Predicaments- part 1 of many

Part of what follows is based on real life experience play session. The rest is fiction. You will have to decide what is was real and what is fiction.


We are a married couple in our 40s. I am tall (192 cm) and fairly slim with an average build whilst my wife, Diane, is much shorter (160cm) and slightly overweight. We both have stressful jobs and work hard to make ends meet. We enjoy experimenting and she is usually the top in our relationship, but we switch when the urge takes us. We make time to play on the last weekend of every month. If we have to be away, we postpone the play until the following weekend.

We both have our own chastity devices that are worn when we are apart for more than a week. Hers is a chastity belt that is so snug that she cannot touch her pussy or clit. Mine is a CB3000 and an additional ring with the teeth can be fitted instead of the normal one that makes it painful even to be aroused.

Diane is multi-orgasmic and comes easily once she has been warmed up and when she is really turned on squirts so much that we have to change the bedding. She has pierced nipples in which she wears heavy stirrups constantly. I have also conditioned her so that when we are holding hands, with the use of my thumb I can turn her on. Often when out with friends a gentle stroke of her wrist and she is squirming in her seat, she will whisper in my ear “do you know what you are doing to me?” To which my answer is often “yes!” enjoying the moment. If she is in a dominant mood, I know that if I continue, there will be payback which can be classed as “funishment”, that is a punishment with pleasurable release at the end.

She usually decides whether she is going to be the bottom, however when we both want to be the top, we have devised a way of seeing who will be the top for the playtime. This involves getting a pack of playing cards, shuffling them well and cutting to see who goes first. We then take turns picking up a card, and whoever draws the first 7 is the top for the session. If she loses, she is not allowed to punish me at a later date for it.

Chapter 1 Friday evening

Diane got home from work as usual about 7.00 pm after a particularly hard week. I had been home for an hour before she arrived and her evening meal was ready and waiting. She turned round to me during the meal with the smile I knew only too well. The smile was suggestive and inviting. She commented over the meal that she wanted to play. I turned to her, held her hands and said I had an idea that she may enjoy, but she needed to allow me to be her top for the session.

She said “NO!”

She also had ideas for the night involving her as a top so she asked me to get the cards. We both shuffled and cut to decide who went first. I won, reshuffled the cards and took the first card off the deck. It was a 7, deciding her fate, she was the sub.

She groaned in acceptance. I then gave her the rules for the scene that I had already prepared.

The Challenge

For the period of time that you select you are not allowed to cum irrespective of how much I tease you with my hands or other parts of my body (including kisses and licking). However to make it fair I will not use my mouth on your pussy or clit. I will be attempting to turn you on and make you cum and you have to dip into all your resources to hold back.

The time you select is determined by the face value of a playing card you chose and gave to me (I will keep it in a sealed envelope that you will sign over the flaps so you know that I have not cheated, if we do not finish tonight).

An Ace is 30 minutes

2 to 6 is one hour

Seven to 10, jack or queen is 2 hours

King is 2 hours 30 minutes

You will not know how long you have to hold out for, however you know that the maximum initial time is 150 minutes. When you have completed the challenge, you will be told that “you may cum”.

In addition, there are added time penalties for breaking any of the rules. The suit of the card determines how many penalties are allowed before additional time come into play. A penalty adds 10 minutes to the original time.

Hearts – no penalties
Clubs- 1 penalty
Diamonds- 2 penalties
Spades- 3 penalties.

A penalty is earned by:-

  • any attempt to stroke your pussy or clit
  • any request for me to stop what I am doing
  • any request for me to change what I am doing
  • any wriggling or attempt to prevent me using my hands or any toy
  • any derogatory comment such as using the words “evil” or “bastard”, with me deciding what is considered deserving of an infraction. (I will be fair and warn you once about any other word, then if you repeat it,  it becomes an infraction).

If you cum, this is classed as three penalties adding 30 minutes to the time, and there is no allowance from the suit of the card.

