Tag Archives: dressing up

Doubt sets in

I have felt a little bit lost of late, creatively speaking. Musically I feel spent and somewhat abandoned. Solace seems to be coming from my Secret Poet project which excites me but deep down I know it is not the ideal way forward. Thinking I could fit in with the cabaret set was perhaps a misguided notion. Sure I am capable of a certain degree of glamour but my act isn’t even a proper act and it’s entertainment value or wow factor is perhaps non-existent. This became clear to me as I took to the stage as Anna for the first time. As fun as it was I always tend to be my harshest critic and like with my music performances I believe I may have been the least interesting item on the menu. I’m not sure how I can enliven it as jokes and banter are not especially easy for me. I did consider early on in the planning process that I could end on a song. Be it an extremely random cover version or some funny little ditty I have yet to compose. Having spoken with my wife and another friend I’ve came to realise that I rushed my performance. That’s normal I guess – I always remember the very first gig I did with my band when I was 17. We did our half hour set in 20 mins!

I have another week to prepare for it and at least this time I have more poems to choose from so I can be picky. I wish I had more like ‘Stuck in a dress’. It was pointed out to me that that is my pivotal work ie the one that goes the best with my image. I’m a guy getting stuck in a dress and isn’t it usually women who get stuck in dresses…oh the hilarity. Most of the other poems could be told without the hair and make-up as my normal self but not that one. I should think about it more over the next while.

I’m really looking forward to the gig as it’ll be a chance to hang out as Anna in a cool place with arty and open-minded people. In the back of my mind I’m also planning to get to take some pictures (posed of course) whilst there. Sick of taking the same pictures in the house so the Art School should provide a good opportunity for that. I took some new photos last weekend actually and some of them were rather good. Here they are below, the red dress and the blue dress are new purchases. Both from charity shops – I can’t resist a bargain 🙂

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These outfits are older but I was able to still find ways of enjoying them. For this part of the session I donned a trusty waist cincher and hip padding to lend a more feminine shape. It’s required especially for the sake of the bodycon dress which just goes up and down on my manly frame.

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Look what the cabaret dragged in!

So I actually did it! Last Friday I took to the stage and dramatically recited some poetry Anna-style. Filled with excitement and a little bit of terror it was all over in a flash…and then I got changed and we went home.

In my plans the previous week I had decided to get changed in work and walk to the venue which I estimated to be around 20-25 minutes away. It’s a cafe so it doesn’t have a backstage so reportedly the performers fight over the disabled toilet. (Funnily when I did get changed to go home there were remnants of the burlesque dancers strewn around; glitter and boa feathers. A colourful restroom indeed). And this I did! Echoes of the last night out reverberated in my mind only this time my confidence was a few notches higher. I spent less time getting ready than that previous ocassion, about 45 minutes. I had chosen the toilet nearest the exit I was intending to use and before leaving I slipped into my comfy ankle boots – well I wasn’t going to wear my good red pumps en route. Especially as it was bloody raining. Luckily I had my umbrella.

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The walk was very exciting as at the last minute my intended route changed. I was going to go a back way that would exchange a main road for something quieter but I thought what the hell! My umbrella would protect me. By the time I got to the Rio Cafe I must have looked a state. My eyeliner was running and I was rather warm but I soon climatised. My wife and her friend were already there and must have got a wee shock at coming face to face with the mad poet so soon. We had dinner and drinks and talked whilst many other folk arrived. I was really chuffed to see several friends turning up including my sister and her man. I think my set itself went well, there was applause and some laughter (which was intentional on my part). The ‘Stuck in a Dress’ poem went down the best I think. I could have done more but the well was dry and I dismounted the stage in a daze. One of my friends is a photographer and documented some of the proceedings. I had hoped to include some but haven’t seen them yet so I may include them in the next post. Here are a small selection – the lighting wasn’t very good sadly…

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Someone we know also did some HD filming and uploaded a compilation of the night to Youtube which you can view from here…

I can’t wait to do it all again! I’ve been working on some more material and working out what else I can wear. I reckon I’ll use different hair next time too – something that frames the face better. There’s no sign of another gig yet but I’m working on it. I had such a close shave that I took the opportunity to do some make-up practice the next morning. That’s my excuse and I’m sticking to it! I want to master liquid eyeliner you see, does it look okay?

