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Posts from the ‘Crossdressing’ Category

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.

30
Aug

Day of tidying and BVibe… WOW!

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.

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 😮

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 :))

21
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.

3
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.

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