Jim's Appointment
Jude Mason

"Seven o'clock, she says. Don't be late, she says. How am I supposed to know if her clock says the same as mine does?" Jim paced back and forth in front of the door, muttering, his stomach tightened as he checked his watch again. 'God, this thing feels tight,' he worried. 'Maybe I got a size too small. Fuck, I've never worn anything like this before.'

'Okay, it's time.' He checked up and down the street again, alone, thank God. Pulling the t-shirt off, he almost tossed it on the porch floor but thought better of it and folded it semi-neatly. Next, his loafers and socks, a tug in his crotch when he bent over made him shudder.

A last look around for onlooker then unbuttoned and unzipped, he let his loose, cotton slacks fall. They slid down his legs, and bundled around his ankles. Stepping out of them, he folded them and placed them with the rest of his clothes.

The unfamiliar breeze on his near nakedness aroused him. 'What if I get a hard-on?' he silently fretted. As if he'd prophesied, his cock pulsed, thickened. The small leather pouch lifted. 'No, no, don't for shit sakes; don't think about what's going to happen. Down boy, easy, this is our first meeting; don't get yourself in trouble before the door even opens.'

It didn't do any good, and he checked his watch. It was time. He knelt.

Tap, tap, tap against the door. He dropped his eyes and stared at the white panel at the bottom. The wood scraped his knees as he eased them apart a bit more. His pouch lost the battle and strained upwards, hiding very little of him. 

His heart pounded when the door opened.

Silence, time enough to wonder what the hell he was doing, kneeling in front of someone's door. Waiting for laughter, for her to acknowledge him, something, anything. Fear, humiliation as his cock pushed even harder against the tight leather pouch.

"Hello Jim." Finally she spoke. "Don't move. You're right on time; at least you won't begin with punishment. But, what's that I see poking out from between your legs?" A sharp-toed black stiletto nudged the pouch, jiggling his nuts.

"I'm sorry ma'am," he answered, while deep inside he begged, 'Oh God don't stop, it feels so good. Let me fuck your foot; let me rub my cock all over it.'

"Did you take your enema?" she asked. Her toe pressed upwards against his balls then slid back and tapped between his buttocks.

Gasping at the unfamiliar sensation, he clenched. Glancing up at her, dark hair pulled severely back, accentuating her sharp features. She'd chosen to wear his favourite outfit. A tight, dark skirt and white, silk blouse that she'd left unbuttoned enough to reveal her soft cleavage. A lacy white bra showed through the silk and he thought he could detect the darker points of her nipples. His erection throbbed.

"Answer me, worm," she snapped.

"Yes, Mistress Andrea," Jim replied courteously, castigating himself, 'Damn, if I don't pay attention I'll be in trouble for sure.'

"Good boy, now follow me. Don't rise." She turned and walked into a large room. Jim grabbed his clothing and tossed them inside the door, then quickly crawled after his mistress. It felt good to be crawling across carpeting rather than the wooden floor outside. He heard the door close behind him and wondered who, but obediently continued crawling.

"Get on the table, Jim." Andrea stood in the middle of the room beside a large wooden coffee table. There was an urgency in her voice that he hadn't noticed before and he hurried to comply. "Stay on your hands and knees for a minute," she said and retrieving two cushions from the floor, tapped one knee, "Lift up."

He raised his right leg high enough for her to push a pillow under it. She repeated on the left leg, and laughed as his knees slipped across the table, spreading his legs wide.

"Rise up so you're just on your knees," she said and when he rose, she slipped a sleep mask over his eyes.

'Oh God, I'm going to lose it, I'm going to cum without her even touching me,' he thought, basking in the sensation.

The inside of the pouch was slippery with the pre-cum that he'd been leaking since he'd looked at her. Straps wound around his thighs then pulled, exposed him further and he blushed behind the mask. A moment later, she drew his hands behind him and tied each to its corresponding ankle.

"Now my sweet, obedient slave, I want you to tell me your fantasy," she said from his left side.

"But, you already know what it is," he blurted without thinking. The unfamiliar whistle of a crop and a streak of fire laced his ass. He jerked forward, trying to avoid the pain, but his cock responded by throbbing with lust.

"Don't argue with me worm. Do it, now!" Mistress commanded.

"Yes, ma'am, I'm sorry for disobeying. I want to be used." He stopped. The reality of what he was doing sank in and he almost climaxed. 'Please, make it real.' His mind screamed. "I want you to make me serve you and your lover." He was glad she'd blindfolded him. There was no way he could have looked her in the eyes and said it. But, once started, the words came out in a rush. "I want to be used by you and your lover. To suck him off and have him fuck me. I want to clean out your pussy after he's fucked you, please Mistress."

