The Annual Appointment: Part 1

Amy had been visiting him for 10 years, but she still didn't know his name. She hadn't even asked. The contract was very clear that he decides what they talk about on June 12th every year - the only day they were allowed to see each other.

Today was June 12th, and she was ready. Waiting a full year between seeing him was torture, but time never moved slower than on the morning of the 12th.

She opened her purse for the fourth time and made sure she had everything she needed. His requests were surprising this year, and it had taken her four days to assemble everything, but it was all there.

She allowed herself to daydream about how it all began.

***

Her old roommate Tess had put her up to it a lifetime ago.

Tess' day was March 22nd, and its effect on her was obvious the next morning. Amy had been sitting in her favourite seat by the window drinking her morning coffee and reading a fantasy book when a black sedan pulled up and her roommate spilled out.

It wasn't unusual for Tess to arrive late after an overnight tryst, her chestnut brown hair a tousled mess, but this morning was different. Before the front door was even closed behind her, Tess had found Amy and pulled the book from her hand.

Their eyes locked, and Amy saw an insatiable hunger there. A lip bite and the slightest of nods from Amy was enough for Tess to seize control and turn their friendship into something else.

Between Tess' fifth and sixth orgasm that day, she told her friend all about the arrangement.

Amy submitted an application the next day.

***

When you have an assigned day, all you can do is wait for it. The contract stipulates only three responsibilities in advance of the annual event.

The first was a questionnaire, identical every year since year two. Amy had to write her responses by hand and send them to a post office box one month before her appointment. The five questions were:

1) Will you be keeping your appointment this year?

2) Are there any changes to your limits since last year?

3) What moment from last year's session do you think about the most, and why?

4) Describe, in detail, a recent fantasy that you have masturbated to.

5) Did you have an orgasm while writing your responses to these questions?

The answer to question five was always 'yes'. Amy would touch herself with her left hand while writing with her right, and she would mark a star on the paper to indicate the moment when she had climaxed. This year's version of her letter had three stars on it. The fantasy had been very detailed.

In the envelope with the responses, Amy was required to include a recent health test proving a clean bill of sexual health.

The final responsibility was following a list of Instructions that would arrive by mail a week in advance. These changed every time, and could be difficult to complete in time for the appointment.

If you fail to follow any of the advanced instructions, you lose your day forever.

If you miss your day once, you lose your day forever.

Amy could do whatever she wanted for the rest of the year, but on every June 12th she was his for exactly 24 hours.

And that's precisely what she wanted.

***

The correspondence had been more detailed in year one. Amy had to write a letter professing her interest, and that led to an interview of sorts.

The initial response, signed only "Sir", described an outfit that she would have to assemble and wear to a mall across town on a busy Saturday afternoon. Amy and Tess raided their closets and met the request for a green blouse and a black pleated skirt over top of a matching set of black panties and a bra.

He must have been there, but she didn't spot him as she walked to the bench by the elevators and found the note taped underneath that she'd been instructed to retrieve.

The note told her to go into a changing room at the GAP, slide off her panties under her skirt, and touch herself until she was on the brink of orgasm before returning to the mall floor and shopping for another hour.

That afternoon was thrilling, knowing that he was out there somewhere watching her while she went store to store carrying her panties in her purse.

When time was finally up, Tess was waiting at home in her cutest black negligee, ready to be attacked.

He must have been impressed, because another letter arrived a week later requesting her to outline her interest and experience in a long list of kinks. Not long after, he sent her a draft list of rules to follow and an appointment for June 12th.

***

Her first appointment was the only time Amy had considered walking away.

The sedan had driven her across town on a Saturday to an empty office building and left her outside the lobby with written instructions to take the elevator to the tenth floor.

Inside the empty, sterile building, the task ahead felt overwhelming. Was she really going to give herself over to a stranger she hadn't met?

She paced back and forth, and nibbled on her fingernails, but the curiosity was too much in the end. She wanted to know how it would feel to totally give up control, and she needed to know if she'd be able to do it.

Upstairs, Amy found an empty floor of conference rooms, with signs directing her to a door at the end of the hall. Heart in her throat, she turned the handle only to find another empty room with a single chair and a small table, where she found a copy of the negotiated contract.

