Sailor Moon Ch. 03

Master nodded. "The good news is that Madam may have further gifts for you." Scott closed his eyes. Clearly that was a reference to the strap-on, and he wasn't going to give either of them the satisfaction of acknowledging that he knew that.

"However," Master continued, "we also believe in surprise presents to... well, you know, spice up the occasion."

To Scott's further surprise, Master proceeded to unzip his own pants and reveal a pair of dark black boxers. Men's underwear, Scott noted, the kind he would have worn a while back. Not like the frilly red Care Bears panties that had so recently adorned his backside. The black boxers were not visible for long though, as Master quickly dropped those too and revealed a large cock that made Scott gasp. It was huge - certainly bigger than his, even though Scott still defiantly knew that his was not small, no matter what those mean sorority girls had said. It was only half-erect, but nevertheless it hung out with an impressive length and girth. Madam gave it an appreciative look and then smirked at Scott.

"So," Master continued, completely at ease with his manhood being on display, "we're both going to head around to the back of the pillory, and you're soft, sissy, girly ass is going to be treated to some special attention by one of us."

Scott gulped. "W... who?" he asked, finally finding his voice.

Master shook his head. "Well, that would be telling, wouldn't it?"

Scott started to struggle again for a few seconds as the reality of what was about to happen struck him. It felt like a hard slap across his face, and he could feel his cheeks burn with embarrassment.

Master and Madam didn't wait to engage in any further conversation, and each took a different side to pass around the edge of the pillory, until both were out of sight. Scott flexed his wrists and ankles, but all of them were securely bound and gave no room for maneuver.

Then, seconds after both Master and Madam had disappeared, Scott gave an involuntary "ooff!" as the leash tightened on his cock cage and he felt his manhood stretched backward.

Seconds ticked by, and Scott's mind began to race. He heard a tube being opened, and then another hand intrusively rubbed something cold into his exposed anus. Scott yelp at the contact.

"I assume you'd prefer we lube up?" Master said, "or would you like us to go in raw?" there was a teasing quality to the voice, and Scott's own reply betrayed a trembling fear. "Please. Lube. Yes, lube."

He let out another hiss as he felt a finger apply another round of lube, and this time press some into his tightly clenched anus.

Then, Scott was left to contemplate his predicament for a few more agonising seconds. Who would he feel? Madam with her strap on, or Master with his huge phallus? Would he even know? Scott had never had anal sex before, never been with a man before - unless Robert's hand-job counted in the forest in his last trials - and he didn't even know how it should feel. Scott's mind was a sea of turbulent emotions as the sheer helplessness of his current situation and the thought of being ass-fucked by either of these people, drowned out any other rational thought.

He was not left to wonder what it would feel like for long though. As he clenched his hands, and gritted his teeth, squeezing his eyes shut in an attempt to block out the room around him, he felt something large touch his bottom, sliding between his ass cheeks.

He ass tightened, but a tug on his cock cage told him that this was exactly what he was not to do. He tried to relax, but given the circumstances that was more than a little difficult!

Then whatever it was, the strap-on or Master's cock, touched his anus, and began to push inside.

Scott's eyes flew open in shock.

"FUCK!!" he shouted, as the large object began to slide inside of him.

"OH SHIT!! FUCK!!" he almost bit his own tongue, and tried to buck his body, but it was no good. Whatever it was slid deeper and deeper, before stopping for a moment, and then beginning to slide out.

Scott panted, as he tried to stop from hyperventilating. The object didn't pull all the way out though, and halfway back paused again, and then slid in further.

Scott grunted with the exertion of receiving this intrusion to his virgin bottom, and he felt his muscles protest at the invasion.

In and out the object slid, each time it went in going just a short distance further than the last time. Scott's eyes almost rolled back in his head, and he puffed out some air, slowly getting his breathing under control.

Then, whenever whoever was riding his ass seemed satisfied that they'd gone as deep as they could, the rhythm of the movements began to pick up.

"Fuck, fuck, shit, fuck." Scott panted. He couldn't move, his ass completely at the mercy of whoever was riding him. Back and forth he felt the object go - dildo or real cock, he knew not which - and Scott felt sweat begin to build up on his face as his heart raced.

