(This chapter is a flash-back to that first session described in the previous chapter)

He’d never brought her back to this secluded spot and that he finally had both excited and scared her.

Finally arriving, he pulled up to the curb but didn’t get out.

“Beautiful view, isn’t it?”

The last time she had barely noticed the view, more focused on what was being done to her and wanting to please her lover.

“Yes, it really is. I didn’t really notice last time.”

He chuckled, “Understandable.”

She was dying to ask him why he had returned to this spot but held her tongue.

At last he spoke. “This weekend is going to be very hard. On both of us.”

She knew her punishment was going to be hard on her but hadn’t thought much beyond that. Of course, she realized, it would be hard on her Master too. She knew he loved her, hopefully just as much as she loved him. Torture for sexual arousal was one thing, the same acts committed because she had failed in her duties, were something else.

“Yes, Master. I am sorry that I have made you have to punish me.”

“It does get tiring...”

She wanted to cry.

“I just wanted to tell you that no matter what happens tonight and over the next couple of days, I still love and appreciate you.

“Since there will be others watching I will be saying and doing some very cruel things to you. I know you’ll take it like the trouper you are, and make me proud.”

“Yes, Sir. I’m your good girl and want the world to see it.”

“Do you know we’re here? On this date?”

“This is where you made me the happiest woman on the planet... but it’s not our anniversary or either of our birthdays...”

“It is a special date though I’m not surprised it doesn’t stand out still considering all we’ve done together.”

She looked at him quizzically but couldn’t recall anything about the date.

“Tonight is the fourth anniversary of the first time I tied you up and fucked you in all three of your holes. The night I decided to do everything in my power to turn you into my slave and keep you forever.”

She was touched deeply by his romantic gesture and that he would remember it.

She had never forgotten the event though she had been used by her Master in all three of her holes so often that its date had long since been lost to her. But it was the first time she’d been fucked in the ass and that memory was a source of masturbatory arousal many times since.

When he told her, “Tonight I’m going to tie you up.” it was merely a statement of fact. He had already steered her towards submission and it was another layer in their already and always exciting sex life.

Once she was spread-eagled he sat on her chest and fed his erection into her mouth, each stroke going a little deeper until at last her nose was buried in his well-trimmed pubic hair.

He had already trained her to take it without gagging and, when he kept it there until her lungs burned, begging for air, not to protest.

It was when he was choking her like this that he announced, “I’m going to cum in all three of your holes tonight too.”

Focused on the wonderful organ she was servicing she hadn’t really paid attention to the declarative nature of his statement.

She had been asked by past lovers if she was into anal sex but she had always just said she wasn’t, even though she’d never actually tried it. Every time it was respected and that entry remained ‘unsullied.’

But he wasn’t asking. And if she had been able to think about it as she struggled to swallow the copious amount of his cum that he was shooting into her mouth right then, she would have just accepted it.

Climbing off of her he lay next to her and used his fingers to gather the few drips of semen that had escaped and fed them into her eager mouth.

He cuddled against her tautly bound body and stroked her glowing skin.

Unsure of the protocol at that early stage, she just whispered, “Thank you... um... Sir...”

These words earned her a very passionate kiss, itself a surprising first. Many men had cum in her mouth but this was the first one who had ever kissed her afterwards. It filled her with a feeling of warmth and desire like nothing she’d ever felt before.

He did eventually break away, rise, go out, and return with a green bottle of Italian mineral water.

She hadn’t felt thirsty until that very moment when she saw him take a long swig of it. Suddenly she was very dry and when he didn’t offer her the bottle thought about saying something.

But a moment later was happy she hadn’t when he pinched the sides of her mouth open and let the water slowly drip out of his mouth into hers.

Even more than his thick seed, this felt exceptionally intimate. It marked her needs, though she didn’t realize it at the time, as secondary to his.

She swallowed it eagerly and when he took another swig, had her mouth already open, like a bird’s hungry chick, to receive his generous offering.

Every response from her, he observed, was perfect. He had opened the door to her submission but she had stepped into that dark chamber without hesitation.

Their thirst, at least for water, momentarily sated, he left the bed again for a moment and returned with a cloth bag that she recognized as his bag of clothespins.

Laying beside her he put the bag on her belly, took out a handful and methodically began to decorate her body with their pain.

Her nipples were still aroused and stiff and were an irresistible target for the first pair. She fought against the impulse and kept her eyes open as the burning pain radiated from her nipples to every part of her body. She focused on his face, his handsome and wonderfully masculine face. The half smile that showed how much he was enjoying her ever increasing pain. When he pulled out the skin at the crease between her abdomen and thigh and attached a pin to that especially delicate flesh it forced a sound somewhere between a moan and a groan and she watched him smile.

