For Diane’s seventh day of her advent calendar I said “You can select your own clothing and torment for the day. If I do not think it is challenging enough, you will get 12 strokes of the cane tomorrow morning after your shower.”
She thought for a moment before she picked up our most stringent nipple stretchers and put them on under her blouse, without a bra, and hidden from prying eyes by the jacket over it.
She wore them all day and before we went to bed I said, “time for a treat, I took her to the playroom and with the neoprene flogger, that sounds far worse than it actually feels, had her screaming with orgasms. I lost count of the number of times she came before I let her down and took her to bed where she slept very soundly.
After her shower, Diane returned to the bedroom to find a shank of rope on top of her clothing for the day. She asked “what is the rope for?”
With a smile I answered “A nice rope corset and knickers for you to wear all day.”
It took me about 20 minutes to fashion the rope bra and corset that was tight, but not overly tight. From the back, at the bottom of the corset was a crotch rope with a crupper that I tied to a loop at the front. As I finished I said “You can undo the crotch rope when you need to go to the loo during the day. I will be checking at times to ensure that the crotch rope is nice and snug, so be careful to tie it up tight when you have been to the loo.”
When I checked in on her in the late afternoon I commented “You have tied it even tighter than I did.”
“I know, but it is so sexy like this.”
On the way home she was fidgeting in the car and it was clear that she was rubbing her legs together to increase the stimulation to her pussy. Finally as we neared home, she used her hands to bring herself to a climax that could easily have distracted me as I was driving along.
Friday being dress down day allowed me to make her day very interesting. I laid out for her the pussy padlock, a very tiny bikini (often called a microkini), a dress with a fairly short pencil style skirt and a pair of shoes with 5 inch heels.
Diane, before she put on the pussy lock went to the toy box in the bedroom, got out a slim dildo stuffed it inside her pussy before locking her lips together. She then put on the rest of the clothes. When she had finished I said “The challenge today is simple, I will be locking the zip of your dress to your collar* so it cannot be removed until we get home.”
Within an hour, she was pleading with me to let her remove the bikini top saying “my nipples are itching like mad.”
I laughed “So you like the itching powder that I rubbed in to your bikini top?”
As soon as we got to her office Dee asked her to join her and Zack for a few minutes. Dee saw Diane was a little uncomfortable in her gait and asked “What’s up?”
“Charles has got me wearing a tiny bikini with itching powder on the inside of the top.”
Zack laughed “Wow, playing at the office again. I know it doesn’t affect your work, so I am not worried.” Turning to Dee he continued “I think we will have to start having you in discomfort sometimes.”
Dee said nothing in reply but said to us “I hope you have nothing arranged for next Thursday night. I have been sent invitations to the trade dinner and celebration that night. Diane and Charles, one of them is specifically in your names.”
I answered “nothing that we can’t change.”
“Good” was all Dee said.
The day passed uneventfully. Once at the car, Diane asked me to unlock her dress so she could remove the bikini. I laughed, “And if I do, you get to wear absolutely nothing for the rest of the evening, even when we go to the supermarket.”
“Ugh, I will wait until we have done the shopping.”
“It is either now or bedtime, otherwise it is a failure with a very sore bum on Monday morning.”
She reflected on this for a moment before saying “No way do I want that evil cane bundle on my bum on Monday.”
Saturday she rose to find she had no clothing, just her cuffs and a belt which locked on. I said “Once they are on, you are going to have the chains run through the D ring on the belt connecting your left wrist to your right ankle and vice versa. There will be a little slack, but if you need to reach up you will have to raise a leg. You are not allowed to ask me to help with any chores around the house unless it would be dangerous for you to do so. Any requests for help must be preceded by ‘Master please help’. If I think the request is spurious or unnecessary it will incur a lash on each tit from the quirt. Be warned they will show when we meet up with James and Petra tonight, so be very careful.”
Diane was very subdued all day and managed to do all the housework and her chores without asking me for help once.
This being Sunday morning, Diane was the one who decided what was going to happen.
I found the most severe cock cage waiting for me on the bed. I was still limp so it was relatively easy to put on. Once it was locked on I went to get breakfast ready only to find her there naked. She smiled at me saying “I am glad you are now ready.” She gave me a long seductive kiss that started to get me aroused. I started to grimace as I got hard. She broke away from me. “Just as I hoped.”
Diane disappeared, to get dressed, before returning with a sweater and trousers for me. This was so we could get most of our Christmas shopping done, including a new dress for Diane to wear at the upcoming dinner and office parties.
The shopping for the dress was made more fun as Diane insisted I help her in the changing room. She stripped removing the 2 pieces of clothing that she wore, groped me and twisted my ball sack that had me grimacing again.
Once the shopping was complete and we were home she stripped off again and started to tease me wickedly. It was very uncomfortable in the cage. She just continued all the day and evening. Finally at bedtime she released me from the prison and I was able to satisfy my lust and exploded inside her.
Monday morning meant I was back in charge so I left out her tack bra for her to wear under the dress I had selected.
The last thing on the agenda for her day of work was the regular Monday meeting with Dee. They both sat down and Dee asked “What is your calendar game today?”
“The tack bra. It is beginning to get a bit uncomfortable now as I have had it on all day.”
“Zack bought one yesterday for me to wear today. It is getting rather annoying, but it is better than the consequences of a severe caning before coming into work.”
* Her collar is a discreet necklace that she wears every day.