A/N: sup friends I'm not dead just really slow at updating. Thank you all so much for waiting, you're the best. 3 drafts later and here you have the latest chapter, which I can at least say is longer than the first two combined? Without further ado here is almost 2k of actual porn
To all their friends, Ash and Gary's first time was a mystery. Not because it was never spoken of, but because the stories recollecting the event that the two told differed vastly and often changed from one telling to another. Both stories seemed equally plausible, so no one could tell whose version was the truth. Neither divulged too much information on the topic, since they preferred to keep their personal lives to themselves; however, they occasionally bickered on the subject, giving away certain details they probably wouldn't otherwise.
Gary's retelling of the event generally revolved around the spontaneity of it, since, according to him, they hadn't been dating, or even discussing the prospect of dating. It was sudden and ridiculously hot.
"It happened one night when we ran into each other in Pallet Town. By then I had already given up training and dedicated my time to research, and it had been quite some time since I had seen Ash. He came to see my grandfather, who wasn't in at the time, and ran into me in his lab. We talked for a while and I teased him and one thing lead to another. He was a virgin and completely inexperienced, so I had to handle the situation and lend a hand, physically as well as metaphorically," he added, winking at Ash and smirking, who in turn rolled his eyes at the stupid remark.
Gary interrupted Ash's protest to the remark he had made against him by slamming their lips together and pulling Ash closer. In shock Ash clumsily stumbled backwards and bumped into the table housing Professor Oak's current research project.
"Careful," Gary chided, moving the project carefully to a nearby counter, "We wouldn't want to break anything," he smirked as he turned back to Ash, who was gripping the end of the table, nervous but obviously turned on. Gary walked back to Ash and kissed him again, Ash returning the kiss this time with equal ferocity.
The table creaked slightly as the two deepened their kiss, Ash wrapping his arms around Gary's neck and Gary lifting him slightly, enough to lean him against the table more stably. His hands trailed down to the hem of Ash's shirt, lifting it to run his hands up his smooth skin and tweak a nipple, eliciting a moan from Ash. His face flushed and he tried to cover up his embarrassment with his hands but Gary wasn't going to let him. He wanted to see Ash's face; to hear whatever noises he would make.
Gary lifted Ash's shirt over his head and leaned in to take his other nipple into his mouth, rolling it with his tongue. He could feel the bulge in Ash's pants grow and smirked against his nipple, knowing he was making him feel good. Ash tilted his head back and breathed deeply, attempting to stall the orgasm he could already feel coming.
Sensing this Gary let go of Ash's nipple with a wet pop, to the other boy's dismay, and stood up, removing his own shirt before diving back down and kissing Ash again. He trailed kisses down his neck, leaving hickies here and there against his smooth skin. As he did so he reached down and began undoing Ash's zipper, massaging his bulge through his underwear before pulling them down and pumping his bare length. Ash moaned loudly, whispering Gary's name.
Feeling awkward that he was the only one exposed, Ash reached forward and tugged at Gary's zipper but struggled to pull his pants down from the angle he was at. Gary let go of Ash's length and helped him remove his own pants, which was a relief from the tightness. He fumbled in the drawers under the counters next to them until he found what he was looking for, procuring a bottle that made Ash even more nervous than before, as well as confused. Now wasn't the time to ask questions, though, as he noticed Gary squirting some of the lube onto his fingers.
Ash gulped and Gary leaning in, kissing him softly, "Don't be nervous, I've got you".
Ash nodded, though his body tensed as he felt fingers prodding at his entrance. He tried to relax, taking deep breaths as the fingers entered, causing sudden pain to rush through him. The fingers stopped and Gary kissed him again, allowing him to adjust before attempting to push through any further. Once he received a nod that meant the pain had lessened, he slowly pushed further until his fingers were entirely enveloped. He waited again before removing them and pushing in again, seeing the discomfort slowly fade away from Ash's face and into something that looked more like pleasure. He scissored his fingers and Ash moaned approvingly. Once he felt Ash was ready he added a third finger and opened him up further.
Gary removed his fingers and grabbed the bottle of lube again, this time coating his own length and positioning himself at Ash's opening. He steadied himself by holding onto Ash's hips and slowly pushed in, watching as Ash's face scrunched up in discomfort he stilled and waited for the discomfort to subside before pushing in even further. Ash was breathing deeply, his head fuzzy from what was happening, when he felt Gary pull out and push in again, grazing a spot that sent shivers down his spine and caused him to moan slightly.
"Do that again," he panted, out of breath already.
Gary grinned and pulled out again, entering with even more force and aiming for the spot that would allow him to hear Ash's voice loud and clear. He was not disappointed when Ash delivered, nearly yelling.
