Author: sissie billie

I’ve been wearing chastity devices for about 15 years now, and the last few years have seen longer and longer periods of wear.  linked with that has been the fact that I spend the majority of time in women’s lingerie.

So when you combine the two activities there are a few things that you learn.

Now things to note, my clit is not cut – I’m not circumcised, and my foreskin does not fully retract back behind the head of my clit so it is not uncommon for my foreskin to poke out of the end of the smaller chastity cages that I wear.

So what?

well this creates a bit of a dilemma – I like lingerie and it turns me on, I like wearing Lingerie and that turns me on.  There is a wide range of female knickers and panties that looks great and feels great but if you wear chastity you need to take care.  make sure that you choose the right knickers to suite your chastity!

For me Lace fronted knickers look fantastic and on Madam they are sexy as hell, but when I wear them they are murder – why?  because as my foreskin pokes out and once I start moving it can ,if the lace is particularly stiff, be like taking a cheese grater to my foreskin!!! not nice!

If you are going to wear lace fronted knickers probably best use a fully closed cage like the CB6000 type.

Next is nylon knickers with patterns on them – very similar to the lace ones, depending on the type of pattern.  they often feel like areas are raised or thicker where the pattern is and if that’s at the wrong place – well can still be a bit rough on your little caged bits.

Currently I’m locked in an open metal cage so I try to go for nylon panties with a tight weave (smooth finish), silks or satins.  these can be quite thin material and if you are looking for the visible show of your cage there is still plenty to chose from.

my advice is unless it is a punishment – choose your knickers to match your chastity, it can make you feel a whole lot better for it!

After a busy trip (and a little tiring) away in Edinburgh it is time to get back to the day job – being Madam’s submissive maid.

I arrive back home at about 6 pm last night and Madam was waiting for me, she hadn’t been home long.  normally she would have picked me up from the station but the journey had a few changes of train and I had worried that I may have missed a connection and she would have been left waiting – better that she went home and I made my own way home.

I was dropped out by the gate at the road and picked up my bag and wandered up to the house.  The lights were on in the living room and I caught a glimpse of Madam looking out the past the curtains on the window and then the curtains closing, you can’t miss the noise of our gate!

As I entered the house I was greeted with Madam calling from the living room,

“drop your bags, strip to your underwear and come to me on your knees!”

We have done this before so this wasn’t too much of a surprise, I quickly removed my jacket, shirt, tie shoes and trousers.  I also removed the Opaque knee high nylons that I had worn as socks to cover my stocking clad ankles.  Now just in bra, waist clincher, stockings and knickers I got on my hands and knees and crawled into the lounge.

“Eyes down Dear, come to my feet!”

Madam had one of her feet on the floor, in black heels and in black stockings.

“Have you missed me?”

“yes Ma’am, I always miss you when I go away.”

“Kiss and worship my shoe and foot and tell me how much you missed me! keep your eye’s down!”

These weren’t her work shoes, these were a pair of her “fuck me” heels, patent leather, 4″ stiletto heels.  I applied my kisses and tongue to her shoes, gently at first, doing a few kisses and then taking time to give short heartfelt messages of how much I love Madam and miss her when I am away.

I know the rules are to focus on her shoes and her feet up to her ankle and no further until I am instructed to lick higher.

“I’ve missed you as well husband, I’ve missed your tongue.  John made such a mess of me over the weekend and you weren’t here to tidy us up.  I had to go out on Saturday night with his cum leaking from me – that’s your fault sissy!  my knickers were sodden by the time we got home!”

I could only mumble a “yes Ma’am, sorry Madam.”

“Not that you cared, you had your Master keeping you entertained.  How is your bum hole?”

“a bit sore Ma’am”

“Now you know how I feel after John fucks my arse, perhaps you’ll pay more attention to soothing it with your tongue in the future!”

I know Madam was teasing me, she knows that I love spending time giving oral to her arse as well as her pussy.  The first time I saw Sir mount Madam with the aim of fucking her bum I was convinced that she would stop him as it wouldn’t fit!  but Sir knows what he is doing when it comes to anal and fit it did and Madam was a very full but satisfied little bunny.

“I’m wearing the same things that I wore for John on Friday Evening, I hope that you like, my little sissy?  John fucked me all over the house, but you know that don’t you – we kept you updated on things.  You can start to lick your way up”

I slowly licked my way up Madam’s leg, keeping my eyes down.  taking my time, not going straight up, but doing a bit and then licking down the stocking clad leg before going a little higher.

as I got to her crotch, her wonderful pussy was covered by sheer black knickers, her lips and the trimmed strip of pubic hair very visible.  Her knickers looked like they were already damp.  I gave the damp patch a light lick and the taste of Madam was a wonderful delight.

I licked again and I as this was a bigger lick I got more of the taste, Madam put her finger under my chin and tilted my head.

“John left you a present.”

she pulled her panties to one side and I applied my tongue directly to her pussy and the lips, I could just get another taste and this confused me.  Sir wasn’t here and had been at work during the day.

Madam probably could see my slightly confused look as I licked at her.

“I had john fill a few parts of a ice cube tray with his cum and we froze them for you, I popped a couple of them in as you got dropped off”  they should be nice and ready for you by now.”

