Iya The Mob Boss Has A Plan

"Hi, Iya," I said as Alex led me into her office. As usual, she sat at her desk, and my eyes immediately went to her huge tits. They're so amazing, so big and full, and she always wears dresses that show off her valley of cleavage. The last time I was here, I actually got to see them. They were fucking spectacular.

"Good evening, Matt. Do you have my money?"

"Yes, I brought another thousand."

"Really, I thought you were tapped out."

"I am. I'm running up my charge cards."

"That's not going to get you to the twenty thousand you still owe me."

"I know, I'm working on it."

I dropped the money on her desk, and she looked up just long enough to grab the cash and stash it in her desk.

"Well then, go ahead and strip. You still need to be punished."

I expected it, but I keep hoping that the money I bring in will make her show some mercy. So far, no luck. I do still owe her twenty thousand, and I have no idea how I will get it. Especially since she won't let me place bets with her any longer. That's the one thing I'm good at. Well, not that good, I did go twenty five thousand into the hole. These thoughts all ran through my head as I took my clothes off. My poor balls were going to get it again.

Iya stood up and grabbed a bottle from her desk. She walked around to my side and sat on the edge of the desk facing me. She handed me the bottle.

"What's this?"

"It's lube. Since you're going to cum on me anyhow, I decided to just have you jerk off."

"What, really?"

"Sure, why not?"

"No kicks or knees to the balls today?"

"Oh, I didn't say that. I'm just going to do it after you blow your load. Smart, right?

"Uh, I guess so."

I took the lube from her and shot some into my hand, then I ran my hand up and down my cock. I began stroking as she watched. It felt weird, my cock wasn't very hard. I felt silly having her watch me, and my cock was not responding well. I was going soft. Of course, I was nervous about getting kicked in the balls as I came, but I didn't think that was the problem. I needed to see more of her breasts.

"Iya, I need a little help."

"I'm not touching your cock, this is just you today."

"No, not that. I need to see your tits so I can get off."

"Are you kidding me?"

"Look, you can see I'm going soft. I need some visual stimulation."

"You'll cum from looking at my tits?"

"That's what happened yesterday."

"Oh, for fuck's sake, okay." She pulled down the straps to her dress, and her big, beautiful breasts popped out. Instantly, I felt it in my cock, it was already getting harder. Much harder. Her tits are just magnificent, so big and full. My cock was rock hard in half a minute, so I picked up the pace of my stroking. It wasn't going to take much longer. I was transfixed by her big breasts. In my mind's eye, I pictured tit fucking her. Just a few more strokes.

"I'm cumming," I moaned as my cock shot a rope of cum onto the floor. She leaned forward from her perch on the desk, then she took a step towards me. Her breasts swung as she walked in my direction, they were all I thought about. But then, as I watched her foot swing back, I remembered.

The dull thud of her foot smacking my balls took me by surprise. It didn't hurt that much at first, but then the pain came. It came hard. I doubled over and grabbed my aching balls in my hand. I let go of my still throbbing cock, which continued to drip blobs of cum onto the floor.

"Move your hands and stand up!" she commanded.

I couldn't do it. I was struggling to breathe, and my knees were barely stable.

"RIGHT NOW, OR I WILL DESTROY YOUR BALLS!"

I pulled my hands away, then I slowly straightened up. I didn't want to, but I spread my legs. Her breasts were still out, at least I could look at them. It helped.

"That's better!" she said.

"OOOOOOOFFF!" I grunted as she kicked my nuts even harder. I dropped straight to the floor in front of her. I lay on my side, my cock oozing cum and my balls aching, and cupped in my hand. My balls were screaming in pain, I was so sensitive from cumming. The ache in my balls was mind-bending.

"Shit, Iya, I brought you the money you asked for."

"Just think how bad this would have been if you didn't."

I didn't want to even consider it.