Sailor Moon Ch. 03

Story Info
Scott / Serena takes on the mantle of sissy-in-training.
16.3k words
4.52
7.8k
2

Part 3 of the 3 part series

Updated 06/09/2023
Created 01/24/2020
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[In "Sailor Moon: Ch 2", Scott took a few faltering steps down the path to being a sissy at the hands of the Master. Having barely held his nerve to beat another aspiring sissy - Robert - in a test of daring, Scott has now been named "Serena" by Master, who has left Scott at the deserted rest stop by the motorway dressed in his red Sailor Moon outfit. While Scott has his car only ten feet away, there is the small matter of his keys, wallet and phone, which Master has driven off with, promising to toss them on to the verge of the motorway a short distance away. However, what may be a short distance for Master in his truck, may prove to be quite a long way for Scott in his Sailor Moon attire...]

****

The roar of the engine as the car passed by couldn't drown out the rippling laughter that cut through the crisp spring air. If Scott's psyche could have curled up into an even tighter ball of shame, he'd have been in danger of having several emotional crushed ribs and a permanent kink to his psychological spine. As it were, he was instead stuck out on the side of the highway, desperately looking ahead for any sign at all of the velvet bag that the stranger had dangled in front of him only minutes ago, and in which resided his phone, his car keys, and his wallet.

The mad thought crossed his frazzled mind that he'd never actually walked along the side of a motorway before. Such a hum-drum, boring thing, and yet here he was. Cars blasting by, horns blaring, jeers and whistles slicing through the background noise with an inevitability and regularity that caused him to flinch and shudder under the constant searing humiliation.

For as boring and as hum-drum as walking alongside a motorway would have seemed to any normal man, the travellers out in force today were being treated to the sight of a highly embarrassed sissy-in-training, clad in a full-blown Sailor Moon outfit. The heeled boots certainly didn't help, causing every step to be a half-stumble and robbing him of even the vaguest sense of dignity that having had a confident stride may have provided. Instead, his attention careened between straining his eyes for any hint of the bag that held his possessions, trying not to fall flat on his face and flash his ass to the cars blasting past from behind, and attempting to block out the constant intrusive thoughts that surely some of these drivers would have dash cams that his red-faced stomach-churning humiliation permanently recorded. He'd been out on the road now for three minutes, although each second seemed to drag on for so long that he'd - in all practical senses - lost track of time.

The large red bow on his clearly feminine white blouse was the same shade as his face, and he tried to hide his features behind raised arms, although he had to lower them to scan the verge properly. The last thing he could afford to do is walk past where the velvet bag lay, and have to double-back miles down the highway.

His frilly blue skirt was also misbehaving in a stiff spring breeze, and occasionally flashed a pair of panties to drivers that resulted in yet more honks and whistles.

Each one was like a dagger thrust into the feeble corpse of what was left of his dignity and masculinity. He couldn't easily hold his skirt down and hide his face, and a sense of helplessness was beginning to paralyse his movements and his decision making to the point where his face and his panties were both more on exhibition than they truly needed to be.

He groaned for what was probably the twentieth time as he urgently looked ahead and around. That damn velvet bag had to be somewhere.

Then, as he stumbled along, he heard a sound that he'd been half-expecting and wholly-dreading. It was the sound of a vehicle slowing down behind him. He refused to turn around, and instead soldiered on as best he could. The sound of tires beginning to cruise over the gravel on the side of the highway was unmistakable though, and Scott knew he was about to have company.

Then the mad thought occurred to him that it must be the Master, who had decided to turn around and end this little exercise in case Scott was hauled over by police and their entire sordid ordeal came to light. An ordeal that would surely get Master into just as much trouble as Scott, even if Scott's dignity and standing would be immeasurably more impacted.

He spun around - a mistake as he wasn't used to such movements in his red knee-high Sailor Moon boots - and lost his balance in the act. Falling back, his legs splayed up, flashing his pink panties to the new arrivals, and giving Scott a sore bottom into the bargain.

He looked up, wincing from the impact of the ground and shuddered. It was not Master. Instead, a van load of 20-something women - college students on a road trip most probably - were gawking at him through the windscreen of their vehicle. Scott desperately trust a hand towards his skirt and panties to try and cover up, but it was too late. One of the women - an attractive blonde-haired woman with well-tanned skin - leaned out of the window.