The words came to a halt and he knelt, trembling, wanting. His heart thundered in his chest, close to bursting with excitement. Suddenly, the pouched fell away. Cock swaying, the tip shone wet with pre-cum.

"Yes, you want. Well, my sexy beast, I want too." Andrea's husky voice was at his ear. Her hands slid over his wide chest and tweaked nipples, suddenly taut.

Goose bumps puckered the flesh on his arms, his cock brushed against softness, skin, hers he prayed. It pulsed. 'Oh God, don't cum, not yet,' he wanted to scream. More hands gripped his hips and held him, while a tongue flicked across his shoulder. Hot breath brushed across his back as those lips trailed a line of wet fire down his back.

His trembling increased as someone's hands moved to his ass. Massaged the muscular globes, teased them apart and delved between. Fingers explored his well-lubricated bud, while he fought to keep breathing. Teeth, reminded him of the pain he'd earn if he disobeyed again, gently bit first one cheek, then the other.

When he thought he couldn't stand it any more, a mouth engulfed the head of his cock. More teeth, this time gripping him just behind the head, blessed him with a little pain. Gritting his teeth, he desperately fought for control, silently screaming for more. His balls tightened, but weren't left unattended for long. Gripped firmly, pulled down and held while a strap was affixed.

Inside, his mind babbled, 'Close, so fucking close, just a little more please!' Thigh muscles tensed mightily, straining against the leather that held him wide. He groaned as a finger pressed past the outer ring and entered his virgin ass. That familiar ache at the base of his spine, warned him of the impending climax, or so he thought. His balls churned, the sperm climbing up the shaft.

But, somehow they knew and both pulled away, just as he thought he'd made it. Left trembling, hips twitching with the need to thrust, into, against, something, anything.

"I hope you weren't thinking of cumming, Jim," Andrea said, breathlessly. "You haven't been given permission."

A masculine chuckle, behind him, affirmed what he already knew and he couldn't stop the smile, or the rush of excitement. "Mistress, please, I’m begging," he moaned.

"Please what?" A gruff male voice asked. "Begging for what?"

"Please," Jim began, stopped for a second, then blurted, "fuck me, oh God, fuck my ass."

"Good boy," Mistress Andrea said.

Hands pushed him forward. Whose didn't matter and he landed with his face pressed against a woman's sex. Soft, damp thighs trapped his head and he inhaled deeply, intoxicated by her sweet, musky scent. As if from a distance, he heard his mistress' command, "Make me cum."

Flicking out his tongue, he took his first taste of heaven. Soft and slippery, her labia slid into his mouth beautifully when he gently sucked. Fingers wound into his hair and pulled him hard against her. He moaned continually, unable to stop the sounds of pleasure that he bathed in. Slipping his tongue out, he entered her and groaned when she clenched her pussy around it.

He'd almost forgotten the man behind him, until something nudged between his cheeks.' Oh yeah, do it, do it,' his inner voice screamed. Spreading his knees as wide as he could, he pushed back against the welcome intruder. Pressure, as the muscles stretched before giving in, triumphant pleasure as the head popped inside his outer ring. Relaxing the muscle, he revelled in the sensation of having a man inside him for the first time.

Hot masculine hands on his hips, pulled him back. Hot man thighs pressed against the back of his, for the first time. Feeling so full, he thought he'd burst, but aching for more. Anus clenched, uncontrolled by him; feeling each ridge and vein of another man's cock. Intimately, so full, ah! 'Go slow, yeah, oh yeah.' He begged, but was afraid to speak aloud.

A man's cock gently sawed in and out of his ass. The inner muscles stretching as they never had before. Slowly going deeper and deeper, he was held and fucked. Attention brought back to his lady, his mistress, by the pressure of her fingers in his hair.

She gushed, sweet woman juice into his mouth and he lapped them up, seeking more. Her clit pressed against his lips, swelling into a tight knot and he rubbed his nose against it. Grinding his face into her, she cried out her pleasure and tensed. Thighs gripped his head tighter and he fought for breath. He tried to keep rubbing her clit as she bucked, but had no control.

He rocked between them, in a lust-filled haze of sensation. Each time the cock in his ass lunged forward, Andrea clenched and ground her cunt on his mouth. Nothing mattered by the tightness of his ass and the cunt in his mouth.

Their rhythm found and held, they soared for a time, but lost it when orgasm took hold. Jim's cries went unheeded as his rectum was awash in its first load of cum. Spasm after spasm blasted into him, and he blissfully accepted them. Nothing could have prepared him for the ecstasy he was experiencing.

His mistress finally released him and he took a deep breath. He couldn't move, bound as he was, and the man in his ass still held him close. An unfamiliar weight on his back, welcomed and wanted, Jim clenched on the cock inside him. A hand reached around for his, and found it spent. His ejaculation had gone unnoticed; the pool beneath him, a reason for punishment if one was needed.

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End