Category: chastity

Thursday Review – Spanked and humiliated

Posted on by Sissy billie

Currently I’m home alone and doing catch up with chores, house work, home related emails and added to the mix I have to do this blog post.

Madam is currently out doing some Christmas Shopping and then she heads over to Sir’s as it is his company’s christmas function this evening.  I may have to go and get them this evening or they may get a taxi as the venue isn’t far from Sir’s house.  If they stay over at Sir’s then I’ll go and pick them up tomorrow to bring them home for sunday dinner.

As explained in the last post we are trying to get our normal routine back and running, and to be fair we are managing it.

Thursday night was review night.  I had been back from work late in the afternoon but early enough to get changed and to be waiting for Madam with her bath ready.  I was in one of my maids uniforms and I already had the evening meal prepared and ready to go once I knew when madam wanted to eat.

When Madam got home the instructions were straight forward.  I was to change into my short maid’s dress and Madam would eat before the review, I would serve her as I should and then I would eat after the review was completed.

At 8pm I presented myself at Madam’s study.  I was dressed correctly and with the tutu underskirt as it holds the skirt higher and further exposes me.

As is the normal, I went through my book with the points that I had picked up and noted, faults and what I thought might get merits.  Madam made notes and ticked of in her book where things matched.  It was then the reckoning.  Madam decided that there was a need for a spanking and also 20 strokes with the paddle. Madam also pointed out that since I hadn’t felt 100% earlier in the week, probably due to me trying too hard with my diet and not getting eating in balance, she viewed this as a self inflicted situation and as such I should be reminded that I need to take better more care of myself. Madam also stated that she wanted to take a few photos of my punishment.

So with the punishments decided I presented myself and received the hand spanking first, madam uses this as a way to warm my bum up first so that I’m ready for the slightly more heavier punishments.  This was followed by the 20 with the paddle.

I was told to kneel so that Madam could get a good feel of how warm my bottom was and also she played with my plug a few time.  She told me to stay in position and left me while she went to get something.
When she came back I was told to turn round and then she started to tell me off about not looking after myself properly.  I sat there while she stood over me and I was scolded in the way that a parent might tell off a child.  I simply answered with “Yes Madam”, “No Madam” and “Sorry Madam”.  It was pointed out that since i still hadn’t fully learned my lesson from the previous weeks I would spend the night again with ‘my friend David’ secured in me.

Madam handed me ‘David and I was told to lift the hem of dress and the underskirt and to give a comparison of my caged clit compared to the 7″ of David.  Madam pointed out that if I continue to ignore her direction she may show this photo to Miss Ellie.  I was made to explain to Madam the difference between ‘David’ and my cage clittie and why I am cuckold.  Madam had decided that i would also have to endure some more verbal humiliations alongside my physical punishments.
I was told to turn around and present my arse to Mistress.  I was told to remove my plug and to set it to one side.  Madam had taken ‘David’ and was applying lube to it as I knelt and I expected her to insert it into my recently emptied hole.  That was not going to be the case.  Madam handed me the dildo and I was told to put it into myself.
As I started to insert it, Madam told me to take my time with putting ‘David’ into my arse, I should take time to slowly fuck myself with ‘him’.  As I put ‘him’ into my hole I followed the instructions given by Madam, and was constantly reminded that it was me that was mounting David, that I was fucking myself with David.  
Once Madam was satisfied with my efforts and as she pointed out she didn’t want me getting too carried away but just enough to be excited and frustrated, she handed me the harness that I would wear to ensure that ‘David’ stayed in place for the rest of the evening.
I put the harness on and adjusted it.  Madam checked that ‘David’ was seated correctly on the harness pad and I was then told to turn around.   

Madam made me sit down and this made ‘David’ push fully into me, she checked the front straps and then fitted the padlock.  I was now secure.  

I was told stand and Madam gave me a further inspection and was content that the harness was fitted correctly.

Madam handed me the keys to the padlock and I was told to take them to her bedroom and place them on the nightstand next to her bed, and that I was not to dally!
When i returned back downstairs Madam was in the kitchen and she had placed my dinner on the worktop and one of the stools next to it, she had removed the cushion from the stool and I was told that I was to sit and have my meal.  Again as I sat  down the harness pushed ‘David’ fully into me.  As I had my meal Madam would chat with me, she would suggest that should get up and go and get something and then come and sit back down.  Once i finished dinner I was made to wash my plate at the sink but again do it by sitting on the stool.
this was the pattern for the rest of the evening.  I would be doing some of my tasks and then be summoned to the living room and then made to sit of the stool while Madam would chat with me.  This continued until bedtime when I had to go up to her room and turn down the bed and then wait until she was ready to go to bed and only at that point was the harness unlocked.
Throughout the evening Madam continued with her verbal humiliation of me, and I’ll admit I was a bit of a leaky mess by the end of it.  Madam knows exactly what she is doing and it is a fine art the way that she can humiliate me knowing what will turn me on. Is it wrong that I so love her doing this to me?
As for her showing the photos to Ellie and David?  Well it is possible, but she may not tell them the significance behind each photo…or the whole significance of it.  I probably need to be on my best behavior, and also make sure that I look after myself.
It is Madam’s Orders after all!

Madam’s Valentines Weekend (and my tasks)

Posted on by Sissy billie
Having had a lovely valentine’s day with Madam, and being downsized in my chastity, it was now a case of getting ready for Madam going away for the weekend with Sir.  Madam had booked the Friday off  and as directed I had planned to do my normal Friday tasks and to keep my afternoon schedule fairly flexible.


so on Friday morning neither I or Madam knew where she was going or the weekend, Sir had it all organised.  Madam knew it was going to be an AirB&B for accommodation for the Friday and Saturday night and that she would be out for dinner each evening and out during the day. 

I helped her pack her bag in the morning, and then went and changed so that I could go for the weekly grocery shopping, Sir arrived just before I was leaving and came in for a cup of tea, so I said cheerio and headed off into town.

I got back about 11.30, Madam and Sir had left and I found a wrapped present on the kitchen work top, a selfie stick to use with the phone that we use for doing some of our photos.  There was also a note from Madam telling me that she had packed a bag for me and it was on my bed (it was padlocked with a combination padlock) and the note also told me to pack an overnight bag with my toiletries and towel, a change of underwear, some male casual wear and bring the camera and phone, with the self stick.  I was told to wait for more information.

At 1.30pm I received a whatsapp message from Sir telling me to get my bags and head to a hotel near Cambridge (address supplied) and ask for a room that had been booked for “billie Watson”. I was to message him to let them know when I arrived.

I got there eventually, despite the Friday traffic, checked in and was told that a room had been booked by my “Boss”.  The room was very nice, I dropped my bags and sent a message.

Madam sent me a reply, with the combination for my bag and also with my 2 tasks for the evening.  These were to involve taking a couple of sets of photos, both as part of a bigger task.  Unfortunately I can’t go into details at the moment until the whole of the tasks have been completed.  The tasks involved a few sets of photos and a few changes of clothes, by the time I had finished both tasks I was ready for bed. That was my Friday evening.


Saturday morning I got a message from Sir telling me to check out of the hotel and to be at a certain Coffee shop in Cambridge by 10.45am and to get myself a cup of tea and just wait and watch.  At 11am(ish) a couple came into the coffee shop holding hands, and very close to each other. They ordered and went to the other side of the room  and sat down, yes it’s Madam and Sir.  

When Madam sat down you could just see the welts of her stockings. They were sat having their coffees for about 20 minutes and during that time I got a few very cuckold/ humiliation related whatsapp messages from Sir.  I had another cup of tea and just watched them from the other side of the room.  They finished and left and I got my next whatsapp delivered instructions to go and do some shopping and get Madam a pair of black panties and black stockings suitable for her to wear for going out for dinner with her boyfriend.  I was also told to go to a certain pub at 1pm to have lunch, but to order from the bar menu, no alcohol, just soda water.


Madam and Sir appeared at 1.15pm and it appeared that they had booked a table in the dining area. I moved to a seat where I could see them better and they could see me.  Once they had finished their lunch I was messaged to go and enjoy some sights of cambridge and get my daily steps in (I’ve been increasing my walking as part of fitness/ weight loss programme to help with my health improvement.)

At 5pm I got a message that “Madam’s maid” was expected this evening and I was sent an address and where to park – this was the Air B&B that they were staying in – to which I got back to my car and headed there.  I grabbed my bags and went into the building, they had the loft apartment at the top of the block, very nice.  