And it made her heart swell with joy.

From then on she made no effort to stifle the sounds of the ever-increasing pain. She didn’t emote or add any fake responses. She sensed that would be somehow ‘improper.’

By the time the bag was empty, rows of the biting wooden devices followed the most sensitive places on her body. Both her outer and inner labia and the sides of her clitoral hood. Every breath sent shivers of pain through her and they in turn sent even more. Tears at last rolled out the sides of her eyes as the agony overtook her completely.

Kneeling between her thighs where matching rows of clothespins could not avoid his contact she watched as he held up the last one. And though he asked, “Where do you think I’ve been saving this one for?” it was a rhetorical question. She knew, and he knew she knew.

But he seemed to be waiting for an answer so she took in as much breath as the painful clips allowed and gasped, “On my clit?”

“Good girl, ” he answered, smiling. And added, “Why don’t you ask me to put it there?”

She knew instinctively what he wanted from her and answered softly, “Can you put that on my clit...”

He ran his fingers over the ends of the ones on her labia and said, “I know you’re more polite than that. Ask me again. Nicely.”

“Please, Derek... will you please put that one on my clitoris?”

“That doesn’t sound very sincere. And I think you should use ’Sir’ when asking.”

Every breath was agony but paled beside her need to earn his approval. She took in a deep breath and for the first time slipped into her sub-space and pleaded, “Please, Sir... may I have the privilege of wearing your clothespin on my clit?”

She was good, he thought. She was either a very good actress or genuinely eager to suffer for him.

“Good girl, ” he told her, “Yes, you may.”

Despite the inescapable agony of the dozens of clothespins that had become a single solid presence in her consciousness, the brutal torment of that final clip pushed them all aside.

The tears flowed copiously and she was unable to form words either in her brain or with her lips, but she managed to smile her thanks.

Rising up on his knees she could see that his beautiful cock was once again completely erect.

“See what your suffering has done for me? I’m so hard it aches.”

The sight made her very happy but before she had a chance to even say so, he had sat back down and was pushing that organ through the phalanx of clothespins on her pussy lips and deep into her womb.

Disregarding, or maybe enjoying, her pain, he fucked through the clothespins in increasingly fast and increasingly hard thrusts. For the body he was fucking it was a new experience that it had never encountered before: soon the pleasure of the organ filling her and the pain of the clothespins became blended in a way that made them impossible to tell apart. It was the beginning of her path to becoming a total painslut though she had no idea at the time.

When he shifted his position to lay on top of her he came in contact with the dozens of other clothespins that decorated her. It gave him better leverage and his thrusts became even harder. Every one sending shooting pains across her skin that her brain told her she should hate. But her aching cunt overruled that, welcoming the increasing intensity.

She wished her limbs were free so that she could wrap them around him to increase the pain. And even as she had that thought she realized how perverse it was and that though made her womb ache even more. She was slipping into a quicksand of pain, humiliation, and wanton arousal and she loved it.

Lifting his body slightly he looked at her face and saw the bliss she was in. He knew then that he had met his match.

He relaxed and lowered all of his 105 kg weight onto hers, watching for a reaction. The added weight made breathing difficult but she didn’t protest. He watched intently as her face grew redder and redder as oxygen was denied her and she said nothing, made no effort to protest, until her eyes rolled back into her head and she slipped into unconsciousness.

Raising his body allowed her lungs to suck in a deep breath and to bring her back he slapped her, hard. First with his palm and then with the back of his hand. It took three blows before she came back and opened her eyes. It was the first time he ever did that but it would not be the last, by far.

“I-I—I’m... going... to... cum...” she gasped.

“Not yet, ” he told her in a voice that made her want to obey.

“Y-y...es... So... close...”

He found her throat with his fingers and squeezed it just enough to get her attention. “Not yet. Hold it back until I’m there.”

The thought of a simultaneous orgasm with this man was itself an act that made holding back harder.

“Your pain is exquisite, ” he whispered, “so beautiful...” He too was holding back his release, wanting to savor every wonderful moment of her surrender,

“thank you...” she answered, “I love that you think so.”

He could see how much she meant and with a half dozen extra hard thrusts, he shot his second load into her and ordered, “Cum. Now.”

Even with her limbs spread-eagled she still managed to spasm wildly as she released her orgasm, squirting and showering their limbs with her juices.

He lay on top of her for quite a while before finally rolling off and cuddling up next to her, resting his head against her right shoulder and nodded off.

His movements had moved nearly every one of the painful wooden clips and her body was wracked with waves of pain. She stifled herself, letting only a sigh escape her lips.

