Spring Plaza Hotel

Jake rubbed her ass again, then retrieved the belt he'd strategically had Anna leave on the bed. He folded it in half and cracked it, watching as her head snapped back to look at him. His eyes twinkled as he grinned at her, watching her cringe and shudder. He drew the folded belt back and delivered a well-aimed smack to her ass, listening as Anna yelped loudly, her back arching to receive the impact. "Forty-one, thank you Sir." He delivered the last nine smacks to her ass and the backs of her thighs in this way.

Once he finally heard her cry out, "Fifty, thank you, Sir!" he tossed the belt away into the corner, and said, "Well done, now relax." Anna collapsed onto the bed, her ass stinging, tears welling up in her eyes. She was proud of herself for enduring the pain that Jake had delivered, though, so the tears were a mix of pain and joy. Jake had walked away into the bathroom, and returned, sitting down on the bed next to her. She felt him begin to rub her ass gently, cooing softly to her, "Good, girl, it's all done," and other soothing words. She realized that he was rubbing lotion into her ass and down the backs of her thighs, which helped her cool down and relax.

After several minutes of rubbing, she began to feel a longing to continue. She looked back at Jake and smiled over her shoulder, then rolled into him, her back pressed to his chest, her ass to his waist. Jake held her for a moment, then stood up, guiding her to stand as well. He took his place in his chair once more, pulling her toward him to sit on his lap. His legs were spread, and she landed with her ass pressed against his groin, her legs closed. Jake and Anna had previously discussed her interested in bondage, but how she had never tried it before. Wanting to take it slow at first, Jake took her wrists and placed her hands on the top of the armrests of the chair. "Keep your hands right here until I tell you to move them, understand?"

"Yes, Sir," she purred.

"Good. Now, I'm just going to explore your body with my hands as we sit here. I won't be touching anything that is covered by clothing." His hands slid up her arms to her shoulders, then back, caressing her shoulders, her arms, her wrists, her inner arms, and back. He slid his hands up and down her back, and her sides, then her arms again. He watched her carefully, and once she began to arch her back slightly, he slid his hands around from the small over back to her stomach, rubbing it up and down. Then his hands slid down to the tops of her thighs, between the garter and her stockings. He explored her thighs gently, sliding from the tops to the sides, then back up her back, and around her waist once more.

Jake then slid his fingers between her thighs, pulling them apart so that her knees crossed his, and he held them separated with his legs. He continued to explore her inner thighs with his fingers and palms, teasingly and seductively. He then slid his hands back up her arms and to the top of her chest, above her breasts. He then pushed her shoulders gently, guiding her to stand, turn, and straddle his waist. He placed her hands on the back of the chair, saying, "This is their new spot. No moving unless I say."

"Yes, Sir."

He continued to explore her in this new position, continuing to caress her upper chest, then her back, and her outer thighs. He pulled her into him close, so that her breasts were pressed against his chest, his hands resting on the small of her back. He pressed his lips to her left ear and whispered, "I said nothing covered by clothing, correct?"

"Yes, Sir," she moaned.

He left his right hand on the small of her back, sliding the left up and to the clasp of her bra, deftly unhooking it. He then guided her to turn around again, pulling the bra off and tossing it aside as she turned. He then pushed her forward to her knees, kneeling with her back to the chair. He stood and went to the leather bag she had brought, opening it and finding one of the silk scarfs. He returned, sat behind her, and brought her wrists over and slightly behind her head. "I'm going to tie these in place now. You're to leave your arms and wrists here until instructed otherwise."

"Yes, Sir."

He had crossed her wrists so that both palms were facing toward her front, the wrists placed together. He then began to wrap them both together several times with the silk scarf. He then crossed the ends of the tie, wrapping it between her wrists and around the previous wraps over itself. Then, he tied it tightly. Even absent his command, she would have found it difficult to move her arms to any other position with the way her wrists were bound, able to bend with only great exertion.

Jake placed his hands under her arms and lifted her back to his lap, with her legs separated by his as before. His hands slid down from her arms to her chest, and he slowly began circling her breasts with his fingertips and palms. The circles became spirals, moving closer and closer to her nipples, but never quite reaching them. He then trailed his fingertips down her sides, then in to her sternum, and his palms up to cup her breasts in his hands. His thumbs and forefingers began teasing the flesh to the sides of each nipple in a gentle pinching motion, drawing closer and closer to them, but again not quite touching. Finally, his fingers and thumbs closed on her nipples, which had grown hard and perky from his teasing. He pinched lightly, pulling away, then releasing, over and over again.

