BDSM Stories: Chastity Cages & Cuckolding Dates

The click-clack of Mistress’ boots on the hardwood floor drew closer. The slight jump of my heartbeat and chastity cage signalled both anticipation and a slight fear as she drew near. A stern, “Down boy,” instructs me to my knees, where my eyes gaze upon the buttery dark leather of Mistress’ boots.

Their softness and glow in the warm light contrasts the hard, confident rhythm of the echoey heels on hardwood—the drumbeat that calls my attention. With two outstretched fingers, Mistress gently instructs my chin to look up towards her face where she gives a slight smile anticipating the disappointment I will soon receive.

“I need you to prepare the bed and house for my return. Fresh linens, a swept floor, chilled wine, and two robes on the bed, darling.” Her smile grows wider. “You know how I like it when I return with a stud. Now, kiss my leather boot.”

After doing so, I rise to help Mistress with her coat—black leather, of course—and see her out the door. As she turns to go, a sudden firm grasp at my sack pulls me closer to her. The metal chastity device she placed on weeks ago pinches my cock between her hands.

My breath leaves me as she says, “And don’t forget, Mommy needs your credit card for the evening. That little device you’re wearing won’t be coming off until your debt is paid, boy.”

She pauses, smiling, “And, I’ll need you to pick us up when we call. Don’t be late.” I hand her my credit card as she leaves, and she gives a few gentle taps to my cheeks, saying, “You’ll learn to love this,” before heading out the door.

I diligently tend to the chores at hand, and await the call to tend to her and her stud—a banker by trade. Hours later Mistress texts, “Come. Sit at the opposite end of the bar and wait for us to finish.”

As I enter the bar, I see her hand firmly planted on his thigh. She sees me enter, and with one eye fixed on me, she leans in to him for a gentle kiss. She smiles, and my heart sinks.

I look out of place in the low lit, high class bar, as her presence radiates, turning the heads of all who pass by. The bill arrives and she promptly pulls out my credit card to pay—the marriage of findom and cuckolding.

Just as quickly, she and her lover get up, and without breaking stride or looking at me as they walk out she curtly says, “Come.”

After a long car ride home, with Mistress and her lover building anticipation through teasing, we arrive at the apartment.

“Tend to my boots,” Mistress calls as she sits in her chair by the doorway, and I work to unfasten each elegantly detailed button on her boots.

“Bring us some wine, you wench,” she laughs as she begins to bring her lover closer. They make their way to the bedroom, and I am left outside, awaiting the next order.

Eventually a tiny service bell rings. I knock gently before entering.

“Come boy. Fetch us some warm towels.” I do as instructed, and return—ordered to clean the cum from the bed and the little dribbles just outside Mistress’ beautiful vagina.

“Now, wipe us down with new towels.” I dampen some hand towels, and return, instructed to clean his still hard cock before turning to Mistress. Small beads of sweat have collected all over her face. The room is rich with her scent and warmth.

I gently massage Mistress with the towels from toe to head and back down again. “Kiss them,” she says, pointing to her toes. Her lover steps out to shower.

“Now, I need you to make me cum, and to clean me out.” I kneel at the foot of the bed as Mistress eases herself into position, my chastity device growing tighter. The scent is intoxicating as I gently move my tongue side to side across her clit.

“Harder,” she commands as she reaches for a nearby riding crop.

Whack! Whack!

She strikes hard across my bare back as instruction. She then pulls on the leash of my collar, smothering me closer into her, her excitement rising. Her leg shifts to expose more of herself, and rests heavy on my shoulder.

My tongue steadily builds momentum as she pulls harder on the collar. Her fingers augment my tongue motions. Soon, her body shakes in elation as she orgasms. A smile grows across her face. She allows me to kiss her fingers, fresh with the scent of her body—a departing gift as I am sent away once more.

As I stand to leave the room, she grabs my caged cock, now throbbing with pain from all the excitement. She slaps the top of the chastity cage hard several times, and says, “Mommy makes sure this pleasure is all hers.”

A sadistic smile shows her dark red lips once more. “We know you can’t be trusted, boy,” as she checks the lock on my chastity cage. Her lover returns and she turns once more to caress his body, reminding me of my place as a cuckold.

“Be gone, boy, but remain near in case Mistress needs you.”

I close the door and kneel a few feet outside the room once again. Waiting.

This is part of my BDSM Stories writing contest, contributed by an eager submissive. Want a more intimate look into my personal relationships? Follow me on my OnlyFans or AVN Stars. Don’t forget to sign up for my newsletter and for those who feel inspired by the above interview, reach out.