The Pitch
“How’d you like to attend a “Halloween” Costume Con in San Francisco, my treat?” Maggie texted him.
“What do you mean by my treat?” Phil asked.
“I make the reservations, register you for the Convention, plan out the meals. You just have to drive down and park," she answered back.
“Sounds delightful, when is it?” he replied.
“Last Weekend in October,” was her prompt response.
Checking his calendar he replied back “I can make that work, all I do is drive down and park?”
She added, “Well you do have to wear any costumes I might provide for you.”
“I’d do that anyway,” he added a smile emoji.
“So you agree? I pay for the Convention. You drive down and wear the costumes,” she confirmed.
“Sounds like a good deal to me, I would love to go,” he confirmed.
The last weekend in October.
Phil packed his overnight bag and his big suitcase full of costumes and loaded up his car. She had given him the hotel's address in the city and directions to their basement parking garage. All he had to do was park and ride the elevator up to their room, Maggie already had his spare key and had checked in herself.
The drive down was a tad boring but fighting his way through SF traffic was always “fun”. He pulled a ticket stub from the vending machine and parked under the hotel. He was neither far nor close to the elevators, luckily his luggage had wheels. He entered the elevator and pressed for the tenth floor. It stopped at the lobby and let a couple with luggage on, they got off on the 5th floor. He couldn’t help but notice the young lady had been wearing a very tight and short leather skirt. Seamed stockings and very high, very shiny heels. He had tried not to stare too much but he had always enjoyed the look of leather. Her white silk blouse was just see through enough to reveal a hint of the black lacy bra she was wearing underneath.
He was sad to see them go on the fifth floor, but did delight in the view of her hips swaying down the hallway before the doors shut and he was once again headed upstairs. He whistled along with the music on the elevator speakers as he continued to the tenth floor. The ding of the arriving elevator snapped him out of a mental fantasy he had been having about the young lady in the skirt. Thankfully when the doors opened no one was waiting. Reading the chart on the wall he turned left to look for their room.
He soon found 1078 and knocked on the door. Maggie let him in and helped him stash his suitcase in the hotel closet. They exchanged a warm and long hug.
“So when does the Convention start?” he asked her.
“Tonight is a big opening ceremony and dinner, then the rest of the Convention opens to the attendees after that," she answered.
She continued “I was hoping we could just eat in the room and skip the gala, then attend some of the after dinner events.”
“Sure, that sounds more relaxing than getting all dressed up for a rubber chicken dinner” he agreed.
“You look through the room service menu and we’ll order up," she told him.
Phil dug around the small hotel desk until he found the hotel menu, they both wound up ordering burgers and fries and drinks. The kitchen indicated it would be an hour till it arrived.
Settling on the bed comfortably they turned on the television and found a movie to watch till it arrived. The waiter brought the serving table into the room and set it up, uncovering the burgers as if they were a rare meal deserving of the finest china and silverware. Although tasty and warm they were undoubtedly just burgers.
He pushed the tray and the dirty plates out into the hall for pickup by staff.
“So now what?” he asked her.
“Now you go use the bathroom and take a nice hot shower while I lay out your first costume for the night," she told him.
He jumped up and headed to the restroom “A surprise, I love it!”
He didn’t hear Maggie mumble “Maybe” Then louder she told him “Make sure you shave!”
20 minutes or so later he exited the bathroom still slightly damp from a hot shower with a towel wrapped around his waist.
“So where’s my costume?” he asked looking around the room.
“First we have to get you ready for the costume,” she answered.
“So what’s first?” he asked, still excited by the whole idea.
“Something I know you’ve always wanted to try, come over here and close your eyes," she told him.
He did as she asked, he heard one of the hotel dresser drawers slide open. She tugged the towel off his waist and wrapped something around him. He suspected what it was but waited till it was fastened and she was tugging on the laces in back.
He couldn’t help himself and opened his eyes, it was indeed a corset. “A corset? How fun!” he exclaimed.
It was a basic black one, clasps in front and he assumed lacing in the back, it covered him from hips up to nips so to speak. He could feel it closing around his waist as she tugged harder on the lacing. He exhaled as hard as he could, letting all the air out of his lungs. She took advantage of the moment and pulled a lot of slack out of the lacing. As he went to replace the air he realized he really couldn’t inflate his chest and was forced to take small sips of air.
“Okay?” she asked him.
“So far” he replied a tad breathless, while wondering silently how women wore these things daily.
“I’ve almost got it closed,” she told him. “Think you could do that one more time?”
“Sure, ready?” he responded.
“Go” she said as she grabbed a handful of lacing.
He exhaled as hard as he could again and held it for a few seconds as she tugged the lacing ever tighter. This time when he had to breath, he was nearly panting with the effort to get enough air in his lungs.
“You’ll get used to it.” Maggie told him “But look at your shape now," she spun him around to look in the mirror.
Phil did indeed now have an actual waistline and hips. Some of his pectoral muscle was even being squished upward making a hint of cleavage. He doubted anyone would mistake him for a woman, but he had to admit he did not look completely male at this point either. Well besides his rather obvious cock hanging below the corset.
“Can you sit on the bed?” she asked him.
Carefully he backed up to the bed and attempted to sit. It was a whole new experience in a tight laced corset, nothing bent from the hips up. He managed to bend enough to get his butt on the edge of the bed.
“Sorta,” he said when he finished.
“Okay well just stay there for a few minutes while I get your stockings and shoes on," she ordered him.
She dug in the dresser drawer and pulled out black seamed stockings and a classic pair of black heels. He gave a little chuckle remembering the young lady he had admired from the elevator earlier. Apparently he was to be given a similar treatment. Bending down at his feet he felt her lift his right foot and slip the nylons on him. Then slowly and carefully tug them up his legs. She repeated the process with his left leg, both of them ended just about mid thigh or a little higher. She added garter belts from the lower edge of the corset to the tops of the nylons and cinched them tight.
“Whoops, almost forgot, these would have been difficult to put on over the shoes.” She dug in the drawer again and returned with a bright pink pair of ruffled latex panties. She pulled the underwear into place tucking his manhood down and under.
She told him “You wear the underwear over the garter belts, so you can pull down your underwear to pee without unhooking everything.”
