After a challenge had been issued to our friends, we agreed to do it two weeks later, so the training had started.
After a leisurely breakfast on the Saturday morning a week before the challenge with Tom and Suzy, we talked about the training she had received in the last week to prepare her for the challenge with Suzy next weekend. We talked through all the teasing I had done, and I complained that I was getting worn out with all the fucking as she had been controlling her orgasms so well. “Remember 2 nights you never even orgasmed, yet you seemed to be well satisfied”
“Ummmm they were nice, but a bit frustrating for me as you know how much I love to cum” she retorted.
She then surprised me with “I know I don’t have a penalty to suffer today from the fun we had last Sunday, I’m curious to know what you had thought up and wonder whether to still go for it.”
I thought about it for a moment and said “if you open the envelope containing the challenge and decide not to go through with it, then you will be in the cage for 6 hours tomorrow, during which time i will tie you to the bars and tease you for up to 3 hours as your training session.”
“I think if I manage to survive your penalty, there should be some payback.” She thought about this for a short while. “So If I succeed today, when I have finished with you tonight, you will be locked in the cage until noon tomorrow.”
I retrieved the envelope from its hiding place. “The penalty actually does not have a specific challenge in it, however if you want to go through with it, I want to change it slightly so there is a challenge in it” I said handing the envelope over.
I let her finish reading it, and explained the changes I wanted to make. I suggested that if she succeeded with the additional challenge, then I would be in the cage tonight, however if she failed, she would face the session as if she had opened the envelope and not gone ahead. She countered that I would have to spend the day in my chastity device until her challenge to me tonight.
“Done. You, Peter are going to spend a long sleepless night in the cage”.
Diane went and collected the ben wa balls and bullet vibrator. I replaced the battery so to make sure it lasted the full length of the challenge. She put on my device with the some spikes I had not seen before and locked it. She told me that she had ordered them specially and were a size smaller than the ones I had previously worn.
We drove to the Lakeside mall, outside London, parked the car in a quiet area, she inserted the balls and the bullet vibrator. At exactly 11am I turned the vibrator on its lowest setting and we made our way to the shops. We started off at the specialist lingerie shop as we both knew she needed some new underwear. She started looking through the racks and selected a couple of enticing looking bras and a sheer see through nightgown. I approved of her choices and sent her off to pay. As she approached the queue at the till I played with the remote and turned the vibrator to its highest setting. When she had paid and reached me waiting outside, I turned the vibrator back down to the low setting.
She glared at me viciously and whispered in my ear “that was a dirty rotten trick to play. Those extra vibrations really started me going and I am starting to get really horny.” I could see that she was turned on by the experience.
I giggled and reminded her “I said in the challenge that I will change the setting at any time I feel like it when we are in a shop.”
“I did not see that” she complained. I told her to look on the back of the page.
She looked at the page, turned it over and saw the one line in grey print. “That is very sneaky” she moaned “I didn’t notice that when I was reading it. I suppose it is good practice for changes in pace that Suzy might make next weekend.”
We carried on shopping and every time she was with any sales staff, I altered the setting on the vibrator.
After we had left the fourth shop, I noticed that an hour had passed, so i turned the vibrator up one setting to her surprise. “I hadn’t realised that we have been here an hour already.”
In the next store she saw a dress she really liked the look of, but when I looked at the price (£250) I said that it was too expensive. She said it was not especially as it was a really nice look, and was by a well known designer. “At least let me try it on”. Without wishing to get in an argument I quietly said “if you really wanted to try it on, there is to be a catch. You can go into the changing room, leave the curtain open enough for me to watch, remove all your clothes including underwear, try it on and do a twirl for me.”
We approached the changing rooms and the only free one was right by the entrance so anyone entering would be able to see her through the gap in the curtain she had to leave for me. She slowly stripped down to her birthday suit, put the dress on, came out and gave me a twirl.
“You look really good in it.” I admitted. “As far as I know you have never spent that much on a dress, but it is stunning.” It showed her figure off beautifully and made her waist look smaller than it actually is.
She looked at me, “I agree, and I think it is well worth the money, especially as we have a lot more evening functions now than before. I can’t keep wearing the same dress every time.”
“Yes, but the price is a bit on the high side.” I replied. She stood still for a moment and then asked me to join her in the room, smiled seductively, “If you let me buy it, I will serve a penalty of my choice, I can assure you that you will like it.”