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Thursday Morning Dress Up

Sometimes I wish I could write something a bit more meaningful than this. I got the chance to dress up today for a few relaxed hours and I had a really nice time. Simple stuff. No new outfits as it wasn’t pre-planned though I did get a new dark brown wig with a fringe the other day. Impulse buy, it was relatively cheap. So I dug into the wardrobe and pulled out a few old skirts I haven’t worn in ages and some tops to match.

The black skirt I’ve had for ages and the
houndstooth top is one of my favourites though it does make my boobs look a bit too big!

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The black top and grey skirt are old ones too. Rather tight fitting!

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I am liking the new wig though – it is rather tight though and hard to know if I have it on right. It’s also a bit darker than I would normally go.

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Hope you’ve all had a lovely Thursday! Let the clean-up operation begin (sighs)…

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Anna xxx

Raiders of the Lost Pics

Recently I discovered that my old MySpace is still there. I have no way of deactivating it as I no longer have access to the e-mail address I set it up with. It had been quietly sitting there gathering virtual dust all this time. I’m guessing it was around 2010 since I last logged in, the time of the last purge. Familiar faces greeted me from my Friends list but all posts and comments appear to have disappeared. I wonder what all those people are up to now and if they’ve abandoned their profiles for dead too. The reason I logged on was to have a look at some of my old pictures to see if they were still there. Indeed they were. I no longer have copies of them you see, having been overly careful down the years I would delete pics off the hard drive once I’d uploaded them. An idea I have been thinking over for some time is to sort out my Anna photo archive properly. From 2011 onwards I have a pretty comprehensive collection but the years prior to that are decidedly patchy. I had thought of maybe starting a Flickr account too. So I have somewhere to keep a back up but also have them on display for anyone who would appreciate them.

As often happens when you start looking at old photos I was transported back in time and thus lost track of it. I copied a fair few of them – not all though only the ones that looked okay. Some of them I had forgotten about and I cringed at some of the outfits and poses…

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I began to think again about why as crossdressers we photograph ourselves as we inevitably don’t get to share them much (god bless the internet). I suppose it’s not too odd because really as people we photograph everything we see, especially these days. We like to chart the progression of our lives and we like to remember. I’m particularly pleased with my archive, it’s pretty much a decade’s worth.

Pictures can also be incredibly powerful, funny, moving, thought-provoking and obtuse. Sometimes all at once. I happen to think the best ones are not always posed. I really like the pictures where the subject(s) are not necessarily aware that they are being photographed. No one else has ever taken a photo of Anna and I think I’d really like that. It would be terribly interesting to see how that would turn out. I’ve often wanted to ask my wife but have been too shy. When we did the now traditional Halloween Anna evening last night I wanted to ask but couldn’t find the right opportunity. I suppose I’m also a bit worried because when we were discussing my last post she remarked how I seemed to default to ‘sex kitten’ in them. It was a good point but that’s probably just because o my wardrobe choices. Put me in a cute skirt and heels I automatically bend or point my knees and turn my head to one side. I can’t help it 😄

I did take a few pictures before we settled down to watch a film. Ended up in that green dress I bought a couple of months back and I even accessorised!

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Hope you all had a great Halloween too! If I sort a Flickr out I’ll let you know X

New Green Dress(es)

Hello there! Hope you are all well 🙂

Things have been getting pretty busy for myself in recent weeks. We’re getting ready to move house and I seem to be having a gig explosion which means I’ve had to rehearse for them. I’m terrible at remembering lyrics but the potential audience’s unfamiliarity with my stuff could see me getting away with it. I also seem to be getting a lot of offers of musical collaboration but we’ll see what happens with them. With all this in mind I forewent a rehearsal on Tuesday to get all dolled up for the last time in this current house (hopefully I’ll get a chance at Halloween!).