'What the fuck are you dressed as?" she asked, a note of incredulity in her voice.

Scott went an even deeper shade of red, and struggled to his feet. Turning his back on the van, he started to stumble on again. These were exactly the type of women he fantasied about in his dreams, but not like this. He'd even had fantasies about being dominated by such women, giving them just the right measure of control over him for it to feel sexy, but always subconsciously allowing him a way out. This - on the other hand - was an altogether different level of realism, and one that he was having severe difficulties with processing. There was no secret sense of control here that he could exert now that things had gone too far, not like in his dreams. There was no waking up from this. No, here he was as Sailor Moon and there was no way of escaping that reality.

Behind him, the woman called out again, and he could hear the van slowly edging forward, matching his pace.

"Did you hear me, what the fuck are you dressed as?"

Scott considered ignoring her. If he just walked on surely the velvet bag with his wallet, keys and phone couldn't be too much further. Instead though, he heard himself reply, without even realising ahead of time what words would come out of his mouth.

"Sailor Moon." he mumbled, quietly.

"Sorry, what?" the reply came.

"Sailor Moon!" Scott said, louder, through gritted teeth.

The woman pulled her head back into the van and conferred with her friends for a few seconds.

"Well, 'Sailor Moon' - why don't you jump in and all us "girls" can have a chat." There was mischief in that voice, Scott could sense that even through the fog that was otherwise clouding his mind.

He waved his hand forward, trying to get the girls to drive on now that they'd had their fun. However, they didn't yet seem to have had their fill of "fun".

"Come on," another woman's voice interjected, "we've never been with a sailor before..." There was a distinct edge of mocking to her voice and Scott waved his hand on even more urgently.

There was a honk of the horn that made Scott jump slightly, and as his skirt bounced around again flashing glimpses of his pink panties, this elicited another round of laughter.

Then, a sudden moment of hope. As Scott broke into a trot, he spotted a distinctive velvet bag only a dozen feet away. His keys, wallet and phone were now blessedly within reach. He tried to break into a run, but his unfamiliarity with running in heeled boots made him look even more ridiculous, and the girls behind him were clearly have a great time.

Scott was beyond caring at this point though, and when he reached the velvet bag he gave a small cry of victory. The cry of victory died on his lips when the thought that maybe Master could have thrown an _empty_ bag on to the grassy bank - just to mess with him further - crossed his mind. However a quick inspection of the bags contents managed to squash his worst fears and he clasped his keys in trembling hands, as if they were a medicine that would cure him of a strange, exotic and entirely fatal poison he'd just ingested.

Behind him, the girls in the van had similarly stopped and there rude suggestions had temporarily been put on hold as curiosity about what Scott was holding got the better of them.

Three of the women hopped out of the van, and as Scott turned to start back towards his car, he realised too late that he'd been surrounded.

"What do you want?" he asked sullenly, eyeing the women suspiciously as the three of them slowly converged from all directions.

"What exactly is going on here?" the blonde-haired beauty said, her eyes slowly taking in Scott's full outfit and - he noticed uncomfortably - his face.

"I just... I just need to get back to my car, okay?" Scott mumbled, his voice breaking through a thick layer of embarrassment. One of the women suddenly pointed at his crotch, and gave a muted laugh, before nudging one of her companions and whispering something in her ear. Whatever was whispered was enough to cause another outbreak of laughter and pointing.

Scott looked down, stricken, and then swore under his breath. His manhood was now erect and pointing out under his skirt, and his arousal was obvious to his audience.

"Tell you what," one of the women said - a brunette who was also strikingly attractive - "we'll take you back to you car ourselves! We just want one... small... photo..." she said, teasingly. She pulled her phone out of her pocket and waved it about invitingly.

Scott shook his head vigorously. "No way. I'm going." He started to walk off, but the women had him surrounded.

"Come on. Just one, tiny photo."

Scott shook his head a second time, but a blaze of horns from another couple of cars that passed by caused him to stop for a moment and consider his options.

