Novel: From Husband to Locked Sissy Maid: The Halloween Transformation: Chapter 14

Charlene pressed the thick head of the strap-on against his stretched hole, letting the weight of it rest there for a moment. She slapped his right cheek hard, the sound sharp in the quiet room.

"Do you still consent to the bet? Do you still consent to me being the boss tonight?"

Mark's fingers clutched at the sheets. His voice came out shaky but clear. "Yes. I consent."

She pushed forward. The head breached him slowly, stretching the ring of muscle wider around the slick silicone. Mark groaned into the mattress, his caged cock twitching uselessly. Another slap landed on his left cheek, harder this time.

"Louder."

"Yes! I consent!"

Charlene drove another inch inside. The curved shaft pressed against his prostate, making his trapped cock leak a steady stream of clear fluid that dripped onto the sheets. She gave him two more inches, then paused, letting him adjust to the thickness filling him.

"Open wide," she ordered.

She reached for the black dildo gag on the nightstand. Mark opened his mouth obediently, consenting to this. She slid the thick rubber shaft between his lips, pressing it deep until the base rested against his teeth. The locking strap went around his head, the buckle clicking shut at the back of his skull. He was completely silenced now, drooling around the gag.

Charlene gripped his hips and thrust forward, sinking another three inches into his ass in one smooth motion. Mark's whole body jerked. The fake tits swung beneath him, the nipple clamps pulling tight with every movement.

She pulled back halfway, then drove in again, establishing a rhythm. Each thrust went deeper than the last.

"My bitch," she growled, slapping his ass again. "My locked-up slut." Another thrust, harder. "My sissy maid who takes whatever I give her."

Mark moaned around the gag, the sound muffled and desperate. His cock strained against the pink steel cage, leaking constantly now. The sheets beneath him were already damp with his arousal.

Charlene adjusted her stance and drove the full ten inches home in one long thrust. The harness pressed flush against his burning cheeks. Mark's muffled moan vibrated through the gag as she bottomed out inside him.

She held there for a moment, letting him feel every inch buried in his ass. Then she started fucking him in earnest—long, deep strokes that pulled almost all the way out before slamming back in. The wet sound of the strap-on moving in and out of his lubed hole filled the room.

"That's it," she panted. "Take every inch like the sissy you are." Her hips snapped forward again and again. "My property. My toy. My fuckhole."

Mark's moans grew louder around the gag with each thrust. His body rocked forward on the bed, the bells on his heels jingling with every movement. The chastity cage remained painfully tight around his swollen cock, denying him any real release while Charlene used him exactly as she pleased.

She reached down and grabbed a handful of his blonde wig, pulling his head back as she pounded into him. "This is what you agreed to," she reminded him, her voice thick with arousal. "This is what you consented to."

The strap-on disappeared completely inside him with every thrust now, the harness slapping against his marked cheeks. Mark's muffled sounds grew more orgasmic, his body trembling as she claimed him completely.

Mark's body jolted forward, his caged cock swinging uselessly beneath him while clear fluid continued to leak from the tiny slit in the pink steel.

She pulled back until only the head remained inside, then slammed forward again. The wet sound of the dildo fucking his lubed hole filled the bedroom. Each thrust forced a muffled moan from around the thick gag strapped between his teeth. Drool ran down his chin and soaked into the sheets.

"Take it, slut," she growled, slapping his right ass cheek hard enough to leave a red handprint over the temporary tattoo. "My sissy maid loves getting fucked like this, doesn't she?"

Mark's fingers twisted in the sheets. The nipple clamps tugged with every movement, sending sharp sparks of pain and pleasure through his fake tits. The bells on his pink heels jingled with each thrust as Charlene pounded into him.

He couldn’t believe he was so turned on by this. He completely consented to this.

She reached down and grabbed a handful of his blonde wig, yanking his head back. "Answer me, bitch."

"Mmmph!" was all he could manage around the thick dildo gag. His muffled sounds only made her thrust harder.

"That's what I thought." She released his wig and brought both hands down on his ass, spanking him in rhythm with her thrusts. "My locked-up whore. My property. My fucktoy."

The keys between her breasts bounced and jingled with every movement, catching the light as her latex-covered tits swayed. The sight of them reminded Mark exactly who held control—his wife, his keyholder, the woman currently buried balls-deep in his ass.

Charlene's first orgasm hit without warning. Her hips stuttered, the strap-on buried to the hilt as her pussy clenched around nothing. She moaned loudly, grinding the base of the harness against her clit while Mark's hole spasmed around the thick shaft. Her thighs trembled against his burning cheeks.

She barely paused before starting up again, fucking him with renewed intensity. "Did you feel that, sissy? Your wife just came from fucking your ass." Another hard slap landed on his left cheek. "And I'm not done with you yet."

Mark's cock strained desperately inside the pink cage, the metal pressing tight against his swollen flesh. Every thrust against his prostate forced more clear fluid to drip from the cage, forming a growing wet spot on the sheets beneath him. He couldn't believe how turned on he was—humiliated, used, completely at her mercy, and harder than he'd ever been in his life.

