Wedding Dress

About 10 years ago I found a lovely wedding dress in my size.  It was in an heavy ivory dupion silk, satin lined, tea length with a huge full skirt and masses of net petticoats to puff it out.  The bodice was heavily boned with a sweetheart neckline and thick straps with bows on them.  On the back was a super sized bow.  I think it was from the early to mid 90's.  It rustled like nothing else!  Super femme.

These pictures give you a kind of idea of the shape of the dress how the shoulders looked!

I kept it in a cupboard at my desk in the office as I was often working late and sometimes had the opportunity to dress up in it when everyone was gone for the night.  I had some ivory bridal shoes, some matching satin gloves and a little veil.  Awesome 

Once, as I was all dressed up, the cleaners came in (I thought they had already been!) and I had to rush out of a back door and hide outside until they had gone.  Man that was awkward! Especially as the backdoor led out to a communal area shared by many offices - lucky it was late autumn and dark and there was none there.  The problem was the door only opened from the inside and I had to walk right around the building to get back in - not being quite sure if they had left or not.  Luckily, they were only 10 minutes and I saw their van pulling away.  

This gave me an idea though.

What if I could put myself in some kind of predicament in the office - a deliberate risky dress-up?

It took me a while and a few goes to get this right.  I didn't want to get caught at work as that would be a disaster, but I did want to be placed in a terrible dilemma whilst dressed up.  

I finally worked it out.

I have some handcuffs and leg irons that I could connect with a chain and a collar that can lock with a couple of heart shaped padlocks.  If I left the keys to these outside in the shared communal area during the day, I could have some fun!

To make the problem somewhat more interesting, if I could be dressed in the office before everyone left, that would make my job that much harder.

We had a server room in the office that none else went into.  It was small, dark and I had the key.  What if I could lock myself in there undetected, with everyone thinking I had gone home, dress up and lock on the cuffs.  That's mental!

So thats exactly what I did.

I left the keys at the most public end of the outdoor area at lunch.
I also left some keys to another padlock in my car.

I had a leather knee length skirt, some knee boots with killer heels and a pink knitted jumper locked in my desk cupboard.  They key to the cupboard - outside with the handcuff keys!

I would need to retrieve these to get the other clothes so I could get to my car to get the key to my male clothes!  Madness!

At about 4:30 I went to 'leave'.  Taking the bags with my dress and stuff in, I stashed them into the server room when everyone was busy and not looking.  Now, all I had to do was go in, lock the door from the inside, strip off, dress up, and wait.  And a long wait at that.  It didn't get dark till 7 and I had no idea when my colleagues would leave.  20 people in the office, holding me prisoner and they had no idea.

Quietly locking the server room door, I turned off the light and stripped off.  Before I could chicken out, I threaded a chain through my male clothes and locked them tight to a rack full of servers.  I then quickly locked on the pink collar.   I was 1/2 way committed!

What had I done!??  I was naked in the server room of the office with no way to get out until everyone had gone!  The keys to my male clothes were in the car and the only clothes I could realistically walk outside to the car in were locked in my cupboard - the key to that was outside.

I could wait naked and do it that way, but that wasn't the point, so I dressed into the wedding dress.  First, some waterproof plastic knickers - like baby pants but tight like girls briefs - just because they felt nice.  Then some ivory frilly knickers, plastic lined too, just because.

I had a white basque and stockings next - dressing quickly to get settled.  I added a pair of nipple clamps under the breastforms in the bra of the basque - they would hurt later but with the handcuffs on behind my back I wouldn't be able to remove them.

I slipped the dress up and zipped it on, getting the fit right and fluffing out the skirts and making sure the giant bow was straight.  I popped the veil and gloves on and slipped my stockinged feet into the shoes and did up the little straps.  I did a little twirl.  Awesome

I quickly locked the leg cuffs on, making sure they were done up just tight enough but not too tight that I would be unable to walk.  With the heels on I would have to be careful.

I picked up the handcuffs and ran the chain up the back of the dress, locking in my left wrist.  Before I could breathe, I snapped the right one on, click click click locking myself up tight, hands behind my back.

