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Eventually I realized that his hand was petting my lower back, sliding back and forth in a way that was both soothing and hypnotizing at the same time. I shifted slightly, just trying to cope with the incredible feeling of fullness inside me. The plug felt so big and so heavy that I knew I would never be able to forget it was in my ass. My asshole was so shamefully sore, and I bit my lip.
My clit pulsed. Even as I laid there over the desk with my ass sore inside and out, my desire continued to swell.
What was wrong with me?
My tears started to dry and when they finally stopped, he slowly guided me to a standing position, jostling the plug as he did so. I bit my lip, quieting a yelp as my body tightened around it, which only caused another flare of pain to pitch through me.
I stood there naked with my hands cuffed behind my back while one of his men dragged over a straight-back chair. Jon reached behind me and unlocked the cuffs before guiding me to a seat. The surface of the chair was hard against my sore backside, and I squirmed a little, which only seemed to make it worse. Gently, he guided my hands behind it and re-cuffed them.
I sniffled and he reached for my face, using his thumb to wipe away a single stray tear.
“You’re so pretty when you cry for me,” he said, his voice so soft that I wasn’t sure if anyone else would hear besides the two of us. His eyes were warm, caring even as he caressed me. Then, he reached into his pocket and took out a steel clothespin. Without hesitation, he reached for my left breast and before I knew what was happening, he clamped it right over my nipple.
Piercing agony blossomed over my breast, and I jerked forward, bowing my body as if it could make it better.
It didn’t.
I trembled, squeezing my eyes shut and forcing myself to keep breathing, albeit shakily. When the stinging finally ebbed, Jon took my right breast into one hand.
“Wait!” I wailed.
Another clothespin closed over my right nipple and the pain was just as bad as before, except worse because I knew exactly what was coming. I quivered through it, bracing myself against the chair and curling my body away as much as I could. By the time it finally faded to a more reasonable ache, Jon grasped my thighs and spread them wide. With his fingers, he split my folds. By the time I saw the last clothespin in his other hand, it was already too late.
It closed down directly over my clit.
My eyes opened wide. I choked as a deep agony surged through me, spiraling into my core with wild abandon. He held my thighs open even though I struggled to remain still. Every muscle in my body clenched as that initial volley of pain drowned me, but it was the overwhelming blossom of desire that followed that truly caught me off guard.
He stood up and looked down at me, causing tremors of need to course through me at the sordid heat in his gaze.
I squirmed a little, consumed by the ache in and across my ass, my nipples, and my pussy. My body throbbed with unwanted heat, which only continued to rise under his close inspection.
My chest rose and fell as I breathed, lifting the clothespins up and down in the process. I kept my eyes downcast, knowing all the men were probably still watching the whole terrible punishing display.
Jon leaned against the wall and crossed his arms over his chest. Someone opened the door and carried in a familiar suitcase. They must have gathered my things from the hotel. Jon cocked his head toward the large desk and the man carried it over to it, opening my bag and bowing respectfully in Jon’s direction. Jon walked over to it and started pawing through my bag.
He unfolded each piece of clothing and tossed it into the office chair without a second glance. When he uncovered my small vibrating bullet, he held it up suggestively and one of the men hooted with amusement. I blushed bright red, but I didn’t say anything. Jon placed it carefully on the desk before returning to the rest of the contents of my luggage. When it was empty, he closed the zipper and put it aside.
Another dirty cop came into the room with my backpack slung over his shoulder. I watched as he passed it to Jon, who took it with interest. He opened the zipper and started digging around inside it.
When he pulled out a jewelry box, I gulped nervously. He flicked it open, revealing the beautiful tanzanite necklace I’d stolen from his vault.
His footsteps were deafeningly loud as he strode over to me. His expression had darkened, making my legs tremble.
“Get me that side table,” he barked and one of his men jumped to heed his command. He dragged over a small table and Jon placed the necklace down on it right in front of me.
“I have to have a chat with my men. While I’m gone, you will sit here and think about what you want to say to me when I return. Do you understand me?” he warned.
I nodded quickly.
“Say it,” he growled.
“Yes, sir,” I whispered nervously.
He hadn’t said it, but his tone had indicated that things could only get worse. With a heavy sigh, he gestured for his men to leave the room. I watched them all file out, thankful that I’d at least have a moment to myself to gather my thoughts. I needed that respite more than anything.
As the minutes passed though, I started to regret that initial stab of relief. My bottom ached, still sore and burning from the belt. My asshole was extraordinarily full of the plug. The longer it was inside of me, the more it hurt.
I leaned forward. My breasts felt heavy with desire and my nipples pulsed with increasing soreness, but it was the clothespin on my clit that hurt the most.
