Crossdressing Makeover


JJ knows how much my male persona likes to be in control. She also knows just how much my female persona, Miss Kitty, needs to let go, to sit back, relax, and enjoy her crossdressing makeover. My new life with JJ in command is jam-packed with surprises and full of laughter, and there have been tears of happiness too. My crossdressing makeover started with a phone call, made so nervously, so tentatively, with my feminine self desperately trying to break free of those subconscious bonds of convention, tangled inhibitions and knots of despair.

From the moment I heard JJ speak so calmly, so intelligently, so reassuringly – but also with an undercurrent of joyful humour – I knew Miss Kitty was coming home. And after my crossdressing makeover visit to JJ, Miss Kitty was ready to hit town, encouraged by JJ who knew just how much I wanted to do this. It had been three months since that first crossdressing makeover visit to her Cheshire boudoir cross-dressing service and now Miss Kitty was ready for her ‘coming-out’ weekend, a special crossdressing makeover in London, guided with incredible insight into my psyche by JJ. Of course I was anxious, daunted by the prospect of walking tall (I am over six feet in flats) in public, dressed in what I hoped would be a flattering black satin dress.

From the divine …

My crossdressing makeover weekend in London began on a Friday night. Miss Kitty was allowed to decide what would happen. With some guidance from JJ, an elegant crossdressing makeover evening was planned. The main event, the opera Faust at Covent Garden, front row of the Grand Circle – and it was very grand. Before the performance and during the intermission, a table for two girls in the Crush Room with Chablis, salmon, and pavlova. I was wearing a spare pair of JJ’s hold-ups: I had forgotten to bring black stockings or tights.

JJ had applied my crossdressing makeover cosmetics, checked my wig and supervised me getting into my dress. Finally, JJ pronounced me not just ready to be seen in public, but OK to be seen out with her. JJ made me feel like a million dollars. Even so, I was a little anxious about appearing in public after my crossdressing makeover in London. I was also worried that an opera (sung in French, with more deaths than an episode of Midsummer Murders, about a man who sells his soul to the Devil to regain his youth and virility) might not be JJ’s cup of Assam tea. I told her that our crossdressing makeover chauffeured car would be ready to whisk us away at any time should she so wish.

The great thing about being out with JJ is that she attracts attention: she is simply stunning. She is elegance personified. She wore a gorgeous, mid-length velvet skirt split to just above the knee and the most exquisite Florentine black silk blouse. So, the chances are small of anyone spending too much time trying to work out if the tall girl with her really is a girl or just a lovely crossdressing makeover T-girl. And, when one couple was clearly trying to figure me out, JJ was expert in making sure that their rude stare was not prolonged.

Faust is three hours long. Even with a 30-minute break in the middle it might have been an ordeal. But the singing, especially from baritone Simon Keenlyside and tenor Joseph Calleja, was divine. The sets were fabulous and at times bold and breath taking. The orchestra was fantastic. JJ and crossdressing makeover Miss Kitty were captivated. The big star of the evening was Bryn Terfel, the Welsh bass-baritone, taking the part of Mephistopheles, otherwise known as the Devil. From the moment he appeared, larger than life, answering Faust’s ‘prayer’ for his lost youth to the descent back to hell, he injected incredible power and energy into his role.

But, he also brought humour. As the witches gathered for their Sabbath, he appeared as their queen, in a cloak and wearing a jewelled tiara as his crown. Then suddenly his cloak was cast aside, revealing to the joy of the audience, a black and silver gown, complete with bustle: his own spectacular crossdressing makeover. I did wonder for a moment whether JJ had arranged this treat especially for me. With her, anything seems possible. And seeing the Queen guitarist Brian May in the stalls just below our front row dress circle seats added yet another frisson of crossdressing makeover pleasure.

And so, we left the splendour of the Opera House and I experienced one more delicious crossdressing makeover moment as I walked in my dress with JJ towards our waiting car. The cool air in the street rushed around my thighs leaving me in exultation as I rejoiced in this unexpected physical expression of my femininity. An incredible beginning of my crossdressing makeover weekend.

To the sublime

Saturday was a different crossdressing makeover day. This was JJ’s show and she was not going to give me the slightest inkling of what was to happen that night. Teasing me in my ignorance as she took my male persona on a crossdressing makeover window shopping trip. The afternoon was so fabulous shopping on Bond Street. The fascination of Dolce and Gabbana, Rigby and Peller’s seductive lingerie, Jimmy Choo’s sexy shoes, Thomas Pink to buy a shirt and the highlight - the delightful shock of holding, sadly for the briefest of moments, a four thousand pound Chanel bag in Fenwick’s. Giving the shoppers in Victoria’s Secret something to talk about when JJ held up against me various scanty items of potential crossdressing make-over lingerie.

