Panty Boy Halloween

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Part One

An Invitation of Sorts

It had been seven months since he had met his Mistress. What started as ‘just a job’ had turned into a life-altering adventure. Everything he did now was controlled by the woman he called ‘Mistress.’ Everything.

He had always been fascinated by panties. Mistress told him that all men are, that all men are jealous of the pretty things women get to wear. It starts when you are little boys, she had told him. You see those ruffled, frilly little panties that the girls around you are wearing and you become jealous and resent the fact that you have to wear those ugly, plain boy underpants.

It was true, thought PantyBoy. He had always wanted a pair of lacy little panties with bows and ruffles when he was younger. He even stole a pair of panties from his cousin during a summer visit.

They were white cotton with yellow and black bumblebees and they fit him like they were his. He wore them under his play clothes sometimes and to bed, where he would imagine himself dressed in them and a little sundress playing hopscotch with the little girls on the playground.

His fascination with panties continued on through his formative years and his collection of catalogs and the occasional magazine that featured photos of boys in panties grew.

He didn’t understand his obsession, but he explored it. He would wear panties under his clothes and could barely contain himself as the sensuous material rubbed against his balls and cock.

He found a treasure trove of websites that catered to his fetish and he ‘met’ other panty enthusiasts on-line and together they would discuss their love for all things satiny and feminine.

Once he even found a pair of cotton panties that reminded him of the first pair he had ever worn. They were decorated in a juvenile design that made him think about all those boyhood dreams about being on the playground, his little sundress rising and falling, allowing little glimpses of his cute little panties.

Mistress said she knew right away that he was a pantyboy. He tried to deny it but in the end she won and he submitted to her will and power.

He was hers to do what she wanted, as long as she allowed him to dress in panties. And she did. All kinds. Satiny and cotton panties. Lacy and ruffled and in all colors.

Mistress controlled every aspect of their relationship, especially their sexual relationship. After crawling between her legs and pleasuring her with his very talented tongue, only then was PantyBoy allowed to slide down his panties and enter her.

Sometimes she just wanted to see him play with himself through his girlish underthings until he exploded inside them. Then she would stuff the soaked panties into his quivering mouth as she spanked him over her knee.

The rules were always the same for PantyBoy. He was to keep his body clean shaven. He was not Pendik Yabancı Escort allowed to get a haircut unless Mistress had made the appointment at a salon of her choosing.

He was to always be in panties and no longer owned any male underwear.

He was not allowed to watch any sort of pornographic movies unless she had made the selection and they watched the movies together.

These rules were not to be broken for PantyBoy understood that retribution would be swift and harsh.

Punishment took many forms. There were the over-spankings in very childish looking cotton panties. Afterwards she would make him stand in the corner, facing the wall, red bottom exposed and thumb in his mouth.

Sometimes she would threaten to bring friends over to see him in just his panties. This frightened him and turned him on as well. The thought of strangers seeing him in his pretty panties made his heart race and his cock strain against his satin treasures.

Once she made him take a bubble bath and shave his body smooth. Afterwards she dusted his body with a sweet smelling talc and then had him bend over the footboard of her king-sized bed.

She played with his smooth ass and then he felt a cold finger slip inside him. It was the first time she had done this and she drove him to new levels of delight and torment. After loosening him up, Mistress slipped a small plug into his virgin hole and turned on the vibrator inside the faux black phallus.

He came right there and then into her waiting hand. Smiling she pushed her glazed fingers into his mouth. He wanted to protest but he knew he shouldn’t…couldn’t.

When his body stopped shaking, Mistress slipped a pair of ultra-feminine panties up his smooth legs and into place, leaving the vibrating plug not only still inside him, but on.

The sensations of the fake cock buzzing in his no longer virgin boy-pussy, as she called it, and those oink satin panties, kept him in a state of euphoria.

He also noticed that he walked a little differently now, standing straighter with his butt pushed out a little. He also took smaller steps, ensuring the plug stayed inside him, pleasuring him.

After he dressed in a pair of her sweatpants, pink with the word ‘BRAT’ written across the seat, and a tight t-shirt, she took him for a ride across town.

His heart raced. Not only because he had no idea where they were going, but because he was now sitting and the his weight forced the plug inside him to deeper regions, touching on the sissy inside him and stirring a new whole world of sensations and thoughts.

Their destination, as he soon discovered, was a nail salon. Mistress talked to the Asian woman who managed the place and within minutes PantyBoy was receiving his first pedicure. All the while there was a small vibrator driving him wild.

Occasionally the girls Pendik Yeni Escort who were attending to him looked at him and then giggled like schoolgirls and he was sure they knew what was going on his pink sweatpants.

