Give him a moment to rest

You see that he's truly at his limit now. If you kick him again, he would just pass out. You'd have to improve this immensely in the next two weeks before you left and turned him over to Val, who you knew was looking foward to to it. Right now she had two lower level assistants compared to you switching out since neither could handle a full day of her ****. You had to have Brad ready to satisfy her. Hearing a scream, you and all of your coworkers look up to see both the male and the female assistant being punished by Val. The woman was in a hanging frontal wedgie on the rail and the man was having his balls crushed under his own ass as he cradled the same railing the girl hung from. They were both naked with only the woman wearing anything, which was her panties that was so far in her that they just didn't count at this moment in time. The man's balls were swollen, you could see that even with them being crushed, and both of their asses were dark red from a paddling. Looking closer at the woman shows that they had both taken hits from the paddle to their groins as well. You glance down at Brad who looked nervous. He also had a major hard on, so you slam your foot down on his left nut, crushing it for a moment as he screams. Looking back up at the two other office toys, you notice Val eyeing her newest toy. You were going to have to really bust his nuts if you wanted to give him a chance against her without passing out by the middle of the day. Grabing him by the front waistband of his underwear, you begin to drag him up the stairs, his suit pants falling off as his ass sliding against the stairs pulls them down, exposing his crushed nuts mushrooming around his underwear. With Val's help, you get him hanging next to the woman.

"This is more endurance training. You can come down when your underwear rips," you explain to the agonized look on his face as his nuts crush under his own weight, his jaw dropped in a silent scream as his brain struggles to process the pain radiating from his swelling sack. Then, you just leave him there to get some actual work done. His scream would alert you to when he fell, him and the woman were both positioned to fall crotch first onto another railing when they fell. Still, you weren't actively crushing his balls, so this counted as his break from it. He would get used to it after maybe thirty minutes when he starts to go numb, anyway. That way it would hurt more when he fell, as well as snapping him back to attention. His balls would then be extra sensitive as you kicked feeling back into them.