Diane slept well after her fun of the previous night. Having done her business in the bathroom, she went to put on her special knickers before I stopped her. I passed over the ben wa balls and the bullet vibrator saying “You will need these today.”
She replied “I hope I am not the only one.”
“Of course not, Dee will too. I also hope Kathy does too, but that is not compulsory for her.”
“When did you decide on this?”
“Last night as you were recovering.”
“Ugh. I suppose you have something nasty for me today as I was not in bondage last night.”
“Zack has devised something and none of us know what it is yet.”
She had a concerned look on her face and soon had installed her toys and put the knickers on just before the deadline.
We went down to breakfast and just as Zack and Dee joined us, there was a mild squeak from Diane and Kathy, and a loud one from Dee.
Zack grinned saying to Dee “well you must have been late putting on your knickers.”
“I was a few minutes early according to our bedroom clock.”
“Well what time is it now?”
She looked at the wall clock, frowned and exclaimed “What!”
“Yes, I thought it would be fun to see whether you would notice.”
Dee was not happy, but could do nothing about it.
After we had eaten, Zack said “We have some unfinished business from last night haven’t we?”
There was a chorus of “Yes” from the rest of us.
Turning to Dee he said “while you were recovering last night, we agreed that there will be a little test for you and Diane instead of being bound for the night.” He then added with a wry smile on his face “It will be fun for us to watch.”
Tom asked “does it just have to be those two?”
He then beckoned John over and they had a whispered conversation before they both nodded in agreement. Zack then said “No, anyone can join in. However things need to be slightly different for the men.”
Suzy asked “Do we know what is involved before we decide to take part?”
“No. All I will say it should be fun for everyone.”
A few minutes later everyone agreed to take part.
Zack smiled saying “great. Although I cannot take part myself, I am sure you can devise something for me later. Now I hope you all have wrist and ankle cuffs.”
Some of us had not brought cuffs and John disappeared for a few minutes before he came back in with a box. He passed out a set of ben wa balls and a bullet vibrator to the women and a butt plug to each of the men. John produced cuffs for those who had not brought any.
Zack said, “Now it is time for you to go and insert your toys and put your cuffs on. Dee, Diane and Kathy need not disappear as they already have their toys.”
We disappeared, inserted our toys and gathered back in the kitchen. He made sure that every ones cuffs were secured so our wrists were attached to our ankles and the ankles secured together with a short link.
Once we were all secured, he said “the challenge is simple. You will make your way to the boathouse secured as you are. The first person to reach the boathouse is the winner and will not face any penalty.
The severity of the penalty will depend on your placing. The loser between Dee and Diane will automatically be placed last and suffer the severest penalty of all.
Except for Dee and Diane, there are no restrictions on you ladies, however Diane may only orgasm once and Dee twice without facing the cane, also between them each extra orgasm will add 10 minutes to their time. This difference is because Diane has had much more training in resisting orgasms. The race starts when I turn the vibrators on. The vibrators will be turned off when you finish the course.”
We were allowed to make our way out of the kitchen through the back door so we could get used to moving around. We all waited for a while outside until suddenly I felt my butt plug start to vibrate and the vibrations immediately hit my prostrate so it was a serious added distraction.
Corrine glared as she felt the vibrator start to be told by Zack “Yes, they are running at the highest setting.”
I started to waddle as best as I could and found it extremely awkward making my way across the soft grass under my feet. It was not long before Suzy slipped over and struggled to get back up. Just as she regained her feet she fell over again as her first orgasm hit.
The deviousness of the race came apparent as I felt my prostrate being massaged very pleasurably and made concentration on getting to the boathouse very difficult.
As I arrived at the boathouse I felt the vibrator stop and I looked around as I recovered and noticed that Corrine had made it there first with me second. We helped each other out of our bindings and as everyone passed the finish line we helped them out of their restraints. The last person over the line was Suzy who looked had the contented look of a satisfied woman.