It made him hard to know that a woman had dressed him in panties and these women who were making his feet pretty knew he was just a panty sissy.

He came silently and didn’t care at that point if anyone knew.

When they returned home, Mistress commended him on his behavior and rewarded him by letting him tongue her to an awesome orgasm. She removed the plug from his bottom, bathed him gently, and then dressed him in a pair of cotton panties and nightshirt.

His dreams that night were wild and erotic and scary and incredible.

Mistress had awoken something inside him and he wondered where this adventure would take him.

It was not a month or two later and when the slender young man got home from work he quickly removed his clothes and left them in a pile on his bedroom floor.

He examined his body and decided it was time for a shave. He filled the large tub with sweet-smelling bath salts and after soaking in the relaxing bath, surrounded by candlelight, he shaved himself baby smooth, paying close attention to his butt and crotch.

Mistress liked that and she would call him ‘her smooth little pantyboy baby.’

Letting the water drain from the tub, he dried himself and wrapped a towel around his slender smooth body.

In his bedroom he went to his dresser and looked for the perfect thing to wear, choosing finally on a pair of light blue cotton panties and a matching tank top.

He had always kept his hair short, but now it reached to the tops of his shoulders. He pulled it back into a ponytail and held it with a pink scrunchie.

White bobby socks completed his ‘comfy-lay around-the-house’ look and he grabbed his laptop and went into the living room with a glass of wine.

When he opened his email he found one in particular that caught his eye. It was an email from his mistress and he opened it immediately.

This is what it said:

“My dearest Panty-Boy. As you know this weekend is Halloween. I know you’ve been dying to know what our plans are and I’ve decided to not make you wait any longer.

On Friday you will be met after work by three associates of mine. These ‘girls’ are going to prepare you for the party on Saturday.



If I hear otherwise, your punishment will be swift and harsh.

There better not be any questions.

Now be a good little pantyboy for mistress and grab one of your toys from your special drawer. I think the black dildo would be perfect. I KNOW that one is your favorite.

***Weeks Pendik Masaj Salonu earlier Mistress had made PantyBoy go into an adult bookstore and buy a large version of his first dildo. This one resembled a thick black cock and had realistic veins running along the sides. He had to make sure he asked the salesclerk, a handsome black man who looked as though he was sporting something quite similar between his legs, all sorts of questions about the dildo he was buying.

It was humiliating and scary and it turned on PantyBoy to be talking to this man, while wearing panties and buying a dildo that would be inside his hungry boy-pussy within the hour. Mistress had even encouraged her willing pupil to flirt a little and by the look on the dark-skinned man’s face, PantyBoy was doing a good job.

Later, as Mistress slid the faux black cock inside him later, PantyBoy couldn’t help himself from thinking it was the salesclerk who was behind him, fucking him with ever-increasing thrusts.***

The email continued, “Once you have your pacifier, I want you lay back on the bed in your just prettiest panties.

Then take that black cock and press it to your mouth. I then want you to kiss it and slide it past those soft lips of yours. Close your eyes and slide it in and out of your mouth, ever so slowly. Suck on it, pretending it is a big black cock…imagine it to be his big black.**

Pantyboy knew exactly who she was talking about.

“Pretend it’s his cock,” she had said, “and my dear PantyBoy, make that big, black cock good and wet and slippery.

Just make your special toy nice and wet and get on all fours. Do not take your panties off, just slide them down a little as you press your toy against your boy-pussy. Just work around them as you slide your toy…his thick black cock into your boy-pussy…ever-so-slowly.”

Now I want you to fuck yourself, all the while with your eyes closed and with thoughts of that muscular black man having his way with you…pounding into that sweet little boy-pussy of yours.

Just think about that big black cock fucking your little hole and allow yourself to cum into the front of your panties. Soak your panties with that sissy cream.


Just think about that black cock fucking you. THAT SHOULD BE ENOUGH. Don’t you think, Precious?

When you have cum, I want you to put your panties in your mouth and suck on them and clean them. Then I want you to pull out your toy, clean it, and put it back in your toybox.

Put on some clean cotton panties and a nightshirt and go to sleep.

I will see you on Saturday and we shall have the best Halloween ever.

Sweet dreams, my baby. My PantyBoy


By the time the pantyboy had closed his laptop and retrieved his special toy from the drawer in his dresser, the front of his panties were wet and sticky and his heart was racing.

Afterward, after following Mistress demands to the letter, as he drifted off to sleep, his bottom still quivering from the night’s action, he thought about what Mistress might have planned for him and his cock began to stir.

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