Kim Meets Master Jim

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Finally, she meets her pimp daddy.
2.8k words
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Master Jim
Master Jim
16 Followers

Their first encounter had been well planned. Since Kim and her master had already corresponded via email for some time and even chatted on the phone, they knew they were ready for the real thing at last.

Master Jim had booked the hotel room, stocked it with liquor, then went to the spacious lobby. He sat down and nonchalantly set the room key on the adjoining table. He waited for what seemed like an eternity.

Just a couple of minutes late, she walked in. And my, did she look fine, every bit as fine as her picture. Tall, slim, long straight blond hair. Plenty of blush and eye shadow, lips firetruck red. She had on a sleeveless silvery dress and black heels. She carried a small travel bag. She looked down as she walked, and appeared rather nervous, barely glancing up at him. She seemed somewhere between shy and terrified. But she took a good look at her new master, took a deep breath, and a faint hint of a smile flashed across her face as she picked up the key and turned and walked to the elevator.

Master Jim waited until he got the call.

"I'm ready for you, sir."

"Are you sure, Kim?"

"Yes, sir, I'm sure." Then a pause. "Please hurry."

He turned off the phone and strolled over to elevator.

He knocked on the door, even tho' he had an extra key. The door was opened by an adorable French maid, now with lots of black curly hair. She clasped her hands together in front of her and tried not to look him in the eye.

"I'm ready to serve you, Master Jim."

He walked in casually past her. She closed the door, and stood meekly behind him.

"Do you like my outfit, sir? I followed your instructions."

"Take my coat off."

She quickly did as she was told. She took his black leather jacket and hung it up, sneaking a quick whiff of the intoxicating leather, which gave her a rush.

He turned around, and now he began his inspection.

"Stand in front of me."

She was actually a hair taller than him, and in her heels she was hardly diminutive. Nevertheless, he was the one with command posture.

"Kneel."

She was getting nervous. Was he happy with the way she looked? Was she feminine enough, slutty enough? Please, please, she prayed to her Goddess, make him want me. Make him want to fuck me. I'll be so good to him.

He touched his hand to her face and lifted up her chin, so he could look her in the eyes. Was he angry, disappointed, disgusted, bored?

"You look lovely, Kim. My lovely little sissy slut Kim."

A feeling of wonderful relief flooded her soul. Thank you, Goddess, thank you. He wants me!

"Now stand up, turn around, and put your legs together and keep 'em straight. Bend over and put your hands on that table. Now!"

And now she began to feel the faintest stirring, the faintest tingle down in her loins. Yes, yes, I know it, he's going to bend me over, and rip my panties off, and spank me and rape me, just like he promised me so many times. Her head was beginning to swirl.

He gazed in quiet rapture at her black stockings. Seems up the back: ah, the classics! And not a bad hourglass figure, either. Good, she had put the corset on tight, as he had told her. He casually lifted up her little skirt and petticoat and checked to be sure she was wearing her black panties outside her garter belt as she had promised him ("for quicker access to my ass, sir"). He sat down on the edge of the bed.

"Get me a drink, then get on the floor in front of me, my little slut."

"Yes, sir!"

She minced over quickly and got the serving tray. She had him a Jack Daniels and soda in a heartbeat, served it to him kneeling, then she set the tray aside and immediately knelt down before him. He took a couple of swigs, seeming to ignore her for a moment, then set the glass aside.

"Put your hands behind your back, slut!"

No sooner had she clasped her hands behind herself than produced a pair of padded black cuffs and secured her hands. He sat back down in front of her.

"Come closer, darling. It's time now for you to become my sex slave in earnest. It's for real now – no more email, no more phone sex. You can't escape now. You won't leave here tonite until you have sucked a man's cock and swallowed his come. Do you understand me, bitch? You will suck my cock tonite."

"Yes, sir, I understand."

"Who understands?"

"Kim, your bottom bitch, understands you, sir?"

"What does Kim understand?"

"She understands that she has to suck your cock tonite, sir. She has to suck Master Jim's cock and swallow his come, or she won't be allowed to leave here."

"Good girl. Now nestle your sissy slut face right in your master's crotch, and inhale his scent."

"Oh, yes, yes sir. I want to smell you and smell your cock and your balls."

"And why is that, Kimmy? Why do you want to smell my cock and balls?"

She knew what to say. She needed no coaching, she only needed to let it all out.

"KimSlut needs it because she's a sissy fag, a cocksucking little fairy, she's a whore and a submissive slut and she needs her master's cock!"

And her master's cock needed her. She could feel it as she closed her eyes and rubbed her face in the crotch of his pants and inhaled deeply of the scent of a man. Her words and her nuzzling were beginning to work their magic.

