The Pantysissy Diaries Ch. 01

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.

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Jay was on his way back to New York from a weeklong work conference in Chicago. He decided to take Amtrak back to NYC. He got on the train in Chicago and noticed a hot young blonde woman in her 20s sitting in the seats in the row directly to the right of him. She had a workout top on, and was wearing pink yoga pants. The seat directly to the right next of Jay was empty, as no passenger had bought that seat.

While in Chicago, Jay had made a panty run to his favorite store, Victoria's Secret. He picked up 3 pink thongs, 1 blue bikini panty, and 1 hot pink Hiphugger panty as part of Victoria's Secret's 5 for $27.50 panty sale. When he got on the train, he was still wearing the hot pink Hiphugger panty that he bought at Victoria's Secret. He hoped nobody could tell that he was wearing panties underneath his work clothes.

A couple hours into the train ride Jay decided to get up and use 1 of the 2 bathrooms that were on his car. (Both unisex). Once inside the bathroom, Jay pulled down his panties, and sat down to pee. (As a good Pantyboy always does). As he was peeing, the door to the bathroom suddenly barged open. It was the hot blonde woman sitting in the row next to him. Jay suddenly realized he must not have locked the door. Embarrassed, and gushing red beyond belief Jay immediately pulled up his panties and his pants.

"Sorry Ms. I must not have locked the door..."

"Don't be sorry. I'll just use the other bathroom." She said with a wink, and a dry smile on her face. She then walked into the bathroom next to the one Jay was using..

Jay finished peeing, pulled up his panties again, and nervously walked out of the bathroom and all the way down to the cafe car to grab some water. When he returned to his seat there was a message on a sticky note attached to it. It was written in pink pen and read: "Nice hiphuggers pantyboy! Ik your dirty little secret. Would you like to know mine? -Xoxo Sydney."

Jay felt a knot form in his stomach. This is exactly NOT what he wanted to have happen anywhere he wore panties, no less in a public setting like a train. Anytime Jay shopped for panties at Victoria's Secret he would always tell the cashier or store associate that he was shopping for his girlfriend. They would always believe him, and never in a million years did he think they thought he was shopping for himself. In fact, he had never been caught wearing panties anywhere before... Jay loved wearing panties, but he preferred to do so anonymously without anybody ever seeing him wearing them, or knowing that he wore them.. Not even Jay's girlfriend knew that he wore panties... His cover was most definitely blown this time though...

Jay read the note to himself and put the sticky note in his pocket. After he did that he turned to his right to look at Sydney, the woman who wrote it. She smiled back at him, and winked. "Oh shit, what have I gotten myself into?" Jay wondered to himself. Daytime turned into nighttime, and he eventually fell asleep.

When he woke up the next day Jay was not sitting alone. Sitting directly next to him was Sydney. Startled, Jay was at a loss for words when he realized who it was. Before he could say anything Sydney introduced herself.

"Hi, my name is Sydney. I came over here to get a better view of my... let's just call them... surroundings" she said with another wink.

"Hi, I'm Jay" was all that Jay could muster up...

The next few hours went by with Jay sitting in his seat alongside Sydney. It was awkward as hell, and Jay tried to pretend to himself that Sydney wasn't there. On top of that, Sydney had just put red lipstick on, and was in the process of doing her full makeup. Jay took out his earbuds and started listening to music for about an hour.

Suddenly Sydney took the earbud out of J's right ear. In a really sexy voice she whispered into Jay's ear "Hey Pantyboy, I saw you in the bathroom back there pulling up your pink panties. I know your dirty little secret. If you don't want this entire train car to figure out that you're a Pantyboy, I suggest you do exactly as I say."

"Yes m'am" Jay replied.

"No!" Sydney said affirmatively. "I'm not your m'am. You will address me as Mistress Sydney from now on. Understood?" "

Yes, Mistress Sydney" Jaymie replied.

"Good" Sydney responded. "And from now on your name is Jaymie. Understood?" "Yes, Mistress Sydney" Jaymie responded.

"So, Jaymie, where are you headed when you get off this train?"

"Uhh... I'm headed to New York City, Mistress Sydney" Jaymie replied reluctantly.

"Well, as a matter of fact so am I. Jaymie, when we get off this train in NYC, We will both head to my apartment.

"Ok, Mistress Sydney." Jaymie replied, as if he had any choice...

"Now Jaymie, those nails of yours look so plain and ugly. Let me get my nail polish out and brighten them up a bit. And since we both know pink is your favorite color, I think there's only 1 logical color choice."

