"Don't care...just...do it...fuck..." he really was beyond all conscious thought at the point, and he was very much relaxed enough to even let this happen.
Kirk took the lube from Remy and climbed off of Tony, then moved to switch positions with her, positioning himself right between Tony's legs. "Gotta get you up a little higher, sport," and he angled Tony's ass up more. Squirting the lube generously on his cock and Tony's ass, Kirk stroked himself a few times, getting himself good and ready as he waited for Remy to get situated. "This might hurt just a little..." and he leaned forward and pressed the head of his cock at his ass, and one could see the resistance there as Kirk struggled to push himself inside of Tony, not wanting to tear the guy up.
Tony yelped as he felt himself being stretched, seeing as how Kirk was pretty wide, and he didn't think he'd make it all the way inside of him, but he felt that little bit of relief once Kirk had pushed past the ring of muscle and he felt every thick inch of him moving further inside. "Oh god...it hurts..." he moaned, and his face screwed up in the pain. Kirk reached to stroke Tony a few times, working him as he slowly slid in and out of Tony, working another inch in with each small thrust.