Anna began to moan and squirm from his touch. As she did so, he pinched harder, holding on for longer before releasing. He began rolling her nipples between his fingers as he pulled and pinched, listening to her breathing grow faster. He reached over to the table and the ice bucket and pulled out an ice cube. Holding it between his finger and thumb in his right hand, he slid the ice up from her breast to hold it directly against her nipple, continuing to tease the other. After several moments, he switched the ice from her left nipple to her right. He continued this back and forth, icing then teasing, feeling her writhe in his lap.

After the ice cube had fully melted, and Anna's breathing and grinding in his lap had intensified significantly, Jake slid his hands down her sides and under her ass, then guided her to stand up. He admired her briefly, the way the thong perfectly complemented her tight, round ass, then he hooked his fingers into the waistband and slid it to the floor. "Stay there," he ordered, and went to the leather bag of toys, finding the locking cuffs. He returned with the cuffs and a handful of locks. Sitting back down behind her, he slid the thigh cuffs into place, teasing her inner thighs with his fingertips as he did so, and then locked them in place as well. He then slid his hands down her legs to her ankles, where he locked the ankle cuffs in place.

"Now, kneel," he said. She carefully dropped to her knees, nearly losing her balance without the aid of her arms. Jake then untied the silk scarf from her wrists, but quickly replaced it with the wrist cuffs, which he also locked in place. He rubbed her shoulders and arms for a moment, soothing them from their awkward positioning, then slid his fingers down her arms to her wrists, which he grabbed firmly and guided down to her thighs. He then attached locks to the d-rings of the wrist and thigh cuffs, securing her wrists to the outsides of her thighs. The thigh cuffs were tight enough that even when she pulled, she could not get them to slide around her thigh. She realized this when Jake grabbed her wrists and tugged, testing their security, laughing as she groaned in frustration.

Next, Jake put his hands under her arms and helped her to stand, guiding her with him back into his chair. His hands found his way back to her breasts, which he fondled for a few moments before sliding his hands down her stomach to her waist, then the tops of her thighs. His fingers teased the skin of her thighs at the edge of the thigh cuffs, tracing back and forth. His fingers then began to slide up her inner thigh, away from the cuffs, closer to her newly shaved and exposed sex. He paused with just millimeters to spare, resting his palms against her thighs, sliding both hands around her legs, his fingers pressing firmly into her inner thighs. The edges of his fingers were menacingly close to her pussy, and she had difficulty controlling herself, aching to feel his touch.

Jake slid his hands up her inner thigh gradually, so that the edges of his fingers just barely grazed the shaved flesh of her pussy. He then continued sliding them around her leg, reaching deep between her inner thighs, then rotating back, his hands teasing her menacingly. He then slid his hands up, pressing his palms to her hipbones, stroking his fingers into the creases between her legs and stomach. At first, his fingers merely brushed the creases, but then he began to increase the pressure, pulling and spreading her lower lips apart. Anna writhed in his lap, pulling against her restraints on her thighs, desire building from the tease.

Jake then reached down further, softly and gently rubbing his fingertips against her outer lips, up and down. He continued to stroke softly, slowly, then started to increase the pressure with each stroke. Then he laid his whole hand against her pelvis, the entire lengths of his fingers rubbing her lips, his hands stroking in unison up and down. After tormenting her like this for what seemed an eternity, he shifted his right hand, his index finger separating the soft, excited lips of her pussy. He dabbed her juices, wetting his finger as he began to slide it up and down between the folds of her sex. Then his middle finger joined his index finger in the tease. Jake curled his fingers, entering her slightly, then withdrawing, no deeper than the first knuckles on his fingers, in and out, slowly, agonizingly.

Anna was moaning deeply at this point, writhing about on his lap, desperately craving deeper penetration. Jake slid his left hand up her back and grabbed a large fistful of hair from the back of her head. Keeping his fingers inside her unmoving, he pulled her hair slowly yet forcefully, bringing her ear back to his lips as she looked to the ceiling. "Do you really think I would let you cum before me?" he whispered, seductively and menacingly, his hot breath tantalizing her ear and neck.

