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Journey to dress like a woman

New Shoes
Posted:Apr 12, 2024 10:17 pm
Last Updated:Apr 15, 2024 6:14 am
392 Views
I love my pink kitten heels but sadly pink doesn't really suit/work with anything I own. Yes the colour was bold, maybe not as bad as bright red but all the same.

I was hoping that these would of arrived before my recent trip to London. I looked in a couple of thrift/charity stores but none in my dainty size 10 (12 USA) feet.

My feet take a little bit of effort to slip into them but am sure that they'll fit nicely with a little bit of time.


5 Comments
A Weekend Away (Also my 100th blog Post)
Posted:Apr 10, 2024 1:59 am
Last Updated:Apr 12, 2024 9:43 am
683 Views
I had a weekend away recently so took Jo with me so that she could have a look at London. I liked the complements I got recently from my new dress especially form a Dutch lady Rosaenaluin, so I thought that my blue dress needed a night out.

I was hoping to wear some new kitten heels but sadly they never arrived in time. These would have been a replacement for a set that were ruined in the post, some things are just not meant to be. Sadly they arrived a couple of hours after I had headed out of town for this weekend.

First of all I wanted to try on my new heels which were a step too far (or maybe high) walking took a lot more effort than my kitten heels. I had a little go late at night not far from work just to try them out; going uphill was a lot harder than going downhill. I never fell over but I know not to buy any more.

After I had had a little down time in my room it was time to get ready to go out. First of all I wanted to take a couple of photo’s down the hallway in my shoes just to see how I look in them. I felt like a giraffe in them luckily I never had a long neck to get the extra height.


After having done the obligatory photo’s it was back to my room so that I could wear some more sensible shoes, sadly they just didn’t go with my dress but well sometimes you just need to get out. First off it was the walk down the hall to the lifts & stairs.


First stop was a trip to Waterloo railway station to see a place I visit regularly while working.
After admiring the view, from here I headed on to Waterloo Bridge. Sadly it was a little too windy for my liking and it really played havoc with my hair, at least I was prepared for this.


Finally it was back to the railway station to get something to eat before heading back to my hotel.


2 more stops at shops and then back in my to prepare for the reason to of gone up to London in the first place

4 Comments
I had a Great Day (Well An Hour Or So Anyway)
Posted:Mar 3, 2024 3:05 am
Last Updated:Apr 11, 2024 5:03 pm
2481 Views
I have been suffering with a severe LODT recently. After the summer that meant that I had many many hours of wearing any of my finer things it's now back to the slow time.

I wanted to try on one of my favourite on my favourite dresses while wearing my waist cicnher to try and improve my shape, I have issues currently with the flexibility of one of my shoulders.

The first bit of fun was reaching behind my back to tie the laces (Could be a lot easier with a friend) When I pull it taught I can not tie it up around my back luckily the laces (just) reach around the front. I had to use a spoon as a clip, it might not be practical for going out but for 10 minutes at home it'll do.

After mucking about with this for 15 minutes or so it was time to try on the dress. Stepping into it was the easy bit and pulling up my arms was not too bad. I had a very quick shock when I started to pull up the zip in the fact that it just was not going to happen (Sadly).

Oh well since Jo had decided that she was going to have a look at a few items of clothing she decided that she was going to have a little time in something. you might notice the jacket in the top post but the blouse and skirt haven't been together. (when you do not have many things it's difficult to be original)


i also tried on a couple of dresses. One thing that baffles is the way they give out sizes for women's clothes

The first dress is a size 14 and although it's a size smaller than my original dress I wanted to get into this one is roomy.

I Had a comment on another sight about how good this dress looks and and they actually prefer this dress to the one above which sort of surprised me a little. This dress is a lot more roomy and is a size 18. There's noway that this dress is only on size larger than the dress I wanted to get into first (Black FLoral)


The bottom photo is the dress that I wanted to get into the first of all a size 16. Oh well maybe next time OK Alt is doing stupid stuff and (Brown white & Black dress rear view)

Altered the post hopefully sorted





7 Comments
Been A Trying Few Weeks
Posted:Aug 29, 2023 6:46 am
Last Updated:Mar 6, 2024 6:59 am
8236 Views
It's been a trying few weeks in my household with the wonderful good lady having gone back home for a number of weeks and on this occasion sadly Jo hasn't had quite as much time to herself as on her previous trip away.

I have tried to enjoy the time I have had, some better than others, possibly the funniest was when I was fully dressed and a delivery person stopped by with a parcel, I quickly changed and answered the door. Unfortunately I forgot all about the pearl necklace I was wearing.


I was wearing this lovely dress before but as the delivery person is a regular here I really want to keep Jo secret from my good lady


After another delivery which I was looking for, it was time to try these on in a couple of different looks although sadly I thought that the necklace had better go back in it's safe place.


I really wanted to try on this lacy top but due to my manly physic and my unwanted hairy stomach I thought that it's a good idea to wear a shirt/blouse under it.

