Catch-Up #40

 I've been doing a lot of thinking recently related back to my trip to Italy last year. I said I got some dress envy which normally happens but I think that the root of it is not that there were other people wearing dresses but that I wasn't. I was depressed that I was unable how to present how I wanted to. Thinking about it since and there are times when I've looked in the mirror when I've been dressed and I've loved what I'm wearing. It's made me stupidly happy to do it and I realised that through the years I've never felt that way about any male clothes that I've worn. It doesn't matter whether I'm in a t-shirt and jeans or a suit (and to be honest suits and formal wear in general always made me feel a bit uncomfortable) I've never felt that same way and nowhere near as happy as when I'm in a nice dress or skirt and tights. After all these years, it just feels right. 

When I was a teenager I used to go out to clubs with my friends with the chief reason being to pick up girls. This never worked, not for me anyway, I was never that type of person and the music was mostly the kind of rubbish you get in clubs anyway. At least if it had been the songs in the pop charts I might even have been able to have a dance. Genuinely I used to wish I was a woman sitting atop a stool dressed in a slinky red dress and smoking a cigarette like in the movies. No idea why the cigarette (I don't even smoke) or why it should be a red dress (perhaps related to Michelle Pfeiffer in The Fabulous Baker Boys which I've never actually seen to this day or Jessica Rabbit) but I think it was also that I wanted to take on the more traditional female role and have people talk to me rather than having to make the first move. Later on when I started to go out dressed I went to a club with some friends to celebrate a birthday and there I felt like the odd one out but then I thought about it a bit more and figured out that I didn't really want to dress like the other guys in their plaid shirts and shiny shoes but I just wanted to blend in a bit more and not feel like I was a square peg. This feeling has gone away in later years though and I'm more comfortable with myself now and don't feel like I stick out quite so much although some times are more noticeable than others. 

Thinking about it, I don't think that dressing how I wanted would have been the solution to all my problems but perhaps it would have made me a little happier and a bit more at peace with myself without feeling that I'm being forced to act a certain way. It does feel like that at times though, like I'm being forced to look a certain way and I was the one doing it. Perhaps I've repressed that part of me. Maybe that's the reason. That said though I'm still a believer that things happened when they were supposed to and if I had started earlier I may not have been as comfortable with myself. I needed to get through a set of experiences to become who I am now. 

I've been out dressed a few times recently in fact I think last year I was doing it a couple of times a month. I bought some new skirts recently too and even a dress that was a bit too tight (even after I found the side zip) but it was only £1.00. I'm worried that the enjoyment is starting to slip a bit for me but that may be worries about storage. If I see something I like, I will still go for it. 

Lastly, I've had some really nice comments on my writing recently and one in particular I would like to note. I put my Role Exchanger story Office Christmas Party up the The Changing Mirror back in December due to the Christmas theme (in fact it's been about a decade since I wrote it) and had a lovely comment from TF story legend and Role Exchanger creator Morpheus (I have no reason to believe this wasn't genuinely them, by the way) who said that they enjoyed it and it may even have inspired them return to the concept. Genuinely made up by that. 

To end I thought I would add a story I read just last night that I liked about a trio of friends at a music festival who slowly get turned into fans of a pop princess rather than the band they were actually there to see. 

Gaining New Fans by DeviantNabu

Valentines Day 2026

 As ever I've been meaning to put some more posts up recently but I've just not had the time. Today is a Saturday though and Valentine's Day so I thought I would put up a few themed caps based around love and the day itself. 

Chocolate Addict (2013)

This caption was created for Rachel's Haven's February 2013 caption competition which had 'Candy' as a theme. 

Run For Love (2015)

This caption was created for the February 2015 caption contest on Rachel's Haven which had the theme of  'This body is a canvas waiting for you to paint your desires with your sweet kisses, soft touch, and gentle caress...'

Crushed (2021)

This cap was created for Brittany7 over at the Haven and was part of my Love Witch caption offer in which my witchy character Ember offers to assist members with their love lives for fun and profit. This has become a favourite of mine especially with the suggested changes and the Witch Advisor gag. 

A Walk in the Park (2022)

This cap was created for Jeannie over at the Haven and was part of a lesbian themed cap offer I had on at the time. 

The Gender Dysphoria Bible

 I thought I would do a little public service announcement. Now, I don't know why people mainly read this blog and I guess you either like following one man's adventures in crossdressing or you're just here to read stories about guys magically turning into bimbos. Perhaps a combination of the two. Anyway, I recently came across, and spent a while reading, The Gender Dysphoria Bible which can be found online. 

The Gender Dysphoria Bible 

It's a great resource if you're questioning your gender or just looking to find out more about trans people in general. Certainly the piece on sexual dysphoria was interesting to me as it helped make more sense of how I've always viewed women and the "do I want to fuck her or do I want to be her?" conundrum. Anyway, I don't know if me putting a link up will help anyone but I hope it will. 