Anna could tell that the answer was obvious, but responded anyway, "No, Sir."

Jake laughed deeply, flicking her earlobe with his tongue, sucking it into his mouth for a moment, giving it a quick nibble with his lips. Then he pushed her to stand up, and removed the locks that kept her wrists pinned to her thighs, but left the cuffs in place. Jake walked over to the bed, and spoke as he walked, "I want a massage."

Anna was still a bit dazed from the torturous tease, and watched Jake as he lay down on his stomach on the bed. At first, his head faced away from her, and she continued to watch, still recovering, but she snapped out of her daze when he turned his face and looked at her, his gaze penetrating her. She jumped then, remembering a bottle of massage oil that was in the leather bag. She returned with it, poured some of the oil into her hands, and began to coat Jake's back with it.

She started rubbing with light pressure, then pushed harder, feeling tension begin to melt away from Jake's back. She pressed her thumbs into his shoulders and mid-back, her palms into his lower back. Jake moaned occasionally, letting her know she was doing well. "Now, my legs," he said, and she slid her hands down his back, rubbing the backs of his thighs, then his calves. Standing, her left hip was pressed to his right as she slid back up to the backs of his thighs, and he began to roll. He reached out with his right hand and grabbed her left thigh, between her legs as he rolled onto his back. "Continue with my legs," he urged.

She poured a bit more oil into her hands, then continued rubbing his upper thighs. As she rubbed, he caressed and rubbed her inner thigh, moaning occasionally. Between the moans, his grip on her thigh, and the bulge in his boxers, she could tell he was enjoying this. His commands made her feel wanted and needed, and she relished in the service to him.

"Now, take off my boxers," he moaned deeply. She turned to look him in the eyes and smiled, then hooked her thumbs into the waistband of his boxers, pulling them down and freeing his engorged cock. She started at it, her heart pounding in her chest. "Stroke it," he commanded, "slowly." Her hands still slick with oil, she grabbed the base of his member and began to stroke, with long, slow movements. Jake moaned, caressing and squeezing her thigh as she stroked his cock. "A bit faster now," he moaned, and she increased her speed, feeling his fingers grip her thigh, then his hand slide up to her ass. "Faster," he cooed, squeezing her firm buttocks tightly. She complied, gripping his shaft firmer and pumping him faster.

His ankles began to shift and slide against the bed, and his back arched, feeling his excitement grow. He slid toward the middle of the bed and pulled Anna by her inner thigh, guiding her to climb up and kneel on the bed as she continued stroking him. He squeezed her thigh, his breath growing faster and shallower, commanding, "Faster!" At this, Anna increased her speed dramatically, working his cock with her right hand, rubbing his chest with her left, and leaning her hips into his hand. Jake's hand slid up to her ass, which he started to rub and squeeze, digging his fingers in firmly. "Oh, god," he moaned, as waves of pleasure began to overtake him.

Anna watched as his legs began to convulse, stiffening rhythmically, showing that his body was ready to orgasm. He continued to breathe fast, sweat beading up on his forehead, urging her to continue with his moans and grip on her ass. She maintained her rhythm, feeling his cock start to throb in her hand, until it finally exploded onto his stomach, as he let out a load, deep groan of ecstasy.

Jake moaned for a moment, recovering and cooling down, then ordered, "Clean it up." She bent to retrieve the towel from the floor, but he grabbed her waist before she could leave the bed. "No, with your tongue," he said, his eyes sparkling mischievously. At first, her mouth dropped agape, but then she saw that he wasn't going to relent, so she slowly leant down and lapped up his cum, being sure to clean it completely and swallow it all. Despite feelings of humiliation, her pussy reignited with heat and yearning, due to the degrading act.

After he recovered, Jake pulled Anna down onto the bed on her stomach, pinning her down. He unhooked the garter from her stockings and removed it, tossing it to the side. Then he reattached the locks to her wrists and thighs, binding them together once more. Then he retrieved the blindfold and the gag from the leather bag. He walked to the edge of the bed and pulled her ankles, then her waist, guiding her feet to the floor while her chest remained in the bed. Grabbing her hair, he pulled her head back and slid the blindfold into place.