I had some new purchases from a few weeks ago to finally experience in context, ie wig and full make-up. First off was this purple skirt which I got from 99p in a charity shop. Sadly the lighting doesn’t really show it properly. It was from Etam (remember them) so I guess that means it’s vintage now lol.

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The second item I’m rather fond of, a rare example of me paying full price for something from Primark. It’s an adorable green plaid dress with a peter pan collar and zip detail.

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The last one I enjoyed the most, it was only £2.75 from a charity shop. I paid an extra £1.50 for an emerald stone necklace but frustratingly can’t seem to unentangle it. I needn’t have bothered as it looks fine without it. I took quite a few pics with this so….here we go!

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This could definitely be the dress I wear if I have another night out any time soon. Hell this could be the impetus for one!

Before I packed it all away I decided to experiment with my corset and some hip pads to create the illusion of waist. It certainly looked and felt good but sadly doesn’t come across properly in the photos as the lighting got poorer.

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Have a lovely weekend! I’ll be venturing into cupboards discovering long forgotten artefacts “oh look – it’s the sandwich toaster” etc…

X

Mid-Week Dress Up Joy

I always wish I had more important or exciting things to write about. As it is though I cannot fully express the joy and excitement of a mid-week dressing session, especially one that takes place during the day lasting through to the night. I had managed to secure a half-day from work and decided to have a little jaunt round the shops. Aside from important stuff like wine, popcorn etc I was blessed with discovering some bargains. Firstly these 2 dresses both cost 99p from Barnado’s;

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The purple knitted one is very comfy indeed and I must have wore that for quite a while (it has pockets too, I love pockets).

As you can see I also did my legs and chest, a rare event indeed. Haven’t done my legs for about 7 months and it always makes a difference to the outfit not to mention that it ups the femininity factor. All of a sudden the skirts get shorter…

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That last skirt is one of my favourites, it managed to survive the last purge. It’s just so ridiculously short. I know it doesn’t really go with stockings but I don’t care!

The other bargain I secured was in Primark where I found a pair of nude heels for £3 in the sale. Upon taking them to the counter I ended up in a bit of banter with the assistant. She didn’t really think they were my style and I told her that I had an outfit that would go swell with them (a lie) so stop being so presumptuous. When the shoes scanned they showed up as £1! I could have done a wee dance but I restrained myself and expressed pleasant surprise. There’s a little ankle strap on them that I considered cutting off but actually it looks okay on.

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…my favourite view, I cannot lie!

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Mostly I lounged around – though I did put a washing on, hoover and do the dishes so I’m not a totally lazy bitch. I like to try and make the most of this time. That’s why I never just wear one outfit and I’m assuming other cds are the same. There was a dress I got my wife for Christmas years ago that she has relinquished to me that I rather liked, I tried that out to. It was from Joe Browns so it wasn’t exactly cheap.

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Finally what turned out to be the biggest surprise was a red dress I bought to wear at a Christmas gig last year*. I had never worn it with make-up and a wig before but I thought I’d give it a go because I was considering getting rid of it.

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I’ve changed my mind as you can imagine.

Before I go here’s a shot of my new ridiculous shoes on. I’m still not used to them yet as they are a bit big for me and I have to stuff them at the back so they don’t fall off!

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*I wear a dress and heels on stage with my band but I don’t go all the way. I get too warm on stage in normal attire so a full transformation would be out of the question.

Anna’s Alive!

So I survived intact after a night out as Anna. I’m not sure how to write about it but I do know I should keep it brief and vaguely interesting. I have read accounts of other people’s nights out and some have a tendency to overshare, delving into the minutae in excruciating detail.

This is how I looked after around 75 minutes of scrambling around in a work toilet…

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I think having someone else with me helped a great deal, the only real terror came when exiting the toilet and stepping out the main door. It was so damned windy and my hair immediately went to pot. I met my friend and we walked to the train station. On the way I was read by a couple of passing girls who screeched with what I can only assume was glee “tranneeee!”. That did make me chuckle. From then on though I was oblivious to any other such attention. In fact I feel I should thank everyone I came into contact with that night for not batting their eyelids and treating me as normal. Basically I just had to go for it and interact with people and it paid off. Having never really given Anna’s voice any thought prior to this, I thought it best to just speak a bit softer without being over the top scaling octaves like a mad man. It seemed to work.