"I'm going to help you, my little slut." He undid his belt and unbuttoned his trousers, and just slightly began to push down the elastic band of his silk briefs. She gasped in delight and anticipation. He paused to elicit a little whimper from her, then proceeded to lower his briefs. They brushed over the back of his cock and it began to pulse to life. She took one loving look at his manhood, and attacked.

He thought this would happen, and did not discipline her for her lack of restraint. They would both go with the flow this time. Her first blow job, and his first time with a TV slave.

She seemed to know exactly what she was doing, just as she knew exactly what she wanted when she engulfed his expanding cock with her mouth. She sucked like a famished babe. At last, she thought to herself, at last, I have a man's cock in my mouth, at last I'm sucking cock. I'm a faggot and a sissy and a cocksucker and a whore and I don't care because I am sucking the cock of the man who is my master. I'm going to make him feel so good...

She looked up at him and continued to suck. He reached his hand around the back of her head and pushed her closer, slowly but surely forcing his cock deeper into her throat, her eager virgin throat. And yes, just as she had written, he could feel his long prick push so deep down her throat that it was past the Point of No Return, past the Angle of the Dangle, deeper than any woman had sucked him before, he was not just in Kim's mouth, he was in her throat, and she was moaning with acceptance, not choking or gagging or fighting it. He drew back slightly, then pushed forward again, back and forth, back and forth...

And then it just happened. Master Jim simply let fire, he just let his wad blow right down his slave's throat. He felt it actually shooting into her throat, he felt her gulping and swallowing and even pushing herself closer to engulf more of his exploding manhood, until her nose was pressed against his pubic hair and there was no more cock to swallow. It was her first blow job, and she was already deep-throating. She knew she could never go back now.

They lay there in the beautiful silence for a long time, maybe longer than the time it had taken for Kim to suck her master to completion in the first place. Finally, he rose to his feet and brusquely pulled his tool out of his slaves' mouth.

"Lick it clean, bitch." He slapped her face with his cock, now soft but still extended a good six inches. Truth be known, there was precious little to clean up, but she did her duty and avidly licked his cock, and his balls, lapping up every bit of cum, sweat, and man musk that she could. This was so much better than fantasy, so much better than their cybersex games and nasty phone chats, as fun as those had been. This was real, this had a scent, she could finally feel and smell her master, not just read his words or look at his picture or hear his voice. His scent was already intoxicating her.

Now the second part of their first encounter began.

"Get on the bed and kneel down, bitch. Now!"

She did as she was told, quickly. She wasn't sure what to expect, other than the fact that he obviously wanted her ass.

He took his time laying out some items on the bed beside her: a small vibrator, a somewhat larger "G-spot" vibrator, a very life-like flesh-colored rubber dildo, a truly massive black dildo, some sort of inflatable device, and a tube of lube. With her head down of the pillow she looked over at his anal arsenal with the usual mixture of fear and desire.

SMACK!!

Her left butt cheek stung from the palm of his calloused hand.

"Do you remember what you wrote to me that one night? Do you remember, slut?"

Just the faintest whimper.

SMACK!!

"Answer me, dammit, you fuckin' little slut!"

"I, I don't remember, I said so many things, you always got me feeling so crazy...."

"You said, "Lots and lots of anal is what this slut needs!""

And now she did remember writing that to him one night. They had spent so many nights emailing each other outrageous dreams and filthy fantasies. She would dress up totally slutty, pop open a bottle of wine, grab a toy or two, and email him, praying that he would available to play. And yes, she remembered (vaguely) telling him those exact words one tipsy, horny night.

"Well, now your pimp daddy is gonna give his little KimSlut "Lots and lots of anal", so get ready to have your ass cherry popped."

"Oh, yes, yes, yes..."

"Yes what?"

"Yes sir, please, I'm ready"

And with that she reached back and with her fingertips, lovely and lacquered red, she lifted up her skirt, pulled her panties down to her knees, then spread her ass cheeks wide.

"Please fuck me! Please fuck my ass and take my ass cherry! I want it, Master. Please, sir," she whimpered.

Master Jim took off his boots and socks and his shirt, but left his "wife-beater" and jeans on. Then he got next to his little sissy slut on the bed. First came the lube. He let it pour out and run down her crack, flowing over her slightly puckered anus, down the seam, spreading over her balls like rapids hitting boulders, and running down off her semi-erect penis, mingling with her pre-cum before dripping down onto the towel she had so providentially placed on the bedspread. (The hotel maid would be so thankful.) The lube was lightly scented and rather warm. Oh, Goddess, she thought, thank you, he is so good to me.

