Category: cuckold

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!

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.

Valentines Day at Home

Posted on by sissie billie

 Normally I don’t get to have valentine’s evening with Madam, normally that occasion is an event on Sir’s calendar.  It’s one of the dates in the year that he has specified as being one of his.

The lock down period sort of changed that a little bit, where we ended up with the 3 of us having valentines evening together – which was very nice and fun.

But this year, with it being on a Tuesday it didn’t land neatly to fit into the schedules.  So Sir laid on a romantic evening over at his house on Saturday night for Madam.  With everyone having been out with Mistress Carol and kerri for a meal the previous weekend it was felt that it would be too much to have another night out so soon.

The result was that Sir came over on Friday evening and had the night here, I was in my cuckold maid role for the evening and served both Madam and Sir before being dismissed from Madam’s room at about midnight.

Saturday afternoon Sir went home to prepare everything for the evening at his house, and to get the cooking done – he is quite a good cook- and I was given orders to deliver my wife to his home at 7pm, which was duly complied with at the allotted time.

From all accounts they had a lovely evening.

I used some of my free time on Saturday to have a call and chat with Kerri to see how she was doing and also how Mistress Carol was getting on. Both are in better form and kerri has now had a firm job offer so will be starting that in Early April.  That change has made her sound a lot better and happier.

On the Sunday the plan was to go and visit a Garden centre as I wanted to get some daffodils plants and bulbs for the front garden to replace the ones that I think one of the squirrels has taken – Yes I know, just how Rock and Roll do you want.  Sir and Madam met me at the garden Centre and we had lunch together – It’s not all kink you know, there is some vanilla stuff in our life.  

There are times when I sit in places like that and look round at everyone else and wonder who else in here is in chastity? who else amongst the men is wearing wearing stockings and lingerie under their street clothes?  Next time you are out and you have a moment, just have a look around and give it a thought?

The rest of Sunday was spent at home, I was back in Maid mode looking after Madam and Sir for the afternoon and evening.  Sir went home about 9pm that night.

Madam spoke to me once Sir had gone and let me know that her plan was to have valentines night with me and that I should prepare something for us to have at home.  So I put some thought to it.

On Tuesday morning I was up and made Madam’s breakfast for her and took the card I had for her and placed it on the tray along with the small present that I had got her.   (we tend not to give big or fancy gifts at valentines, it tends to be something like a pair of knickers or stockings – there has been the occasional exception in the past where I have got Madam some matching lingerie as she was going away for a weekend and I wanted her to feel special.)  On this occasion I had got her a pair of lace top stockings.

(Just so you are aware I had also sent a valentine’s card and a present of some black satin knickers to kerri.)

  Madam was very pleased with her card and gift and gave me a card and a small packet.  My valentine’s card was a “Happy Valentine’s day to my Wonderful Wife” and was addressed to billie.  My present was also a pair of stockings.  Madam told me to join her in the bed (just kick off your heels) and to cuddle in next to her. while she had her tea and toast.

Madam explained that for this evening she wanted me to be in blouse and skirt when she got home and to have my Pink PJs up in her room for later.

Once Madam went to work I cracked on with making the bed and getting the bathroom squared away, nothing too drastic as I had done a full clean the previous day.  The rest of the day was with me working from the office dealing with a project for a rather difficult client (and I’m being kind to the client as they are particularly difficult!).

The evening meal would be a small buffet of party finger food (we had a number of packs of things in the freezer from when we were expecting more people for Christmas and new year, I also had some profiteroles defrosting as I know that Madam is particularly fond of them).  With a bottle of wine in the fridge chilling things were all set.

Madam arrived home at her usual time and I had her bath ready for her, while she had a soak I laid out our evening buffet ready for when she was finished.  I could hear her upstairs getting dressed  as I laid out the last of the food and went and opened the bottle of wine for her.  I poured her a glass when I heard her start to come down the stairs and I waited with the glass on a small tray for her to come into the living room.

when she entered the living room, I bobbed a short curtsy and said “happy valentine’s Madam” and offered her the glass.  I got a look from her and thought that I had messed up and then she smiled at me, “It’s a night off for the maid, go get a glass and join your wife, Dear.”