Next she produced a set of shiny black high heels and helped slip them on his feet. She was doing something to them, when he heard a clicking noise. As he held up the foot she had been playing with, he noticed a series of straps that went around his ankle and then under the instep of the high heel and judging by the two padlocks he saw, locked in place. While he had been looking at his right ankle, she had locked his left heel in place with a matching set of straps and locks.
“Can you stand?” she asked him.
He managed to push off the bed and stand in the heels. “Yes. But I’m surprised by this costume. I thought you preferred a more manly look?”
“True,” she took a moment to answer, “but I bought a specific costume for a specific event I know you’ll like and this is all a side effect of that.”
“Okay” he tottered around the room in his heels a bit “So where’s the costume?”
“I don’t want you peeking so I have another item to make sure you don’t” she dug in the drawer and pulled out a black leather hood with a built-in gag, blindfold, and lacing up the back.
He obediently tottered back to the bed and sat down on the edge again so she could more easily reach his head. She slipped it on and he let the gag fill his mouth. She worked the lacing in back and he felt it shaping itself to his skull, with just a hint of pressure all over and the gag seating itself a little deeper in his mouth. When she had it as tight as it would go he felt her buckle a collar around his neck and over the lacing. The distinct sound of a small padlock clicking closed informed him he would not be removing it.
“Can you still hear me Pet?” she asked a little loudly.
“Mph,” he replied but also nodded his head yes.
“You might have noticed this is a new hood?”
Again he nodded yes.
“It has a built in locking collar and several d-ring attachment points the other one lacked,” she told him, while tugging on a few of the d-rings. There was one at his throat, one on top of his head, and one over each ear.
“All the better to control you," she added after the demo.
He felt his own head with both hands, confirming the locked collar and the various d-rings locations.
“Almost forgot those pesky fingers of your’s, Pet," he heard her say. “Hold your hands out in front of you," she ordered.
He felt her slide a leather mitt over his right hand first and he obliged her by curling his hand into a fist inside the mitt. The zipper closed and he felt her tighten a buckle over the zip and tight around his wrist. Again the sound of a lock closing confirmed he wouldn’t be removing it. She repeated her actions with his left hand, again the sound of a lock closing sealed his hand away.
“So now you can’t peek and you can’t feel what the costume is," she announced, sounding satisfied.
“But one more, or should I say two more, finishing touches.” He felt her put something cold against his chest and slide part of it into the cups of the corset. “Let me get this centered properly…” she was re-arranging it slightly when he felt her squeeze it oddly and he felt the item “suck” in his nipple via a vacuum effect. She repeated the process with his other nipple. It was an odd sensation but the squishy material soon warmed up.
“Now you’ll fill out your costume like a proper woman.” She commented. He nodded in agreement, wondering where all this prep was going.
“TIme for the costume, please stand up," she told him.
He did so and felt her moving around him and pulling something over his head. She tugged it down over his torso and adjusted it here and there. He felt her pulling a zipper up in back. It was tight across his shoulders and he could feel some sort of short sleeve. When she had it fully zipped up he heard an odd click, similar to the locks he had heard earlier.
He “mphhed?” a questioning sound.
“Yes, that was a lock. This costume comes equipped with a locking zipper," she answered the implied question.
“Mpphh?” he grunted again.
“Why? Because not everyone voluntarily wears such a costume and some Pets might be tempted to remove it given the chance," she answered again.
“Mpphh?” his grunts sounding desperate even to his own ears.
“All your questions will be answered in a moment my Pet. Be patient," she told him as she fussed with some part of the outfit around his waist.
He felt her removing the blindfold attachment from the hood. He turned until he could see himself in the hotel mirror. She had dressed him in a black PVC French maid costume. A puffy short skirt, the white apron tied tightly around his corseted waist. Lace cuffs over the leather mitts.
“Mppphhh?!” he asked her.
“Why?” she guessed his question “Because I know how much fun you had being my maid before and I wasn’t completely honest with you about what kind of costume convention this is. You see, it's a fetish event.”
Maggie ignored his surprised mph and helped him to sit back on the bed again.
“With the hood locked on, no one will know who you are and we can enjoy the event," she filled him in on her plan. “So tonight you are my loyal maid Fifi. Helping me shop in the dealers room and maybe being used for demos. Well, let's be honest, you will be used for demos.”
“There’s only one problem, the hotel has asked attendees not to wander the halls in fetish gear and scare the other guests. So we need to get you from here to the convention spaces unseen and since I’ve locked most of that costume on and I don’t have the keys here," she smiled at him. “I have a plan.”
He gave a quiet “Mph?” and relaxed as best he could on the edge of the bed.
Her Plan
“So do you recall me telling you in the past I have a friend who designs and sells kinky accessories and clothes?” she asked him while she typed away on her phone, texting someone.
He nodded yes and gave an affirmative “Mph”.
“Well that’s how I got us tickets for this event, she is a vendor here this weekend,” she told him excitedly.
Phil waited patiently for the rest of the plan.
“Well I just texted her and she is all done setting up her booth on the dealers floor.” She seemed overly happy by this news, he wondered what this meant for him?
“She and her crew are coming up here with their personal luggage cart and we can load you up and wheel you through the public spaces until we get to the dealers room!”
“Now I get it,” he thought to himself, the big plan was to treat him like luggage. It was probably a good thing he was still gagged, so he didn’t say anything foolish. Instead he just nodded his head yes, to indicate he understood.
They sat silently together while they waited for a knock on the door. Phil tried to get used to the shallow breaths the corset demanded of him and the odd sensation of having “breasts” attached to his chest.
“Oh I almost forgot,” she suddenly blurted out. “The keys to your outfit and accessories, my friend shared them with the rest of the vendors downstairs. We’ll have to visit every booth and ask very nicely for their key until we collect them all.”
Phil stared at his friend, then shook his padlocked mitted hands at her, he “mpphed mpphed” angrily at her.
“You can be mad at me, but I recommend you take a more pleasant tone," she warned him “Someone will have to walk you around to those vendors and someone will have to be able to ask them for the keys!”
He quieted down immediately and held up his mitted hands in a gesture of surrender.
“That’s better,” she told him and bounced off the bed to go sit on the sofa. “I expect my maid to be well behaved at all times.”
She had only sat down for a few minutes when a strong knock came from the door to the hotel room.