The reality of this wonderful lover who felt comfortable enough to rest and cuddle after so brutally hurting her was more than a little mind-blowing. She felt a contentment that she could not compare to any other time in her life.

When he finally stirred it was a whole new wave of pain from the clips as he untangled his limbs, rose, and left the bed.

‘Was this her fate? Was this her future?’ she wondered. ‘If it was, would that be that bad? Was the pleasure worth the cost in pain?’ Her mind raced through the possibilities but finally settled on that it was not the orgasms, as wonderful as they were, it was the post-coital bliss that made the rest worth it.

She felt him climb back on the bed and opened her eyes to see his face over his with his lips pursed. She opened her mouth, expecting more water but was startled when it was found to be some delicious liqueur.

She swirled it around her mouth, savoring the taste.

He held up a bottle whose expensive-looking label she could not read and took another swig that he fed to her like the first. It was delicious, slightly sweet with a smoky after-taste.

“I make it a policy to avoid alcohol or drugs when indulging in Sadomasochism. I don’t wanted to lessen any of the sensations. For either of us.

“But you’ve been an exceptionally good girl amd I thought you deserved a toast.”

She beamed, “Thank you... Sir. It was... amazing...”

He appreciated her adding the ’Sir’ but let it pass. Plenty of that training for later.

He seemed to be thinking and after what seemed like a long silence, she ventured, “Sir...?”

“Yes, little one?”

She had not forgotten his mention earlier of his intent to take her in all three holes and wanted somehow to let him know.

“If you still want... to do, um, anal... I’m ready.” His face turned dark and he leaned in close.

“Do you think it matters to me that you’re ‘ready?’ I’ll fuck your ass when I’m ready. And you’ll take it whether you’re ready or not.”

Chagrined she whispered, “i’m sorry, Sir. of course, Sir.”

His expression lightened slightly and he told her, “I’ve just been thinking of how I want you when I take your ass.”

He was tempted to just flip her over but that meant untying her and re-tying her. And then, thiinking of how much he’d enjoyed watching her expression as he fucked her pussy he had a moment of inspiration.

Untying the ropes that held her ankle cuffs, he bent her back on herself and attached the cuffs to the head of the bed next to her wrists.

The moving clothespins reminded her of their presence but she was glad she took yoga and found the position tolerable.

Looking up at him through her spread legs, she saw the look of Sadistic hunger returning and smiled.

She also saw the cluster of clothespins that so painfully covered her pussy, surprised to see how many there were.

He pushed his hand through them and scooped a copious amount their mixed juices out and smeared them around the hole that crowned her position.

‘At least he’s using lube, ’ she thought.

When he stood over her she could see that his lovely organ was already swollen hard with blood and ready to fill her virgin hole.

He took a position behind her back and rubbed his erection through their combined fluids a couple of times before pausing and pushing the head against her sphincter.

She closed her eyes and tried to relax but was ordered sternly, “Open your eyes. Look at me.”

She focused on his handsome face and let everything else fade away. When he began to push into her tight hole she shuddered but did not lose eye contact. His face was set as he steadily forced the head through the tight ring of muscle and then in a single thrust, all the way in until his wiry pubic hair made contact.

It was not as bad as she had feared. In fact, next to the biting wooden clips that covered the rest of her, it wasn’t too bad. She felt filled. More filled than she ever had with a cock in her pussy.

But she remembered how much he’d said he enjoyed her pain and made a bit of a show of it- wincing on the inward thrusts, sighing on the withdrawal. Every one shook the clothespins so the pain was quite real. She went into it, revelled in it, whimpered and sighed and moaned.

All of it, she saw, was reflected in his hungry look. She wanted his fury, wanted his unbridled lust, and began to softly plead and the openly beg for him to fuck her ass.

Her pleas were real and were kerosene on the flames of his lust.

After two previous orgasms, even a young man like Derek was not quite as quick to cum a third time. But she was so compelling, so perfect, that he was soon close.

She saw, and begged, “Please... Sir... fuck me harder... fuck my virgin hole... please... Sir, make me yours.”

That was it, that request that he knew would lead to her enslavement.

He thrust a few more times before erupting. Clenching his muscles he held a little back, climbed over her and fed her his cock. Still smelling and tasting of her asshole, it was shoved unceremoniously deep into her throat.

She wanted to wretch. Not from the flavor though, While it was certainly foul it was more just the idea that she found so repulsive she wanted to puke.

“Take it, ” he growled. “Clean your Master’s filthy cock like the disgusting slut you are.”

The humiliating words only served to make her suck and lick more eagerly. She loved being called that. No, she realized, she loved being that.