Author's Note: This is a substantial reworking of one of the first stories I published on Literotica under the original title of 'All Three Holes' in the Anal category. That was more of a simple stroke piece, but this version adds more context to the story and, hopefully, fixes some rookie mistakes I made.
1.
Katie stood outside the building and took a deep breath. This was it -- decision time. Enter or don't enter. Once she stepped through this door, she would inevitably be swept along by a torrent of events. She only had the vaguest of ideas of what awaited her. It might not be absolutely impossible to extract herself from the whirlpool of whatever she was getting herself into, but it wouldn't be easy. Now was the last moment when she could simply walk away.
She was a country girl at heart. She'd grown up in the sticks and then gone to university on an out-of-town campus. Cities intimidated her. But this wasn't just a city, it was the City. The very heart of the capital. Everything around her was either made of glass and steel and rose forty stories or more up or else it was made of white stone, had a blue plaque, and had been constructed when Britain controlled half the globe.
She'd gotten out at the St Paul's Underground station and spent the next twenty minutes trying to find a door that should have only taken her five. Finally, she was here at the address from the email, after asking three different people. She didn't know what she'd been expecting. It was all rather nondescript -- if such a word could be used for a house in the most expensive area of one of the most expensive cities in the world. True, the door reminded her more of the entrance to 10 Downing Street than anything else, but still, the building it entered into was surprisingly low -- only three stories high and narrowly squeezed in a row of ten just like it.
She decided to inspect the door closer. She checked again the number and then turned to the intercom. There were three buttons but only one had a name-card next to it. It simply said 'Collins'. That was the point that had been made very clear to her. This was a house, a residence. Despite appearances, it was not a business. She was a visitor. Whatever she might be asked to do she was not an employee.
And she certainly wasn't going to get paid.
She rang the bell. She found her hand had shot out and pressed it before she could overthink the action.
The intercom crackled. "Collin's Residence," said a voice that sounded female.
"Katie," she said. "Katie Matherson. I...I'm expected."
"Come on in."
There was a click and the door opened a fraction.
She pushed her way in. The building didn't feel much like a home. It felt cold and had little signs of life. The floor was a cold hard pattern of black and white stone tiles. On the left side was a narrow staircase with a bronze rail that led its way upstairs. On the right side, a corridor with a few closed doors stretched towards the back of the building.
"Hello?" called out Katie.
She heard the echo of footsteps coming towards her down the hall and a tall woman with short-cut hair appeared in front of her - Susan. She relaxed a little at the sight of a friendly face. The older woman was dressed much as she had been at their meeting a week ago - like a woman who did business and who meant business.
"Ah, Katie," said Susan, checking her watch. "So glad you could come. I thought you might have gotten cold feet."
"Er, no," said Katie, her face betraying how true that statement had nearly been.
"Come through here," Susan said, indicating the first door. As they entered she turned the light on and then went over the curtains and pulled them to. The room contained a coat rack, a fireplace, and a simple one-person desk with a chair and nothing else. Hung on the coat rack there was a dry-cleaners bag folded over and a pair of lady's formal shoes was tucked neatly beside it.
"First, read and sign this contract. It's as we discussed."
Katie studied it. It was indeed the one she'd been sent over the Internet except now it had specific names and dates. It had many clauses. Most of them said, in a number of different ways, that anything that happened here today was not ever to be discussed with anyone.
Susan waited silently, with no visible impatience, as Katie read the whole thing again. When she reached the end, she picked up the pen and signed it. Just like with the buzzer, she did it quickly lest she not do it at all.
"You have your test results?" asked Susan.
Katie reached into her bag and handed over an envelope headed with the name of her doctor's little surgery on the top. Susan took the letter out, read it, and then put it back without comment.
She studied Katie carefully. "Your make-up will do. I will put your hair up."
She produced a scrunchie and a number of pins and quickly had Katie's long flowing hair pinned up in a bun.
"You can leave any belongings here or if you would prefer I can put them in our safe."
"No, it's fine," said Katie.
"In which case please get undressed."
"Now?" asked Katie.
"I'm afraid I need to check you don't have any recording devices on your person."
Katie pulled off her clothes. She'd been told not to pay any particular attention to what to wear but had come dressed for a job interview anyway. When she had stripped down completely, Susan looked her over. She indicated the dry-cleaning bag. "Put those on. Call for me when you are ready."
Susan left and Katie unzipped the bag, laying its contents out one by one. It was a complete change of clothes. The neutral white set of knickers, the matching bra, and the brown tights were still in the packets. They were from an exclusive brand that boasted supplies to the royal family dating back decades. The business suit, consisting of a short, but respectable skirt and a blouse and jacket had had the shop labels removed but was also clearly brand new and of the highest quality.
Katie dressed herself quickly. It all fit perfectly. She had sent Susan her measurements last week. There was no mirror. She felt good but hated not being sure. Susan would tell her if anything was amiss, surely.
She leaned her head out the door. "Er, ready," she said.
Susan came out of the neighbouring room and inspected her again. She pulled a case out of her pocket and produced a pair of glasses. She took off the ones that Katie was wearing and replaced them. The new version was considerably more old school, squarer, and with thick black rims, but the prescription was exactly the same. Susan brushed some hair out of her face and then, gently grabbing her by the shoulder pads, adjusted the jacket slightly.
"There you go," she said. "Please go up the stairs and knock on the first door at the top."
Katie started the walk up the stairs step by step. She still couldn't believe she was here. It had started about two months ago. She'd downloaded a dating app, and after being inundated with the usual bragging and pleading losers, struck up a conversation with a businessman thirty years her senior. Their conversation had been respectful, had mostly been cultured, and had led Katie to say, eventually, that what she was after was a sexual adventure with an older man of wealth.
They'd lingered on that part for a considerable while -- weeks, in fact. The point that needed to be established was that Katie liked the idea of wealth, old money even, but she wasn't actually after any of it. She just found the idea sexy.
