Diane’s Challenges

My punishment for Diane’s naughty subterfuge started on Monday, with a challenge a day for a whole week.

As we got up I asked “How’s your bum, pussy and tits?”

“My bum is very sore, my pussy is ok and my tits a little sore, but I will cope.”

“Good, this week you get a challenge a day, each one you complete successfully gives you a week less in your belt; however each failure adds an extra week of confinement, so you have plenty of motivation to succeed. If you manage the first four, then you do not have to complete the other three.”

“Sounds good to me.”

“Just to add to the fun, I will be selecting your clothing for the whole week and I will make sure that it is suitable for you to wear in the office. Now go and shower, whilst I get your wardrobe ready for today.”

She did as asked and I laid out a very simple jersey style dress, suspender belt and stockings and a pair of 4 inch high heeled shoes. I added 2 envelopes. When she had showered I told her to put on the clothes laid out, and wait without opening the envelopes.

I showered and when I got back to the bedroom I asked her to select one of the envelopes. I smiled as I saw what she had selected. I grinned as I said “The other one is your challenge for Friday. For today you need find me about 15 minutes before your afternoon meeting with Dee starts.”

In the office, at 1.45 Diane promptly arrived at the area I was working in. I looked up at her smiled. I handed her a little bag and said “your challenge is to put these on with the laces so on one side it at the front and the other at the back. When you have done that, tie the lace at the back to the other side leaving a little slack and the same at the front. They stay on until we get home.”

I watched her look into the bag, go a little red faced. I reminded her, if you don’t do it is an extra week in the belt, or maybe a week less if you do.”infernal_2_cilice01_final

She smiled as she replied “Well I am not going to fail on the first challenge.”

She came back a few minutes later handed me the bag and discreetly showed me that she had followed instructions and was wearing the 2 Cilices that were also acting like a mini thigh hobble.

We went to Dee’s office with Diane walking almost normally, wincing slightly as she dug the spikes into herself by taking too long a stride.

Dee welcomed us both into her office and before we started our business she noticed Diane sit down carefully and asked about our weekend. Diane told her and Dee smiled saying “Sore bum and tits as a penalty for some orgasms, sounds fun.”

“Not my kind of fun as it was that evil cane bundle at a hard setting. I was really screaming at the end.”

“Oh well, that is all over now.”

“Not quite, I have a chance of getting out of belt time completely and my first challenge is in place.”

“Playing in the office again? My my you are naughty.”

Zack entered as she said that last comment, and asked “Playing at the office again? What are you 2 up to?”

Diane told him, and he smiled as he said to Dee, “I like the idea of discrete play and punishment. Next time you swear I will have you wear the cilices all day from when you get up until bedtime, locked together. Now that will be fun to watch.”

I smiled at Diane with a little cock of an eyebrow and I could see that she got the message.

The meeting went well and Dee was far more restrained than usual. The biggest issue was relating to some issues from one of the major suppliers. Dee swore as she heard this before she said “We better F***ing look for an alternative urgently.”

Diane calmly replied, “It is all in hand.”

Zack smiled at me asking “can I borrow your cilices for Friday?”

I replied “of course.”

Dee said nothing, but the frown on her face said it all.

Diane successfully kept the cilices on until we got home, although when she crossed her legs once, she quickly moved them back.


Tuesday morning came around and Diane did not find any clothing waiting for her after her morning shower. I told her “Your challenge for the day is for you to be totally naked until you get to the office car park. Then after work you will strip off in the car park and come home naked, staying like that until bedtime.”

She wiggled her bum a little saying, “At least I can be warm in my car.”

I reminded her that “your car is being serviced today, so I will be driving the Stag today, and it is a nice sunny morning.”

She shuddered on hearing this saying “I’m going to complete your challenges so I can be free of belt time.”

We went out to the car, I lowered the top and Diane sat in the imagespassenger seat, knowing my views on her slouching down, sat up properly, put her seat belt on as I lowered the top.

The only time that she might be showing off her glorious assets to the general public was if we got stuck in traffic.

The drive to the office was uneventful and in the car park I handed her the clothing I had selected which was, of course, totally in keeping with her being a high ranking member of staff.

That evening, after work she got to the car and realised that I had parked close to one of the bright lights. There were quite a few people around so she discreetly removed her skirt, tights, knickers and was shielded by the door before getting in the car to remove her blouse and bra.

The drive home was in the dark and she was less likely to be noticed, especially when we got held up by traffic.

When we got home, we both had some work to do so we decided to have a meal delivered by one of the local take away. She placed the order and was told it would be about 45 minutes. When the doorbell rang about half an hour later, I was just finishing up so I had her answer it saying “No hiding behind the door.”

She was a little embarrassed by this, but rose to the challenge beautifully and without embarrassment collected our food off the slightly startled delivery woman. I heard the woman apologise “I am sorry, I know I’m a little early, but your order was ready and it is on my way home, I hope I haven’t disturbed you.”

“No problem, I am often like this around the house.”

Wicked Wednesday

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2 Responses to Diane’s Challenges

  1. Oh my, cilices… those terrify and intrigue me at the same time…

    Rebel xox

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