I was sent to the spare bedroom to get changed down to my underwear that I had on under my street clothes.  Madam came to the room and told me what the plan was for the evening.  I would help her get ready, then I would then drive them both to the restaurant that they were booked into and then come back to the apartment.  Once they were finished they might go for a drink but they would get a taxi back to the apartment. 

Madam had packed my dark blue jacket, my sheer trousers and black shoes in one of her bags, so that I would look appropriate as their driver.  She told me to wear the white sheer blouse that was in my bag. 

The jacket just covered the top of my sheer trousers and Madam made the point that I was not to wear any panties so my new pink chastity cage would be on display if my jacket was open.  Also the blouse was a white “pussybow” type of blouse, so there was no way to try and claim that it was a normal shirt, it was very clear what it was.  Once dressed I was sent to get my car from the parking area at the back of the apartment, I brought it round to outside the apartment ready to pick them up, but I had to come in to let them know it was outside.  Madam had handed me one of my face masks as I was leaving so I suspected that at some point there would be photos taken. As I came back into the apartment block Madam was at the bottom landing of the stairs and took some photos with her phone as I came in and some more at the top of the stairs.


Before we left Madam gave me a particular task to do when I got back from dropping them off at the restaurant.  The apartments had a Lift and I was tasked to get dressed in skirt and blouse and take a set of photos next to the lift, one of the photos had to show my chastity.  (you all have to thank Poppet Subslut for this as she has been badgering me to do this type of thing for ages and Madam had picked up on this and so I was duly tasked…..Thanks P!!!!)

With both of them ready I got them out of the flat and drove them into the town centre to the restaurant and then headed back to park up and get back to the flat.

Now the thing is that the whole experience was nerve wracking as the other flats in the apartment block were occupied and I could hear people moving around.  so the there was a constant risk that one of them would come out into the corridors or landings or even use the lift!.

Once I was back in the flat I got changed for the task   When ready I had to get out of the apartment and go across the landing next to the door of the lift.  I’ll admit I was bloody nervous as there were people coming and going from the ground floor flats, I was very conscious of the sound of my heels on the floor and every noise from downstairs.  The things I do for Madam!  Here are 2 of the photos, I was using the selfie stick and was still getting used to it.  I’m sure I’ll get better with it with more practice!



With the photos taken, and task complete I was safely back in the flat.  

A few hours later I got a message telling me that Sir and Madam had just ordered a taxi and they would be back in 15-20 minutes and that I was to be waiting by the door with some wine for my Mistress and her boyfriend. I was told to be in my pink cuckolding outfit.

I got a message telling me that Sir and Madam had just ordered a taxi and they would be back in 15-20 minutes and that I was to be waiting by the door with some wine for my Mistress and her boyfriend. I was told to be in my pink cuckolding outfit.

I had to rush to get changed and dressed, I was about halfway through getting ready when another message arrived telling me that they were about to arrive and that I was to be ready with my panties lowered so that Sir could see my new chastity (he hadn’t really seen it earlier.) so it was all a bit of a rush to get finished dressing. The message also said that I was to have the door to the Flat fully open so that I could be seen as they came up the stairs (and anyone else for that matter) – I was to be exposed again!

I added my face mask to my outfit as I figured that there would be photos taken.

There has been a few additions to the cuckolding outfit. One of which was the modification of the front of the dress, this was based on the suggestion from Poppet. I’ve added a series of press studs on the inside of the front of the dress so the front can be clipped up to have me on display or dropped if Sir wants me covered.

Madam had found a pair of pink heels in a charity wedding shop in Milton Keynes, I dread to think what the wedding or bridesmaid dress looked like if these were the shoes for it, you can see they are all very pink!.



Madam also got me a pair of pink garters, one for my leg and the other for a choker, as well as a pink wig just to complete things. All very pink! The last addition to the outfit was a pink corset, a gift from kerri.

Knowing that they were on their way into the building made me rush, I got the wine poured, the front door of the flat open and into position with the tray ready for Madam and Sir. I was now stood there with the flat door open and my caged clittie exposed to anyone that popped their head round the corner.

The relief that I had when the sound of people on the stairs turns out to be Madam and Sir! Madam had her phone out and photos were taken.

Yes I know my socks aren’t right and when I pushed down the pantie bloomers it moved one of my stockings, also the bow in my hair wasn’t square on, so all of these errors in my dress were pointed out to me so that they could added to my review book for thursday night, when my bum would be made to suffer for my lack of attention to detail.

Sir, gave me a good inspection particularly the new cage and that resulted in a lot of verbal humiliation.

I spent the evening carrying out maid duties, both in my exposed dress and also later I was directed by Madam to remove my dress and to serve just in my underwear. When not required I was put in the corner of the living room, with the occasional comment directed at me about how pink suited me.

Eventually with the bottle of wine finished Madam and Sir retired to their bedroom and I was dismissed to my room with the instruction to keep my door open so that I could hear what they were up to and incase I was needed. I was also told that they would be having a lie-in in the morning so there would be no need to make breakfast.

My services were called on once during the night, for both Sir and for Madam.




In the morning I was up and on the go for 8am, with having made some tea when Madam appeared, I provided her with a cup of coffee and she sat down with me and asked if I had been alright with the weekend and also with the elements of exposure. It was a fair question and I explained that while I was very nervous (ok I was more than nervous) about the whole thing I did get a buzz from doing it. I explained that I wasn’t sure about doing it too often but I would probably be ok with the occasional bit of exposure.

We chatted for a short while and I made Alice another cup of coffee for her and a tea for John. I asked what the plan was for the day and I was told that once I was ready I could head back home and Alice and John would be back later in the day, they were going to have a bit of a trip out to a few places around Cambridge and then grab a pub lunch somewhere that John knew of.

so once Alice headed back to the bedroom I went and grabbed a shower, dressed and packed my bags to head home to wait for them to come home later on.

The weekend was far more interesting than I had expected, considering I thought that I would be at home all weekend receiving updates by whatsapp, so being involved was great and my forced exposures were nerve wracking but yes I’ll admit I did quite enjoy the element of risk to it (Poppet you have a lot to answer for!). I’ll have to see what my next set of tasks are!

Valentines Day at home together

Posted on by Sissy billie

This Valentines Day there has been some changes for me. The first of which is that Madam did honour her promise and let me out of my chastity cage on Valentines day.


We both decided that we would take a half day from our respective work and spend some time together, Madam has done a number of extra hours over the last 6 months and with the end of the financial and HR year coming at the end of March she needed to use her extra hours.  So with time in hand she booked an afternoon off to be with me for valentines day.

In the morning we exchanged cards and our usual small gifts, pair of stockings from each of us.  I had informed Madam that I had booked us in for an afternoon tea and that would be for 2pm and we need about 30 minutes to get there.

Madam was home just before 1pm and went and quickly changed ready for an afternoon out with me.  We had a really relaxed afternoon and the place we were at did a really lovely job of the afternoon tea.  The cakes were fantastic and as we found out all were home made by the owner.  I had a feeling that Madam enjoyed her afternoon out, as the journey back home in the car had Madam being a little bit “touchy feely” with me, rubbing my caged groin and playing with my suspender straps through my trousers. Thankfully I managed to get us home in one piece.


Once back home Madam told me to strip down to my underwear. She gave me the once over and told me to go and change and come back in one of my basques and wearing stockings, and to put my satin dressing gown on. As I went to change, Madam went upstairs.

I was back in the living room, Madam called down to open some wine and to pour two glasses, she would be down in a minute.

As I brought the glasses into the living room, Madam appeared in her silk dressing gown and it was clear that she was dressed similar to me with lingerie and stockings underneath. I was told to put the glasses down and to come over to her. She produced the key to my chastity and opened my dressing gown and pulled my panties down so that she could get to my cage.

“The rules are simple Dear, this is mine.” she held my cage, “once I take it off, no touching unless I tell you!”

“Yes Madam!” was all I could answer, well what would you say to this wonderful woman that was going to unlock you?

“once this is off then, you can relax, until I cage you again, it’s just your wife not your Mistress, Ok?”

“Yes Alice.”

she unlocked the cage and told me to take the back ring off. Both parts where set on the coffee table and then Alice came close to me and we hugged each other and started to kiss. The kisses were all very light but with passion and I must admit I let Alice take the lead and I followed very willingly as the kisses progressed to open mouthed and then to tongues.

I decided to match her lead and moved to the couch so that we could sit down and with that we started to make out. I love it when we do this, it is great, very intimate. No one is touching clits, pussy, arses or tits, but it has roaming hands, legs crossing and sliding against each other.

