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“Appropriate that you wore a scarlet dress,” he added. “We’ll see if we can make your bottom just as red.”
It was useless to try and weasel out of this horror, though I’m not sure I even wanted to when I realized the surfacing arousal. These two men, these two wild-hearted, stern-faced, cold-eyed dominant men with their eyes so fixed on me; I couldn’t very well deny the passion, even if I knew it would hurt like hell before the next half hour was over.
I went to the stool and pulled up my dress, no need to make them order me to do the inevitable. My bottom was as bare as a babe’s facing them, ready to be punished as I knelt on hands and knees. I heard them only briefly behind me, unsure at first who was intending to do the honors. I should have suspected that they’d both have a ‘crack’ at my ass before they were through, but I had my eyes tightly closed too afraid to look.
As soon as the first blow landed I peeked, seeing Reggie standing behind me with a flat wood paddle in his hand. His jacket off, the shirt sleeves rolled up. He was as no nonsense with this punishment as I’d ever seen him. Feeling the second smack land on my bottom, I closed my eyes again and tried my best to endure the assault. I didn’t even see Will, though I imagined he was not far off, thoroughly enjoying the sight of his friend reddening my swaying bottom.
“Yeeeeowch!” was all I dared howl. To protest was useless, I would endure this to the end. Though as resolved as I was to brave the very worst, I had no idea how bad that could be, as one incessant blow after another landed with fierce resolve on my upturned behind. At one point I collapsed against the leather stool that had warmed from my body heat. It was good enough to create a pause, but Reggie ordered me to my knees again, and was only more fierce with the paddle when he resumed.
“Pleeeeeeeese,” I tried a tunefully earnest wail, and he just kept up the treatment. I’m sure by then my ass end was as scarlet as the dress I’d worn.
By some silent agreement, the two men abruptly changed places, and Will picked up where Reg left off. My god! The paddling could go on forever this way, I thought, in the small sliver of time from when Reg stopped and Will began. And yet, it wasn’t long before Will stopped, too. I was surprised and intrigued; though something told me that he was not finished, even if I saw from the corner of my eye that he’d laid the paddle down.
His hand was at my ass, stroking it gently, his fingers probing me in both holes. The entire treatment was beginning to bring out the sexual fires again, and I swayed lewdly against his invading hand, thinking it would only be moments until he’d screw me. But I wasn’t that lucky. Will only stopped so that his friend could retrieve a cane for him, and once Will had the terrible looking thing in his hand, he abruptly stopped pleasuring me.
“I’ve only given you a few of these,” Will acknowledged.
I trembled seeing the dreaded implement. The stripes from cane he’d previously left had been light, but I had the disti
nct impression that it would be different this time. I snuffed then wiped my tears from my face, hoping that he’d have some pity on me.
“Shall I leave a few marks?” he asked, as he stroked my back so very gently.
“Please no,” I sobbed.
“Well, let’s see what a full dozen will do. If nothing else I hope you’ll get the point of the evening. It could have all been avoided.”
He stepped away from me, behind my sore naked ass, and must have eyed me a full minute before he began. My palms were sweating, and I thought I might slip off the stool, if he didn’t proceed quickly.
“Leave stripes, Will, she needs them,” I heard Reggie say, and then I heard the door open and shut. A trademark gesture, Reggie was still ordering my anguish then walking out the door while someone else did the dirty work. As intriguing as that thought was, I had no time to dwell on it.
Will drew back his arm and the first fierce swish landed right in the center of my bottom. I shrieked from the vile jolt. From the outset, I could tell Will was getting over his own fear of the cane; he was positively cruel.
The next six cuts crisscrossed my bottom, no doubt tracing some fine intersecting lines across the center. The next several cuts landed where my lower bottom meets the top of my thighs. Each one was accompanied by a biting pain. By the time Will had reached the tenth cut I was ready to collapse.
“Two more, my darling,” he said, in the kindest, sweetest language, though it was all a ruse to catch me off guard, because the next cut was sheer torture. The last descended with as much ferocity, and this time I slithered from the stool, knowing that I didn’t need to maintain that awful pose.
“Look at me, Alex,” Will demanded.
I sat up and stared up into his eyes.
“You think we’re done?”
“Can’t we be?” I was pleading for mercy.
“Get back on the stool.”
“No, no, please.”
“Alex!” he said sharply.
“Please.”
“On the stool.”
I don’t know how I managed to return to the awful position, but I soon knew that Will had something far different in mind than more punishment. The fingers that had probed my rear channel before were now greased and ready. Appropriate justice I suppose. Where it began, it was ending. And I couldn’t miss the irony, how much this was like my first moment at Reggie’s command. I’d get the message loud and clear or I wouldn’t get it at all. The thrust of his penis across my tight sphincter wasn’t as harsh as that first time, but the implication of submission was unambiguous. But different from that first terrifying assault, I let these sensations take me away. I gave in instead of resisting. All the cries, and all the tears, and all the memories that followed were reminders to me of the woman I was, the submissive I liked to deny.
Will rode me hard. His thrusts were so deep I thought he’d split me in two. And though his substantial cock was bearable, my own pleasure would have to wait, as I struggled just to hang on to that blasted stool. When he was finally done, he held my ass against his groin and let his cock recede inside me.