“Do I get a say in the penalty” I countered.
“No, but I have never ever done what I am thinking of, and am a little nervous about it. I will never tell you what the penalty is if you do not agree”.
I laughed at her feminine wiles, “Is the penalty to be done today.”
“Oh yes” she said nervously.
“Go ahead, buy the dress.” I replied, curious about what she had planned.
She handed me her bra and panties with a smile and said “look after these until we get home. Yes, I am not going to wear any underwear until tomorrow.”
I looked at her, stunned. “you realise that in those tight jeans you will have to be extra careful not to allow a damp patch to show. It is your choice, and this will not alter anything that I have planned for you today.”
“I know, but if I am to win next weekend, I have to stop myself from getting turned on, so this is good training.”
With this I left the changing room so she could get dressed in private. I was squirming as my cock tried to get hard.
As she left the changing room, I turned the vibrator on full, while she crossed the shop floor to find there was long queue at the till. Five minutes later I turned the vibrator down again. I suggested that it was time for a bite to eat and a drink. We found a quiet corner to sit with our meals, while I also played with the vibrator. As the clock passed the hour I turned it up another setting. When she stood up to go to the rest room, I looked at her crotch there was no sign of a damp patch. I took the opportunity to make a quick phone call. When she came back, she had a smirk on her face.
“What have you done” I asked.
She took a small plastic bag out of her handbag, “I have replaced the balls and bullet with something a little bigger.” She passed me the bag and handed me the remote control for the fairly new Lelo vibrator that we use occasionally. It is 7 inches long, about 2 inches in diameter and has little knobs that usually send her wild. The vibrator was already set at the third level. I played with it under table and watched her reactions. She definitely had inserted it and even at higher settings I could not hear it. “Are you sure you can handle this, as there are another 2 and a bit hours to go, and we have not finished shopping.”
“We will find out. If I come, or get too turned on, then there will be a large damp patch, so there is a big incentive for me not to embarrass myself.”
I laughed and replied “This challenge is really getting interesting. You’ve certainly surprised me with your extras. However I am not prepared to ease off your penalties if you do not complete the challenge we agreed this morning.”
“It has been my choice to up the ante, but then you know I am aiming to win next weekend.”
I had never seen her this competitive and we were both certainly turned on by the scene. I was feeling the spikes from my device and she was looking very dreamy with the stimulation she was getting.
We carried on shopping for a while, me playing with the settings of the Lelo whenever we went in a store. As the minute hand of my watch passed 2pm I turned the vibrator up another level.
She shuddered and asked how much longer she had to last out.
“One hour 20 minutes” I replied.
“This is getting to be really hard now. I am not sure I will make it.”
“You are not the only one who is finding it hard. I am also turned on, but those spikes are evil.”
She laughed and said “I’m glad I am not the only one who is having a difficult time.”
After another half hour of looking and buying, I turned to her and said, “right that is nearly all. Just one more shop and we can go home.”
“What, we have been everywhere that we needed to, and there is nothing else that I am aware of?”
With this I we walked back to the car and drove for about 10 minutes arriving at a small shop called “Family Secrets”. She looked at me with a very puzzled expression and commented we have never been here before.
On entering the shop, we were immediately greeted by the owner. As earlier in the day, I turned the vibrator to its highest setting as she was talking to the staff. We were the only customers in the shop and I could tell she was finding it very hard to concentrate and knew that we would be getting a very personal service.
“I’m John, the owner, how can i help you today?”
I replied “I am looking for a really special hobble skirt for my wife.”
I looked at Diane and could see the first signs of an orgasm coming on. “I whispered in her ear that she was certainly turned on and looking very horny.”
“I am you bastard, don’t think that I will give in that easily” she replied quietly.
We reached the skirts, and John went through the range in great detail. Diane looked at them and shuddered slightly. She does not like being hobbled round her ankles using rope or spreader bars, however she has expressed an interest in other means of restricting her movement. When John reached for the last one in the range, I knew immediately that this was what I had been looking for. It reached mid length down her calves and had two discreet slits from the middle of the thigh down the side. There were a series of buttons sewn on to the front panel in a special pattern that was very discreet. On the inside of the back there was a series of button holes so that the two halves could be joined together with varying levels of restricted movement. John quoted a price of £100 which I felt was very reasonable.