Now, here is the thing, after months in chastity, this is a trick that Alice has, if you touch the freed clit too soon it will go off too soon, probably even before it gets hard. however a long session of building up the turn on, becoming more erotic, it is a great way to get the life back into the freed part of me.

And it was working!

Alice would take a drink of wine and then kiss and we would swap it between us. I would kiss her neck, I’d whisper naughty things in her ear and then go back to kiss her neck a little more.

As things went on I had progressed to taking my kisses from her neck and down onto her chest, eventually I was kissing the tops of her breasts that sat nestled in the cups of her basque. Both our dressing gowns were open but our hands were still roaming over the Silks and satins, which was fantastic.

As the afternoon progressed we were both getting worked up. it was really lovely to simply be doing sensual worship of my wife, and to have similar responses back from her.

By the time we had the wine glasses both emptied, Alice told me to go and refill them and to come back and take her upstairs to her bedroom.

Once up in the bedroom, we resumed fooling around. By this point the dressing gowns were off and discarded on the floor, my knickers were down in the living room some where near the couch.

Alice told me to remove her panties, which at this stage I must say where rather damp. I gently eased them down her stocking clad legs making sure that I placed kisses every couple inches down each leg until her panties were clear of her feet. I slowly worked my way back up her by placing more kisses on her wonderful legs.

As I got back up level with her, she eased me on to my back and straddled me.  she adjusted position and eased me into her.  I was told to just lie still and let her “deal with things”.  I placed my hands on her hips and simply watched her make love to me.  
With the start of our FLR, Alice set the rules that I would not fuck her, it was my job to make love to her, in physical and emotional terms.  So this was not fast, it was slow and deliberate and while this was amazing for me, Alice was clearly enjoying herself, which made me incredibly pleased. As things started to build for both of us, I let her know that I was about to cum.  She didn’t stop, but continued with her current rhythm, she saw that I was about ready and she took me right through to my climax and beyond.
As I gathered my wits about me I reached up and pulled her down on top of me and kissed her, very deeply and with as much love as I could show her.
I rolled her over onto her back and without a word I eased myself down her body.
“you don’t have to” she told me.  but I did have to, she hadn’t orgasmed and that just wasn’t right so I set about my gentle task of making sure that my wife was fulfilled.  Using my tongue and lips I licked, kissed sucked and licked again to slowly build her climax.  Yes I was eating my cum but that wasn’t my concern, it was making sure that she was loved by me.  
She had placed her hands on my head and I can tell when she starts to get close by the pressure being applied onto me by her hands.  As she had done for me I continued with my work as she climaxed.   
  
As she released my head I took that as my queue to stop and I looked up at her and just little kiss around her her mound and tops of thighs.
As she got her breath back and started to calm I was told to come up the bed and we cuddled, with the occasional light set of kissed.  we stayed like that for quite a bit of time, just calming down.
we eventually decided to move and get up.  We went and had a shower together to tidy ourselves up.
when we got finished we realise it was a bit later than expected and I went to the kitchen to make something for us to eat.
we sat and ate.  The conversation was light and would have seemed just a normal conversation if it wasn’t for the fact we were both sat there at the dining table naked apart for open satin and silk dressing gowns.  (Well, our house and life is certainly not the normal that you would expect else where.)
As we were finishing Alice told me that she had another valentines present for me and that it would be best if I went and put some clothes on for it.  Alice suggested another one of my basques and the stockings that she got me for valentines.  So once the plates were cleared I went and dressed.
Returning to the living room Alice handed me a gift wrapped box and a small flat package.  She suggested that I open the flat package first.  Which turned out to be a pink elastic harness for my chastity.  this differs slightly in that it this is a 3 point harness with the third clip that goes at the bottom of base ring and has 2 straps that go behind the thighs to then clip onto the main strap.  These straps further help to reduce the bouncing of the caged clit when being used by Madam or Sir.  I thanked Alice and she told me to open the box.
as soon as I opened it I could see that it was another chastity cage, the rings matched the ones that I already had and as I pulled out the actual cage I could see that it was the cobra nub, the smallest of the cobra cages.
It would appear that I was being down sized.
While I looked at the cage and sorted out the base rings to find the right sized one, Alice went to get the KY gel.  When I put on my cage I take a small amount of KY and apply it all around the ring, this helps to get my balls and clit through the ring and to get it settled into position.  With another bit of KY I coat the inside of the cage and apply some to my clit, this all helps with sliding it into position.
Alice had retrieved the lock and key from my other cage.  She was going to use the old lock as my spare key was held by my other keyholder – Carol – this would mean that there would be no need to swap keys with her, the old lock would be just fine. 

The cage went on without too much fuss.  The biggest hassle was aligning the 2 support “lugs” each side of the lock block.  with more of my clit compressed, there was more skin to get in the way, so the main task was to make sure that there was no pinching.  Once located Alice slid the lock into place and removed the key.  I was now back to being fully secure.

I added the chastity strap and it did hold everything very snug to the the body.

I was told to go get the other cobra chastities so that she could take a photo to show how I had progressed over the last 18 months.

I was told to sit on the couch and spread my legs so that she could get a couple of photos.

I asked her that now with the chastity back in place was she back to being Madam?  She answered that “Madam” would be back in the morning, until then she was still Alice.
with everything back in it’s place and being all secured we cuddled for a while there on the couch until she told me it was bed time and she took my hand again and led me to her bed.

Alice smiled at me and said “Happy Valentines Mick”.

God, I love that woman!

A rather frustrating weekend

Posted on by Sissy billie

Earlier this month the high winds that hit the UK created some damage  to a building belonging to one of my former clients.  This guy helped me start out on my own many years ago and over the years I’ve helped him with several projects as his business has expanded, so to get a call out of the blue asking for my help and assistance saw me heading to Yorkshire the following morning.

So over the last couple of weeks I’ve found myself travelling up and back to the building that was damaged and also to attend a day of meetings and discussions at his main office near York.  

In most cases for each of these trips North, either by car or train I’ve found myself with an associated task from Madam, such as having to purchase hosiery of some form near to each location.

You may say that this is not much of a challenge but for most of these work trips I’m on a fairly tight schedule and to go and buy something I need to use my lunch break or look for very short detours as I travel to and from the meetings.  When Madam thought up that task she knew it would put pressure on me.

so last weekend found me working, not at home but on site in Yorkshire, acting as the Project lead and coordination between the Contractor, sub contractors and the Client’s factory team.  The job has been a real fast ball of “get things fixed, to get production back!” and this weekend saw the really key elements being installed.  All good stuff! job done over the weekend to have minimum impact or disturbance on the building and workers and the factory maintenance team ready to deal with the internal works as soon as the contractor was done.

It all went brilliant apart from…….Madam’s plan for me.

Madam had been briefed that I would go upto the site on Friday and be back on Sunday.  My client was sorting out accommodation at a local hotel for the 2 nights, so Madam planned to take advantage of the opportunity of me being away from her.

I was given instructions on what underwear to wear for the trip up and back, what lingerie was to sleep in and also to make sure that I had my Bluetooth headphones so that Madam could allow her cuckold husband to listen into what was happening in her boudoir on Friday and Saturday evening. 

Sounds like a plan and my twisted desire for humiliation had me very excited to undertake this challenge.

So on Friday morning I put on the first outfit allocated by madam, the black satin sissy cami and open crotch bloomers  with crotchless tights were the items stated to travel up and back in.  The rest of the items required were in my bag, packed by Madam, and I did a quick check and put “Master” and “Mistress” into the bag, so that I could do some ‘personal training’ while listening to Sir and Madam during the evenings.

The car journey up to the site was OK, I was clearly ahead of the Friday traffic and I arrived at the site at lunch time. My plan was to head to the hotel, drop my bag, change into the next proscribed outfit which was a black bodysuit and tights, add my working clothes over the top, grab a sandwich and meet the contractor on site.

However I got a call telling me to come to the site straight away.  The result was that I arrived and couldn’t change so my jacket was kept on as the lacy straps of the cami are quite large and pronounced and would probably be spotted if I had taken my jacket off. I did manage to swap my shoes and get my site boots on without anyone noticing my nylon covered feet, thankfully!

The afternoon was busy but productive and actually coming directly to site was the right option, but by 6pm I was ready to go to the accommodation, get changed and get ready for whatever Madam had planned for me for the evening.

At that point the client dropped the bomb shell, I wasn’t in the nearby hotel, I was going to be staying with him and his wife in their guest bedroom!  Bugger!