The entire wall in front of the desk was a two-way mirror. An intercom crackled to life, and a firm, but warm voice invited her to take a seat. He was watching her.

Over the course of the afternoon, the disembodied voice talked her through every aspect of the contract. She was surprised by how fastidious he was about the smallest details, pausing to clarify with questions she'd never been asked before.

There was something incredibly intimate about laying bare her most secret kinks and desires to an invisible stranger. Nothing was off limits, and she never felt judged by him, only empowered to finally give voice to her most animalistic desires.

When the time came for her to sign the contract, she was soaking wet and ready for action. He directed her to move aside the table, and then open the top drawer of a filing cabinet in the back of the room where she found an assortment of sex toys to choose from.

Amy chose a wand massager and it was immediately put to use. While her new master directed from behind the two-way mirror, she stripped, sat down in front of him and brought herself to completion, filling the empty office building with carnal moans.

***

That evening, the adventure continued at a hotel across the street. A room key from the same filing cabinet allowed her entrance to the presidential suite, where she found champagne, flowers and a half dozen video cameras. He had really taken to heart her written confessions that she liked to be watched.

A handwritten note briefed her on the game for the night. She was to change into a bathrobe while he watched on camera, and wait for room service to deliver dinner. There was a light operated by remote control in the bedroom, and she had until dinner was finished to memorize a list of different tasks to do depending on what color the light changed to. They were:

Blue: Take a bath

Green: Get naked and kneel

White: Put your clothes back on

Purple: Hold ice from the champagne bucket against your nipples

Yellow: Find a gag to wear in your mouth

Orange: Rub your clit

Pink: Fuck yourself with a dildo

Red: Cum

Off: Go to Sleep

She did everything he asked, and rather than feeling timid in front of the cameras, she found herself performing for them and moving them to give him better angles. A total stranger was controlling her every action without uttering a word and she was already addicted to serving this man.

In her year two questionnaire, Amy would say her favourite memory of the night was taking a bath for him. She moved a second camera in to the washroom so he could see her from two angles as she soaped up her breasts and began to play with them in front of the cameras.

The door had been left open so Amy could see the light in the bedroom from the bath, and when her nipples grew hard under her touch, it turned green.

Eager to please, she pushed herself up out of the bathtub, spilling water on the ceramic floor as she rushed to kneel in front of a camcorder. She locked eyes with the flip screen and saw herself looking back confidently, water and suds sliding off of her breasts to pool at her knees. It was a version of herself she had never seen before.

An orange light flashed, and she watched herself feel her clit in that position, mouth agape as her passion erupted out of her in moans. There was no way of knowing for sure, but she was forever convinced that somewhere else in the hotel he came watching her in that position before flicking the light back to blue so she could finish her bath.

In fact, the certainty she felt in that moment that he was turned on by her was what made that moment her favourite part of the night. She would say that in her questionnaire later on, and he found ways to give her the same confident feeling in their future sessions.

The only downside was that he liked to tease. Every time the light turned orange or pink she reached the edge of a climax, but he always changed colors right when she was about to lose control, and the light turned off for the night without ever turning red.

It was the same story in the morning. He brought her close to orgasm three more times before their 24 hours ran out, but he never let her cum, even when she started pleading into the cameras.

Amy called Tess during the car ride home and ordered her roommate to cancel her plans for the afternoon so they could fuck non-stop.

Later that week, Amy bought a red light for her bedroom.

Every time she masturbated for the next 364 days, she would turn the red light on and daydream about his voice telling her to cum over an intercom.

***

The sound of a car brought Amy back to reality, and she looked out the window to see a black sedan pulling into her driveway. A shiver of anticipation ran through her body as she opened the door and stepped outside.

A few words were exchanged with the sedan driver before Amy opened the door to the back seat, but she knew better than to ask about this year's destination - if he wanted her to know, it would have been in her instructions.

There was a gift on the back seat: a box wrapped in pink paper with a red bow and a tag. He hadn't mentioned this in his instructions.

The tag read:

"WAIT 30 MINUTES BEFORE OPENING. FURTHER INSTRUCTIONS INSIDE."

She set a timer on her phone and settled in.

The best day of the year was about to begin.

(to be continued...)