Jake stood up straight behind her and used his toes to gently spread her feet wide. He ran his hands down her back, over her ass, and down her thighs. His hands then crept up her inner thighs, teasing and tantalizing them. He pressed the back of his right hand to her pussy, feeling her juices coat his hand as he rubbed softly at first, then a harder, listening to Anna's purrs of delight. He took the dildo gag and ran it across her pussy, coating it with her juices. Then he leaned forward onto the bed again and held it under her nose. "Smell your sex? Now you can taste it," he moaned, sliding the insert into her mouth and buckling the straps behind her head. Anna wheezed as she started to breathe through her nose, her body shuddering and writhing in mixed pleasure and humiliation.

Jake glided back to the toy bag, removing the spreader bar, a small plug, and some lube. Strolling back behind Anna, he tossed the plug and lube onto the bed next to her, then knelt down and attached the spreader bar to her ankle cuffs, making sure to set the bar to its widest setting. Sliding his hands up her calves and inner thighs, he teased her pussy with his fingertips, coating them in her juices. He then dragged her moisture up her pussy to her tight ass, circling her entrance. He continued to tease her ass with her juices, pressing his fingertip in and around, until she was squealing into the gag and bouncing from foot to foot, her exposed ass waving in the air.

Once he could tell that she was prepped and truly ready, he grabbed the plug, rubbed some lube onto it, and pressed the tip to her ass. Spreading her with one hand, he slowly plunged the tip into her hole, watching as her back arched, listening as she moaned into the gag. He withdrew it, then pushed it in a bit deeper, then back out, back and forth, slowly exploring her deeper and deeper. Finally, he pushed it all the way in, watching as her ass sucked it into place, the flange pressed tightly against her. "Don't let it fall out," he commanded, listening as she moaned agreement into the gag.

Back at the toy bag, he withdrew the flogger. It had an eight inch, leather wrapped handle with a huge array of black deerskin tails. Resuming his place behind Anna, Jake drew the points of the tails from her knees up the back of her right thigh, over her ass, up her back, then back down to the back of her left knee. He repeated this circuit several times, back and forth, watching the tails tickle and tease Anna's flesh. Then, stepping to her right side, he drew the flogger back, circling away from her ass, slowly, then back, slowly, letting the tails just graze the flesh of her ass as they hung down from the handle. He repeated this motion several times for each ass cheek, gradually building speed, but only letting the tails kiss her cheeks.

Jake's strokes began to gain speed, but still only while the tails hung down. He then stepped back behind Anna, flicking the tails up and against the flesh of her ass with light, playful swats. After watching her sway and bounce, seeing that she had warm up, he began occasionally inserting a more powerful stroke, followed by two light strokes, alternating cheeks with each stroke. He changed the his swatting pattern then, beginning to guide the flogger side to side, striking the sides of her ass, maintaining the rhythm of one strong stroke followed by two light strokes. Hearing Anna moan and watching her writhe about on the bed, he changed the rhythm again, to two hard strokes followed by one light.

Hearing her moaning grow louder, Jake changed the pattern once more to a figure eight, striking alternating ass cheeks with two hard strokes followed by two light strokes. He beamed as he watched her squirm, heard hear moan and squeal, and saw her ass glow red from the beating. Finally, he stopped and said, "Ten more." He heard Anna moan assent, and proceeded to deliver ten hard, deliberate strokes to her ass cheeks, five on each.

Jake tossed the flogger onto his chair, and rubbed her ass with his hand, marveling at the heat that had built up. He rubbed and caressed her ass, occasionally slipping his fingers between her thighs to tease her. After she had recovered from the flogging a bit, he slid his hands down to the spreader bar to unhook it from her left ankle, turned her around, and helped her lie down on the bed. He guided her to the center of the bed and replaced the spreader, adoring her lovely body.

Back at the toy bag, he withdrew the crop, nipple clamps, and a small plastic vibrator. The crop had a wide, supple, leather keeper. The clamps were clover style and all metal. He slid back to the side of the bed, tossing the clamps and vibe next to Anna's shoulder, letting her imagine what might have landed there. Then he touched the crop to her ankle, and slid the tip up her leg slowly and softly, then up her waist and stomach, to her breasts. He rubbed the keeper back and forth between her breasts, slowly, circling around her nipples as it glided by. He pushed the end of the crop into the bottom of each breast in turn, slowly exploring her and letting her feel the implement.