Chapter 19: Thoroughly Broken In

Continued from chapter 18:

Madison turns to Erica with a wicked smirk.

“Keep going until she's bawling uncontrollably. I want to hear her scream for us.”

Erica obeys enthusiastically, targeting my sit spots. She lights a fire that proves too much to bear, and my anguished wails reach a fever pitch.

POP! POP! POP! POP! POP!

I writhe in agony as Erica's final strike ignites my bottom, a howl of surrender escaping my lips. Through a veil of tears, I see Madison, Lauren, Prim, and Anna laughing at me, their amusement complete. Erica, finished with her torment, grasps me by the handle of the plug lodged within me and helps me off her lap.

“Lauren, I think it's your turn,” Erica says, a wicked smile playing on her lips.

“Do you want him over your knee, or should we put him on his back on the coffee table, diaper position? If we hold his legs up, you can really get in there with the belt...and I think she's probably stretched enough for the beads.”

She turns to the others. “Girls, what do you think?”

Chapter 19:

Madison considers the options, tapping a perfectly manicured nail against her chin.

“Hmm, both positions have their merits. But I think putting Sydney on her back might be more...visually stimulating for all of us.”

She turns to me with a wicked grin.

“Hear that, pet? We're going to put you on display like the sissy girl you are. Lauren will have full access to your most intimate places while we all watch and enjoy the show.”

Madison addresses the group.

“Prim, Anna, why don't you two help position our little sassy pants on the coffee table? Hold those legs high and wide—I want to see everything. And Lauren, grab that belt. Let's really make Sydney earn her release.”

The girls move swiftly, dragging me onto the cold surface of the coffee table. I am held down on my back, legs held high and wide by Anna and Prim, who grin down at me with gleeful anticipation.

Erica and Madison pin my hands above my head, their grips firm and unyielding. Lauren's grinning face appears between my legs, her eyes gleaming with malice.

“Let's get you unplugged, shall we, Sydney?” Lauren asks, her voice sweetly venomous.

I feel a sudden pressure as Lauren gently twists and tugs at the plug until it comes out with a lewd popping sound.

The emptiness is fleeting as Lauren quickly requests, “Erica, can I have the lube and the anal beads, please? I want to get these inside Sydney before I belt her.”

Madison nods approvingly at Lauren's request.

“An excellent idea. We need to make sure Sydney’s holes are nice and ready for us.”

She watches intently as Lauren liberally applies lube to the anal beads, her voice dripping with sadistic glee.

“Go on then, sweetheart. Work those beads nice and deep. I want to see them disappearing into our little Sydney’s greedy bottom.”

Lauren presses the slick tip of the beads against my exposed hole, slowly pushing them past the tight ring of muscle. Inch after inch disappears inside me as she works them deeper, twisting and turning to stimulate my inner walls. Madison leans in close, her breath hot against my ear.

“Doesn't that feel amazing, pet? Having your slutty hole filled and stretched for our pleasure? Just wait until we really start using you like the fucktoy you are,” she whispers.

An erotic pleasure surges through me as the beads fill my anus, only the jeweled pull ring visible outside my winking rosebud. Lauren's face appears between my legs again, and she snaps a doubled-up leather belt ominously between her hands.

Madison's eyes glitter with malicious anticipation as she watches Lauren double up the belt.

“Oh, this is going to be so much fun. I can't wait to see those beautiful welts appearing on Sydney’s tender skin.”

She turns to me, her voice low and threatening.

“Remember, pet, you're going to count each strike out loud for us. And if you miss a single number, well...let's just say the punishment will be severe. Now, present yourself like a good boy and take what you deserve.”

Lauren raises the belt high, the leather end cracking through the air as she aims for my exposed bottom. The first blow lands hard across both cheeks, leaving a vivid red stripe in its wake.

Counting is impossible. I shriek and gibber and wail as Lauren destroys my bottom with the belt. The sound of leather against flesh fills the room, each strike sending waves of fiery pain through me.

SNAP! SNAP! SNAP! SNAP! SNAP!

Prim and Anna hold me open for her, Anna's small, gentle hand reaching down to cover and protect my limp penis and shriveled testicles, moving them out of the way of the belt. Madison and Erica hold my hands above my head as I surrender to the brutal ****.

Madison watches the brutal belting with rapt attention, her eyes feasting on the way my skin blooms with angry red welts.

SNAP! SNAP! SNAP! SNAP! SNAP!

“That's it, Lauren! Snap your wrist a little more on your follow through. Our little Sydney needs to be thoroughly broken in.”

She notices Anna's protective gesture and smirks.

“Aw, isn't that sweet? Anna trying to shield our little guy’s delicate bits. But I think it's time we paid some attention to that pathetic little cock, don't you girls?”

Lauren, if you could help Erica hold him down...that would be great. Prim, you and Anna keep his legs up if you please, but if you could lift his hips a bit, we can aim his penis at his face, once it gets hard enough.”

“Anna wanted to give him a facial, and since she wasn’t there for the first one, it’s only fair she gets to participate in this one.”

Lauren and Erica take hold of my wrists, pinning me down, their faces alight with sadistic delight. Prim and Anna guide my ankles above my head, my limp penis dangling before my eyes.

Madison appears in my vision between Prim and Anna, coating her hands generously with lubrication.

“We're going to milk you now, Sydney. You're getting your first release of the evening. Can you guess where we're going to make you do it?” she asks, her voice dripping with malice.

She nods to Prim and Anna, who begin to pepper my angry red bottom with crisp, stinging spanks. I feel one of Madison's hands tug gently at the ring that protrudes from my anus, the one attached to the beads. The other cups my testicles, strokes my length, covering me in shiny lubrication, bringing me back to full erection.

Madison grins wickedly as she sees me coming back to full hardness, my cock now pointing directly at my own face thanks to Prim and Anna's positioning.

“Mmm, looks like our little Sydney is getting nice and excited. Aren't you, pet?”

She gives my balls a firm squeeze, rolling them in her slick palm as her other hand slowly, teasingly begins to apply tension to the ring attached to the anal beads.

“That's it, nice and easy.”

To be continued in chapter 20...