Jacob, ofcourse

I reached under the desk, grabbed Jacob by the collar, and dragged him out into the open. He came up on his knees, the thick black strapon still buried deep in his ass, Yuki close behind him with the harness straps digging into her hips. His face was flushed, eyes glassy, cock hanging hard and ignored between his thighs.I picked up the dark, veined dildo Emily had bought - still shiny with her spit - and held it in front of his face."Take that plastic cock out of your ass and replace it with this one."

Jacob’s eyes flicked to the bottle of lube sitting on the desk. I saw the small spark of hope. I chuckled and shook my head."No. I was going to make you take it dry… but Emily already lubed it very well with her mouth. That’s all the help you’re getting."

Yuki bit her lip, then reached down and slowly pulled the thick strapon free from her husband’s ass. It came out with a wet, filthy sound, leaving his hole open and twitching. She spread his cheeks wide with both hands, presenting the stretched, puffy ring to me. I didn’t give him time to clench.I lined up the spit-slick head of the oversized dildo and shoved it in with one hard, merciless push.The entire thick length disappeared into his ass in a single stroke.

Jacob’s scream was loud and raw - but the gag I’d shoved between his teeth earlier turned it into a muffled, desperate howl. His eyes flew wide, instantly flooding with tears that spilled down his cheeks. His whole body jerked, thighs trembling, the heavy dildo seated impossibly deep inside him.I laughed, low and dark, and gave the base a little tap. "Look at that. Went in nice and easy. Emily’s spit really did the trick… or maybe your hole’s just getting used to being stretched open for me." I twisted the dildo slightly, watching another tear roll down his face, then looked at Yuki."Hold it there. Don’t let him push it out."

I looked down at Jacob, still on his knees with the thick dildo buried to the base in his ass, tears streaking his face around the gag.

"You should really thank Emily for this..." I said calmly. “Her spit is the only reason that thing went in so easily.”

Jacob’s eyes darted around the office in confusion, clearly not understanding. He made a muffled sound behind the gag.

I didn’t give him time to think. I grabbed a fistful of his hair and smashed his head down onto the desk with a heavy thud. He grunted in pain, cheek pressed flat against the wood, the dildo shifting deep inside him from the sudden movement. With my other hand I reached over and slapped the intercom button.

"Emily..." I said, voice smooth and clear over the office speakers. "Your former boss wants to talk to you. Come to the intercom."

A few seconds later her voice came through, slightly breathless.

"Yes, boss?"

I looked down at Jacob, still pinned to the desk, and gave the base of the dildo a sharp kick with the toe of my shoe. The thick toy jolted deeper into his ass. He jerked hard, eyes flying wide.

"Talk" I ordered quietly.

Jacob’s voice came out shaky and strained, the gag removed just enough for him to speak while his cheek stayed pressed to the desk.

“E-Emily… thank you. Thank you for everything you’ve done for me till today. I’m very grateful. Truly. I would love to repay your services in any way you want. Anything at all…”

I gave the dildo another firm tap with my foot, forcing another choked sound out of him, and smiled.

"You heard him, Emily. Your former boss is feeling very thankful. Get back to work. He’ll be here if you think of a way for him to repay you later."

I released the intercom button and looked down at Jacob, still trembling with the oversized toy stretching his ass wide open.

"Good boy."