Without further ado, Sydney took out her nail polish paints, and began applying hot pink nail polish to Jaymie's fingernails. At this point Jaymie was gushing red, hoping nobody on the train would notice what Sydney was doing to him. There were only a few people sitting in the vicinity of them, and for now they were all keeping to themselves.

"Now that's more like it!" Sydney declared, as she finished applying the hot pink nail polish to Jaymie's fingernails.

"But that's just your nails. Jaymie, I think it's time to make that face of yours a bit more sexy."

"Ok, Mistress Sydney" Jaymie gulped.

With that, Sydney took out the bright red lipstick she had been using and started pressing it on Jaymie's face.

"Now you look more like a girl, Jaymie."

All Jaymie could do was smile and sigh.

"But we still need to put some mascara on you."

Sydney then took a bottle of pink mascara and painted it on Jaymie's face.

"You look beautiful!" Sydney proclaimed.

"Now Jaymie, I think we need to take a selfie together, that I can send to my roommate."

Sydney then took out her iphone, and snapped a selfie with her and Jaymie's lipstick covered face.

"Please don't tweet that out" Jaymie begged Sydney.

"Oh don't worry Jaymie, this picture will stay within our house" Sydney replied.

"Our house?"

"Yes Jaymie, our house" Sydney said.

"Well, at least I don't have to worry about paying the rent on my apartment now." Jaymie thought to himself.

"Jaymie, I am a dress and lingerie designer at a fashion company in NYC. What exactly do you do?"

"I work at an investment bank in NYC" Jaymie replied.

"Interesting" Sydney said with another dry smile on her face.

"I think my company would have a field day with your wardrobe. What do you say pantyboy?"

"Yes... Mistress Sydney" was all Jaymie could get out.

"And I have a good feeling that your suitcase is all full of panties. Am I right?" Sydney asked.

"Yes... Mistress Sydney" Jaymie replied again.

"Excellent."

Soon after, the conductor walked down the aisle. She turned, looked at Sydney and saw Jaymie sitting there in full makeup.

"Having a good time, are we?" she asked.

"Yes, we're having a beautiful time" Sydney responded and squeezed Jaymie's arm.

"But Ms. we could use something to spice up this trip a bit" Sydney told the conductor.

"Ya know, I think I have just the thing for passengers looking to spice up their trip a bit. And please, call me Zoe."

Moments later Zoe the conductor returned holding a pair of red white and blue pair of panties that read "AMTRAK" on the front and "TRAIN ME" on the back in bedazzled red white and blue lettering.

Zoe then handed Sydney the panties.

"Will this do the trick?" she asked Sydney.

"Well I think that's perfect for my little pantyboy!" Sydney proclaimed!

"What do you think Jaymie?"

"Well...I think that's...uh... lovely Mistress Sydney."

"Now go be a good little pantyboy and go walk down the aisle to the bathroom. Take off your hiphuggers and put those on!" Sydney instructed Jaymie.

"Yes Mistress Sydney."

"And when you come back, I want you wearing nothing but your new Amtrak panties. OK?"

"Ok, Mistress Sydney."

"And do me a favor Jaymie, leave everything except your hiphuggers in the bathroom. OK?"

"Yes Mistress Sydney."

"And before you leave Jaymie, give me your iphone."

Jaymie handed Sydney his iphone and in exchange Sydney handed Jaymie his new Amtrak panties. Jaymie then walked down to the bathroom and did as instructed. He took off the hiphuggers, his work shirt, his work shoes, his work socks, and his work pants. He left everything except the hiphuggers and the Amtrak panties that he was now wearing, inside the bathroom. He then walked out of the bathroom and prepared to walk back to his seat. However, before he could begin his walk back, Zoe the conductor was at the front of the train car on the intercom.

"LADIES AND GENTLEMEN, MAY I HAVE YOUR ATTENTION PLEASE. WE HAVE A VERY SPECIAL GUEST ONBOARD THIS TRAIN CAR TODAY. NOW WALKING DOWN THE AISLE IS JAYMIE. JAYMIE IS BEGINNING HER NEW LIFE AS A SISSY TODAY. PLEASE TAKE OUT YOUR PHONES AND GIVE JAYMIE YOUR FULL ATTENTION AS SHE MAKES HER WAY DOWN THE AISLE."