She bounced up, all smiles to answer the door. He heard it open and she said “Gloria, please come in!”
“Meet Fifi, my personal maid," she waved at Phil on the bed. “Fifi, meet Gloria and her friends…”
Gloria introduced the others “This is Susan and Mark, they are helping me staff my booth this weekend.”
Susan was a painfully skinny young “goth” girl in a black dress reminiscent of Morticia Adams, while Mark was more casual in a pair of leather pants and a red polo shirt with a small logo on the chest. Phil assumed it was Gloria’s shop logo.
Gloria herself while slightly older, Phil guessed late 40’s maybe early 50’s, must have been some sort of pinup model in her youth. She had an hourglass figure and was wearing a tight leather pencil skirt and a wrap front white silk blouse that highlighted her figure. Phil felt compelled to stand up and curtsy as best he could to Gloria and her friends.
“Well aren’t you the well trained maid Fifi.” Gloria smiled at Phil.
Phil sat back down, not quite trusting himself in the locked on heels yet and honestly winded from just standing and curtsying. He was still not used to the corset obviously.
Susan and Mark had wheeled in a large object covered with a shiny curtain of some kind of material, Phil suspected spandex. It was as tall as the doorway and obviously on wheels but not as wide or as long as he would have expected when he heard the term luggage cart. It looked a lot like a skinny, tall phone booth on wheels Phil thought to himself.
Gloria waited till they had it in the center of the room before she pulled the curtain off of it and yelled “Tah dah!”
It was not a luggage cart, it was an upright barred cage!
It looked suspiciously like a magician's prop. Maggie whistled a long slow note. “Well isn’t that impressive!” she finally remarked out loud.
“How does it open?” she asked her friend Gloria. Gloria reached over and undid several small hasps on one corner edge and an entire section of bars swung on silent hinges. The entire backside opened giving you full access to the interior space.
Gloria turned to look at Fifi expectantly. “Well, let's see if she fits.”
Fifi rather reluctantly stood up and tottered over to the cage, reaching out with mitted hands to brace themselves as they stepped up onto the platform and into the cage. There was no clear front, back or sides, all sides were roughly the same size so Phil just stepped up and pressed himself against the “front” bars. His shoulders were touching both sides and he felt the cage door shut and it pressed against his ass.
It was definitely a squeeze for Phil as Fifi, and he knew not to complain as he heard those small hasps shutting and the sound of padlocks locking the door shut.
He heard Gloria remark “Well it’s a tight fit, but we should be able to smuggle Fifi downstairs in there.”
His friend said “Okay, let’s go party people!”
Susan and Mark, between them, managed to put the curtain back in place around the cage, so Phil was hidden from view. Then he felt them pushing and pulling the now heavily loaded cage over the carpeted floor and out into the hotel hallway. The hallway carpet had less of a nape and the cage rolled easier once they crossed the threshold. They rapidly wheeled the caged Fifi to the elevators.
Maggie stage whispered to Phil “You okay in there Fifi?”
Fifi grunted affirmatively.
Special Delivery
Inside the curtain Fifi heard the elevator doors ding as they arrived on the tenth floor.
They wheeled the cage onto the elevator and he heard the doors shut behind them. Unexpectedly Fifi felt a hand reaching up and under her skirt, due to the restrictions of the cage Fifi couldn’t really stop them or see who the hand belonged to. But someone found his manhood and they started fondling him. Fifi enjoyed the attention and it made a boring elevator ride much more exciting. He heard the ding of the elevator announcing arrival at a floor and the hand let him go and disappeared.
“Just need to cross the lobby floor and enter the big ballroom where the dealers are set up” Gloria remarked in a louder than necessary voice, as if she had just been talking to the people in the elevator, so Fifi could hear through the hood.
His friend Maggie stage whispered again “Best not make any noise Fifi!”
Fifi felt the cage moving backwards off the elevator and then they continued to wheel it through a noisy room. Everyone must be checking in for the convention, Fifi thought. Suddenly there was a bit of a commotion just outside the curtain.
Fifi heard raised voices, they sounded happy. Greetings were exchanged and he heard Gloria explaining how she was a vendor at the event and then a voice he didn’t know asked something he didn’t quite catch.
But then clearly he heard Gloria say “Oh this? This is just some stock we forgot in the room, we are moving to the booth.”
The new voice suddenly said clearly “New Stock? Let me peek!” and Fifi was suddenly looking out the bars at a new person who was just as surprised to be looking at Fifi, as Fifi was to be seeing them. This new person’s eyes popped open and their mouth formed an “O” of surprise, when the curtain was quickly pulled back in place.
“No sneak peeks dear!” Gloria said firmly. “Susan, Mark, get this to the booth. Now.”
Fifi heard the new person's voice say “Well if that’s for sale, I’ll be checking out your booth later.”
Suddenly the cage was being wheeled away quite rapidly and Fifi hoped they didn’t crash into something or fall over, that would be embarrassing.
The Dealers Room
Fifi thought there was a change in the feeling of the cage and how it was rolling over the floor. There was less noise wherever they were currently. Mark and Susan whirled the cage around and Fifi soon lost track of the turns taken. Eventually it stopped, then there were some minor adjustments, some wiggling back and forth. Whoever it was, must have eventually been satisfied with their efforts, because the cage was left alone.
“You okay in there Fifi?” his friend Maggie’s stage whisper asked.
Fifi grunted around the gag loudly twice, that was their “yes” signal. One grunt or silence would have been a “no”.
Maggie continued in her overly loud whisper “There’s some people setting up their booths nearby, as soon as they wander off we’ll let you out.”
Fifi shifted her heeled feet and tried to get comfortable inside the cage. Of course this was nearly impossible considering the tight fit. This cage was more for someone petite, Fifi was extra large and extra tall on a good day. Add heels and Fifi’s head was touching the top of the cage. Normally Phil was quite happy to be a large man, but as Fifi it was a tight squeeze. Fifi waited as patiently as possible considering the situation.
After what seemed to be hours later, the curtain was opened and someone was unlocking the small padlocks locking the cage shut. Before opening the door though, whoever was back there took the opportunity to fondle Fifi’s ass.
“Those heels really make your legs and ass pop Fifi” he heard Gloria comment.
“Well at least I know who is fondling my ass.” Fifi thought to herself.
