Jamie’s Mistress         by: MartiB

 

Jamie silently slipped through the door at precisely 2:57AM. He checked his watch to verify that he had in fact, beaten the Mistress’s curfew. He quietly locked the door making doubly sure that the chain and deadbolt were secure. Mistress often reminded Jamie that this was a dangerous neighborhood.

Securely ensconced in the apartment, Jamie uttered and barely discernable sigh as he slipped out of the torture instruments that he’d been wearing since 8:30. Why did high heels have to be so uncomfortable? He wanted to argue with Mistress when she directed him to purchase and wear the shoes but he knew better than to argue once Mistress had her mind set on something. Her logic was, as usual, flawless. If he wanted to make money by turning tricks, he had to dress the part.

He looked at his image in the full length mirror positioned in the hallway. He still had it! Golden brown hair cut in an attractive pageboy style. A face that could only be described as pretty. Mistress’s strict diet and exercise program had reduced his weight from a manly 183 pounds to a more attractive 147 pounds. A perfect size eight!

Jamie picked up his shoes and softly tiptoed down the hall to the bedroom. He tossed the shoes into the open closet. As he removed his short tight red skirt he looked at the wardrobe he had accumulated over the past few years. He was sure that there were still a few items of male clothing in there, but he couldn’t identify them at the moment. He smiled as he remembered the first time Mistress had sent him to buy lingerie. He had followed instructions to the letter, walking into Victoria’s Secret at precisely 3:30 on a Saturday afternoon. He could just barely control his voice as he responded to the sales girls query. He made it through the explanation about how he wanted to be and feel more feminine and that he didn’t know his size. Thankfully the sales girl did not laugh. She smiled and giggled a lot but she didn’t laugh as she took Jamie on a fully narrated guided tour of the store. They stopped in each section where she asked if he wanted to buy any items form this table or that rack. By the time the tour ended they had developed quite a following. Jamie had an armload of items to purchase mostly suggested by the other ladies in the store. Several suggested that he model the items to "be sure they fit" but that was not part of Mistress’s instructions.

He finished undressing and moved to the bathroom and began the task of removing his slut paint as Mistress called his heavy, overdone, dramatic make-up. As his face emerged from under the layers of paint he reflected on how different he looked today compared to just a few short years ago. Shortly after he came under Mistress’s spell she began to orchestrate a series of subtle changes that now, taken in their entirety had given him a very feminine persona.

It all started with electrolysis to remove all traces of his beard. Four painful months of weekly treatments combined with the creams and lotions that Mistress prescribed had done wonders. He continued his beauty regimen religiously to this day. His flawless face looked almost perfect without any make-up. Of course, his appearance was aided through the skillful artistry of Ingrid who did his permanent cosmetics. Eyeliner, brows and lips were all enhanced to ensure he always looked great.

Jamie grimaced as he remembered the scene with Christine when he came home with permanent eyeliner. He told her he had a business trip when, in reality, he had lost his job three weeks earlier. He walked in to find an irate wife waiting at the door. She screamed at him. She demanded that he explain how he was going to support her and Robbie without a regular paycheck. She screamed at him for hiding the fact that he was fired and for continuing to spend, as she characterized it, like a drunken fool. Then, as she paused for breath, she finally noticed the changes in his face.

"Oh my God!" She cried. "What have you done? Are you some kind of a freak? How are you going to get a decent job when you look more like a woman than a man!"

Christine demanded that he leave that night. She had already moved the bulk of their savings to her own account. She did leave him with just enough for a month on his own.

Jamie left that night. Mistress told him to get this apartment in one of the seedier parts of town. Jamie had been by the place several times. He looked at the filthy "Vacant" sign and wondered who would ever live in that kind of place. It was quite a step down from his previous life but he still had Mistress to guide him.

Jamie finished washing and moisturizing. He located his nightie hanging on the back of the bathroom door. As the smooth silky material caressed his body Jamie’s small but functional member came erect. He was tempted to massage himself to a glorious climax but he knew Mistress would find out and punish him.

He grabbed his bulging purse as he headed for the kitchen. He poured a mug of water and placed it in the microwave to heat for tea. He grabbed the ledger from the top draw and sat at the table to record the evening’s transactions.

He opened his purse and dumped the crumpled wad of bills onto the table. He started to sort and count the bills. The hundred dollar bill had to be first. Jamie silently worked his lower jaw from side to side as he remembered earning that large payment. He was still sore and, no matter what the prick said afterwards, he had worked hard for that bill. Thank God Kenny was there to make sure there was no problem. He had tipped Kenny twenty for the assist and knew that he’d have to lay low for a few days until the visiting long shoreman went back home.

He continued counting and was pleased to see he made seven hundred and thirty seven dollars. Not bad for an evening’s work.

Next he opened the ledger to account for each dollar. He allocated 20% in tribute to Mistress for the honor of serving her. That’s $148. Another 20% to Christine and Robbie. One Hundred to the surgery fund. He was within thirty dollars of his breast implants. Another hundred for hormones and beauty aids. That left $241 for rent and food. He carefully recorded each transaction in the ledger. Mistress would inspect the books sometime during the day tomorrow and he didn't want to be punished for sloppy financial management.

He sat and sipped his tea thinking about his life both past and present. His life had changed in so many ways since Mistress had taken charge. He honestly couldn’t say things were better or worse now, just different.

He finished his tea and washed out the cup. One more task before he could head to bed. He retrieved the stiff ivory parchment from the top drawer. He wrote tomorrow’s date, no, make that today’s date across the top of the page. Right under the date he neatly printed "Jamie’s To Do List". He carefully numbered each item on the list. He paused several times trying to recall if there was something he’d forgotten. Satisfied that he had everything he placed the list squarely in the center of the table. The sun was just peeking above the horizon as Jamie trod off to bed. Again his thoughts turned to the state of his life. Overall, he was satisfied but there was one regret. He wished he could find a real mistress so he could stop pretending.

 

 

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