Finally, he looked up at the brunette. "I get to cover my face." he said, trying to sound like he was in a strong position to negotiate.

All three women laughed, but after a short conversation among themselves, the blonde replied. "You can hold one hand and one hand only over your face. And it's only a little photo, so we get to decide what else is in the photo. And," she added, with the air of someone being extraordinarily generous, "when we're finished we'll drive you back to your car. We assume it's close by?"

Scott nodded, and pointed back down the road. "Probably only a minute's drive that way."

"Pity," the woman replied, with a naughty look on her face, "still, better than walking back, right?"

Scott groaned, and looked up and down the road. Traffic was getting busier and busier. If he had to walk all the way back, who knew who else he would be caught by?

"Okay, okay, fine." Scott said, hurriedly. "One photo, I cover my face with one hand, then you drive me back immediately, no other problems, right?"

The blonde laughed, and the brunette reached out a hand to shake Scott's. "Deal!" she said.

The third woman in the group, a buxom red-head, hurriedly went back to the van and promptly returned with another three women. The group quickly setup around an increasingly nervous Scott, who was positioned ceremoniously the middle of the line-up.

"Now, who are we going to get to take the photo?" the brunette mused. "Maybe we should ask someone to stop?"

"NO!" Scott practically shouted, causing the entire group to break out in fits of laughter again.

"Please," Scott pleaded, "let's get this done quickly! Please!"

The brunette shook her head, but then paused and gave Scott an exasperated look. "Oh, fine!" she said, "Stop being a little cry baby!" She took a few steps back and beckoned for the group to shuffle in. "Come on ladies, and I need you two on the end to move to your left slightly... yes... yes, that's good."

She lined up the shot, and Scott covered as much of his face as he could with only one hand. Just as he thought she was going to take the pic though, she peered from around the device again and smiled. "Now, speaking of being a _little_ cry baby, we did agree that we'd be the judges of what else would be in the photo."

Scott's heart sank, what did she mean by that? He wasn't left to wonder for long. The blonde was next to him on his left, and without even asking she reached down and pulled his pink lacy panties down, and lifted his frilly blue skirt up. Scott yelped at the invasion, but with the camera pointed at him, he dared not lower the hand over his face, and his second hand was suddenly grasped by the red-head on his right.

"Oh my God," the red-head gasped, "it's so small!" Her voice trailed off into shocked delight.

Scott looked at her indignantly. "It is _not_ small!" he hissed between clenched teeth.

The blonde peered down now and nodded her head. "Sorry sailor, but she's right! Our Sorority has seen plenty of cock before, and _that_ is well and truly on the small side."

Scott continued to protest, but their brunette photographer was now calling for everyone to get ready. The women moved in even closer, as the brunette loudly mentioned that she was going to have to zoom in to get any sign of Scott's cock in the photo, so everyone was going to have to scrunch in a little more. Scott hid his face behind one hand and seethed to himself at the indignity.

"Okay ladies - this one's for the Sorority's Facebook page! So everyone say 'tiny pecker!'"

Scott's eyes flew wide open at the mention of Facebook, but he was far too far down the rabbit hole now. Even as he began to issue some protests though, the five other women around him cried out "tiny pecker!" and smiled and pointed at Scott's exposed manhood, peeking out over girly pink panties and underneath a frilly blue skirt.

The familiar noise of the camera's whirring was loud and clear over even the background noise of a motorway, and Scott shrunk back as he realised what had just happened. A sorority house now had a picture of him, cock out, in a Sailor Moon outfit, and with only a hand over his face. Fuck, fuck, fuck!

As the blonde let go off his panties and the red-head let go of his hand, he quickly pulled his panties up and pushed down his skirt. He looked accusingly at the brunette, who merely laughed and showed the photo to her companions.

"Come on sailor," the blonde said, slapping on his backside, "a deal's a deal - let's get you back to port!"

And with that, Scott was bundled into the van. Moments later, the van spun around and started heading back towards his car, cruising along in the steady flow of traffic. It was only as his car hovered into view in the rest area, that Scott realised he'd made yet another mistake. The sorority had previously only had one photo of him, hand over his face, in a silly, girly costume and with an embarrassed erection on full display. No name, no truly identifying features.