OMG.

Probably not even 5pm and I'm totally inescapably handcuffed in a dress in the office.

And I waited.  And waited.  The server room door had a little window in, and I watched as my colleagues filed out slowly over the next hour.  I hadn't seen a few people leave and besides it was still light out.  So I waited some more.

It was excruciating.  Stuck in the little room in the dark, in secret cross dressed wedding dress bondage in the office. I'd outdone myself this time.  Plus my nipples were on fire.

Minutes seemed like hours and every face passing the window on their way out felt like a potential discovery.  If someone shone a light in, there was nowhere to hide.  Not dressed and cuffed anyway.

Finally I could see it was dark out.  Had the cleaners come?  I hadn't seen the boss leave either.  What to do?  I couldn't really wait there all night - at some point, security would come round and check, but not until about 9pm.

I listed closely at the door - nothing.  I was just about to turn the key when the boss came past the window.  I was right there at the door - if he turned his head and looked closely, I'd be seen by the light from the office.  SHIT!

Thankfully he left and I didn't hear him come back.  Distant car noises - were they his?

I had to go for it.

Unlocking the door as quietly as I could, I peered out.  Silence.  Thats good, the clicking of keyboards usually gave people away.  But I waited by the door for agonising minutes, not sure.

Finally I summoned up the courage to tiptoe out, but the chains and dress were so loud that it was futile.  If there was someone there they would have heard.

I checked round the corner - deserted.  No way to be totally sure, except that the time meant the probability was in my favour.

I swished round the back door.  All clear.  I could only just open the handle with my cuffed gloved hands - but I pushed the door open a crack.  All clear outside too.  All the offices that overlooked the area looked deserted too.  I stepped out, but in my haste, the door closed and cuffed as I was, I couldn't catch it.

Click

Fuck - that wasn't in the plan.  Cuffed hand and food outside in a wedding dress - eek!

Ah well - nothing to be done now- I hoped noone was there.  I hobbled over to the far end of the deck and retrieved the keys. I was so glad to get the cuffs off.  I swished around the outside of the building via the relative safety of the dark back path and hurried into the shared brightly lit but thankfully empty lobby.  Punching the code on the office door I was quickly back inside.

Thank fuck.

Part 2 - need to get the key to my male clothes in my car.

I had one last petticoat swirling twirl in the dress and then quickly stripped off the wedding dress.  I packed it quickly away into the dress bag and unlocked the cupboard with the retrieved key.  I dressed in the leather skirt and boots and pink fluffy top.  I gingerly removed the nipple clamps - fuck that hurt.  Time to get the last keys.  I grabbed the car keys and made my way outside in the very public shared carpark.  Our company spaces were at the back (of course) and under bright light.  There was also a security guard in a little hut not too car away.

My heels clacked as I walked and the leather skirt was tight and restrictive, making me take little steps.  I felt like everyone was watching, but there was no-one.

I was 1/2 way across the car park when a car started up and the lights came on.  I had nowhere to go.  I wasn't made up, but I had long ish hair, so I let it flop and carried on walking, hoping that they wouldn't be looking.  They passed right by, not even slowing.  Holy crap.

I got the key out on my car and hobbled back as fast as I could.  Almost back into the lobby - someone was there!  Leaving from my office too!  Holy Shit.

I ducked into the relative dark of the side of one of the buildings and waited to see who it was.  Security - thank god, having a check.  But they usually locked the doors once they were done.  Oh no, that would not be good - I could hardly go home to my wife in what I was wearing!

Security entered the next office so I quickly ran inside and punched in the code to my office - the door mercifully opened. They hadn't locked up yet!  I hastily unlocked my male clothes and stripped off, stashing my outfit back into the cupboard - I wish I could have worn it for longer, but it was now time to run!

I just had time to grab my bag as the guard was coming out of the neighbouring offices.  He seemed a little confused that I was there

'just popped back for something - glad you hadn't locked up'

He seemed convinced and chatted for a minute and then we were both on our way.

