Chapter 23
CHAPTER 23
D ylan
I raised my arm high and brought the strap down hard across both cheeks of Andrea’s adorable, round bottom.
The sound of leather meeting flesh echoed through the room. Andrea let out a strangled cry, her body jerking against the restraints.
“One,” I said firmly, watching as a bright pink stripe bloomed across her pale skin.
I paused for a moment, letting the sting sink in. Andrea’s breath came in short, sharp gasps. I could see the muscles in her thighs and buttocks tensing as she braced herself for the next blow. I raised my arm and brought the strap down again, the lash ringing out like a gunshot as it made contact with her sweet globes.
“Two,” I counted, as another stripe appeared just below the first.
Andrea whimpered, her fingers clenching and unclenching where they were bound at the sides of the ottoman. I hardened myself against the urge to comfort her. This was a necessary lesson, one she needed to learn thoroughly.
I delivered three more blows, grimly counting each one. Andrea cried out louder at each lash. Her bottom began to take on a uniform rosy glow.
“It hurts, sir!” Andrea sobbed. “Please… I’m so sorry! Dylan… sir, please…”
“I know you’re sorry, sweetheart,” I said, making my voice gentle but firm. “But we’re only just beginning. You have a long way to go before you’ve learned your lesson.”
I raised the strap again, bringing it down with precision across the fullest part of her bottom.
“Six,” I counted.
Andrea’s cries grew louder and louder. By the tenth lash, she was openly weeping, her body shuddering with each impact. Her bottom had turned a deep, angry red.
The eleventh stroke of the strap made her frantic, in a way that confirmed for me just how badly she had needed this stern punishment. I had forgiven her for the scene in the Trattoria the previous night, of course; the public spanking in my truck had taken care of it in my mind. But when I had heard of her touching her sweet virgin pussy in bed this morning, I had suspected exactly what her sudden writhing against the restraints and her near-hysterical sobbing told me now.
Andrea Jacobsen needed firm boundaries. She surely wasn’t aware of it, but masturbating in bed, when she knew how likely Greta was to walk in and discover her, represented a request to learn much more about her submissive needs. A plea, from my perspective, for me to take her in hand the way Devin—very wisely, I thought—had decided I should.
As I delivered and counted out two more lashes with grim determination, Andrea shrieked and sobbed and tried to twist out of the restraints that held her in place on the ottoman.
“Settle down,” I instructed sternly. “We’re more than halfway done, but I’m not going to continue until you show me you can take your whipping like a good girl.”
Andrea
It took long seconds before I understood what Dylan was asking of me. I seemed to feel his words in my body as much as I had heard them in my ears and grasped them in my mind. The wildness that had taken hold of me, the sudden snap of my will, when I had understood that I couldn’t get out of this whipping, that I would receive all twenty-four lashes no matter how I screamed or struggled… it faded gradually, and then much more quickly, until I had come to my senses and I could perceive the quiet that had taken hold of the living room.
I heard wet sounds behind me, and though it seemed absurd, I felt my cheeks grow warm on behalf of Lila and Lydia, because I knew their suitors must be using their mouths to enjoy the sight of my punishment. I pictured it despite myself: the two big men on the couch, the two girls on the floor, their heads held still for their suitors’ thrusting cocks or perhaps allowed enough freedom to show their reverence for the jutting shafts with lips and tongue.
A wave of agony from my bottom made me buck my hips and clench my backside in a vain search for some relief. I let out a sob, much softer than the screaming ones to which I had given voice as Dylan had delivered the twelfth and thirteenth lashes. The pain in my rear end, together with the sounds from behind me, brought a new, mortifying but irresistible longing to my mind and my body.
I wanted desperately to have Dylan’s rigid penis inside me. I remembered the stern but caring way he liked to use my mouth. I wondered how he would fuck me, because just as I knew I would have to accept my whipping, I knew I would have to accept my defloration.
And… and…
I whimpered into the leather of the ottoman.
And I want it. All of it.
“Are you ready, sweetheart?” Dylan asked, from behind me and above me. “Can you take your whipping obediently?”
In his voice I heard knowledge that made my heart ache with longing for his arms, even as I felt to my distress another ache beginning to rise again between my thighs—for something harder and less yielding than Dylan’s embrace.
“Yes, sir,” I whispered.
“Good girl,” my accepted suitor said, and brought the strap down again.
The next few minutes seemed to last years. Dylan whipped my bottom and upper thighs so hard I thought I would never sit down again. I knew I would have bruises to remind me in the mirror every morning for a week at least how strict my accepted suitor was with me. I wept and whimpered as the white-hot agony built and built on my rear end.
And yet I also tried, as much as the restraints would allow, to push out my punished cheeks for more. I wanted to show Dylan and Greta and Devin and even the other associates—and Lila and Lydia, if their suitors let them see—that Dylan could tame me and turn me into his good girl. It hurt so much, but I knew I could please the man I loved by showing how thoroughly I accepted his justice.
Dylan delivered the final lash with a resounding crack. I let out a choked sob, my body trembling as the last wave of pain washed over me. My bottom felt like it was on fire, each throb a reminder of my punishment and Dylan’s authority over me.
