Adrian seemed to hesitate. Perhaps this was unexpected, perhaps he was just thinking things through. He could even simply be building tension before engaging his pokemon in this sexual act. After a few moments though, Umbre could feel his hand on her bottom, softly squeezing her tight ass before sliding over to pet her tail. Pulling his hand up the length of the bushy expanse.<br/><br/>The sound of his zipper opening would notify the both of them of his intentions, he was not going to let this chance go to waste, even if he might have had less intrusive plans at first. His voice was soft, almost reassuring when he spoke during his preparations.<br/><br/>"I'm proud of you Umbre, there are few pokemon 'willing' to go this far. This shows me how much promise you hold and I'm certainly not disappointed." The dark type pokemon could feel his shaft press against the outer edges of her nether lips now, stroking up and down its length. Compared to the relatively smaller pokemon body, it was huge. His masculinity was certainly not something to be ashamed of.<br/><br/>As the tip of his cock rubbed against Umbre's clitoris, she might realise what he was doing. Using her own sexual fluids exactly what they were designed for. The moistness would make his entry much, much smoother, and it served well  to get them both ready in all other aspects. His hands were stroking up and down her legs, as far as he could reach without losing contact. Just something to help her relax, as far as that was possible right now. He would, 'explain', to Valeria soon. Though his need became to great to postpone his entry and longer.<br/><br/>Sliding his cock against Umbre's lips one more time to find the correct height, Adrian had made himself ready, and hopefully his pokemon as well. Increasing the pressure against her lips by pushing against them with his cockhead, before easing up a little. That was the que, he could not longer wait now. In one firm thrust, he jammed it inside.<br/><br/>His thick, long shaft made it only halfway on the first go, though to Umbre it would likely feel as if it couldn't possibly go in any further. The small size difference between then and her athletic frame made this extremely pleasurable for Adrian, and a small part of his mind remembered that he should make sure she enjoyed it as well, if just a little.<br/><br/>Reaching under her shoulders to find her breasts and taking a firm grip on them gave Adrian a pleasing set of handles to work with. Though his fingers would quickly find her nipples and start their, perhaps surprisingly, pleasant playing. Fondling her breasts and gently squeezing and rubbing her nipples under various grunts of passion. Umbre's trainer was greatly enjoying himself, and had almost forgotten about Valeria below the copulating couple.<br/><br/>Interrupted by his grunts, he would speak to her almost as to himself. Though it would serve well to add to her mindset. She would either simply deny everything and turn on him regardless, or slowly settle into the same situation as Umbre. Both, needed eventual 'motivation'.<br/><br/>"You're, wonderful Umbre! Letting your trainer use you like this feels like the ultimate expression of being a caught pokemon." He hadn't forgotten about Valeria entirely, her part would come soon. "If you finish this properly my sweet Umbre, you'll have more than earned the reward I had in mind, for the both of you." That would give some food for thought, Valeria had been trying to stop Umbre, quite possibly turning said reward into a punishment if she had succeeded. "I'm willing to let your sister's disobedient actions of today slide, just because you're proving to me here and now that the both of you have the potential to be part of my permanent pokemon."<br/><br/>And with that, he squeezed the umbreon's nipples just a little too hard to be pleasurable. Just a small reaffirming of who's in charge before the gentle and pleasurable fondling resumed. Adrian was getting closer to a climax, though without Umbre's help it would still take a while for him to get there.