Faint Heart Never Won Fair Lady

"Good fit. Now sit and go through the forms. When you're done, stand and present for my return."

He inspected the chastity device as soon as she left. His head was free and some of the underside of his shaft was accessible. But the snug band around his scrotum was a single handcuff, holding him high against the underside of the tube. And it was locked; there was no sign of the key. He sighed, read, signed and dated the forms, then left the clipboard on the arm of the chair and reassumed the position. Helen soon returned and quickly glanced through the papers. He stood still, waiting, and feeling faintly foolish.

"Good. Keep your hands where they are, and follow me."

Walking as naturally as he could, Jack followed Helen out of the parlor and through a doorway under the hallway stairs. His eyes quickly scanned the basement as he descended to it, taking in the bare brick walls, the track lighting, the steel and leather furniture, and the massive, wide, floor-to-ceiling steel closet against the far wall.

"Open the doors to the closet."

Jack walked to it, opened the doors and immediately his heart rate punched up a notch and he felt an adrenaline surge. The inside of the doors were lined with implements for beating, whipping, pinching and pulling. A selection of steel bars in varying lengths was arranged along the back, along with cuffs, shackles, chains, and lengths of rope. Discretely labeled drawers presumably contained smaller items; he had no idea what they might be, or what might be used on his body.

"Bring me a larger collar. One with two chains attached."

He scanned the equipment, selected a black leather collar for himself with two silver chains attached to a D-ring in the middle. There were small, rubber-tipped clamps on the ends of the chains. He knew where they would go. He turned with his collar in his hand, looked for Helen. She was standing in a pool of light beside a declining bench that was mounted on a steel frame. The top was shaped like a horizontal hourglass, and covered in dull black leather. He approached, wide-eyed, already picturing himself on it.

"Lower your arms and drop to one knee."

He held himself still as she buckled the collar behind him. The chains hung loosely, swinging against his nipples. The clamps bumped gently against his abdomen.

As he took in the snug feel and sensation of the collar, realizing its presence around his neck, something of his identity slipped away. It was a relief. And to be relieved was a relief. It meant he truly wanted this. He was exhilarated.

"Stand up and align yourself with the bench."

He stood at the bench end, taking in its contours.

"You will see the vertical section facing you consists of an arch. This is to afford access to your genitals. You will also see that it is slanted towards you. This is to force your buttocks outward. Mount the bench. Kneel on the raised pads and place your thighs against the vertical."

His uncertainty returned. This would be the most willful act of submission he had ever performed. It was a threshold that part of him did not want to cross because he knew, once he'd gone past it, there could be no turning back. The door to his former life would be gone. He could never, ever, forget that he had done this. Helen waited silently. They both knew he had two choices; he could balk, or he could obey.

He understood, then, what Helen was waiting for. Whatever he decided to do, Helen would call Christine. The thought of Christine hearing he had kept his promise propelled him on; his mind stepped forward over the line, and to Christine's waiting pleasure.

His body was tense and he felt awkward, but he managed to clamber up and get his knees and thighs in position with some grace.

"Well done, Jack." Helen's voice was warm and soft. It was more than a bench he had just climbed; it was his own personal Mount Everest and she knew it. Her tone and simple praise let him know she was pleased for him.

Then it was back to business.

"Now, bend forward and lower yourself to the decline."

He lowered himself down slowly to the bench top, feeling the supple leather caress his skin and the hard press of the chains and clamps where they pooled beneath his chest. He carefully drew them out to either side of the bench and let them fall.

"Lower your arms to the frame and hold your wrists ready at the straps. Lay your head against the bench. Face the wall."

As Helen strapped down his wrists, thighs and calves he laid his cheek against the smooth leather and tried to relax. He was totally exposed, yet comfortable. His bent legs were splayed open; the curve of the bench end pushed against him and held him ass out. The decline held his ass up. The final strap was a wide leather belt that Helen passed beneath the bench top and buckled over a pad that covered his kidney area. He was now totally immobilized. He was aware of a growing discomfort as his cock began to swell in its constricting, bent prison. He was conscious of his balls in open space, held up against his hurting cock.

"Your Mistress will be here shortly. Lie patiently, and do not turn your head."

