Phillip sighed as he stood facing the front steps. It was a large house, with a dozen iron barred windows and made almost entirely out of stone. It was the kind of place he would never hope to afford.
The next part was a bit like ripping off a band aid, he supposed. It was better to get it over with quickly. However, he still stood at the stone steps, not moving. He was still on time, but he knew being late would probably make things worse, and he didn’t know how strict they were going to be. He laughed to himself. The fact that he would stand still here while knowing he was better off going forward was probably part off the reason he was here in the first place.
It was far from the first time he had been here. He had known the owner for years through his sister, and felt lucky that he had. However, the house, and the implication of wealth, seemed far more opposing now then ever before.
Of course, there were a lot of reasons he was here. Not studying for his university courses and letting himself get distracted was part of it. Showing up late, or not at all, to his work until he was fired and couldn’t pay for the courses he was failing anyway was another. Trying to cheat and hack the system to get his marks raised and his charges lowered was probably the biggest. Now, someone he only slightly knew had a blank check on his future, and he had know idea how she was going to cash it.
“Oh well,” he thought, and walked forward. There was nothing he could do to change it now. He had agreed to it, if somewhat under duress, he better get it over with.
He rang the doorbell.
The large wooden door opened, and a cherry, blond haired woman poked her head out.
“Hello Phillip,” she said, smiling. “Glad you could finally make it.”
“I’m still on time! See!?” He said, panicking and showing her his watch.
She giggled. Phillip realized she had been teasing him and glared. “Its alright. Come inside, and we will get started.”
“Yes Ms. Smith,” he said.
“Oh please, don’t give me that. Its Rebecca…”
Phillip smiled, ‘perhaps it won’t be that bad,’ he thought.
Rebecca was almost ten years his senior. She had come from a well to do family, studied business in university, then used her knowledge of stocks to build up the fortune she possessed now. She had known Phillip’s older sister in university, and the times he had met her she seemed to be his polar opposite- always on the run, always working, always seeming to be on the exact level of stress that let her stay calm while making her rush to get things done.
Phillip gulped in fear. Gingerly he walked into the house, and instantly yelped as he felt something hit the side of his leg.
“First thing first, lets get you out of those silly clothes.”
“What? Rebecca, what is that… OW!”
He yelped again as hit him, this time square on the bottom, with a thick leather rod.
'I said STRIP. You are to please and serve me as I want. You know the rules. So STRIP!"
“What? Is this some kind of sexual thing? I don’t know what… OW!”
“You’re going to strip because I’m going to tell you what to wear. You agreed to do what I said when you signed the contract, so do what I say or I’ll send you to jail or worse.”
“Ye… yes Rebecca.”
He quickly grabbed the hem of his shirt and tore it off. He reached down to his belt buckle and looked at Rebecca pleadingly. She raised an eyebrow, and he undid his belt.
Really, he had known this was coming. This part was essentially the same for everyone in his situation, and he knew it could be much worse. However, no amount of mental preparation prepared him for the embarrassment as he pulled his pants down and stripped bear in front of his new mistress for her inspection.
Once he was naked, Rebecca stood in front of him, looking him up and down and thinking.
"Hmmm… I have to say you’re in fairly good shape. I suppose that was one thing you were competent enough to think of.
He squirmed under her gaze. “Yes Rebecca.”
She walked around him, examining him and teasing him with the rod. She hit him hard across the bottom and he yelped again.
“Now, it seems SOMEONE’s been naughty, haven’t they.”
Another hit, another yelp. Phillip felt the lines glowing on his cheeks. “It seems someone waisted their time at university. Looking at naughty pictures when we should have been working, were we?”
Phillip blushed and didn’t answer. She chuckled and continued.
“And it seems then, instead of working or dealing with their problems, SOMEONE decided to try to cheat their way out, didn’t they?”
Another hit. “YES REBECCA!” he shouted.
“Then, that someone COULD have been lined up to go to jail, or even a subby school, weren’t they? Wouldn’t that have been fun? Ending up having to choose between months in a cell and a massive fine or having to wonder who your new trainer would be? Would that be fun?”
Another hit. “NO REBECCA!”
“And it seems that SOMEONE was LUCKY that their big sister knew someone who was willing to pay their way out of it, make a deal with the university, get lawyers to drop the charges, and all they had to do was show up a few times a month to help that person out. Isn’t that lucky?”
Another hit. “YES REBECCA!”
“And THEN, that SOMEONE was LATE! ON HIS FIRST DAY!”
“I WASN"T LATE I WAS… OW!” That hit was harder then the others.
“And who was that someone?”