He kept taking short breathes in and out. The constant riding of his ass made his bottom ache, and feeling the large object inside him was a completely alien sensation. Worse still, he felt his cock begin to stiffen against the tight restraints of the cock cage, and through a hazy mist, he realised that it would have nowhere to grow and expand.

"Dear God, no." Scott thought, this was absolutely not the time to get aroused. Why the fuck was he getting aroused by this?! Fighting against the leather and metal of the cage, the blood rushing to his penis gave him one more agony to moan about.

In and out, in and out, the pounding continued. Whoever was taking liberties on his bottom slowed down occasionally, and the first time this occurred Scott tricked himself into believing that it meant to the ordeal was over. However, they then sped up their thrusting again, and even found an extra inch or so to force their way down his ass even more.

Scott groaned and tossed his heads around as much as he could in the pillory, unable to do anything other that receive this "gift" and wait for his rider to tire.

As the seconds passed into minutes though, it seemed either Master or Madam didn't just have the girth and length of a horse, but the stamina of one too...

****

Scott's head dropped and sweat dripped from his brow as he felt the appendage finally withdraw from where it had been firmly lodged in his bottom. He groaned for the umpteenth time as the tip finally popped out, and he sucked in a long breath as he felt his anus finally begin to close. His breathing was ragged, his brain still unable to fully contemplate this latest experience. Blearily staring at the dark wall in front of him, Scott started to shiver as competing visions of what had just happened - the first of a large muscular man, the second of an not-overly-attractive woman with a strap-on, both pounding him in his helpless, exposed ass - overwhelmed any other thought. Which had been the truth?

He spat out some saliva that had gathered in his mouth, and tried to shut out the visions. The physical experience itself had been humiliating enough, but not even knowing exactly what had just happened somehow made it even worse.

He heard footsteps to his right. A well-heeled shoe striking the hard floor, and he instinctively looked, hoping that it was Master returning to unlock him from the pillory. Would he see Master appear though, with his large cock exposed? Had that been what had just been inside of him? At that thought, he tried to look away, but he couldn't. As Master finally appeared, he stopped at the side of the pillory. His pants were zipped up, and for a moment Scott took that as a sign that it had been the woman with the strap on who had just been pegging him mercilessly. Still, Scott now realised that his sense of time was progressing so erratically while locked in the stocks that he couldn't discount the possibility that Master had taken his leisure in cleaning up and dressing before having decided to re-appear.

As he strained his eyes, he tried to get any kind of signal from Master as to what had just happened, whether he'd done well, or what was to come next. Instead, the man just looked impassively back at him. If _he'd_ be who had been just inside Scott, wouldn't he have cum? Wouldn't he have at least some indication on his face from the exertions of what must surely have been only a few moments ago? Or had Scott been groaning and heaving for five or ten minutes and gotten so lost in situation that he'd missed that?

Footsteps again. Scott looked back sharply at Master, but Master was still just standing there, one hand holding on to the pillory. Scott opened his mouth to say something, and then realised that this time the footsteps were coming from his left. They were also sharper, as if it was a high heel this time. The woman.

Scott slowly looked left, and it only took a few seconds for her to appear, not bothering to walk all the way around and instead taking up a similar position at the side of the pillory. The large strap-on hung down from her pelvic region, and Scott drew in a deep breath as he imagined her thrusting in and out of him. While not completely unattractive, she was a large woman with several pounds of excess fat, and when he'd fantasied in the past about being dominated by a woman, they'd all the physiques of porn stars in his mind. She gave him a strange smile, and his mind raced as to how to interpret that.

Then she raised one hand and showed her palm to him. Resting between two outstretched fingers, he could make out a leash handle. Tightening her fist again, she pulled her hand back a few inches and he grimaced as he felt the tug on his balls. Between gritted teeth he tried to ask her to stop, but instead she just flicked the strap a few times and he could feel the wave pass down the leash and jiggle his constrained cock, further exemplifying just how defenseless he was in his current predicament. She winked, and he broke eye contact with her in case that caused her to lose interest in teasing his helpless manhood.