Thats when I looked up and for the very first time, saw the tiny red blinking light of a minute security camera.

Uh oh.

School Uniform

I was lucky enough to score a couple of amazing wins on eBay maybe 12 years ago (man, time flies) - some adult sized proper catholic school uniform dresses.   These are aways a must have for a cross dresser - there is something captivating about uniform.

Anyway.  I had 3 dresses.
One blue gymslip like dress that was very short with a kind of dropped wast with box pleats not he skirt
One green/gold/red plaid gymslip dress that buttoned on the shoulders and had a high empire style waist with box pleats that fell from almost bust level that was also short, but not as short as the blue one
And another plaid one that zipped up the back that more traditionally shaped with a still slightly high waist but was also box pleated.  Kinda like these ones

I also had (of course) a white peter pan collared school shirt that had cute short puff sleeves, some peraline kneed high socks and some black patent mary jane style school shoes.    Awesome.

Be aware, just because I have a fetish for girls school uniforms does not mean I have a thing for actual school girls.

I think the uniform is such a powerful thing as it's a very definitive symbol of being female.  Boys could not ever hope to attend school in a girls uniform.  I spent my teenage years wishing I could attend the girls grammar school all dressed up in the same uniforms, taken under the wing of some gorgeous girls.

The uniform it just a reminder of that time.


Anyways, I love dressing up in these gorgeous official uniforms in public, putting myself in positions of potential humiliation.

I mean, what is more ridiculous than a grown man in a school girl uniform?

Did I mention that I love jeopardy bondage cross dressing humiliation predicaments?  ;)

One time I left a padlock key underneath a streetlamp at the far end of a brightly lit park about a 10 minute walk through residential streets from my house.

Coming back home, I dressed up in one of my school uniforms - the one with the button shoulders I think.  Staring with underwear - a little padded bra and some frilly knickers - not at all school regulation, then the peter pan collar blouse, then the dress, buttoning each shoulder and finally the lacy knee high socks, making sure they were straight and I looked the part in my shiny mary janes.  I locked the front door from the inside and went out to the back garden.  It was about 9pm I think on an autumn evening, so dark, but some people were still about.

I took the back door key, a small length of chain and 2 padlocks, locked the back door so the house was locked and secure and went to the back gate.  The gate led to an access passage behind the row of houses where I lived and then out onto the street.  I unlocked the gate and then locked one end of the chain to the hasp of the gate.  Nervously, I threaded the shackle of the padlock through the hole in the middle of the backdoor key and hooked on the last link of the chain, now dangling from the lock on the gate.   Once the padlock was locked, the only way back into the house was via the key under the lamppost in the park 15 minutes walk away.

Theres a moment when I'm squeezing the padlock just before it locks, where it could click locked at any moment.  Time stands still and theres a moment when I can still back out.  It's a feeling that gives me butterflies even thinking about it.

Then I give it a tiny squeeze too far and 'click' - its locked and I'm committed.

I pull on the chain trying to see if theres a way out.  It's futile of course.  It's a sturdy chain locked with decent locks to the hasp of the back gate.  I made sure of that.

Now I have to go get the padlock key.

I wait nervously in the dark by my back gate, listening for movement, for sounds.  There are none.  I pick my way down the alley and sit, heart pounding in the dark, waiting before I have to walk into the orange-lit street.

What the fuck have I done? I can't do this!

I have to walk through residential street until I hit a small path that leads to the park.  That path is probably the worst bit as it's narrow and winds around the front of a lot of houses.  It's not well lit, but there is nowhere to hide if someone comes.

My heart in my mouth, I start walking, my mary jane shoes lightly clip clopping on the pavement, to me this sounds jackhammer loud and will give me away in an instant, but none is there.  I can hear the sound of televisions inside houses and the odd car driving by somewhere.  I carry on, committed now, no way back, or I'll be back in my garden looking at the useless backdoor key, still locked to the gate.

