So today started much as any period of 24 hours does, me being awake till a silly point (4am today) before going to bed. Up around 9.30ish then after making me and Miss hot drinks having a time to wake up properly, we went for some delicious coffee and brunch at my favourite place. I’ve really come out of my crossdressing shell these past few weeks, and weekend before we went shopping for me and picked up a few bits and bobs, namely some leggings, skinny jeans and a dress t-shirt with a coffee quote. It was our anniversary weekend which we extended to a 4 day break and had a really nice time.
When we got back from brunch Miss wanted some fun, so I was stripped out of my skinny jeans and down to my lingerie. Miss had put my collar on (my leather anniversary gift to her) and we made our for a while with me leaning over her with her spanking my ass. Then she used her favourite toy to make herself cum. After another period of time chilling we went for a dog walk (Miss having forgotten about the collar completely), it felt kind of like the first time goikg out with chastity, or plugged. It’s a snug collar so every movement of it kind of triggers the reminder its there.
Also had an amusing realisation from Miss where shes realised she leans more toward being pansexual than hetro because she’s still super attracted to me in pretty lingerie and me leaning more towards gender fluid (this then resulted in my doing a mini “one of us” chant lol).
I managed to finish my Christmas shopping on Tuesday, I took the day off work so that I could get it done with and by jove I did it!
On the way home I did nip into a local sex shop, mostly to browse and be out of the house in leggings with very visible boobage (seriously bra adjusting has done wonders to my bust!). I stopped by on a quiet night road to take my trousers, socks and jumper, then headed straight to the sex shop in my 3/4 leggings, stockings, t-shirt showing off clear boobs. Parked as far from the door as the small car park allowed, then in my heightened horniness forgot the mask so had to go back to my car and recross the car park. 2 other customers browsing, and 1 staff member just to add to my mild humiliation.
I did a full loop slowly round the shop, and picked out a glass plug nearly straight away. Then continued browsing whilst the other customers paid, also picked myself some nipple clamps. Picture showing some leggings
Today was a looong old day of work, lots of meetings and having to take the car to the garage followed by virtual Christmas party with my team. To add some spice to the day I was once again in full underwear underneath my boring boy clothes. We did however get a brand new sofa which has been lovely. Then this evening I got a bit daring taking some pictures for Miss on the evening dog walk.
Delayed post with a bit of a thing about our fun, Miss had ordered me stockings for Christmas and has given them to me early (we’re spending Christmas with family) and other than today I’ve spent every day wearing full underwear including stockings switching between using suspenders or straps from the corset on days I was wearing that. It really does make a huge difference on feeling my legs under clothes and constantly reminds me of my sexy underwear (especially walking as the straps rub lightly against my skin).
Onto the Wednesday fun, after a day of being in the office with constant hesitation on whether people could see my suspender straps when/if my tshirt rose up I got home to Miss saying it was time for me to do things to her. We warmed up with kissing, touching etc. and then Miss got on all 4s and I was licking her from behind whilst Miss teased her nipples, during this I leaked on the bed and Miss came a few times. Then I was told to go uncage and I could have a reward of fucking Miss, problem being that after leaking all over the bed lets just say “he wasn’t prepared” and in substitution I was using my hands whilst trying desperately to get hard. Multiple orgasms later from the vibrator, my fingers & me furiously trying to get hard for her, Miss collapsed on the bed and giggled at how at this point he finally started to rise now that she was spent.
So both an amazing, humiliating and frustrating experience (what I got into chastity for really isn’t it).
So it’s been a long while since I’ve made a post at all and figured it made sense to put something together with a few pictures and such as way of a mini apology for the time.
So blackfriday & generally wanting some more sissy dress up clothes came together and got Miss’ boy on a small shopping spree. picking up bras, suspenders, panties and a corset. All of which I’ve fallen in love with and now wear daily, I’ve had a few bras from shops and such but went a little ham on getting some sexy sets xD. I’ve got pictures of 3 of them below and then a few pics of Miss wanting to see as she’s just described it moments ago “the merchandise”.
We have been doing a bit more in terms of me dressing up around the house and under silly boy clothes lately with me being in dresses, just the underwear or such and I’m loving it. We were actually out today and had an older gent stop to ask us directions and before he spotted my stubble (Miss doesn’t want me shaving which I’m fine with) he said “Hello ladies” and once we’d given him help with the directions and drove off I said to Miss “Is it bad that I kinda liked him saying that”. Miss has also been a bit happier demanding me show myself off when we’re out (obviously not forcing our kinks on others etc. and making sure its safe).
Out and about while whatever the weather as proven by the snow on the ground in one of them! I love my Miss so much xD
I’ve also been spending ALOT of the time plugged up and in stockings which just make me feel sexy xD
Last couple of pics I promise one to show (to the eagle eyed) my plugged up sissy hole and the other to show my working day casual style.