Helen left. He waited, nerves coming undone. Were there cameras? He didn't dare to try to look around. He attempted to control his breathing, slow his pounding heart. The 'phone call would be brief, he knew, but it would be a while before she arrived.

*******

The slow step on the stair broke him out in a sweat. Footsteps walked slowly past him. There were faint sounds at the closet, and then he heard the sound of steel drawers opening and closing. Someone approached him from behind, moved to the side of him. Christine? His heart pounded as her face came into view. She crouched beside his head. Her beautiful, serious, deep hazel eyes looked fully into his. He gasped at the light shimmering on her blonde hair. It flowed in a radiant mantle down around her latex covered shoulders. She was totally sheathed in a shiny, black, latex catsuit; from her neck, to her wrists, to her ankles, as far as he could see. He could not tell from her expression how she was going to be with him. She looked pleased to see him, but so different.

When she finally spoke, her voice was mellow, soft. She invited him into the game he so much wanted to play.

"You're not wearing your clamps. It would please Mistress to apply them to you. You would like that, wouldn't you?"

He licked his lips, swallowed hard. "Yes, if it pleases Mistress."

Her eyes glowed and she smiled.

She reached below the bench to a dangling clamp and deftly applied it to his nearest nipple. The tight pinch immediately focused his attention. As the initial pinch wore off, a growing ache began to gnaw at him. He kept still as she moved around the head of the bench to his other side, and kept his face averted as the same torment was applied to his other nipple. She walked to somewhere behind him.

"You look nice; very nicely positioned. And well trussed too." She moved to the side of him. "But what's this? I see a little dew here, I think."

He felt her finger slide his precum over his head. Her gentle fingering caused him to swell more. It hurt him. He stared at the wall as she toyed with him. The impropriety was delicious.

Her tone hardened. "Just as I thought; you need milking. How disappointing. I suppose you think it's flattering, that I should be impressed? Well I'm not, not at all. What would impress me would be for you to take a beating. In silence. Do you want to impress me?"

"Yes, Mistress, I do."

"Very well. Let's see how you do with the tawse, shall we?"

She must have already selected it from the closet, he decided, because the punishment began immediately. Three long, heavy, leather fingers struck across both his buttocks on the first stroke, quite lightly, just to place her aim. Then she gave him six strokes. She started gently, but each lash was firmer than the last until he gasped with the force and follow-through of the final strike. After the first six, Christine soothed each cheek with a circular, stroking caress of her palm until he relaxed. And then she resumed.

She worked the tawse powerfully and rhythmically around the sweet spot, just above, below, and over the center of his buttocks. The loud slaps exploded in his eardrums and carried through the air of the open room. With every stroke the leather fingers sank into his flesh with a heavy slap. She allowed each stroke to subside to a warm glow before applying the next. Jack's breathing was ragged, but he made no other sound besides an occasional involuntary grunt as he jolted from the force. To keep his skin relaxed and fresh, Christine palmed his cheeks again.

"That was a sufficient warm up, I think. Now, Mistress is going to cane you."

There was no respite; she began to cane him immediately. But it was a substantial cane and she applied it lightly at first. On delivery, she held the cane against his cheeks before applying the next lash. The fifth stroke brought his head up and off the bench with a gasp and a start.

Each lash began with his hearing registering the oncoming blow. The cane hummed through the air and the sound of its strike against his outthrust cheeks was an assault in itself. He closed his eyes tightly as the cane landed. The blow's energy traveled through him to his abdomen, where it was finally absorbed by the leather pressed against him. The height of the sting followed a moment later, then fell to a resonant ember that spread through his skin and lower body.

The onslaught was powerful; every lash was a demand for vocal relief. There was the occasional gasp or grunt, but he did not cry out. He pressed his brow against the bench and his lips against each other, striving to maintain control of himself.

He had begun to grow used to the phases of the lash; the awful pause, the ominous hum, the bite, the sting, and the heat, when she suddenly broke all his expectations and lightly lashed both his inner thighs and the tender strips of flesh where his thighs met his cheeks. She worked him over quickly with the tip of the cane as he struggled anew to keep from voicing his agony.

