Deep cleaning this evening whilst working, got work to do between 7-12 this evening but for the most part it’s checking it’s trundling along. So current plan is to clean some of Miss clothes and such, whilst doing a hygiene routine (shave, enema etc.)
Miss seems to be a little more back to herself which is great to see, she’s even planned in gaming time for herself. So it’s only a small update but might add some more later on.
Today marks the 13th day caged. Only unlocked once to do a shave, after which it was locked back up and my insides cleaned out. Whilst performing my enema I did leak, since then I’ve had very slight pains which have come and gone over the time caged. Its never been enough to ask Miss to be unlocked though.
We’ve not had much playtime but we’ve got a weekend planned away which we’re both really looking forward to, and think Miss is hoping for some play. We’re both working to get back to ourselves, my click back to me has given Miss a bit of whiplash so it’s expected it’ll take a bit of time and hopefully this coming weekend will help.
Not much kink but a touch, we had a lovely day filled with tasty food.
Miss started the day by laying out panties and a bralette for me to wear all day. A pretty blue matching pair which I had on all day gives a bit of cleavage to this slutty little sissy. We first headed for breakfast and had a tasty 2 course breakfast meal.
Then it was home for a bit of chill time, followed by a Vietnamese tea before the theatre (I can highly recommend everyone’s talking about Jamie).
All day long I was wondering if people could tell I had the bralette on, and were the straps showing, did my small titties show through my clothes etc. Always wondering and always turned on a bit.
I’m really looking forward to Miss getting more adventurous with her challenges for me x
So after the not so fun ass whipping last year (and the start to this) gave me, and Miss (although to a lesser extent) I’ve come to the conclusion that with life having got in the way too much this year is the year for us (fuck the other years!). Its taken up to this last weekend for me to feel good enough to shave, clean out with a good enema and ask if Miss would allow me to be caged. There have been work choices I’ve made in error but I think now I’m finally getting back to being the submissive, slutty, sissy me that I am deep (although when out, not very deep at all!) inside.
See this last week was my birthday, so this weekend involved a trip to my family filled with cake and nice food (much like my birthday which Miss treated me very well on (more to follow)). So I’ve been wearing panties the majority of the time even when down, although some boy pants were worn at various points either because I was way too low or because of tummy problems. I even bought myself a very cute little skirt that I’m hoping Miss has me wear for her at some point maybe with a few pics taken to show you guys, girls and gurls.
I’m really hoping for Miss to feel herself again, she’s picked up a lot of hobbies which is brilliant but I want her to feel that again she can take full control and make demands of me and I suppose this post is me voicing that. I really want to get back to being her sissy slut and doing anything she wants as and when she wants.
So been a little quiet the last few days, but there has been some kink in the mix of crazy amounts of work and stressful days. Works been a bit of a bitch, just got a few new things we’re set to do which is all fine etc. but first day we’re due to start 3 client facing systems decide to go kablooey. Leaving me and my one colleague in my team rushing around to sort them and forgetting our new task. Gotta say less than ideal, we got it done about 1 hour or so later than planned annoyingly and with a bit of snark from our manager. What can we say multiple systems break we fix them in an hour and then get snark for the new thing slipping our minds with the critical incidents setting fires…
In terms of kink though, I had another spurt (pardon the pun) of ejections. Miss was making cake for a charity day at work (same charity as my custard & cinnamon buns), and in between bakes she had me come kiss her beautiful ass. As she was due back in the kitchen she told me I had to follow and didn’t instruct me to stop kissing, I must say you see people doing this in videos etc. and its quiet the workout to keep up with the walking folk and continue to kiss an ass. Immediately Miss laughed a bit and every bit of my body reacted with me very soon finding myself in very damp panties. Once she was done in the kitchen I continued following as she’d not said to stop and was lead to the bedroom where I was placed at the end of the bed, face inches from her after handing her the wand. Again whilst she was playing I left several wet patches not just in my panties but soaking through to the bed itself.
Now the funny thing is we have a very powerful wand… during playing Miss pulled my head that close to watch her playing that I actually found my head was touching the vibrator, on several occasions the bridge of my nose too. It took so much willpower not to laugh (its rather amusing having a powerful vibrator touching your head!) and actually couldn’t help myself but laugh once, and begin sneezing a few times (bridge of nose + vibrator = better than pepper to make you sneeze!). After a few orgasms Miss stopped and I had to tell her the above, we both laughed and cuddled for a bit before going back to snuggle on the couch.