Then, it was back to our hotel for the second crossdressing makeover night. JJ told me that I should come to her room at 6.00 pm dressed in my black leather pencil skirt and cerise silk blouse. As I entered the room she told me to ring room service and order Chablis for us and a glass of champagne for her friend Tiziana who was to join us shortly.... my first crossdressing makeover surprise of the night, 3 girls out on the town together. As JJ began to apply my make-up, T arrived in a flurry of Italian-accented chatter. This was going to be a girls’ crossdressing makeover night out to remember. With a touch of added spice when T insisted on showing me pictures on her iPad from her latest and risqué photoshoot! But even she was not a patch on JJ in the glamour department.

JJ was wearing a slinky black dress and was walking almost as tall as me in her oh-so-desirable, oh-so-gorgeous Louboutin seven-inch heeled shoes. If I wear anything higher than three inches I get vertigo. After the Chablis and Champagne and final touches to our make-up and attire we stepped out of the hotel and into our crossdressing makeover taxi. JJ instructed the driver to take us to an address in the heart of Soho. Soon, we were piling out in front of a club which was my second crossdressing make-over surprise. Our evening was to start at Madame JoJo’s Kitsch Cabaret, a place for Saturday night celebrations: birthdays, anniversaries, hen parties and, tonight, Miss Kitty’s crossdressing makeover ‘coming out’ in style.

We were taken to our seats with wine and nibbles as we waited for the show to start. The club was filling up fast. A magician came to our table and introduced himself. Tommy gave us a personalized performance of his amazing tricks. Such crossdressing makeover fun. Then Miss Terri began the cabaret. She was fantastic: her mature figure incredibly feminine. Her powerful voice mesmerizing. Two other singers rang the changes with her: the tall ‘glamazonian’ Miss Sahara; and (my favourite) the classy and astonishingly beautiful Miss Maddison Lee. A male belly dancer with designed stubble added to the sense of zest in the crossdressing makeover atmosphere.

Any reserve I felt at first was quickly disappearing, as my inhibitions evaporated, assisted by the liberal quantities of white wine JJ was adding to my glass. I even got to my feet to join in the chorus of ‘Let me entertain you’. Then the third crossdressing make-over surprise, the belly dancer came to our table and I was photographed with him. He asked whether my DD cup boobs were real. At that point, he began investigating for himself rather impudently. Delicately removing his hand from just underneath my bosom, of course I said "Absolutely, yes. Hands off.”

My crossdressing makeover weekend in the company of JJ and Tiziana, hens and their entourages, birthday boys and girls, and those expressing their female selves far more glamorously than me, I felt totally at one with my femininity. Miss Kitty had finally arrived and was here to stay in her crossdressing makeover finery. My only wish that I might have been a little more flamboyantly or seductively dressed. But, as JJ tells me, "You must learn to walk before you can run.”

The crossdressing makeover evening was not over. We went for a light meal on the upper floor of the nearby Social Eating House. As we reached the top of the stairs, a group of young Americans were all too obviously bowled over by JJ. Attracted like moths to a flame, they couldn't get enough of JJ and her Louboutin shoes: she even allowed one of them to try them on. The others looked on jealously. Obviously, future clients for JJ’s crossdressing makeover service! Later, as they left, one of the party came over to our table and said how terrific I looked, a final, totally unexpected but hugely flattering surprise for my crossdressing makeover weekend. Yes, quite definitely, another future customer for JJ.

After settling the tab, we were back into a taxi exhausted, exhilarated and ecstatic. Tommy was not the only magician that night. JJ’s special blend of crossdressing makeover magic was pure feminine enchantment mixed with her tremendous professional skills, with no cards up her sleeve. On open display was her perfect understanding of what an anxious cross-dresser needs in order to build her crossdressing makeover confidence.

My only regret: that I had not encountered JJ years before now. I have missed so much life, so much fun, so much laughter and joy. But now, with JJ’s expert crossdressing makeover guidance, I shall be making up for lost time. If you are standing at the threshold of a new life, ready to let your femininity come rather more to the forefront, take my advice, please. Do not delay, visit JJ in her boudoir, listen to her confidence-boosting MP3s, and perhaps consider asking her to accompany your feminine self on a trip to the world outside. And step out in your stiletto heels for your very own crossdressing makeover.


'Who said, dreams can't come true?'