Advent starts

After the exhibition opening and its success, Diane was my sex slave for the weekend. She was able to complete her challenge of having her allowance of exactly 10 orgasms. (I will tell you what happened sometime in the future.)

Over breakfast on the Monday morning she asked “Can we do our version of an Advent Calendar?”

“Are you sure?”


I thought about it for a moment before saying. “OK, but you are to decide on the challenges for the first two Sundays of December. The rules are the same as last year. If you fail a challenge you get punished with 6 hard strokes of the cane bundle the next work day morning. If you have to miss a day, then the task (and the stroke count) is doubled for each day until you can perform it. Finally, I am in charge of what you wear for the month except the 2 Sundays you set the challenge.”


1st December

Diane was surprised, after showering, to find a full set of clothing out with a small butt plug.

She dressed and as we made our way into the office she asked “How long is the plug in?”

“All day except when you need to go to the loo.”

“That is easy, as it is so small.”

I smiled saying “well, this is probably the easiest of all the challenges you face this month.”

When I picked her up from the office she asked “How did you get that plug to vibrate occasionally, especially when I was least expecting it?”

“Easy, Alex had the remote.”

2nd December

Waiting for her on the bed was a pair of very tight fitting jeans, a T shirt and a waist chain with a small padlock. This was in keeping with the regular “Dress Down” Fridays at her office.

She asked “What happens if I need to go to the loo?”

“Simple, just find me and I will unlock your padlock. But the challenge is if you need to be unlocked more than once before we leave the office, for each unlocking, you get 6 strokes with that nice cane bundle on Monday morning.”

She put on her jeans and realised that they were her tightest ones and the seam at the crotch was tight against her pussy.

The jeans did what I hoped because when we got home that night she was as horny as I had ever seen her after a day at work.

3rd December

She showered and found nothing in the way of clothing for her. She did not find this unusual as she was often naked whilst at home. Over breakfast she asked what her challenge for the day was.

“Simple. Except when we are at the pub tonight, you will be as you are. When we go shopping later you will be wearing a coat that you belt up yourself without using any buttons. You are not allowed to adjust the belt once done up. If you have to redo the belt it is 6 strokes each time you have to adjust it. If you ask me for permission to button it up, it is an extra 12 strokes on Monday, followed by five days in the punishment bra and panties. If that gets in the way of any challenges, then penalty for delaying a challenge applies.”

The day went well. Over a coffee, whilst out shopping, Diane said “This is fun, I am quite nicely horny thinking how many of those passing realise that all I am wearing is just the coat.”

She actually managed the 3 hour shopping trip without having to adjust the belt or ask for a button to be done up.

When we got home she quickly removed it, dropped to her knees and started to give me attention with her mouth. I was soon hard and bent her over the handy chair and we both enjoyed our coupling.

4th December

I was both excited and nervous about what she had planned for us.

I got out of the shower to just find my cuffs on the bed. I quickly put them on and went to the kitchen. She had me sit on a chair, locked them together behind my back so I was effectively locked on to the chair. As she put a bowl of cereal in front of me she said “Today you are not going to be able to do much for yourself. I will be teasing you all day and you are not allowed to cum at all until bedtime.”

The first thing was she had to feed me my breakfast. When she was ready she released me from the chair and led me into the living room, sat me down on one of the chairs with my arms still behind my back she sat on my lap, offered up one of her nipples requiring me to suck and play with it. She kept me working her over using just my mouth until she had 3 orgasms. I was so stiff, that she even rode me to a fourth orgasm for her.

Thankfully she stopped her teasing until the afternoon, when she repeated the process. This happened again in the evening.

As we went to bed, she said with a smirk “Well I have certainly enjoyed my day, and I am so tired, you will just have to wait until tomorrow for your release.

5th December

In the morning Diane found her office clothing laid out on the bed with a short note saying “tonight you will have to face the challenge.”

After our evening meal I said “time for your challenge.”

We went to the playroom. Waiting for her there was one her most hated predicaments as she knew she would end up with sore pussy and nipples. She stood patiently whilst she was standing on two blocks of wood with her feet spread apart by a two foot spreader bar. I positioned the chain tightly so her pussy was split by it without it digging in. I then added the strings to her nipple rings so they had no slack.