“Okay hop out of the cage Fifi” Gloria helped her out of the cage. Fifi stumbled a little as she stepped down from the cage and leaned on Gloria more than she intended.
Gloria said “Careful now, don’t snap a heel or sprain an ankle.”
“Now bend over and let’s get that gag out of your pretty little mouth Fifi,” Gloria ordered.
Fifi bent forward and Gloria undid the buckle holding the gag in place. That still left the leather hood and locked-on collar in place, but now Fifi could talk.
Gloria added, “After all you’ll need that mouth to beg for keys.”
“Oui Oui Madame,” Fifi said in an exaggerated accent.
Gloria hooked a finger through the d-ring on Fifi’s collar and pulled down “I might have to borrow such an obedient maid for myself, later Fifi.”
“Of course Madame.” Fifi curtsied. “Now what Madame?”
His friend Maggie chose that moment to reappear behind Gloria.
“Well Gloria already handed out the keys to unlock your outfit to her various friends here in the dealers room.” Maggie told Fifi.
“Gloria, may I borrow a leash? Fifi needs to be taken walkies.” Maggie asked her friend.
Gloria rummaged under her counter and came up with a leather dog leash with a snap clip end. She snapped it on Fifi’s collar and then handed the other end to Maggie.
Gloria told Maggie “Have fun, there are over 30 vendor tables and there are only 7 keys. Good luck finding them!”
The first quest
Maggie pulled Fifi out of Gloria’s booth and led her to the booth next door, where the staff were putting their stock out on the tabletops.
“Hello.” Maggie called out “Whose booth is this?”
A middle aged woman stood up and said “Me, what can I do for you?”
Maggie continued “Do you happen to have one of Fifi’s keys?”
“Fifi’s keys?” she asked, apparently confused.
“It’s a long story.” Maggie said.
“I’m almost done, the others can finish it up,” she sat down in a chair and waved Maggie to an empty chair nearby. “I’m Sally, tell me a long story.”
Maggie sat down and Fifi stood behind her chair, still on the leash.
“Well you may have noticed that Fifi is locked in her costume….” Maggie started and then told a condensed version of Fetish Fifi and the quest for the keys as Sally nodded along and asked questions.
“So what will Fifi do to earn these keys from the vendors?” Sally asked when Maggie finished.
“Do?” Maggie asked “Earn?”
Sally pointed at Fifi. “Well the Vendors are doing Fifi a favor, i think they will probably want a favor in return.”
Maggie commented “I never thought of that, but you are probably right. Fifi would owe the person who held the key a favor of some kind.”
Sally smiled and stood up “I’m glad you agree,” Sally held out her hand expectantly.
Maggie handed the end of the leash to Sally. Sally handed Maggie a key.
“Come back in 30 minutes.” Sally waved at Maggie who reluctantly left the booth.
“Well Fifi, let’s see how useful you can be for 30 minutes.” Sally tugged the leash and led Fifi deeper into the booth and behind a curtain in back.
Sally dug around in some plastic tubs looking for something. “I don’t know if you noticed my wares on the tables Fifi”
Fifi had to admit, “No Madame, what do you sell here?”
Sally smiled at Fifi “We sell floggers, paddles, and other impact toys.” Sally found what she was looking for and held it up for Fifi.
It was a sash reading “Spank Me, it’s the only way I’ll learn.” on the front, and on the back was a small logo and the words “Follow me to Sally’s paddles”.
“Now you’ll wear this,” Sally put the sash over Fifi’s head, “we’ll see if we can’t drum up some business and maybe find some of your keys.”
The second quest
Sally pulled Fifi by the leash and headed to the booth next in line. “Hey, Heather,” she called out.
A 30 something latino woman emerged from behind a curtain and waved “Hi Sally, who is your friend?”
“This is Fifi, a friend of Gloria’s, and my current display model,” Sally told her.
“Display model?” Heather seemed to perk up at those words.
Sally had a small briefcase and opened it for Heather “The latest version of my crops, paddles and floggers.”
“Fifi, bend over this table.” Sally ordered her, then told Heather, “I only have her for 30 minutes.”
Heather picked something up out of the case and stood behind Fifi. “Ready?”
Fifi said “Oui Oui Madame,” and gritted her teeth in anticipation.
She felt someone lift her skirt and rub her ass “Nice latex panties Fifi,” then suddenly something struck her ass.
“Mph,” Fifi let a small grunt escape her gritted teeth.
Heather commented to Sally “Nice handle, good speed, and solid impact.”
Another swing and Fifi felt a strike on her other ass cheek. Another small grunt escaped her lips.
Heather leaned down over Fifi’s back and whispered in her ear, “I’m going to keep cropping your ass until you stop making noises.”
Heather stood back up and said to Sally “You see that’s the problem with latex underwear, zero protection against impacts.”
“Right Fifi?” Heather asked right before using the crop again. Knowing it was coming, let Fifi fight the urge to grunt in response.
“Very good Fifi, I didn’t hear a peep from you that time.” Heather complimented her. “As promised no more croppings, hand me that new paddle Sally?”
Fifi couldn’t help but turn her head to try and see this new paddle.
Sally tsked at Fifi. “No peeking, you know your owner gave me the gag and blindfold attachments for that hood.”
Sally tossed the leash over the table Fifi was leaning on and moved around to that side. She stepped on the leash and pulled Fifi’s head down even lower. She inserted the gag and buckled it in place tightly, then attached the blindfold using the push snaps to attach it to the hood.
“Go ahead Heather, give it a test drive now.” Sally told Heather
“Five a side, Sally?” Heather said out loud.
“Sounds about right,” Sally told her.
Fifi whimpered around the gag right before Heather landed the first blow on her right cheek. Then one on the left, then back and forth until there had been five a side. When Heather finished she rubbed Fifi’s ass gently.
“Well you’ve earned your key Fifi” Heather said and pulled the waistband of her underwear out and slipped the key into the latex panties.
“How much time do you still have Sally?” Heather asked as she pulled Fifi’s skirt back down.
Sally stopped standing on Fifi’s leash and let her stand back up. “About 20 minutes now.”
“Time to strut Fifi.” Sally told Fifi and tugged on the leash leading her to the booth across the aisle from the current booth.
The third quest
Sally called out “Hi Neighbor” and for a change Fifi heard a male voice answer “Howdy, how can I help you?”
