By C.M.Tyssen 2007
It was pitch black and Pauline had no idea where she was or exactly how much time had passed. She suspected it was a basement, however. There was a smell of damp cement and a slight chill in the air. The only thing that was certain was this: her limbs were immobilized. She seemed to be on her back, spread-eagle and tied to a bed. Pauline could hear creaking bed springs as she shifted and smell the mustiness of an old mattress. She also realized that she couldn’t close her mouth. A wide leather gag covered her mouth. But what was worse was that the gag held something firmly in her mouth.
Pauline’s lips were locked around something wide, cylindrical and hard. It filled Pauline’s mouth and it gave her tongue little room to move. But even if the gag did prevent Pauline from enunciating words, she could still make sounds. So she tried an interrogative moan. Maybe somebody would hear her? To her surprise she heard a muffled “MMMM” sound in response. Of course, Pauline still couldn’t see. Nor could she exactly locate the direction of the sound. But it did seem to come from within Pauline’s basement. Another slave? Probably. And truth be told, knowing she wasn’t alone in the dark reassured Pauline somehow. But that feeling didn’t last long. Apparently somebody had heard the noises being made by the prisoners. The muffled sound of slow, purposeful footsteps could be heard. Seconds passed and then Pauline heard the squeal of unseen door hinges opening and closing. And with a click, the basement was illuminated with the dim light of a single naked bulb that hung from a ceiling wire near the previously unseen door.
Turning her head to towards the light, Pauline immediately understood that she was now probably looking at the Jailer. She’d never actually met him before. Apparently, he was a loner who never attended any of the local play parties. But the Doms of the BDSM community liked to send him their misbehaving submissives for slave training. Weirdly, none of the subs who emerged from the Jailer's clutches ever talked about what happened. That fact alone made the Jailer scary… but it also made Pauline insanely curious. Was this the kind of man who could introduce her to taboos she didn’t even know existed? Did he know how to make a sub feel deliciously dirty? The mystery sparked fantasies...
And so in the end, Pauline engineered for herself a visit to the Jailer. Pauline deliberately provoked her own Dom with little acts of disobedience. And finally after weeks of feigned exasperation with her lack of discipline, her Dom decided it was time to send her to the expected slave training specialist: the Jailer.
It is common knowledge that being a sub does not mean you are giving up control over the situation. But right this minute, she didn't feel even a shred of control. In the dark of this musty basement, Pauline couldn’t help but remember that a person should be wary of what they wish for… because the Jailer seriously unnerved her. Pauline couldn’t see much beyond his silhouetted black outline. The man had moved far enough into the room so that the swinging bare bulb was now behind him. And this ensured that everything facing Pauline would remain in black shadow. He was of medium height and build, but beyond that, the only detail she could make out was the outline of a riding crop in one hand and a duffel bag in the other. At this point, Pauline also became aware of the other slave. Again, she could only make out an outline and no features, but Pauline could tell that it was a woman. She was mounted on a dungeon sawhorse: two sets of A-shaped legs joined by a thickly padded, horizontal board. The woman lay on her stomach. Two thick leather straps tied her torso to the pad. Her legs and arms seemed to be stretched down towards the ground and securely manacled and chained to the legs of the sawhorse. This other prisoner seemed to be naked, although the dim light did seem to be dimly reflecting off the outline of some patent leather ballet-style boots with insanely high heels.
The Jailer approached with leisurely steps. He was probably savoring the sight of what he beheld. As soon as he reached the other prisoner, he brought the crop down, hard, on the woman’s ass. She reacted with a sharp “Ugh!” sound. Her back arched and this set her dangling breasts to swaying as her startled body jerked against its manacles. A little metallic tinkling sound was also heard. Pauline suspected little bells had been clamped to the woman’s naked nipples. The Jailer leaned over and removed the other slave’s gag. As it was pulled away, Pauline could make out that a three-inch black penis was attached to the underside. And as this fake cock was pulled out of the prisoner’s helpless mouth, the light caught a thin silver stream of saliva spilling onto the concrete floor. Squatting in front of her face, the Jailer reached out with both hands to remove the bells dangling from the woman's nipple clamps. She gasped as blood began to painful circulate through her engorged nipples. Next, only using thumb and forefinger, he pinched and massaged her nipples. The woman's nipples were over-sensitized and she twisted her head from side to side. Pauline couldn't tell if it was from pleasure or pain.