As the van pulled up behind his car though, he couldn't help but notice the blonde driver nod her head at his car's license plate, turn back to Scott, and give him a wink. Scott groaned, as he wondered where that might lead him to in the months to come...

****

The cafe was humming along with the usual midday business as Scott took a seat and nervously waited for his coffee to arrive. It had been three days since that fateful session by the motorway, and the email instructing him to be here had arrived this morning and had specified nothing else. He was dressed in normal clothes, black slacks and a plain blue shirt that meant he blended into the background. When he'd opened the email this morning and saw the word cafe, his mouth had gone dry at the prospect of being made to go into a public place in an outfit of his Master's choosing, but after several scans through, he'd realised that the communication held no such expectations. He was free to wear whatever he wanted, and what he wanted was to blend into the background. He'd had more than enough of being exhibited recently. He'd half-wondered if this was a test and he should turn up anyway in one of his costumes, to show Master that he was serious, but he couldn't force himself to do that without any threat hanging over his head.

Instead he waited, keeping to himself on his table for two, and keeping a cautious eye on everyone who came through the door. He was expecting Master to turn up, and several minutes passed and his coffee arrived while there was still no sign of the stranger who had put him through the wringer. Well, that Scott had _allowed_ to put him through the wringer, he thought darkly to himself.

He was sipping the drink and keeping a careful watch on the door at the expense of paying attention to anything else, so it was only when the man was practically reaching for the other chair to sit down at his table that Scott realised someone else was joining him.

Scott sat back with a startled expression on his face, but said nothing. The stranger was an african american man, likely of a similar age to Scott, and with short, neatly trimmed black hair. He wore a faintly amused expression, and didn't say anything for a few seconds, simply taking in Scott's surprised look.

"Umm..." Scott started to say. Oh God, was this another situation like the one with Robert? Was this going to be another contest? Memories of jerking Robert off with a desperate hand-job arrived unbidden at the forefront of his mind.

The other man just laughed at Scott's obvious confusion and nervousness. "Today, you will call me Jonathan, and you will not be giving me a hand job." he said, with a smile.

Scott blushed, and looked around at the other tables, wondering if anyone else had heard. One or two heads seem to turn slightly towards them, but then they returned back to their own conversations. Scott waved a hand up and down, trying to tell this new stranger to keep his voice down.

"I was expecting..." Scott started to say, before Jonathan smoothly interrupted. "You were expecting Master. He is busy though. My name is Jonathan. I am like you in some respects, although I have been you for far longer." An amused twinkle in his eye caused Scott to blush again. Jonathan reached into a small bag that Scott only now just noticed he was wearing, and retrieved a small package, placing it directly between the two men.

"I have a gift and two instructions." Jonathan said, and then leaned back in his chair and interconnected his fingers in a relaxed pose.

Scott looked down at the box suspiciously. Costume? If so, it was a small one. Could be a yet another pair of bra and panties - hopefully that wasn't the _entire_ outfit!

"So, I should.. umm... you know... wear this at some event later?" he asked, cautiously.

Jonathan shook his head and then paused to reconsider. "Well, actually, you're not _entirely_ wrong. You will be wearing this at an event later." Jonathan gave him yet another amused look and Scott began to wish he wouldn't do that. "However, my first instruction is actually that you should put it on now." Jonathan looked over his shoulder and indicated a small door near where the orders were made. "You can go change in the bathroom. Don't dawdle though."

Scott's heart suddenly began to race. So Master had let him come to this cafe dressed like a normal, respectable adult male, just so he could have his hopes of getting out of this place with his dignity intact instead ripped away in one spine-chilling revelation?

"What about..." Scott said, it a high-pitched, pleading tone, and looked down at the regular clothes he was wearing.

Jonathan laughed. It was neither a warm nor an overly harsh laugh, just the laugh of someone in on a joke that the rest of the audience wasn't privy too yet. "Just go put this gift on. It's your decision as to what you do with the rest of your clothes."

Scott frowned and looked confused. Okay, so it was lingerie that he had to wear under this other clothes. He knew the lingerie would be used to embarrass him soon enough, but at least he may get out of this cafe without too much humiliation.