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Posts from the ‘Crossdressing’ Category

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.

19
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.

18
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.

17
Sep

Being a little energetic

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

8
Sep

New Clothes Shopping

What could have been a very plain weekend turned into a very nice one, off the Manchester we went and out shopping (normally a task we both disklike). This shopping trip was different though, Miss had plans… we were shopping for clothes for me, specifically skirts and tops.

After walking round a large amount of shops we set on our last shop before going back home empty handed both a little sad we’d not found what we were looking for. Here in this last shop though we hit the jackpot, Miss choose several skirts out for me and then insisted I try them on. It was at this point I was anxious, in a good way. Who knows what they’d think/say etc.

Still not sure what they’d be thinking of a guy going into the changing room with three skirts and coming out and choosing 2 (Miss decided the last wasn’t that good (which I agreed with)). We went back to the house and chilled for a couple of days, occasionally sending messages and such to each other which just kept me aroused. We also went and did a bit more shopping for food and such where Miss spotted a few tops and other bits she liked which we picked up.

On the way back home today, Miss had me stop whilst we were driving back and change into some of the new clothes, top and skirt were to be put on at the road side (busy road between Sheffield and Manchester I add)

So at the road side I stripped to my cute panties and cage with nothing else and got into my new top and skirt, I felt slightly humiliated, 100% aroused and 100% submissive. I can’t believe how hot it was! Miss then couldn’t keep her hands off me all the way back, touching her caged cock and teasing.

When we got back, Miss had me check the mail and proceed to the bedroom where I was to do a little fashion show for her.

I think Miss approved as then I was told to hand her the wand and lie next to her, I was to only touch her nipples either with my hands or mouth. She told me I was to tell her how each outfit made me feel between playing with her nipples which I proceeded to. Outfit 1 which I drove in made me feel very cute, its a bit lady like and I really liked that, outfit two made me feel slutty and a bit cute (the nipples on show, but crop tops are cute!), and outfit 3 made me feel a bit slutty and also sultry xD. Miss must have liked my explanation and little show as she then had me lick her ass whilst she continued with the wand, I love when she does this as I feel like her little whore being used how she wants she allowed me to feel how wet she was with my face and she was fully dripping.

Sat here in outfit 3 writing this her cock is straining against its cage thinking about the wonderful weekend and play.

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