tagTransgender & CrossdressersThe Pantysissy Diaries Ch. 02

The Pantysissy Diaries Ch. 02


This is a 3rd person fiction story about my fantasies of being a Pantysissy. All characters in this story are made up, and are all over the ages of 18. To better follow this story read The Pantysissy Diaries Chapter 1 before reading chapter 2.


The Amtrak train Jaymie was onboard with his new Mistress, Sydney had just pulled into NYC. Jaymie had to get his work bag and suitcase before getting off the train. Jaymie was wearing Red, White, and Blue Amtrak panties, a pink tiara, red high heeled shoes, hot pink stockings, a pink garter belt, a pink Victoria's Secret bra, and a pink lace wedding cap. Jaymie also had bright red lipstick on, and Jaymie's fingernails and toenails were both painted in hot pink nail polish.

Needless to say, Jaymie was dressed as a full blown sissy.

As Jaymie and Sydney walked off the train together, Sydney told Jaymie how they were going to get to their apartment.

"Now listen Jaymie, our apartment is 10 blocks from here. We are going to take the subway, which will put us 5 blocks from our apartment. And then we will walk the rest of the way there."

"Ok, Mistress Sydney," Jaymie replied.

They got onto the subway, and immediately people onboard starting staring at Jaymie. Not only that, but most of them started to take pictures of Jaymie. But all Jaymie could do was blush.

"It's ok everyone. My sissy and I are on our way home to our apartment," Sydney told the crowd onboard.

"What's her name?" asked one lady.

"Her name is Jaymie," Sydney replied.

"Well Jaymie, those are some very sexy panties."

"Thank you miss," Jaymie replied.

With that they got off the subway and began the walk to their apartment. It was a nice day in late April, so it was a pleasant walk. Still though the sight of Jaymie stopped some traffic.

People came up to Jaymie and started taking pictures. One lady asked Jaymie to pose with her, and Jaymie did. Soon Sydney and Jaymie had made their way to their apartment. Once they walked in the front doorway Jaymie expected to see a man greet them at the front desk. After all, it was a luxury apartment. There was a greater, but it wasn't a man. Sydney and Jaymie walked up to the front desk.

"Hey Jess, did you get my text?"

"While yes Sydney, I did," the lady responded.

She then introduced herself to Jaymie.

"Hi I'm Jessica, and you must be Jaymie. Sydney has told me all these great things about you. You're gonna love it here."

"Hi, Jess."

"Your apartment room is on the 35th floor. Take the elevator on the far right," she told Jaymie.

Jaymie and Sydney then got on the elevator. At first nobody was on it. Then on the 11th floor a couple of young women got on. They took one look at Jaymie and started giggling. All Jaymie could do was smile back. After all, Jaymie was still wearing Red, White, and Blue Amtrak panties, a pink tiara, red high heeled shoes, hot pink stockings, a pink garter belt, a pink Victoria's Secret bra, and a pink lace wedding cap. The 2 women got off on the 29th floor.

But before they did, they requested Jaymie to get on his hands and knees with his ass pointed up, Jaymie did as told. They then stood next to Jaymie and asked Sydney to take a picture of the 3 of them.

The 2 women pointed their hands towards Jaymie's panty covered ass in the picture, and then just like the gay guy on the train before, gave Jaymie's buttcheeks a good 2 handed slap. Then they got off the elevator. Sydney and Jaymie were the only people left on it at that point. Jaymie glared at Sydney.

"What can I say?" Sydney said as she shrugged. "A good pantysissy must be properly punished."

The elevator then got to the 35th floor and they got off of it.

"This way!" Sydney motioned as she pointed towards a door all the way on the left side of the hall.

"This is it Jaymie, room 6969."

Sydney then opened the door.

"WELCOME HOME JAYMIE!!" 5 sharply dressed attractive women shouted as Jaymie and Sydney walked in.

"Hi... Who are you guys?" Jaymie asked.

"We're Sydney's roommates, and now your new housemates! We're here to make your pantysissy experience living here as great as possible," one of the women responded.

Jaymie then looked at Sydney.

"I thought you told me you only had 1 roommate?"

"I lied," Sydney responded.

"Well, at least tell me your names then."

From left to right they answered.

"I'm Torrey."

Torrey was a tall blonde wearing a light blue pencil skirt and light blue high heels with blue nail polish.

"I'm Rose."

Rose was a medium redhead who was wearing a red buttoned down lace up dress and black high heels with red nail polish..

