BDSM Mistress Teaches Submissive Female the Art of Submission and Painful Pleasure

Our charming lady enjoys the learning experience as she finds out more and more about herself.



The Sugar Cane Plantation - Chapter 2



As another day bloomed on the tropical island, she couldn’t help thinking about what the evening might bring?

Was it possible to OD on kink? In the back of her mind she wondered if she could overdo it and become blasé? Certainly would not want that to happen – she was enjoying this too much. She vowed to discus it with her new friends later. For now the pool beckoned and she stretched out – enjoying the warm tropical sun.

When she wandered into the main building for lunch it was a continuation of the morning awakening.

The exact antithesis of the night before! June had apparently had a change of heart, for Eric was sitting with her having lunch. June saw her enter and waved her over to join them.

It was a little awkward sitting at the table with Eric – this is the first time she had seen him in any way clothed and not in some way restrained. She looked around and saw Steve and Sharon enjoying an intimate lunch – holding hands and looking every bit the happy tourists.

June saw her surveying the scene and understood at once.

Laughing lightly she said ”come on Cynthia, we can’t run around being perverts all the time!”

She was right and it brought a smile to Cynthia’s lips. “You’re right of course – it just seems as if that’s been the focus of everything over the past couple of day. I was thinking about that out by the pool – perspective, perspective, perspective!”

They sat enjoying their lunch. No one was at any of the nearby tables so they could talk freely.

Eric said little, deferring to June, who smiled as she observed Cynthia glancing at Eric.

“Yes I’m sometimes a pushover” she admitted. “I know he is supposed to be locked up all week, but he was so very good last night, I decided to give him a break today. And besides, he’s not totally unrestrained – I never allow that”.

Cynthia glanced at Eric who still said nothing, then seeing no sign of anything limiting his freedom, looked quizzically at June.

As if her husband were not present June explained, obviously amused at Cynthia’s unasked question. “My husband is a hopeless masturbator “ she said. “If I don’t control him, he’s constantly playing with himself.”

Eric was now visibly embarrassed as Cynthia gave him a sidelong glance.

June continued, much to Eric’s discomfort. “When we decided that we would live a femdom marriage, Eric gave me control of his cock and balls – didn’t you dear?” she asked her husband. He answered sheepishly in the affirmative, avoiding eye contact with Cynthia.

“So, whenever he’s not otherwise restrained, I have a couple of little toys that I use to make sure that he refrains from self abuse. He’s wearing one now” June explained. “Eric, my dear, our friend is curious about how I control your dick – why don’t you explain to her what you’re wearing and how it works.”

“Yes Ma’am” Eric answered, recognizing the authority in his wife’s voice. He turned to Cynthia and explained….

“Before we left the room today, Mistress locked my penis into a kali teeth ring to prevent me from touching myself without permission. It is a device that discourages an erection, and makes any touch to my penis painful. I’m required to wear it, or some other form of chastity device that we have whenever Mistress allows me to be otherwise unrestrained.”

Cynthia felt the now all too familiar thrill as she listened to this man describe how his wife kept him locked up to prevent masturbation – to exercise complete control over his sexuality.

First last night, and now again she realized it turned her on to see a man submit and give up control. She fell right into her role.

Ignoring Eric, she asked June what a Kali Teeth Ring was. Almost clinically June explained the device, telling her that it was a metal sleeve that was locked around the shaft of the penis, just behind the head, the interior of which was lined with sharp spikes.

She went on to explain how when the penis was flaccid it was only mildly uncomfortable but that as the penis began to swell when becoming erect, the spikes would dig painfully into it. The more it grew, the more it hurt until finally, the pain would make the erection subside.

Cynthia was watching Eric with amusement as his wife was casually explaining to her the manner in which she controlled access to his penis – controlled him sexually.

He was clearly embarrassed at being discussed this way. but she noticed something else.

“It really is quite effective” continued Julie. “Tease him a little and watch what happens.

Cynthia looked around to see if anyone could see them, and finding that the plants behind the table gave them some privacy, let her hand slip onto Eric’s lap, gently teasing.