Further and further away from my house I walk.  Down the streets, dressed as a catholic school girl in a very short school pinafore.  I make my way to the first of the little alley way paths and pray there is no-one walking down the other way.  Its dark enough that even if they were they might not get a good look.  Thats no comfort.  I'm fairly short and reasonably fit, but even under the makeup, I'll still a man, a pretty one perhaps, but still a man.

Finally, I'm out of the darkness of the path and into the open of the park.  It's a big park, grassed with a childs play area.  And with a brightly lit path running through the middle.  Right at the end is my key.  I decide to just go for it and walk boldly around the path, with as feminine steps and manner as I can muster.  At last I have the key in my hand.

Now I have to walk back, with all the same possibilities and chances of getting caught.

Why the hell do I do this to myself?!

I get home, having walked for 30 minutes in public dressed up in a school uniform.

I unlock the back door key and finally I'm safe.

Alice In Wonderland Dress

I had a lovely blue cotton Alice in Wonderland dress that I bought from http://www.mgdclothing.com.

I asked for a slight customisation - white peter pan collar and matching white cuffs to the puff sleeves instead of elastic and a frill.  It had a crisp white apron that had large shoulder frills and tied in a huge thick white bow in the back.  The shirt was about mid thigh length and super full.  Gorgeous.

I bought a massive white 6 layer net petticoat to go underneath so it would pouf right out - every sissy's dream.

I'd wear some white lace knee high socks and the same patent black maryjanes that I wore with the school uniforms.  A blonde wig and bow completed the look.  Perfect.  It was adorable, swishy and full and not at all explainable if I was seen in it in public, which is why I had to have some public humiliation risk adventures in it ;)

The design has changed slightly since I bought mine, but you get the idea.

Adventure one.  

All dressed up, its late, midnight and everyone is asleep.  I wanted to try to walk to a particular part of the town that involved walking through lit suburban streets, across a main road and down a road that was lined on both sides with turn of the century terrace housing with no side streets or much in the way of hiding places.   

I wanted to do this because that was the way I walked to the train station when I was catching the train to work.  I wanted to have a secret about that route that only I knew about.  Well, hopefully only me, that was the challenge.

There was no key I had to go fetch like with other adventures, this was a purely self motivated one.  And besides once you're far from home in suburbia in a dress, it doesn't matter if you have a key to find or not, you still have to get back home without being spotted.  

So I just walked out of the house and down the road. In an Alice in wonderland costume. 

I had a few streets to go before the main road, it was terrifying. There was a footpath at the end of the last street - narrow and exposed. My dress was poofing out and I twirled up the path, enjoying the freedom. Then I was at the main road.  It's a short walk across - it's still reasonably busy even at midnight, so it felt so exposed to walk the 25 metres out from the path and across the road to the relative safety of the terraced street. I'm about a kilometre from home at this point. 

I walk down the footpath of the one way street. It's crazy. If anyone drives or is walking down the road, they'll see me. I walk about 3/4 of the way down the street, passing houses I walk past every day until finally a car comes. I hide in the front porch of a house. There's not much room and my dress if poufing out. I hope the driver doesn't live here. How the hell would you explain that? 

The car passes. Thank god. I chicken out. I turn round and start the walk back. It's no less terrifying in reverse. I'm almost home when another car comes. I run around the corner quickly and hide in the garden of a house. I squeeze my way into their back garden, my heart is pounding. The car is stopping out the front. It's a taxi dropping off the owners and I've managed to hide in their damn garden. Oh fuck. 

I tuck myself in the dark next to the shed. The lights go on in the house, so I just have to wait. The trouble is their driveway is gravel so I don't know how I can leave without it being obvious. I'm so close to home, maybe only a few hundred metres to the end of road before I can get to my street, but I'm stuck. Holy shit. 

I wait about 10 minutes. I'm not sure, I don't have a watch. It seems like an eternity. I creep out and just brave the crunching gravel on my shoes. I need to get home. There's stirring in the house. I don't look back. I just run down the street, skirts and petticoats flying. I need to be home. 

Finally, I'm at the passage at the back of the house and safe. My heart is pounding. What a crazy adventure. 

More in another post.