Crossdresser Pics

Below are a number of posts where you can find crossdresser pics of me :) I try pretty hard to ensure that they’re high quality, and hopefully you’re able to see how much better I’ve gotten over the years! All of the pictures listed from this page are completely safe for work :)

If you’re looking for crossdressing pictures of a more risqué nature, you can go to this page: *Slightly* NSFW Pics :)

And don’t forget to follow me on Instagram!

(Part of Colours of Las Vegas) I’d gotten pictures of myself in a swimsuit before, but never a bikini. Honestly, I was a bit terrified even buying this because how could it possibly look good? I was glad to be mistaken. This was a good start to the day. It wasn’t a full-on bikini-world, however. A cover-up was necessary because of the obvious reasons. I saw what was down there, it was not a good look. Nevertheless, the cover-up didn’t detract from the outfit at all – it matched really well! Also I’m pretty happy about the fact that I […]

Vegas: Red

 in Crossdresser Pics  tagged crossdresser / crossdresser pics / crossdresser pictures / crossdressing / heels / las vegas / legs / transvestite / vegas by
(Part of Colours of Las Vegas) I almost didn’t buy this dress. I forget why. Even when it arrived, I wasn’t sure how good it would look. After a wash and some drying though, it de-wrinkled enough for me to be pretty sure it would look ok. That, and matched with some converse from the collection, it actually ended up being much cuter than I’d hoped, and photographed really well! Bright colours might be my jam. Given my brownness, bright colours complement my skin pretty well, which is helpful. There’s something very innocent about this outfit. Not sure if it’s […]

Vegas: Yellow

 in Crossdresser Pics  tagged crossdresser / crossdresser pics / crossdresser pictures / crossdressing / heels / las vegas / legs / transvestite / vegas by
(Part of Colours of Las Vegas) I adore this dress. it’s nice and breezy, super flattering, bright and colourful, and for some god-awful reason, I couldn’t get a decent picture of me standing up in it. Maybe I just couldn’t find the right pose. Maybe I was exhausted and couldn’t be bothered anymore. Maybe I was so tired I actually forgot to look at my preparation doc to remember the pose I’d already picked out for this dress. God dammit. In any case, I did get some good photos, so I’m not mad. Holy hell, look at the size of […]

Vegas: Blue

 in Crossdresser Pics  tagged crossdresser / crossdresser pics / crossdresser pictures / crossdressing / heels / las vegas / legs / transvestite / vegas by
3
(Part of Colours of Las Vegas) My wife likes this dress. I also like this dress. However, much like the blue dress, I couldn’t get a good shot of me in it standing up. I look awkward. Which is annoying, because looking in the mirror when I’m wearing it, I thought it looked great! I’m putting this down to a couple of things: The day was wearing on and I was less and less interested in trying a bunch of things. I feel like in hindsight the camera was at the wrong height/angle/distance. The hard part of being your own […]

Vegas: Green

 in Crossdresser Pics  tagged crossdresser / crossdresser pics / crossdresser pictures / dress / heels / legs by
2
(Part of Colours of Las Vegas) See that face? That is a greasy face. That is the face of someone who is currently thinking to themselves “Oh god, is it actually worth being out here in this miserable heat?” The answer to that question is a solid “Maybe”. Daylight was fading though, and getting the most out of the terrace and the limited Las Vegas skyline that I had seemed like an opportunity I shouldn’t miss. All that said, being inside, even with this weird spot-lighting coming from the ceiling, was infinitely preferable. Plus I hadn’t sat on a counter-top […]

Vegas: White

 in Crossdresser Pics  tagged crossdresser / crossdresser pics / crossdresser pictures / crossdressing / heels / las vegas / legs / transvestite / vegas by
(Part of Colours of Las Vegas) I know, it looks black in these pictures, but believe me, it’s really a dark navy-blue dress. And it is amazing. Even with my lack of a waist, it still looks super feminine. Once I figured out the right shoes to go with it, I was incredibly happy with this as a purchase. Once I’d figured out the shoes, I said to my wife “I feel like Kelly Kapoor, The Business Bitch”. If you don’t understand that reference, we may not be friends. To find out what I’m talking about, you should probably go […]

Vegas: Navy

 in Crossdresser Pics  tagged crossdresser / crossdresser pics / crossdresser pictures / dress / heels / legs by
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)

 in Crossdresser Pics / Crossdressing Articles  tagged crossdresser / crossdresser pics / crossdresser pictures / flying / flying pretty / heels / makeup / plane / transvestite / traveling / travelling / tsa / wig / wigs by
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

 in Crossdresser Pics  tagged crossdresser / crossdresser pics / crossdresser pictures / crossdressing / goodpics / lipstick / makeup / Pics / transvestite / wigs by