Dee looked a little dishevelled and Zack reported that she had orgasmed three times so she would enjoy the cane tonight. Zack then announced the order of finishing as
Although Dee had just beaten Diane, the extra orgasm she had meant that she would automatically be in last place.
Diane sheepishly admitted “I did come once during the race and again after I had finished, so there will be two sore asses at bed time.”
Dee asked “what is the penalty for coming in last?”
“You will find out after lunch.”
After lunch, Zack explained the penalty system. “For coming in second, Charles will have to spend just ten minutes in a comfortable frog tie squatted over in an upright position. The next place, Maria will spend twenty minutes in the frog tie. Each place lower adds ten minutes to the time. If you fall over during your time an extra five minutes will be added to the time spent in the frog tie. This means Dee will be spending at least 2 hours in her frog tie. There is an slight out available, in that if you decide to be released from your frog tie early, you will receive one stroke on your sit spot from a switch that you cut yourself for every five minutes that you have remaining. The stroke will be administered by your partner and will only count if there is a mark left by it. Maria and Eva, I hope that you will accept Corrine administering your strokes if necessary.”
The sky had clouded over so it was decided that we would undertake the penalty in the lounge where there was a reasonably lush carpet.
Corrine helped Zack with the frog ties. We were restrained in the reverse order to our placings, so Dee was the first and I was the last to be secured.
After 10 minutes of being in the position, I was released and able to stretch my legs which had already started to ache. Maria was next and we chatted about the deviousness of the penalties. Dee was the first to fall over as her knickers gave her a series of jolts that made her ass clench each time the pads on her butt activated. The first person to be asked to be released early was Tom, followed quickly by Kathy. After about three quarters of an hour, only Dee and Celia were still restrained. Dee managed an hour before being asked to be released and Celia finished her allotted time a few minutes later.
When everyone had stretched their legs and recovered from the ordeal Zack calmly asked Dee, Diane, Tom, Suzy, Kathy, Susan, Eva, William and Celia “Please go to the weeping willow tree and prepare a switch. The switch has to be at least three feet long.”
They all came back with their switches and Zack said William would be first and invited Celia to administer 2 strokes to his sit spot.
Celia passed the switch to Corrine saying “I am not any good at this, so please administer his strokes for me.”
Corrine replied “with pleasure.”
William bent over and when he was in position she raised the switch and quickly landed it in just the right place to make William squeal in alarm just after it landed. The second landed and produced another angry red line which produced another squeal form William.
Diane was up next. The switch she had selected was very whippy and I knew that it would be painful. I gave her the strokes in quick succession which produced whelps of agony and left four angry red lines just below her sit spot as I knew she was going to get a severe caning later.
Kathy received her five strokes from John and her eyes had welled up as if about to cry.
Eva was up next and in no time there were six angry red lines on her ass. And she was clearly feeling them. When it was Celia’s turn to face her switch, William passed it to Maria “You are going to better than me, and she is one of your subs anyway.”
Celia assumed the position and was clearly nervous. Maria landed her strokes with precision and there were 6 clear red stripes on Celia’s ass. Celia bolted upright after the sixth stroke, rubbing her ass saying “That was Ouchy.”
Maria consoled her by hugging her and whispering in her ear.
Suzy was the next to turn her ass up to receive the eight strokes she was due. She felt each one as the red lines showed up and produced yelps as they landed.
Susan passed her switch to Dee who administered the 12 strokes very quickly so Susan could not process the pain before the next stroke landed. She was clearly feeling the effects of the punishment as she stood back up. Tom was next up and Suzy landed the 13 strokes with exacting precision making Tom squeal as each one landed.
Zack passed the switch to Corrine saying “I know you have wanted to give Dee a sore bum for a long time.”
Dee nervously took up her position and Corrine delivered the first blow. It was a vicious strike that landed just at the tender spot where the thigh meets the ass. Zack commented “that was little low.”
“No, because she is going to get a severe caning tonight as I am sure she will be orgasming again tonight.”
Corrine landed the next thirteen strokes so there were 14 welts clearly visible around the top of Dee’s thighs and the lower part of her ass.
Next week the evening’s entertainment.