My sissy boss.

Craig was in his office at Lingerie International watching the wall clock his left drifting under his shirt stroking his soft hairless skin. He was waiting for five thirty knock-off time to come. His secretary Charlotte came in and asked if he needed anything else, and he gruffly replied that she could leave for the day. After he had witnessed Chantelle get in her car and go he disabled the security cameras and headed down to the warehouse and started to look through the boxes. He soon found the red lingerie set consisting of a red bra, red panties and red pantyhose. He took the clothes and headed back to his office and then quickly stripped out of his suit until he was naked. He pulled the red panties up his smooth legs and let them snap in place around his hips and the bra followed. He pulled the clasp around the front and did them up then turned it around his body until the clasp was in the middle of his back. Then he pulled the bra up and slid his arms through the straps. He then slowly and carefully pulled the red pantyhose up his legs letting them cover his panties and smooth legs. He then rubbed his legs together and ran his nylon-covered feet over his shins.

He moved to the locked filing cabinets and after unlocking them he pulled out a bag containing makeup and a blonde shoulder-length wig. Also in the bag was a white blouse, red jacket, red skirt and a pair of red four-inch heels. He headed to the female restroom which had a big mirror and started to do his make-up. He applied foundation and was happy that he did not need a beard mask as he had had his facial hair lasered so it could grow. Next came the blusher and eye shadow and mascara. Last was his lips which he coated in a deep red and then puckered up and smiled at his reflection as he pulled the wig on to finish the transformation. Then he picked up the white blouse and pulled it around himself then remember the breast forms which he inserted into the cups of the bra. Then he did up the blouse and stepped into the skirt with the zip at the front which he pulled up and then turned it around his waist smoothing it out. He stepped into the heels and put the jacket on and again smiled at his reflection in the mirror then headed out of the restroom to roam around his company.

While Craig was doing his transformation and unbeknownst to him Chantelle had looked in her bag and found that she had left her phone at the office. She spun her car around and headed back cursing herself and hoping that her boss had gone home. Ten minutes later she pulled up in the parking lot and taking her keys headed into the office. When she passed the cabinet that held the security recorders she noted the door open so she looked inside and saw that the recorder and cameras were off. She pushed the on button then turned to look at the monitors waiting for them to start up and she prayed that no one had broken in and disabled the system. As the cameras came online everything looked normal until all cameras were up and running, just as she was about to turn to head to her office she saw the women's restroom door open and a woman in red come out and start to walk around the building visiting the warehouse and the loading dock. The woman then headed through the packing department and orders department. Then she saw the woman heading for the offices so she quickly ran to her office and hid behind a pillar.

As she settled the woman came in and headed to the boss's office and she watched wondering if the woman was a spy looking for secrets. She waited a few minutes but the woman never came back out but she had left the door open a little. Chantelle removed her shoes and stealthily approached on her nyloned toes. When she got near the door she could see through the crack that the high-backed leather chair was facing away from the desk so she gently pushed the door open hoping that it did not creak. With no creaking and a gap big enough Chantelle sneaked in feeling the soft carpet on her nyloned feet and approached the desk and chair. When she was near enough she grabbed teh chair and spun it "Who the hell are you" and before the woman could reply Chantelle realised this was not a woman but her boss dressed in female clothes whose cheeks were beginning to turn red. "Chantelle I can explain I am going to a fancy dress party" Chantelle laughed and had her phone out filming her boss in his female clothes and his flushed cheeks "What are you doing Chantelle?" Chantelle chuckled "Oh just getting me some evidence."

" _Now boss if you do not want this video appearing on a porn site for crossdressers" Before Chantelle could finish "Craig butted in **" I will give you a raise and a longer paid vacation just do not show anyone" Chantelle smirked, " Oh I know you will boss and you I know you will do anything to prevent this coming to light." Chantelle turned the seat again getting a perfect shot for her phone as she filmed Craig in three hundred and sixty degrees" This is the day that your life belongs to me slut but I am going to give you a final free choice. I will allow you to pick a female name." Craig looked down then back up knowing deep in his heart and head that this is what he wanted to be caught dressed and then dominated. He looked into Chantelle's smiling eyes as she towered over him " I choose the name, Jenny". Chantelle smiled knowing that she had her boss by his no doubt small balls " Well Jenny starting tomorrow you will come to work dressed in your female underwear. You are to destroy all your male clothes accept your suits for now and make sure you come to work on time. When we are in your office you will address me as the boss and I will address you as whatever I like. Out of your office, it is Miss Jones"_**

"Oh by the way I have you on my phone but I also switched the security cameras back on so you are screwed. Now I am going home and I think you should go but get dressed in your male clothes or don't". As soon as Chantelle had left Craig headed to the restroom and stripped down to his lingerie then put on his male clothes after packing away his female clothes he headed back to his office passing the security cabinet and noted that new tapes had been installed then he knew Chantelle had evidence of him wandering the warehouse and building dressed as a woman. He took his keys and headed out to his car locking the building behind him. He got behind the wheel and headed home knowing that his PA had him by the proverbial balls. He also felt excitement at having been caught by his own PA. He approached his home and parked his car under the carport and after unlocking the door and disarming the alarm headed inside. He showered had a snack then dressed in his favourite nightgown and went to bed dreaming of the moment he was caught in his own office by his own PA who now owned him completely.__