As I pushed my tongue into Madam the taste was much stronger and quite clearly it was the taste of Sir and Madam that now filled my mouth.

“John was worried that you would have missed him, so he contributed a few samples for you as a welcome home.”

I continued to lick and suck at Madam, cleaning her of Sir’s cum and then once I believed that she was clean to move fully onto ensuring that she had a suitable orgasm to prove that I had missed her.

I love orally serving my Mistress Wife, she is my focus and my world, and I do miss her when I’m away but as a welcome home you really can’t get better than this – as her sissy beta cuckold husband I can’t think of anything better?

From the last set of posts there were some questions,  Madam answered some  and provided some links.

For the other questions here is hopefully some of the answers.

The suspenders used on my waspie are from Pip and Pantaloon

detachable-y-straps-for-stockings

It appears that What Katie Did has changed the style of Waspie, but I must be honest I also have a waist clincher from them, Madam has several items from Katie’s stores and all of it is good.  it is worth a look if you want something to hold you firm.

https://www.whatkatiedid.com/collections/waist-cinchers

The inflatable toy that was in the picture is a Christmas present – it is an anal balloon.   it does have a tendency to make me feel uncomfortably full, particularly when I’m doing 15 minutes of corner time.

From Madam Alice

From the comments on the last few post here are some of the links

For the open crotch tights by MissO

https://www.stockingshq.com/tights-c1/p201-shiny-20-denier-open-crotch-tights-p2477

John provided me with the details of the sleep suit, it’s from Ebay and made by a lady called Sadie.  John said that send her a message with what you are after and she will send you what measurements she needs and in a few weeks you’ll have your outfit.

ADULT-BABYS-MAIDS-SISSY-UNISEX-GORGEOUS-SATIN-LACE-ROMPER-WITH-SKIRT

I wanted some MP3 or MP4 files that would allow oral and anal training to a metronome so that I could give billie a couple of unsupervised training tasks with objectives.  I did a internet search and these 2 popped up – they are a bit cheesy but they do what I want.  I have 2 files a 17 minute and a 30 minute file.

https://www.pornhub.com/17 minute Anal trainer to a metronome

https://www.pornhub.com/30 minute metronome anal trainer

I may get billie to do a video review of them when he gets back as I’ve made him use both – several times already.  he can give a practical comment on how good or effective they are.

I hope that gives what readers were interested in.

From Madam Alice

I’ve been working from home today and I’ve seen all of the comments to my last post and billie’s last 3 posts.  Thank you all for responding, it is very appreciated. I’m sure billie will answer the comments over the weekend.

Billie will be away until Tuesday and so I am currently without maid for the weekend.

How will I survive???

I’m sure I will manage, but billie will have some work to catch up with.

So I have started the weekend, work was finished at lunch time, I’ve bathed and I’m now in the living room with a glass of wine waiting for John to come over again.  I think he won’t be too long as I’ve just sent him a selfie of his naughty girlfriend here on the couch.

So what’s the incentive, oh I’m just here in 5″ heels, Fully Fashioned stockings, a waist clincher and a quarter cup bra, the only other thing I’m wearing is cherry red lipstick on a smile….

I think he’ll be on his way quite soon, don’t you?

Madam required me to take a photo of me wearing my evening working dress.

 Madam likes me to have the skirt hem at stocking top level and as it was noted by Sir that I was dressed incorrectly as I didn’t bring any of my wide waist belts, which normally provide a tidy way to hide the blouse being tucked into the skirt.

Madam didn’t want me to take suspender belts with me and directed that I should take one of my waist clinchers and my waspie.  The waspie is from What Katie Did and I replaced the orginal suspenders with the double suspenders as seen in the next couple of images.

while these suspenders are a real faff to put on they are definitely worth the effort as they hold the stockings really taught.

 Sir sent a message to tell me that I should work for the evening without panties and to plug myself.  at several times in the early evening Sir would contact me via WhatsApp and require me to show that I was still dressed correctly.

I must confess that I’m not a fan of wearing layers of stockings and tights but as Madam pointed out they do help with masking some of the hair on my legs – Madam still wants me to keep some of my male hair so that I still have the humiliation of being a cuckolded submissive male that cannot pass as a female (as if!!)

Task 1.

Madam and Sir  set me several tasks last night, and while the initial plan was to do the posts prior to going to bed that changed when Madam only finished my tasks at 1am this morning, but more on that later.

Firstly I laid out some of the items that She wanted me to use last night, I sent these through to her and Sir and then went to have my bath and clean up.

Madam told me to take a photo of my caged penis/ clit in comparison to my Master.  Master was given to me at Christmas as my travel companion when I am away with work.  Madam chose it as it is of similar length and size to that of Sir.

 As you can see Master is significantly bigger than me even when not caged it is significantly bigger than me.  

Last night I was tasked with several period of oral worship of Master and Madam provided me with a couple of MP4 anal training files of different durations which I was tasked to follow at several times last night.

Madam also told me to show that penis is on par with my cock gag which I had to wear during several of the sessions with Master.

