Predicaments- part 5, A challenge is issued

Tom and Suzy have come to stay for the night and comment was made about us playing before they arrived…….

Before Tom and Suzy could say anything, I asked them to listen Diane explain what we had been up to.

Diane summarised the challenge and described the three sessions in brief, with the only comments being that I had been an evil bastard in my teasing, but that she had really enjoyed her orgasms.

Diane quickly then cleared the dining table put everything in the dishwasher and joined them for some more wine.

When she returned, Tom commented“I am so sorry that we have interrupted your challenge”.

“Well, it is a slight interruption, but I have an idea that you might enjoy.” I replied. “If you are interested in playing tomorrow, it will be playing with both Diane and Suzy and involve denial. ”

“I must admit that I am curious” Tom started, “and intrigued. I have not played many denial games with Suzy, and you know how hard she can play before she starts to space. Are you sure that it will be a fair contest.”

“I understand your concerns, however Diane has yet to survive the allotted time (including penalties) without cumming.” I replied. “here is my suggestion, which is not fully worked out. I know that you have played with Diane and I have played with Suzy before. They also used to play with each other before we met them. They both like being bound. They both have pierced nipples, and we know how they both like their jewellery and each other’s bodies. They are both around the same height so we could have them both facing each other separated by a small tree (or other upright) with them being bound together by their nipples being locked together and their hands will be cuffed together so that they can play with each other’s pussy and clit. They will be secured so that they cannot move out of reach of the other’s hands. The loser is the first of the 2 girls to cum or safeword. There will need to be an agreed penalty to the losing couple. However we should set the maximum duration as the time that Diane would have to hold out until in the next round of our challenge. If they both hold out that long, then we as doms are the losers”

“What have you in mind for as the penalty for the losers?”

“In 4 weeks there is that special Saturday party in Birmingham, we all attend. If Suzy wins, Diane will sub to you and I will sub to Suzy, and if Diane wins the roles are reversed. If the girls win, then you will sub to Diane and I will sub to Suzy. I also suggest that after the challenge the losers are locked into their respective chastity devices until a month after the party with the winners holding the keys.”

Diane added “in our challenge we have included a special caning every Monday for our period of chastity”.

I laughed “It won’t be possible to manage that. How about – the losers receive 6 of the best from their Dom(me) after the party on their sit spots on Sunday after the party just after lunch.”

I then  rose and said “Diane and I will let you have a chat and will wait in the kitchen until you give us a shout.”

Diane and I left them to discuss the germ of an idea, and went to the kitchen where she promptly pushed me up against the fridge and kissed me hard. On breaking away she said “You should have warned me. For that I will use the bath brush on you next time we play together as a punishment.” She continued “I like the idea of playing with Tom, especially as a top, and I know Suzy is desperate top you so I think we might have a fun day tomorrow.”

We were called back into the lounge by our guests, who both had smiles on their faces. Tom said “it’s a bit awkward to play tomorrow as we promised to help Suzy’s mother pack up as she is moving into residential care home next weekend. We need to be there tomorrow around mid morning and expect to leave around 4 to get home. We do really like the idea of the challenge and Suzy wants to top you Tom and it is a long time since I have played with Diane as a sub.”

“Here is our thoughts” Tom countered “in 2 weeks time you come up to our home and stay for the whole weekend.” We do the challenge on the Saturday in our garden as we have a suitable pole, and we don’t have any close neighbours. If it is raining we use the playroom. I think that there should be a forfeit for the losers on the Saturday night and Sunday morning, we go to the party in the roles you suggest and on both weekends the losers get the caning Diane mentioned.”

I looked at Diane and asked “have we anything planned for 2 weeks time?

“No that weekend is free.”

Suzy chipped in, “I’m worried that if Diane leans back too far with her larger nipple rings my nipple piercings might tear”.

“That is a good point” Tom concurred. After a moment he suggested “why don ‘t we put them in their corsets with tightened to half an inch and the laces tied  at the front and secured to the pole so they can not lean back too far. Would that be OK?”

I added “in our challenge there is a doubling of the loser’s chastity and caning if a safeword is used. I know that Suzy does not have a safeword, however on this occasion I suggest that she does as the whole play session may just get too much.”

