Page 54 of Rory: His to Discipline

Tess had no intention of moving, in fact she was so relaxed she was afraid she would doze off.

A thin stream of oil dribbled from her shoulder blades to her buttocks and she jumped a bit before his big hands began to move over her again. Although her entire body from her neck to the soles of her feet were caressed and soothed, by far the most attention was devoted to her ass.

Oil was added repeatedly to that part of her anatomy until she was slippery and pliant. Rory’s fingers made occasional forays between her thighs, gliding lightly over her clit and circling her woman’s opening. Each time Tess’s hips rose trying to capture his thick digit and steer it inside her she was rewarded with a firm slap to her bottom as well as his scolding voice.

“Be still, Tess.”

Lying beside her, he slipped his arm beneath her cupping her entire vulva in one huge hand, firmly holding her steady as his other slippery fingers, teased at her bottom hole.

Tess squirmed, butterflies having a party in her belly as she tried to relax in his hand. Even as nervous as she was, honey leaked from her core as she tried to dance away from his invading finger.

“I hadn’t planned to spank you, but I will, babe,” he whispered, nibbling on her shoulder. “Relax into my hand honey,” he ordered.

Tess tried and failed, only succeeding after he peppered her bottom with twenty or so crisp smacks.

“Good girl,” Rory murmured when he felt the weight of her hips settle onto his hand. Adding another bit of oil, he ever so gently began teasing her bottom, seeking admittance. Nestling his middle finger firmly against her clit, he tapped it each time, like a gentle spanking, as he nudged farther and farther inside her bottom. His first knuckle was surrounded by her tight ring before Tess began squirming again.

“Do you need another spanking?” he asked, glad she couldn’t see his smile.

“No,” she replied softly, a pout in her voice.

“Then relax and behave. I plan on loving you as often and in as many ways as I want, Tess, so you may as well get used to it. I will never hurt you, babe, but you will always submit to me.”

Tess nodded. Sighing, she gave herself over to Rory.

The tapping began again and he removed his finger, added more oil and slid back inside of her to the hilt, past each knuckle until he could go no further. Pausing, he gave her time to adjust to the intrusion as he firmly held her, one hand under her, the other with his finger firmly implanted in her beautiful bottom. His enormous cock throbbed against her hip in time with the contractions of her rectum.

Rory closed his eyes and clenched his jaw. What he really wanted to do was replace his finger with his cock and plunge into the deep, dark opening, filling her with his cum as she pulsed and quivered around him. That, however, was not possible. It would take many nights of preparation before she would be able to accommodate him in that way. Nights he would enjoy immensely.

Forcing his mind back to the present, Rory slowly began gently retreating and plunging into Tess’s bottom while rubbing and tapping her clit. Her low moans reassured him that despite what she might say, she loved everything he was doing to her. Each time he felt her tense he would stop torturing her clit, holding his finger still inside her until she relaxed back into his hand before returning to his ultra-slow, methodical invasion. Finally, Tess became so frustrated her little feet began kicking the bed, her lips pleading for him to either stop or do something to release her.

Rory removed his finger, slipped his arm out from under her and stood. Quickly he went into the bathroom, washed his hands and returned. In seconds he’d bound her wrists together with a tie and Tess watched wide-eyed as he secured it to the headboard.

“Rory?”

“Shh, you’re fine, babe. Trust me?” he asked, leaning down to kiss her.

“Yes,” she answered breathlessly.

“Good girl,” he replied, patting her ass. Grasping her hips, he lifted them until Tess was on her knees, her head down. He slipped first one pillow, then another under her belly, adjusting her to his specifications. Picking up a relatively small butt plug that was much larger than her pacifier, but nowhere near as big as his cock, he lubed it thoroughly. Holding her cheeks apart, Rory slowly began working it into her tight passage which had returned to normal in the short time since he had penetrated it.

Tess squirmed and squealed, but Rory would not be deterred. He didn’t scold her in any way, but when she continued to wiggle, making this much harder than it needed to be, he set the plug aside and warmed her ass. When Tess was sniffling and compliant once again, he re-lubed the plug, gently but firmly pushing it deep within her bottom. The flange at the base, kept it from going too deep, but the wider section just before the flange was harder for her to take. Regardless, he had his way and patting her red ass he admired the picture she presented.

Kneeling behind her, he forced her knees apart, giving him plenty of room to fit between them. Harder than he could ever remember being, he nonetheless took the time to again massage Tess in a firm way until she stopped quivering. His long arms had no problem reaching under her to take her breasts in a firm grip, plucking the tender nipples until they were hard little nubs. Sliding lower he cupped her snuggly, gathering her sweet tribute and rubbing her stiff little clit until she moaned in appreciation. Seconds from completion, he stopped and Tess exploded in outrage.

“I am going to kill you, Rory O’Malley, if you do not give me some relief,” she sobbed.

“You’re hardly in a position to be issuing demands, babe,” he said smiling as he covered his cock with lube. Even though she was dripping, he wanted to be sure she experienced no real pain when he entered her.

“Eventually, you will have to untie me. After that, I will be free to give myself pleasure any time I choose,” she informed him sarcastically.

“And how will you do that?” he inquired not yet revealing his amusement.

“I do not know, but I will manage it. Perhaps I will use that little vibrating egg you have.”

“Perhaps if you do, you will get your little fanny spanked like a very naughty, little girl,” Rory shot back. Positioning himself at the entrance to her pussy, Rory eased slightly into her, smothering his groan.

Tess wavered, angry that he had brought her so close so many times and aching for him to fill her wanting body.