I came back with a glass and Alice poured me a glass of wine and gave me a full and very passionate kiss and then asked “will you be my Valentine?”

the simple answer from me was “Always!”. With that we kissed again.  

It may well be the extended periods in chastity, or may be just an age thing (I’m not a pup any more -haven’t been for a long time!) but it is moments of intimacy that really do get me turned on, I really enjoy and get a lot from kissing, hugging and cuddling my wonderful wife.  That does not detract from being fully sexually intimate with her, in all forms, but I am now more aware of the parts of the relationship that feed my emotional needs.

For the next hour and a bit we basically grazed on the food, chatted and cuddled with each other.  once we finished eating we were more like a pair of frustrated first daters, there was lots of roving hands, going underskirts and rubbing fronts of knickers while we were lying on the couch necking with each other.  Looking back at it now, after a few days of reflection, it felt like the time we were almost caught by Alice’s mother making out on her couch when I was courting her many years ago!

I clearly had got my Madam a bit worked up as she called a halt to the activities and ordered me to ‘get my arse up to her room’ and get dressed ready for her.  I scuttled off in my heels to the bedroom and quickly removed my blouse, skirt and stockings.  I had preempted things by having my pink bra, suspenders and knickers on, so it was a case of just putting on the pink stockings, satin french knickers and cami and then putting on the satin PJs over the top.  I finished it off by adding my red heels.  I was making a fair assumption that we were not going to be going to sleep just yet.

photo taken on Thursday evening for another photo session

Alice came into the room having already taken her blouse and skirt off down in the living room and was in a black bra, knickers, suspenders and stockings. As she came into the room she undid her bra and went to her drawers and got a satin chemise and put that on, with it coming to mid thigh.

The two of us were now very much dressed in slippery satin, Alice in black and me in pink. We got onto the bed and continued on from where we had been down stairs, just with more room.  The risk of falling off on to the floor was significantly less on the double bed than it had been when we were on the couch.

I don’t know if it was by habit or if by gentle direction but once Alice was starting to get worked up with all of our kissing and roving hands, I found my self moving down her body.  I could see her nipples pushing against the satin so I started to lick then through the material.  As I kissed and licked one, I would gently brush the material over the other with one of my hands.  Feeling them get hard, taking my time on them.  There was no rushing this evening, plenty of time to make sure that my wife was slowly building up her arousal.

I slowly worked my way down to between her legs and slowly rubbed the satin that was covering her legs and stockings.  Regular readers will know that stockings are my kryptonite, so feeling them and rubbing my wife’s nylon covered legs was making my tight caged confinement even tighter and more uncomfortable – but in a really good way.  (last statement will seem really odd, unless you have spent an extended period in chastity and or get turned on by being teased and confined, it’s difficult to explain but having chatted with other chastity wearers they have similar feelings – Yes seems odd but it just works, trust me on this!) 

From stroking her legs I pushed the chemise up and then started to kiss the tops of her stockings and her thighs, while doing this I eased her panties down so that I could then kiss and lick my way up to her lovely sex.  I love giving Alice, my Mistress and wife, oral pleasure, to slowly work my tongue around her pussy is divine and to work her towards an orgasm is a fantastic feeling, especially as you listen to the changes in her breathing, the changes in her body and if she has her hands on my head to feel the pressure applied and released and then reapplied to push my face into her pussy, absolutely delightful! To worship her and bring her to orgasm…well I’m a very lucky submissive.

Madam released me from her thighs once she had calmed down, I move up to cuddle her and to hold her as she got her breath back. 

She told me to take my PJ bottoms and the knickers off and to get her strap on.  I duly complied.  I was told to come back onto the bed and to lie on my side facing the wardrobe with the Mirrors on the door.  Madam adjusted the Strap on and once she was happy she applied some lube to my sissy hole and also to the shaft of the strap on.

what was under the PJ jacket and trousers

I was told to get comfortable and adjust the pillows, Madam did the same and then wriggled in behind me and eased the dildo into me.  Everything was very slow and comfortable, nice and gentle.  Once she was fully in me she started to kiss my neck and rub her hand over my stocking covered legs and the satin of the PJ jacket.

I was told to keep watching the mirror, as she very gently fucked me. She had one hand free to wander across me and the other supported her. The one place that her hand never went was anywhere near my caged clit. 