Now, my client is a great bloke and his wife is really lovely, known them both for many years, but I’m not sure that they are going to be that open minded about everything that I’m wearing under my male clothes and also the fact that my bag is full of the delights that Madam packed for me!  My first thought was “Do I have a padlock in my car, so that I can secure my bag while I’m on site.  Unfortunately the answer was no! Bugger…again!

 The next dilemma was “I don’t have anything in the bag to wear other that what I drove up in, (Shirt, tie, tweed jacket, moleskin trousers) and my site work wear.”  

At that point I needed a plan, and thankfully Madam’s earlier task of having to buy stockings and tights offered me a solution.  I made an excuse to my client and told him that I needed to check in with home and let Alice know that I wasn’t going to be at a Hotel, knowing where my client lived I told him that I would follow on once I finished calling the wife.  I got the thumbs up and he left the site leaving me to call home.
I called Alice and gave her the heads up that things were not going to plan and that I was now staying at the clients house and being hosted by him and his wife, so it would be highly unlikely that I would be able to be in a position to be dressed and practising on “Master” or “Mistress” while listening to the bedroom activities  happening 180 miles to the south!

While Madam was quite disappointed, I assured her not quite as disappointed as I was!  We finished the call with “I love you” from each of us and I then put the next part of the  new plan into play.  The supermarket that I purchased the tights from previously wasn’t too far away and as they had a clothing section I made a quick dash to it and spent a very quick trip round the clothing section looking for a polo shirt or something similar to wear.  Having found one I purchased it, removed the tags and added it to the top of my bag.
I made the 20 minute journey to my client’s house and was warmly welcomed by his wife and shown to the guest room and also where the bathroom was.  Once I was sure that she had headed down stairs I quickly changed grabbed a quick shower and put my new polo shirt on.
I got down to the living room to be asked if I wanted a beer or wine as food would be ready shortly, I declined and asked if they had a soft drink as I’m currently not drinking.  As he went to get me a drink my phone rang and I looked at it and it was Sir calling me, I gave a quick look round and answered.
“Hi John, hows it going?” I was trying to sound neutral.
“Hello billie, thought I would let you know your wife is busy on her knees doing your job…”
My client returned and handed me my soft drink and gave me a look, I wondered how loud I had the volume?
“Thats great John, Thanks for letting me know…..hope it’s going ok.”  I said tentatively

“Oh its going great, you know how good she is at sucking me…”
“Eh, yeh, I’m pretty sure that should do the job for you.”  I was being very careful with my words as my client was sat with his beer watching me.
“Well billie, I’ll keep you posted on how things go this evening, keep your phone on, I’m sure that you’ll want to know what we are upto.”
“Yea Cheers John! That will be great thanks, keep me posted on things, I’ll keep my phone on me just in case…”
and with that the call ended.
My client asked if there were problems. I don’t know if my face was red but it certainly felt like it was.  I assured him that things were fine.  I told him that the call was from a Guy that deals with a few things for me and he was sorting out a couple of jobs for me in my absence, which in the strictest sense was all quite true.
We were called to the dining table and sat down to have a very nice meal,  as the meal progressed I could feel my phone vibrate (having turned the volume down).  I knew who was sending me Whatsapp messages
but thought that it would be rude to look at them during the meal.  The conversation was very nice with my hosts and it was good to relax a little even though I was very keen to see what was coming through on the messages.
Finally with everything done, we were going to get up from the table and head to the living room, my hosts with a glass of wine each and me with a coffee, I decided to take a quick look at the messages, they were from Sir and the first was a short clip of Madam showing herself off in her Basque and stockings.  It was a bloody good job I was caged otherwise I would have been sporting a noticeable lump in the front of my trousers.  As it was I was just very very uncomfortable in my cage! 

I scrolled down and there was a couple more photos of Madam in her lingerie, nothing too rude but very suggestive and very erotic for a submissive cuckold that loves to see his wife in her lingerie and stockings!

Sir had added a few comments between pictures with the last one being “Going to the bedroom now, keep your phone on!”
I put the phone away and sat down with my coffee.  My client asked if things were alright?  “Yes, it looks like things are going well” I said a little sheepishly, “I’ll probably get a few more messages keeping me updated on progress.”  I sort of explained that if I hadn’t come up to deal with his project I would have been on site with “John” keeping an eye on his “project”.
My client expressed his gratitude for me prioritising his project over the other one.  That comment made me think as that really wasn’t the case, my relationship with Alice is always the priority, so I simply added  “Its alright, John’s got a good handle on this, he just likes keeping me updated on how things are going.”
the rest of the evening was very good with my hosts, we chatted and caught on some work news and also on some personal news, it was a very pleasant evening.
I could feel my phone starting again with messages.  I left it where it was as I knew there would no doubt be some more pictures of Alice and I didn’t want the risk of my hosts becoming more curious.  I eventually decided to call it a night as we would be on site at 7am and I did need some sleep.
I got to the bedroom and looked at my messages.  There were a couple of messages from Madam and several photos of her draped quite seductively over her bed.  The following photos are not of Madam but they are very close to the type of poses that were sent.  All very lovely and it reminds me why I’m in love and lust with her!

There was several teasing statements in the messages, both from Madam and from Sir, all of which just added to my frustration!  The final message from Madam simply said “Goodnight billie, sleep well, chat tomorrow!”

It wasn’t the easiest night to drop off to sleep but when I did it was with thoughts of my wife in her stockings!
This set the pattern for the rest of the weekend, at various times during the day and the evening there would be bursts of whatsapp messages arrive, some simply stated what Sir and Madam were upto and others had photos of Madam in various stages of dress from fully dressed down to just stockings and heels.  They both kept me fully appraised of what was happening at home!

 By the time Sunday came round we were putting the last parts of the building back in place now that the damaged structural members had been replaced.  I had received my last set of photos, which were quite vanilla, they were of Madam out in a local pub that does a good sunday carvery, but when I looked a bit closer I could see Madam had raised her skirt a little to expose her stocking tops.

By 4pm, everything was wrapped up on the site, it had gone well and despite a few glitches between the sub contractors I was ready to head home.  My client was very happy, he could get work back to full production on Monday morning and the building was back to being safe for everyone in it.  Job done, time to get on the road and to take my very frustrated body back home to my Dominant Temptress.

So, the lesson is when things mess up the plan and it no longer works, change the plan!  I think Madam very much achieved her aim of having me very frustrated and horny, it just was by the means that was originally planned.

Valentine’s Day preparations & Christmas Task Envelopes – Last week and this week

Posted on by Sissy billie

The past week has been a mixed bag of work, and tasks set by Madam. The tasks have been fairly straight forwards and not particularly taxing, they have been a lot less of an issue compared to the previous week’s tasks (Naming toys). However that has all changed with this week’s task.

The first thing on Monday (22nd) morning was when I had to open one of my Christmas task envelopes. This task is going to be somewhat embarrassing to me and I think in 2 cases rather humiliating for me. I have been told that once the task has been complete I am to produce a blog post to further add to my embarrassment and humiliation.  Please, dear reader, you will just have to wait a little while. The task has 4 parts to it and the deadline of the end of February but I have been directed to get it completed at the earliest opportunity.  This is not going to be an easy task for me, it is definitely going to push me into uncomfortable boundaries. 

Last week’s envelope (Monday 15th Jan) saw me me pick up a fairly minor task which was that each day that I was out with work I was to wear one of my bodysuits and tights under my Male clothes. I was also required to carry a spare pair of stockings or tights in my laptop bag, just in case I laddered the pair that I was wearing, if that occured I was to change/ replace them at the earliest opportunity. 

Madam had also included the condition that no matter where I was I was to make a point of going somewhere and purchasing a pair of stockings and tights, I was to show Madam the receipts on Thursday evening at my weekly review to prove that each pair had been bought close to where each of my site visits or meetings had been held. If Madam considered that they were too far from where I was working then I would be punished.

With 2 meetings in London on Monday and Thursday, that was quite easy as there was plenty of places to dash to, to get an appropriate item of hosiery. My visit to Yorkshire was a little bit more tricky, The first day was quite straight forward as the meeting was on the outskirts of York, but a quick detour into the shopping area of the town when I got off the train did the trick. The second day was not so easy as it was more of a rural location and I spent the day fully occupied doing a site inspection and didn’t get finished until nearly 6pm. Thankfully a visit to a supermarket with a clothes section on my route away from the site allowed me to quickly dash in to grab a Bottle of water and a pair of black opaque tights in my size, remembering to take my receipt and to be on the road back home.