Diane interrupted me “in the last session which was the third round, I blacked out and did not come round for 5 minutes. I nearly used my safeword, although the intensity of the experience was at my limits, the desperation to win the challenge stopped me from using it.”

I added “we need something so that both the girls could be losers- I know, the use of any certain words, more than 20 times in total from both of them, in the play will automatically mean the girls become losers”

“You devious sod” goes Suzy.

Tom and Suzy looked at each other and Tom whispered something in Suzy’s ear and there was a clear nod from Suzy and Tom said “Ok. However let us add an additional twist in that it is 2 parties we attend in the relevant dom/sub roles if either of them uses their safeword and the losers are kept in their chastity devices until 2 months after the 2nd party.”

Diane smiled and said that she was happy with that and I agreed to it. She then asked what the time they had to manage to make us men the losers. I replied with “4 hours 20 minutes.” Both girls groaned, “You are not gonna win.”

Sunday morning

After Tom and Suzy left, Diane turned to me, pushed me against the wall and reached for my balls. She gave them a painful yank, and said “right you bastard, we have 2 weeks to prepare for this challenge. You can be sure that Tom will be training Suzy during this time, so I need a lot of practice.”

I smiled and replied “of course you need plenty of practice.  That is why I am glad the challenge was not today. There is no way I want to sub to Suzy as I will be a total wreck after the party and it will take days for me to recover. You can also be sure that Tom does not want to sub to you as he has never been a sub outside their private play.”

Diane agreed and then suggested “how about we set up a training schedule for me. Starting this afternoon. I want to see how long I can resist you. As there will be some bondage involved in the challenge, why don’t we carry on where we left off yesterday but with changes to the rules.  I suggest you tie me spreadeagle to the dining table and use all your skills using any toys you want, your hands and your mouth to try to make me cum. The only thing is you will not use your cock which remains in its chastity device.”

“Umm this could be fun” I thought.

Diane continued “The length of time I resist this afternoon is the time I get to tease and fuck you next Saturday whilst you are in bondage of my choice. During that time you cannot cum. If you cum, you will be kept in your chastity device for 3 months and you will get no relief unless I decide I want a fuck. If you hold out, then I will locked up. The loser will be required to pleasure the winner for a minimum of 6 hours each week with their mouth and hands only. These penalties will only come into force one week after the end of any penalties we get from the challenge with Tom and Suzy.”

I replied that was an interesting idea, but I added “you lasted 2 and ½ hours last time. As I will be ramping up the teasing to the absolute maximum, if you cum within 1 and ½ hours this afternoon, you have to suffer a penalty session next Saturday too.”

“What do you mean” she countered.

I laughed and thought for a few minutes and added, “I will write it down, seal it in an envelope that you can open next Saturday whether or not you have to serve the penalty. If you do have to suffer the penalty, it is clear that you will require this intensive additional training. You will keep the envelope until Saturday morning. I can assure you that you will find the session fun, it will push your limits beyond their current boundaries. You will not be able safeword during this session as there will be no need for it. I will still be at your mercy for the Saturday session.”

“OK, I need all the training I can get as I know Tom and Suzy will be doing the same.”

30 minutes later Diane appeared at the dining area to find the table had been laid out as it had the previous afternoon, with ropes attached to each of the table legs and one of her clothes racks from the closet.

“What are you doing with the clothes rack here?”

“All will become clear.” I replied. “The time will start 5 minutes after I have finished tying you to the table.”

I helped tighten her corset which is nicely boned to straighten her posture with her breasts nestled on the support cups at the top leaving plenty of access to her nipples easily accessed. She laid on the table and  tied her in a secure spreadeagle position which gave me full access to her pussy and clit. “I will blindfold you as this will heighten the intensity of this session, but you won’t be blindfolded when you and Suzy are doing your challenge.”

I placed the blindfold over her eyes and made sure that it was well secured, then moved the clothes rail into the position I wanted. “Ok we will now start this afternoon’s challenge. Are you ready?”

“As ready as I ever will be” came the reply.