All through this Alice was whispering into my ear, telling me how much she loved me, how special I was.  She made it clear that if I started to feel that I was going to cum (dripping was fine but no assgasm!) then I must tell her.  Twice during the evening I almost reached an orgasm as she fucked me and whispered love  and dirty talk into my ear.  This was one of the most erotic and frustrating edging sessions I’ve ever endured, but I would do it again! (I haven’t been milked or allowed to use my dildos for nearly 6 weeks now so this fucking/ love making was very frustrating – I’m normally milked every 2 weeks if I haven’t cum from being fucked). Each time I told her that I was about to cum, she would slow to a stop, focus on kissing me, bite my ear, rub my legs, enough to keep me aroused but enough to allow the feelings inside to subside and then she would start again very slowly. 

The pace was very pedestrian, and we were coupled like that for just over an hour.  The thing that made us stop was actually that Alice’s other arm was starting to go dead and becoming uncomfortable 😆😆. Alice withdrew from me and I rolled onto my back while she straddled me and I watched her trying not to chuckle as she worked feeling back into her arm!  I sat up and held her close and kissed her.  

That had been a very special valentine’s fucking.  While I was incredibly frustrated it was totally fantastic, I’m not sure how to better explain it.

We kissed and cuddled for a bit and then I helped to take the strap on off her and we got into the bed and spent the night cuddled together.

In the morning I woke at my usual time and went to sneak out of the bed so that I could get dressed and prepare Madam’s breakfast.  Alice caught my hand and told me – her husband – to get back into the bed and keep her warm until her alarm went off, it would appear that the maid was getting a late start.  When the alarm went off we were both up and Alice told me to join her in the shower.  As much as we would have loved to have spent longer in the shower together, Alice had to go to work so when she got out the shower I quickly dried myself, wrapped a towel around myself and went down to the kitchen to make some coffee for her and put it in a travel mug for her to drink on the way to work.

I met her at the bottom of the stairs, with just the towel on and handed her the mug.  she put on her jacket and then gave me a very passionate french kiss. Just as she went to leave she pulled at my towel, pulling it off me and stepped out the door.  Her leaving comment as I stood naked in the door  was “Make sure to stay there to wave me off Dear!” She then through the towel out onto the grass on the other side of her car.  

So I stood naked at the open door of our house waving Madam off to work, as she drove out passed the gate and as she waited to turn into the road as a couple of cars came passed.  I kept waving until she pulled into the road and disappeared down the lane.  I have no idea if any of the passing cars saw a naked bloke waving his wife off to work that morning or a naked person wandering out in the front garden to collect a discarded bath towel!

I worship my Madam Alice

I started this post by saying that I don’t normally have valentine’s day/ evening with Alice or Madam, well I’ll be honest this valentine’s day made up for it. I think I spent the rest of the day with quite a spring in my step.

billie 💋💋💋   

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.  

Getting what you ask for

Posted on by sissie billie

We hope everyone is well, we are all fine here at Madam’s residence.

we’ve all had a busy week with working from home, which has been good as it has stopped everyone from being bored.  the only thing I would say is that all 3 of us are getting Skype fatigue.  it is quite clear in this period of social distancing some people when given their turn in an online conference just don’t know when to shut the fuck up!!!  It is interesting as all three of us have encountered this and we are working in different sectors.

But that isn’t what you have come to this blog for, is it?

Last weekend saw the continuation of resetting boundaries and tasks with a humiliation and emasculation theme.  On Saturday I had to go to our attic and get on of the old wooden chairs that we had up there, clean it up and place it in Madam’s bedroom.  I was then told to get on of my dildo’s with a suction base and place it on the chair.  Since that point in time, when ever I am required to be present when Sir and Madam have sex I am directed to remove my butt plug and sit on the dildo and the chair.  I will be told to either sit fully down on the chair and watch quietly or I will be told that I may fuck myself on the dildo until told to stop.

On Tuesday afternoon Madam called me to her study and told me that she would be finishing shortly and that she wanted me to go to her room and lay out some of her more slutty items of underwear and to then wait for her.

she arrived a little while later and told me to get her douche and soaps as she planned to give her back passage a good cleaning.  I helped Madam undress and head to the en-suite and use the douche enough times to make sure that she was fully clean back there.  once she was happy she had a shower and I waited to help dry her off.