We only had between 6 and 10pm to work with so we went to 2 places. First we had food at a place called ‘The Living Room’ and it was really nice and friendly. The waitress impressed me no end by asking ‘us ladies’ if we wanted a drink while we waited. Whilst there I also got to visit the Ladies Bathroom which has always been a mysterious place for me. I fixed my hair and make-up and a couple of other girls were taking selfies.

The next venue was a bar in the Merchant City of Glasgow called ‘The Riding Room’. Now this is defintely a place I’ll return to, in fact me and my friend are discussing the possibilities of this. I’ll try not to get too excited just incase. This was my first opportunity to go to the bar and I think I did alright. The barman even called me darling. In fact my friend was certain he was checking me out! Whilst there my boobs came a little undone so I had to visit the bathroom again to fix them – damn! On the way back up the stairs (for the toilets were downstairs) a man held the door open for me and said “after you hen” which quickly became another highlight. It was indeed sad to leave, though it could have got awkward as the place started to fill up with people and a couple of them I actually knew from the gig circuit. I curse myself now for not going over to say hello as they are arty types who would probably have appreciated the effort that went into such a transformation. Well that’s what I’m telling myself 😉

Back to the station we trudged. I got my man bag from Left Luggage and we popped to the toilets so I could change. Funnily enough I got shouted at while I was at the mirrors by an attendant. “You’re not supposed to be in here” he said, but I assured him I was a woman 5 minutes ago and he didn’t have a problem then!

I had the luxury of an empty house when I got home so I decided to make the most of it and got dressed again (what am I like?).

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Really glad I went out and I can’t wait to do it all again and hopefully with a bigger crowd (and for longer). I feel so blessed that I have great friends that are more than happy to go along with my tranny tendencies, I wish everyone had that.

No Ordinary Debutante

With Anna’s social debut only weeks away the proper planning kicks in. For an average night out I hardly have to pre-think at all – well I am a man! An outfit, such as it is, will be picked at almost the last minute. This man outfit will most likely be a shirt and a coloured jeans combo which I have favoured in recent years. With Anna I feel I’m starting from scratch. Though I have to try hard to resist the temptation to buy loads of new things. Theoretically I don’t need a new jacket but I am keeping an eye out for one, preferably a black one that isn’t too long. The two jackets I have already both have their flaws, the hooded one particularly. Sadly that comfy number is cursed with sleeves that are a little short (or are my arms too long?). The long green one is fine but it’s £5 price tag was the chief motivation behind its purchase.

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I never envisaged going out for a prolonged period of time else I would have invested a little more thought into their purchase. As for what I’m wearing beneath the jacket, that is easier. From when the idea of a night out was first mooted I instantly thought of my long red houndtooth dress paired with black ankle boots. More or less the outfit I donned on my last expedition outside. In the last week I have been stocking up on some accessories plus I bought a purse and a bag (both from a charity shop). Also, my thoughts have turned for the first time to earrings. Not having pierced ears they never really occurred to me before. Bless you clip ons! I couldn’t decide between hoops or red diamante drop ones so I got both. They were both off of eBay and were relatively inexpensive. I also purchased some rings, a new scarf and something pretty to wear on my wrist. Did I forget to mention that I got a new wig as well? My brown one has been in faithful service for nearly four years now and up close does not look too healthy so replacing it had been on the cards for a while anyway. The plastic hooks that control the tightness disintegrated some time ago and it’s being held together by paperclips!

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Where should we end up? It will be after work and indeed it is with two female friends from work who shall be accompanying me. Eating may very well be cheating but it will be for the best – I don’t want to be sick over my lovely dress (or over them!). Initially I had wanted to go to a t-friendly bar/restaurant, but most of the ones I checked out were fully booked on the night in question. Looks like it has to be a normal bar/restaurant – a baptism of fire (well no actually, the whole first hour after coming out of the toilets will be the baptism of fire). Booking the table under my female name made me chuckle. Afterwards I’m hoping to end up in an area of Glasgow called the Merchant City which has several LGBT pubs/bars/clubs. There is one in particular I’d like to end up in as I hear their cocktails are spectacular.

