The Office Ch. 04

This time Tom stood motionless as he felt Hamilton slide the satin sheath back into place and fasten it firmly into place with a tight bow. The right cheek of Tom's face throbbed in a similar fashion to his rear and he could feel his face begin to flush with shame for having upset his Mistress.

"Now lower your skirt and clean my fingers of your milk." Hamilton held her palms flat before Tom as if she were at a petting zoo and Tom bent forward cleaning her fingers feverishly with his tongue. Hamilton waggled her fingers to allow Tom better access to each digit as she continued to tease him.

Hamilton pulled her fingers back without warning leaving Tom lapping at fresh air. "Enough." Tom stepped back and straightened his body shape, keeping his eyes lowered. "Leave me and return to your duties."

"Yes Mistress." Tom turned and headed out of Hamilton's office and back down the passageway to the reception desk. He returned to his seat but before he could return to his magazine his thoughts shut down, aided by the sedative that was automatically administered by the technician via the IV line in Tom's right arm.

The technician reached for her phone and pressed a series of the numbered buttons. After the sound of two buzzes the technician heard Hamilton's voice. "Yes?"

"The programme is complete."

"Results?"

"Measurements looked positive."

"Have five brought to me when you've completed your closeout procedure." Hamilton replaced the receiver without awaiting a response. She checked her watch and determined that she had at least fifteen minutes to kill and returned to the report she had been reading on her desk.

When Hamilton heard a knock at her door she knew her estimate had been near perfect. "Enter."

The technician opened the door and entered a few paces into the room holding the door open enough for Tom to walk past her before she closed the door behind him leaving Tom alone with Hamilton.

Hamilton took a moment to peruse Tom as he stood close to the entrance of the room. His hair was naturally longer than it had been when Hamilton had first taken ownership of him several weeks earlier, but Hamilton's assessment was more surgical. Both financial and physical, as any enhancements that Hamilton deemed worthy of her slave, to exaggerate her latest acquisition's enforced femininity, would need to be recouped in some manner. Which is why Hamilton had to ensure that her latest acquisition was ready for the next stage of his transformation.

"Come closer Sissy Tom." Tom took several steps towards Hamilton's desk, keeping his head lowered as he did so. Hamilton got up from behind her desk and slowly walked around the timid figure. Hamilton could hear that his breath was becoming ragged as she did so, his shoulders rising and falling in an uncontrolled fashion within his pink knee length satin kimono. "Do I scare you sissy?"

"Yes Mistress." Hamilton smiled and continued to slowly circle.

"Why?" Hamilton said firmly, holding back her mirth.

"Because you are my Mistress."

"Should you be scared of your Mistress, sissy?" Hamilton said, now holding her position behind him.

"Always Mistress."

"Do you believe that a Mistress should punish her sissy?"

"Always Mistress."

"I see. What if I chose to...chastise you instead Sissy Tom?" Instantly Tom whimpered and slowly bent forward. He lifted his kimono hem so that his rear was exposed giving Hamilton full view of the pink suspenders that held his black fully fashioned stockings in place and the thin strip of his pink satin thong which disappeared between the cheeks of his ass.

"Sissy Tom always deserves to be chastised Mistress."

"Of course you do."