You will be told when there is a penalty and time is being added.

Additional penalty– If you attempt to stroke your pussy or clit at any time after your “free penalties” have been used up, your wrists will be cuffed behind your back with a length of chain at most 18 inches long until the time you leave for work on Monday morning.

For the period of time you selected, I will tease you with my hands, my mouth (but not around your pussy or clit) and some toys, but you are not allowed to cum until the time selected plus any accumulated penalties has elapsed. If you cum we will take a short break and the timer will start all over again and any penalties already incurred will still stand.

Example:- you have to hold out for 90 minutes and have incurred 6 penalties, this means you cannot cum for 150 minutes. If you cum after 140 minutes, you then have to survive the 150 minutes plus a further 30 minutes (plus any extra penalties earned)!!

If you want a time out for the use of the toilet, you will use the words “Amber Time Out”, however you will leave the toilet door open and the time out will last a maximum of 5 minutes. We will restart the challenge as if you have come, but this will not count as a penalty. However you may only use the time out facility twice during the whole of the challenge.

Toys that I may use

Small vibrator
Pin Wheel
Small bungee flogger (3 inch strands)
Ice cubes (up to 6 per session)
Candle wax
Massage oil
Nipple weights

The challenge is completed if you can last out the time allotted without cumming. I am then the loser.

However, the challenge is lost if your total time to hold out reaches 480 minutes (8 hours) or you use your safeword. You will not be put in bondage (other than wrist cuffs described above) during the challenge and therefore the safeword should not be needed.

The loser will spend 1 month in their chastity device.

She looked at me and asked if I was being serious to which I replied “Yes”. She glared at me and told me what a devious horrible man I was and then declared that she would not cum until I told her she could, even if it was three or four hours of continual teasing. I replied that I will be teasing her as much as I can and will be trying to make her cum. She replied “no way will I cum”.

I laughed at her and said that she would cum and that she would not last for the time period until at least Saturday night. She replied emphatically that she would succeed. She then suggested a side bet and that the start of the scene was delayed until the Saturday morning. I asked why to which she said we needed to negotiate, agree and write up the “fate” of the loser as the suggested penalty was not enough. I said if we were to wait until the morning, then she should start wearing the chastity belt and ben wa balls and I agreed to her suggestion that I was locked into the CB3000 until the end of the challenge.

When she fetched the belt, I inserted the ben wa balls and fitted it. She locked my device on, using the spikes for additional discomfort. For three hours we negotiated, and the agreement we came to was that the loser would be locked in chastity for 3 months, without being allowed to cum. The loser would give relief to the winner using their mouth and hands a minimum three times each week. The loser would also be given 6 hard strokes of the cane (sufficient to  raise welts) on each Monday morning before leaving for work to remind them of their failure in the challenge. To determine the loser, if she failed to complete the challenge as explained in the rules or by 10pm on Sunday she would lose, however if she succeeded in the challenge, I would end up the loser.

Diane then suggested a slight twist in that if during the challenge she used her safeword, I could fuck her immediately, the penalty for losing would be doubled to 6 months and 12 strokes of the cane each week, with me being allowed to remove the belt once a week for up to an hour, at the time of my choosing, I could fuck her and then relock her in the belt. We agreed that she would be allowed to cum as often as she could in that hour.

We typed up the agreement and both signed it. We also agreed that she would get a minimum 20 minutes rest and wind down time every time she orgasmed whilst doing the challenge.

By this time it was well past our usual time when we went to bed, both locked up.

To be continued……..

This entry was posted in Uncategorized and tagged , , . Bookmark the permalink.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out / Change )

Twitter picture

You are commenting using your Twitter account. Log Out / Change )

Facebook photo

You are commenting using your Facebook account. Log Out / Change )

Google+ photo

You are commenting using your Google+ account. Log Out / Change )

Connecting to %s