"I'm Tiffany, but call me Tiff."

Tiff was a short brunette wearing a yellow bikini, and easily the hottest woman there.

"I'm Rachel."

Rachel was a tall brunette who had a light blue cocktail dress on and white lace heels with white nail polish.

"And I'm Sam."

Sam was a tall blonde wearing a white see through lace cocktail dress with black high heels and black nail polish. Sam offered to show Jaymie around.

"Come Jaymie. Let's head to your suite."

"Ok, I like the sound of that," Jaymie told Sam.

"Ahem," Mistress Sydney interrupted.

"But before she shows you around understand this. You will address all 6 of us as Mistress. Understood?"

"Yes, Mistress Sydney."

"You have so much to learn Jaymie," Sydney said giving Jaymie's cock a pinch in his panties. "Jaymie, you are a perfect pantyboy, and will soon become our pantysissy. Understood?"

"Yes, Mistress Sydney."

"Now go follow Sam to your room. And don't forget, that's Mistress Sam to you, pantyboy."

Jaymie nodded.

Mistress Sam led Jaymie down the hall past 5 medium sized rooms and 1 large room.

"The larger sized room is Sydney's and the medium sized rooms are mine, Tiff, Rose, Rachel and Torrey's. They are all connected through a doorway in each room and the hallway. Here's your room!"

Sam led Jaymie inside a large room. The walls were all painted hot pink. There was a hot pink queen sized bed set. On the wall directly above the bed set was a sign that read "WELCOME PANTYBOY! Another sign read "SISSY'S ONLY PAST THIS POINT."" In the room there were hot pink dressers and drawers. There even was a hot pink mirror right next to the bed. There was also a giant flat screen TV against one of the walls.

"Is this all for me?" Jaymie asked.

"It's all yours!" Mistress Sam responded.

"We've been planning for your arrival for a few days now. Now, please lie down on the bed, and spread your arms and legs wide. We need to measure for your bed restraints."

"Bed restraints?"

"Yes Jammie, bed restraints. A good sissy always sleeps with bed restraints."

"Ok, Mistress Sam."

Jaymie lied down on the bed, and spread his arms and legs out wide. Mistress Sam took out the bed restraints and tied Jaymie up. There were 4 restraints total, 1 for each of his hands and legs.

"6 Inches Jaymie, boy you're a big pantyboy. But silly, you're no boy at all. You'll be our pantysissy in no time. However, there's a lot more to being a pantysissy than just wearing panties. For starters you're going to need to be gagged at times, and that starts now. You will also wear your chastity when we say so. And both of those start now."

"What?" was all Jaymie could get out before Mistress Sam took out a pink harness gag and placed it over Jaymie's head and the gag part in his mouth. Mistress Sam then took out a pink chastity and slipped it on over Jaymie's rock hard cock underneath his panties. She then held the chastity key dangling over Jaymie's face.

"You won't be needing these unlocked for a while, pantyboy."

"Girls come!" Mistress Sam called, "I think it's time to introduce our resident pantyboy to our house rules."

With that the rest of the 5 mistresses came into Jaymie's room.

"Mistress Rose will do the honors.."

"Jaymie darling, if you want to live in our house, you are going to have to play by our rules. Here they are:"

#1. "Each day when you wake up you will see your daily schedule listed on the flat screen TV against the wall. You are to do exactly as that schedule describes. Understand?"

Jaymie nodded. "And as part of that schedule you will have assigned theme days. Those themes are the major part of your day for those assigned days. You will have seven theme days in every week. Your theme days are as follows.

Mondays will be Makeup Mondays. Every Monday you are required to go down to the beauty parlor, and get a mani/pedi, as well as your hair done by the salon staff. You are also required to have both your fingernails and your toenails painted.

They will also shave your entire body. Aside from your eyebrows, and the hair on your head, which they will be dying a color we choose, you will not have a single blade of hair anywhere on your body. So that means they are going to go ahead and shave your clitty.

Lastly you will let the salon staff apply makeup to you. That includes lipstick, eyelash, mascara, and anything else they want to add. They have full discretion and final say over your appearance for the upcoming week. They can do whatever they want with you. We will decide your weekly wardrobe.

We will take you to the salon with us the first time, but after that you're on your own. You will check in with the salon staff every time you arrive, and check out with them every time right before you leave.