I started with a deep kiss whilst massaging her nipples so they got really hard. I gently pulled on them to get a husky moan. I reached behind me to get the lengths of strings I had prepared earlier. They were about 3 feet long with hooks tied on at each end. I slipped a hook from each string through the nipple piercing, ran the strings over the clothes rail and added a small weight.

“OOOOOOOOOOOHHHHHHH” at the same time she wriggled as much as she could tring to avoid the gentle tug on her nipples. I knew that she would need to get used to her nipples being stretched for a long time.

I whispered in her ear “ this is only the start my love, you have a long way to go yet.” At the time using my fingernails to stroke her wrists in her most sensitive spots. She shivered in lust, just as she always does, and moaned with lust. I continued on her wrists watching her fight against the sensations with a big smile on my face. After about ten minutes I decided she needed attention elsewhere.

I moved my hands to her pussy which was starting to open and could feel that she was getting warmed up. There was some dampness there so I got the little bullet vibe and inserted it and turned it to a medium setting knowing that this was normally enough to make her cum. I started to stroke her upper thighs and pussy lips. I gave her the tip of a finger to suck on and taste her horniness.

I listened to her moans getting harder, “remember the longer you hold out, the longer I will have to suffer next week. Just think of anything other than what I am doing to you.” Slowly her moans started to decrease so I knew it was time to ramp up the pressure. I kissed her pussy lips and teased them with my tongue. I nudged her clit with my nose to tease it. I turned up the vibrator to the maximum and set about using my tongue on her clit. I knew that this turned her and usually she would come within minutes. I could her moans of “YES” and “MORE” getting louder, so I knew that I was getting her going well. I kept on the attack of her clit with my tongue, and her moans started to get quieter. I knew she had not cum, so I was the one now in trouble, as I had to make her cum as quickly as I could. I reached for her butt plug, used her pussy juices to lubricate it and inserted it. She resisted the intrusion for a while then it slowly went in. “OOOOOOOOHHHHHHHHHH” and “Niceeee” came from her whilst I still played with her clit with my tongue.

A change of tactics was clearly needed as I knew she was fighting the sensations so hard. I removed the bullet vibe and replaced with a finger and found her G spot. I slowly moved the finger in and out each time hitting the spot. The wails of lust clearly escaped together with groans of resistance. I added a second finger, then a third to the finger fuck I was giving her. She was fighting so hard, it was visible in her facial expressions. I thought that this was the time to take it to the maximum for the rest of the time. I replaced the 3 fingers with four and slowly introduced my thumb. I gently folded my fingers into a fist inside until her pussy lips were around my wrist. I started to move my fist around inside her and gently moved it in and out. I got hold of the medium sized vibrator turned it on and laid against her clit. All the time I watched her carefully until all her limbs tensed hard, her face and upper body went red, and the veins in her neck started to show.

She relaxed for a moment and then screamed “YESSSSSSSSSSSSSS”, at the same time she clamped my wrist so hard with her pussy that I could not move it, and squirted juices all over my arm. She was gulping for air, gave that smile of total satisfaction, relaxed her limbs and blacked out. I looked at the clock, and saw she had lasted 1 hour 40 minutes.

I waited nearly 10 minutes for her pussy muscles to relax enough for me to pull my hand out gently. I released all her cuffs and removed the blindfold, nipple weights and helped her up to release the lacing in her corset. Her arms and legs were twitching as she always has done after cumming hard.

She started to stir and said dreamily “Fluss, shumm, drub” and other unintelligible words. All the time all that came out was a babble of rubbish. She slowly started to make sense so I gave her a bottle of apple juice to drink through a straw. It took another 20 minutes for the twitching to stop before she could sit up on her own and be safe.

I told her to relax and helped her to the sofa so she could sit down properly and start to get herself together. About half an hour later she had regained enough composure to ask “how did I do”. Well enough to not have another challenge next weekend, and I have to endure 100 minutes of you teasing me next weekend. She smiled with a look of pure lust, “I can’t wait”.

I laughed and continued, “well I have still one week of training for you to go before then, and a week after”.  With that she rested her head on the back of the sofa, closed her eyes and slept for a while.

To  be continued……

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