I removed the blocks of wood so she had to stand on tiptoe to avoid the pull on her nipples and crushing her pussy.

I said “You have to stay there for 45 minutes. If you succeed without calling out your safe word, then I will make sure you are well satisfied tonight. Failure means you will be teased to distraction until you manage to get to sleep.”

I am pleased to say she managed to complete her ordeal, and she was a very satisfied woman who slept with her sexy well satisfied smile.

6th December

On the bed waiting for her was her usual set of clothes, her ben wa balls and the pussy lock. She inserted the balls, locked up her pussy with the padlock and then dressed.

She admitted to me that night that she had been kept highly aroused all day as she was on her feet most of the time and every movement gave her a pleasant tingling sensation.

Wicked Wednesday

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Exhibition time

In the week after Diane being photographed nude the photographer he sent us, by email, the 12 photographs that he had chosen for display in his exhibition. We were both happy with them all. Diane stood up and wiggled her bum enticingly at me suggesting that he could sell 10 limited edition prints of each.

I quickly emailed him our response, with a special request that would be a surprise for Diane.

I was startled on the Thursday to receive an invitation for us both to attend the opening of the exhibition the following Thursday evening. I thought about it and called Diane to my study and suggested that we alter her plans for the weekend of slavery she owed me. She raised an eyebrow until I showed her the invitation. I suggested that instead of it starting on the following day, we delayed the start until the night of the exhibition opening and continued for the rest of the weekend.

The following day, after consulting with our office colleagues, we were both able to take the last Friday of the month off (although it coincided with Black Friday).

As soon as she left the office she knew she would be my sex slave for the next few days. As I wanted her to enjoy it I gave her the little bullet vibrator which she inserted as we drove to the station to take the train into central London. I reminded her that she was allowed 10 orgasms over the whole weekend starting Friday at 6pm. Until then she was allowed to come as often as she wanted. I then asked “Does my gorgeous sex slave want an extra little challenge from Friday?”

“What do you mean?”

“Let’s just say it will be fun, but also potentially frustrating for you too.”

“I’m intrigued, and as you know all too well I am up for most things, so yes I’ll take you up on your challenge.”

“I knew you would, so here it is. You are allowed the 10 orgasms. Instead of allowing you the 10, you must have all 10, no more and no less before midnight Sunday. If you don’t succeed, then you are in your chastity belt until Christmas and I will devise an advent calendar again this year which will be just as challenging, if not more so, than last years.”

Once we got to the hotel we had booked, we quickly showered and dressed for the evening. Diane was wearing a stunning, figure hugging, blue cocktail dress and nothing else. We grabbed a coat each and got a taxi to the exhibition.

Getting out of the taxi, we were surprised at the number of photographers who were busy snapping away. I even heard one ask a colleague “Who is that stunner in the blue dress?”

“I’ve no idea.”

Once inside the entrance I asked Diane “did you hear the comment about you?”


I repeated what was said and she smiled as she added, I am flattered, but I’m not that much of a stunner.”

“You are, and don’t forget it, otherwise I will have to punish you while we are here. I also have an extra rule for you tonight. If anyone asks who you think the model is in your photographs, then you have to admit it is you.”

She looked at me quickly and I could see the concern in her eyes.

We looked around the exhibition of over 100 photographs. Many were of well-known people who were in various states of nudity but not too revealing. There was an alcove on one side of the room where Diane was startled to see a life size photograph of herself facing front with her face hidden behind her eyes.

We mingled for a short while talking to many rich and famous people who we had heard of, but not necessarily knew. I saw Dee and Zack with other people. We went over to them and were introduced to some.

Diane was flattered when one of the major players in the retail industry said to her “Most of the resurgence in Bustards is down to you and Dee. You are causing my managers great difficulties in keeping up. I just wish I could have you work the same magic in my company.”

Diane replied “Thank you, I am flattered, but much of it is down to Dee.”

“Oh it is not just Dee; it is you that made all the difference.”