Before we get to Tuesday's themes you must receive your piercings, which we will take you for tomorrow. You will be getting both of your ears pierced so you can wear women's earrings 24/7, as well as your belly button pierced, which you will be wearing your pink sissy belly button ring 24/7.

Tuesday has three themes. The first being that every Tuesday is tattoo Tuesday. On every Tuesday you must head down to the tattoo parlor, and get some sort of panty or sissy tattoo. We will choose which tattoos you will get, and where on your body you will get it. And we know exactly where on your body you will be getting your first tattoo. And we have already picked the design too. You will also need to check in with the tattoo parlor once you get there, and check out once they finish your tattoo.

The second theme for Tuesday is every Tuesday will be Transit Tuesday. That means on every Tuesday you must choose some form of transit in NYC and ride around on that form of transit for 4 or more hours in the sissy clothing that we will pick for you to wear that day.

And lastly Tuesday's Third and final theme is Tranny Tuesday. On Tranny Tuesday, you must spend a minimum of 4 hours obeying a shemale, and doing exactly what she says. And luckily you have 6 of them in this room staring right at you, girl.

Next is Wednesday.

Wednesdays will be known for you as Worship Wednesdays. On Wednesdays you need to worship women, and worship your cause as to being a sissy. That means on Wednesdays you will dress up in the sissy clothes that we pick for you and go to whatever church or store that we pick for you that day.

At that church or store you will worship the women there and tell them how superior they are to you, as a sissy. You will spend a minimum of 4 hours there, either praying for them or with them. It could also be buying, carrying, or trying on clothes for them. Or licking women's feet or shoes in public. The sky's the limit for Worship Wednesday. Either way, you must publicly worship women on Worship Wednesdays, and do exactly as they say.

Now for Thursdays.

Judging by what we've seen in your suitcase, we think Thursdays will be of particular interest to you. For you, Thursdays will be known as Thong Thursdays. Every Thursday you will go around the city wearing the thong(s) we pick out for you for that day, and only that thong. You will wear nothing else on Thong Thursdays except your thong.

Next is Fridays.

And we think Fridays will be your absolute favorite day of the week. Fridays have two themes. The first theme is Fridays are known by women as shopping days. And we all know there's nothing you like doing more than shopping for panties at Victoria's Secret stores. So that's exactly what you will be doing on Fridays.

But there's more to it than just that. Every Friday you must buy a minimum of 10 pairs of panties at Victoria's Secret, and you must spend a minimum of $100 on those panties. You also will be required to try on every single pair of panties, you buy at Victoria's Secret on Fridays.

And furthermore, you will travel to Victoria's Secret wearing your sissy clothing and Victoria's Secret panties that we pick out for you for that Friday. We will take you shopping at the closest Victoria's Secret tomorrow for the first time, so you know where it is, and how to get there. After that you're on your own.

You will also be signing up for the Victoria's Secret Angels Credit Card tomorrow. And like the salon, you will also be required to check in with the store workers as soon as you get to Victoria's Secret on Fridays, and after you check out once you leave. And that's only your daytime on Fridays. Wait till you see your nightcap.

On Friday nights we will head out on the town, enjoying the nightlife of NYC. You however will be staying home, entertaining a new Friday night mistress(es) every single week. We will be auctioning off every week the chance for a random paying person(s) to be your mistress(es) for that night. That's right, Friday nights for Jaymie will be known as Fendom Friday Nights.

Every Friday night Jaymie will entertain and obey a new mistress(es) that we will award them your service via auction. And just like with us, you will do exactly as they say. Sounds exciting, doesn't it? That's just the start of your weekend, sissy.

There's a saying on social media called "Saturdays are For The Boys." That is absolutely true, except for you, because you definitely are NOT a boy. You are a sissy, and you will be doing sissy things on Saturdays.

What could be more sissy than trying on, buying, and modeling swimsuits for runways and photoshoots? That's because Saturdays for you will be known as Swimsuit Saturdays. Every Saturday for Jaymie will consist of you wearing swimsuits for the entire day. And those will be women's swimsuits, which are called bikinis and leotards. Real men wear swim trunks for swimsuits, BUT you are nowhere near a real man. You are a sissy, and that's why you will be wearing women's swimsuits on Swimsuit Saturdays.

You didn't think we would just let you off the hook, and have Sundays off. Did you? No, we're wayyyy better than that. On Sundays, you will belong exclusively to Mistress Sydney, as Sundays will be known as Sydney Sundays. She is your Mistress after all, and she's the one who found you in your panties.

