So the last couple of days I’ve been wearing a bra whilst at home, we did some shopping pre holiday and Miss picked me up a non wired t-shirt bra which I wore a few times during the trip, its a 40C and fits fairly well. We did measurements using abrathatfits.org/calculator.php which admittedly put me at a 40DD which we reckon would be MASSIVE for my ample sissy bossom. Since we’ve been back we picked up a couple of underwired options in a 40B (my suggestion I admit) that I’ve been wearing since when not in bed. It has definitely made me more aware, we’ve only just got back from our post work dog walk and I couldn’t help wondering if anyone noticed during the walk I mean, when I look down I can definitely tell I look a little bit booby.
I do really want to get back to having the time to maintain my smooth from the neck down & cleaning of my insides, real life has been a bit of a bitch for that. I’ve also found myself daydreaming of Miss putting me into humiliating situations/conditions a lot. I think my brains rebelling against the real life and not feeling my sissy self.
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.
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 😮
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.
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.
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.
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 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.
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