His First Skirt
Lee climbed into the car to find Ann sitting in the front passenger seat with another woman in the driving seat next to her.
The moment he sat down she turned and handed him a folder.
“We will get to the meeting in about fifteen minutes,” she said.
He began to browse through the papers, they appeared to be financial reports along with some sort of contract.
‘This is an important contract so remember your training on how to behave during a meeting,’
‘Hand me the documents as I ask for them promptly.’ she added.
‘Yes Ann’ Lee replied.
He had barely skimmed through the documents when they arrived at their destination, a very expensive looking hotel. Lee placed the papers into a leather folder.
‘You can get out here. I’ll park downstairs,’ said the other woman to Ann.
As Lee was about to get out of the car, he suddenly noticed that the pants looked and felt different from when he had previously worn them. They felt much softer and now seemed to have a fine ribbed texture. As he stepped onto the red carpet he felt a deluge of the luxurious material unfurl around him. It now dawned on him that he had been completely outwitted He wasn’t wearing the same pants, he was actually wearing a full length skirt.
‘Let’s go!” snapped Ann.
He followed her along the carpet up to the hotel doors. He could he his reflection in them as he approached and was transfixed by the graceful movement of the sumptuous ribbed knit fabric. It contrasted beautifully with figure hugging turtleneck. As they entered the lobby he could feel heads turning to look. Every step he made seemed to give rise to an explosion of the soft folds of the skirt which drew even more attention to him.
Ann glanced behind, smiling broadly. She seemed to be enjoying watching him squirm. He could feel his face burning in embarrassment.
Finally they arrived at a meeting room at the far end of the lobby. It was decorated with soft furnishing in pastel shades. There were two beautiful women were sat down on a sofa. They both stood to greet Ann as she entered.
‘This is Lee, one of my assistants,’ said Ann, gesturing towards him casually.
He smiled meekly, bowing his head in deference to them.
The three of them sat down on the two sofas facing each other. Lee looked around him, not knowing what to do.
‘Sit there,’ said Ann. Pointing to a pouffe next to the one of the sofas.
The three women began to discuss the contract.Lee sat attentively next to Ann, passing her documents right on cue.
The optics of the seating were no accident and were not lost on him. The pouffe on which he was sat much was much lower than the sofa, to the side and slightly behind Ann. It was obvious that he was now in a subservient role. Compounded by the fact he was wearing a skirt whilst she was wearing pants.
A wave of submissiveness began to wash over him. The softness of the white ribbed turtleneck and the gentle movement of the skirt every time he moved seemed to magnify the sensation. When a tray of tea was brought in, he was ordered to serve it to the women. He knelt down as he handed over the cups, giving a bob curtsy to them before taking his seat again. Ann nodded in approval.
Lee had began to fully assume his new role…