He looked back at Master and croaked "W... who?"

Master raised an eyebrow, giving Scott a stare that was neither aggressive nor pitying, but seemed merely contemplative. As if wondering which answer Scott would prefer to hear. Then he looked up at his female companion and spoke in a calm, authoritative voice. "She wants to know who. Should we ask them to tell her?"

Scott squinted his eyes as he processed what Master had just said. Then, looked back and forth between Master and the woman as a gnawing doubt began to eat away at him. "Wh... what? Who?" Scott shook his head, trying to focus. "Ask who?"

The woman merely nodded at Master with a smile, and gripped her side of the pillory. With a click, Scott felt the pillory suddenly come free from the floor, and he realised that there must have been hidden wheels by the base. That of course made sense, otherwise how would it have gotten into the room in the first place, but now that he realised he could be wheeled around, that somehow contrived to make a bad situation even worse. The pillory began to be spun around and Scott - his feet still bound by cuffs with short chains to the base of the device - had to shuffle his feet frantically to keep up, otherwise his bare feet would drag on the floor painfully. The woman didn't help by taking the liberty of jerking and flicking the leash whenever she felt like it, causing his tightly restrained cock and balls to pull and twist. He clenched his eyes shut to futilely try to block out the sensation, and thus it was only when they were already most of the way around that he sensed that there was something else hovering in front of him. He re-opened his eyes and let out an involuntary squeal.

They were not alone! Three rows of strangers in sleek black, fold-up chairs, were silently staring at him. He forgot how to breath for a moment, and his eyes almost popped out of their sockets as he looked back wild-eyed at them. Each of these strangers, each of these grown, adult, sensibly attired strangers, had just been witness to arguably the most embarrassing incident in his entire life. And now each and every one of them had a perfect mental imprint of what his face looked like, and also what his ass looked like in a silly, girly, dress, while someone performed anal sex on him.

He tried to say "Oh fuck." but no sound escaped his lips. Instinctively he tried to tug at the stocks, but his hands, neck and feet were still firmly locked in.

As he scanned the crowd, he saw a tall african-american gentleman in the front row, who raised a hand and gave him a short wave. His face had an expression of amusement, of anticipation and of a strange kind of hunger. Scott recognised him with a jolt - it was Jonathan from the cafe - and the eager look he gave Scott carried the impression that Jonathan was imagining himself prone, bound and powerless, completely at the mercies of the Master and Madam.

Now that Master was satisfied that the pillory was in the right position, he started to walk around again and stood right next to Scott's face. As it turned out, bent over in the stocks as he was, his face was pretty close to Master's crotch. Scott went bug eyed at the thought of what could be coming next.

However, Master simply lay one hand gently on Scott's head, and twisted it slowly so that Scott was forced to look out at the audience.

"Serena wishes to know who was just giving her soft, sissy ass the treatment it was so sorely begging for."

Master raised a finger to his lips though, as if to indicate to the audience to not answer just yet. "Shall we ask her first, who she most wanted to pound her soft, girly bottom?"

Scott groaned and closed his eyes, not wanting to contemplate how he could possibly answer that question in front of strangers. He yelped though as he felt a sharp and swift tug on his tuck. The woman said "Don't be rude, look at your audience when you are being asked to address them."

Scott opened his eyes again with a grimace, and parted his lips. No words came out still.

"Serena," Master said, firmly but calmly, "who do you wish the most it had been? Me, or Madam?"

On some level, Scott knew that Master was directing him to say that it was Master he most wished to have been inside him. To have him say in front of all of these strangers, who knew his face now, that Scott wished he'd been fucked in the ass by a man.

Deep down, Scott realised he wasn't even sure of the answer himself. He was so confused, the experience so overwhelming, that he was beginning to lose track of who he thought he was. If he'd been asked four weeks ago, the idea of being penetrated by a man would never have crossed his mind. The woman, plus-sized and in her forties at least, also wasn't someone he'd fantasied about being dominated by. There was something even more humiliating about being ridden by a woman he'd ordinarily have passed in the streets without even giving a second look. He wouldn't have turned around after she'd walked by and checked out her ass as she disappeared down the streets. He could easily have not even noticed she existed. And yet, potentially, a few minutes ago, she may have been the one having complete and free reign over his ass, the sole determinant of how deep and how fast each thrust would be into his virgin anus.

