This week’s story (and a few more to come) is inspired by a comment from Rebel last week and Ana’s advent calendar which can be found here.
Following our holiday, Diane and I had a very busy few weeks with very little time to play. Our weekends seemed to be so full that we did not have our usual monthly game. As the end of November approached, we actually had a full day on our own at home. When we cleared up after breakfast Diane said “as we have not had a game recently, why don’t we have some fun in December?”
“What have you got in mind?”
“We play one game of chess. The winner then sets up an advent calendar. Each day there will be a task to be performed. The tasks set must be accomplishable by the loser. Failure to complete a task results in a week in their chastity belt or device. The weeks in chastity will run consecutively, so the worst possible outcome will be 24 weeks of chastity.”
“Sounds interesting, but I have a few reservations.”
After much discussion we agreed that the loser of could have 4 “appeals”. The setter of the task is then required to perform it. If the person fails the task, then they are required to spend a week in chastity and the person who appealed is given one week less in chastity if they earn any. We agreed that the appeals could only be used where the task is not gender specific, for example wearing ben wa balls is classed as gender specific.Further we agreed that a maximum of 3 tasks per week could be gender specific.
We decided that we both needed a little play, so we added a further dimension to the game of chess. The first person to lose a piece would be gagged and we would each have a sore ass, the number of strokes and implements used depending on the pieces taken or being in check, with six strokes for each piece taken. Each time a person went into check the strokes were to be with the hand, a pawn with a flogger at full force, a knight would result in the paddle, a bishop would be the quirt, a rook (castle) the loopy johnny and the queen results in the cane. The overall loser would also get six strokes of the nasty 4 piece cane at what would be classed as a medium severity cane stroke. Finally if there was a draw, then we would resort to a simple toss of a coin to determine the winner of the game.
I was a little nervous about chess as I am not as good a player as Diane, although I have improved over the years.
We set up the chess board and I was lucky to win the toss and start the game. It took a few moves with Diane teasing me before I was able to take one of Diane’s pawns. As agreed, I quickly secured the penis gag we had as it is the most effective. The absence of teasing meant that I was able to concentrate better on the game. As the game progressed, it was clear that she was finding the gag a disruption to her thought processes and I started to take pieces on a regular basis, whilst she took far fewer.
It was about an hour into the game that I was able to put her into check for the first time. It did not take long before she was regularly being put in check and realised that it would only take a few moves before it would be check mate so she resigned.
The final tally was that I would get 18 hand spanks, 30 with a flogger, 6 with the paddle, 6 with the quirt and 6 with the loopy johnny.
I quickly leant over the arm of the sofa while Diane collected the implements. She gave me a nice tender warm up before she used her hand in earnest making me squirm at the end of the hand spanking. She stood back and let rip with the flogger which soon had me squealing as each stroke landed. The paddle was very intense and each stroke had me gasping as she let rip at full force. She picked up the quirt which is her favourite implement and her accuracy was such that each strike elicited a squeal as each landed on the most sensitive area of my sweet spot. The final implement was targeted at my ass and I was soon moaning as catching my breath as each strike of the loopy johnny landed.
When she had finished, I carefully stood up, felt the heat of my ass and was surprised not to feel any nasty welts.
I spent a few minutes getting my breathing under control before I said “Your turn now.” She leant over the table, grabbed the other end as I started to gently spank her ass, as the warm up progressed I increased the intensity. I told her “now for the main event.”
I landed 36 hard strokes alternating between each cheek and by the time I had finished her bum was a bright red. I picked up the flogger and landed another 30 strokes on her ass intensifying the colour of her cheeks. The paddle’s 12 strokes served to intensify the redness. I am not as accurate with the quirt as she is so I let each of the strikes land on her ass leaving 12 angry red welts. The loopy johnny followed and there were 6 clear marks from that too. I picked up the cane and quickly landed the six strokes on her sit spot eliciting gasps from her.
The final implement I knew would be the severest test, so I let her breathing get back to normal before I landed the first two strokes bringing a squeal of pain as she processed each strike. I had no wish to intensify the pain, but she mumbled something and I checked with her to make sure I understood. She wanted to have two full strength strokes instead of four medium ones. I debated with myself about this, but as she asked for it, I let rip with two heavy strikes that had her gasping and squealing. The last two strokes brought tears to her eyes and as I held her in a hug and removed the gag. She continued with the tears for nearly five minutes before she kissed me hard and said I am so randy; take me hard on the table.
Who was I to deny that request as I found her to be so wet between her lips that I was able to easily slide into her pussy. I started gently as she squeezed her muscles tight around me as I started to move in and out. She urged me on and her dirty talk soon had me ready to come. I managed to hold off until we both orgasmed together with squirting all over my groin. She lay there twitching for a while as I recovered before helping her to the sofa where I could hold her whilst she came back to her senses.
The following week I spent a lot of time working out the tasks for Diane to perform.
When we woke Diane had her usual morning shower. As she returned to the bedroom I handed her the task for the day. She raised an eyebrow as she read the task “You will spend the whole day in your birthday suit. If you have to go outside you may wear a pair of shoes that must be removed as soon as you get back inside.”
I love watching Diane being naked, and as it was her turn to cook, I knew this would be an interesting day for her.
I enjoyed the sight all day long and when we went to bed, I complimented her on how sexy she was and we were soon making love bringing the day to a suitable climax.
The task read “You will wear just one item of clothing and a pair of shoes all day at work.”
She looked at me, glared and then said “umm, this will be interesting as I have a management meeting to attend today.”
I laughed before saying “I did not know about that.”
“Don’t worry, I just thought, maybe all I should wear is a Teddy.” She replied with a grin.
She went to the wardrobe and selected a sensible jersey dress that had a built in support for her gorgeous breasts. The only thing is that it also rubbed her nipples so that they could easily become prominent. As she put it on she winked at me and said “I will be careful not to get too aroused.”
When she got back from work, she told me all about her day. “As the meeting was in the afternoon, I kept looking in the mirror and saw how much my nipples were poking out and nearly went and bought a bra.”
She then started to take it off saying, “but as you can see I did not.”
As I handed her the card for the day, this was the one that I thought that she would baulk at. It read “wait and see, ask me for the other one when you get home.”
As she came in the door, she immediately asked for her task for the day. I handed her a card that said “Your clothes for the evening are on the bed. We are going out for a meal. If anyone asks about the clothes, you must answer any questions truthfully”
She rushed up to the bedroom to find a light dress and a peephole bra and knickers made from rubber. She quickly got out of her clothes, put on the bra, knickers and dress. The black from the rubber was clearly visible though the dress and she questioned me about it.
I replied, “The black is noticeable, but it is not clearly evident that it is made of rubber.”
As we sat down in the pub, John and Kathy arrived as I had planned without Diane knowing.
After some small talk, Kathy blurted out “Is that a rubber bra?”
Diane blushed before saying “yes.” Whilst glaring daggers at me.
Kathy laughed, “How daring, I had never felt I could do that.”
Diane calmly replied, “Well it is either that or a week in chastity. And there are another 21 challenges to go. Failure on any means a week in my belt.”
John raised an eyebrow “Tell us more.”
Diane then told them all about the game and that she was the loser.
Kathy then said “John, why didn’t you think of that. From tomorrow, I will give you a task on even days and you can give me a task on odd days until Christmas.”
John looked a little put out, but with good grace said “of course dear.” He then asked “what are you doing over Christmas?”
Diane replied with a smile “not sure yet, but I will probably want to get my own back on him by then.”
I laughed “I doubt it, you will probably find by Christmas you will be very horny. Why don’t we just wait and see.”
Come back next week for more of the advent calendar.