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Category: strap-on

A week of preperations

Posted on 10/06/2020 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

Getting the most out of Power Dressing

Posted on 05/05/2020 by sissie billie

From Madam Alice

hello, hope you are all well. we are all in good health here.  life has continued with our self isolating and working from home.

Mick has continued to do some online/ distance tutoring for his couple of students, this is mainly Mondays and Tuesdays for them and he has continued with some of his research but that was mainly on Wednesday.  he normally gets back into billie mode very quickly after finishing.

John has been continuing with his company’s work and that seems to be working quite well, a few of his team have had to have new computers and software to deal with some of the work but overall he seems quite happy with the way his staff are working and dealing with things.

I am being Skyped/ MS Team/ Zoomed to death! some of it is bloody painful, so much so that out department head has stepped in to save us – we definitely have some people working from home that are bored/ lonely/ want to annoy someone and therefore decide to schedule a meeting and then invite everyone.  Hopefully now that we have clear direction a lot of that crap will stop.

As it was Thursday saw me having to dress up a little – a couple of finance briefs to senior management on camera so it was on with my suit.  I decided to put my own twist on it.

I had billie get my grey trouser suit out and pressed.  I then put my hair up in a bun (which is growing more than I expected.)  I then added my quarter cup bra, waspie and black stockings.  Added to the outfit I decided on my 5″ heels with the 1″ platform.  The final part and the twist was I decided to wear one of my strap-ons.  No panties or knickers I was going Commando!

billie brought my suit in as I was finishing my dressing and adding my “cock”.  I told billie to put my suit on the bed and to get down and give me a little bit of a BJ.   while she worked her mouth on the dildo I told her that once I was dressed and off to the study she was to go and change into her secretary outfit with her pencil skirt and she was to be in Ms Watson mode for the day.

As she bobbed her head up and down my strap-on I gave her instructions for the day.  I would want tea in the study at 9.30am, with a light lunch at 12.00 noon in the dining room.  she should work from her table in the utility room and be on call if I need her.  John would want her to help him later in the afternoon when he goes to the office to deal with Mail and Orders.

After a short while and billie had got into her stride I took hold of her head and started to thrust at her effectively face-fucking her – I’m very careful with this as the issue is that a strap-on isn’t the same as a cock so it’s important not to get carried away with things.  either way billie did very well and when I was content I stopped and told her to go and change while I finished dressing.

Cream satin blouse, dark grey trousers, I dress to the left by the way and then topped off with the Jacket, heels back on and then off down to the study and to log on.

It’s quite strange really, here I was in my study in a woman’s suit, very much the power suit for the office bitch, and I kept finding myself playing with my “cock” through my trousers.  It was quite a strange experience once you realise that you are doing it.

billie appeared with my tea and 2 biscuits at 9.30 on the dot.  I carried out a quick inspection and yes slightly damp panties and a plugged bottom – lovely.  I told her that my first meeting was at 10am and she should be back here at 9.50.

9.50 saw billie reappear, thinking that she was here to take my empty cup and plate away but no I had other plans.

I told her to crawl under my desk and get my cock out.  I had placed a cushion on the floor for her – I’m kind like that, but also I didn’t know how long the meeting would take.

My instructions were simple.  take the cock in her mouth like a good slut secretary and make sure her mouth does not come off of it until I tell her to do so at the end of my meeting.  she was to keep the noise to a minimum as she wouldn’t know when I would be on mic.

she should start licking the cock and when the meeting starts she would then start her blowjob.

well my darling sissy secretary spent 47 minutes on her knees with my cock in her mouth.  There was a couple of times during the meeting where I reached under and placed my hand on the back of her head and forced her down slowly onto the cock and held her there for a few seconds.  on one of theses she gagged – I held her a little too long perhaps, I let her up for air and she quickly went back onto the dildo.  while she didn’t know it I had muted the microphone each time.

At the end of the meeting I allowed billie to get out from the desk and told her that since she had made some noise, that she should be punished.  I had her bend over the desk and pull her skirt up and I took my paddle from my desk drawer and gave her 4 not so gentle smacks.  I told her to get up, leave her knickers with me and to get on with her tasks.  I told her the next meeting would be at 2pm, she should be back in position for 1.50pm ready to go again.  With that I dismissed her back to work.

The afternoon meeting was a bit shorter at 35 minutes but billie was a lot better with less noise but plenty of enthusiasm.

It would appear that this was a bit of practice for her as John had her provide the same service while he spoke to a supplier on the phone when the two of them went to his offices.

I enjoyed my Power dressing and having my cock in my trousers.  I think I’ll repeat this again but I may just have to have a go at fucking my secretary in the office this week, she’s certainly a tart that would be up for it!

everyone please take care, keep safe and stay healthy

King Regards

Madam Alice

Update on Chastity and a wet weekend

Posted on 20/08/2019 by sissie billie

This will be the first of a couple of blog posts today – so long and I don’t get distracted.

Normally this week we are all on holiday in some form but as I mentioned a couple of posts back we’ve had to change our plans due to the hotel that was booked having some of the rooms damaged.  Moneys have been refunded and the offer of discounts for rebooking later in the year have been accepted.

Normally what happens is that Madam and Sir head off for a few days on their own and I am sent to Mistress Carol’s for an “Annual Assessment” to ensure that I’m being a good submissive for Madam and to spend the time as a maid to Mistress Carol, I also get to have time with Kerri.  that is normally for 4 days and then we all meet up – Madam and Sir, Mistress Carol and her Partner (B/F) and Kerri and Myself – for the 4 days of the bank holiday.

