sissy Undercover Sissy

[PinkTheDinosaur]

this story was commissioned by Brisemenu.

Ch1

"Hello and welcome to Sally's Sissiys Daycare!" a woman wearing a bright green apron with a picture of a large smiling Seal on a beach printed on it. "Im Magen, and it's nice to meet you!"

Megan was in her early 20s and had a large smile as she greeted the new guests that came into the daycare.

"Hi, im Janet and this is my little sissy Max," she gestured to the short preteen-looking child hiding behind her and holding onto a stuffed bear while sucking on a pacifier. 

Janet was an older woman in her early 40s. She wore a casual dress and looked to be fit for her age. 

Max was 24 and was born a "Sissy." He was 4'9 with a slim build and wore a bright pink and red dress that just barely covered the diaper she had to wear. 

********

In this world, Males were divided into 3 categories. 

The average was the most common. And like you would suspect, they were average all around. 

Alpha's were rare and tended to excel in some way. Excelling in strength, stamina, smarts, or more. The drawback of their fantastic gift was that they could not reproduce due to a genetic problem in their DNA. 

The final was the Sissys. One in every 10 men was born as Sissys. They grew to be smaller and more feminine than average men. Their height typically stunted at around 5 feet, and they mentality matured very slowly. Tipickly capping with the mentality of a teenager by 30. Though most never matured past childhood and were treated more like young girls than boys. Dew to their stunted growth and other factors, they have a few other problems. There is little to no muscle mass, leaky bladders, weakened bowls, etc. Due to this, most sissys are treated like small children who need to be diapered.  

******

"Oh, do we have another little one joining us?" another young woman asked as she walked over to join her coworker. "My name is Kelly."

Kelly looked slightly older than Megan and had green streaks in her hair. She also had huge breasts with a pin poking out between them.

"It's nice to meet you." Janet greets the other attendant while picking up a pen to sign a few papers. "Is there anything I should know or tell you before signing?"

"Yes, for starters, how long will you be leaving Max with us?" Magan asked.

"Just a few hours. I have a few meetings, and our normal babysitter got sick. Im not entirely sure when ill be back, but I would be back before closing." Janet tells them.

"That's fine. We will be sure to feed your little one during lunch and give them a snack. Do they need a bottle, or can they use a sippy cup?"

"She's a big girl. She can use a sippy cup."

"Good to know. Do they need special diapers, or are you fine with any brand?"

"Any brand of diapers is fine."

"Good, and lastly, dew to how some Sissy's can be troublesome, we ask for permission to spank as punishment to keep them in line. Are you ok with bare bottom spanking or clothed spanking?"

"Clothed spanking, though you won't have to worry, Max here is always well behaved," Janet said while patting Max on the head before signing the papers. "Ok, darling, you have fun today, and mommy will be back to pick you up in a few hours.

Janet leaned down and kissed Max on the cheek before whispering something to them. Max blushed but nodded while hugging the bear tighter.

"Come along, sweety, you can have more fun in the other room," Megan says while gesturing towards a door decorated with rainbows and bunnies.

Max could hear screams and cheers of other "children" playing in the other room as soon as the door opened.

He could see about a dozen other Sissys running around playing when he walked in. They were in some form of childish or baby attire despite looking more like teens. If it weren't for the diapers, most of the sissys could probably pass as young teen girls if it weren't for their childish behavior. 

Almost immediately, one of the Sissys noticed Max and ran over to them to greet them.

"You play?" the sissy wearing a bright orange dress and long blond hair asked.

Max let out a whimper before running over and standing behind Kelly's leg.

"Hey, it's ok, Max. Jacob here just wants to play with you. Wouldn't you like to play with them?" Kelly asked but only got a head shake, no in response. "Sorry, Jacob, but Max is a little shy. Maybe in a little while, she will play."

Jacob sighed before running back towards the other sissys to play while Max stayed next to the nursery attendant. 

They didn't mind. Magan was used to some Sissys being shy and wanting to be next to someone "Grown-up." By their late teens, most women were taller and stronger than most sissys. Kelly was 5' 9" and was a foot taller than every sissy in the daycare. To all of them, Kelly was a grown-up while they were children.

As long as Max didn't get in the way of her work, Kelly or Megan didn't care what the cute little sissy did. 

The daycare looked just like you would expect. An oversized playroom filled with toys and soft furniture all over the place. 

Max watched as some sissys sat in the corner coloring at a small table with crayons all around them. Others were playing with large blocks, stacking them and knocking them over. And a few were playing with dolls and stuffed animals. 

"We dont have any more coming in today, right?" Kelly asked her coworker.

"No, Max was the last one for the day," Magan responded while watching everyone.

"That's good. I'll go start on lunch then." Kelly tells her as she leaves for the kitchen.

Once Kelly was gone, Megan received a message on her phone. 

Max was curious and stood on his tows to take a peek.

"Transfer has been excepted." was what Max could make out.

