Predicaments- Part 2- Saturday morning

I woke to Diane moaning alongside me in the bed. I asked her why she was moaning. Her reply was that I was a bastard and that she was terribly horny.


She complained “I dreamt that you kept teasing me so much that I could not stop cumming all day today and never managed 30 minutes without cumming.” She then added “you kept playing with my nipples all night and my side of the bed is damp”.

I laughed and asked what she was going to do about it. She replied go and cool down in the shower and have breakfast. She asked how long we had before the challenge started for today. I looked at the clock and suggested just over an hour and that we start at 9.00. She jumped out of the bed, rushed into the shower and turned the water on cold.

Once we had breakfast and I got the toys together and I asked whether she wanted me to get the rubber sheet and towels in case she squirted. Her reply was emphatic “Yes, because when you tell me I can cum, I will and it will be hard.”

I went and got a new pack of cards, still in its wrapper. She asked “why the new pack?”

“It means that there can be absolutely no cheating in case any of our other cards are creased and worn and you might know the values”.

She pouted as she knew she was in trouble because she was not able to select one card that she knew was low because it was creased or marked. I allowed her to shuffle the pack for 10 minutes and checked that they were well mixed. She shuffled them once again and I asked to select her card and pass it to me.

I looked at quickly, saw the 9 of diamonds, and placed it in a thick envelope and asked her to sign over the seal. I hard time not grinning widely as I knew that she had to resist for a minimum of 2 hours. The longest she had resisted cumming whilst being teased had been one hour.

After removing all our clothes, I removed her chastity belt and we settled down on the sofa, with her back leaning on my chest. I asked if she was comfortable and ready to start. She asked me how many free penalties she had, and I replied that she will find out later. She swore, told me that she would not cum in the next 2 or 3 hours and she was ready for me to start.

I put the blindfold on her. She asked why, and I said that this was so she could not look at any clocks and concentrate on the sensations. I started to gently caress her stomach with my hands. Slowly moving up her chest towards her breatss. I cupped them both and spent a few minutes kneading them before I started circling her nipples with my fingertips. She moaned and it was clear that she was getting turned on. I continued to tease her without actually touching her nipples.

I then got to touching a nipple, pulling gently with the piercing. All I heard was shallow breaths and clear gentle moans. After about 10 minutes of playing with her nipples I decide then that it was time to ramp up the teasing and started to run my fingers down her arms to the inside of her wrists. I then used my fingernails to gently stroke the inside of her forearms.

“You rotten sod” she cried, “you have not cut your fingernails and you know what that does to me.”

“I consider that the use of the words rotten and sod will incur individual penalties if used again” I warned.

“You bastard” she moaned. I told her that that was definitely an penalty. After 40 minutes it was time to get really serious so I gently stroked her inner thighs. This produced a large groan, and she decided to close her legs. I told her that her legs were to stay open or there would be an penalty for every minute they were closed.

“Noooooooooooooooo that is unfair” she complained.

“It is in the rules, when you have cum you can have a look”.

“I will not cum for a long time yet” she replied half heartedly opening her legs. I kept one hand teasing her thighs and the other tracing a line up her arms to her shoulders, around her neck to the sensitive spot just under her ears.

“No, No don’t go there” she complained.

“Telling me what not to do”, I laughed, “that is a clear penalty, and we know how you like your neck being caressed and licked”. So I started to kiss her neck whilst moving my hand down to her erect nipples.

“You bastard, you did that deliberately.”

“Of course, with what is at stake, I will do my best to get you to lose the challenge” and added “the use of that word is worthy of a penalty.”

As time was ticking away, I thought I should start to really get her horny, so I moved my hand up her thighs and traced around her pussy. I started to stroke her clit and juices start top run down her thighs. I ran a finger through her juices and gently wiped it on her upper lip just below her nose, knowing that this would really make her horny.

“That is unfair, I am trying so hard not to cum, and you do that. You know how horny it makes me.” I ran the finger through her juices again and wiped it on her lip again, with a teasing laugh.

“I know how horny it makes you, this is all part of the challenge.”

As she was so wet I slid a finger in her and started play inside her, she moaned and then suddenly screamed “I can’t help it, I am cummmmmmming”. With that she screamed, squeezed her pussy hard around my finger and gasped.

She came hard, and my hand was soaked with her juices.

I let her recover for a few minutes before I removed the blindfold and suggested she went and got a drink as she needed a break before we would start again.

I looked at the clock and saw that she had lasted 1 hour 5 minutes. As she had cum and incurred one time penalty, I mentally noted she would have to last at least 2 hours 40 minutes next time.

She came back from the kitchen with a glass of lemonade, took a sip and then looked at the rules. Her face dropped when she realised that closing her legs incurs a penalty. She looked at we with a glare and then asked how many penalties had been added.

“You incurred 3 penalties, and a further 3 for cumming.”

“Well, how much time was added during that round?”

“You will find out soon when you the challenge is over.”

I quickly made a note of the penalties incurred so that if the time reached 8 hours, she could not argue with me.

After a about half an hour I asked if she was ready for the next session. I told her that she would have to last a lot longer to win as the time had been extended by at least half an hour.

“I am still horny even after holding back much. I did come hard, but I know I can last longer.”

“There are were still toys I have not used yet, and they will be used before the challenge is over.” I reminded her.

She groaned, and asked if she incurred penalties in the “rest time”. I replied that she did not.

“That is good, you are an evil, sadistic bastard who is going to have to go to work with a sore ass on Monday.”

I laughed and asked if she was ready for the next attempt.

“Go for it you maniac”


to be continued

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