While I fully accept that the supermarket was not quite what Madam had planned or hoped for when she set the tasks but it achieved the aim.  Added to which the tights where a godsend on Thursday to wear under my trousers as it was a really cold day.

Friday was a work from home day so no tasks required to be completed, however I did get a run in another pair of stockings over the weekend, the result was that one of the packets of new stockings was pressed into service straight away! The laddering of the stockings has been duly noted in my small note book and I will no doubt have my bum paddled for my lack of attention and carelessness with my hosiery.  For some reason I’ve had quite a few runs/ ladders in my stockings since Christmas, it is become quite a hazard to the welfare of my backside!

On sunday evening one of the things that was discussed between Madam and myself was the forthcoming Valentine’s day. This is normally a day where Sir will take Madam out for the evening, or away overnight (admittedly last year was an exception as well) valentines day at home – blog post 2023. Normally if it is a weekday evening then Sir would take Madam for a meal somewhere local or for an overnight stay to London for a show or for a “fancy night out.” In either case I am normally left at home, generally not even tasked with driving. It was one of Sir’s requirements/rules that Valentine’s day/night was one of his dates.

However I was told that as Valentines Day would fall on a Wednesday, Madam would spend the evening with me. Apparently it was a request from Madam to Sir, which he accepted. I asked if Madam would like me to book a dinner table somewhere but she informed me that she wanted to have an evening at home with me.

Sir did set a condition on allowing Madam to have Valentines day with me and that was that Madam should take Friday the 16th February off work as Sir planned to take her away for a 2 night trip. 

This morning Sir called me to informed me that I should not make plans for the night of Friday 16th Feb or the Saturday/ Sunday, I was to be fully on call from 2pm on that Friday.

It is quite clear that something is planned for all of us in some way for that weekend.  On previous years there has been phone calls and skype calls as Madam was in the taxi with Sir leaving the restaurant or show heading back to the hotel.  I get the impression that this may be something more. 

I’m just really pleased that this year, similar to last year I will get the opportunity to have valentine’s day with my Madam, and it is also not lost on me that Madam has promised to uncage me that day!


You are what you wear

Posted on by sissie billie

The last 2 weeks have been busy on the work front for both Madam and myself, we’ve both had trips away and it has meant that we have spent a few days where our paths have only crossed briefly.  So this post is quite appropriate.

For me there are quite a lot  of times when I have to go out into the vanilla world to do real life tasks or for work. When I do, I need to make sure that I’m dressed the part and appropriate. But there is always the need to meet Madam’s requirements of our FLR and marriage.

For example a normal Friday morning is when I take a trip out to get the weekly shop. To the wider world I’m a bloke wandering about the supermarket with a trolley and a hand written grocery list. what most don’t see is under the Rugby Shirt, jeans and fleece Jacket is the Bra, panties and suspender belt holding up the stockings. Come the summer things normally change to replacing the bra for a cami top.

why bother? why not just put on your jeans and shirt and go shopping?

Well because Madam wants me to always have female underwear on, to always have some form of hosiery on my legs.  During the winter these can be opaques, or if they are lighter deniers then I will have opaque knee highs on as well.

I own very few male dress socks now, most have been replaced with 60 denier knee highs.  The same goes with my male underpants, there are a couple of pairs put to one side in a drawer with my male socks.  Most of my male socks are thick socks for when I have to wear site boots, wellies or if I’m going to do some serious walks (which I occasionally do as a way of getting some exercise without annoying my knee too much).

My day to day knickers are normally from Marks & Spencer and will often be a multi pack of Full Briefs or Brazilian cut briefs, and normally nylon or modal material.  That helps to keep my fancy pants for specific jobs at home when fully in billie mode.

As for stockings I continue to use Charnos 24/7 15 denier stockings, they are a plain top and come in a 2 pack.  They are a good everyday wearing item.  That gets matched up with one of my suspender belts.

when it comes to vanilla work wear, I’m at the stage now where I tend to wear Jacket and trousers.  Often it will be a tweed jacket but the trousers will be a suitable type that would match – tweed, chinos, jean cut (but not blue denim – I feel too old for that) and I also have got in to the habit of wearing a waist coat.  The idea is to try and look smart for the meetings without being too formal and stiff (but I do like Traditional and Madam does like her husband in tweed as well as lingerie).  I also try and use coloured or checked shirts.

This whole set up works really well with wearing my lingerie underneath.  The coloured shirts and waist coats allow me to wear a bra, even when  take my jacket off.  The trousers are thick enough to allow the stockings and suspenders to be worn and the suspender clips are not completely noticeable (you’d see them if you went looking for them) and the leg length, even if they rise up when I sit in a low chair is covered by the use of the knee highs and the way they look like thin dress socks.

 The only sort of variation on this is when we head to see Madam’s family, this normally means that I will switch to either tights or hold ups as the risk of being hugged tightly by a family member (Ellie!) is quite high, so no suspender belt or bra.

The last thing to bear in mind is what to wear to hide your chastity as well as comfort, The cut and style of the trousers does have a impact and as I found to my cost with one cage that having trousers that are too close fitting or of a material that is to stiff or unyielding can be painful – I had a CB-6000 cage split on me when we were driving and I had on a pair of jeans, and that I can assure people is bloody painful.  when I was wearing slightly larger cages I tended to go a size up in waist size of the trousers this tended to give more space in the bum and the groin area.  Its more about the sitting down rather than the standing.  

With the smaller metal and resin cages I can get away with my normal size trousers.  A word of advice – Have shirts of a good length (front and back) and wear a belt with your trousers, unless you want to expose the tops of your knickers, suspender belt or tights to the world.  OK I accept sometimes that risk of exposure is the risk that some people want/ crave. For me it is a case of being discrete about my undergarments when in male mode.

It has been interesting chatting with other submissives about what they would and do wear and there are similar variations for what they wear for public and professional/ working life.  

Some of it relates to how public you are with your home life, how comfortable with being seen as a submissive or sissy.

For some it is just a case of just wearing panties is enough to either give thrill or for their partners to have control over them by forbidding them to wear anything other than women’s knickers.

There are 2 particular examples from my working life that I remember.  One chap that I worked with always wore silk and satin french knickers and was very open about it saying that he found them very comfortable and “felt great”.  There was no submissive or sissy aspects, just someone with a liking of silk/ satin underwear and at the time there probably wasn’t a lot of male boxers in that material, added to which he wasn’t afraid to show people if they asked or if he’d was out on the piss.

The other example was a slightly different reason, a bloke that I had worked with on projects for a number of years and had a reputation for sleeping around – which had cost him his first marriage – was required by his second wife to always wear her knickers from the previous day as well as have his toe nails painted with bright red nail polish.  This was her way of reducing the likely hood of  him straying.  I would think if that was today, my fellow Site manager would have been placed in a chastity cage by his wife!

Having spoken with SaraE on this topic is about wearing women’s knickers for her, as she puts it any type from Granny Panties to Thongs are what she likes.

Kerri, tends to be Enfemme most of the time when not at work – She is a TV not TS  – but for work she needs to be a little bit more conservative with the way she dresses.  Jacket shirt and tie are a requirements, so she says that her rebellious streak has her wearing Cami tops, suspender belt, stockings and panties.  while her shirt tends to be a woman’s shirt (hard to notice when your tie covers the buttons) and she removes all of her earrings apart form a set of plain stud earnings. 

A TS friend that I have and chat to regularly works on trying to have an androgynous style of dressing, she works in a sector that would be very open and welcoming to her turning up to work fully enfemme but as she puts it, that just wouldn’t work with her personal life, but she feels that by selecting a mix or styles of clothing she can feel very femme without attracting too much attention to herself.  In her case I have seen her being able to change her look just be altering the way she does her hair and with a little bit of make up (and I do mean just a little bit.) and occasionally by changing an item or colour of clothing, she can switch between Male, Androgynous and Female quickly and easily.

I had a good chat with Poppet over this and it very interesting to understand what we wear and what we are open or shut about doing and wearing.  The differences for Private, social, public and Professional can be completely different and for all of us what we are wearing at that particular time or role can change the way we behave or present our selves to our variety of audiences. If you have been to Poppets Blog (and I strongly recommend that you do – Link in the side bar) you will know what a shameless exhibitionist slut she is (❤❤💋💋 all said with love!), and with confidence (and she has that in shovel loads) you can carry that off in public – while we Brits often get accused of being prudes we are really quite taken with Eccentric behaviour and having a confidence can carry things through and it’s surprising what you can get away with.  Also when you are in the face of the public- either at work or play, if you’re just getting on with “stuff” most folks with either ignore it or “tut, it just the way he is!”