I helped to dry her and I was told to kneel and Madam handed me a tube of KY and I was told to lubricate her arse which I did being very gentle, not wishing to incur her wrath.  she then handed me one of her butt plugs and told me to gently insert it into her.  I coated it in lube and then eased it into to her.  She let out a slight gasp as it forced her hole open and then closed around the neck of the plug.

I was then told to get up and to remove my maids uniform  and to go to the bed.  Madam made me lie on the bed, head towards the bottom and my feet at the headboard.  and she then took some lengths of bondage rope and tied me spread eagle to the bed.  she then took a ball gag and fitted that to my mouth.  I was securely displayed in my Girdle, Stockings, knickers and bra.

Madam sat down at her dresser and applied her makeup, which was most definitely darker than usual –  she applied purple nail polish to her fingers and toes and a black lipstick.  she applied some wet gel to her hair to make it slick and pulled it back.  the black eyeshadow and thick eye liner gave her a very dark dominant goth type of look.

I watched her get dressed – Underbust black corset, 6 suspender straps holding up dark black seamed stockings and then a pair of backless PVC panties.  Madam then added her patent black knee high boots and a thin leather collar.

She came and sat on the bed next to me, “Do you like what you see, hubbie?”

I nodded quite enthusiastically.

She started to rub the front of my girdle that covered my caged pantied clit – “I want to be a bitch tonight, not a nice wife, but quite nasty, so I’ve put my cunt out of bounds to John and you tonight – that’s right, no pussy licking for you this evening.  I’ve not had a nice arse fucking for a while and I’ve become quite jealous that my submissive husband is getting his arse fucked more than his Mistress, so I plan to change that this evening….”

With that she went to the bed room door opened it and shouted “John! would mind popping in here for a minute?!”

From my restrained position I could see her back and the open nature of the knickers. and the stockings.

John appeared and she literally pulled him into the bedroom.

“Right then John, I need fucking and I need it now!”

From what I could see Sir look slightly taken aback and was a little stunned as Madam pulled him into the room next to the bed and then undid his trousers.  Madam when down onto her knees and took hold of Sir’s cock.  I think at this point he had got his wits together and was now taking in the scene of my wife starting to take his cock into her mouth and me tied to the bed.

there was very little that I could do other than frustratingly watch this Goth Mistress suck Sir. As she did this Sir was shedding his clothes until he was stood there naked.

With Sir fully erect, Madam stopped her oral work and stood up, keeping her hand on his 9 inches and told him that her pussy was out of bounds for the evening but he could fuck her arse as much and as often as he wanted.  Still holding his cock she then led him to the bottom of the bed where she then let go and climbed on, crawling over me until her panties were directly over me.

“My knickers stay on John,  Fuck me like your bitch, show billie what a slut he has for a wife!  billie hasn’t been in my arse for over 15 years, show him what she is missing!”

It is true, we decided that billie and mick would not have Anal with Alice, Alice would regularly fuck billie in the arse but that was out of bounds for both of my personas.

As Madam offered her ass to Sir she passed some lube back to Sir and I watched fascinated as he lubed himself up and then eased the plug out of Madam before adding more lube to her bottom.

The thing that next surprised me was that I expected some fore play, some using fingers to help open Madam up, but no, Sir when straight at it with his cock!

He had done this to me and I can confess, you bloody know about it!  well Madam certainly got what she wanted and she let out a very vocal squeal!  It looked like Sir had placed a hand on her back to stop her coming up out of position and with the other hand he positioned it and then leaned forward and pushed it in, not fast but at a steady pace.

Madam was rather vocal, I really do hope that there was no joggers passing in the lane because there is no way that noise was staying in the room!

My position meant that I had full view of Sir entering Madam until his balls obscured the view.  Once he was fully in he stopped to let Madam get used to it and to calm down and then he started to slowly fuck her.  this was not lovemaking, Madam had asked to be fucked and it very much appeared that Sir was going to fully oblige to her requests!

During their fucking Madam didn’t touch me, I was just a very close spectator, It was as they finished, Sir withdrew and I could see that he had cum.  my gag was undone and Sir placed his cock head at my mouth – “clean it!”  I complied with licking and sucking it clean and then he withdrew from my mouth.