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Of course the issue of changing and commuting to town was put in place early on to enable the plan to built upon it. I shall change in work, bag up my man stuff and all three of us hop on a train for fpur stops. My man stuff will be deposited in Left Luggage for approx 4 hours and I aim to change for the journey home. At this point I must confess that I have not told my wife. There are still three things she doesn’t know and one of them is my occasional trips to the outside world. I do often consider imparting these last remaining secrets but then think better of it. It’s almost like I enjoy still keeping some of it for myself but also I know it could ruin things as they are. We have reached a rather comfortable stage I think, one in which we can have casual discussions about a skirt or she’ll recommend a foundation to me. I just need to be very careful but I always have been 🙂

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See me shiver with antici……pation

I am filled with inexpressable joy. It turns out that I have a chance to dress again really soon. Must have been a month or two since the last time – so long I can’t remember exactly when. What I do remember is that it was only for a couple of hours one evening. This next dress date promises an empty house for just under 24 hours. A rarity indeed! As a result I have a half day booked off work and even plan to celebrate with the now annual event of removing the leg hair as well as the chest hair (low cut tops here I come). I’ve also found myself quietly planning outfits – I have some new ones you see. Some tops and a skirt from a ‘Christmas shopping trip’ I made with a friend from work. Recently I have also come into possession of a couple of dresses from one of my wife’s friends.They are both size 16’s so they are too big for my wife and there is something appealing about them I can’t explain. I wouldn’t have purchased them if I’d seen them in a shop but then I probably miss a lot when I’m browsing. I’m still a nervous soul deep down and my shopping style is perhaps a little furtive at times. The other reason that I’m pre-planning is that I would like to try having another little clearout. I know I have some things that still aren’t part of a definitive outfit so they have to go. Of course I’m saying that now but there are some things like a few of my skirts that I keep saying I’ll get rid of but don’t because I really like them regardless.

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These days I have been selling my unwanted stuff on eBay so it means I can get a bit of cash from things like dresses, tops and even a couple of my old wigs. Though I mainly sell non-girly things like CDs, DVDs, books – I even sold a clock recently. I admit I can’t often find it in my heart to be ruthless when it comes to clothes and shoes. Even with ones that are holey and busted. Some of the band t-shirts I’ve kept hold of down through the years are in an unspeakably abominable state. Shoes as well, ones that are really worn down and holey – I tend to keep them for the summer months. The dry season.

Speaking of busted shoes and an extended dress date, both of these factors have previously met, or should I say collided in an unfortunate fashion. In January last year I’d treated myself to a pair of black knee high boots with a cuban heel. Finding decent cheap boots was tricky last year as my usual outlets had forsaken the heel. They were all selling perfectly decent boots but with no elevation. There needs to be a heel or I’m not interested. I managed to find a pair that met both standards of height and size (accomadating my biggish feet) for £10 in the sale at Primark. Trying them on at home, they fitted fine so I removed the tags and tossed the receipt. A week or so later when giving them their first proper outing, the zip on the right boot came apart in my hand. I was furious. That basically ruined my night though I sought to repair it as best I could. The wonder that is super glue eventually solved this problem. Luckily they both slip on alright without engaging the zip, especially when wearing hoes.

