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20. The Crossdressing Barrister

        FrouFrou: fancy meeting a slick barrister with a feminine side?
        PinkParanoia: not particularly, no
        FrouFrou: I’m really cute as a girl
        PinkParanoia: I‘m sure you are, but I prefer men
        FrouFrou: I would let you tie me up and whip me
        PinkParanoia: I’m not interested
        FrouFrou: I like your photograph. you are very pretty
        PinkParanoia: thanks
        FrouFrou: I look lovely in stockings
        PinkParanoia: I’m sure you do
        FrouFrou: would you prefer me to tie you up?
        PinkParanoia: I don’t think so, no.
        FrouFrou: what do you fantasize about then?
        PinkParanoia: not about men in dresses. I’m afraid we are not compatible
        FrouFrou: if we would meet, what would you want me to wear?
        PinkParanoia: an Armani suit – or black leather
        FrouFrou: ok, I will just wear women’s underwear then
        PinkParanoia: me too
        FrouFrou: good. now, what are your orders for me?
        PinkParanoia: orders?
        FrouFrou: just tell me to do whatever you desire
        FrouFrou: I want to be under your control from the very first minute we meet
        FrouFrou: I want you to tell me when to refresh my makeup
        FrouFrou: when to play with my bra strap
        FrouFrou: when to smooth my stockings
        FrouFrou: and when to comb my gorgeous blonde wig in which I look like a glamorous queen
        PinkParanoia: you will do as I say?
        FrouFrou: whatever you desire
        PinkParanoia: you’re funny
        FrouFrou: you will have the most beautiful transvestite in the world under your command
        PinkParanoia: he will do anything I ask?
        FrouFrou: she
        PinkParanoia: I want to see her paint her fingernails
        FrouFrou: you may
        PinkParanoia: and while she does it I will take away her stockings and order her to roll them up my own legs while she is on her knees
        FrouFrou: ooooh, but they look so much better on me
        PinkParanoia: if you don’t obey I will smudge your nail polish
        FrouFrou: I’ll be furious if you try such stunts
        PinkParanoia: then I’ll definitely have to do it
        FrouFrou: mmm
        PinkParanoia: I use my stockings to tie you to the bed and while your hands are helpless I wipe the nail polish off and slap your fingers for having been naughty
        FrouFrou: I’ll deserve it
        PinkParanoia: of course you do. I’ll also rip off your wig
        FrouFrou: noooooo
        PinkParanoia: then gag you with your own stockings
        FrouFrou: my gorgeous stockings in my mouth ... how awful ...
        PinkParanoia: you will struggle and beg for mercy – you will regret having met me and wish you could be back in men's clothes
        FrouFrou: mmmmmm
        PinkParanoia: and I will get to work on your cock to remind you of what you are
        FrouFrou: oooh!
        PinkParanoia: since you forgot you are a man you need to be fucked like a bad girl
        FrouFrou: yessssss
        PinkParanoia: until you scream for me to stop
        FrouFrou: mmmmmmmm, a dildo up my ass does make me moan
        PinkParanoia: oh, you will moan
        FrouFrou: between a fucking and a punishment - oh what a place to be, Mistress
        PinkParanoia: when you cannot stand it anymore I will set you free
        FrouFrou: free of my chains – with nothing? not even my lingerie?
        PinkParanoia: yup
        FrouFrou: I'll have to chase after you
        PinkParanoia: but will you catch me?
        FrouFrou: I will order you to stop, to get on all fours and to bend over – NOW
        PinkParanoia: it’s a bit awkward with all my colleagues watching
        FrouFrou: lift that skirt so I can admire the lace on your cheeks as I fuck you
        PinkParanoia: ssh – I’m in the office
        FrouFrou: god, we are so compatible
        PinkParanoia: you think so?
        FrouFrou: YOU DON’T?
        PinkParanoia: I don’t know. I’ve never done this before
        FrouFrou: you’re a natural then
        PinkParanoia: really?
        FrouFrou: oh yes baby

