Having been walking pooch each evening in sissy clothes, it really got me thinking how much I enjoy dressing up. Especially being a little show off slut like I was the other night. I’ve always been a bit more uninhibited than the average person but dressing up and being outside makes me that little bit excited, that little bit scared and all the turned on.
I’ve been caged pretty much all of this month which probably adds to that last part but it does make me want more clothes, a better option for hair management (currently looking at home laser hair treatment options). Then once covid has come and gone (or is more under control) I could in theory just get the areas the home laser treatment can’t do waxed.
In other news Christmas has come and gone and I love everything Miss got me, she gave me a few bits before we travelled to family (few kinky items) and we brought everything else over with us and I’m over the moon with everything and glad everyone enjoyed my first Christmas Dinner (although for a much smaller group than normal due to following all the guidelines :))
So following the UK changes to Christmas & the tier system our family plans took a major hit, which lead to me needing to take a trip to collect presents so they can be shipped to my sister. Normal drive there (although plugged, wearing fishnet tights, and a pink basque) but on the way back Miss had decided that I was to change out of my silly boy jeans and into a more appropriate skirt. To be followed by sending picture evidence, now the road between our city and Manchester is hilly and remote but fairly well travelled so I had to find a spot to stop over.
After finding a spot, I turned off the engine took out the key and ran to the passenger side of the car. Taking my shoes off outside lead to cold feet but I was too excited to care. I hurriedly took off the jeans and started taking a few snaps for Miss to enjoy, at which point cars started passing me stood in the dark next to the car (inside lights on) full beams of these other vehicles in my direction, I have no way to know what they saw but it made my blood pump so fast thinking someone may have seen this sissy little bitch by the road side, or thought they just got a view of a woman changing.
After letting my heart slow a little I got back into the car and moved on thinking of home and Miss, it wasn’t till I got to the next layby that I thought it was a nicer spot for some outside the car snaps getting excited again I was out of the car without any hesitation this time a few cars rushed by and I knew I looked hot as fuck and didn’t care what they saw, again out comes the phone and snap snap snap flashes in this black wilderness occasionally sprayed with car lights.
When I got home eventually after driving through McDonalds drive through all dressed up and masked to pick up our food I find Miss on the couch with our puppy all snuggled not feeling herself. So we ate looked after our pooch and I took her for her nighttime walk, several times having to bend right over (no one around) to stroke a very nervous slightly poorly pooch.
And that leaves me here, dressed up and horny but wishing a pooch and Miss to feel better.
Miss came down in pain on Saturday morning (Friday night as she went to bed). So the weekend was spent looking after her mostly, making her call the non emergency NHS number on Sunday night which resulted in a rather unexpected visit from a pair of lovely ambulance men, net result of which was “Call the GP in the morning”, although they did offer to take her into hospital.
Monday when we she got the call back resulted in a couple of prescriptions for a large amount of pain meds. Thankfully she’s starting to feel better and got a much better nights sleep last night (as did I, I’d previously had 2 sleep less nights with a few naps during the days to top up).
Hoping we can get some play in once she’s feeling better and definitely looking forward to restarting our daily walks. Neither of us has come down with CV19 as yet which is good news, and we’re still taking all the precautions advised. Can’t wait to get back to some normalcy.
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.
As Miss went to bed I started getting random “fantasy scenarios” pop into my head, so I messaged the first to Miss (it was that she sent me out for a drive dressed as I was), messages continued and it became evident that I was very sexually coiled (to quote myself “you’re driving me mad with lust… and I like it”).
Miss decided it would be a good idea if I went for that little drive and took some photos whilst I was out. I took a few in the car before setting off below.
Then I started my drive, deciding to drive over to nearby Castleton, as I was setting off plugged, dressed and caged I could feel just how excited I was as Miss’ cock began to leak in its panties. Clearly I was worked up and I was really liking it (its the effect Miss has on me!), as I was driving there were several cars I drove past which I wondered to myself if they could see me. Then driving through some of the slower roads (its in the country with several 60/50 mph roads on the way there, but also villages with 30mph limits) I was passing people and again wondering if they could see this sissy sat in the car driving which just proceeded to get me more excited.
For the little photo shoot I took after getting out of the car I took a photo of a nearby sign to show where I had been to Miss with evidence, as well as several pictures of myself which I quickly messaged to Miss.
I had a ton of fun and excitement on the drive there and back, constantly wondering and constantly excited. I hope I made Miss proud x