From that point on he had no idea if the next stroke would be hard or light, or where it would fall. He was fully submersed in pain. Working quickly, then slowly, then fast again, she caned his thighs, his calves, and again and again on his buttocks until his cheeks were covered in stripes and welts.

She slowed, eventually, until he heard the cane drop and felt her fingers press against his burning skin, drawing the heat from him. She rewarded his stamina by mercifully rubbing and kneading his flesh to ease him. He loved that she touched him so, loved even more to feel her excited breathing falling softly on his burning flesh.

"You're doing very well," she told him. "But you need more attention here, perhaps."

She pressed a finger at his exposed anal rim and he tensed involuntarily. A new consciousness arose within him. Almost in panic, he thought of the safeword and his list of unacceptable 'play'. But he'd said he trusted her. He'd said she could take what she wanted. He dreaded her entry, but he didn't want to stop her.

"It would please Mistress for you to be compliant," she said, softly.

It was the encouragement he needed. He exhaled and relaxed as much as he could as she pressed again at his entrance.

"Good boy."

She withdrew her finger when she felt him give to her. Evidently a demonstration of his intent was all she required for the moment. As she spoke, she moved to the farside of the bench where Jack was facing the wall.

"You could use something to help you focus your attention. A little release, although you may learn from this that not all release is pleasurable. Tell me if it is not so."

She bent and yanked one clamp from his nipple by its chain. He yelped with the shock and then felt the agony of blood returning to his starved tissue.

"Well?"

"It hurts, Mistress," he gasped.

"How does it hurt?" she asked, as she moved to the other side of the bench.

"It hurts hard, Mistress."

"Then you have learnt a valuable lesson; one that should be reinforced."

So saying, she sharply pulled off the second clamp. He felt the pain flooding his second nipple as the agony of the first subsided to an insistent, throbbing ache. He heard her footsteps retreat to the back of him once more.

He realized what she had just taught him. All his carefully controlled life he had known that bad choices would expose him to the hurt, the blows and the buffeting of life. But in bondage to her, all choices were hers, not his, and in that was his emancipation. In this bondage he was unleashed, he was free. Release from this bondage could hurt.

As the throbbing pain suffused his breasts he heard the snap of latex and a faint click, and then he felt her gloved finger smearing soft and silky fluid around his rim. His body was for her, he told himself, trying to achieve quiescence as she attended to him.

She did not relieve him of his fear immediately. She savored it a while. She pressed on the spot between his ass and balls and massaged him in small, firm circles until he was stimulated and his sphincter began to twitch. Then she pushed a finger into him, lubricating him gently but insistently. To his embarrassment, his sphincter tightened on her.

"Open to Mistress. Just once more."

She waited until he could release. She pressed another finger to his rim while she withdrew the first, and then she crossed both fingers and entered him in one deliberate, wedge-driving, fluid motion. She began to fuck him gently, sensually, until his pleasure built and he ached to gratify her, to give himself to her, to show her his thanks for her merciful release. He began to push against her, as much as his straps would allow.

"Oh yes! There's a good, fucking, boy! That pleases Mistress very much. Let's open you right up now, shall we?"

She pushed something firm into him.

"Squeeze now; draw it in for Mistress. Then relax, and let it fill you."

He clenched and felt it ascend easily until a nub rested against his prostate. Externally, a part of the probe pressed against him between his ass and balls, and he could feel a part of it pressing outside his rim.

For a moment, he had a terrible feeling he was going to wet himself, and he felt uncomfortable with the hard object inside him, but he did as she told him and concentrated on breathing and making himself relax. The strange sensations quieted and eventually he simply felt full. She stroked and massaged his hot buttocks while he adjusted to the insertion.

"You are making Mistress very happy. So hot and red, and you hold your little handle out so well. Mistress is proud of you. Would you like Mistress to use your little handle?"

He wasn't sure what it meant but he trusted her. "Yes, if it pleases Mistress to use it."

"Very well then."

She took the handle of the probe and subtly moved it inside him. His whole lower body was in a turbulence of pain and heat; and then he felt the first thrumming wave of pleasure from his prostate. His breathing deepened as she continued to massage him, and the wave built. As she massaged his prostate through his rectal wall, the pleasure intensified deep within him; and then another wave began to grow at the root of his cock.