“This is Fifi, her owner has locked her in this costume and given the keys to various vendors here in the dealers room.” Sally explained. “Currently Fifi is working off a debt to me in exchange for one of those keys.”
Fifi heard the male voice, much closer now, ask “How is she earning these keys?”
“Well so far she’s helping me demonstrate my newest crops and paddles for the next 30 minutes. Heather, across the aisle there, decided to make her earn a key by paddling her.” Sally explained to the male voice.
The male voice, now behind Fifi, startled her with his comment “So Fifi is earning back the keys, one by one. Fascinating.”
“Yes, exactly. There’s one in her pretty pink panties right now.” Sally told him.
“Oh really” the male voice said and Fifi felt her skirt being lifted. “Such a shame they are ruffled, I was hoping to see the key.”
Sally commented, “Yes but they are pretty panties.”
“Yes, yes, very pretty,” the unknown male voice said, still behind Fifi, still lifting her skirt up. “Now about earning those keys back.”
“Well I still have her for about 15 more minutes,” Sally commented “If you’d like to try my newest crop or paddle?”
“How about we try out your paddle with my bondage furniture, I have a lovely padded paddling bench.” the voice said.
“Sounds like a great combo,” Sally was already dragging Fifi through the booth by the leash.
Fifi, still gagged and blindfolded, followed as best she could, occasionally bumping into unseen objects.
“Here we are, just have her lay down on top of this bar,” the male voice told Sally
Sally ordered Fifi “It’s directly in front of you, put your hands in front of you and bend at the waist Fifi.”
Fifi reached out and slowly bent over until she felt the bar with her mitted hands. Using her arms she eventually managed to lay down on the leather covered bar. Once she was in place she felt hands grabbing and positioning her ankles in position and another set of hands positioning her hands. She was fastened to the object at all four corners, and a hook of some kind attached to the d-ring of her collar keeping her head down.
The male voice said from somewhere near Fifi’s legs as he lifted her skirt “Hand me the crop.”
Fifi clenched her ass cheeks and bit down on the gag in her mouth, worried that the new male voice would be much harsher than the earlier croppings she had received.
The whistling sound of the crop being tested on the air was loud enough for Fifi to hear it even through the leather hood.
“This is going to sting,” Fifi thought silently.
The solid thwack sound of the crop hitting both of her ass cheeks at once confirmed Fifi’s fears. Fifi, even expecting it, let out a muffled howl of pain in reaction and tears filled her eyes instantly. She frantically pulled on her arms and tried to sit up to no avail, whatever straps were holding her to the paddling bench resisted all efforts to escape.
“Such a reaction! Magnificent,” Fifi heard the male voice remark. “I must ask her owner if I can use her for my demo tomorrow afternoon.”
Fifi whimpered, afraid his friend Maggie would indeed lend her for the demo.
“But..” and here the man paused and rubbed Fifi’s ass “…that was only one of ten.”
He took his time, pausing often in between blows from the crop to switch angles or sides. But overall Fifi’s bottom was on fire by the time he finished, not an inch was spared from blows from the riding crop.
“Well that’s ten Fifi, you’ve been an excellent test subject. Did you get that recorded on your phone?” the male voice asked.
Sally answered “Yes, it was marvelous. Her reactions, your swinging of the crop. If this doesn’t get a couple of thousand hits for your channel I’d be surprised.”
Fifi lay panting on the bench completely spent and aimlessly twisting in the bondage, still trying to get free somehow.
“How much time is left of your 15 minutes?” the still unknown male voice asked Sally.
“About 2 minutes, I’ll have to return her soon.” Sally replied.
The man was doing something to Fifi’s panties “You’ve earned your key from me Fifi,” and he slipped it into her underwear. “I hope to see you tomorrow afternoon.”
He then moved onto her ankles and undid the straps holding her feet in place. Fifi assumed Sally was doing the same to her wrists and freeing her mitted hands.
Gingerly and slowly Fifi leveraged herself upright and off the padded bench surface, she stood next to it using her otherwise useless hands to steady herself alongside the bench.
“Can you walk?” Sally asked from next to her.
Fifi nodded yes and stood fully upright. Sally pulled her skirt down and straightened the dress. Then taking the end of the leash slowly walked Fifi out of the bondage furniture booth and back across the aisle back to Gloria’s booth. Just in time to hand the end of the leash to Gloria and Maggie who were sitting in chairs and chatting away.
“I see the blindfold and gag are back in place. Was Fifi naughty?” Maggie asked Sally.
“Oh no, she’s very well behaved. We just didn’t need her to talk,” Sally answered Maggie.
“How many keys did Fifi recover?” Gloria interjected.
“The one I gave you of course,” Sally responded “And you’ll find two more in her pink panties.”
“In her panties?” Maggie sounded surprised “Well you’ve been having adventures tonight Fifi.”
“I need to get back to my own both, have fun getting the rest of your keys back Fifi!” Sally called out as she left.
Maggie stood up, lifted Fifi’s skirt and without comment pulled her panties down to search for the keys.
“Poor Fifi, your ass is bright red.” Maggie commented as she finally found the two keys. Then pulled the latex panties back into place.
“Well Gloria, do you want to take pity on Fifi and guide her to the next keys?” Maggie asked her friend.
Gloria’s response was not reassuring to Fifi “I thought we were going to make her hunt them down randomly?”
Maggie’s answer was firm “You know half these dealers disappear after their booths are set up. If we don’t get those keys now, Fifi will have to stay locked until the dealers room opens tomorrow. “
Fifi silently urged Gloria to volunteer to lead her around and get the rest of the keys tonight and not tomorrow.
“Very well!” Gloria huffed, as if put out by the task. “Give me her leash, I know just who to see first.”
The fourth quest
“Come along Fifi, your next key awaits,.” Gloria sang out as she tugged the leash. Fifi followed as best she could and wished someone would remove the blindfold.
After some twists and turns and general walking he heard Gloria greet someone “Mary, are you in there?”
“Gloria is that you?” a youngish sounding voice responded. “And who is that you are leading around?”
“This is Fifi, and she needs that key I left with you the other day,” Gloria cheerfully answered.
Mary chuckled loud enough for Fifi to hear. “So this is Fifi and she needs her key. Well. Well. Well.”
