Wonderful World of Pornography Ch. 04

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Isaac learns to dress up.
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*This is a filler chapter for some more detail about Isaac's training*

Isaac was woken from his nap by Kali. She shook him violently as she got out and waited for him to get out. He stood there for a few seconds just looking at the large store front lit up with bright lights, SISSYS R US. Kali smiles looking at him, seeing his sudden interest, and begins walking inside.

"Come on now! I have a changing room reserved for us."

Isaac follows behind her as some of the sales people greet her warmly, most ignore him as he just stares at all the toys and clothes on racks upon racks upon racks. He doesn't say anything but it is clear that he is interested in a lot of the dildos. They continue to walk to the end of the store with large private cubicles. The door is opened for Kali and Isaac and they enter to see a clothes rack with many pink, shiny, frilly, girly clothes. Kali sits down in one of the comfortable chairs.

"Let's begin, shall we. Stand on the podium and try on the clothes I give you."

Isaac nods and gets on the podium. Kali relaxes and leans back, before grabbing a schoolgirls uniform and throwing it to him. He puts it on. The black panties it comes with barely fit him and he blushes as his dicklet gets hard as he forces it on. The blue skirt is long enough to just barely cover his bulge. He pulls on the long socks and gloves and looks around for a shirt but there is none, instead just a scarf that shows of his beautiful feminine chest. Once done, he looks to Kali for approval. She sighs and gets up, grabbing some more clothes and placing them next to him. She grabs the waist band of the skirt and pulls it up further.

"You have to look like a sissy! Don't you want to get more cock?"

"Y-yes I do," he murmurs softly

"Then you will have to show off your body!" She laughed in her head, knowing that it wouldn't be too long until he was completely broken.

"Like this?" He posed for her, showing off his ass.

"Good! Just like that" She spanked his cheeks that were hanging out between the now barely visible panties. He smiled, enjoying it a little.

"Now try these as well."

She hands him a bunch of clothes and sits back down. The first is a cheerleading outfit. All pink with a pair of yellow pompoms. Isaac kept the panties on and changed into them, pulling up the skirt, smiling and enjoying as he put on a show for Kali, bending over and showing her how well trained he was. She smiled and pointed to the next clothes. Kali was enjoying her time with Isaac, not wanting to stop.

Next were three sets swimwear. The first a white one piece. Isaac didn't seem to like it as it showed off the silhouette of his dick and it was too tight, he then tried on the green two piece which was again too tight and Kali noticed him wincing as he modeled it for her. She pointed to him to just try the next one. He grabbed the black bikini and put it on. It was very comfortable compared to his last two. The bottom was designed in a way that his cock slid under him yet the base could be seen easily, and the top was a bit snug and wrapped up just a little more than his nipples. He smiled as he spun around and posed modeling for Kali.

"You're enjoying this?" Kali asked as she sat up straighter.

"Yes, I am ma'am!" Isaac smiled back.

"That means you're learning well! Now let's see you in this for regular days?"

She threw him a brown short dress with a turtle neck. Unlike the rest, it doesn't particularly show off his ass or dick, however, it does show of his physique especially his legs. Isaac looked at it and put it on quickly.

"This looks so cute! I love it!"

"You should, this is what I want you to wear from now on! I have also already paid for everything and put it on the studios tab, so you better not mess up." She grinned as she walked over to him, grabbing his ass cheeks as she handed him her phone. "Now take a picture for me, and I want to see you showing off."

Isaac blushes a little. Even though he has gotten braver, he does have a shy side. He turns to the mirror and lifts up his dress, showing his tiny little cock and clicks the picture. He hands back the phone and after a few taps, Kali leans down and puts on a new cage, The Shrinker®. She heads towards the door and points to another stack of clothes.

"I'm leaving, my friend will pick you up soon," as she speaks her phone is blowing up with messages, "Try on the rest of the clothes and be sure to pack them up when you leave, they are studio property!"

Isaac nodded "Thank you so much for this!"

"Its okay, just remember to take care of my friend, and be as slutty as you can!"

"Yes ma'am!"

Kali left, a bit sad she couldn't see him try on more clothes. Isaac went through all the clothes, a bunny maid outfit, nurses outfit, multiple bikinis and dresses but the one he liked most was a set of black women's underwear, emboldened with the name of his favorite porn series, 'Black Elf'. He tried it on, it was designed to show off his cage and thighs. He couldn't help but giggle like a girl as he looked at himself in the mirror until there was a sudden knock on the door.

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Jonathan72Jonathan726 months ago

I love your stories, I just wish they were longer.

Jonathan72Jonathan726 months ago

I love your stories, I just wish that they were longer

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