Bound and compliant to the sensations she was causing him, he felt vibrant warmth spreading through his trapped cock and balls. For all the restraint he had exercised through his strapping and caning, he couldn't suppress the deep, shuddering moan that exploded from within him as his body succumbed to his slowly building orgasm.

She took him further. She stimulated him relentlessly, creating a building ebb and tide of pleasure through his body. As he gave himself up to her, the waves rocked and rolled him, carried him up and beyond all his known pleasures to heights he had not glimpsed before.

He had never felt been forced to orgasm, had never conceived of it. Stepping forward through the blinding ecstasy of what was being done to him, the analytical self that protected him in his everyday life assessed the situation and concluded Jack was succumbing to an inescapable violation.

It was not violation because he could not stop the forced pleasure; he still had his safeword. It was not inescapable because she would ignore his safeword; he knew she would not, this was not edge play.

Jack's remaining reasoning concluded the violation to which he was succumbing was inescapable because it was an act of his own making, an act for which no safeword exists. Jack was approaching the abandonment of self. Emerging from the overload of his submission, Jack's total surrender enticed him, beckoned him and invited him into its black folds. He almost could not conceive the concept of a safeword now. Jack was far, far, gone.

The last standing guardian of his mind stayed with him, but it needed Christine's help. Noticing the slackness in his body and his shallow breathing, Christine quickly stepped to Jack's face and saw the need in his vacant eyes. The stroking of her hand on his cheek pulled him back.

"Jack, do you want to stop?" He shook his head slowly.

"Are you sure?" He nodded.

"You like Mistress milking you, don't you?"

If he answered that one, Christine decided, he was still in the game. She smiled as he blinked away the beckoning darkness, smiled at her, and whispered, "Yes."

"Then thank Mistress," she told him, softly.

"Mistress, thank you for milking me."

"My pleasure; but you milk yourself now. Do as Mistress tells you. Squeeze on your massager and work it inside yourself."

He summoned the will to obey her. He found he could continue the stimulation by slowly contracting and relaxing his sphincter. As he concentrated on his breathing, the waves pulsed and grew anew. He maintained a steady rhythm, urged on by Christine's watching and sweet murmuring.

"Do it for Mistress."

"Good boy. Work it. Show Mistress."

"Make milk for Mistress."

As he began to spasm involuntarily, the probe stimulated him without his conscious effort. He could not stop; he was helpless. As the spasms came more rapidly, they became deeper. He was drenched in sweat, groaning and helpless, caught up by the waves within him. In his peripheral vision, he was vaguely aware of her reaching below the bench.

"Mistress is waiting now. Milk yourself into the cup for Mistress."

The pulsing waves mounted within him, driving him to a pinnacle of pleasure and beyond. His cried out as his whole body shook and his major muscles went into uncontrollable convulsions.

Suddenly, without erection and with no further urging, he released his pre-cum. It flowed from him, copiously, freely and steadily. He heard it draining into a plastic receptacle beneath him.

"Good boy! Mistress is very pleased. Lie still and relax now."

The probe still pulsed with his involuntary contractions but she allowed him no more orgasm, instead gently easing it from his back passage. He groaned with confusion and intense, total, bodily relief.

He heard a faint click and felt his imprisonment being removed from him. His balls dropped down and his cock hung freely at last. He was flaccid. He wasn't sure now if he could achieve an erection or not. The answer came shortly afterwards, when she showed him what she was going to do with his fluid.

She came into view, and stroked his perspiration-soaked hair gently, bringing her face close to his. She gazed into his eyes, murmuring softly to him as he slowly resurfaced.

"You pleased Mistress so much you deserve to be rewarded. Mistress will allow you to suckle her."

She undid the zippers over her breasts, and pulled them from the catsuit. They stood free, apart, and in stark contrast to the black latex. He watched as she pulled on her nipples until they stood upright. She leaned low over the bench, placing a breast close to his face, took the cup, and poured some of the clear, viscous liquid over her breast. As it flowed to her nipple, she held herself to his mouth.