So for all the submissives sissies out there  – Wear what you are comfortable wearing, in a way that works for your relationship, your life and your work.  And just remember we are what we wear.

The Maid’s Panties

Posted on by sissie billie

 As requested by Sara,

A short post on some of the types of panties that get worn with my maids uniforms, principally the French and the cuckold maid uniform.  This is not some definitive list of the different types of panties that must be worn with maids outfits, only what I have and use specifically with my maids uniforms.

First off is my routine maids knickers/ panties.  These are all satin with white lace around the legs and the waist band.  The lace is soft and not too much.  these are very comfortable to wear and the Satin is very kind when wearing chastity cages, particularly if your foreskin pokes out.

They hug the bum really well and allow the suspenders to be shown. 

The next ones look very similar, as an all satin panty with white lace at the leg openings, however these ones have a Ruched Back to them, that is when the rear of panties are gathered in to the centre of the back and they really hug your arse, following the crack of your bum.

These don’t have lace on the waist band, just on the leg opening.  The seamstress who made these had the Ruched Back as an option on most of her panties that she made.  If you are buying from a Ebay seller that makes their own outfits then give them a call/email prior to ordering to see if they can customise the items for you.

These are very similar to my routine knickers, very comfortable and supportive of the cage.  The lace at the legs isn’t scratchy so pretty good.

With the rear view you can see how the ruching pulls the satin onto the curve of the bum and the centre seem is snug in on my crack of the arse.  These are really comfortable and I don’t feel the need to try and pull them out of my bum.

Another view of the front.

The next pair are again a satin pair of panties this time with more white lace/organza edging.  A bit more fancy, but with the added feature of being fully open crotch – front to back.

All of the openings are elasticated, the satin has a nice feel to it as well – but there is no support as I’m fully exposed. 

These tend to be worn with my short Maids uniform (my cuckold uniform) so that Sir can see that I am caged.

These don’t have lace on the crotch opening, you can get them like that and I have had a pair in the past but a point to note, unless the lace or organza is soft then it can be rough around where it meets your cage, Also Sir wasn’t keen on the lace edge of the crotch opening, as he put it ” very nice to look at but a bit uncomfortable when fucking your arse! take them off!” -just a practical thing to note, so that why this pair doesn’t have lace at the crotch.

The next set is a must for all sissy maids, the ruffled panties!  These can come in a whole variety to types from satin with fully covered in ruffles or just the bum or as these ones they are a sheer black nylon with ruffles front and back.
Madam wanted these so that she could see my cage as I worked about her.  These seem to be a particular favourite of hers when I bring her breakfast in the morning.

As you can see they are quite high waisted, but I think that is so that each layer of the ruffles can be kept separate, you do get some where the ruffling does overlap a lot, if that is your thing then go for it!

The nylon on these is quite soft and doesn’t cause a problem with my chastity and any exposed clitty skin.

You can see that the lace layers are narrow and well spaced apart.  The knickers hug the bum quite nicely.

Something to note – when you go looking for these types of knickers just check that they are maids knickers and not Adult baby knickers otherwise you will end up with a rather baggy bum as the AB versions are designed to take a nappy – not our type of thing, we like things to be snug and well fitting!
Lastly we have a Sheer Organza pair of panties but with the addition of a lace edged cock and bum hole.  Again you can get these in satin or nylon.  there are plenty of Ebay sellers that make sissy items that will add then the openings to the panties.

One of the things to point out to who ever makes them is to make sure the hole is sized to allow your balls and chastity to get through. one pair that we had in the past was only sized to allow my clit to poke through.

The rear hole should line up with your sissy hole, so you might have to send over some measurements to the seamstress and also you may need to tell her what you will need the hole for, Adding or removing a butt plug or if your Mistress or Master plans on using you through the hole, if it is the latter then don’t be too small with your opening size.

This pair is to allow Madam or Sir to remove or add one of the buttplugs.  These tend to be worn with the short maids uniform, again it is because it has me fully exposed and on display.
 I’ve inserted a bit of white paper to highlight the lace around the openings.
There you go, a bit of a rummage through my knicker drawer.  Hopefully that was useful and hopefully the rationale behind each type might be a help to someone.
Regards
billie xxx

  

A week of preperations

Posted on by sissie billie

The previous week has involved a bit of work to get things ready for Madam and Sir going back to work.

I’ve spent a couple of days working with John to get his offices and workshop area all set up for his people to come back to work.  the building that he has isn’t too bad with 2 individual offices coming from a main office on the first floor and the store and workshop area on the ground floor.

The main office has plenty of space for his team to be kept apart but for added re assurance I fitted some Perspex screens to each of the desk areas for him. So his staff have a semi enclosed area but still have visibility across the office.  we’ve increased the size of the table in the break out area where they do collaborative work in the corner of the office, this keeps the space and people apart.  John has his office which didn’t need anything and the second office that is used by his HR/ admin woman is fine as well so long as she just deals with one person at a time.

That was most of the effort on Monday and Tuesday, with both John and myself using our own cars to come and go to collect stores and fixings.  by the time we had all of the screens in place it was about 6 pm so we picked up the tools and called it quits.

Wednesday had me back in billie mode, with Sir sending me over to the office in wig, skirt, blouse and heels to tidy up after the “workmen” had been in.  I provided breakfast for everyone and cleaned up after everyone was finished, and then went and changed out of the maids uniform into a blouse and skirt.

I was given the keys and told to lock myself in so that I wouldn’t be disturbed, before I left Madam check to make sure that I was still wearing my butt plug.  The drive over is always a bit nerve wracking but the bottom line is don’t rush and don’t do anything stupid on the road (and try and keep and eye out for the idiots (they are everywhere!).

So having got there for about 10am, I locked myself in to the offices and started the tidy up of the mess that had been left after the construction works.  Once done it was a case of quickly dust down each of the work areas and then hover the main office before dealing with the toilets.

Madam and Sir came over at 1pm with some lunch and we all sat down for something to eat, all very civilised.  Sir took the bags of rubbish out to his car to take to the tip and Madam asked what I still had to do, which was do a clean of the workshop and store, the tea room/ kitchenette and then the 2 small offices.  I told Madam that I thought that I would be done about 4pm.

Madam told me that she would be back with Sir about 4pm, they would be going to get some tea and coffee for the staff and also to get some new cleaning materials for the cleaners cupboard to replace what I had used.  I was told not to leave until they came back, if I finished early then to send a text.

The Workshop and store didn’t need much work as it is a fairly open area were 2 people work, so there wasn’t too much to do other that a sweep out and mop of the floor.  I sent a text at about 3pm that I was nearly finished and Madam replied that they would be back shortly.

Sir and Madam appear about 3.20pm and I was just finishing the last bits in the HR/ admin office.  Both Madam and Sir went and dropped of their purchases and then made a cup of tea and headed to Sir’s office while I finished off.

I straighten my clothing up and went to join Sir and Madam in Sir’s office.  they were chatting through the plan to have a couple of the staff back into work on the Thursday and then the remainder in on the Monday.  Madam asked me if I would miss my weekly trip to help with the office work with Sir and I did say yes.  Madam must have spotted something in my reaction or my blush.

“Are you going to miss the chance to come out all dressed up or is something else that you are going to miss……?”  yes there was a slight pause before I responded.

“both Ma’am.”  I must admit I did say it a bit sheepishly

“Its what I love about you billie, I’ve created quite a tart, haven’t I?”

“Yes Ma’am.”

“I think John is also going to miss your help in the Office as I don’t think his HR lady is going to come in each afternoon at 3 o’clock to ‘help him with his report’ is she billie?”

“No Ma’am”

I was very aware of Sir chuckling and his comment was “not without a harassment case occurring and I’ll not tolerate that type of behaviour in the company!”

“That’s why you need Ms Watson, John, she fills a gap in your team, a sissy PA or secretary, obviously not full time but I’m sure that she can still come and provide assistance.”

“billie lift your skirt, dear, lets have a look at you?” Madam check the front of my knickers and yes there was a damp patch.

“Well dear husband, why don’t you go over to my boyfriend and show me why he likes taking you to work with him as his secretary?”

I went over to Sir and he turned his chair side on to the desk and I knelt down, Sir had already undone his belt and I opened his fly and he shrugged his trousers and boxers down.  Sir was starting to stiffen when I took his cock in my hand.

Madam had moved her chair round next to Sir and was watching me directly.

“That’s it Ms Watson, show me what your office skills are like…I want to see your skills dear, to see why John should keep you on the books..”

