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Posts tagged ‘Crossdressing’

16
Dec

Christmas shopping and walking the dog

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.

10
Dec

Some fun on Wednesday and living in stockings

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).

5
Dec

What’s under the covers, and sometimes over

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.

1
Nov

On the right path

This weekend was a nice change of pace for us, we had some friends visit and played some board games while entertaining them and their little one. Had a lovely cheesecake made by Miss and generally didn’t get up to much else outside of our normal dog walks etc. I was left alone yesterday while Miss went to watch an anniversary showing of Harry Potter which was nice, me and our pup just having a relaxing day and having a big old walk in the rain.

I did manage to do a maintenance cleaning of my guts on Friday so have been plugged for the past couple of days as near to permanently as possible. I also ordered some new clothes for myself on Friday, a sexy lingerie set (suspenders, bra and thong) and a new jumper dress which should arrive this coming week. I do love dressing up, and especially love trying to be sexy for Miss. It always makes me feel extra slutty for her and lately I’ve been in that state of “ready to do anything she wants”, I have had a couple of points of leaking either while putting the plug in or even when doing epilation of my groin area. Miss has never been into cum play (past experiences have put her off anything cum related) but my immediate reaction has been to “clean my mess” lets say. Leaking in my cage hasn’t been often but the clean up has been every single time.

I do hope we get a bit more play time, and when I’ve got my new clothes I might do a wee fashion shoot so my next blog post can include some pics.

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.

23
Sep

Sizing and wearing

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.

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 😮

24
Aug

Yet another week

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.

16
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.

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 :))

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