She felt the all too familiar twinges between her legs as she let her fingers play around his crotch, feeling the hard metal through the fabric of his slacks.

Running her fingers along the shaft of his cock, feeling the outline through the pants, she felt it begin to stiffen at the same time that she heard Eric sharply inhale.

“He’s such a slut he can’t control himself” Julie said as she watched her friend tease her husband’s cock. “He knows how badly it’s going to hurt, but he can’t help himself.”

“He looks like he’s in real pain” Cynthia observed as she watched Eric try to move as little as possible, with beads of sweat appearing on his forehead.

“Oh he is” smiled June. “I love to see my wonderful husband in pain. Later, I’ll show you what’s causing him to make such a fuss. It’s quite diabolical in that he’s the one causing his own pain!”

“Shall we go and enjoy ourselves?” June asked Cynthia who readily agreed.

“Eric, you have the afternoon to yourself. “Julie ordered. “But don’t think I’ve forgotten your misdeeds. I expect you to be in your cell, naked and restrained, before the sun goes down. I’m sure we’ll be able to put you to good use later this evening” she told him as she gathered her purse to leave.

The two women wandered outside, enjoying the tropical sun tempered by the cooling breeze.

Without even talking about it they found themselves walking toward Cynthia’s room.

Once inside Cynthia turned toward her friend – no words were spoken – they just slipped into each others’ embrace – hands searching and stroking, lips meshed, tongues intertwined.

Moving over to the bed they were soon a lust fevered mess – arms, legs, clothes all entangled, and neither of them caring.

Cynthia found herself lying between June’s widespread legs, ever so intensely licking at the soft folds, probing with her tongue, then taking the swollen clit between her teeth and pulling. As she relaxed her bite just enough so that the captive clit slowly slid out, rasping against her teeth, June explode into a convulsive orgasm, her juices soaking Cynthia’s face as well as the sheets.

Cynthia, knowing how sensitive it would be, simply placed her tongue against June’s clit. Not moving, just a gently rolling pressure as she felt her liver’s gradually subsiding spasms.

They lay quietly for a while, June enjoying the afterglow of her intense orgasm, just holding each other. Cynthia was aroused and unsated, but not concerned – they had all afternoon.

Besides, she was enjoying the gently building sensations caused by June’s fingertips lightly teasing her nipple. So very nice. So unhurried.

Just lying there, literally able to feel the nipple swelling and hardening as the fingers slowly circled and teased, and wondering where those fingers might end up next and hw long they would take to get there.

June interrupted her erotic meanderings. “So are you ready to make our way to the dungeon this afternoon?” “Ummm – always” she answered” feeling that little twinges that thoughts of play stirred.

“Well have you given any thought to what you’d like to do?” her friend asked, now leaning over and blowing ever so gently on the same nipple she had been teasing.

Cynthia could literally feel the nipple trying to explode – she wanted so badly to feel June’s tongue on it, but waiting patiently.

“You’ve played a little with the guys, and you’ve watched a lot” continued June, her mouth so close to the nipple that her breath as she spoke sending quivers all the way down to Cynthia’s pussy.

“Would you like to put me through my paces, or would you like me to make you scream? June asked, ending the question by twirling her tongue around the nipple.

Cynthia jerked visibly as the tongue touched her swollen nipple.

She stopped to think. On the one hand it would be so much fun to have June at her disposal, to hear her moan and cry out in her restraints as she used a whip on those very sensitive parts of her body.

On the other hand, memories of her first adventure came rushing back. Visions of herself being strapped down, open and exposed, while June exercised what Cynthia now knew to be a healthy streak of cruelty.

It was hard to say if it was those thoughts, or June’s finger lightly teasing her slit that almost sent her over the edge.

Sensing her indecision, June told her that before she decided, she needed to be aware of a few things if she was considering submitting

“First sexy lady, as I think you’ve seen, I play hard. I won’t injure you. I won’t leave any permanent marks and we can discuss ahead of time anything you really don’t want to do, but outside of that, well let’s just say that I will want to hear you scream!”