“Twenty-four,” Dylan announced, his voice steady but tinged with something I couldn’t quite place. Compassion? Desire? Both?
I heard the soft thud of the strap being set down on the side table. My breath came in ragged gasps as I tried to process that it was finally over. Tears streamed down my face, dripping onto the leather of the ottoman beneath me.
Then I felt Dylan’s hand on my lower back, his touch unexpectedly gentle. “You took that very well, sweetheart,” he murmured, just loud enough for me to hear. “I’m proud of you.”
His words sent a surge of warmth through me, momentarily overshadowing the burning ache in my bottom. I whimpered softly, overcome by the conflicting sensations of pain and pleasure.
Dylan’s hand began to move lower, caressing the curve of my hip before sliding between my legs. I gasped as his fingers brushed against my bare pussy, my body instinctively trying to press back against his touch despite the restraints.
To my shock and mortification, I realized I had become soaking wet. Dylan’s fingers glided easily through my folds, spreading the evidence of my arousal. I sobbed with need, my hips rocking as much as the restraints would allow.
“My, my,” Devin’s voice cut through the haze of sensation. “Would you look at that? Our little Andrea is absolutely dripping.”
“Mmm,” Greta hummed in agreement. “I do believe the naughty girl enjoyed her punishment. Just look at how wet she is for Dylan’s cock.”
I buried my face against the ottoman, burning with shame at their crude observations. But I couldn’t deny the truth of their words. My body ached for more of Dylan’s touch, for a fullness only he could provide.
From behind me, I heard again the obscene sounds of enthusiastic oral sex. Lila and Lydia were clearly pleasuring their suitors in real earnest now, their muffled moans mixing with grunts of satisfaction from Hank and Bill.
“That’s it, baby,” I heard Hank growl. “Suck that cock while we watch your friend get fucked.”
“Yeah,” Bill chimed in, his voice rough with arousal. “Show Dylan how eager you are to please him, Andrea. Just like our good girls here.”
Rhythmic sounds from the other side, accompanied with soft almost-snorting breaths that made me think of wild stallions, told me that Ethan and Travis were enjoying the spectacle in their own way.
“You’re a lucky SOB, Dylan,” Ethan said in a voice thick with lust.
“You owe us a few beers at least,” Travis contributed, a chuckle rumbling in his chest.
My mortification at being worth only a few beers faded quickly, only adding to the building of my shameful arousal. Dylan’s fingers continued their maddening exploration, circling my clit before dipping lower to tease at the entrance to my aching sheath. I whimpered and squirmed, desperate for more.
“Please,” I sobbed, beyond caring how pathetic I sounded. “Please, sir… I need…”
“What do you need, sweetheart?” Dylan murmured.
The room fell silent as I heard the unmistakable sound of a zipper being lowered. My heart raced, knowing what was coming next. I felt Dylan move behind me, positioning himself between my spread thighs.
Then I felt it—the hot, blunt head of his cock pressing against the virgin opening, the place where I needed him, where I needed fucking so very badly. I gasped at the sensation, my body trembling with a mixture of fear and desperate need.
“Are you ready, sweetheart?” Dylan breathed, his voice low and thick.
“Y-yes, sir,” I whimpered, straining against the restraints that held me in place. Despite my embarrassment at being so exposed in front of everyone, I found myself trying to push back against him, silently begging him to claim me.
Dylan gripped my hips firmly, holding me still. “Easy, Andrea,” he soothed. “Let me take care of you.”
With agonizing slowness, he began to push forward. I felt myself stretching around him, my body struggling to accommodate his impressive girth. The pressure built and built until I thought I would burst.
Then, with a sudden thrust, Dylan broke through my maidenhead. I cried out at the sharp pain, tears springing to my eyes. Dylan stilled, allowing me a moment to adjust.
“That’s it, sweetheart,” he murmured. “You’re doing so well. Just relax for me.”
Gradually, the pain began to fade, replaced by an overwhelming feeling of fullness. Dylan started to move, withdrawing slightly before pushing back in. Each thrust sent sparks of pleasure shooting through my body.
“Oh, god,” I sobbed, overcome by the intense sensations. “Dylan… sir… please…”
Dylan’s pace increased, his hips slapping against my whipped bottom with each thrust. The pain of my terrible lesson mingled with the pleasure of being filled. The mix of sensations left me dizzy and gasping.
“That’s it, sweetheart,” Dylan growled. “Take my cock like a good girl. Show everyone how well you submit to me.”
I moaned shamelessly, no longer caring about the audience watching my defloration. All that mattered was the exquisite feeling of Dylan’s cock stretching and filling me.
For several blissful minutes, Dylan fucked me with steady, powerful strokes. I could feel my inner walls clenching around him, my body greedily trying to pull him deeper.
Just as I felt myself approaching the edge of orgasm, Dylan suddenly stilled. I whimpered in protest, trying to push back against him.
“Not yet, sweetheart,” Dylan said, his voice strained with the effort of holding back. “We’re not done with your lesson.”
He withdrew slowly, leaving me feeling achingly empty. I heard murmurs of approval and appreciation from the watching household members.
“Andrea’s done very well so far this evening,” Dylan announced. “Her cooch is heavenly, I have to say. But I’m going to take her upstairs to her bedroom now, and finish claiming her.”