Adventures in Crossdressing: Work Colleagues

I took two days off from my day job this week. Frankly I needed a small break after a rather busy few weeks and I also hadn’t had much chance to just be me recently, so I out in two days leave and asked my spouse to keep at least one day free. It turned out Monday was our free day as she had a consultation booked on the Tuesday already.

It is winter here and I am feeling the cold particularly badly this year, although in objective terms it has been mild.  I have therefore been looking for some slightly warmer pajamas. I had looked in the men’s department of a few stores and had not found anything I liked. My spouse had bought herself a pair of very nice (not too thick) polar fleece pajamas and she suggested I should get myself a pair. So it was decided, we would do some (practical-ish) clothing shopping!

We got up early on Monday morning, made breakfast and got the girls ready for school. My spouse took them to school and I tidied up the house and jumped into the shower and shaved. We got dressed together and did makeup. I wore a pair of skinny blue jeans (jeggings?) a grey polar neck sweater and grey ankle boots. For once I did not bother with nails or even any bling. Those who know me, don’t worry, I am quite alright, I haven’t lost my mojo, I just felt like being a little less fussy, that is all. After getting ready we had a few minutes to spare before the shops opened so we even had time for a few outdoor photographs. They say a picture is worth a thousand words, so here’s four thousand words for you:

After taking the pictures we left for Cresta Mall, a short drive from home. We made a bee line for Woolworths, which is where the pajamas I wanted were on sale. We found a number of lovely sets of pajamas. What colours to get? I decided that as these were to be worn as ‘everyday’ winter pajamas, they needed to pass muster and could not be too feminine. That meant anything with bows, pink etc was out of the question. I found a very nice set that had mid-blue bottoms with light blue star decorations and a light blue top. I took these in a medium. This proved to be a good size for the bottoms, but my shoulders are a bit wide for the top, so I went a few days later and bought a second pair in burgundy (the bottoms) and a pinky beige (the top and star decorations) in large. The bottoms are a little too big around the waist, but the top is better… Woe is me!

When paying for the pajamas the teller addressed me as “ma’am” which is always nice. I made a mistake entering my PIN on my credit card so I had to re-enter it and that meant some additional, non-scripted conversation ‘on the fly’ to explain the problem. This is always tricky as it is very easy to revert to your deep, gruff male voice. I don’t know if I did or didn’t, because the teller handles it with aplomb. No second takes, no stumbling. She just kept referring to me using female pronouns and honorifics. So that was good…

After buying the pajamas we decided we would go and get some tea and cake at a patisserie in the mall. But first I wanted to take a closer look at some denim jackets I had seen at Milady’s on the way to Woolworths. We were on our way when my spouse greeted someone I had not noticed coming towards us. She greeted my spouse back… I looked across (I had been window shopping) and DISASTER it was one of my spouses former work colleagues (she stopped teaching at the end of last year to run Priscilla’s Services full time). Why was she there? This was a Monday morning. At the mall. She should have been at school. Teaching. I didn’t hang around to find out. This person is friends with male me on Facebook, has been to my house a few times, I have been to her birthday parties etc. But she knows nothing about Daniella. If I spoke to her I was done for. So I just breezed on by as if I was just walking along doing my thing. This may have appeared suspicious or rude, but I doubt she even noticed.

After a few minutes ambling around my spouse and I met up again. It seems I was not even noticed and not a word was said about the rather rude and tall friend accompanying my spouse… RELIEF. It turns out her school had closed two weeks earlier than the rest. Who knew? Anyway it seems she didn’t notice, let alone recognise me and that was a very good thing.

We went to Chateau Gateaux for mid morning tea. I had a lemon and granadilla tartlet with a cappuccino, my spouse had a chocolate volcano and a hot chocolate. The cakes looked divine. They looked better than they tasted, but they were by no means ‘bad’. I believe they were not as fresh as they could have been, given that we were there on a Monday morning I suppose this is to be expected.

After our little decadence we returned home, I changed and we went to collect the girls from school.

This little adventure just goes to show, even when things go wrong and you bump into people you know, you are unlikely to be recognised. I had fun and I got some new pajamas and a piece of cake. I would call that a success!
Priscilla’s Services for all your crossdressing requirements: storage, makeup, personal shopper and accommodation/a place to dress.

If you too want to get out and about dressed en femme, or just want to be the most feminine version of you that you can be in the privacy of a studio apartment, why not look up Priscilla’s Services and have a few hours of safe, discreet fun.




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  1. You look fabulous! I do love your blog! Just wanna share that there’s also a pair of wearable silicone huge boobies from FakeABaby that you might want to check out. Highly commended by a good friend of mine. I’m using them now and they’re gorgeous! Looking forward to more posts from you. Kind regards!

    Liked by 1 person

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Daniella's Ramblings

Transgender People. Women. Society. Reviews and Much More

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Nicole Higginbotham-Hogue

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