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Journey to dress like a woman

Jo Had Some Alone Time
Posted:Mar 21, 2023 12:42 pm
Last Updated:Jan 9, 2024 11:11 pm
18005 Views
Saturday afternoon Jo was lucky enough to have some time alone at home so she decided that it was a good idea to make the most of it and getting a few photos and enjoying looking her best.



Now my friend believes that this is her favourite dress that I own and asked me to model it for her. Although originally I was going to wear my red Bardot dress which is a lot easier to get into.

After taking a couple of indoor shots I decided that maybe I should take advantage of the glorious sunshine so I decamped to the side of the house for a little while.



Once I had gotten myself sorted and dragged one of the garden chairs down the side from the rear of the house (novelty for Jo as that made her a lot more vulnerable to being seen than normal). I forgot all about being a lady and had to retake my photo again (although a nice unintentional upskirt photo)



After talking with my friend she said that I might require a longer dress as there's not much to prevent somebody from getting a good glimpse of Jo's ass if she were to lean or bend over.



Anyway after almost 2 hours it was time to put things back in there place before calling it a day so Jo had to put the garden chair back where it belonged before she put her this away too.

Some days Jo just wants to get out and I was happy that today was one of those days
12 Comments
Another Drive For Jo!
Posted:Mar 6, 2023 3:02 am
Last Updated:Jun 29, 2023 10:53 am
16675 Views
Well what do you know I managed to get some time again for Jo to see some of the weekend from the relative safety of the driving seat again.

After a little exercise and a coffee I went for a drive again. I was on the move for around 90 minutes and Jo thoroughly enjoyed the experience of a longer drive than a week or so ago.

The one thing that I knew before I got home was that she needed to pay for gas. It was something I knew was going to be required and like almost all the stations here it's self service.



I hope that the car behind me at the busy station enjoyed the view of this leggy girl pumping gas in front of them. As it's pay at the pump and Jo wanted something to drink it was required that Jo went on to somewhere else to get something for the rest of the journey home.



For this one I parked outside of the shop and then had to walk across the forecourt and to the back of the shop where the soft drinks are kept. I had to squeeze by another customer to get a soda and then off to the till to pay. A quick exchange with the cashier before I headed back to the car again.

Problems



Ok girls or even C/D's how do you stop this from happening whilst driving? Yes I know that it's a short skirt but my hidden treasures kept riding up whilst driving. I was not even trying to play with my skirt and it sort of upset the experience of my drive as every few minutes I had to hike my skirt back into place.

As I said if you're here early my photo's are yet to be added.

Jo xx.
6 Comments
A Pleasant Sunday Morning
Posted:Feb 24, 2023 10:25 pm
Last Updated:Jun 21, 2023 4:13 am
16640 Views
Sunday morning I took part in a charity run nothing too exciting for most. I enjoy running but if you were to probably see me in action (or as some might say inaction) I'm a plodder. I've no chance of winning either the race or even my age group.

The one benefit was that it was a glorious February morning unlike the original-5 with bitter wind chill in December (it would of been brutal) night run admittedly I preferred the original night run idea, throw in I didn't have to get up at stupid O'clock in the morning to drive an hour to get there early enough to sign in too!

Anyway after the run I took the advantage for Jo to drive home and have a rather brief walk about on the way. Thinks might not exactly match in my picture but who cares! This lovely young lady stopped for a stretch and enjoy the sunshine on a Lazy Sunday Afternoon just like the Small Faces might say.



One piece of the Mulberry Harbour in Portland Harbour not used in WWII
9 Comments
I Had An Hour Or So Free
Posted:Feb 9, 2023 1:40 am
Last Updated:Mar 1, 2023 3:20 am
15672 Views
It's been difficult for quite some time to be able to slip into something nice at home over the last couple of years. An awful lot of us closet girls have had a real difficult time since the plague entered the world.



This is one dress that although has been in the closet for years this girl just did not really think about trying it on until last week. It's a lovely dress which must of been crying thinking when is she going to try me on instead of the LBD behind me!

After a little time in that it was time once again to get into the LBD because which girl doesn't like to be seen in one. I wish I had some shoes to hand that I could of worn but sadly some things had to be stored away for a few days.



Jo xx
10 Comments
Very Old Photos
Posted:Dec 1, 2022 5:31 am
Last Updated:Feb 26, 2024 1:00 pm
12848 Views
Here are a few photos

I found these photo's recently from almost 20 years ago, sadly no head shots as I didn't have the ability to hide my ugly face back in those days.



This Karen Millen Asymmetric dress is one that I'll always wish I hadn't purged all those years ago. Sadly somethings can't be helped and am sure more than one girl has done the same over time.



This is another that went by the wayside at the same time but it was fun walking around my place in these boots!