Having started to lick Sir and for him to harden, I now had him in my mouth and a hand lower down on his cock, sucking, licking and slowly stroking him.

Madam was now talking to me all the way through, encouraging me and also working on my humiliation need.

“take your time Dear, there is no rush, there is only us here in the office.”
“that’s it husband, show my boyfriend that you are the submissive in this relationship.”
“I do love watching you suck John, Dear, you are very good at it….”
“That’s it hubbie, try take a little bit more in your mouth and throat….”
“Make the most of this Ms Watson, it might be a while before you can come back to the office….

and on and on, humiliating encouragement as my Mistress Wife sat next to her boyfriend as I knelt between is legs in sexual submission.

“John, have you fucked Ms Watson over your desk?”  I almost choked when I heard that!!

“Yes I’ve done it a couple of time but usually when you’ve been away with work and I’ve decided to do a bit of late working, but not during this period, I’ve just had her come in a give me a blow job”

“you should do it a bit more often, it’s quite empowering, I’ve fucked Ms Watson a couple of time over the study desk in the last few weeks.  but perhaps not today….let her have something to look forward to the next time she comes into work…”

Madam was quite right, she had taken to putting a strap on harness and one of her dildos in the bottom drawer of her desk.  the first time that she had fucked me over the desk was after I had been licking her during a Skype meeting and once it had finished she was clearly worked up and decided that she wanted me to come out from under the desk and that she would finish herself off by fucking me.

The second time was very different.  I think that Madam had had either a bad or frustrating day and she decided that I needed to provide her stress relief.  I was called to the office told to remove my knickers and with that she unzipped her skirt and let it drop to the floor.  I had the tube of ky tossed at me and told to get ready while she put on the strap on.  I very quickly lubed my bottom as madam can put on the strap on quite quickly.  Madam did fuck me very vigorously, this was very much a dominant using a submissive.  Over the desk, legs kicked wide Madam’s hands on my shoulders and back to hold me down and her enforcing her dominance over me. (not very gentle but very much satisfying for me as a submissive – is that wrong??)

As Sir stated to get ready to cum he started to hold my head and control what I was doing more and as he did reach orgasm he held my head still and filled my mouth.  I’ve done this many times now and I know that I have to try and swallow some of it, quite quickly as there is often quite a bit of cum and semen.

Madam continued her verbal humiliation of me and it still embarrasses me to confess that it turns me on so much.  both Sir and Madam know how to push my erotic buttons (and again I ask is this wrong….?).

“You are very good at that, aren’t you Dear? barely a drop lost.  I’m really please that I can share my boyfriend with my cuckolded husband.”

“Now since you have got me all worked up I’m going to take John home and take him straight upstairs, if you can lock up here I’ll see you back at home, we’ll have dinner at 7 and wear the short maids uniform.”  and with that Madam and Sir left (he was still doing up his trousers) as I still remained on my knees and watched them head back home.

I got up and straighten up the office, when and had a look at myself in the bathroom mirror, the wig needed adjusting and then locked up.  By the time I got home I could hear that Sir was entertaining Madam upstairs so I went to get changed and get ready for the evening.

Overall a busy start to the week and as usual there has been plenty to keep me occupied…….as a quite content and happy submissive cuckold.

everyone please keep and stay safe.

billie xxx

Care and maintenance of a cuckold relationship.

Posted on by sissie billie

From Madam Alice:

Good Afternoon Everyone, hope that you are all well.

we’ve been quiet on the posting front for the last couple of weeks as we have been taking a break from the social media world.  We were all chatting and commented about how much bile has started appearing in our “vanilla” media feeds.  we all have separate accounts with different social circles and there was such a negative feel from all of them we decided to take a break from it for a short while.

The one place that does seem to be marginally sane is in the “kink” world and thank (insert deity/ mythical creature/ Mistress of your own personal choice) for that.

So what have we been upto? – well work continues with us all at different paces and we’ve been having and creating our usual fun to keep us sane while still in this lock down.  but in this post I want to write about what I’ve been doing with billie and a little about managing our relationship during this period.

When all of this current situation started we (billie and I) invited John to join us at our home.  We had no idea how long this would last but we thought that it would make things more manageable for all of us if we self isolated together.  It was billie that talked through the issues of John isolating on his own and as billie pointed out he would normally be with us for a good part of the week normally anyway.  So we had John come and stay.

In the past John has stayed with us for probably about a full 2 weeks at the longest stretch so having him here the whole time has meant that we are in new territory in our relationship as a whole and the last two weeks has shown that I have needed to adjust things.

In normal times I have the main bedroom in the house for myself and billie will sleep in the maids room downstairs.  now this isn’t some pokey little room but it is the conversion of the 3 small out buildings that were attached to the house – probably when the house was originally built in the 1900s it would have been the garden tool store, a wash room and a pantry type of store room.  The previous owners had made some effort to develop the rooms but when we bought the place Mick and I decided that we would convert them into Annex that would link into the house – the Maids rooms.

This annex has a toilet and shower, a bed area for a 3/4size bed (bigger than a single but not quite a double – it allows kerri to stay over with billie) and a wardrobe and storage area.  this connects in to the utility room of the main house.  This is Billie’s area and it is quite comfortable for her.

With John being here at home he has obviously been sharing my bed, as you would expect but it dawned on me that under normal circumstances I would on occasion let billie come and sleep with me in the main room – this would be when I wanted company, when I was lonely or when I just wanted to be with my husband and be cuddled.  It dawned on me that perhaps with John being here at home that I had been negligent in my care of my cuckolded husband.

To correct this I had billie on a couple of nights sleep next door in the guest room and after I’ve had a bit of fun with John I’ve gone and slipped in with billie for the night and when he has woken in the morning I have gone back to my own bed with John.

Also Myself and John have had billie come and sleep in the main bed with us, this has been mainly on the Saturday or Sunday nights, this has been particularly the case where we have included billie in our late night bedroom fun.  It is also nice to wake up to find that John has made use of the rear zip in Billie’s sleep suit that were made for him.  John is quite insatiable in the morning and which ever one of us is in the middle (John always sleeps on the outside) is going to be woken by his lovely cock.

Its important to ensure that billie knows he isn’t being ignore and pushed to one side, I have spoken to him to make sure that isn’t the case, which he assures me he doesn’t feel that way but it is my duty as his Mistress and wife to ensure that he knows he is loved and cared about.

The other bit of maintenance that I’ve been negligent in is the fact of billies chastity period.  we are approaching 150 days since he was allowed out for any period longer than just cleaning and shaving.  It became rather apparent when we had “no panties/knickers week” here at home.  I noticed that my dear sissy husband was leaking rather a lot.

Everytime he sat down and then got up there would be a little “puddle” of his frustrated cum on the seat and doing inspections of him would find drips or strings of cum at the end of his cage.  it dawned on me that he had not been relieved for several weeks and obviously there was now a bit of a back log for him.

In the past we used to deal with this by doing a midweek “milking session” for him using a small vibrator or prostrate massager.  billie would kneel on all fours on an ottoman blanket chest in the spare room with a plastic plate under him and I would then stimulate his prostate with the vibrator or the massager.  Carole had shown me how to do this and initially it had taken me some time to get the technique but eventually I could get this done with about 20 minutes of stimulation and then 10 minutes of “flow” to have billie relieved of his cum, but still keep that level of frustration for him.  obviously billie would end the process by consuming his leakage – we didn’t want to waste it now do we.

over the last few years we have done less of the milkings as I’ve used the strap-on more effectively on billie to relieve that pressure for him or billie has used his own dildo to deal with things.  however the most effective method has been with John becoming a more regular user of billie over the last couple of years and it always fascinates and turns me on to see the amount of cum that leaks from my sissy husband when he is used anally by John.  All of this tends to ensure that billie is regularly “emptied”, but we can still keep him frustrated, turned on and keen.

However over the last month or so he hasn’t been used much anally – yes we have had him sit on his chair with the dildo and he has been wearing his plug daily but he hasn’t been allowed to use his “Master” dildo.  Also when I spoke to John to ask if he has used billie anally he said no he hadn’t as he thought I had.  So the result was we had a very frustrated and drippy sissy husband.

Well we had to deal with this so it was time to milk my husband.  Billie was informed that I would deal with his leaking problem. He was told to get the milking tools – small vibrator, prostate massager, lube, plate and some towels and to be in position in the spare room at 8pm.

