Alan wasn't sure when the thresh hold hit but he could feel it when he was done tormenting Nate. That didn't mean he was getting off easy. "I'm going to remove the dildo... but I want to keep you full inside so go ahead and clench your muscles to keep the cum inside of you." he said firmly his eyes drinking in the sight of his omega that was beyond a wreck. He shifted the table that Nate was on slightly down, finding just the right angle to sink into him... condom on of course. He could keep Nate's clenching trying to keep the pressure of the thicker liquid inside along with his arousal. It was such a turn on to feel that struggle and to feel it dripping out as he fucked into him with little holding his back.<br/><br/>There was no doubt that Alan had taken to tormenting Nate on a whole new level in between stretching his hole with the beads and now this but he liked how dirty it made Nate seem even if his ass was no longer virgin tight for the moment he loved how whorish it felt to have his omega take his cock so easily as if he had been filled up to the brim was stranger, or Alan's, cum. The fantasy was a little more then he could even process as the lawyer lost his control and came inside of Nate as if adding to the mix even if his cum was separated by a thin latex barrier. "Now... since you have been so good I'm going to release your cock... and you can cum any time you want." with those words he unsnapped the strap and as the same time pulled out from Nate his fingers sinking inside to take it's place but spreading Nate so he had no choice but to release the fluid that had build up inside as Alan's fingers pounding on his prostate with no reservation.