Gloria told Mary, “Make her earn the key.”
“Any limits?” Mary asked her.
“Well no permanent damage, no tattoos, no piercings, or that kind of thing.” Gloria told her.
Fifi silently thanked her for that.
“You know what I sell…” Mary trailed off suggestively.
“Yes, yes, I do,” Gloria agreed.
Suddenly Fifi really wished she knew what Mary sold at the booth.
“Set her up against the St Andrews cross Gloria.” Mary’s voice was different somehow, definitely more commanding.
Fifi felt herself being guided deeper into the booth.
“Turn around please,” Gloria told her.
Fifi spun around in place slowly and then felt Gloria pushed her backwards until she bumped into something solid.
“Raise your arms over your head” Gloria said and Fif felt her wrists being attached to something above and to the sides.
“Spread your legs wider.” The same process happened to her ankles.
Fifi had never been attached to a St Andrews cross but she had seen pictures of them. A giant X made of solid materials with attachment points for arms and legs at the ends of the cross’ arms. She tugged on the straps holding her wrists. There was a little wiggle room, but she wasn’t getting free on her own.
“Almost forget the most important part” Gloria commented as she ran a belt around Fifi’s waist that apparently attached to the middle of the X. Fifi wondered why a belly belt was so important.
“Ready to earn those keys Fifi?” Mary had returned.
Gloria wolf whistled “Nice costume Mary.”
“Thank you, it seemed appropriate for events.” Mary sounded pleased at the compliment.
“So you’ll want me to capture this session on my iPhone?” Gloria asked.
Mary agreed, “Absolutely, the best advertising there is.”
Fifi really wished she knew what Mary sold in her booth.
Fifi felt her skirt being lifted in front and tucked into the waist belt. Suddenly there was an odd sound, like a buzzing or a whirring. Fifi couldn’t place it, but suddenly she realized what it was as Mary applied a vibrator to her inner thigh and slowly moved it closer and closer to Fifi’s tucked away cock. Fifi arched her back and tugged on the straps, trying to escape the vibrations or maybe get closer to them. But it didn’t matter because the straps did their job and Fifi wasn’t going anywhere.
Mary plied the vibrator up and down Fifi’s legs and crotch, letting it rest on her balls until it was obvious the cocks shaft was inflating and pressing on the latex. Since only the rear side of the latex panties were ruffled and the fronts were not, it was very obvious the vibrator was having its intended effect.
“Do you like that slut?” Mary asked rhetorically “Does the sissy maid want to shoot her load?”
Fifi was panting around her gag and writhing in the straps, hips thrusting in mid air.
Mary put the vibrator down for a moment and pulled Fifi’s panties down, reached in and pulled her shaft out and then pulled the panties back up. The pink latex outlined her shaft in shiny detail and now that it was no longer tucked under, Fifi could really enjoy the vibrations. Mary expertly applied the vibrator and even through the latex it was driving Fifi crazy.
“That’s a really big cock for a French maid Fifi.” Mary said as she pressed the vibrator under his balls and held it there for a ten count. “Beg me to cum slut.”
Fifi grunted around the gag, she hoped it sounded like begging. While grunting desperately she continued to grind her hips forward, trying to get Mary to apply the vibrator to her cock long enough to make her cum.
Mary ran the vibrators head up and down Fifi’s shaft. “Cum for me Fifi, cum for me now!” she ordered.
Mary did something to the settings of the vibrator and it somehow increased in intensity. Fifi felt herself on the edge of exploding, she thrust her hips forward and was yelling “yes, yes, yes!” around the gag.
Mary laughed and lifted the vibrator off, Fifi was left with no stimulation and no way to cum. She yelled around the gag, “Nooooooooo!”
Mary laughed cruelly “Oh did you need something Fifi?”
Fifi grunted sadly and twisted her hips forward, desperately needing the stimulation to finish her off.
“Let’s shift into a lower gear and keep Fifi desperate for little bit longer viewers.” Mary was speaking to the iPhone camera Gloria was holding. She did things to the vibrator and it changed its tone.
Mary started running it all around, without touching Fifi’s shaft or balls. It was driving Fifi crazy, she had been so close to cumming just a few minutes earlier. Now the vibrations were slower and it was edging Fifi more than driving her to the brink.
Fifi was close to tears, steadily panting around the gag, her hips slowly twisting and thrusting.
“Please,” she mumbled around the gag “please”
Maybe Mary heard Fifi begging, maybe she just was tired of the game. But whatever the reason Mary adjusted the vibrator again to its highest setting and pressed it firmly against Fifi’s cock head.
“Okay Fifi this time cum for me quickly, before I get bored again.” Mary warned her.
Fifi’s eyes crossed and her mind was short circuiting. The vibrations were so intense. She was….cumming! She let her load go and filled the latex panties with cum.
Fifi hung from the St Andrew’s straps, breathing heavily around the gag. For some reason Mary was still holding the vibrator against Fifi’s cock and it was rapidly changing from pleasant stimulation to borderline torture.
Mary pushed up on Fifi’s forehead and asked “Had enough sissy?”
Fifi nodded her head yes, and tried to pull back from the vibrator. Mumbling around the gag she begged “Please…stop.”
“You were just begging me to turn it up Fifi” Mary kept pressing it to his balls, holding it in place. “Now you want me to stop?”
Fifi nodded yes, desperately, repeatedly.
Fifi wasn’t sure why Mary changed her mind, but just as suddenly as she started, she stopped.
“Did you get all that Gloria?” asked Mary loudly so Fifi could hear.
Gloria replied back just as loudly “Yes Mary, Fifi desperately begging and the explosive conclusion, then more begging.”
“Then I guess Fifi has earned her keys,” Mary pulled the waistband of the latex panties away from Fifi’s belly, “What a mess you made Fifi!” Mary let the waistband snap back and took a step away.
“Oh that was brilliant, fire up the camera, we’ve got to get that on tape. Maid, Made, hilarious.” Mary was laughing at her own joke.
“Recording!” Gloria told Mary.
Mary stepped back up to Fifi, slipped her fingers into the waistband, pulling the panties away from Fifi’s crotch. “Oh look Fifi has -made- a mess.” She hit the word made hard.
“But she has earned her keys.” Mary added, as she dropped a pair of keys into Fifi’s cum filled panties. Then rubbed her hand around on the outside, as if to smear the cum all over them.
