Crossdressing | Me, my kink and I

Aug

Last nights fun

After spending a lot of hours dealing with an enema that was a long time in coming, I asked Miss if I could be locked. First she told me no, but she was planning to lock me later however after spending some time on the couch Miss came back into the room to say she’d changed her mind and that yes I could be locked now and to meet her in the bedroom.

On going into the bedroom I was told to strip (I was dressed in a pair of tiktok leggings (they’re amazing!)) and then told to get between her legs and kiss the parts which still hurt from being epilated the day before, kissing away like my life depended on it Miss started grinding herself on me and had me kissing her lips with the same vigor in no time (I admit I leaked on the bed sheets during this). She then forcefully pushed me away and told me to get the toy she’d got me for our anniversary, Miss tried putting it in but it was a tiny bit too big so I took over trying to get it in as I could judge the angle better, during this Miss would tug on her cock and balls which was painful but felt amazing being totally at her whim. After taking a minute out to relax myself I eventually got the plug in, and Miss started to play with the remote (it vibrates and has a part that makes it feel like being rimmed!) and I was in total pleasure whilst Miss still mercilessly teased her cock and balls.

Then Miss stopped and told me to start licking her ass whilst she was on all fours playing with her favourite toy, I couldn’t get enough of being her sissy ass licker and after I don’t know how many orgasms Miss lay down and we cuddled.

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 :))

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.

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.

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.

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).

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.

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.

Sep

Woo woo

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.

Sep

Making sure Miss is ok

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.