Lilly Barton, 007

For those of us who have to keep our feminine side secret those gorgeous, private, special times in our rooms with our girly wardrobe can be like putting on a major operation or going on a special mission. “Is this really all worth it? Is this what other men do?” we must all be thinking. Well, I thought I would share with you what I do in my own special time, in the interests of scientific research, and because, well, I just like to talk about it. And if it all sounds like a bit of a secret mission? Well, it is isn’t it!

1. Secure the perimeter. I make absolutely sure the front and back doors are locked and I ‘accidentally’ leave my key in the in the lock so no one can get in. It’s bad enough when an Amazon driver rings the doorbell when you are mid-flow. Having someone walk in on you would be like being caught in the heart of the Kremlin with Russian launch codes on your USB stick. There would be no escape!

2. Retrieve your secret equipment from its cache. It’s probably not necessary to keep it buried in a concrete pipe on a remote wooded hillside. I keep mine in a black bin bag in a dark corner of the loft. Take great care while doing this. It would not do to be found dead at the foot of the loft ladder clutching a bag of ladies’ underwear.

3. Establish a sterile zone in which to work. When your mission is over it’s vital that you leave nothing to suggest you were ever there. I clear an area of floor so I can easily tell when everything is back to normal.

4. Contain the situation. Nothing must get in or out. I keep all my material in the same place and take nothing out of that place in case I leave incriminating evidence somewhere else in the house.

5. Deploy your equipment. Working quickly and accurately, with a professionalism born of years of training I lay out all my ‘materiel’. Detail is important. I remove shop tags carefully, bagging them all for disposal. If I am going to take photographic evidence I set up my camera equipment. My Quartermaster (me) has issued me with one of those Bluetooth remote camera buttons. It’s the most useful spy device ever.

6. Final check. I’m almost ready. Time to check everything is in place. I check how much elapsed time has passed and how much running time is left. I double check the perimeter.

7. Leave your past behind. I undress completely. We can only cross the border to the other side if we leave behind every trace of our former, male existence. Take everything off. It’s for your own protection. If you do get discovered mid-mission you don’t want anyone to demand “Well, if you’re not Lee then, why are you wearing his socks!”. And you don’t want those surveillance photographs you have risked so much to get to be ruined because you have forgotten to take off your manly watch.

9. Take on a new identity. Now this of course is the main part of the mission. Take your time. You are going to want to look back at this time and remember it in crystal-clear detail. Don’t rush it like a rookie and in your haste put your suspender belt on inside out. I make sure I savour every minute.  The mission has been days in the planning and I want to enjoy the execution.

10. Set achievable objectives. I set a first objective: put on bra, panties, stockings and suspender belt. If I then have to abort the mission suddenly, at least I will have achieved that. Its at this point in the mission that I am at my most vulnerable – and it feels lovely! I enjoy the feeling of being in a foreign country. All that lace and nylon! It feels exciting, and yet I feel as if I have always lived here.

10. Disguise yourself. This is the most technically challenging part for me. I sit on the bed in front of the mirror and apply makeup and wig. I’m the first to admit I’m not great at it. The results may not be that convincing but I absolutely love doing it. OK, I may not ‘pass’ under interrogation but I reckon I could pass through a checkpoint in the dark.

11. Make a copy on microfilm. Or at least on your mobile phone. Before moving onto my next objective I take photographic evidence,  posing away in my bra and panties and snapping that Bluetooth remote.

12. Complete the mission. I finish dressing in character. I’ve usually spent weeks shopping for the parts of my outfit and now it all comes together. Yes! It’s worked! That checked skirt DOES go well with the jacket and, yes, and that top does have the same shade of red as my hair. I look lovely! Lilly smiles back at me from the mirror – we can’t help smiling at each other! It’s all been worth it. Sometimes though, inevitably, it all goes horribly wrong. I make a schoolboy error and choose the wrong item. It just doesn’t work at all!  The mysterious woman I have come to meet flashes her disapproval in her eyes and pretends she doesn’t know me. I know what she is thinking. After weeks of meticulous planning I have jeopardized the whole mission. If we’re found out now, they’ll be laughing at us in the canteen for years. “They found him in the bedroom,” they’ll say, “but do you know the funny part? He was wearing a striped blouse with a polka dot skirt!”

13. Extraction. You’ve achieved your objectives. Now get out of there. I take everything off and put it in a large plastic bag. I don’t work with lots of small bags – I think that’s for amateurs. I like to know that I’ve got everything in one place. I take off all my clothes and then head for the bathroom. Everything I use to remove my makeup has to stay on or in the sink. I can’t afford to leave any evidence that Lilly has been there. I return my stash of equipment to it’s hidden cache.

14. Sterilise the site. With a forensic attention to detail I work my way through the mission area inch by inch, looking for even a single red hair on the carpet or smudge of makeup on the mirror. I used to leave sequins behind me, such a beginners mistake – I’m too much of an old pro for that now. I stand still and survey the scene in detail from left to right. No, we’re good! It’s done!

15. Rest & Recuperation. I have a long hot soapy shower – a chance to relax in the steamy heat and wash away that last bit of mascara, that scent of makeup remover. If they catch me now they’ll have nothing on me.

16. Debrief. Back in my normal life, there is a chance to think back on how the mission played out. What worked well, what didn’t? I make a note to buy some cream lingerie the next time, and perhaps I could do something different with my hair.
And so my mission is truly over I have survived and live to cross-dress another day. But I am just riding on the bus into work when a horrible realisation hits me. All those photographs I took! Theyre just sitting there in my phone’s photo gallery! How could I be so stupid? Just a few seconds sends all my images to a Private folder but my incompetence has left me morose. I don’t know how much longer I can carry on like this. Perhaps I’m getting too old for it. Perhaps I should throw it all in for the simple life.  I could buy a small guest house in the West Country. There’d be no more skulking around.  I could live my life as a woman. I feel I could be more open and honest. And if a holiday maker called me over to her table and said, “Excuse me, Ruby, there’s a sequin in my soup”. I could just say “well you can have that for free!”


6 thoughts on “Lilly Barton, 007

  1. That was one of the best accounts of Crossdressing I have ever read. I will need to refer back to this. During my dressing sessions the place looks like a disaster and I spend at least another hour worrying if all the evidence was put away.


      1. There will always be some evidence left behind no matter how well you think you have cleaned. When my child was very small I left my heels out once and found them walking around in them.


  2. Lilly I can so relate to so much of all of the above – such military style planning and meticulous checking of everything and anything around as I dress/undress.

    Thanks for sharing. It makes it easier this end to know that living in a closet presents similar hurdles for others too.


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