Stories Stories Stories #2

So far it's not been the best start to the year although I have got myself a couple of new dresses recently and a lovely pink jumper with hearts on that has an Enid from Wednesday vibe. 

Anyway, here are some stories I've been reading recently: 

Frat House Feminization by Sissy Girl Sammi

This is a fun tale set at Halloween as a witch takes revenge on a bunch of frat boys. Anyone who has read my Ember Montoya caps will know how much I like this sort of stuff plus multiple transformations is always fun. I must just mark out one fate, that of Eric who is made transgender. Nothing physically happens to him but mentally he's starting to think about things he never has before. Wonderfully he later sounds out another of the gang regarding crossdressing at Halloween because, hey, everyone does it. Aww, we've all been there, sweetie. Whether or not Erica would become someone who stands up for trans rights or continues on as a rich arsehole trampling all over her trans brothers and sisters remains to be seen. 

Tomboy Trouble by Razmagurk

This one by the ever reliable Razmagurk is for those that love the 'what if girls acted like boys' trope and is also a lot of fun especially how it ends up. 

The Wrong Uniform by Grace Fairway

Always nice to see new stories from Grace especially involving clothes swapping. This one is set in a school and takes place between a teacher and her chavvy student in detention. It was influenced by another story I read for the first time recently Spanking the Teacher by Netsylph which I enjoyed. One for people who enjoy F2F clothes swapping and power swaps

Finally I would just like to mention Evie Hyde's blog Evie's Emporium where Evie has been posting new stories every day so far this year. Great for those who enjoy M2F, F2F, power swaps corruption and especially bitchification. My recent faves include the Fit Bitch universe, De-Gen-Erate, the Role With It universe (which I love playing in), Hate Me Harder and Softening. I'm also honoured to be writing a story with Evie which I'm really enjoying the process of. I have wanted to start doing some longer stuff. 

Christmas Captions #2

 Here's another batch of captions created for the Haven's 12 Caps of Christmas this year. 

My Christmas was fine overall although I'm not too pleased to be back at work so soon. Here's a little tale though, over the last few weeks I went to see a favourite Christmas movie of mine played in a church with a live soundtrack. I was wearing a red maxi skirt, t-shirt, yellow cardigan and a pink coat and I headed to the toilet before the show kicked off. A very nice lady directed me to the ladies - which I did not want to go in for obvious reasons so for a few moments I was staring at the various toilet signs on the wall like I was trying to decipher hieroglyphics until she left. She didn't but she suggested the disabled toilets instead which I duly took somewhat sheepishly. I also posted my Role Exchanger: Office Christmas Party story on The Changing Mirror and it's elicited some nice comments. If anyone is interested this story, which is about 9-10 years old now is elsewhere on the site but anyway captions...

A Hot Girlfriend for Christmas (2025)

My first idea needed a bit more work so I came up with this as a replacement and I quite like it even though I couldn't decide on a TG method and nearly left it as a mystery.

Christmas at the Lodge (2025)

With this one, I was inspired by the picture which just screamed 'bimbo discovering snow' and I worked back from there. 

The Night Before (2025)

I was working on this one for quite a while. The picture is AI generated but it had a storybook look to it so I tried writing some poetry and parodying Clement Clarke-Moore's classic 1823 poem A Visit from St. Nicholas. 

The Email Request

As always there are a number of things I've been wanting to post about especially before I forget it all but for this post I thought I would just mention an email received at my work a few days ago which took me back to the old days reading about sissy stuff. If you're reading this I expect it's a route you may have gone down as well. Crossdressers look for any excuse to dress up and make it not look like it's exactly what we wanted to do. 

Anyway, this email came from a man who I'll call Billy (not his real name). Billy informed us that he had just lost a bet (haven't we all?) and now had to dress up as a woman and work at a local business for a few days (for nothing). We would get to pick his outfit and if we wanted him to attend an interview in drag then he would be willing. No idea what this mysterious bet was but good on him for trying it. Hell, if he's able to find a place you can work in drag I'm willing to try it out. 

Reading the email took me back to reading about crossdressers experiences go out and also the self challenges that people may do such as going into shops asking to try on wedding dresses or lingerie although I think to do that you may have a bit of a humiliation fetish. Certainly I've written enough caps in my time dealing with lost bets. I haven't passed on the email so I doubt I would be able to give poor Billy a chance although I just imagine if I did it would be the best day of his life. 

Halloween 2025

 I've been meaning to update this for a while now, adding what I've been doing and even a few story recommends but time just got away from me. I was also going to, due to it being spooky season, do a quick bit of flash fiction but even that I've struggled with so here is a double header of caps featuring monster based weirdness from 2014. These were created for the Rachel's Haven October Caption Contest with the theme of 'You are the Thing Demons are Afraid of'. Looking back, I quite like these two and in a lot of ways they sum up my style and humour. 

Enjoy and Happy Halloween! 

Invasion (2014)

Demon Rising (2014)