“Sit up Alice, let billie tidy you up and get you ready for the next round.”  I don’t know what the look was on Madam’s face but I thought that he had fucked her quite thoroughly, so to think that they would go again without a rest…..

Madam sat up and positioned herself so that I could get access to her bottom.  It was still open a little and Sir’s cum was leaking out, I could see it close as I started to lick her, I was being as gentle as I could.

I’m not sure how long I worked Madam’s used bottom but Sir was back and pushed her forward, he had lubed his cock again and again without ceremony he eased his cock back into her for another round.

This time the sex was more steady and more controlled but Sir was more verbal to Madam, with things like:

“You like being my bitch don’t you!”
“You and your sissy are both sluts for my cock in your arses!”
“billie could never fill you like this could he!”
“You had best wear a plug when you are working from now on, I might just come in and fuck you over the desk is you are going to behave like a wanton slut!”

Sir gave Madam a verbal fucking as well as a physical one.

By the end of the evening Madam had been ass fucked 4 times, I was released from the bed after the end of the second fucking, but I cleaned Sir and Madam after each session.    I would say that when Sir and I put Madam to bed at 10pm she was well fuck and very tired – quite content but a little sore.

There is a moral to this and I do think that Madam did learn something from it – Be careful what you ask for – you might just get it and some more!

100 days milstone achieved

Posted on by sissie billie

Good Morning everyone, I’ve just cleared the breakfast things away and Madam has told me to put a short post up as I have now crossed what Madam says is the first milestone for this year.

I’ve now completed 100 days in chastity.

I have a suspicion that this won’t be my only milestone in this chastity session.

Today is Madam’s Dress Down Friday, so for all of us there are no pants, panties or knickers worn and Madam is currently working in her study wearing her What Katie Did Merry Widow with lace top stockings.  the only thing is that I’ve had to place a newly ironed blouse in the room on the back of a chair for when Madam has a video call which I think is planned for 9.30 this morning.

I’ve done the same for Sir with a Ironed shirt next to where he is working upstairs.

I’ll be getting changed shortly out of my working maids uniform and then off to Leighton Buzzard for the weekly shop and then back and changed out of my trousers and blouse. Madam has told me that I should pick out a Bra and girdle set for the rest of the day.

I’ll finish now and get on with things.  everyone keep safe and well and hopefully I’ll post on Monday.

billie xxx

An Update from billie

Posted on by sissie billie

Well it’s been business at usual here in our FLR, with Madam away last week I kept myself busy with my work – the exception being last Wednesday where I was at Master’s house looking after his needs and requirements on behalf of Madam.

I didn’t get home until 1am and I was rather worn out – tired and sore would be a way of putting it.  so last Thursday was a deliberately slow day for me……

Madam was home on Friday evening and as usual I had missed her and as Madam stated in her post last night I was dressed and waiting for her.  While Madam did say that she was a bit rough with me I didn’t see it that way, she was very Dominant and very specific about her needs and wants and I was more than happy to comply with her demands and instruction.

It is one of my best pleasures to bring Madam to orgasm and to do that several times last Friday was an amazing honour for me.  I was fortunate enough that once she was satisfied and I had bathed her that she told me to stay and sleep with her.  so I changed into one of my teddies and fresh stockings and cuddled in her until she fell asleep.

Sir came round on Saturday for the weekend and the main announcement was that the hotel that we would have been visiting in August was finally back open and while they had reimbursed the money for the cancelled visit they has offered a very good deal for a break, which Madam and Sir were going to accept.  So they would be going for a 4 day break at the hotel and Sir had managed to get a good package to Cape Verde for a week, so he and Madam would be getting some winter sun.

Madam called Mistress Carol to see if kerri would be free to look after me  for a week but unfortunately kerri has already been told by her work that she can get a long holiday until the new year.  The good news is however that everyone has agreed that both kerri and I will be allowed to go for a break somewhere in the new year.

We made the most of the reasonable weather on the Saturday but with the rain on Sunday, Sir and Madam spent the bulk of the day in bed with me in full submissive maid mode, serving drinks and food, cleaning Madam and Sir, being humiliated and generally being frustratingly happy to be their submissive cuckold.