"Curious?" Magan asked when she noticed the sissy looking at her phone. "This is for my application for the children's daycare across town. They liked progress here with sissys and will be promoting me to watch the regular children."

In this world, while Sissys are treated like children, most places still prefer to separate them from the actual children. To work with small children, it is often required to practice looking after a sissy before being able to handle small children. 

Magan knew sissys like Max didn't care about her personal life or even understood what some of the bigger words meant. But it was nice to tell someone about her accomplishment. And for a moment, Magan could have sworn Max could almost understand her entirely based on Max's smile behind his pacifier.

Before that thought could linger, Magan and Max heard a commotion. 

"THAT TOY IS MINE!" a Sissy in a blue onisy shouted as they pulled on another sissy's hair.

"Lola! Bad girl! No!" Magan shouted while running over to the two sissys to separate them. "Lola, this is strike 3!"

Magan griped onto Lola's hand and began dragging her towards a chair. Lola pleaded no and tried to pull herself away from the caretaker before she started to bawl.

Max watched as Magan sat down on a chair and pulled Lola over her lap.

"We gave you two warnings Lola. You know the rules. Strike 3 means 6 spankings." Magen says as she pulls the sissy's diaper down to show off their bottom. 

Lola screamed, kicked, and tried to cover her butt with her hands, but Magan was able to pin the sissy's hands behind their back before the spanking started.

All the sissys flinched as the sound of the first smack echoed out. Lola cried even harder as her butt felt like it was on fire. Then came the next Smack, and another shrill scream came out of Lola. 

Max stood in front of Magan and Lola while clutching onto her stuffed animal. Her eyes were closely watching as the third smack hit.

As soon as the final three spankings were done, Magan pulled the diaper back up and lifted Lola to her feet. Lola was still bawling her eyes out as Magen stood up and gave lola a quick hug before she had Lola sit down in the chair.

"You in time out until lunch. You know better, little girl." Magan tells her before turning to the rest of the sissys. "I hope this is enough of a warning to not be naughty."

All of the sissys, including Max, nodded in agreement. All of them not wanting to be spanked by a grown-up.

*****

About 20 minutes later, Kelly called for all the little ones to line up.

Most of them cheered while Lola sniveled as they all ran over to the kitchen and got in line. Max was at the back of it. 

The kitchen was decent, with a large table and chairs for all the sissys to sit at. In front of each chair was a plate with a sandwich and chips. Kelly had everyone grab a sippy cup from her before going to the table to sit.

All of the cups were red except for one lone blue cup.

Kelly handed everyone their cup. But gave Lola the only blue.

"Sorry, sweety, but you have cant have toys at the table," Kelly tells Max as she hands him a sippy cup.

Max nods before running over to a counter to place the stuffed animal down before hurrying over to the table. 

Max remained quiet at the table despite all the other sissys loudly talking while they ate. He looked at everyone shyly turned down anyone who wanted to speak to him. He just wanted to finish eating soon and get back his stuffed animal.

But out of all the sissys, Max wasn't the only quiet one. 

Lola was also quiet, though for a different reason. She had only eaten about half her sandwich and was now staring down on it while her body fidgeted. She tried to keep her head low, but Max could make out the tinny smile she had.

"Eww! Someone pooped!" 

"Mis. Magan! Lola pooped!" a sissy next to Lola yelled while fanning their face. 

"Oh no. come on, Lola, I can help you clean up," Magan tells Lola.

"How about I do it. Let you relax a moment after watching the kids." Kelly suggested. "Come with me, Lola."

Lola happily got out of her chair and followed Kelly. 

Max also got down from the table.

"Done already, Max?" Magan asked as Max put his pacifier back into his mouth and ran over to his toy. Max nodded to her before running off to follow Kelly and Lola.

Magan just shrugged. Knowing Kelly could handle watching the two while she kept an eye on the other sissys. 

Kelly opened the door to the changing room and was surprised to see Max had followed them. 

"Do you need a diaper change too?" Kelly asked.

Max shook his head no, but Kelly still lifted Max's dress to take a peek inside. Inside, Kelly could see the pink cage some parents had their Sissys wear. But the diaper was dry.

"Did you just want to see how to change a diaper?" Kelly asked. She was tempted to send Max back to the kitchen, but it wouldn't hurt to have the sissy watch.

Max nodded excitedly as Kelly smiled down at him and pet the sissy on the head.

Lola was already on one of the 3 large changing stations in the room. She was no longer crying and, in fact, looked like she was excited about something.

Max watched as Kelly put on plastic gloves and pulled out the changing supplies.

Max coiled in discussed when the diaper was opened, and he saw the diaper's contents. Kelly was unfazed and didn't mind it so much anymore. She cleaned up all the diaper contents very fast and used a wipe to really clean a place Max knew all "adults" Lola's no-no spot. A place only grown-ups could clean for sissys.