“Exactly right. Can you imagine my surprise when the lazy, unmotivated younger brother of my friend Sarah ended up being the one who did all this? Can you imagine when I found out the guy who spent all his time playing games while his sister was working was the one who did this and got caught? Can you?” She was spanking him continuously now, emphasizing each word with a smack.
“OW! OW! Yes Rebecca!” He shouted, whinning.
“Exactly right.” She stopped spanking him and walked back to his front and rested the rod on his face, pushing into his cheek. “Now. As far as I can tell I am getting you out of a heck of a lot of trouble and not asking for much in return. So, you are going to do everything here. You’re not just going to clean and cook, I’m going to put my feet up and relax as you take care of every little thing, understood?”
“This,” she moved the rod around his cheeks. “Is my riding crop. It will let you know when you displease me, and I expect you to willingly bend over for it, understood?”
“And, since I paid you out of it when I could have paid much less for a maid service, I expect you to remember I’m doing you a favor. You are here for my pleasure and to serve me. If at any point you don’t like it, you can go back, find a way to pay back the money and take your chances in court, along with the additional charges off breaking your contract with me. Understood?”
“Good. Then come along.” She led him through the massive open foyer and up a wide, twisting flight of wooden stairs toward the second floor. The floors were thickly carpeted, and the walls were a golden color, as if to emphasize the wealth. She lead him down a hallway, and he glanced inside various doors they passed and at the large paintings she had hung in every open space. Was he going to have to clean this all?
It occurred to him that he still had know idea what was happening. He was still blushing, one hand in front trying to hide his nudity as the other rubbed his sore bottom. Was he going to be spanked like that every day? Would he have to clean naked? The thought made him shudder, but was still better then the alternative.
Finally he asked. “Rebecca, what am I going to be doing here? Am I… do you really want me naked all day? Do I have to be?”
She chuckled. “You’ll see in a second. Ah! Here we are!” She opened a sliding door to what he realized was a closet. “Don’t worry, I won’t expect you to be naked.”
He let out a sigh of relief, then suddenly caught it as he saw her reaching for a dress. Even worse, it was a french maids dress, complete with long silk stockings and a ridiculously short skirt.
“Wha… wha…” he tried to ask, but the words wouldn’t form.
She laughed again and pushed it into his hands. “YOU, my little sissy, are going to be my french maid. I had this made for your size and I can’t WAIT to see you in it.”
“But… but… can’t I just be naked all day?”
She spanked him again with the riding crop. “No. I told you, you are here to serve me. You wear what I want, do what I want, act the way I want…” She grabbed at her hair in frustration. Phillip stared at her, he never expected her to show such a raw display of emotion. Finally, she breathed deeply, lowered her hands and contiuned… “This isn’t going to work unless you listen. I’m sure neither of wants you to go to jail Phillip. Just do as I say, and we’ll get through, ok? Now put the dress on.”
He got dressed slowly, first pulling on the silken panities. He blushed as he saw them covering him, it was almost more embaressing then being naked. The smooth silkiness was something he never felt before, and something he was ashamed to admit he enjoyed. He pulled on the stockings next, then finally dropped the dress over his head.
He blushed. Sissy play was far from rare in these situations, and something he knew might happen, but the fact others had suffered in his place didn’t lessen the embaressment.
'Good sissy," she said. “Now, for the next part.”
She reached down to the bottom shelf of the closet and took something out. It was wide and square, and shone with plastic.
She handed it to him. It took him a moment to realize what it was- a pink diaper, decorated with rabbits and lambs.
“A d-diaper…” he stumbled. Sissy play was one thing, diapering was another. He had heared stories about it, dreading but never believing that he might end up as one of the poor, pathetic abdls, condemed to crawl around in full diapers for their master’s and mistress’s ammusment.
“Please don’t do this to me. Please don’t make me wear this. I’ll do anything, I’lll…” he stopped as he saw her laughing.
“Oh silly sissy, I’m not going to make you wear it.”
“No. You think I want to change your stinky diapers? I want the extra responsibility, as you get to play? I told you, I’m not going to do a single thing, and you are going to take care of me.”
“What?” he asked.
In repose, she opened the door beside the closet and flicked a switch. Inside was a giant nursery, painted in bright pastel colors with animals and cartoons all over the walls, and piled high with stuffed animals and toys. There was babyish furniture and clothing everywhere- a high chair, a play pen, even a changing table, all sized for an adult. Not just any adult he realized, but Rebecca. She giggled and skipped toward the centerpiece of the room- a massive gilded crib, piled high with pink sheets and stuffed animals. She picked up a stuffed doll and cuddled it closely.
“Don’t get it yet? Are you slow?” she laughed. “The diaper isn’t for you, its for me, Daddy.”