The observant of you will realise that I've had to wear a shirt of Joe's own due to the fact that Jo's blouse has been placed into storage and I didn't the time to rescue it from it's storage place and return it in the available time, some times you do just have to give in.


9 Comments
Jo's Last Trip Out For A While
Posted:Jun 9, 2023 8:38 am
Last Updated:Nov 23, 2023 11:27 pm
11274 Views
The other day Jo went for a drive and was rather pissed off by the whole experience of her day.

It was far windier than I was expecting and finally she had the wind through her hair experience that I had not experienced in years a thing many men like myself are so used to (it started going in my early 20's)

To start with I found out that I had broken one of my earrings when I was removing them last time I wore them, not the biggest problems but just wish I had had time to try and repair them at home.

Then when I started walking around my hair was flying everywhere and in my mouth. Now like most ladies I had already made the effort to use a hairband to keep it under control.

My plan was to spend about an hour walking around but after 10 minutes I had had enough, now obviously I had to have at least another 10 minutes to get back to the car and took a slightly different route to get back there as I wanted to stay out of the wind too!

another thing I found out was that whilst wearing my waist cincher my skirt slid down a little further and my blouse kept coming out of the top of the skirt. If I went with my normal stomach t would not of been a problem or plan b not done it up so tight that might of worked too but I really wanted a smaller stomach.

Anyway the view of Portland was worth the effort and maybe my friend on another site could of helped Jo out with re tying my cincher better.

Anyway once I found somewhere out of sight I even went to the trouble of removing my wig and trying to get it under some sort of control which failed so I trudged back to my car and drove home pissed off.



Oh on another note I did invest in some shoes that looked great. Now with this purchase I was only possibly going to wear them once or twice before I threw them out to any charity bin that was handy so that is what happened to the items in the photo above. They were an impulse Ebay purchase and 6 inch heels are hard for girls like us to hide form the other half and I'm 6ft 2 to begin with too!

Sorry for my ramblings Jo xx


8 Comments
New Dress Needed An Outing
Posted:May 26, 2023 9:17 am
Last Updated:Aug 22, 2023 6:25 am
11998 Views
I do not get to go out all that often and the other evening Jo thought that her new dress needed to be worn out of the house for a while.

The weather was gorgeous and after getting away from my front door it was off with the Brad male clothes and on with her wig, earrings and shoes.

One of my toes decided the other dat that my shoes were rubbing it the wrong way and I took care of that before leaving home. I wish that I had taken the same precautions with my other little toe, it was not happy when the shoes came off.

I had quite a wardrobe malfunction as my waist cincher was coming undone the longer I wore it, from the bottom which sort of ruined the hour glass figure this girl was trying to do. It was the knot on the lace from the manufacturer but all the same and not my own efforts. I was really surprised that it didn't end up tripping me up when it fell around my ankles as I was walking by the water.

Then just before bed I tried on my favourite dress after I had the zip repaired as I've ad to hide this for quite some time from it's real owner. Anybody willing to finish doing my rear zip up?

More to come




7 Comments
New Dress Needed An Outing
Posted:May 26, 2023 8:17 am
Last Updated:May 26, 2023 11:11 pm
12076 Views

I do not get to go out all that often and the other evening Jo thought that her new dress needed to be worn out of the house for a while.

The weather was gorgeous and after getting away from my front door it was off with the Brad male clothes and on with her wig, earrings and shoes.

One of my toes decided the other dat that my shoes were rubbing it the wrong way and I took care of that before leaving home. I wish that I had taken the same precautions with my other little toe, it was not happy when the shoes came off.

I had quite a wardrobe malfunction as my waist cincher was coming undone the longer I wore it from the bottom. It was the knot on the lace from the manufacturer but all the same.

More to come
2 Comments
Bad News, Good News
Posted:May 10, 2023 6:42 am
Last Updated:May 26, 2023 2:42 am
12343 Views
I get home.If you get too this before I get to post my photo's please cum back again

I am home alone for the next month (other when the home help is present)

My good lady has had some bad news at home and has had to leave Jo to her own devices for 30 bays before I go on my travels to join her.

The Month of Jo obviously started poorly as I had to deposit my good lady at the airport at stupid O'clock in the morning, once this had been completed it was time for operation Jo to start.




So before leaving the airport I change into one of my skirts, pink sweater, panties well you know what us girls wear so I'll forgo the rest and say that I let Jo do the driving home.

I stop off at the service station on the motorway before diverting a little for fuel as I am not paying those legalized highway robber for their gas! after that it's a quick trip to a shop so that I can get something to drink before heading home again


before stopping to view the wildlife in the forest before having to change out of everything when I get home.



After a few hours I decided that everything needed to be given a good wash which meant that Jo got to try on even more items either before or after including my red sequin dress.

Bad news means that a lot of the time Jo is home alone and she has had the opportunity of wearing a number of items being worn around the house for hours on end even sleeping in my babydoll.



More of Jo's tails to cum over time will try and get the photo's added really soon but no promises
8 Comments
Jo Had Some Alone Time
Posted:Mar 21, 2023 12:42 pm
Last Updated:Jan 9, 2024 11:11 pm
15531 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

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