Fifi wiggled helplessly, at her touch and grunted a questioning “Mph Mph?”
Mary took a guess “Yes, two keys Fifi. But that little performance will get me a massive number of hits on my website, so I think it's a fair trade.”
Gloria suddenly interjected “Okay and that’s a wrap. Are we good here Mary?”
“Yes, just email me the footage, you have my address.” Mary told Gloria, then reached out cupping Fifi’s cock and balls. “See you around the Convention, Fifi.”
Fifi felt someone undoing the ankle straps “Can you stand Fifi?” Gloria asked. Fifi grunted twice and nodded yes.
Gloria reached up and undid the wrist straps. Fifi sagged for a moment, but the waist belt helped and she regained her footing.
Gloria chuckled, “Told you that was the most important strap.” She undid it and Fifi stood on her own.
“Ready for the next key quest Fifi?” Gloria asked as she straightened out Fifi’s dress and apron again.
Fifi nodded yes slowly.
The Final Quest.
Fifi was more than a little sore, spent, and had a very sticky mess in her panties. But maybe this was almost over. If the last person also had two keys, this was the final quest. But considering what Mary had done to Fifi to earn her two keys, Fifi was more than a little worried about what the last quest might bring.
The leash led her out of Mary’s booth and she followed Gloria to the next stop. Again Fifi bumped into a few random things, but Gloria was good at guiding and they were moving relatively slowly.
Gloria remarked “You’ve been very popular, Fifi.”
Fifi grunted twice, a “yes”.
“Bet you’ll be happy to get out of that outfit?” Gloria continued.
Fifi thought about it, the heels were killing her toes and her corset had been slowly crushing her ribs all night. But the attention had been fun in many ways.
“No?” Gloria remarked as Fifi thought about the situation. “You kinky slut you.”
“Well then you are really going to enjoy this final quest.” Gloria told Fifi.
Fifi wished she had answered the question quicker, anything she grunted now could mean anything. She started walking a little slower, worried what this final quest could be. Gloria noticed immediately.
“You might not want to drag your feet, if they go home early you’ll be wearing that outfit all night and into tomorrow.” Gloria warned Fifi.
Fifi sped back up again. Suddenly less worried about the quest and more about being trapped for the night and morning.
“Good decision.” Gloria sped up too.
“There it is, Peter’s booth.” Gloria said as they stopped “Peter is going to adore you Fifi!”
She called out loudly “Peter are you still here?”
A male voice answered “Of course darling, where else would I be?”
“Peter, meet Fifi, Fifi this is Peter,” Gloria introduced them.
Fifi curtsied, Peter clapped his hands “Delightful!” he exclaimed.
Peter addressed Gloria, “She’s a big girl, but we can work with that. You want the works?”
Gloria answered Peter, “Yes her owner wants her ready for a party tonight. Here are the keys to this outfit.”
“Yes Fifi, I’ve always had two of the keys.” Gloria told Fifi, “Oh that reminds me Peter, Mary was quite rude about where she dropped her keys.”
Fifi felt her skirt being lifted and fingers slipping into her panties waistband. “Let’s see if we can find them in this mess….”
Fifi felt what she assumed was Gloria’s hand rooting around her cock and balls looking for the keys. Cheerfully Gloria declared “Found them!” Then the waistband snapping back into place. Fifi gave out a small whimper at the snap.
“Don’t worry Fifi.” Gloria told her “Yes, this was all a big setup. Your friend Maggie arranged it all, including this final event.”
“Peter, here are the keys, you might want to rinse them off first.” Gloria said “Here’s her leash, do your magic.”
“Magic?” Fifi thought to herself.
The Final Event
“Let’s get you out of that darling Maid outfit Fifi,” the unseen male voice said loudly, “Walk this way behind the curtain and we’ll get you a chair.”
Peter led Fifi behind a curtain and had her sit in a folding chair. Then unlocked all the locks, helping Fifi remove the hood, the apron, the mitts, and the ankle straps and heels. Fif looked around with interest once the hood was off. Fifi noticed Peter was wearing a long leather skirt, very high heeled boots and a white blouse and a very long blond wig.
“Can you peel that PVC dress off, Fifi, and we’ll get you out of that corset," Peter told her.
Fifi stood up and peeled the dress off over her head, standing in front of Peter wearing the black corset and the pink latex panties, over fishnets and garters.
“Spin around and we’ll loosen those laces," Peter commanded. Fifi spun around and leaned on the back of the chair.
Peter untied the knot and tugged at the lacing working his way up and down and loosening the corset as he went. “They did a good job of lacing this shut, but it’s the wrong kind of corset for the purpose.”
Peter continued explaining as he unlaced “You see this is an actual womens corset. For crossdressing purposes you need a corset designed to rearrange a man's shape.”
“That's loose enough to open the busk in front, spin around love.” Fifi obeyed and Peter undid the corset fully, unhooking the garters from the stockings. Fifi took a deep breath for the first time in hours.
“Thank you, Peter,” Fifi said with gratitude.
“Don’t thank me yet darling.” Peter threw Fifi a towel and a washcloth “There’s a men's room about 20 feet that way.” Peter pointed towards the far wall of the convention space. “Go take a sink bath and rinse those nasty cum filled panties out. Come back wearing just the towel.”
“Just the towel?” Fifi asked nervously.
“You've been walking around this entire room in a PVC maid’s outfit on a leash, and you are worried about a towel?” Peter laughed and just waved Fifi to get going. “Hurry back, we have work to do.”
Fifi found the men's room and thankfully it was empty, she…he pulled the fishnets off and popped the breast forms off his chest. Phil looked into the mirror over the sink and shifted mental gears. He still had to peel off the latex underwear and deal with the mess in there. He let the warm water run for a minute in the sink and got the washcloth wet. He pulled the underwear down and off as quickly as possible and tossed them under the running water. Then using the wet washcloth, did his best to clean up the sticky mess coating his cock and balls. He rinsed and applied the washcloth multiple times, before feeling that was the best he could do outside of an actual shower. He wrapped the towel around his waist and rinsed out the pink latex panties. Gathering everything back up, he made his way back to Peter’s curtained off back area. He had trouble finding the gap in the curtains but eventually found the right gap and found Peter sitting there waiting.