 I have to confess that I’m a little tired this morning after a late finish and waking twice in the night – having now been in chastity for about 3 weeks I still wake in the night occasionally with night time discomfort from my penis trying to erect.  its almost like my penis is remembering it’s recent freedom.

Madam set the rules that if I wake then I needed to do my “exercises” to help me get back to sleep which is 10 minutes of oral worship and then 10 minutes of fucking myself on Master.

I’m a slightly tire bunny this morning……..

From Madam Alice

Billie left for Edinburgh yesterday and he has been out delivering the training today.  I sent him an email this morning with a few things that I want him to do and work through this evening when he is in his hotel room.

My understanding is that he will have little evening work to do today but tomorrow evening will somewhat busier for him.

So what has his evil Mistress done to him?

Well firstly I packed a few things in his bag on Monday evening for him to take with him.  Also on Monday night I released him from the cage so that he could have a supervised shave and clean, once done I locked him back up.  Part of me wanted to add his punishment attachment to his cage, but I thought better of it.  He will be a away from home for a few days so that would be a little bit too much – I normally only add the spikes for an afternoon or a day at most.

A few of the things that were packed were things that he got as Christmas presents from John and I.

One of the things was a nice sleep suit for him with some tights.  John had this made for him from a nice lady on the internet, it is based on an adult skirted romper suit.  To use John’s explanation of the idea for the romper suit – what should a sissy maid sleep in?  we measured billie on the basis of getting another maid outfit but chose this instead, it’s in black satin with white lace and rather than be sized for a nappy it is sized his chastity and looks a bit like a maids outfit without the apron.  The romper doesn’t have the gusset  snap openings but John asked for a zip to be fitted at the rear to allow access to billie’s sissy bottom.

The sleep suit is to be worn with black tights, we have mentioned before that we are not fans of tights but when they are open crotch tights then we do approved, the one’s that I purchased from StockingsHQ are from a company called MissO, and they are absolutely devine –  I’ll definitely be getting some more of these and not just for billie!  I’ve added a link to the web page.

https://www.stockingshq.com/tights-c1/p201-shiny-20-denier-open-crotch-tights-p2477

One of the other Christmas things that I packed was billie’s “Master”.  When billie has gone away with work he normally takes a butt plug or two and may be a dildo, well I bought him a special dildo for when he has to go travelling.  I selected it as it is the same size a John and I felt that billie should have a travelling companion that would remind him of what is keeping me company while he is away.  It has been made clear to billie that he must always refer to the dildo as his “Master” and he can only use it while he is away.

I also added a set of his ankle, wrist cuffs, leather collar and his cock gag for him along with his blindfold hood.  I want him to do some corner time while he is away and that will be done with him restrained.

Billie packed most of his own lingerie for the trip and I added a few bits, he has plenty of stockings.  I did make him take the suspender belts out and replace with his waist clincher and his modified “What Katie Did” waspie.  He also has his basque and I slipped his Merry Widow  in with things as well.

For evening work wear I think I saw one of his short skirts go in and also one of his blouses.  I think he is well prepared for his trip away.

The last item that I added to his bag was a sealed envelope with a USB memory stick, but more on that later.

Having spoken to him last night, he had arrived in Edinburgh later than he had hoped and his plan was to go out get food and then shower and bed.  So I wished him good night.

This morning I go up early and composed an email for him with a few tasks.  This evening my darling hubbie will be at the long distance mercy of John and myself.  I informed billie that he must eat at the end of the working day and before he gets back to the hotel, once back he is to shower and douche himself ensuring that he is fully clean – inside and out.

Once clean he is to dress in his bra and waspie and stockings, blouse and skirt, he is to take some photos once dressed and email them to me, this will allow me to know that he is dressed and ready.

His phone and laptop must be on for the whole evening and he will get more instructions via our “family” whatsapp group.

I also told him that he should identify a corner in his room where he will be sent to when directed and also 2 places to fix his “Master” – one for the kneeling position and one at waist height.  Billie has been told to make sure his sissy bottom is ready for the evening as I have found a really nice MP4 file which is anal training to a metronome and I have included it on the USB memory stick for my sissy to use.  I’m quite sure that billie will go to bed this evening well used and rather tired.

So what is going to happen this evening?  John is currently staying with me – keeping me company and keeping me satisfied while my sissy is away, and we intend to make sure that billie has some corner time, and several sessions with his “Master”  these may coincide with John and I having some fun in the bedroom ( and living room, and kitchen and….you get the picture).

Billie will also have to take a photo of him compared to his “Master”, just so that you can see the comparison between my hubbie and boyfriend – I know that billie is caged and it isn’t a straightforward comparison but being a cuckold does mean that your shortfalls are often highlighted.

A few more photo’s will also be required and he will have to take one of his sleep suit to show everyone what a lucky sissy he is.

I’ve also told him that he will be required to produce a blog post prior to bed this evening and he can do that between the tasks that we give him.

I’ve also set the rule for him that if he wakes up during the night prior to his alarm going off, then he must get up and please his “master” with 10 minutes oral and then 10 minutes of fucking himself – that will hopefully make him tired and send him back off to sleep.

I’m looking forward to what he posts this evening.