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Mistress Fucks Jim’s Sissy Ass

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Author's Notes

"My firs story written for this page. Hope you enjoy! Feedback is welcome."

When I walk into the studio, my heels click on the hardwood floor. My client jumps in anticipation, and he tracks the sound. He’s blindfolded and waiting for me on his knees like he was instructed to. There’s a flush to his hairless chest, and I smirk, my red-painted lips quirking to the side.

It’s his first time, and I love breaking in the virgins.

My studio is spacious but cozy. Hardwood floors covered in rugs and leather furniture. There’s other various equipment lined against the brick walls, but I don’t plan to use that on him today. Not until he’s ready.

I stand in front of him, glancing down. My client’s name is Jim, and he’s about as average as you can get. Late forties, thinning brown hair, and soft in the middle. He’s naked now except for his briefs and his blindfold. I don’t know what brought him in here—if it was the stress of work or unsatisfying sex with the wife—I really don’t care. He’s willing, and he’s paying.

I toss my long blonde ponytail over my shoulder and adjust my pleated black leather skirt before crouching in front of him. He smells like sweat and desperation. My favorite.

“Jim,” I say, pushing his blindfold up so he can see me.

“Yes, mistress?” he replies, blinking, his voice breathy. I notice the bulge in his briefs begins to rise.

“Are you ready to have your ass pounded?”

He nods eagerly. “Yes, mistress. I am your slut to use.”

I smile sweetly and pull the blindfold down. “Good boy.” I stand. “Open your mouth.”

He does, and I line my plastic, matte black cock with his waiting mouth. It slides in effortlessly, and he begins sucking and licking it. His hands stay by his sides, and he bobs his head, lubing up my cock with his spit. When I’m convinced he’s done a good job, I instruct him to stop. He obeys immediately.

“Turn around,” I instruct. “Briefs off and ass up.”

He’s quick to follow my instructions, and within seconds his undergarments are discarded on the rug, and he’s on all fours. His ass is hairless and clean and I’m almost impressed. For a newb, he’s managed to prep himself immaculately.

I pad over to the small table by the couch and open a drawer, pulling out a bottle of lube. I walk back over to him and cover my thumb. I place my thumb on the top of his ass, so he can feel my intentions. He shivers again, but doesn’t object, so i slide my lubed thumb to his ass. I run it along his puckered hole, coaxing him to open up.

“Relax,” I murmur.

He does and I’m able to pass through his sphincter with my thumb. He groans and I peek around his body to see his cock is hard and dripping precum. He’s of average length and thickness. Proabably just enough to bed and breed some housewife before he came seeking me.

My fingers trade places and soon my hole index finger is sliding in and out of his eager ass. He’s moving back and forth in motion with my finger and I allow it for a minute before I tell him to stop. He’s going to cum too soon if he keeps it up.

“I’m going to fuck you with my cock now,” I tell him.

“Yes, mistress, please!” he says, his voice strained.

I chuckle and grasp my cock, circling his bud. He pushes against me and i slap his ass in warning.

“I will choose the pace we move at,” I remind him.

He whimpers and bobs his head.

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I continue, pushing the head of my lubed cock into his ass. He’s tighter than all hell, but the fingering i did loosened him up just enough. Soon the head pops in and I give him a minute to adjust. Then I continue, sliding my cock into the length of his ass. When I’m fully seated in his ass, he lets out a long groan.

I peek at his cock again to see it rigid and leaking more precum. I smirk and give it a flick. He jumps. “You’re not going to last long at all, are you?”

He whimpers and a flush spreads along his cheeks.

I grip his hips and pull out slowly. He moans, his fists balling up and he arches his back. When most of my length is out, i start to push it back in. And then I’m slowly fucking him, my cock sliding in and out of his readied ass. His moans morph into cries and pants. I pick up my pace and soon I’m fucking his ass like he’s a whore, my nails dipping into the soft flesh of his hips. He’s bucking back against me and i let him.

“Oh, mistress,” he moans. "Oh, you’re fucking me so good. I’m your little sissy slut to use. Fuck me please.”

I pick up my pace and grab onto his shoulder, fucking him with more gusto. I smile, listening to his hollers of pleasure. Vocal men are so amusing. Sweat beads along my hairline as I continue pounding his ass.

“Mistress…” he pants, and I know where this is going.

I stop, sliding my cock from his ass with a wet pop.

He cries out at the emptiness, and I slap his ass again. “No whining. Now flip on your back.”

Jim switches positions, lying on the carpet with his legs up as high as they’ll go. His balls are shaved smooth along with his pubic area. His cock stands tall, quaking like the rest of him. I grab his ankles and position my cock against his gaping hole. It slides in with ease, and I resume fucking him. His panting and moaning return.

“Thank you, mistress,” he says. “I’m so honored to be fucked by you.”

“You are,” I agree with a grunt. I slow my thrusts, making them more deliberate and forceful. “This is such a lovely ass to fuck. You’re such a good, sissy boy, Jim.”

He cries out in pleasure at my forceful thrusts. “Oh mistress!”

I scoop some leftover lube from his ass and smear it on his cock, moving my hand up and down. “Are you close to cumming Jim?”

He nods, his face twisted in sweet agony. “Yes, please let me cum, mistress. I’m so desperate for release. You’ve fucked my ass so well.”

I smile, my hand moving up and down the length of his cock before letting my thumb slide over the head, wiping away the drop of precum. “Hmm. I suppose you’ve behaved well enough. You may cum, Jim.”

I pick up the pace of my thrusting, going fast and hard into his ass. I stroke his cock in unison and a few seconds later he’s exploding. Cum shoots from his cock, landing on his stomach in three good spurts before oozing out of the head and onto my hand. Jim sings with pleasure, his voice breathy as he chants. I slow my movements and release my hand from his twitching cock.

I lean forward, ripping his blindfold off. “Did you enjoy yourself, you sissy slut?”

He looks dazed, but smiles and nods. “Yes… thank you, mistress.”

I chuckle, pulling my cock from his ass, and stand. I stretch my legs before turning to strut out of the room, giving Jim a little wave. “See you next time. Remember, the bathroom is down the hall. Clean yourself up and make another appointment with my assistant, Jessica.”

“Yes, mistress.”

Published 
Written by CuriousLove96
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