EVERYBODY on board took out their phones and starting filming video and snapping pictures. But even before Jaymie could begin his march down the aisle back to his seat, Sydney had a pair of red high heel shoes passed down the aisles for Jaymie to wear. Attached to the heels was another sticky note with a message written in pink pen. "Hey Jaymie, I have arranged for your march down the aisle so EVERYBODY and I mean EVERYBODY can share in your true sissy initiation. But you didn't think you could just march back barefooted, did you? No, Jaymie, you need better footwear than just your feet. You will march down the aisle back to our seats wearing these Red high heeled shoes from Nordstrom. And you will do so wearing these hot pink stockings and pink garter belt that are both coming down the aisle in a second. And lastly I have arranged for a pink lace wedding cap to be sent down for you to wear. Enjoy your big walk, pantyboy! We'll all be watching! -Xoxo Sydney."

Jaymie had absolutely no choice. He had to do what Sydney said. He waited for the hot pink stockings as well as the pink garter belt and the pink lace wedding cap to be passed down the aisle. He put those on, and then put the red high heeled shoes on.

All throughout the car the women started chanting "JAYMIE! JAYMIE! JAYMIE!" followed with "PANTYBOY! PANTYBOY! PANTYBOY! And "SISSY! SISSY! SISSY!"

"Here goes nothing" Jaymie thought to himself. And with that he began his march down the aisle from the back of the car all the way back to his seat at the front of the car. Sydney had somehow arranged for all of the women sitting in the car to be seated all the way in the back where Jaymie had to begin his march. They all had their phones out snapping pictures, and some of them were even streaming Jaymie's march on YouTube and Facebook Live. Jaymie had no idea how to wear high heels, as he had never worn a pair before. Shortly after he began the march back he lost his footing and fell down flat on his face. There was a ton of laughter. Zoe the conductor then got on the loudspeaker again.

"CAN SOME WOMEN SEATED IN THE BACK PLEASE HELP OUR DEAR PANTYBOY GET UP?"

A few women sitting in the back handed their cameras off and helped Jaymie get up. 2 of them even whispered in Jaymie's ear.

"Nice stockings pantyboy" one of the women said and then started giggling.

The other woman whispered "You really do look good in pink, pantyboy" she said and gave Jaymie's rock hard cock a little tug through his Amtrak panties..

Jaymie continued his march back to his seat. He was getting towards the front of the train car when one woman stopped him.

"This is a gift from Sydney" she told him.

The woman then took out a pink stick of lipstick and started writing on Jaymie's chest

"Jaymie is a #Pantyboy." Then she put a pink Tiara crown on Jaymie's head. Finally Jaymie had made his way towards the front of the train. He thought the march was mercifully over, but he would be wrongly mistaken. The train suddenly stopped and Zoe got back on the intercom.

"LADIES AND GENTLEMEN, WE ARE STOPPING THIS TRAIN FOR A VERY SPECIAL PHOTO SESSION WITH OUR SPECIAL GUEST. ANYBODY WHO WANTS TO TAKE A PICTURE WITH OUR RESIDENT PANTYBOY, JAYMIE, PLEASE MAKE YOUR WAY TOWARD THE REAR OF THE TRAIN. JAYMIE WILL BE TAKING PICTURES WITH EVERYONE ONBOARD FOR ONE HOUR."

"Oh my god..." Jaymie thought to himself..

The line started forming and Zoe the conductor came down to escort Jaymie back towards the rear of the train. One by one people started taking pictures with Jaymie. The first person in line was a middle aged woman. She walked up to Jaymie dug her hand deep into Jaymie's panties and stood next to him for a picture. Jaymie could feel his throbbing cock tingling.

The woman told Jaymie "I'm not wearing any panties."

Once again, all Jaymie could do was smile. Next up was another woman. She had taken off her panties, but was still fully clothed aside from that. She came up to Jaymie and held the panties up to his face.

"Smell my panties, and I'll smell yours" she told him.

Again, Jaymie had no choice so he smelled the panties that the woman held up. They smelled like cum. She then smelled Jaymie's Amtrak panties and walked back to her seat. Next up was a guy who told Jaymie that he was gay. The guy kneeled down, and pointed to Jaymie's hard cock in his picture pose. Then he walked to the back of Jaymie and gave Jaymie's butt cheeks a hard two handed slap.

"I've always wanted to do that" he told Jaymie and then walked away.

Next in line were 2 young women. They both seemed pretty hungover and smelled of beer.

"Hi, I'm Amanda and this is Rachel. We both just turned 21" they told Jaymie.

"Hi ladies" was all Jaymie could get out.

"Turnaround pantyboy!" Amanda shouted at Jaymie.

"Oh, we're going train you alright" snickered Amanda as she read the back of Jaymie's "TRAIN ME" bedazzled Amtrak panties.

"Now bend over and keep your ass pointed!" yelled Rachel.

Jaymie did as he was told.

Amanda had Rachel take out a can of Bud Light. Rachel then poured the can of bud light down into Jaymie's Amtrak panties, and Amanda luge drank the beer from Jaymie's panties as it was being poured. After Amanda finished Rachel handed her another can of bud light.