A few minutes later Dee and Diane excused themselves from the conversation and I saw Dee ask Diane something. Diane blushed, and I saw this as an opportunity to start her teasing for the night so pressed the remote for her bullet.

When she re-joined me she said quietly so no one else could hear “Dee recognised me from the photographs. And not only did you start me up, I think you started her off too.”

I smiled saying nothing.

Much of the conversations in the area where Diane’s photographs were shown were about trying to work out who the model is.

Our friend Celia, who is a famous model in her own right, saw us and came over. She looked at Diane saying “I just can’t recognise the model, whoever it is truly stunning.”

Diane sheepishly said quietly to Celia “well you saw for yourself that figure in August.”

Celia’s jaw dropped and she stuttered “What do you mean I saw that person in August?”

Diane quietly said “Well, it is me in these photographs.”

The evening was drawing to a close when the photographer came over to us. “Thank you for coming. The gallery owners and I would like you two to join us for a quiet meal to celebrate the success of the exhibition opening.”

Diane was a little flustered when I replied “of course, we would love to.”

As we left the gallery, the person on the door asked us to wait a moment. Zack and Dee joined us followed by the photographer. We were escorted out to the car and soon were on our way to one of London’s most exclusive restaurants.

Over a remarkable dinner it became clear that Zack owned the gallery. He said “well, all the prints allowed of that series of ‘the precious beauty’ have sold out. I just wish I could find out who the model is and get them to agree to some more.”

I pressed the button on Diane’s bullet again when she said “Well, I am that model.”

Dee interjected saying to Zack “please turn it down.”

“I haven’t touched the remote all evening.”

“What, it’s been buzzing away for over an hour.”

“Well it is not me.”

Dee then looked at Diane and saw that she too was feeling the buzz from her hidden tormenter. “Oh god, not you two playing again.”

Zack burst out laughing with the photographer looking very puzzled. Zack then said “Charles and Diane are good friends of ours as well as Diane working with Dee. We have also played together quite often, just as you did a few years ago with your late wife.”

Wicked Wednesday

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Three more challenges

Diane here again.

After completing four challenges, I was in the clear from being in my chastity belt. I knew that Charles had got a challenge ready for me for the following day, so I asked “What would have been my challenge for tomorrow?”

“I’m not saying. However if you want to try the challenges for the next three days, you can, failing one means that you are my sex slave next weekend from when you get home on Friday until midnight on Sunday. Success in all three means I am your slave for the weekend.”

“I’m game, and I can assure you that I will manage them all.”

“I’m pleased. I will still control your wardrobe for these three days.”

As I came out of my shower on Friday morning I saw the largest of my butt plugs and a little note on the bed. It read “You are allowed three items of clothing of your choice today including your shoes. You need to choose wisely as we are meeting up with Zack and Dee at the photographer’s studio this evening.”

After dressing in a bra and a conservative business friendly dress I went to the kitchen and asked “How long does the plug have to be in?”

“From now until the board meeting finishes this afternoon. I will be checking on you occasionally to ensure it is still in place. You are allowed to take it out if you need to for normal bodily functions, but it must be back in when you have finished them.”

I bent over, lifted the hem of my dress before asking him “Please lube me up and insert it.”

He ensured there was plenty of lube and it took a few minutes before it finally plopped into place with me feeling very full.

The morning went quickly with Charles gently checking from time to time. As we walked to the board room with Zack and Dee I noticed her walking slightly awkwardly so I asked “Is she really wearing the cilices from Monday?”

Zack replied “Of course, and I can tell you she is finding it very challenging as she can’t cross her legs as well as finding it awkward to walk. I, on the other hand find it very pleasing that she is mincing along as she is, as I think it makes her even more sexy than normal.”

The meeting went well and after it finished I said to Charles “Do I get a reward if I keep the plug in for longer?”

“Maybe. I will think about it.”

I decided that I would enjoy the feeling of my ass being full for as long as I could, so kept it in. The evening in the photographer’s studio went well as we worked out the shooting plan for Sunday.

When we finally got home, Charles led me to our bedroom and said “Your reward is simple. You can have as many orgasms as you want before midnight.”