Eventually, the Jailer spoke to the other slave. “I want to reward you for being such an obedient whore,” he began. “My friends very much enjoyed defiling your pretty mouth and face with their cocks last night. You might be ready to graduate from the Dungeon, after all. So I have a reward for you. Do you want to be a Pleasure Pig or a Pain Slut? You may answer me, now slut.”
“Sir, I want to be a Pleasure Pig, Sir.”
The Jailer considered this. Standing upright, he walked back around to the woman’s round, vulnerable ass. At first he brushed his fingers lightly down the curve of her back, stimulating her endorphins and coaxing little shivers of pleasure from the slave. And as he positioned himself behind her open legs, these fingers trailed over her round ass, down her crack, fluttering briefly over her anus and then inserting themselves smoothly into her sex. “You’re wet,” he commented without emotion.
He reached forward, grabbed a fistful of the slave’s hair. And while pulling her head up and back with one hand, he used the other to expertly masturbate the helpless slave. The slave moaned in appreciation as his fingers swirled around her clit. And as she grew more excited, the Jailer penetrated her with his fingers, brushing the slave’s G-spot. As the moments passed, her hands and feet strained against the cuffs. The intensity of feeling was causing the slave’s body to undulate in pleasure. The slave's moans and breathless gasps became sharper and louder. Her head began to thrash from side to side, but the Jailer kept a firm grip on her hair.
Suddenly the Jailer barked out: “Don’t cum without my permission!”
“Ooooh! Oh please, let me cum, Sir!” the poor slave managed to gasp.
“Are you a whore? Does the whore want to cum? Beg for it like you mean it!” The Jailer demanded.
“Yes, I’m a whore, Sir,” the slave almost screamed. And then a long high-pitched moan escaped her lips as she lost any ability to suppress the orgasm coursing through her body. Quick as lightning, the Jailer reacted by slapped her ass hard with an open palm. The surprise and pain caused her entire body to clench. And as intended, this only hightened the exquisite pain of feeling the Jailer brutally jam a well lubricated finger into her quivering ass.
“You were doing so well, dirty little slut” the Jailer explained. As the slave began to whimper piteously, he slipped a second finger into her ass. “But then you had to cum without waiting for my permission first. Break the rules and you get punished. It’s that simple.”
The man continued to massage and stretched her backdoor hole. Reaching down into his duffel bag, the Jailer pulled out a very large anal plug. He greased it with lubricant and firmly inserted the bulbous plug into her ass. Despite the pain, the slave submitted. Other than grimacing and making a mewling “ow! ow! ow!” sound at the roughness of the penetration, the slave made no further protest. She only managed to hang her head in exhaustion from the orgasm. Her back was glistening with sweat. Her butt and thighs were slick with the mess of her own juices.
“I haven't forgotten about you, little pony.” Pauline gave a start as she realized the man was talking to her. Her mouth went dry and the plastic cock held in her mouth by the gag tasted bitter. The Jailer approached and stood at the foot of Pauline’s bed. “I’ve been told that you're disobediant and willful. Your Master told me to break you in like a horse. I look forward to training you.”
Pauline felt her heart rate pick up with a mixture of both nervousness and arousal. She was hyper-aware of the tightness of her own cuffs that tied her to the creaking bed; the hardness of her perky nipples and the increasing wetness of her cunt. She was looking forward to training, too...
To be continued.
This photo reminds me of a time a tied Simone with her arms over her head in a door frame. I was pretty happy with the results of my personal photo shoot I recall.
Amoung the things I like about the above picture are the fetish elements of the boots, thigh highs and the yanking of the dog collar.
I like the exotic beauty of this model. The enchanting complexity of the Japanese-style bondage rope is well displayed. Notice the knot in the rope running between her legs? I like this techniques of placing a thing knot at the anus or clit to stimulate a sense of vulnerability and even discomfort in a sub.
Classic heels, thigh-highs and corset. My absolute favorite lingerie combination. This pose fills me with pure lust as I think back to lingerie shopping in Paris. 
This picture pretty much touches on every fetish I appreciate most: slender long legs, great ass, thigh high stockings and sexy heels. Imagining dripping my hot cum on this back and ass: priceless.
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It's also worth saying that Taboo provide me with my first photographic visuals of kinks that would eventually loom very large as sexual fantasy triggers. In fact, the following images from a 2001 pictorial of a bondage wedding is quite significant in my 
Of course, even good things come to an end eventually. Like Saturday Night Live, even the sublime eventually decays into the absurd. I had a good run with Taboo and it influenced me greatly in developing my interest in bondage as an aesthetic appreciation. But that really could only blossom further by finding porn that specialized in rope bondage.
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