After the exhibition opening and its success, Diane was my sex slave for the weekend. She was able to complete her challenge of having her allowance of exactly 10 orgasms. (I will tell you what happened sometime in the future.)
Over breakfast on the Monday morning she asked “Can we do our version of an Advent Calendar?”
“Are you sure?”
I thought about it for a moment before saying. “OK, but you are to decide on the challenges for the first two Sundays of December. The rules are the same as last year. If you fail a challenge you get punished with 6 hard strokes of the cane bundle the next work day morning. If you have to miss a day, then the task (and the stroke count) is doubled for each day until you can perform it. Finally, I am in charge of what you wear for the month except the 2 Sundays you set the challenge.”
Diane was surprised, after showering, to find a full set of clothing out with a small butt plug.
She dressed and as we made our way into the office she asked “How long is the plug in?”
“All day except when you need to go to the loo.”
“That is easy, as it is so small.”
I smiled saying “well, this is probably the easiest of all the challenges you face this month.”
When I picked her up from the office she asked “How did you get that plug to vibrate occasionally, especially when I was least expecting it?”
“Easy, Alex had the remote.”
Waiting for her on the bed was a pair of very tight fitting jeans, a T shirt and a waist chain with a small padlock. This was in keeping with the regular “Dress Down” Fridays at her office.
She asked “What happens if I need to go to the loo?”
“Simple, just find me and I will unlock your padlock. But the challenge is if you need to be unlocked more than once before we leave the office, for each unlocking, you get 6 strokes with that nice cane bundle on Monday morning.”
She put on her jeans and realised that they were her tightest ones and the seam at the crotch was tight against her pussy.
The jeans did what I hoped because when we got home that night she was as horny as I had ever seen her after a day at work.
She showered and found nothing in the way of clothing for her. She did not find this unusual as she was often naked whilst at home. Over breakfast she asked what her challenge for the day was.
“Simple. Except when we are at the pub tonight, you will be as you are. When we go shopping later you will be wearing a coat that you belt up yourself without using any buttons. You are not allowed to adjust the belt once done up. If you have to redo the belt it is 6 strokes each time you have to adjust it. If you ask me for permission to button it up, it is an extra 12 strokes on Monday, followed by five days in the punishment bra and panties. If that gets in the way of any challenges, then penalty for delaying a challenge applies.”
The day went well. Over a coffee, whilst out shopping, Diane said “This is fun, I am quite nicely horny thinking how many of those passing realise that all I am wearing is just the coat.”
She actually managed the 3 hour shopping trip without having to adjust the belt or ask for a button to be done up.
When we got home she quickly removed it, dropped to her knees and started to give me attention with her mouth. I was soon hard and bent her over the handy chair and we both enjoyed our coupling.
I was both excited and nervous about what she had planned for us.
I got out of the shower to just find my cuffs on the bed. I quickly put them on and went to the kitchen. She had me sit on a chair, locked them together behind my back so I was effectively locked on to the chair. As she put a bowl of cereal in front of me she said “Today you are not going to be able to do much for yourself. I will be teasing you all day and you are not allowed to cum at all until bedtime.”
The first thing was she had to feed me my breakfast. When she was ready she released me from the chair and led me into the living room, sat me down on one of the chairs with my arms still behind my back she sat on my lap, offered up one of her nipples requiring me to suck and play with it. She kept me working her over using just my mouth until she had 3 orgasms. I was so stiff, that she even rode me to a fourth orgasm for her.
Thankfully she stopped her teasing until the afternoon, when she repeated the process. This happened again in the evening.
As we went to bed, she said with a smirk “Well I have certainly enjoyed my day, and I am so tired, you will just have to wait until tomorrow for your release.
In the morning Diane found her office clothing laid out on the bed with a short note saying “tonight you will have to face the challenge.”
After our evening meal I said “time for your challenge.”
We went to the playroom. Waiting for her there was one her most hated predicaments as she knew she would end up with sore pussy and nipples. She stood patiently whilst she was standing on two blocks of wood with her feet spread apart by a two foot spreader bar. I positioned the chain tightly so her pussy was split by it without it digging in. I then added the strings to her nipple rings so they had no slack.
I removed the blocks of wood so she had to stand on tiptoe to avoid the pull on her nipples and crushing her pussy.
I said “You have to stay there for 45 minutes. If you succeed without calling out your safe word, then I will make sure you are well satisfied tonight. Failure means you will be teased to distraction until you manage to get to sleep.”
I am pleased to say she managed to complete her ordeal, and she was a very satisfied woman who slept with her sexy well satisfied smile.
On the bed waiting for her was her usual set of clothes, her ben wa balls and the pussy lock. She inserted the balls, locked up her pussy with the padlock and then dressed.
She admitted to me that night that she had been kept highly aroused all day as she was on her feet most of the time and every movement gave her a pleasant tingling sensation.