Other work stuff in between has just been chaotic at best, especially as Miss has had a very bad tum since around Friday/Saturday (can’t recall exactly) so we’ve been dosing her with pills & milk of magnesia, hopefully she’s getting better as I hate seeing her in pain like she’s been.
Anyways, thought I’d give a brief update on what we’ve been upto. Please don’t hesitate to comment or drop me a message.
The baking went down well today, I may not have won star baker but then the judges 1.) didn’t like cinnamon & 2.) didn’t get any of my egg custard because it was gone before they could.
Today again Miss hasn’t been feeling great, so an evening looking after her. When I got home I made a shopping list of items we need and meals we could have over the next week and rushed to the shop. Spent next to no time getting things and rushed home to feed Miss, I’m only still up because I’m making sure she has leggings for work tomorrow. It’ll be a long day because I’m dropped her off at 7.30am and then working for a bit from home before going to the dentists.
The unexpected turn to my evening, whilst sat at my desk just toddling around online I kind of accidentally rubbed my nipple… and instantly started to feel that familiar pulse between my legs, and there I was not shooting more dribbling a full load. Now since getting back from the shops I’ve been plugged, in my nice little nighty and a very very sexy g-string. But this is the first time I’ve experienced quiet a reaction from nothing, now I’ve cum from just pleasuring Miss, I’ve cum very fast in other scenarios but wow a rub of my nipple and boom. I had started to get the slight familiar ache in my balls but this seems to have alleviated that too. So that’s a good thing, or else I’d have had to request unlock from Miss (I’m not kidding since surgery on my testicles pain there = me not walking/moving).
So I’ve committed to making cinnamon rolls and my signature desert for charity tomorrow. I know both things are going to take time and I was feeling a bit stressed that I’d done this (my own fault completely).
Miss had asked me to order food, and I’d snapped at her. All day I’ve been feeling super submissive and extremely horny and I immediately felt ashamed that I’d snapped at her, I did order food immediately and went into myself completely to try and chill and get a minute to calm my stress levels. I’m just waiting to put in the cinnamon rolls after their second prove now, dressed in the black skirt, panties & bralette top. I know Miss will read this so I apologise Miss.
Other than my indiscretion the baking is going fairly well and in general I think I’m being a good boy.
So I imagine different sissies have different reasons for enjoying/’enjoying’ being dressed up. For me it’s definitely enjoying it, I love Miss choosing out my clothes (the control aspect is amazing), and dressing me up in skirts, sexy women’s clothes and other cute items adds a level of humiliation to it.
I am loving the extra control Miss is taking, having me plugged more (which to be honest was mostly due to my guts) and making me do things whilst dressed (the drive out as I explained in the earlier post).
I think some of my reasons for wanting the dressing up aspect are based on my own life experiences, I recall being about 14/15 and playing truth or dare with a friend and I was the one pressuring to be put into his mum’s clothes, when I was even younger helping paint at home I was put into one of my sister’s skirts and had my family laughing at me. I think these things impacted me to such an extent that I really do immediately although not always noticably become humiliated with recollections of the painting incident, the somewhere internally I connect humiliation to arousal and enjoyment.
Psychologically I connect all these things to positive things despite the more often negative impact humiliation has.
Miss is feeling better, still tired and achey but much better overall. I got home today and after a short break was swiftly plugged and dressed in my pink skirt and the white top, Miss lets me choose the plug based on how I’m feeling and normally I default to the small glass one, today I chose the medium size plastic one (I’ll post toys pics at some point) to kind of stretch myself a bit, it’s not really much wider but it’s longer by a good margin.
I’ve done a swift clean of the pots after I sorted some pasta for tea as Miss was already hungry. The larger plug I can definitely feel a lot more while I move around, so whilst doing a swift sort of the living room (in prep for a Saturday with friends) each time I bent down it pressed nicely against me.
For the past 2 days Miss has been ill, so yesterday I worked from home to make sure if she needed anything I was there for her. Last night I was told to wear my black skirt again whilst I sorted the few things I did, taking out the rubbish being one of those things. The way we’re setup we have to walk past neighbours living rooms to get to the bins, so there’s me in my skirt and t-shirt combo which I thought had a bit of a 90s vibe (and Miss would later confirm was cute) walking past a very well lit neighbours back door with them sat there. Embarrassed much! (So fun)
Today she woke with a migraine, unfortunately I had to go to the office though, but thankfully she’s managed to shower and eaten something. This evening I’m finding myself giving myself one of my regular enemas (for cleaning and health), then I’m to dress in the pink skirt, plug and whatever else Miss wants to continue the list Miss made on Monday.