Advent Calendar- part 3

9th December

Due to some unexpected developments for the new chain of stores that Diane was responsible for, she had to stay away for an extra night. In our evening skype conversation she cavorted around her hotel room totally naked. This had the effect she desired and my groin was definitely uncomfortable with the evil spiked cage constricting me.

I opened the envelope to find a card saying “Charles, when I get home tonight, you will be put in a predicament for an hour.”

She laughed as I read it out before announcing. “That means tomorrow you have 2 hours of predicament bondage.”

10th December

Diane had managed to finish her business and was actually at home before me. As soon as I had finished kissing her she stepped back, picked up the envelope for the day, opened it to read “Diane, on your next Monday meeting with Dee you will wear a butt plug.”

She giggled saying “Oooh what fun, knicker less and wearing a plug whilst in a meeting with Dee, I like it.”

She then said “time to get your two hours underway. Go to the playroom and strip.”

I followed the orders and she came in to the playroom naked. This started the discomfort in my groin again. She got out the single arm binder applied it, making sure that everything was tight. She lifted up the ring at the end and with a rope soon had me bent over in the strappado position. She pulled up a chair and started playing with herself right in front of me. The positioning was such that for me to assist meant that I had to add to my discomfort.

I ignored the discomfort and soon had my tongue helping her along the way to a couple of hard orgasms that had her screaming in delight.

After just an hour in the most stringent bondage she took pity on me and released me from the strappado. She then spread my feet and secured them with a 3 foot long spreader bar, handcuffed my wrists behind me and ordered me to fetch the take away menu and get the telephone. She took her time selecting the dishes she wanted and some of my least favourite ones.

The order was placed and I had to stay standing which started to become very uncomfortable. Luckily for me the time was up and she released me from the spreader bar just as the bell rang to say our meal had arrived.

11th December

Diane giggled in the morning as she got dressed for work. She was careful to wear clothing that was respectable for the office, but also allowed her to start her treat of no underwear for the day at the office.

She picked up the envelope for the day that read “Charles, you will wear some nipple stretchers from when you get home until bed time.”

The day passed uneventfully. As soon as I got home I put on the nipple stretchers. I set the pull to be mild. About an hour later Diane returned from her work, inspected the stretchers, and increased the pull to be almost too uncomfortable.

12th December

Diane got up before me and when I had finished breakfast she gave me the card for her weekend of setting the treats. I opened with trepidation and read “Until we go to bed tomorrow, you will only speak when spoken to. Each reply must include either Mistress or Ma’am at the start or end. The only exception is when we are out in a public place. If you wish to speak first you must indicate this clearly to me and I will decide whether you may or may not speak. Each failure results in a stroke of the steel cane before work on Monday.”

I was as careful as I could not to speak out of turn and address her as Mistress. Even when shopping I was able to discretely address her appropriately and by the end of the day had only managed to fail ten times.

I was also able pleasure her orally enough to be able to get out of that cage I had been wearing most of the week.

13th December

Sunday morning arrived with Mistress Diane requiring breakfast in bed.

As she enjoyed her breakfast, she handed me the card that read “Today you are going to flog me with the Neoprene flogger for a whole hour. In that time, you may only use it on my pussy for five minutes, but you must make me come twice. Failure means the whole of January in the spiked chastity device.”

I indicated that I wished to ask a question, to which she replied “what is it?”

“Mistress, what happens if your second orgasm is so hard that I cannot flog you for a full hour?”

“I will decide afterwards, if that occurs.”

After we had our lunch she decided it was time for me get her ready for the flogger. I put her in the standing spread-eagle position, secured a blindfold to heighten her senses.

I carefully spent a lot of time flogging her back which had her writhing pleasurably. I moved to her front and let enjoy the gentle caress of the flogger at full strength on her magnificent breasts. When I was satisfied that she was ready for the first set on her pussy, I used just a few strokes to get her to come hard.

Once her orgasm had finished coursing through her body I started over again on her back to allow a short recovery before moving to her front and let the flogger bring her to full arousal. I had her begging for me to strike her pussy again. I let her plead for about five minutes before striking her clit just twice before another orgasm ran through her. She slumped in her bindings. I quickly released her legs, and holding her tight released her arms and carried her to the sofa, holding her as she twitched for nearly half an hour.

When she was ready she asked me whether I had been flogging her for the full hour.

I replied nervously “No. It was just forty minutes Mistress.”

To my relief she said “Well, you did well, so I will not call that a failure.”

14th December

We got up a few minutes earlier than normal to allow for time for me to get the eighteen stripes I had earned over the weekend. She took great delight in leaving me with a striped bum with some very prominent welts that I knew I would feel for a few days.

She dressed for work and carefully made sure that she had a butt plug in her bag for her afternoon treat from a few days ago.

She opened the envelope with the card reading “I am sure you will enjoy wearing the tack bra for a day at the office. (If by chance you are enjoying the no underwear treat, this can be postponed until that treat has finished and you will wear on the following full working day.”

She glared at me, looked at the calendar and said “Shit that means the first working day after Christmas I get to have my tits abused.”

I just gave her a wry smile before saying, “well that is not my problem.”

At the start of her afternoon meeting with Dee I saw her wince as she sat down, and I smiled in the knowledge that she had put the butt plug in. Dee noticed the wince as well and commented “Playing sexy games again I assume.”

Diane blushed a little before saying, “yes we have an advent calendar of treats. Charles is also sporting some stripes from his appointment with a cane this morning.”

15th December

Diane handed me the card for the day. I looked at in surprise when I read “Today all you are allowed to wear at work is a pair of trousers, a shirt, socks and shoes.” I quickly got up, took off my vest and underwear. I relished the thought of having a commando day as it had been a long time since that had last happened.

Wicked Wednesday

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2 Responses to Advent Calendar- part 3

  1. Wonderfully fun . . . wonderfully arousing . . . and wonderfully inspiring!!!
    I’m going to insist on this sort of Advent Calendar for next year!!!
    Xxx – K

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