My long weekend starts

The couple of weeks following Dee’s stay with us were very busy and it was not until the bank holiday weekend that Diane and I had a chance to be on our own for a long weekend.

It had been quite a while since I had taken the role of submissive for more than the odd couple of hours of playtime, so I had agreed that she would take the dominant role for the whole weekend.

On the Friday evening, as requested, I had put on my chastity device when I got home. When she got home, Diane disappeared into the bedroom to change out of her work clothes.

She came into the office area wearing a very sheer blouse that immediately caused me discomfort from the cage. She gave me a bit of paper with the rules for the weekend, which was to start at 8pm as we had agreed.

As I started to read the instructions Diane had an evil grin on her face that I knew would mean a very challenging weekend ahead.

The paper read-

  • Following Dee’s weekend here, I have decided to adapt it for my pleasure.
  • Starting at 8 tonight until midnight tonight and between 8 am until midnight on Saturday, Sunday and Monday, You must make me cum once every hour.
  • To make it more interesting there is a window of five minutes either side of the hour in which you can fufil this task. Any orgasms outside this window do not count toward your task. So if you bring me to orgasm during the five minutes before 9 and another in the five minutes after 9 then you have completed the task for the hours between 8 & 9 and 9 & 10pm.
  • You are allowed to use toys to help you, however you may only use each of them for one orgasm each day.
  • You may use hands or your talented mouth for two consecutive orgasms, but the next two will have to be with a toy.
  • Each orgasm that you give me will give you one merit point.
  • If I judge that you have been very creative in the way that you give me an orgasm, I may at my discretion award an extra merit point.
  • However any failure in bringing me to orgasm for each hour will lose you ten merit points every orgasm missed.
  • Any hesitation on doing anything you are asked will result in the loss of a merit point.
  • Also you will be given two additional tasks on each of the three full days.
  • Completing a task earns 5 merit points.
  • Failure to complete a task means you lose 5 merit points.
  • Any negative balance will be carried forward to the next day. A negative balance at the end of any day will earn you :-
    1. one day in your device and
    2. 6 hard strokes of an implement of my choice

    for each negative merit point to be administered on Tuesday morning at breakfast.

  • To encourage you to complete the challenge, if you end the weekend with a credit balance, then I will suffer the same penalties for each credit point.

When I had finished reading the instructions, I was asked “Any questions?”

“No, it seems to be all fairly straightforward.”

“Good, I am looking forward to loads of orgasms this weekend.”

I gathered together a wide selection of toys to help me in completing my task for the weekend.

As we sat cuddling on the sofa I noticed that it was approaching 8 so I started to stroke and caress Diane, slowly removing her top so I could have access to her breasts. I started to play with her nipples as I knew that it was a great turn on for her. The tips got harder as her level of arousal increased. Her moans and sighs of pleasure increased too as I worked hard to be able to give her the first orgasm in the five minute window I was allowed.

I unbuttoned her jeans and as I reached with my fingers for her crotch I was immediately presented with a major challenge because she was wearing her chastity belt.

I looked in amazement and asked “where is the key?”

“Somewhere well hidden, and you will have to find it.” Was all the reply she gave me.

I picked up one of the vibrators I had already gathered together to aid me in my task. I used it to tease her nipples as well as sucking pinching and pulling on them to try to bring her to the first peak of the evening.

Whilst I could smell the level of arousal increase as well as her increased moans, I was also getting aroused, and the confines of my cage made it uncomfortable as I did my best but failed to get her to orgasm.

I let out a resigned sigh as I stopped my ministrations as she teased “You didn’t think I would make it easy now?”

I got up and started looking for the key to the belt. I spent a lot of time searching for it, and I lost track of the time when she announced at 9pm, “well that was a quick 10 merit points lost.” I redoubled my efforts and was getting very frustrated that I could not find the key.

I started my work again well before the next window and using a lot of effort with my mouth and hands managed to succeed in bring her to a weak orgasm just before the hour ran out.

“Well whilst it was not that satisfying, I did come so you have earned your merit point. For that creative work, you will find the key to the belt in the bedroom.”

I quickly rushed to the bedroom, and started searching for it. She came up, leaned against the doorframe and watched in amusement as I frantically searched all the drawers and wardrobes.

It was soon approaching 11pm, when Diane said, “Go the bathroom now and when you return you can try and earn the next merit point.”

I disappeared into the bathroom, did my business and on returning, I found Diane relaxing on the bed having removed the belt. I quickly joined her and started working hard with my mouth to get her fully aroused so I could give her two quick orgasms in the window I had available. I glanced at the clock and quickly started to use my tongue to trace the alphabet on her clit and by the time I got to the letter G she came hard. I continued my oral ministrations and when I got to Y I felt her come hard for a second time, squirting her nectar all over my mouth.

I let her recover from these orgasms, and she mumbled, “that was good.” We drifted off to sleep spooned together with me taking a while to drift off until I was no longer in discomfort from the confines of my device.

After a night’s rest, I managed to complete my task at 9 so she started the day in a good frame of mind. I also managed to earn more merit points for the hours of 10, 11, 12 and 1. After we had finished lunch Diane suggested we went shopping in town. I thought to myself, “I hope this is a quick trip.”

I completed the orgasm task for 2 just before we left the house. Diane took her time in the shops and when we were in one of the big chain stores she said “Here is your first extra task for today. You are to go to the lingerie department and buy me three new bras in different colours. They must be of different designs and I must not already have one of the designs at home. You have half an hour to meet me in Starbucks across the road.”

Well the easy part was that I knew her bra size. The hard part was finding three designs that she did not already have. Eventually I made my selection and just made it to Starbucks within the time allowed.

As I sat down she passed me a coffee and then asked to see what I had bought for her. I passed her the shopping bag and she picked out the first one that was a very sheer flesh coloured bra. She looked at it carefully and said, “It is a bit see through, but I like it.”

The second one she picked out was a sexy black one with a pretty lace design on the cups. The third was a white one that did not have shoulder straps.

“Umm, well that task has been completed, not what I would have bought, but I like them all.”

We finished our coffee and she said “now for your second task. Go back to the store and buy matching knickers for the bras. I will wait here for you.”

“No need.” I replied, passing over a second shopping bag. “I thought you would like to have the matching knickers, so I got them at the same time.”

“Good forward thinking. I think that has earned you a bonus merit point.”

Just as we left the coffee shop, Diane said “I think you forgot something.”

I looked at my watch, gulped and she continued “You’ve earned 11 points but lost 10 for your oversight.”

I apologised and said, “with respect I did not see how I could have given you the attention you needed.”

She replied “Well you could have asked for these.” handing over the remotes for the bullet vibrator and the butterfly clit stimulator.

“Since we left the house they have been on low and the sensations are glorious.”

I took the remotes from her and she graciously agreed to continue wearing them until after 5pm.

At the right time I turned the bullet off and let the clit stimulator bring her to orgasm. I turned off the clit stimulator and then turned the bullet to full and with a little help from my fingers managed to get her to climax twice more just inside the window of time available. For the rest of the evening I managed to complete my duties ensuring she had at least one orgasm for each full hour.

Wicked Wednesday... a place to be wickedly sexy or sexily wicked



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