Cynthia shuddered at the images that statement conjured up in her mind, at the same time, letting herself go to the wonderful feelings coming from her pussy as June continued to gently stroke and tease her. Not yet putting a finger inside her – just making her crave it as she gently but incessantly stroked the outer lips.

“Beyond the physical aspects, I really focus on the mental.

A session can be as intense mentally, or probably more so than physically. The body generally does not remember pain – but the mind certainly remembers the trips that it has taken.” June continued.

Now her finger was ever so gently nudging the out lips apart – just barely stroking between them, but the wetness was already abundant, and Cynthia moaned at the sensation.

“One thing that I do differently than most is that I don’t use safewords”. Cynthia opened her eyes quizzically and June continued to explain, though not stopping her stroking and teasing.

“Most of the BDSM community religiously uses safewords in play. Those are words, agreed upon ahead of time that if spoken by the “victim”, automatically stop everything.

For some they’re fine and certainly to each his own. For me” June continued as Cynthia tried to listen attentively while feeling her pussy begin to swell and throb, “they completely destroy the whole mental side of what I do”.

Confused, Cynthia turned her head in spite of the wonderful feelings coming from between her legs. June was enjoying that she had Cynthia’s attention – both regarding what she was talking about as well as what she was doing, and went on.

“When I am dominant in a session, I want my victim to be in the mindset that can only come when they realize that I and only I am in control and that whatever is going to happen to them will happen whether they want it to or not. It is complete surrender. Complete trust. Complete relinquishment of control. All that is completely destroyed if they realize that all they have to do is say “red” or “asparagus” or something.”

It made sense thought Cynthia and she even tried to say something intelligent in response, but all she could do was moan as June’s finger finally slipped between her now slick lips and teased her clit.

She felt June kissing her way down her body moving so slowly toward her throbbing and oh so needy sex. Finally just as she felt a finger slip inside her she felt June’s lips circling her clit. Another finger joined the first and by spreading her fingers, June began to stretch her vagina.

The feeling was indescribable and grew in waves. Just as she thought it could not get any more intense, June withdrew one of the slick fingers and nudged it against Cynthia’s ass, itself slick and wet from the juices that had been seeping from her vulva. The finger slipped inside easily and Cynthia thought she would die from sensory overload – lips sucking her clit while June rubbed her fingers together inside her separated only by a thin membrane.

Cynthia thrashed and jerked on the bed, hearing what seemed like a distance voice crying out “Yes – God Yes – I want it – I want you to take me and whip my cunt – I want you to make me scream!”. As she came in violent spasms, finally realizing that the voice had been hers.

As the two women lay together in each others’ arms, June reached over ad stroked her friend’s face gently. “Wow” was all Cynthia could say, though she said it several times.

“Well love, did you mean what you said, or was that just throes of passion talking?” June asked.

“No – I meant it” said Cynthia. “That mind shattering orgasm probably let it out, but ever since Robert locked me in the cell, and then later, when I watched Sharon taking her pussy whipping, it’s been on my mind”.

June pulled her closer, both women enjoying each other. “Just make sure it’s what you want love, and make sure you want it from me. As I told you, I play rough. No safe words. No mercy. If you play with me you will scream, and beg and plead for it to stop and it won’t.

Think about playing with Robert – he can be cruel but he doesn’t share my need. I need it all! I want your mind and your body and for at least a short time, I want your soul!!!”

Cynthia hardly hesitated. “I know all that. I’ve watched you with Eric and with Robert. I’ve jumped into this with both feet. I want this – no I need this, and no, before you ask, or mention it, no matter how bad it is, I won’t hate you when it’s over.”

Junes said nothing for a while – just stroked her lover’s hair and face.

Finally she got up and pulled her clothes from the tangled mess, dressing herself as she found each item. As Cynthia started to do the same, June stopped her.

“Not you love. Your time starts right now, and right now, I want you naked for me”.

Cynthia had not expected that, and even after her adventure with Robert several days ago, it was strange. Embarrassing but arousing too.

Even though she had just shared a bed with June, and they had explored each other’s bodies in the most intimate possible detail, it still caused her to feel a blush and at the same time, her familiar rush at being naked while June was fully clothed.