On Sundays Sydney will have Jaymie all to herself, and she can do whatever she wants with you. She can have whomever she wants over, and go wherever she wants with Jaymie. She can also leave Jaymie to do whatever she says.

Sounds exciting doesn't it? And don't worry Jaymie, you will definitely be having monthly theme days too, not just weekly theme days. And keep in mind, we can add anything to these theme days or change them at anytime, so be prepared my sissy!

#2 Our next rule is that you will wear panties in our house at all times. This is non-negotiable Jaymie. You are a sissy, and sissies wear panties all the time. We will be burning all of your work boxers. You will be buying a minimum of 10 pairs of panties at Victoria's Secret every week, and your sexy drawers will have no room for disgusting old boxers.

#3. You will be quitting your job. You live in our house now, and we are in charge. If you are going to be performing all these tasks on your theme days, and behaving like a proper sissy, then there is no time for work. You job now is to obey us at all times. We are who you work for.

#4. Your girlfriend has been informed that you've broken up with her. You are a sissy now Jaymie, and sissy's do not have girlfriends. They have mistresses whom they obey and serve. You have 6 of us right here, and plus whomever comes for you on Friday nights. You will obey us, and do exactly as we say.

#5. You have given your apartment up, as you now live here with us.

#6 . The makeup and hairstyle that you receive every Mondays at salon will stay on you for the entire week. You will not change the hairstyle or remove any makeup or nail polish until you go back to the salon the next Monday.

#7. In addition to you wearing panties at all times in the house you will now wear bras and corsets in our house at all times. Men do not wear bras or corsets, but you are no man. You are a sissy who will behave, act, and dress properly like a woman. Therefore you will wear bras and corsets in our house at all times. You will be buying for your first bra at Victoria's Secret on Friday. You will be asking a sales associate to measure your bra cup size in front of everyone in the store.

#8. What we say goes. You have no jurisdiction here. None, whatsoever. We are in charge of this house, and we are in charge of you at all times. Even if we're not in the house, we can see what you're doing 24/7.

#9. We have hired a camerawoman and journalist who will broadcast and chronicle your every move. Her name is Monica and she writes for Mistress Magazine. You are being featured for a weekly column in the sissy section of the magazine. Monica will be live streaming your Fendom Friday: Mistress of the Week outings every Friday night on the website. You will do exactly as she says.

#10. All of your drawers in the house are here in your room. They will be used for lingerie, and lingerie only. In fact, you will wear nothing in this house except lingerie, women's jewelry, women's shoes, and women's swimsuits.

#11. You will sit down to pee and poop. Women sit down to use the bathroom, and sissies do too. You are a sissy, so you will be sitting down to use the bathroom in this house, and any other bathroom you use anywhere else.

#12. The bathroom and showerpad that you will be using is located in the middle room. We have a public bathroom especially and only for you, so everybody can see you using the bathroom and taking a shower like the good little sissy you are. That bathroom is only to be used by you, and any mistress who either wants to use it with you, or forces you to use it. When using the shower, you will wear a women's swimsuit at all times.

#13 Anytime you disobey us will be met by harsh punishment. Everyone in this household has a cock, including your pathetic excuse of one, and we are not afraid to use it.

#14. You will use an enlarged chastity when sleeping and eating. Again, this is non-negotiable.

#15. You will sleep with your hands and feet tied up in your bed restraints.

#16. You WILL sleep wearing your enlarged chastity UNDER your panties. You will not be wearing anything else except shades, lipstick, and a bra when you sleep.

#17. You will ask for permission anytime you wish to use the bathroom. You will recite the following when asking permission to use the bathroom:

"Mistress ____ May I please have the permission of sitting down with my pathetic cock to use the bathroom?" If a Mistress says yes then you say: "Thank you Mistress ____ for granting me the permission of letting me use my pathetic cock to use the bathroom. If a Mistress says no, then you say "Thank you Mistress ____ for not granting me permission to sit down with my pathetic cock to use the bathroom.

#18. We have full control over your cock. Anytime we feel it needs to be pumped by a penis pump, we will pump it and you will obey. Anytime we feel your cock needs to wear a chastity, you will wear it.

#19. You will lick the outer ring of the toilet to clean it. We are all shemales here. We use the bathroom cleanly and do not leave a mess. Any mess left by anyone in the house will be solely cleaned up by Jaymie.

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