He picked up the crop, and slowly ran it over his fingers as he fixed her with his deep brown eyes…
“Oh my darling, how I’ve dreamt of this moment,” he murmured in her ear as he tied the strip of cloth over her mouth, and pressed her hands firmly on the bedframe. With a soft kiss on the top of her head, he ran his fingers up the inside of her legs, pulled her little silk skirt up around her waist, and slid one of the pillows under her hips. Her bottom was instantly raised and pert, the round cheeks just begging for his ministrations and sweet chastisements.
With a cheeky smile, he bit one of her buttocks through the thin cloth of her knickers, and asked, “Are you going to lie there like a good girl while I tend to your lovely bottom?”
She moaned, and lifted her hips, offering her ass to him with total willing. She started to reply with the words she longed to say: “Yes, my sweet. I’ve been longing for this, too. I promise I’ll be good”, but as soon as she began to move her lips, she was reminded of the linen gag around her mouth. She settled instead for a muffled “uh-huh” sound in the back of her throat, and a fluttering of her lashes as she looked back at him, eagerly.
He reached beneath her and lowered her panties past the stay-ups he’d requested she wear for their date, and down to her knees. Bent this close to her, he could already smell the warm musk of her arousal rising from between her legs.
He strode purposefully to the dresser where he had laid out his implements, the array of wicked utensils set out neatly. He picked up the soft leather paddle first; he wanted to make sure her bottom was flushed and warmed-up before he employed the cruelest of his arsenal.
He tested the paddle against the palm of his hand, enjoying the slap of the leather and the hunger in her eyes as she looked back at him. She wanted it, he could tell, and he was more than happy to oblige. As he began to slap the flat of the soft leather paddle against the fleshy globes of her bottom, he relished the sight of her arching her back and lifting her rear towards him. With her bottom raised like so, he could see the dark blush of her labia, puffy and damp, the wetness starting to glisten invitingly from between her legs.
With each slap of the padded leather, the blood rose to the surface of her buttocks. The sight of her reddened cheeks and the smell of her sex sent pulsing pleasure straight to his member. He was thankful he had undressed early on in the proceedings; he would have been too preoccupied with his naughty but loving punishments to have stripped now, and his cock was hardening rapidly as she, sufficiently warmed up now and eager for more, began to moan behind the gag.
He returned the paddle to the dresser and smirked as he heard her make a little sound of disappointment.
“Oh, don’t worry, my angel,” he chuckled, as he approached the bed, reached under her breasts and lifted her top so that her bare globes could brush against the wool of the bedspread. “I’m by no means finished with that ripe, red ass of yours.”
He punctuated his statement with a hard smack on her bottom, and was delighted when she gasped, her body jolted from both the surprise and the delicious sting.
Returning to the dresser, he picked up the crop, and slowly ran it over his fingers as he fixed her with his deep brown eyes. He saw the flash of fear and excitement cross her face, and teasingly brought the black rod down hard on his palm. The sound of the crop cutting through the air made his cock twitch, and he smiled as he saw the ambrosial fluids leaking freely now from her slit.
“Hnnnn,” she groaned, as he stepped towards the bed. With a quick whipping motion, he brought the crop down hard, right across her ass, and she gave a strangled cry. He saw a red welt start to form almost immediately, and grinned. He struck again, slightly lower this time, and when she writhed awkwardly and squeezed her eyes shut, he felt a deep throbbing in his balls.
He gave her twenty blows in quick succession, and with each one, her cries grew louder until, by the end, she was shrieking. The long red lines from the crop’s impact were developing into beautiful raised marks all over her ass and her “thuttocks”- that soft and super-sensitive skin just between the thighs and the buttocks. He held the crop by his side for a moment and rubbed her stinging flesh as she keened, her eyes damp with tears, her breathing ragged and shaking.
“Good girl,” he murmured appreciatively, as he soothed and stroked her bottom. “You’re certainly taking your chastisement very well so far. But I wonder how you will manage with a little something extra?…”
With a wicked glint in his eye, he produced a long, deeply ridged dildo made of pale purple glass. He saw with delight that her eyelids flickered, but for a second she looked hesitant. He waited a moment, unsure if her look meant that she was about to safe-word, and without saying anything, he softened his eyes and raised his eyebrows, silently asking, “You okay?”
She responded with a slow nod, and behind the cloth gag, he saw her give a faint smile. He couldn’t help but blow her a kiss; his brave angel, willing to trust him to take her to the brink, but never to exceed her boundaries and hard limits.
He smeared some lube over the dildo and slid it slowly between her smarting cheeks. She gave a little moan when the cold tip of the glass toy touched her asshole, and he began to rub it gently against the tight opening. Where she had seemed tentative before, now she lifted herself slightly on her knees and bent her ass towards him, her cheeks spreading as she offered herself up to his slick probing toy with its cold, wet touch.
He pressed harder, and slowly began to introduce the dildo into the tight ring of her asshole. She gasped, but he knew that it was pleasure rather than pain that had made her breath hitch. Her cunt was soaking now. Indeed, her wetness was dripping from her and onto the pillow beneath her trembling hips. He continued to penetrate her slowly but firmly, and as he felt the tight circle of muscle give way and the toy slip into place, he couldn’t stifle his own moan.
With gentle movements he maneuvered the dildo slowly inside her, savoring the sound of her moans and the wet slide of the toy in her ass. Just a small amount of resistance to begin with, but as the friction of the dildo worked the muscle and the glass began to warm to her body temperature, the motion became smoother and easier. It wasn’t very long before he was able to increase the speed of his movements, and then to start thrusting the dildo in and out with a brisk, yet sensuous rhythm.
She twisted and arched her hips, the feeling of delicious fullness making her cunt twitch and her clit ache with maddening need. She wanted so much to reach down under her hips and between her legs, and to stroke her engorged pearl while he fucked her ass with the glass toy, the sensation of the ridged glass combining with the quick, hard rubbing of her clit to send her screaming over the precipice. But she was determined to be his good girl, and so, though her body keened with longing and a delirious desire to explode into a shuddering climax, she maintained her grip on the cold steel of the bedframe.
As he worked the dildo harder and faster, he raised the crop in his other hand and, with expert dexterity, thwacked mercilessly at her buttocks. She shrieked loudly, then bit down on the cloth against her mouth. It was soaked with her saliva, and as she gritted and clenched her mouth she felt the awkward grind of wet linen against her the edge of her teeth. It was uncomfortable, but she kept biting down, bracing and twisting to avoid the stinging blows yet raising her raw and slowly-bruising bottom towards the thrusts of the teasingly textured purple glass.
Suddenly, he dropped the crop onto the bed and, with the dildo still filling her ass, he grabbed her hips, tilted her pelvis toward his groin and with one hard thrust, buried his throbbing, rigid cock inside her cunt. They both grunted in unison, and within seconds they were coming, all slamming hips and desperate cries and viscous fluids. He pulled his prick out of her quickly, in order to spill on her bottom, and as his white liquid painted her bright red buttocks, he gave another couple of thrusts of the dildo and drew it out slowly. She could feel every single millimeter of the ridged glass slipping from her asshole, as his warm semen coated the raised and stinging welts on her bottom, and she gave a satisfied sigh.
This fellow, she thought to herself, has definitely been worth the wait.
©️ Jupiter Grant, 2021
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