Just after 8pm myself and John entered the spare room and found billie kneeling on the top of the ottoman at the end of the bed with his plate positioned under his caged clit.  he had stripped down to his underwear of bra, waist clincher, and stockings, knickers were removed and folded neatly on the bed.  I decided that I would dress for the process with my knee high boots, bra, deep suspender belt stockings and carrying a pair of my rubber gloves.

I had asked John just wear his dressing gown as I wanted him to see the whole process and also to help me a little bit later.

Billie watched us come in and I told him to face his front.  I put on my gloves and then started to adjust the lay out of the items so that they were all to hand.  as I was doing this I was chatting to John explaining what I was about to do and what the reason for it was, all very matter of fact and almost ignoring billie at this point.  I used the lube to lubricate my gloved fingers and to apply some lube to Billie’s bottom.  I slowly worked a finger in and out of billies hole and eventually had a couple of fingers sliding in and out, nothing too much or too fast just steady and gentle.

I explained to John that this was not a quick process and that it requires the steady build up of stimulation to the prostate, without giving the sexual stimulation to the locked clit.  I also explained that this was not about deep penetration, but more about a focused point.

Once I was happy that things were lubricated properly I then switched to using the prostate massager, initially without the vibrations on, and then I turned on the low settings and allowed this to start doing it’s job, I slowly pushed and released the pressure on the massager as it buzzed away in Billie’s bottom.  I chatted with John and then switched focus to billie with things such as “good gurl” and updates  as he started to have drips form or a dangling string of cum starting to hang from the end of the cage.

I would then increase the level of vibration.  all the time telling billie what a good gurl he was, telling him how we need to do this more often for him, to allow him to be more focused as my cuckold.

As things start to increase and there are more drips and the I can tell that we are near the point where the semen will start to flow, I swap over to the smooth vibrator, this is 5″ long and quite smooth – a very traditional type of vibrator but ideal for this job.  I slide it partially in and angled it so that it makes contact with the prostrate and turn on the vibrator. this becomes very focused and you can see that there is more cum starting to drip very regularly, we are very nearly there now.

At this point I ask John to help me, to get Billie’s attention focused else where, the little tart is breathing quite heavy and it is clear that he/she becoming quite distracted by the vibrations.  

John shirked off his dressing gown and moved round to the end of the ottoman where Billie’s head was and while he stroked his cock he told billie to start to suck it.

I have a confession to make here, the sight of my frustrated husband being milked by me and taking John’s cock in his mouth almost pushed me over the edge.  with Billie’s head bobbing up and down on John’s cock I had to focus my own attention on making sure that I kept the pressure on the job in hand.

With the vibrator I kept slowly increasing the level of vibration and then it started.  the cum started to flow from billie, no spurts, just the drips forming a string, the string becoming a dribble and then it becoming a flow – lovely.

This is not the point to stop, I don’t increase the vibration but I keep the pressure on, I keep talking to billie as he sucks on John, I keep updating him on his progress and I keep watching for when the flow start to slow.

It takes time and as it starts to slow and then becomes a slow dribble and then drips and drops at that point I know that we have got him empty.  there is quite a puddle on Billie’s plate.  I keep the vibrator on the prostrate for a little longer just to make sure that s/he is empty, and then we are done.  I remove the vibrator and the rubber glove.

I take the plate and tell billie to stop sucking John and offer the plate for him to lick clean.  billie know what to do and we both watch as he laps up his emissions.  Once the plate is clean I put a finger under billie’s chin, lift it up so that he looks at me and simply say “Good Gurl, thats you done now dear.”

I tell billie to clean up and put things away and then to come and join John and I in the main bedroom, I also tell him not to bother dressing just to stay as he is.

As I said this whole activity had me all worked up and with John fluffed by billie I practically dragged John to my room so that I could make full use of what billie had prepared for me.  By the time that billie came back John and I were in full sex and billie moved to go and sit on his chair, I told billie to come and join us on the bed and to get under me with his head at my crotch.

That’s the benefit of milking your sissy husband, they are still very horny and once s/he was under me and in position he put his tongue to good use on me and with John.

John brought me to a wonderful set of orgasms – ably assisted by billie, and as he himself came in me and then slowly withdrew and I heard him tell billie to clean him.  Once he was happy with the work by billie I felt billie’s tongue being applied back to me and what was now leaking from me.  billie did his usual high standard of work ensuring that I was tidied up and consuming as much of John’s cum as possible.  I’m a very lucky Girl to have these two boys in my life and in my bed.

Once we had all calmed down I had billie come and join me and John on the pillows and we had a lovely kissing session, with John even joining in.  We kept billie in bed with us for the rest of that night with us all “spooning” together with billie in the middle.

Since that night we’ve had billie join us in the bed a couple of times and both John and I have scratched billie’s “itch” with either the cock or the strap on.  I intend to Milk billie again later this week and try and do it on a more regular 2-3 week basis.

I need billie to be my submissive sissy cuckold but more importantly I want him and need him to know that he is still my husband and loved very much by me, and I must provide him with the special intimacy that lets him know how special he is to me, whether that is done with me and billie on our own or with John involved.

Remembering back to what Carole told me in the early days, it’s not about the Dominant, its all about looking after the submissive – how right she was, I just needed to be reminded of that and how important it is to carry out the care and maintenance of my husband.  

A Weekend in the sun at home.

Posted on by sissie billie

From Madam Alice.

Good Afternoon everyone, we hope that you are all well.

We’ve had a week away from our main social media outlets, The only exception has been with our work related social media requirements.

John has had to keep his Company’s “Social media” presence updated as it seems to be the process where a lot of his clients engage with him and his company so keeping a “current profile” is an important aspect of the business.

On my side our company uses Twitter a lot and each of the departments is expected to submit articles regularly and it was my turn last week to look after doing a few posts.  Dull but necessary.

billie has had a more different week and to be honest it has been more of a “Mick” week.  the early part of the week had him doing some Tutoring on line to a couple of people who are working towards a Project Management Qualification but due to lock down they have been cut off from their face to face tutor, so Mick/ billie was asked if he could step in and help, he created the presentations and then delivered the teaching.  It was odd looking at him in his chinos, shirt and jacket at home, rather than skirt and blouse.  Should I look to get him a nice tweed 2 piece suit of jacket and skirt?  we always used to keep and eye out for a good 2 piece woman’s suit in the charity shops for him but getting the right size has always been the problem.

The second part of the week has had Mick doing a bit of personal research on line.

Mick is estranged from his immediate family, but he did have a really good relationship with his Grandfather and was fortunate enough to have met and spent time with his Great Grand Father when he was a child.  As such he has a real fascination with their War Time service (WW2 and WW1) respectively, so with the National Archive having being opened up on line, we have seen Mick digging into some family research.  John has been fascinated with the research that Mick has done so far and it may have triggered some interest in him looking into his family background.

So for all of you guys looking for the thrill of a cuckolding relationship, this is the run of the mill vanilla stuff that happens for the bulk of the time! Sorry to disappoint we’re not at it 24/7!

With the weather being so nice over the weekend, John decided that he would do the cooking on Friday evening and we sat out the back patio and ate together, with billie dressed back in skirt and blouse.

Saturday had John back at the cooking but with a BBQ and I managed to do a bit of a lounge in the sun, while I started with a swimsuit, but ended up fully naked as the afternoon progressed.  billie was pottering around looking after the garden and doing some planting, He had dressed himself in a short skirt and a sleeveless blouse with a set of trainers.   Watching him work on the flower beds and planting things, bending over and kneeling down flashing the tops of his tan stockings was quite a delight to behold for me.

Once he finished his work on the flower beds and the grass was cut he went and cleaned up and came back with a set of heels on.  By the time we went inside at a 7pm we were all rather “cheery” as we had shared a couple of  bottles of wine.  I think that John took advantage of both of our slightly merry state and we all ended up in a state of undress, with me naked and billie just in suspender belt, stockings and heels.

It was quite a pleasant evening for all concerned.

So today has been a slow start for me, hence why I’m blogging, Mick is back in his virtual classroom with his students and John has gone out to his office to collect work to drop off at the homes of some of his staff.

Mick looks rather smart and tidy this morning in jacket and slacks but he does have a nice matching three piece set of lingerie underneath of Bra, Suspender Belt and knickers in black with some lace top stockings.  and it is so reassuring knowing that he is caged and butt plugged as well.  I wonder what his students would make of that if they knew….

well I’ll finish here and go and have a cup of coffee and get prepared for my online meeting at 3.30pm.

Everyone please take care and I’ll see if I can get billie to do a blog post later in the week.

Kind Regards

Madam Alice.