makeup

1
Work this year was definitely a bit of a struggle – a big hunk of responsibility (with a deadline!) fell into my lap, and so I was deeply focused on making sure it was running on a clean timeline and coordinating with lots of folks. I can’t tell you how many dreams I had about work this year, and how often I had to take melatonin to try and get to sleep. It was an exhausting endeavour, and I was frequently putting in more time than required to make sure things went real smoot. They did! The team was victorious! […]

2025 was rough. Also hormones.

 tagged crossdresser / health / makeup / mental health / patriarchy / transvestite
10
I had a lot of high hopes for this trip. The last trip I went on ended abruptly after I got COVID before I could even dress up – that was ten months ago. I realised in the run-up to my Las Vegas trip in May that I hadn’t actually dressed up since then. A whole ten months. Life tends to get in the way, I suppose. Between getting through six months of constantly being sick from kid-germs, to general life/work stress and scheduling woes, finding the right combination of time/opportunity/energy/willpower to actually get my shit together seemed like such […]

Las Vegas 2023

 tagged crossdresser / crossdresser pics / crossdresser pictures / goodpics / hotel / las vegas / makeup / palazzo / photoshoot / Pics / transgirl / transvestite / Venetian
13
A friend of mine was getting married in Rhode Island, and so our little friend group all flew/drove in from across the country to hang out! I had arrived on Monday, with plans to hang out with everyone all of that week. The wedding was on Saturday, which would give us a day of recovery on Sunday, and then I’d fly back home on Monday. I had picked out a pretty cool outfit for the wedding – a sundress, cardigan if it got cold, hat, shoes. I was ready. I landed on Monday, and we hung out on the beach […]

A Rhode Island Tragedy

 tagged covid / crossdresser pics / crossdressing / heels / makeup / wigs
7
If you’re reading this, you’re probably aware that there’s been a bit of an event going on. Just your run of the mill, minor little GLOBAL FUCKING PANDEMIC THAT UPSET THE FOUNDATIONS OF SOCIETY OMGGGG AHHHHHH HEEELPPPPPP. The last two years have sucked. Sucked enough that it definitely feels like a lot longer than two years. “Two years? Are you sure? I don’t remember having this many grey hairs or neuroses or imaginary friends to function as poor substitutes for in-person interaction oh hi there Sally GET OFF THE CEILING I WON’T TELL YOU AGAIN” Like many people over the […]

Starting from scratch

 tagged crossdresser / makeup / Pics / wigs
3
Las Vegas is only a short flight from San Francisco, and one thing that Vegas has in large supply is cheap hotel rooms. More specifically, cheap hotel rooms that are spacious. And spacious hotel rooms are a lot better for taking photos in because there’s usually more interesting backgrounds to actually take photos with, and there’s also a lot more space to move a camera around in. So far I’ve done a shoot in The Cosmopolitan and a very short shoot in The Linq after flying to vegas while dressed. This time around, we’re hitting up The Flamingo! The thing […]

Vegas: The Flamingo

 tagged barefoot / bra / crossdresser / crossdresser pics / crossdresser pictures / garter / heels / hotel / lasvegas / legs / makeup / sandals / stockings / underwear / vegas / wig
13
Photography is hard. When I’m running around doing my own photoshoots, I’m very much focused on only a few angles and a few poses, while I struggle to figure out what else I can do, and how much originality I can eke out of my limited repertoire. So when I was booking my most recent trip to Las Vegas for my own shoot, I wondered if it would be worth actually paying a professional to take photos of me. The boudoir photoshoot landscape is a bit daunting, particularly because it’s easy to look at those photos, see the stunning women […]

A Boudoir Photoshoot

 tagged boudoir / crossdresser / crossdresser pics / crossdresser pictures / heels / high heels / makeup / photography / photoshoot / sandals / transvestite / transvestite pics / wig
14
One of the things I mentioned in my Crossdressing Goals post earlier this year was that I thought it would cool and entirely terrifying to fly dressed (I believe “Flying Pretty” is the accepted terminology, but i don’t like it. Seems presumptive! I’m not sure I’d personally add “pretty” to the list of adjectives that could’ve described how I ended up looking that day, but so I’ll leave that decidedly in the eye of the beholder). Also mentioned in the Crossdressing Goals post was the fact that over the course of the last few years, I’ve been trying to be […]

Flying Pretty (and a Las Vegas Adventure)

 tagged crossdresser / crossdresser pics / crossdresser pictures / flying / flying pretty / heels / makeup / plane / transvestite / traveling / travelling / tsa / wig / wigs
2
I wanted to do a photoshoot recently. I usually have a theme. Today I did not. Also, I’m tired of doing shoots indoors – I’m going to have to get more out and about, but that requires a car, which I did not have this weekend. Also, where would I change? Outfit 1: Blue tunic, black leggings. Nice and simple :) Oh yeah, and these blue little bootie-things that I can walk in, but I feel like will fall apart and/or cut into my foot at some point. They’re a bit cheapy. Also my ankle bone sticks out (FUN FACT: […]

Lazy Photoshoot

 tagged crossdresser / crossdresser pics / crossdresser pictures / crossdressing / goodpics / lipstick / makeup / Pics / transvestite / wigs
6
I thought it might be interesting to do a study of my own body – the parts I like, and the parts I don’t. I think what’s been most interesting about this is as I grew to accept this part of myself, I’ve also been able to come to terms with the parts of my body that I’ve liked the least. I suppose it’s useful to have an understanding of which are the parts of you that you don’t like so that you can work on them, or figure out how to make them better, or at the very least, […]

A Crossdresser’s body (slightly NSFW)

 tagged bra / chest / crossdresser / crossdresser pics / crossdresser pictures / face / glasses / goodpics / legs / makeup / mouth / nose / panties / Pics / transvestite / underwear / wig / wigs
2
It’s been a busy year. Have I mentioned that yet? I have? Oh ok, I’ll probably shut up about it (at some point). Opportunities to dress have… well, they’ve existed, but having both the time and inclination to do anything about it has been an issue. I had a goal to dress up once a month, or twelve times this year. At last count, I was at nine, so there’s still a way to go. That said, during the last few months of the year, I made some progress on that front. So let’s revisit that. (You might have seen […]

Getting back into the swing of things

 tagged crossdresser / crossdresser pics / crossdresser pictures / crossdressing / formal friday / goodpics / halloween / heels / holiday party / lipstick / makeup / out and about / Pics / public / transvestite / work