Ivan Bearhugs a Journalist

"What are you thinking about, sissy boy?" Ivan asks.

"I'm... I'm gonna cum, Master Koloff..." I whimper, "I'm gonna cum in my jockstrap."

"Oh? Well, good," He pulls his hand away from my throat and releases my crotch. "But I can't have you cumming in your jockstrap. So I'll have to punish you."

It is clear to me now that everything I do deserves punishment from Ivan Koloff. It is not a fear or crime, but just a fact.

He grabs me under the armpits and lifts me up into the air. My dick aches and burns and leaks. Ivan sets me back down in his lap, my bare cheeks at his crotch, my jockstrap-bulge firm against his stomach. He brings his hands slowly behind my back, and locks his eyes with mine. I know what's about to happen, and this time, and only this time, am I ready.

"We will learn so much together," he says, "about how good my bearhug is."

He starts pulsing his grip around my back, bringing us chest to chest repeatedly. The force of his grip, even when seated, is almost too much for me, and I'm certain he knows it. His hold is unbreakable. I'm helpless, and I'm trapped.

Ivan's nods knowingly. I can't move my hips--I'm pinned to his waist. "You're weak. So weak for me, aren't you, sissy boy?"

He keeps crushing me into his torso. I can't breathe. I can't fight. All I can do is scream in agony as my ever-dampening jockstrap gets ground against Ivan's abs.

"Yes, Master!" I moan loudly, letting my hips buck with what little room the pulse of his squeezes give.

Ivan laughs. "You've given in to your weakness. You've lost control of yourself. That's why you're crying now, isn't it?"

I can't answer. I can't speak. Tears just gush out of me.

"Yes, you're crying. It's okay to cry, sissy boy. Cry for me. Just like it's okay to cum in your jockstrap. Master gives you permission."

My tear-filled eyes roll back into my head. One more jerk into his body, one more squeeze of his forearms against my ribs, and it's over. I start shooting and staining my jockstrap. My head collapses against his heaving, hairy chest. Ivan laughs at me. I'd feel more shame if I wasn't in the throes of one of the most insane orgasms I've ever had.

Ivan picks me up, gently cradling me against his body. His hands slip under the band of my jockstrap, and he orders me to take them off and hand them to him. I comply, my head swiveling, unsure of what he has in mind.

Ivan smacks my ass, sending a jolt through my body. It wakes me, briefly, from my stupor.

He holds up my jockstrap, and shoves the darkened stain my orgasm made. "Your jockstrap is ruined. Do you understand? These don't just grow on trees."

"I'm... I'm sorry..."

He caresses my cheek with a big hand. "You'll have to train with me until we can keep you from making a mess." He balls up the fabric and shoves it into my willing, obedient mouth. My eyes glaze over as the tasty of my salty submission and rough cotton forces my jaws wide.

"No spitting this out," he warns. "Go walk to your car like this and leave."

I nod silently. I can't speak through the gag, but he knows I agree without needing words. I stumble in a daze, trembling, my dripping, spent cock staining the floor with dots of shame.

"Next week, same time," Ivan commands. "Make sure you bring a fresh strap, sissy boy."

Ivan steps back and walks away. I push through the exit doors, and feel the cool air caress my naked, spanked, crushed, abused flesh. The parking lot is long, longer than it was before, but the cover of night gives me at least some slight sanity. I am not sure how many pairs of jockstraps I have at home, but I'm already thinking about their future.