His First Skirt: Part One

His First Skirt

Part One

Turtleneck, Ruffle Front Duster and Long Skirt
Ribbed turtleneck, ruffle front duster & floor length skirt

Many of our regular readers were keen to know more about the ImageMax programme here at Sentinal after reading our Skirting The Issue article. So with that in mind here is an exclusive follow up which takes us through to the crucial next step that our interns must navigate in order to graduate!

As we have mentioned previously, getting a trainee into a skirt for the first time can be a delicate process. Some gentle persuasion is usually all that is required but on occasion,  we simply have to force the issue.

Thankfully we have developed several very effective ways to overcome any resistance.

The Skirt Switch

Lee was one of our more rebellious interns who had somehow managed to dodge their way through the programme. His name had come up in a progress meeting and Ann, our Senior Assessment Director had decided it was now the time to shorten his leash.

‘One of our interns was due to assist me at a meeting with one of our clients as part of their assessment.’ Ann explains. ‘Instead we decided to assign Lee to the task. It would be a perfect opportunity to set a trap for him and see how he reacted.’

Poor Lee had no idea what was about to happen that morning as he  assisted Tanika with what appeared to be a routine stock take. He was about halfway through it when Mika walked in, ‘Hi Tanika, we need someone to attend to one of the senior directors at a meeting this afternoon.’

Of course they both knew exactly who they had in mind.  They both turned to Lee who immediately began to look a little nervous.

‘Lee!’ said Tanika, snapping her fingers, ‘You can finish the stock take tomorrow. Mika will take you downstairs to get ready for the meeting.’

Lee followed Mika down the corridor.

‘Have you attended one of these meetings before?’ she said casually. Lee shook his head. ‘You will attend to Ann, the senior assessor.’

‘So make sure you follow all her instructions.’

Of course Mika already knew this was his first meeting and that mentioning Ann’s name would put him on edge. Ann was a strict disciplinarian and all the interns knew not to cross her.

As they entered the studio Mika directed him to the changing room. ‘Take a quick shower.’ ‘You’ll have to look more presentable for this meeting.’ she said, handing him a robe.

When he had finished he walked into the studio. Mika was waiting for him along with Tanika and her team.

‘Okay, let’s go!’ snapped Mika. ‘You only have a few minutes before they  leave.’

He walked hurriedly over to them and took off his robe. Tanika handed him a pair of plain black panties. ‘Put those on.’ she said.

She then took a pair of black opaque tights, ‘Step into these.’

He hesitated ‘I don’t wear…’

‘This is what Ann instructed!’ she said, cutting him off mid-sentence.

He stepped into them without saying another word. Tanika pulled them up around his waist, ‘Look at these.’ Lee looked up to see a pair of brown ankle boots with a high stiletto heel.

’Gorgeous aren’t they?’ He nodded, again without saying a word.

‘Now, you have worn these Rachel Pally pants before haven’t you?’ said Tanika holding up a pair of brown wide leg pants.

‘Yes I have,’ he said. Sounding almost relieved to see them.

‘We are going to pair these with this gorgeous turtleneck.’

‘Hold you arms up.’ Said Tanika.

Lee raised his arms and Tanika slowly pulled the ribbed turtleneck down around his body. The neck was luxuriously long and tight fitting. He tilted his head back and closed his eyes as Tanika folded it around his neck. Just at that moment Mika whispered in his ear from behind, ‘Step into the pants.’

He was so distracted by everything happening around him that he didn’t notice she had cunningly swapped the pants for a full length skirt in the identical color at the last moment. She pulled the form fitting turtleneck down around his hips over the long skirt. He glanced at himself in the mirror. From a distance the skirt looked identical to the pants he had worn before.

Pants To Skirt
From pants to a skirt in one step!

‘Okay they are leaving now.’ said Tanika.

Before he knew what had happened, he was whisked downstairs and into a waiting car in the basement car park.

Tanika and Mika high-fived each other as the car pulled away.

‘Nailed him!’ They yelled in unison……


Continued Here!

Xuxa x



4 Thoughts

  1. Hi, it’s uncanny how close our love of elegant skirts and deep collared ribbed turtlenecks is. I very much enjoy your new posts. Keep up the great work Image Max! Thea x

    Liked by 1 person

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