On Monday I spent time in the office looking at my programme of works and seeing what I could deal with while Madam would be away.  I knew one of my clients wanted a project review carried out and another was looking for some consultancy advice for a future proposal so after a few calls these have been booked and arranged, so there will be a trip up to York and Newcastle on the cards, that will have me away for a couple of nights each so that will keep me busy while Madam is away.

We are approaching 180 days in chastity and to be honest I’m quite comfortable with the cage and my frustrations, I really do enjoy them, but that is mainly due to the fact that I am probably having more sex now that I did when uncaged.  the only difference is that I am in a different role.  I don’t penetrate, I am the one that is penetrated and serves, The emotional and sexual feelings of being submissive to Madam is difficult to describe, but I know one thing that I wouldn’t swap it for the world.

Keeping fit and active

Posted on by sissie billie

I’m not a spring chicken, by any stretch of the imagination.  I’m in my fifties and I’ve put my body and mind through some mills in my time.  so to manage that I do some steady exercise.  generally it is a run – well more a steady plod, twice a week, and also one or two local walks as well.

I don’t lift weights but I do a set of floor exercises and stretches most days.  these are often squats, sit ups and I use a set of resistance bands for curls and leg works.  I’m not setting the world on fire but it is good steady stuff and more that what I used to do during my busy working life.

Madam insists that my training and exercises are done while wearing female attire.  The common one has been opaque tights, a body shaper and then a long sleeved body suit.  when jogging I must wear some type of female shapewear, normally a panty girdle and during winter opaque tights.

Madam also likes to me to have exercises that would normally be female “bums and tum” type exercises as well, often having to do these while wearing heels.  and these routines are regularly mixed in with my exercise routines.

There has been times over the winter when Madam requires me to go for my jogs in panty girdle, opaque tights and long line bra with my home made bra infills (knee high stockings filled with set weights of rice) under my jogging suit, it does make you appreciate a good quality bra…but Madam is clear that I won’t have a sports bra for these type of tasks.

Madam likes the idea of me doing more female type exercises and also to introduce more sissy exercises so she was really interested when we cam across this work out routine by a sissy called Eve on twitter.  Madam tasked me to contact Eve to get her permission to publish her work out on the blog and also to get me to incorporate it into my routine.

so here it is – Eve’s Sissy Workout

(if the video’s don’t work use the links at the bottom of the page)

#Sissyworkout pt1 I have started writing a sissy workout to help my fellow sluts build a body for others pleasure. It aims to work your boi-pussy, firm up your ass and ensure you are in the right state of mind. #sissy #slut #whore #anal #practice #chastity


#sissyworkout pt2: it’s very important you do this workout fully made up like a perfect sissy slut. At the very least in heels and chastity. #sissy #slut #whore #chastity


#sissyworkout pt 3: 20 donkey kicks each leg while holding a dildo in your boi-pussy. If you drop it start over.  #sissy #chastity #slut #anal #analtraining #whore

#sissyworkout pt 4: 20 x plug pickups, squat onto the plug, it’s important to guide it in by feel don’t use your hands. Then squeeze your cunt and pick it up. Make sure to put back down slowly and gently. Increase difficulty by placing the plug lower and getting a straighter plug

#sissyworkout pt5: 1min slut pluses, place good size dildo on a chair and slowly bounce on it. It’s important not to let you ass touch the chair. If you get too tired you can rest with the dildo all the way in but you should wiggle your ass side to side then resume bouncing.
#sissyworkout pt 6: 2 minutes impaled chair. Get the largest dildo you own. It should be long and far over your comfortable limit. Place it on a chair and squat with just the first inch inside you. Now hold, arms above you head and wait. If you can’t hold your weight TOUGH SHIT. Added note, you should do this at the end of you workout when your legs are tired. If you don’t have you full weight on that cock by the end you need to work harder before or increase the time.

Eve’s twitter page is at this link – https://twitter.com/sub_her and the direct links to each of the work out posts are here: Sissy Work Out 1 Sissy Work Out 2 Sissy Work Out 3 Sissy Work Out 4 Sissy Work Out 5 Sissy Work Out 6 Eve has a great Twitter feed and if you use it feel free to go and have a look at what she is upto and let her know what you think of her work out and perhaps encourage her to create some more exercises.

Eve – @sub_her

Eve – Little Bitch @sub_her