermined times that are the basis for this random collection of only semi-connected chapters. If this is displeasing, then I'm sorry for that, but that sounds more like a you problem. :P
Oh, and a note on the comment concerning the fact that Ash getting knocked up would be hot as hell. 1: Yes, it would, and we all know it. 2: Regardless of that, that isn't how C-boys work. They aren't herms, and are not female in any sense. They are males with female parts, just like futas are just females with male parts and can get pregnant, but can't get someone else pregnant. Confusing I know, even more so when you throw dick-girls into the mix (like futas, but without a pussy and is physically capable of getting someone pregnant and still separate from a herm. Sigh.) 3: If M-preg is your thing, more power to you, but I don't currently have any stories of this kind.
That said, let's get on with the story shall we?
Ash had gotten used to spending more time with Gary. Back before they'd been so busy arguing over pretty much nothing, that they'd never actually talked. When they realized this, they decided to fix that and spend the day catching up. Gary told Ash about his studies, Ash told Gary about his travels and his pokemon. Eventually the subject got around to Ash being a C-boy.
Gary looked shocked by this, "Really? Wow..I kinda feel bad. Even if we were always fighting, we were still around each other a lot and I never knew." "Don't feel upset. I kinda went out of my to hide the fact," Ash admitted, "Back then I was really worried about what you would do if you found out."
Gary looked down, and Ash realized that, without meaning to, he'd insulted Gary, saying he was afraid Gary would immediately use the information to hurt or humiliate Ash. "I..I didn't mean it like that Gary." Ash said quickly, not wanting to restart the ongoing feud between them.
Gary looked up, and surprisingly, he didn't look angry, just upset. "I know..but you're right..I was a real jerk back then, and if I ever had found out back then... I probably would have done something really mean and stupid with it. I did a lot of stuff like that back then, and not just to you either. I wish I could make it up to you.."
Ash frowned, then smiled when an idea came to mind. "Well, I can think of a few ways." Ash said with a grin. Gary had never seen that particular kind of grin on Ash before. It seemed...lustful. The thought of Ash being seductive was actually rather amusing to Gary, but never the less when it actually happened, Gary felt heat begin to rise to his face and he looked away on instinct.
"Like..what?" Gary asked, semi-hoping he was wrong about Ash's meaning.
"Well, you're upset that you would've been mean about me being a Cunt boy right?" Ash said, "Well, how about I show you why you shouldn't be mean to C-boys~?" Gary blushed harder at this, and got up from his seat, "Thanks..but really should be going.."
Ash pouted, "Oh come on, do I really weird you out that much?" "No of course not I just.." Gary sighed, "I'm not exactly a very...open person. At least, not with people. never really was. Guess that's why I never really got along with anyone. Even those cheerleaders I used to have on me were being paid to parade around and cheer for me because I never really made any friends."
Ash frowned, "I'm sorry about that, but..I'm your friend now, and I'd like to show you the perks of making friends with a C-boy, if you'd be willing to give it a chance. If not..I can understand why." He said with a slightly sad smile.
Gary bit his lip, then smiled, "You know what..what the hell. (My personal philosophy ^-^)
About twenty minutes later, Ash and Gary both collapsed onto the bed in the room at the center they'd rented out for the night. Ash had his arms wrapped playfully around Gary's shoulders as the two kissed heatedly. Gary had slipped his fingers into Ash's pants and begun fingering him, listening to the cute little C-boy moan for him.
Ash wondered how Gary had gotten so good with his fingers if he didn't socialize much, then began wondering if how close he was with his pokemon has something to do with that. He didn't have much time to think on it, as soon they were both frantically removing their clothes, eager to see each other's bodies.
Gary looked in awe of Ash's pussy, currently wet from his touch. Ash was equally shocked by Gary's body, much more fit than he'd expected, though not overly so. His fully erect member was much smaller than Brock, but that was to be expected; at at seven inches, Gary was still on the bigger side.
Ash licked his lips, and pulled Gary on top of him. Soon the two locked together into a sixty-nine, Gary eating out Ash with gusto and Ash returning the favor by sucking Gary off eagerly. Ash had gotten good at blowjobs from practicing on Brock, and decided that while a girl's cum still tasted better, he didn't mind it from a guy.
When they came, Ash shifted over, kissing Gary with a mouthful of his own cum to let him taste it. The kiss turned into a sloppy, cum filled make out session as Ash began to ride Gary. Whether he was aware of it or not, Gary swallowed more of his own cum than Ash did, a thought that turned Ash on wildly and helped him cum in only the first few minutes, his pussy squeezing Gary's cock and bringing him to an early climax as well.
They weren't nearly done though. They had the whole night, and Ash was wondering if he could get Gary to try anal...
Oh, and that tidbit about Gary's cheerleaders being actors that he paid for...yeah, that's actually canon. Just thought I'd put that out there.