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As well as planning outfits I also plan to just try and enjoy it while it lasts, even see if I can stay in character (such as it is) throughout – except when sleeping, that’s just silly! In the past I have managed around 6-8 hours in the evening on average. Sometimes there’s even a little overspill into the morning when I wake up. I’m looking forward to waking up with smooth legs. I only repeat it in the morning though if I know there’s time to do it and tidy up. Not that I’m really messy or anything you understand but just incase I’ve left something lying out. That’s a remnant of the past right there, a sign of my diligence. I was never caught out but came pretty close on a few occasions. I avoided it with stupendous luck that one time I became locked out. One other time I had left a box of my wife’s make-up out that I had been using. It was one that she didn’t really use much so she was confused as to why it was sitting on the bed. I hastily explained that I was tidying up under the bed and I had left it out to see if she still wanted it. She did want to keep them as it happens so back under the bed it went. In recent years such situations have more humourous potential. For instance, if I put any of Anna’s stuff in for a wash it can sometimes cause mild confusion. Black tights for instance did just that a few months ago. When we were sorting through all the dry washing separating it into bundles I noticed my tights (the only pair in the wash as it happens) going into my wife’s pile. I raised a polite objection and after a brief tete a tete she conceded I was right and we laughed about the absurdity of it.

I hope to post again soon and share any pics or stories from my dress date…providing of course they’re worth sharing

Dresses vs Guitars

The common code I use with friends when I’ve recently been dressing is that I had a visitor the other night. Although I suppose this implies a whole other person replete with uniquely different personality and voice etc it’s not strictly true. I change little inside, it’s mostly an external transformation. Years ago I was visited on a regular basis as I had a day off in the middle of the week, still one of my favourite aspects of my time in retail. These days it is more of a struggle as when the opportunity of an empty house arises. The fight between girly time and music commences in earnest. Though I must say that girly time is far more likely to win these days due to the rarity of such chances. There have been times when both co-existed. I can think of a handful of songs I’ve recorded over the years when I’ve been all made-up. I think those songs were probably invested with a little more passion as a consequence. It’s always something I wanted to combine properly at one point – my twin loves of cross-dressing and music. In my current band I have managed a watered down version of this though all I’m missing is a wig and make-up. I will generally wear a dress, tights and heels (sometimes a top hat too!). It’s a memorable image I feel and though it may put some people off I doubt they will forget the band with the dress clad singer. I defend it regularly as a talking point. My wife has come around to it though was for a while anxious as she feared the secret would be out but I’m pretty confident I’ve passed it as exclusively stage attire. I’ll admit though that a few folk who have been let in on the secret recently have gained entry through this but these are people I trust completely.

These are pics I took in July, I haven’t got a post to go with them so thought I’d just slip them in here;

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An opportunity arose a couple of weeks ago for a visit and it was a morning session which is unusual. Previously in the week I had got a half day so I could go shopping, mainly for a new dress as I had a gig on the Saturday. Shopping is usually a rare event also so I made the most of that and went into all the shops I could – charity shops mainly. My gig dress plan is a desire to have a select few dresses only for gigs as at previous shows I’ve worn some that I really like. So I came to a decision that I want some I care less about to wear at such events. I found one on sale at Asda for £5. It was a 14 but I won’t be wearing bosoms with it so I can just get away with it (it is a small fight to don and remove). In Barnado’s, a local charity shop, I spied a nice top and a dress that would not look out of place on Kim Kardashian – 99p each. The top doesn’t fit so I gave it to my wife and the dress kind of does fit but I can’t zip it up. I can’t explain why I was drawn to it as it’s not my usual style but it intrigued me. I made sure I at least snapped a couple of pics of me wearing it. Interestingly my wife also took that item. She was trying on some dresses a few days later and I showed it to her. She too was drawn to it and was initially shocked as to how short it was on her but I pointed out that she looked incredibly hot. I neglected to add how erotic I found it that she was wearing something that was mine and was making it look good. Obviously it was actually made for a woman so it would look much better draped around the correct body shape. When I wore it I was trying out my new corset/waist cincher and control pants with hip pads so I was giving it a good attempt. I admit I was taken aback when I seen myself in the mirror – I’ve never achieved that shape before and I was most pleased. I had a waist!

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In the few hours I had that morning I didn’t wear as many things as I normally would. I decided I would wear 2 of my least worn wigs (black and long red) and settle on something comfortable but mildly sexy. The mildly sexy part was taken care of with a white satin slip, black hold ups and a burgandy cardigan. Teamed with a long red wig it became most enjoyable. The pictures I was taking ended up taking a saucier turn than usual…

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