“Ah there you are Fifi!” Peter called out.
“Ummm, it’s Phil actually. Nice to meet you. “ He held out his hand to Peter.
“Yes, yes, I know. Maggie explained how you just play dress up, it's not a lifestyle thing.” Peter took Phil’s hand and gave it a squeeze.
“Just put all those dirty things on the table there," Peter indicated an empty space. “Do you know what I sell Phil?”
Phil put the dirty clothes off to the side, then sat in an empty chair opposite Peter. “Not really, no.”
“Peter Perfect’s Products are famously known in the crossdressing community," he explained to Phil.
“Crossdressing Products?” Phil asked hesitantly.
“Yes Fifi, you aren’t done yet," Peter told Phil. “Or should I call you BunBun?”
Phil looked confused, Peter smiled “Time to get dressed for the party.”
The Party
Maggie clapped her hands in delight as Peter delivered Phil to the party. Gloria was there and several others
Peter arrived at the party, Phil wearing a cloak that had covered his costume up as they made their way to the private party in one of the hotel suites. “As promised, one fully converted Playboy Bunny.” He said as he pulled the cloak off his latest creation.
Phil was now Fifi BunBun, he made another mental shift of gears.
She posed in her new outfit for Maggie and her friends. Peter had squeezed Phil into a heavily boned leather Bunny suit. It was one designed for men to wear, with an obvious “pouch” in the crotch area to accommodate the wearer's cock and balls. Peter had attached false breasts with spirit gum and they filled out the top of the costume very effectively. Two pairs of nylons, the first a shimmery nude pair and then traditional fishnets covered BunBun’s legs. The same high heels from the earlier Fifi costume were repurposed for BunBun. Mock collar and cuffs enclosed the neck and wrists to complete the costume.
But Peter’s skills extended past mere costuming, Fifi was now in a long blond wig and in full face makeup. A domino mask and Bunny ears completed the look.
The ladies examined the entire outfit and complemented Peter on his efforts.
“A miracle, a masterpiece.” Gloria said.
Maggie ran her hand over the back of the bunny suit. “Where are the laces?” she asked Peter.
“One of my more clever designs. The laces are underneath a protective cover” Peter went behind BunBun to show the ladies the design. “Once you lace it shut, this back panel covers the entire back piece and uses velcro alongside the side seams about three inches to the left and right of the spine. Giving it a smooth appearance and the illusion of no way to get in or out of the suit.”
“Very clean look.” BunBun heard one of the ladies comment from behind her, she recognized the voice as Mary the vibrator seller.
Then suddenly she felt someone slap her ass. “I know that ass, is that Fifi?” A voice she recognized as Sally the crops and paddles booth owner greeted the group clustered around BunBun.
Then she heard a male voice say, “Bend her over a chair to be sure.” Fifi recognized that as the voice from the bondage furniture booth, she couldn’t stop herself from rubbing her bottom with her hands in remembered pain.
Apparently everyone from the Quest for the Keys was at this event.
Maggie ordered “Go get us drinks Bunny. That’s what BunBuns do after all.”
BunBun curtsied and headed to the makeshift bar on the other side of the oversized hotel suite. Between the heels and the corset she felt herself almost unconsciously swaying her hips with every step.
She waited behind two others ordering drinks and couldn’t help but overhear their conversation.
“Did you see the latest uploads to youtube with the Con’s hashtag?” one said to the other.
“Yes!” the second exclaimed “It’s only the first night and apparently there is a crossdressing French Maid all over the internet.”
“Those videos are insanely hot! Do you think she will show up here?” the first person asked.
The second answered “How would we know? She was wearing a full hood in all the videos.”
Bunbun smiled quietly to herself, wondering how they’d react if they knew the French Maid they were talking about was right behind them.
They got their drinks and moved to the side, Bunbun asked the bartender “I need three rum & cokes, one vodka martini, and two whiskies.”
The female bartender started making the drinks and talking to Bunbun at the same time “I didn’t know we had a cocktail waitress here tonight, the costume looks good on you.”
Bunbun blushed slightly, “It’s just a costume, I’m here with friends.”
“I think I have the perfect accessory for your costume.” the bartender smiled and placed the drinks she was making on a serving tray. “Here you go, a cocktail tray for a cocktail Bunny," she said, handing the tray to Bunbun.
“Thanks!” Bubun said, and picked up the tray full of drinks.
She delivered the drinks safely to Maggie and the rest of the group.
Gloria asked where she got the tray
Bubun told her. “The bartender gave it to me, and said it was the perfect accessory for my costume.”
“Oh she did?” Maggie remarked.
“Funny story,” Bunbun told the group “When I ordered the drinks, she thought at first the party had hired a waitress,” She chuckled at the idea.
Maggie said “We have to return the tray to this friendly bartender.” She grabbed Bunbun by the wrist and half led half dragged her back to the small bar.
The bartender wasn’t helping anyone at that moment, so Maggie walked up and put the tray on the countertop.
“Bunbun tells me you don’t have a waitress to help serve the drinks?” Maggie asked the bartender.
“No ma’am, apparently they could only afford me.” the bartender told Maggie, then asked “Why do you ask?”
“How would you like some free help for the evening?” Maggie replied with a wicked smile.
Bunbun was suddenly very nervous.
“Are you suggesting what I think you are suggesting?” the bartender smiled back.
“Bunbun would gladly help you out tonight, she’ll work for tips.” Maggie volunteered her.
“But I’ve never been a cocktail waitress!” Bunbun protested.
“I’ll teach you everything you need to know.” The bartender was still smiling at Maggie and Bunbun.
“Maggie, I’m not sure about this.” Bunbun commented.
Maggie, still smiling, whispered to Bunbun “You can be a cocktail waitress tonight, or tomorrow I’ll put you in a costume so kinky it’ll make Fifi look like Little Red Riding Hood.”
Bunbun turned to the bartender, “I’d love to help you serve drinks tonight.”
“Excellent!” the bartender said “My name is Tonya, hop back behind the bar and we’ll get you set up.”
Phil switched yet another set of mental gears. So far he’d gone from He to Fifi, back to He, then to Bunbun, now to a Cocktail Waitress, the pronoun whiplash was giving him/her a headache.
It had been a very full day, and Halloween weekend wasn’t over yet.