"My turn now pantyboy!" declared Rachel.

Amanda poured the 2nd can of Bud Light down Jaymie's Amtrak panties, and Rachel luge drank the beer this time.

While they were doing this the woman behind them was filming it on her phone.

"This video is going to our entire sorority on group chat" Rachel told Jaymie.

Before leaving, both Amanda and Rachel grabbed both of Jaymie's balls with 1 hand, squeezing them hard, and making him squirm. They crouched down and took a selfie with Jaymie, making sure to get his beer soaked panties and the rest of his sissy covered body in the picture.

Further down the line was the conductor, Zoe, who originally gave Sydney Jaymie's Amtrak panties before his march. She came up to him, took the end of her conductor's whistle out of her mouth and dug it deep into Jaymie's beer soaked Amtrak panties. She crouched next to Jaymie to take a picture with one end of her conductor's whistle in her mouth, and then the other end dug deep into Jaymie's Amtrak panties.

"Welcome aboard Jaymie. I think Sydney has been very, very good to you today.." she whispered in Jaymie's ear. "If you're ever in need of somebody for a playmate, please give me a call. I live in NYC and gave Sydney my cell number. Who knows, I might even bring a few of my fellow black friends, so you can taste our BBC."

"Uh...will do, Zoe." Jaymie replied.

"That's Mistress Zoe to you, Pantyboy!" She told Jaymie.

"Will do Mistress Zoe" Jaymie replied again.

Zoe then kissed Jaymie on the lips and gave his cock a tug through his Amtrak panties and blew Jaymie a kiss as she walked back towards the front of the train.

Last in line for pictures with Jaymie was Sydney. She had an enormous smile on her face and was beaming ear to ear. She looked like she had just won the lottery.

"Hello Jaymie."

"Hello Mistress Sydney."

"Did you have a good time taking pictures?"

"Uhhh...Yes I did," Jaymie replied. "But I thought you said if I did exactly as you said, you wouldn't tell the entire train car that I'm a pantyboy.."

"I lied" Sydney replied with a grin on her face.

With that Sydney slipped a pink Victoria's Secret bra on to Jaymie's chest, and zipped it up on his back.

"You're favorite brand" she said with a smile.

Jaymie half-smiled back.

"Do you still have your pink hiphuggers that you were wearing earlier?"

"Yes, Mistress Sydney I still do" Jaymie told her as he handed Sydney the pink hiphuggers.

"Excellent. We'll need these for later" Sydney said with a grin on her face.

"Come on pantyboy it's time we head back to our seats and finish doing your nails."

"Ok, Mistress Sydney."

Sydney then led Jaymie back to their seats.

After the pictures ended, the train took off again, and was only an hour or so away from NYC. Sydney painted Jaymie's toenails with the same hot pink nail polish color that she painted his fingernails.

"You're now covered in hot pink from head to toe! Now what do you have to say for that?"

"Thank you Mistress Sydney."

"You're very welcome Jaymie. It's been a pleasure making you my pink sissy little Pantyboy. And we are only just getting started."

After his nails were done being painted Jaymie tried to close his eyes and get in one more nap, hoping there were no more surprises. But before he could fall asleep, Sydney had one more surprise left for him. She whispered in his ear in that same sexy voice again.

"So Jaymie, we obviously know about your little secret, but would you like to know about mine?"

"Uh, sure Mistress Sydney."

Sydney told Jaymie to get out of his seat and crouch down in front of her. Jaymie did as instructed. Sydney then pulled down her yoga pants a little bit, unveiling bright red panties, which immediately caused a tent to form in Jaymie's crotch. She then grabbed Jaymie's right hand and pushed it down her panties. Expecting to feel a nice wet pussy, Jaymie was in for quite the surprise. He could feel his right hand cupping around a set of balls, and then as Sydney pushed it down further, he could feel her shaft. Sydney then pulled Jaymie's face forward, and pushed it into her panties, making him suck her dick.

"That's right Jaymie, feel my rock hard tranny cock.. I'm a shemale."

Again at a loss for words, all Jaymie could do was smile. Soon after, the train pulled into NYC.

"Come on Jaymie, let's go to our apartment."

To be continued...

The author copyrights this chapter, as well as any past or future chapters of this series. The reproduction of any chapter or part of any chapter of The Pantyboy Diaries without the written permission of the author is expressly prohibited. This story is a work of fiction. All of the characters, their names and the places they visit, are purely from the imagination of the author. Any resemblance to persons, places, or things is not intentional and purely coincidental.