The pace Gary set started out slow, allowing himself to fully enjoy being inside of his rival- feeling every inch of him at once. His thrusts became increasingly faster as it was harder for him to keep such a slow pace, in need of release himself. As the pace increased Ash had an even more difficult time keeping his voice down. He grabbed onto the end of the table, curling his fingers around the edge, and attempted to quiet himself by biting into his bottom lip. It became so difficult for him to stifle his moans that he was nearly drawing blood, so he gave in and allowed a small moan escape from his lips.
Hearing this Gary smirked and thrust harder, causing Ash to moan even louder, despite his best efforts to keep it down. Ash was nearly at his breaking point and Gary could easily tell by the way his breathing had become so labored. He was in a similar position, his orgasm only a few thrusts away. As Gary slammed in once more Ash came, sinking blissfully into the after-glow. He barely felt it when Gary soon followed suit, spilling inside of him and slumping forward, panting.
"That is nowhere near how it went!" Ash shouted, dismissing Gary's story. Ash told everyone that first time had been a challenge. "He was mocking me, telling me that I wasn't mature enough to handle such an 'adult experience' and so I proved him wrong!"
They fell to the floor and Gary proceeded to straddle his hips, pinning his hands down above his head by his wrists and licking his bottom lip as he gazed down at him, "Don't worry, Ashy-boy, I know this is new territory for you, but you've got a master here to guide you."
Ash rolled his eyes, staring up at Gary defiantly, "I can handle more than you think," he spat.
"Oh, really?" Gary leaned in and kissed him deeply, releasing his arms to allow Ash to wrap them around his neck and deepen the kiss.
"That was his first mistake!" Ash laughed, faking a pout, "I may look stupid, but I'm far from it!"
Gary rolled his eyes.
Ash used the temporary moment of weakness on Gary's part to grab his shoulders and flip them over, allowing himself to straddle Gary and take control. He kissed him again and started undressing him, taking time to run his hands along Gary's lean yet muscled chest. He left a trail of kisses down his chest and stomach, stopping at his pants to muster up whatever courage he could find within himself. Gary waited patiently, a slight smirk on his face.
Ash unzipped his pants and swallowed deeply, shocked at how far this had gone. He never expected to be staring down at Gary Oak's clothed erection, which was obviously already quite large. He ran his hand through his hair nervously before taking a deep breath and pulling his underwear down, revealing Gary's stiff cock to the open air.
It was at that point he sat frozen, realizing he honestly had no clue what to do next. As he wracked his brain for what would be the best possible thing to make his rival squirm, as well as proving he wasn't as innocent as he appeared, Gary sat up and pulled him closer, locking their lips again. He unbuttoned Ash's jeans and grabbed his cock, pumping it a few times, causing Ash to gasp and moan in shock. He leaned forward, pressing his face into Gary's shoulder and moaning softly against his skin.
Gary released Ash's cock when he was obviously near finishing, pulling him into another kiss and biting Ash's bottom lip softly, causing him to moan into the kiss. Gary reached over to the pocket of his recently discarded pants and pulled out a packet of lube and a condom.
"I always come prepared," he grinned, tearing the packet of lube open and squeezing some onto his finger. He pushed Ash against the bed lightly, nudging his legs apart. "Just remember to relax, okay?" Gary said reassuringly as he eased his slick finger into the other's hole.
Ash gritted his teeth at the intrusion but tried to keep his breathing steady, hoping the discomfort would cease. He closed his eyes as he was worked open, a second finger following the first. Before long he was beginning to enjoy the feeling of the fingers, soft moans escaping his throat.
The fingers pulled out and he groaned, missing the feeling of the digits inside of him.
Gary shushed him as he steadied himself at Ash's entrance, pushing in slowly, until he was nearly enveloped in heat. It took all of his effort to not pull out and thrust in again quickly, but he knew Ash needed time to adjust. He pulled out slowly, starting a slow rhythm as he listened to Ash's moans of approval beneath him.
The rhythm picked up and despite a small amount of discomfort, Ash was feeling amazing. He lifted his legs and wrapped them around Gary's back, leaning his head back further and moaning loudly.
Gary couldn't help but grin at the sound, thinking of the innocent boy he used to know, knowing he was the one who could cause Ash to make such noises. He picked up the pace, knowing they were both near their end.
Ash's breathing became ragged, "I-I think I'm gonna-"
"Go ahead," Gary whispered into his ear, "let it out."
With Gary's reassurance, Ash came and all he could see was white as the impact of his orgasm hit him. Gary followed quickly after, filling Ash and feeling the bliss wash over him.
Once the post-orgasm high receded, Gary pulled out and rolled over, breathing heavily. Ash turned and smiled at him, "Next time, I'm gonna make you cum first."