Yesterday was a really fun day too, we had a couple of friends around for a games day where we played board games, caught up, had delicious food and then listened to some music before I dropped them off home. After dropping my last friend home I found a quiet place and stripped down to my stockings, panties, bra, suspender belt and plugged up sissy hole. Wearing just that I started to drive home (taking a slightly longer route), now this was at 2.40am so few people around but “some” and some stopping next to me or around me etc. I felt so exposed, slightly humiliated and so freaking horny. Whilst I was going I did leak into my panties and on getting home put on my boots, picked up my trousers & top and walked back into the house in naught but my sexy underwear then had to spend some time chilling out as I always do after doing games day drop offs but this time feeling sexy.
Getting into bed last night I found a Miss that was still very much awake, struggling to sleep following on from having a cold and being looked after. Snuggles ensued with me being big spoon for a time until Miss told me to roll over, she decided that then was the time to start teasing her cock through its cage. Moaning and groaning whilst miss slowly teased her caged cock which has basically been caged apart from cleaning times since early August it wasn’t long till she got me to the very edge of exploding in the cage, and I soon found myself lying in a very big wet patch as she pushed me over the edge.
Then she told me to get her favourite toy (https://www.womanizer.com/uk/pro-40#color=77) sadly it hadn’t been charged recently so it was to the trusty wand, I was allowed to kiss, suck, bite and tease her nipples whilst running my hands over her body (I LOOOOOOVE doing this) and soon Miss was cumming hard.
Very small update but its been so long that I needed to get a new post up xD
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.
Last night as many nights really, I found myself unable to sleep so rather than just fester or play games like I’d normally do. Instead I took the time provided by my abnormal sleep to epilate my legs and bikini line, it does make me feel more me (the sissy bitch me) so after my drive to work this morning one of my couple of days in the office a week I keep finding myself enjoying the feel of my smooth legs through my silly both clothes.
Annoyingly it does seem that the sleep abnormality is tied to work because the entirety of last week whilst we were on holiday I was able to sleep normally.
I know bit of a strange update for me but as I use this more as a journal figured I’d put this out into the aether.
Starting the week as I mean to go on, attempting optimism which is in itself strange. Today I went with a very cute thong for my underwear choice.
I’ve been caged a little over a week now and starting to feel it, my need to be penetrated, used or humiliated has been on the rise throughout too. Its clearly tied to the cage and the feeling of being owned that gives constantly.
We’ve both been a bit tired but I’m trying to keep ontop of that and stay in the mindset but still have slips of snappiness related to the tiredness.
Chatting with another sub online the other night, he was going through a tough time because of something he’d been aroused by and thought that he wanted to act it out because the level of arousal. After chatting for a while and describing experiences that were similar in that I sometimes have fantasies regarding cuckolding, being outed to family etc. which can all be extremely vivid, extremely personal and exceptionally provocative during those times when I do. However and it is a very big however I know that those aren’t things I ever want to truly experience I get that for others they’re kinks they live and breath but to me they’re on my list of “Most definitely, 100% no”, cuckolding for example I think would damage my relationship with Miss (who for new readers is also my wife) and that isn’t something I would ever risk regardless, it’s also something I don’t think I myself am mentally strong enough for not for it to actually happen I’ve been in relationships in the past where I’ve been cheated on (several times off the top of my head 3). Each time its hurt in unimaginable levels and whilst I imagine for some there’s a sense of catharsis in having some limited control of the situation, or even putting themselves through similar situation etc. but for me its a big blazing red light.
His fantasies were scaring him as they were on the extreme side of the kink world and I like to think I helped guide him a little bit.
It really got me thinking how over the years (I’ve dabbled, and fantasized about Femdom, chastity etc. for christ nearly getting on 2 decades… SCARY FACE MOMENT!) I’ve grown to kind of (not completely but getting there with help from Miss) work out what it is about kink that I like, what it is I want and need and looking back how whilst not the thirsty subs you get online lol how I’ve grown in my knowledge and understanding of myself and kink. I also recently picked up a copy of the “Yes, No, Maybe Workbook” which I’m looking forward to going through and see if I can expand on my understanding even more (I read voraciously and when I get into a subject I NEED to know things).
I’ve been having a lot of desires for humiliation and the lack of control aspects of play these last couple of days whilst caged, but yesterday was absolutely exhausted to the point I got home, went on the computer a short time before eating then hastily collapsing to sleep on the couch. Part of why my goal today (mini goals and such) is to sleep before 2am, something which hasn’t happened in several weeks!
So signing off on route to succeeding in that goal. As always anything anyone wants to ask regardless of subject or anything please feel free, I always respond to my comments and really appreciate input.
After so long not doing anything for my sissy side, this weekend has been like a second (or third, or fourth etc.) coming. Yesterday was spent getting nice and smooth with a nearly all over epilation (still need to ask Miss to deal with my sissy ass) and the majority of today was a very thorough enema.
After all that I’ve been feeling so much lighter and happier, even though I’ve only just finished. I feel ready to be my sissy self again and be the slutty sissy Miss deserves to please her. Short but sweet post for now.