The red dress would be very useful if I was working in an office environment but sadly that is not the case then or now.

Go on let me have your opinion of how this mid 30 year old girl looks in these sadly long lost things.

Jo xx
11 Comments
Spending Time Away From Here
Posted:May 26, 2022 1:43 am
Last Updated:Feb 9, 2023 1:21 pm
11709 Views

I've been some time on another site. It's a lot easier to interact with each other even as a standard member with access to chat to so many similar minded people.

Last weekend I was away from home and stuck in a hotel in preparation for an event early on Sunday morning. So I spent the evening talking to a friend from the sight talking while dressed.

I know that I wasn't in the same room but all the same 2 hours in female attire talking to Mary again was great fun. She's such a nice lady and she says that if we were in the same area she would of loved to have me on her arm going to one of the clubs she regularly goes to back home. Oh how happy that makes a nervous girl feel!

My one regret was that I decided to get an early night instead of going outside dressed but I'd had an late night followed by an early start and I really needed a good nights sleep.

Oh well until next time when I get to spend a night away Jo awaits another outing
5 Comments
It's Just Not Fair
Posted:Apr 6, 2022 3:58 am
Last Updated:Feb 15, 2023 1:29 am
11634 Views
Well it finally arrived. I'd been waiting patiently for months for this weekend to arrive on the calendar, I'd been watching the days turn over.

Then how does the Great British spring weather get involved temperatures plummet and there's a bitter easterly wind blowing and all hopes of Jo going for an enjoyable walk disappear out of the window. Earlier in the day there was even a little bit of snow.

There's no chance that I am going to freeze my non existent tits off just to enjoy the big "smoke" so sadly I was stuck in my hotel room instead although I did have the enjoyment of talking to my American friend Mary as planned on Skype.

Actually being seen whilst dressed is a hard thing when you are a died in the wool closet girl like myself still took a bit. Although once the message was sent saying I'm here it would of been rude to back out of my plan.

Also a first time, Jo was seen wearing earrings alas sadly not outside her room.


And I bet that you are getting fed up with my other outfit too but here's a better photo with my new shoes

3 Comments
Can't Get Into Anything In Ages Then Suddenly Boom
Posted:Feb 18, 2022 2:32 pm
Last Updated:Apr 7, 2022 12:46 pm
12105 Views
It's been ages since I have managed to wear anything sexy. then in the last couple of weeks I've been for a drive & a walk dressed in a dress. Then just a drive in my new shoes.

Due to working late early in the week I decided to go for another walk to give my shoes a little bit of a wear. Only downside was that the wind was a little too strong for my hair (I know that I needed a hairband but too late now).

After getting into my clothes it was time for a brief walk on the cliff top over the beach to enjoy the views and then a trip to the beach for a walk on the prom, sadly due to the time of day it wasn't exactly warm (it is winter here)



I even tried to make the camera work for me with the wind coming from behind it but sadly the wind kept getting blown down before the timer gave it a chance.

I think that I need a camera man/woman



Sadly
2 Comments
Another Brief Outing
Posted:Feb 12, 2022 9:21 am
Last Updated:Mar 30, 2023 6:35 am
11940 Views
Like a couple of weeks ago Jo decided that she wanted to go for a drive early on Saturday morning.

Also good news was that my new shoes arrived too so it was also a good idea to give them a test drive.



Whilst trying to take a selfie I managed to completely mess the shot up, although for a bad one I do quite like the outcome, what do you say?



Now this is what I was trying to take but maybe next time I'll get the sun from in front instead of behind although I never really had time to think about the light.

The new shoes are almost exactly the same as the previous shoes although these are a little lighter in colour and 1 size smaller.

What do you say?

Jo xx
7 Comments
A Pleasant Evening's Drive
Posted:Jan 25, 2022 6:13 am
Last Updated:Mar 7, 2022 10:14 am
9005 Views
Had a day out this past weekend so I took the time I was alone to have a little fun and enjoy the drive back home. Once I left the motorway and had some time to try on an outfit or two, luckily today I could do the zip up on my dress!



Along the way I had to stop for gas as I was sort of running low. Although I could of got home it was more along the lines that I didn't want to get the crap from the bottom of the fuel tank. The trouble with my bank card is that I am unable to pay at the pump so I had to pay at the cashier in the gas station. Photo Below that's sideways



I also stopped off at a provincial railway station to get a couple of out door photo's taken while I was lucky enough to have the time before needing to get home so I took a few shots here.



Then it was time to move on and as it had been a while since Jo had needed to use the girls room I thought that I had better make use of the motorway facilities before I headed home and changed. This for me was the hardest part of my day as I hadn't been in the ladies rest room out in public since I used to clean them quite some time ago.


5 Comments

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