He then kissed me, played with all my erogenous zones. He made love to me with me screaming out orgasm after orgasm until he finally removed the butt plug. He inserted his cock in my arse and pumped in and out until he finally exploded inside me.

I went to sleep a very satisfied woman.

The next morning I was told my challenge for the day. “We are going shopping. You must have an orgasm in the High Street of our local town, the big DIY store on the edge of town and in the supermarket. These orgasms must be on a shop floor or in the high street itself.”

I was very surprised and said so. He just smiled sating “We know you can come quietly, so you just have to do it 3 times in different places.”

I can tell you that the high street one was difficult as I had to find a relatively quiet place. Charles kindly allowed me to cover my lap with a coat so I could masturbate myself to a climax with no-one actually knowing what I was doing.

In the DIY store I found a very quiet corner and with Charles help I was able to have my orgasm. The Supermarket was slightly different as it was crowded and there was nowhere I could complete my challenge.

As we left the store Charles said “well that was a failure, so next weekend you are my slave. If you succeed in your challenge tomorrow, then next weekend I will allow you 10 orgasms. Fail and you get none and a very sore bum on Monday after your shower.”

We went to the pub as usual, and enjoyed ourselves with John and Kathy. We laughed about the challenges I had faced and they were amused at my failure in the supermarket but understood the reasons why.

Sunday morning came around and I was shocked to find that my clothing for the day was the thinnest sundress I owned and a pair of shoes. I was about to say something when Charles said “That is all you need, as later in the studio you and Dee are going to be modelling some of the items for the catalogue. Your face will be hidden for those. Additionally you will also be nude for a one hour session of art photographs for his next exhibition. I have agreed that he can only exhibit photographs where you cannot be recognised.”

The studio, the photographer was very professional and soon put us at ease with the other models who were quite happy to be prancing around naked between their shoots.

Dee and I enjoyed ourselves modelling some of the restraints. One shot was of me holding a cane to Dee’s bum as she was bent over retrained by her wrists to her ankles. We were both wearing facemasks to hide our identities.

When it came to the final shoot, which was of me nude I had relaxed sufficiently to be able to get into it. Charles also helped me by being very supportive and complimentary about my figure. Finally it was all over and I was shown the photographs of me nude and I was surprised at how erotic they were without revealing my face. He had not taken one shot where I could be easily recognised.

I gleefully signed the model release form for the exhibition. He then asked about sales of prints. Charles said “I am sure that they will sell really well, and I would love that my sexy wife is admired by others without them knowing who it is.”

I smiled at Charles before saying “May I have final say in which ones can be sold once they are printed?”

The photographer said nothing. Charles said “to a degree, but at least half the shots he uses may be sold.”

I knew that was all I would get so had to be satisfied.

Wicked Wednesday

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More challenges

Diane here again. Charles ordered asked me to write about the next 2 challenges I faced.

Wednesday morning I saw the clothes he had laid out for me. A very thin white bra, dark blue blouse with a black jacket and skirt were laid out on our bed. As seemed usual for this week there were no knickers.

I dressed, did my make-up and hair. He came back into the bedroom wrapped in the towel. I asked “so what is the challenge?”

“It will be revealed when you get home. All I will say it is a sexy one.”

The day passed slowly and every time my mind wandered my pussy moistened in anticipation as I was thinking “What does he mean by a sexy challenge.”

I got home slightly later than usual for a day spent in the office to find him already there cooking our evening meal. He said “Please go and remove your clothing and then come back here.”

I did as asked, knowing it would be a sexy evening I added a little perfume before getting back to the kitchen. He broke off from chopping up the vegetables. He asked “ready for the first part of the challenge?”

“As always.”

He had me squat against the wall with my feet in front of me and my back flat against the wall. He had me stretch out my arms horizontally and placed a round pencil on thewall back of my hands. He said “You have to hold that position for 10 minutes. If the pencil drops before the 10 minutes are up that means you have failed this part of the challenge. If you succeed then you will have a pleasurable evening, failure means that you will be struggling later.”

He had me placed so I could not see any clocks. I soon felt the strain in my arms as I held them level. My leg muscles took a bit longer before they too became painful. I struggled to hold the position. After what seemed like half an hour my arms gave out and the pencil dropped.