Max watched as Lola's no-no spot grew hard and stiff while pointing straight up. 

"See that little Max?" Kelly asked. "Some sissys get that way, and it's sometimes hard for them to stop. So im going to help little Lola feel good to make it go away."

Max turned to look up at Kelly with his stuffed animal looking up while Kelly clicked on her pen before rubbing baby oil on her gloved hands.

"It's still so cute how despite being 22, Lola's little friend here isn't as big as my pinky."

She swirled her pinky around Lola's no-no spot before lightly pinching it with her thumb and index finger and moving her hand up and down.

Lola's hands clutched her shirt tightly while happily panting the pleasurable sensation. 

"Now, let's give little Lola something better," Kelly said while using her free hand to slide between Lola's legs and poke at her butthole. 

Lola squealed happily as Kelly's oiled-up middle finger slid in easily before going all the way in.

"Aw, even sissys like it when something long is put in there," Kelly commented as Max just watched the whole ordeal. 

He reached up to his pacifier and turned a little nob on the front.

Lola began to pant even harder and harder until she let out a loud moan while her body twitched and white stuff spewed out of her no-no spot.

"There we go," Kelly says as she pulls her finger out of Lola's butt and grabs a few wipes to clean up the little mess. "Such a good girl Lola."

Kelly then taped the new diaper on before clicking the pen once more. 

"Ok, max, would you like to try it?" Kelly asked with a giant smile on her face, but Max shook his head no. "oh, dont worry, sweety, I can't take off your cage, but I can still make you feel just as good as Lola. watch."

Max was getting a bit worried as he backed away while Kelly stepped forward to pull Max over to the changing table. But before Kelly could grab Max, the bell to the front door went off and signaled that someone had opened the front door.

Kelly got back into business mode and walked out of the changing room with Lola and Max following. Lola now has a relaxed smile on her face after feeling good.

"Oh, miss Janet. Nice to see you again. But I thought you said you would be busy for a few hours? It's only been 1." Kelly says as she greets Janet.

Max immediately runs over hugs his mommy.

"Awe, I missed you too, sweety. And yes, I thought I would be busy too, but one of my meetings got canceled, and the other was finished much faster than I thought." Janet tells Kelly with a bright smile. "How was my little darling."

"She was perfect," Kelly tells her with a bright smile. 

"Such a good girl," Janet said as she hugged Max before kissing his cheek. 

Janet signed and paid for the service before taking Max to the minivan and opening the back seat. Their sat the Large car seat Max had to get into.

Once Janet was in the car, the two of them pulled out of the daycare parking lot while giving a small smile and waving to Kelly in the window.

As soon as they were out of view, Janet's smile quickly disappeared as she let out a huge sigh. 

"God dame, I hate having to do this!" Janet yelled. Why couldn't they have put someone else in this stupid dress to play mommy!?"

"Hey, orders are orders." came a voice behind Max as a Guy sat up from the back. "Now stop complaining.?"

Max spit out the pacifier before handing the stuffed animal to the guy. The shy personality was whipped away from his face.

"Hey, i would take that dress over being forced to ware a diaper anyday.," Max tells her while turning his head twords the back. "Oh and garage, you oh me $50."

"No way you did all of that without speaking!" Garage shouted as he took the bear and opened the back of the head to see a camera hidden inside.

"Check the tape."

"So who was it? Kelly or Megan?" Janet asked as she lit a cigerit.

"Magan is clean. She has a great record and still follows all the rules. Including when it came to spanking. Just enough to send a message, but not hard enough to leave marks." Max told them.

"So it was Kelly?"

"Yep. Kelly most likely records it with the pen on her chest," Max tells them.

"Fucking sick bitch. Sexual acts with sissiys are disgusting. Let alone filming it and selling it online for a qwick buck." Garage sais while downloading the evidence to his computer.

The police learned about the illegal filming a few weeks ago and could pinpoint roughly where it was coming from but could not tell who was doing it. 

That is why they had to send in their top-secret weapon. The undercover sissy.

Max was unlike all Sissys. He was a Beta. 

They are physically just like every other sissy except for mentality. Beta's have normal brains. However, Betas are extremely rare and tend to not be taken seriously by everyone. 

But that's what makes them perfect for going undercover to help protect abused and exploited Sissys. 

"So, what is next?" Max asked as he was handed his next undercover assignment and smiled.

 

[fire07]

This is a great story. I love the little universe you built. That being said you seriously need a proof reader or to at least run a basic spell check.

[PinkTheDinosaur]

14 hours ago, fire07 said:

This is a great story. I love the little universe you built. That being said you seriously need a proof reader or to at least run a basic spell check.

lol thank Brisemenu. they are the one who came up with the idea. i just helped flesh it out a bit. ^w^

as for a proof reader, while i have some people that help me with that for some of my stories, Sissy stories are ones they are not interested in and are harder to proof read... im working on a way around that soon. hopefully.