She felt his fingertip move down her crack and over her anus, which caused her whole body to quiver a bit. Back and forth, up and down he ran his finger, playing with her puckered butthole, teasing it. Good girl, he thought, your hygiene is immaculate.

Then in plunged the first finger. He gave her the middle finger, flipped her off, so to speak, crooking it down ventrally on her. It was not big and was well lubricated, but still the swiftness with which he shifted from caressing her to penetrating her startled her. Again, a brief whimper, followed by a warm purr.

"Now I'm in you, my darling faggot. Finally, I'm in you."

Now two fingers entered her and continued the slow probing in and out. So far, so good, he thought. He reached down with his other hand and just lightly rubbed his fingers across the back of her cock, brushing it a bit back towards her rear. It was a light touch, but it had just the desired effect. She twitched and groaned as her cock responded to the pressure. He could feel a pulsing, a rhythmic tightening and releasing in her butt muscles.

He withdrew his fingers, but quickly her asshole was re-invaded by something else, something harder, bigger, and OH, OH, OOOHHH, it was vibrating, vibrating soooo gooood......

In and out, in and out, he worked the vibrator into her, and she kept her ass cheeks well spread to assist in her own anal violation. I'm such a fucking slut, she thought, such a fucking slut. Sometimes he twisted the vibrator from side to side as he plumbed her anal depths, watching the reactions he got from probing her in different direction, different spots, different depths. All her reactions seemed to be pleasurable ones, judging from her moaning, her rolled back eyes, and her drool on the pillow.

She began to feel other feelings in her ass. Faint tremors and stirrings, like a storm or earthquake coming. But then he pulled the vibrator out. Her asshole remained slightly agape for a few seconds, and he grinned as he savored the sight. As she looked back at her master over her shoulder, she realized how far she was sinking, the abject submission she had gotten herself into. A man was violating with her ass and she was letting him.

Next she felt something even larger invade her. Goddess, it was the dildo!

"I made this one myself, baby. Molded it mahself, exact replikka of yours truly", he chuckled, as he jammed it into her ass. She let out a sharp cry and her head snapped back. Then a shudder and she melted into submission again. Finally, she felt like she was accommodating her master.

He placed the vibrator right by her nose and told her to enjoy the fragrance of her own slutty asshole.

"Won't be much longer and it'll smell different. No more virgin smell. It'll start smelling like your master's cum. You'll get addicted to it, you fuckin' little butt slut."

It was pungent and not altogether unpleasant. Thank Goddess she had given herself an enema and purged herself thoroughly, just as he had told her. At least I'm clean, she thought.

She was really getting into the dildo fuck now, rocking back and forth with his thrusts, even milking the dildo with her rectal muscles. Once again, he lightly, almost accidently brushed a hand over her cock and balls, and got a full erection going almost immediately.

Just as she was enjoying the combined anal and genital play, he pushed the huge black dildo up to her face.

"Start sucking this big black cock now, slut. Start getting used to black cocks in your mouth. You know you want it and you know you're gonna get used as a black cock whore when I get done with you."

She opened her mouth without a second's hesitation and engulfed the massive black member. Heavenly.....she was filled orally and anally, her own hardened cock was being stroked by her master, and unspeakable scents filled her nostrils. She spread her ass cheeks even wider and began to pump harder and faster and buck and moan...

He squeezed her cock and screamed at her. "Come now, bitch! Come now or I'll squeeze your cock until you pass out! Come now, while you're filled front and rear, you fuckin' whore! Come now........."

And come she did. He watched, trembling himself, as her cock spasmed in a manly orgasm, even as her violated sissy ass throbbed and pulsed in unison, and her balls visibly twitched as they gave up juices. Wave after wave after wave of pleasure washed over her. Finally he released her cock and slowly let her anal muscles pop the dildo out of her ass. She collapsed on her belly on the bed, and he laid down next to her amidst the mess. He looked into her eyes, barely open, patted her ass, and smiled a satisfied smile.

"Who owns you, baby? Whose your pimp daddy?"

"You are, sir."

As they drifted off to sleep, he could just barely hear her whispers.

"Thank you, sir. Thank you."

Master Jim
Master Jim
16 Followers
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2 Comments
AnonymousAnonymousover 15 years ago
Love It

I love the stories of crossdressers submitting to a master.Its a real turn on.I am a crossdresser myself and want to try it. Love to read more of those...

AnonymousAnonymousalmost 17 years ago
A Big Hard-On

This one was a very good story.I started reading it,my cock got so hard thinking how you took into punishing her mouth&butt.Just wish I could see pictures of you doing it to her.Thanks for relieving my sperm too.May I join the fun too Master

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