She felt herself going down the road of submission when June dangled a pair of handcuffs before her, offering them with the words “behind your back lover”.

She found herself confused at the sensations and feelings that rushed over her as, standing naked in front of her friend and lover, she fastened one cuff around her left wrist, then putting her hands behind her back and fumbling for the other cuff, placed her right wrist in it. She felt almost overwhelmed as she closed the cuff, hearing the ratcheting sound and feeling the cuff tighten on her wrist at the same time.

She took a deep breath as she stood naked in front of her friend, hands cuffed behind her, waiting…

June enjoyed watching her friend’s embarrassment – she knew quite well the effect she was creating.

“Now my love, before we move on, let’s talk a bit. And oh yes, even though I’ve got you just the way I want you, you’ll have one more chance to back out”.

“Remember I told you that I don’t use safe words. That will go for our session today. I want you completely my love”. June whispered as she walked behind her manacled friend and lover.

“So, since once I get you in the dungeon, you’re mine. We need to talk about your limits.

Everyone has things that they just don’t want, that scare them to much, that they find distasteful or even disgusting. Now is the time to tell me your deepest and darkest fears and turn-offs. I want you frightened, trembling, nervous al at the same time, but I want it in a hot way for us. So now is the time to talk to me.”

It was all new to Cynthia but June helped her talk it through.

A lot of hugging and stroking of her captive and soon June had a good idea of what was fair game and what would be left alone.

So it was time to move on. She was really attracted to this woman, enjoyed making love with her, so she knew the session would be special. She wasn’t sure how their budding relationship would be affected by what she was going to put the sexy young woman through, but she had a good feeling about it.

“Ok my sexy little lover. It’s decision time”. I’ve enjoyed having you naked and cuffed in front of me more than you can know, and I am really, really looking forward to having my way with you in the dungeon.

But, I put the handcuffs on you before we talked so fair is fair, one more chance to change your mind.

Here’s the key to the handcuffs. Say the word and I’ll unlock them, you can get dressed and we’ll enjoy a nice dinner together, with hopefully an encore of our afternoon delight.

On the other hand, if you don’t want they key, we go to the dungeon and you’re mine for as long as I want you”.

As she spoke she walked around behind her captive, reached around and began stroking and teasing her. First massaging the delightful breasts, teasing then pinching the nipples, enjoying watching the effect as Cynthia leaned back against her, moaning at the caresses.

Leaning forward and almost whispering in Cynthia’s ear June let her fingers slip down the front of the woman’s body – lingering here and there. “What’s it gong to be my love” she whispered as at her touch, Cynthia’s leg parted, giving access.

“As the man said in “The Matrix” do you want the red pill or the blue pill? Dinner or the dungeon” as she let hr fingers dance lightly over her captive’s swollen sex.

“The dungeon” hissed Cynthia as she thrust her hips forward, trying to increase the pressure on her needy pussy.

“So be it” June murmured as she removed her hand, eliciting a gasp of frustration. “Don’t say I didn’t give you the chance to change your mind, and don’t say I didn’t warn you”.

June reached into a bag and pulled forth a paid of clover clamps which she held up for her lover to see.

“These my dear are what we call clover clamps. They go on shall we say sensitive parts of body. And, for your pleasure and enjoyment, they have a distinctive feature. When you pull on the little cord, they tighten. The harder you pull, the tighter they get, so it’s almost impossible to pull them off”.

Cynthia’s eyes widened a she watched June approach with the clamps. She felt first her left nipple, then the right teased and stroked tell they were erect. Then, just as she thought she had mentally prepared herself for the bite of the clamps on her breasts, June knelt down, nudged her legs apart and began stroking and pulling her outer labia. Before she could register what was happening she felt the excruciating pinches as the clamps were applied to her pussy lips. June next produced a leash, which she clipped to the chain connecting the two clamps.

Those feelings were overwhelming her again – just as when Robert had her locked in the cell.

She was naked, handcuffed and now had a leash effectively attached to her sex.

Just as she was trying to digest it all, June intruded into her thoughts. “Pleasant surprise too, my love” she said as she lightly held

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THE END