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Posts from the ‘Crossdressing’ Category

30
Sep

Cumming up to Locktober

So having been locked for quite some time now, basically since August 15th! (easily a new record for me). We are coming to that time of year, with Loctober, NOvember & No Nut December. I don’t know if Miss has any ideas on them but I’ve been wearing a bra regularly since getting one and had my first day in the office yesterday which cause my self consciousness to rocket but my horniness to raise too. We’ve managed to have a few times playing since I was locked which has been really good.

Looking forward to this weekend we’ve got a couple of friends coming over for playing games, I’m planning to clean my guts today or tomorrow in preparation for the weekend I do like being able to feel sissy even if its under boy clothes whilst the friends are round.

30
Aug

Day of tidying and BVibe… WOW!

So today we had no plans (yay! I’m an introvert and these types of days are my dreams). We went out early to go and get brunch, had a lovely walk and nice food and coffee which is always a good way to start a day for me. When we got back I had some time to myself played on my PC and then noticed Miss was napping, decided that due to this I’d go and do a small clean out with a quickish enema as I can easily do that without waking a napping Miss. Afterwards though I was to get dressed up for Miss and plug myself with the B Vibe we got and had very brief experience of (Miss accidentally turned it off during our last try whilst getting over excited xD).

Well… That thing is GOOOOOOD, first of all I admit I made a mess just putting it in it is a bit larger than the plugs we normally use and being in the bathroom on the floor putting it in did cause a large leakage. I was tasked with putting away laundry (it was about 3 weeks worth (long story…)), cleaning the bathroom and hoovering (I had to do a minimum of 1 of these today), I started with the laundry but Miss didn’t do much with the remote for the plug during this. Then had a break after way too much laundry putting away, and Miss decided to start playing with the remote. I was sat at my computer and after about 20 minutes felt the pressure building and immediately made another mess in my pretty thong. I then moved onto doing the bathroom and during 80% of cleaning the bathroom from top to bottom wiping everything and hand cleaning everything the plug was a constant source of pleasure, frustration and distraction. This thing is powerful, unexpected changes also help remembering Miss was in another room completely so I had no idea when they were coming.

Its a short short post for today, I’m not sure if Miss took any pictures but if she did I will update with those too.

25
Aug

Fitting

So a female friend of mine posted about an online bra fitting site a couple of months ago, I spoke to Miss about it as this sissy has never had a real bra and we decided after pay day that Miss would measure me up and we’d look to get one for me. It’s something I’ve always been curious about, and being on the chubby side I can have quiet a good cleavage *blush*.

Am looking forward to it, both the measuring by Miss (which will have its own bit of humiliation even if Miss just grabs a tape measure and cracks on with it) and then the looking and shopping for something in my size. As I say with the cleavage I hope we can find something pushuppy to and maybe something more for everyday wear under boy clothes. I’ve got a few bralettes which do a bit already so fingers crossed.

So hopefully this time next week I’ll be able to dress up and have a bra 😮

26
Dec

Thoughts and such over the festive season

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 :))

21
Dec

A very interesting evening

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.

3
Jun

An exciting dream

Last night seems my mind couldn’t get a break from its horniness, when I woke up this morning found myself struggling against the cage even more than normal after my little nocturnal movie.

Slept through the night but woke with a memory of dreaming the following…

Miss had me fully dressed and plugged late at night, took me to the car heels and all then had me drive out to the countryside. It was when we got there she had me get out of the car and bend myself over the bonnet of our car, arms outstretched. She then tied one of my wrists, ran the rope around the car and then tied my other wrist. She did the same with my legs, so I was there fully dressed up all slutty and spread eagle bent over the car.

Once she had me right where she wanted me she proceeded to pull down my g-string, took out my plug and started licking my hole like it was her first meal on months. After she’d had enough of eating it she spanked my ass raw, with some balls slapping for good measure. Then she got some toys out of the back of the car and fucked me senseless until I lost track of time. Then she untied me had me lay on my back and face fucked me till she’d cum so much my face was covered with her delicious juices. Then without letting me clean up had me drive us home for some after play cuddling on our couch.

24
Feb

Little late but I think I have some resolutions (or just things I’d like)

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.

27
Sep

That was unexpected…

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).

25
Sep

Baking and bad boy

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.

23
Sep

Why I like being dressed up

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.

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