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Diary Dates

Posted on 07/11/2018 by sissie billie

This was a topic that was on our wordpress blog but I thought that it is probably worth extracting a few bits from it and posting it here as we have just had over this weekend a diary check between the three of us, Madam, Sir and myself

We do this every 3 months or so to just sort out what we have planned in our vanilla lives and also what we have planned in the FLR and Cuckolding life.

So after lunch on Sunday I was sent to change into my Sissy Secretary outfit as not only would I be updating my diary I would also be responsible for updating Madam’s calendar and making the bookings for any events or outings that were going to be discussed, in my role as the Sissy PA to Madam and Sir.


The idea is that we inform each of ourselves what we have planned and when and where.  there are a couple of reasons for this, the main one is to allow all three of us to know when we will be in vanilla mode, when we are expecting visitors, when Mick will be around and when we have to book or arrange things. 

From Mick’s point of view I let everyone know what work I have and when it is planned such as visits to clients, delivering training and carrying out project audits – things that will have me away from home.  This is also a safety valve so that Madam can keep an eye on my work load.

Both Madam and Sir will talk about their work commitments that will have them away.

There are a couple of Family events such as Madam’s mother’s birthday, the birthdays of our nieces, John has the birthdays of his daughters.  All are duly noted in the diaries. 

Then we come to the main events.  As part of the cuckolding conditions, Master John has set some rules concerning dates and events:

1.     Christmas is family time and Alice and mick will have that as husband and wife.

2.     New Year is time with friends, Madam, Mistress Carol, kerrie and billie – Master John may be present.

3.     Valentines Day, this is a day for lovers and is only for Madam and Sir, if it is during the week then Madam will stay over with Sir and at the weekend after the day Sir will take Madam out for an evening or a weekend away.  billie should send a valentines card and gift to kerri.

4.    Alice and Mick’s wedding anniversary, this is their time and should be spent as such.  if it occurs during the weekend then Mick can take Alice out for night – probably in London.  if it is during the week then Mick may spoil Alice at home.

5.    Madam and Master’s anniversary – this commemorates the formal start of the cuckolding relationship.  Madam and Sir will go away for the weekend; billie will be present and be tasked with activities appropriate to celebrate his cuckolding.

6.    Mick’s birthday, this can be a vanilla or FLR event.  Madam has the decision on this matter.

7.    Madam’s Birthday, this is an event where Sir will organise.  it may involve Mick or billie or neither.

8.    Sir’s birthday.  Madam will organise this event and it will not include Mick or billie.

9.    Summer holiday, this will be a vanilla event for Alice and Mick.

10. August Bank holiday, this will be a vanilla start to the week for Madam and Sir with a FLR bank holiday get together with Madam, Mistress Carol, Sir, Master Daniel, kerri and billie.

11. Billie will have 2 period of training with Mistress Carol.  one in April/ May and the other just prior to the August Bank Holiday.

12. Most Saturday nights not accounted for will be for Madam and Sir to go out for the evening to either a pub or to a restaurant.  billie will be required to make the bookings.

We each ran through what was already booked and what we needed to add in and plan for.  I confirmed that I had booked tables for Madam and Sir for the next 2 weekends at a couple of local country pubs.  Madam then spoke about the up and coming Christmas functions that she had with work, one with the Milton Keynes office and the other with the head office in London.  Sir would be attending both as Madam’s Boyfriend, I would be on Driver duty for the Milton Keynes function, but the London function would see me left at home.

Sir also had a couple of functions such as his Office Christmas function which wold be a local lunch time/ evening event just for the staff, it had been booked at a local venue but he would like me to come and collect him at the end of the evening, all were noted into my diary.

We discussed what we would like to have arranged for the new year and Sir spoke about what he wanted for valentines day in general terms – a long weekend away with Madam, the rest of the details would be a surprise for Madam.

As is normal Sir informed me that I would be required to come to his office on Thursday evening as his sissy PA – Miss Billie Watson (we had decided that I would use my Grandmothers maiden name for my formal work name) – so that I could use his work computers and his cards for booking the dinner dates and also the accommodations and any of the other items – such as ordering flower or presents.  Where at all possible I’m required to do this by telephone rather that via the internet.  Sir like to hear me make the bookings in my best female or at least gender neutral voice:

“Good Evening is that “X” Hotel, I’m Miss Watson and I’m calling to make a reservation on behalf of my CEO, Mr John “Y”.  he’d like 3 nights booked please for the following dates.  What suites do you have available?  He is treating his Girlfriend and would like something special.  They will be arriving at 1700hrs can you arrange for a bottle of Champagne to be in the in the room on their arrival…..”

With all of the events that we discuss I’m probably going to be busy making bookings for about an hour or so – the “or so” will depend if I find myself having to provide Secretarial services to the boss!


By the end of our kitchen table chat we had a good idea of what we had planned and what we wanted to do for the next few months, it would now be a case of book everything and get the confirmation of the things we had already planned in outline previously.  And my nearest appointment would be going to Sirs office on Thursday, we’ll see what that brings.

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