John invited us to try it on to which Diane replied “In for a penny in for a pound”. I followed behind them towards the counter and changing rooms pausing picked up an item off the shelf.
As John opened the door to let Diane through I showed him what I had picked up and he smiled and gave a nod. I followed Diane into the changing room. She put on the skirt, and I buttoned her up to the most restrictive level and asked her to look at herself in the mirror on the wall outside. She shuffled out of the changing room, admired herself in the mirror. She commented that it was comfortable and could also be worn as day wear in the right circumstances.
As we re-entered the changing room, I mentioned “you have another 30 minutes to go before you win today. As you insisted on buying the dress earlier and you upped the stakes yourself, I am going to add one more level to the challenge. I have agreed to your two changes, both of which you volunteered yourself. So it is only fair that I have a change. Don’t forget that you want to top Tom, and he has never subbed at a party, so you really need to win. I can see that you are getting very close to cumming anyway, so think of these as the final the real chance to test yourself as at this stage. Suzy will go all out to make you cum. I also promise you that I will not add anything else to today’s challenge.”
“Let’s have it” she said resignedly.
At my request she stepped into her jeans, pulled them up halfway, and stood facing the wall and closed her eyes. I picked up the item I had collected on the way in, and placed the waist strap around her. 2 further straps went under her crotch and were secured to the waist.
I tightened the straps so they were fit properly and she exclaimed “What the hell have you put on me. There is something pressing on my clit.”
I pulled up her jeans and fastened the zipper and top button. I noticed a large damp patch had appeared in the crotch area. I told her she could open her eyes. She looked hard and said “you’ve strapped something on me, but I can’t see it. I’m really struggling now as the Lelo is still buzzing away maddeningly.”
I suggested that we went back out to the counter. John offered her a chair as he could see that she was finding it hard to keep stand up. A side door opened and an elegant woman stepped forward and introduced herself as Kathy, John’s wife. I handed her the remote for the Lelo and pressed a button on the key fob I held in my hand.
Diane’s back staightened in shock as the new sensations hit her clit. “Fucking hell, what have you put on me” she gasped out.
“I have added a butterfly vibrator that only affects your clit.” I played with the fob and altered the settings down and then back up to maximum. “If you survive another 20 minutes without cumming I have to sleep in the cage. If you don’t then you will.”
She gasped, moaned and wriggled around like mad for 19 minutes before she succumbed to all the sensations, she arched her back, her shook wildly, she gripped the chair hard, tensed her leg muscles all the while screaming “Yessssssssssssssssssssssss”. I glanced at my watch, watched her carefully then held her when she slumped forward, out cold. Kathy immediately turned off the Lelo and I turned off the butterfly. I laid her down on the floor, laid alongside her holding her gently. I gently lowered her jeans, removed the Lelo and butterfly vibrators and did them back up again. As always when she came hard her arms and legs twitched and she continue t0 spasm for a while. I stroked her hair gently and when she eventually opened her eyes she slurringly asked what happened.
“You came harder than I have ever seen before. It has taken you 20 minutes to get this far. Kathy has gone to get you a drink, but now all you have to do is lay back, relax into me and recover.”
As Kathy returned with a glass of juice with a straw she said “shan oo”. I held for a long time, whilst she recovered. She started to rise and I helped her onto the chair. I cuddled her as best as I could, and when showed some semblance of sense I asked “can you manage on the chair on your own for a few minutes?”
In her ear I whispered “We will be here for you, but you need to get your senses back properly before we go home.”
John had disappeared for a minute and came back with a tray with three mugs of steaming coffee. In the meantime Kathy gave a thumbs up and mouthed next weekend.
The three of us watched Diane regain her senses properly and she finally asked “did I last the full time?”
“I’m not exactly sure”.
“This is interesting, by my reckoning you came about a minute before challenge. However, I am not going to make you sleep in the cage tonight as you have done really well today.”
John and Kathy looked at us with a smile. Diane was clearly looking a bit worried about the whole situation, especially in front of people she did not know. So I asked “are you ready for a small revelation?”
I asked John and Kathy to put the masks they had worn at a recent party we had attended. When they returned Diane took a deep breath and said “My god, they’re the couple that did that demo on the spider’s web and I said I wanted to be up there taking part.”
to be continued………