Charlene grabbed his hips and changed the angle, driving the curved shaft directly into his prostate with each thrust. "Look at you leaking like a broken faucet. My little sissy maid can't stop dripping while I wreck her hole."

She fucked him harder, the wet squelch of the strap-on moving in and out of him growing louder. Mark's moans grew more desperate around the gag, his body rocking forward with each powerful thrust. The fake breasts swung beneath him, the nipple clamps pulling and twisting with every movement.

"My bitch," she panted, slapping his ass again. "My slut. My sissy maid who takes whatever I give her." Another orgasm built in her core as she watched him take every inch. "And you're going to take it all night if I want."

The second orgasm crashed through her harder than the first. She pressed forward, burying the full length inside him as her body shook with pleasure. The keys jingled wildly between her bouncing tits. Mark felt every tremor through the harness pressed against his ass.

She pulled back and started fucking him again immediately, not giving him a moment to recover. Long, deep strokes that pulled almost completely out before slamming back in. The harness slapped against his tender cheeks with each thrust.

"You consented to this," she reminded him, her voice thick with arousal. "You said yes when I asked if you still wanted the bet. Now you're getting exactly what you agreed to."

Mark's muffled moans of pain and pleasure grew louder around the gag as she drove into him relentlessly. His body trembled beneath her, caught between the overwhelming sensation of being fucked and the constant denial of his trapped cock. The chastity cage remained painfully tight, his balls aching with denied release while Charlene used him for her pleasure.

She reached around and grabbed the base of the strap-on, angling it differently as she fucked him with short, hard thrusts that kept constant pressure on his prostate. "Cum for me, sissy. Show me how much you love being my fuckhole."

Mark's whole body seized as the prostate stimulation pushed him over the edge. Clear fluid spurted from the cage in weak pulses, his cock twitching uselessly inside the pink steel while Charlene continued pounding into him. The orgasm was ruined, unsatisfying, leaving him even more desperate and sensitive.

"That's it," she cooed, never slowing her thrusts. "My sissy maid came from getting fucked in the ass. How pathetic. How perfect."

She drove the strap-on home one final time, grinding against him as a third orgasm rolled through her body. The keys between her breasts caught the light with each panting breath. Mark lay beneath her, trembling and used, the full ten inches buried inside him while drool ran down his chin around the locked gag. 

He couldn’t believe it as he pushed back into the strap-on, hungry for more of her cock. He didn’t just consent to this, he wanted it with a desire he never thought he would have.

Charlene stayed buried inside him, letting him feel every inch as she caught her breath. Her hands stroked over his burning ass cheeks, tracing the temporary tattoos that marked him as her property.

"We're not done yet," she whispered, pulling back slowly. "The night is just getting started, my little sissy maid."

"This ass belongs to me now," she growled, slapping his right cheek hard. The sound cracked through the bedroom. "My sissy maid's fuckhole. My property."

She set a brutal pace, the harness slapping against his burning cheeks with every thrust. The curved shaft dragged over his prostate on each stroke, forcing more clear fluid to drip from the tiny slit in his pink cage. Mark's muffled moans of pleasure grew louder around the thick dildo gag, drool running down his chin and soaking into the sheets beneath him.

Charlene reached around and grabbed his fake tits, squeezing the heavy silicone while she pounded into him. The nipple clamps tugged with every movement, sending sharp jolts through his chest. "Look at you, taking my cock like a desperate whore. My alpha husband reduced to a leaking sissy maid getting fucked in the ass."

She pulled back until just the head remained inside, then slammed forward again. The wet squelch of the strap-on moving in and out of his stretched hole filled the room. Mark's fingers twisted in the sheets, his body rocking forward with each powerful thrust. The bells on his pink heels jingled wildly.

"I'm going to fuck every drop of cum out of those balls," she promised, reaching down to grab his trapped testicles. She squeezed them firmly while continuing to drive the dildo deep. "Make you cum from getting your ass wrecked."

Charlene pulled back slowly, letting the curved shaft drag over his sensitive prostate one last time. With a wet, obscene sound, the thick head popped free of his stretched hole. The ten-inch dildo glistened with lube as she stepped back, admiring the way his gaping ass twitched and clenched around nothing.

She reached for the pink plug on the nightstand and pressed the tapered tip against his open hole. The silicone slid in easily, stretching him wide before the thickest part popped past his rim. His hole swallowed the plug greedily, the base settling flush against his tattooed cheeks.

Charlene leaned over his trembling body, her latex-covered breasts pressing against his back. Her lips brushed his ear as she whispered, voice husky with satisfaction.

"I am the alpha in this relationship now. Your sissy transformation is only just beginning."

She gave the plug a firm push, seating it deeper inside him. Mark whimpered around the gag, his body shaking with exhaustion and overstimulation. The bells on his pink heels jingled softly as his legs trembled.

Charlene straightened up and unbuckled the harness, letting it drop to the floor. She ran her hands over his marked ass cheeks one more time, tracing the humiliating tattoos that declared him her property.

"Get some rest, sissy maid," she said, giving his plugged ass a light slap. "Tomorrow we start the next stage of your transformation."