“Oh dear, you only managed 8 minutes 39 seconds. That means I will enjoy watching you struggle later.” He said as he helped me up on to a chair so I could let my legs and arms recover.

After the meal had been cleared away he guided me to the playroom which he had prepared earlier. I was placed in a standing spread-eagle with my feet stretched apart by the 3 foot long spreader bar. He kissed me with me responding as usual. He broke away picked up the neoprene flogger saying you have 20 minutes with this. The last 10 will be on your front followed by your pussy getting 81 strokes of this. Because you failed the challenge earlier you do not get to cum until the 82nd strike. I won’t even tell you how many strokes you have received, so you have to keep count.”

I groaned before retorting “You know how that flogger does me in every time it gets to my pussy.”

With a sardonic smile he said “I know. If you had lasted the full 10 minutes you would have been able to come as often as you wanted.”

He moved to my back and the swish of the flogger followed by the pleasant sensations soon had me purring. He moved to my front, stroked across my breast, before laying into them as hard as he could. This had me purring even louder before he switched his attention to my pussy. I concentrated hard on mentally counting the strikes as I fought back against the strikes that would normally have me in orgasmic bliss in the first 20 or so blows. I manged to count in my head up to 65, but the effort of fighting the orgasm that was building up inside me was so much that I lost count. I fought hard to hold back and when I eventually could not hold back I came hard. I must have passed out as the next thing I consciously knew was that I was being cuddled by him on the bed and I was twitching hard.

I eventually asked how I did. He replied “you did really well, it was 96 strokes before you came, and it was a very hard one, so you succeeded.”

He held me for ages before eventually taking me off to our bedroom to sleep.

Thursday morning after my shower I saw that he had selected a trouser suit for me. Laying on top were my ben wa balls and a padlock. I realised that I had an interesting day ahead.

Before putting on the trousers I inserted the balls and closed the padlock through the rings on my lower lips locking them in.

At breakfast he said “At lunch time find me for the key so you can remove the balls. If you want to remove them earlier than one o’clock then you fail the challenge.”

I replied “It is not quite that easy. I am not in the office today; I am visiting a couple of stores today.”

“You normally do store visits on Tuesday or Wednesday.”

“I know that. I changed my schedule because the manager of one has asked me to visit his store as he has some ideas he wants to discuss.”

With an evil grin he commented “Oh this is even better, you will have them in you until you get home then.”

The journey to the stores by train was mainly uneventful; however the tube train between stations was packed and I had to stand. The rattling of the train had the balls move around teasing me. I could even feel myself getting wet as they did their work.

Apart from the balls moving around inside me, the day went well. I even had time to talk to him on the phone, and he got me all warm and fuzzy with his sexy remarks. He teased me about the balls with me replying “It is really fun and sexy. I can feel them moving around and I am enjoying the tease, although a bit more and an orgasm would just make the day better.”

I finally made it home later than usual. I kissed Charles on getting home. He responded well and I was soon starting to undress him as he did the same to me. I politely asked if he would give me the key so I could at least remove the balls.

He laughed as he said “It is somewhere in your handbag. I put in there before you left this morning.”

Wicked Wednesday

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Diane’s Challenges

My punishment for Diane’s naughty subterfuge started on Monday, with a challenge a day for a whole week.

As we got up I asked “How’s your bum, pussy and tits?”

“My bum is very sore, my pussy is ok and my tits a little sore, but I will cope.”

“Good, this week you get a challenge a day, each one you complete successfully gives you a week less in your belt; however each failure adds an extra week of confinement, so you have plenty of motivation to succeed. If you manage the first four, then you do not have to complete the other three.”

“Sounds good to me.”

“Just to add to the fun, I will be selecting your clothing for the whole week and I will make sure that it is suitable for you to wear in the office. Now go and shower, whilst I get your wardrobe ready for today.”

She did as asked and I laid out a very simple jersey style dress, suspender belt and stockings and a pair of 4 inch high heeled shoes. I added 2 envelopes. When she had showered I told her to put on the clothes laid out, and wait without opening the envelopes.