"I..." Scott gulped, and decided to go with the safest option, the option he thought Master wanted to hear. "Y... you sir. You. I wish it was you." He closed his eyes again, his cheeks flushing an even deeper shade of red than they had already been. This time at least, he was allowed to keep his eyes shut for a few seconds to contemplate what he'd just publicly said, before the woman gave a reminder - more gently this time - to open his eyes.

"Well," Master said, "fortunately for you, you've been a very lucky girl then."

Scott took in a deep breath and trembled. So that confirmed it then, he'd just been fucked by a man then. There were no tears, no wails, no cries of denial, Scott just stood there trembling, wondering what it meant that he almost felt relieved - surely just at the sense of now knowing, at least? - and mentally counting the seconds until he'd be released and would be allowed to retreat back to his own private world.

"However," Master said, turning Scott's head to look at his female companion, "it seems awfully rude of us not to ensure Madam's needs have also been sated." Master looked out at the audience, and gave a sweeping gesture with his other arm. "How shall we ensure Serena repays Madam for her time and efforts?"

He let go of Scott's hair, and Scott dropped his head to give his neck a short break, but then looked up cautiously at the audience, wondering what they might have in store for him next. He didn't have to wait long, a confident hand shot up from a well-attired Asian woman in her fifties.

The Master pointed at the woman and indicated for her to speak.

"Make her eat Madam's pussy out, while Madam sits on her face." she said, in a matter-of-fact tone that seemed completely at odds with the bizarreness of the request. Scott tried to recoil, but he was still unable to move, and simply had to stand there as the Master made a show of considering the offer, before he looked across the his female companion and raised an inquisitive eyebrow. There were no words exchanged, but as Scott looked on, the woman simply undid the straps on the dildo she'd been wearing, and let it drop to the floor. The signal was unmistakable, and Scott closed his eyes as he felt hands go to work at releasing him from the pillory.

This was no escape though or indication that his trials were over. No, this was simply an acknowledgement that he couldn't eat out this large, forty year old woman's pussy in his current position. There was still further humiliation in store for him.

As he finally felt the neck restraint lift off, freeing both his head and his hands, he partly stood up and tried to stretch out his aching muscles. His ass still felt sore from the treatment it had just received, and even when his feet were finally released as well, he couldn't quite bring himself to straighten up to his full height entirely.

He looked submissively at Master, who pointed at the floor between the audience and the pillory. "Lie down." he said, simply. There was no use fighting this. Straightening out his dress as much as he could, he reached down to pull his panties up from where they were pooled around one of his ankles, before remembering first to look up at Master and ask permission. To Scott's relief, Master nodded his head, and Scott pulled the panties up to hide the cock cage. That he could be relieved to be flashing his silly, girly cartoon panties to these strangers was an incredible thought, and yet here he was, reduced to being thankful for these small mercies.

He shuffled over to where the Master had pointed to on the floor, and dropped down, grunting a little with the exertion as his sore ass protested at being forced to lie down. Master walked over to where Scott was now laying in his final and ultimate surrender, and kneeled down. "Move from that spot before I say so, and you know the consequences." Scott nodded dumbly, and did nothing as Master casually leaned back and flicked up the front of Scott's dress so his panties were on full display to the audience. The leash still snaked out from underneath the panties, from where it was firmly secured to his cock cage. The other end of the leash rested in Madam's hands, who was now approaching Scott with a look of absolute mischief.

Within seconds she was standing over him. Scott stared impassively up. She was not the type of woman he normally fantasised about. Not hideously unattractive or massively obese, but certainly older and larger than the women he'd dreamed about. He dreamed about the type of women who'd seen him on the highway, twenty-somethings with young, supple bodies and tight asses. And yet, those other women weren't here and she was.