Mistress Carol – I will be in so much trouble for this – again!

But that is to be delayed and it looks like it will be some time in November when we have a get together.

So what has that to do with my Chastity and my confinement period?

This weekend was an interesting situation.  On Thursday night Madam tasked me to make sure that all shopping was to be done on Friday (my normal routine) and told me that She and Sir would not be going out on Saturday evening so I was to prepare for a small BBQ for them or if the weather wasn’t good a small grill and buffet.  I was required to be back from my shopping trip no later that 11.00am.

Once back I was to get my self ready and be in my maids uniform from 12 noon onwards – but I was not to wear any panties and I was to have my main butt plug fitted.  I was later to find that I wouldn’t be allow to wear panties for the whole weekend.

Friday after lunch was spent making sure the rooms were tidy and ready for Madam and Sir, the washing was done (but not put on the line as the weather was dreadful, so the utility room with it’s two clothes dryers/ airers was in full use (we don’t use the tumble drier unless in an absolute emergency).  All the Ironing was done and new scent liners put in the drawers of Madam’s dresser and wardrobe.

Madam came home about 4pm, earlier that usual and we had a sit and a chat.  her plan for the weekend was to be a rather frustrating spectacle for me.  I would be in sissy maid role for the whole weekend, I would not be allowed to wear any knickers or panties until Monday morning.  Added to which Madam informed me that she would be having a Lingerie weekend, she would only be wearing stockings and lingerie, and she would be joining me in wearing no panties until Monday morning.

Madam them informed me that once Sir arrived he would go for a shower/ bath and I was to take his clothes for washing and Ironing ready for when he would leave on either Sunday Night or Monday morning.  It was intended that he would be naked for the duration of his visit or at most wearing his bath robe.

“I want my sissy husband to have a weekend surrounded by the things that frustrate him”

I was made to stand and Madam lifted my short maid skirt and she felt my cage, her smile said it all, “You’re a bit wet dear.  And we haven’t even started to tease you yet!”

She checked that I was plugged and whispered in my ear “I love having you this horny and frustrated, I want you really dripping by the end of this weekend!  This extension in your chastity really has brought you on with your submission and willingness to be my slut!”

It did shock me a little when she said it but she was right.  Since we went on our Holiday to Scotland, Madam has used the strap-on on me more regularly, I’ve responded to it more.

It has also be more clear to me that Madam has been enormously turned on by my frustrations and my response to being (Want? needing?) to be fucked by her and also by my willingness to be fucked by Sir.  I would say that previously it has been an act of submission – beta male to the Alpha Male – and enjoyable act of submission but an act of submission none the less, where the caged frustration makes it something slightly different, I willingly want to be fucked to release/ ease the frustration.

Then Madam gave the knock out “I’m going to keep you caged until after the trip away in November, with the possibility of running it through to Christmas, It depends how much I enjoy your frustrations….You have two ways of looking at that!”  With that bombshell Madam Slapped my arse cheek “Right you little drippy tart, go run my bath and lay out my Black Basque, seamed stockings, and 5″ heels, Oh and add the black elbow gloves.  Remember no knickers, I want John to have full access to everything this weekend and that goes for you as well my lovely husband!!”

and with that I was dismissed to start the bath.

Yes the weekend was a frustrating weekend, Yes I was regularly checked for how wet and drippy I was – often my skirt didn’t need to be lifted!  Both Sir and Madam made full use of the unrestricted access and while I’m not proud to say there was times I was almost behaving like a complete slut – but I couldn’t say anything about it at the time – read into that what you will!

So it is not Tuesday morning, we are clearing the last of the weekend washing – bed clothes yesterday and Madam’s Lingerie this morning and my uniform and lingerie this afternoon.  I’m back in knickers but It looks like it will be regular changes of those each day from now until Christmas (????) due to my caged frustrations.

I’ll keep you all updated on how my caged progress goes on over the coming weeks and months.

billie xxx

Still not unlocked

Posted on 01/08/2019 by sissie billie

We arrived back from our holiday on Saturday evening, after a week of pretty good weather we travelled back through showers, so we picked the week just right for the best of the weather.

We haven’t been to Scotland for about 10 years and it was great to have been back. I spent quite a bit of time dressed in female clothing, not always fully Fem but the bulk of the clothing was female.

the other thing was that I wasn’t unlocked.  Madam had brought one of her Strap-ons with her and she used it quite a lot on me.  I’m approaching 100 days in chastity and I have been leaking a lot when I’m being fucked by Madam.

There was also several occasions when Madam was quite dominant and aggressive in her sex with me.  Yes there was a lot of leakage on those occasions, Luckily I packed plenty of panties and knickers to deal with all my leaking and dripping over the week.

so we are back and we had been looking forward to our usual get together at the August Bank Holiday but things may be changing with that – Madam, Sir and Mistress Carol and her Partner normally meet up for the weekend after I’ve spent a few days with Mistress Carol and Kerri.  however there appear to be a booking problem with the hotel so we are waiting to see what happens there.

So at the moment I need to get on with my jobs, I need to make sure that the washing is done and we are all ready for the weekend, I’ll also work out what needs to go on my shopping list for tomorrow.  the work of Madam’s maid doesn’t end, no matter how drippy and damp her sissy knickers get!

billie xxx

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