I showered and when I got back to the bedroom I asked her to select one of the envelopes. I smiled as I saw what she had selected. I grinned as I said “The other one is your challenge for Friday. For today you need find me about 15 minutes before your afternoon meeting with Dee starts.”

In the office, at 1.45 Diane promptly arrived at the area I was working in. I looked up at her smiled. I handed her a little bag and said “your challenge is to put these on with the laces so on one side it at the front and the other at the back. When you have done that, tie the lace at the back to the other side leaving a little slack and the same at the front. They stay on until we get home.”

I watched her look into the bag, go a little red faced. I reminded her, if you don’t do it is an extra week in the belt, or maybe a week less if you do.”infernal_2_cilice01_final

She smiled as she replied “Well I am not going to fail on the first challenge.”

She came back a few minutes later handed me the bag and discreetly showed me that she had followed instructions and was wearing the 2 Cilices that were also acting like a mini thigh hobble.

We went to Dee’s office with Diane walking almost normally, wincing slightly as she dug the spikes into herself by taking too long a stride.

Dee welcomed us both into her office and before we started our business she noticed Diane sit down carefully and asked about our weekend. Diane told her and Dee smiled saying “Sore bum and tits as a penalty for some orgasms, sounds fun.”

“Not my kind of fun as it was that evil cane bundle at a hard setting. I was really screaming at the end.”

“Oh well, that is all over now.”

“Not quite, I have a chance of getting out of belt time completely and my first challenge is in place.”

“Playing in the office again? My my you are naughty.”

Zack entered as she said that last comment, and asked “Playing at the office again? What are you 2 up to?”

Diane told him, and he smiled as he said to Dee, “I like the idea of discrete play and punishment. Next time you swear I will have you wear the cilices all day from when you get up until bedtime, locked together. Now that will be fun to watch.”

I smiled at Diane with a little cock of an eyebrow and I could see that she got the message.

The meeting went well and Dee was far more restrained than usual. The biggest issue was relating to some issues from one of the major suppliers. Dee swore as she heard this before she said “We better F***ing look for an alternative urgently.”

Diane calmly replied, “It is all in hand.”

Zack smiled at me asking “can I borrow your cilices for Friday?”

I replied “of course.”

Dee said nothing, but the frown on her face said it all.

Diane successfully kept the cilices on until we got home, although when she crossed her legs once, she quickly moved them back.


Tuesday morning came around and Diane did not find any clothing waiting for her after her morning shower. I told her “Your challenge for the day is for you to be totally naked until you get to the office car park. Then after work you will strip off in the car park and come home naked, staying like that until bedtime.”

She wiggled her bum a little saying, “At least I can be warm in my car.”

I reminded her that “your car is being serviced today, so I will be driving the Stag today, and it is a nice sunny morning.”

She shuddered on hearing this saying “I’m going to complete your challenges so I can be free of belt time.”

We went out to the car, I lowered the top and Diane sat in the imagespassenger seat, knowing my views on her slouching down, sat up properly, put her seat belt on as I lowered the top.

The only time that she might be showing off her glorious assets to the general public was if we got stuck in traffic.

The drive to the office was uneventful and in the car park I handed her the clothing I had selected which was, of course, totally in keeping with her being a high ranking member of staff.

That evening, after work she got to the car and realised that I had parked close to one of the bright lights. There were quite a few people around so she discreetly removed her skirt, tights, knickers and was shielded by the door before getting in the car to remove her blouse and bra.

The drive home was in the dark and she was less likely to be noticed, especially when we got held up by traffic.

When we got home, we both had some work to do so we decided to have a meal delivered by one of the local take away. She placed the order and was told it would be about 45 minutes. When the doorbell rang about half an hour later, I was just finishing up so I had her answer it saying “No hiding behind the door.”

She was a little embarrassed by this, but rose to the challenge beautifully and without embarrassment collected our food off the slightly startled delivery woman. I heard the woman apologise “I am sorry, I know I’m a little early, but your order was ready and it is on my way home, I hope I haven’t disturbed you.”

“No problem, I am often like this around the house.”

Wicked Wednesday

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