I whimpered in panicked anticipation, my eyes opened wide and focused only on him.
He opened this one a bit more gently, but the wave of pain that followed was still just as crippling. I choked back a sob and my legs went weak. He swept an arm underneath me and carried me over to the desk. Carefully, he laid me over it so that I was facing his men and used his foot to spread my legs wide for him.
My sore nipples pressed against the desk, but I was thankful that they were no longer being punished with the cruel clothespins. It would have hurt so much more to lie down with the terrible things still clamped tight onto my poor breasts.
Jon traced one hand up and down my spine and I shivered. The fingers of his other hand grazed against my still very sore clit. I gasped breathily, the pain and pleasure of his light touch catching me by surprise.
“You’re positively soaked, little girl,” he murmured, and I moaned into the desk as he toyed with my pussy with his hand.
The door opened and several more men filed into the room.
“I want you to meet a few of my men. In front of you are my captains, several of my best soldiers, some of New York’s finest, as well as my underboss, Ronaldo. They are all aware that you stole from us and all of them agreed that you need to be adequately punished before we can fully offer you the benefit of our protection.”
I trembled at the meaning in his tone. The men watched in silence, but it settled on me like a heavy weight. I couldn’t forget that they were there, seeing every shameful thing that Jon was doing to me and the mortifying way my body was responding. I shouldn’t be aroused by this whole thing, but I couldn’t figure out a way to turn it off.
“Yes, sir,” I breathed. I kept my eyes on the surface of the desk, not wanting to see the judgmental expressions on the faces of the men that were about to watch the very first fucking of my life.
“Look at them,” Jon instructed firmly.
I trembled as I lifted my chin and gazed back at the dozen men in the room. I’m not sure when, but at some point more of them had come into the room to watch my harrowing ordeal. They were all watching me with vested interest and my cheeks flamed red hot with embarrassment. They’d seen their kingpin fuck my mouth and now they were going to see him take that much more from me.
“Tell my men that you are a very sorry little girl,” he commanded.
My mouth opened and I squeaked nervously as the scalding heat of his cock pressed against my entrance. He didn’t enter me, but the threat that he was going to soon was more than clear.
“I’m a very sorry little girl,” I wavered, biting my lip.
He grasped the plug and twisted it inside me, reawakening the burning pain from its initial insertion. I tensed, expecting him to pull it out, and maybe a little hopeful that he would, but he never did. He just left it inside me.
“You deserve a good hard fucking, the kind of fucking bad girls get, don’t you?”
I whimpered nervously and the head of his cock pushed forward just a tiny bit more. It was difficult to keep still, to not push back against him because a part of me wanted to know what it would be like. My nerves warred with my curiosity, and I squeezed my eyes shut, waiting for the inevitable.
“Yes, sir,” I whispered.
“Are you sorry enough, little girl? Do I need to fuck this sore little asshole instead of this soaking wet little pussy?” he pressed, and I couldn’t help the way my body clenched around him.
“Yes! I’m very sorry. Please fuck my pussy. Please don’t fuck my bottom, sir,” I begged.
His fingers grasped my hips, gently at first and then more roughly. I whimpered as he pulled me back slightly, pushing the head of his cock inside me a bit further. My body was unused to his size, already impossibly full of the large plug.
He thrust in a bit deeper, and I gasped, his thick girth stretching me wide. When he pressed against my virgin barrier, I hissed. That didn’t stop him. Deep down I had known it wouldn’t. His fingers tightened on one side and the other grasped my wrists firmly enough to pin me against the desk. My legs quaked and his hand smoothed over the side of my hip, soothing and gentle compared to everything that had just happened and for some reason it was enough to make me relax. The tenseness bled from my muscles.
“This may hurt at first, but I promise that you will come for me a great deal by the time your punishment is finally over,” he murmured.
The softness of his voice put me at ease and my hips lifted slightly off the desk. With no further warning, Jon jerked his hips forward, thrusting through my hymen and pushing deep inside me. A sharp flash of agony rattled me, and I wailed into the desk. He didn’t move right away, just holding still with the entirety of his length in my no longer virginal entrance.
I had a man inside me.
A criminal.
A fucking mafia kingpin.
And all I wanted to do was roll my hips and take him deeper as he fucked me.
The pain faded as the moments passed and all that was left was the raging heat inside my core. It billowed up like a wildfire, growing more violent and uncontrolled with every passing second. I tried to keep still, but it soon became impossible.
This was supposed to be a punishment fucking, but I wanted it. Badly.