The Sunday morning following our weekend with the others I turned to Diane and said “Go and get the Games jar.”
I was a little worried as many of the games we had played so far resulted in Diane being the sub. We both knew that most of the games left would be those where she was most likely to win.
She opened the jar and picked out the piece of folded paper. She opened it to reveal “Tit Game”.
I shuddered as this game is the one that I am probably the worst at. We had played it a number of times before and I had only ever won once. Furthermore, in recent months her ass had been receiving a lot of attention and mine had hardly been touched by any implements.
This game involves a little trip to the local shopping centre. Whilst this would allow us to get what we needed for the upcoming holiday, the twist was that one unsuspecting person would be the subject who decided the result of the game.
We enjoyed our shopping trip and had finished most of our purchases when Diane whispered in my ear “are you OK with the brunette the other side of that display stand?” Neither of us could make out her full body shape and I suggested 34B while she chose 38C. We walked around the other side of the display and Diane started looking for the new bikini she needed. Meanwhile the unsuspecting woman made her final choice and we could both see the colour code for a C cup and the bust size was clearly visible as 36.
I knew I was in for a sore ass as the rules of the game were:-
- Whoever got the closest cup size was the winner
- If there was no clear winner, then the bust measurement would count.
- If neither were right, the closest to the right size was the winner.
The penalties were:-
- The cup size determined the number of times the loser would have a sore bum. An A cup would only mean one session while a B cup, 2 and so on.
- The number of strokes is the measurements guessed added together
The final part of the game is that the loser is blindfolded and has to bring the winner to a climax that must be in progress as the time ends. The timer is a clock that times down and is not visible by either of us. Failure results in a number of days in the chastity device determined by added the totals of two rolls of a pair of dice.
When we finally got home, Diane gleefully said, “Nice for me, not so for your ass. I make that 72 strokes of implements of my choice three times until we next play a game. Also you have the extra challenge.”
As we relaxed Diane ordered me into the bedroom and she proceeded to tease me by slowly stripping off. This made me instantly hard. I had to set the clock for 36 minutes and when she was ready for me to start, she put the blindfold on me and said time starts now.
I soon started kissing her gently on her inner thighs that produced plenty of moans of pleasure. I started on her pussy lips, teasing them open with my tongue that produced even more gasps. She was soon writhing in pleasure and as soon as I teased her clit out from behind its hood, she came for the first time. I continued to pleasure her and soon had her pleading for me to finish her off to her second climax. I had lost all sense of time and continued to work my tongue on her pussy and just as she was approaching her third climax, the clock indicated that time was up. She instructed me to carry on and as I played my tongue around her clit she screamed out “YYYYEEEEESSSSSS” and came hard allowing me to taste her nectar as she squirted all over my face as she came.
After we had relaxed after the session, she said, “Go get the dice”. I rolled them twice and managed to have a relatively low total of twelve which was a bit of a relief.
She grinned “I have an idea.” She got up and went to the computer. She managed to contact Corrine on Skype, and then said to Corrine “Can we go to messaging for a few minutes?”
“Of course.” replied Corrine.
A few minutes later she came called me into the office and with a bright grin on her face saying “You have a choice, A or B.”
I chose “B.”
Corrine laughed, “Great, just as I hoped.”
This made me feel nervous. We soon completed the call.
Over dinner, Diane said, “your choice has given you a temporary respite from chastity until I get something sent to me. You will get a sore ass tonight as the first of the three you are due and be prepared to find sitting difficult on the next two Mondays, so that when we go on Holiday there should be no visible marks left.”
We cleared up after our meal and I was ordered into the sitting room, and bent over the back of a chair and Diane proceeded to restrain me so that I would not be allowed to avoid the impending assault on my ass.
Diane gave me a very pleasant warm up starting with her hand and then a flogger. When she felt I was ready, she blindfolded me, left me for a few minutes before returning to my side saying. “These 72 strokes are going to be felt, and just to make it more interesting, you will have to count backwards saying how many are left. If you miscount we will start from the beginning again.”
I gulped and replied “Yes Diane.”
I felt her hand stroking my upturned ass and then the first splat type sound was heard as the paddle landed hard on my ass. I quickly announced 72. I managed to keep the count going correctly until a stroke landed which was the hardest so far with the paddle. I managed to say “51.”
“Oh how nice, it should have been 52, so here we start again.”
I managed to get to 48 without making any errors, and she said “now to make it more interesting.”
She soothingly stroked my ass, rubbing a little of the burn away until I felt the first hard strike of a wooden spoon. I squealed and managed to keep count properly as every stroke landed. As I had called out 25, she started to stroke my by now well tenderised ass and this indicated to me that there was likely to be a change of implement.
I felt her hand leave my ass and a swish accompanied by a crack was heard as the cane made contact with the top of my ass.
I gasped “OWWWWWWWWWWWW, 24.”
As the strokes continued to land and the count meant I had just one stroke to receive, there was a pause until she said “You don’t have to count this one.”
I loud whoosh was followed by a sharp crack as the implement landed on my ass. I screamed out as the I felt the pain and Diane slowly walked around, removed my restraints and as I stood up I took off the blindfold and through tear filled eyes I saw her holding that dreaded vicious 4 cane bundle.
She giggled as she held me close whispering, “I hope you enjoyed that one, and I was only gentle.”
I was still struggling to recover from the stroke and I said nothing for a while. I finally managed “I hope that gets broken in the next week.”
“Oh no it won’t. If it is broken except when in use on either of our asses, I will ensure that Corrine dishes out a punishment caning to you with her one.”
We cuddled together on the sofa for a while and later as I went to get drinks, I quickly went upstairs retrieved my chastity device and took it Diane to fit on me.
She laughed, “We don’t need that for a few days. Your choice of B has both rewards and a penalty.”
On the Monday two weeks later, after my ass had been tenderised again on both Sundays, Diane said “Go get the box holding your device.”
I did as I was instructed, and she then produced to give me the most wonderful blow job. She brought me to a shattering climax and when my erection had softened, she proceeded to put the device in place, having added the horrible teeth ring that made an erection even more uncomfortable than normal.
“This is your reward for choosing B. Corrine has kindly sent this padlock and she has the keys. Once locked on, it cannot come off until we see her on Sunday. The special reward for this is only having to endure 6 days in it.