After he is gone I check his profile. ‘Lawyer 36, in Golders Green with two dogs and grand piano is looking for a long-term relationship’
        Never underestimate the hidden depths of an innocuous add.
        There is no photograph but when I walk up the stairs of Leicester Square tube station Saturday at 3 I recognize the delicate grace with which he is leaning against a lamppost, hands crossed in front of his chest, little finger waving.
        His hair is cropped short in an effort to camouflage his receding hairline. His deep eyes blink happily, accentuated by a hint of mascara. His cheeks shine from too much L’Oreal Nr 101 Morning Rose blusher.
        He embraces me like an old friend, grabs my arm and leads me into a coffee shop just off Charing Cross Road.
        We pick a small table by the window designed for two to sit opposite each other. He squeezes next to me onto the narrow bench.
        It is immensely more difficult to talk than it was to chat. Carefully avoiding the issue we babble on about the weather, our families, our hobbies.
        The waitress, a slim blonde in a tight dress and black fishnets recites the specials.
        ‘She is very nice,’ he says when she is gone.
        ‘Very nice,’ I echo.
        ‘I like her nylons.’
        ‘She looks good in them.’
        ‘Do you want to see mine?’
        Before I can say ‘not particularly’ he has pulled up his right trouser leg. Sheer blue stockings are rolled neatly around his ankle. Dark curly hair is sticking out above. He moves his foot and the shiny material reflects the sunlight coming from the window.
        ‘Do you think I’m beautiful?’ he asks.
        ‘You don’t shave.’ I say, not sure if I’m suppressing a giggle or a surge of repulsion.
        ‘Are you ready to order?’
        We both look up at the waitress.
        He drops his leg.
        She smiles innocently – first at him, then at me.
        ‘I like your tights,’ he says pointing at her fishnets.
        ‘They are stockings,’ she says.
        Sparks fly between my date and our waitress and I wonder why it is I who blushes.
        ‘Do you think she noticed my stockings?’ he asks when she is gone.
        ‘Would you want her to?’
        ‘Oh yes.’
        The rest of our date is over shadowed by his obsession with the following questions: Did the waitress come to stop him from exposing his stockinged leg? Did she come because she wanted to see more of it? Or has she noticed nothing? Do I think he is a pervert? Do I think the waitress is a pervert? Do I think the waitress thinks he is a pervert? Do I think the waitress thinks that he thinks that she is a pervert? Do I think he should ask for her number? Do I think he would make a gorgeous girly? Do I like his stockings? Do I think the waitress likes his stockings? What would I do to his stockings if we were alone? Am I wearing stockings?
        I do and I’m almost relieved when he gropes to feel their lace.
        When the waitress looks he kisses me. His lips are soft and taste of the caramel cake he just ate. I reach for his tongue but he retreats. I push for more. He gives me the tip of his tongue but when I respond he retreats again.
        I give up. Confused I bite my lips.
        ‘Did you like that?’ he asks.
        I grudgingly admit that I did.
        ‘A natural in many ways,’ he says with a grin. ‘We need to meet again.’

The following weeks we spend hours planning our second date.
        Should we go to a club? What kind of club? Somewhere where he can dress as a girly? Or just a bar where we can dance knowing he is wearing corset and stockings underneath? Should we go to a department store beforehand and get a makeover? Would I want to watch him being turned into a gorgeous girly? Would I help him put on make-up? Should he wear a flouncy skirt or a tight one? Pink or black? Long or short? A corset, a basque or a bra? Would I advise him on his panties and stockings? Where should we go shopping?
        I answer all his questions again and again and again but whenever I ask for a definite date he has a deadline in his job, a family emergency or is about to go on vacation.

On a sunny Sunday afternoon he calls. He doesn’t say his name, but I recognize his high-pitched pervy voice right away.
        ‘I’m wearing a blue skirt and a pink blouse, sheer stockings and a bra. Do you think I’m a gorgeous girly?’
        I’m walking along the river towards the Tate Modern, zigzagging between parents buying sugared almonds for their kids, students browsing for books at the second hand market underneath Waterloo Bridge, lovers staring glassy eyed at the soft waves of the Thames.
        I’m the only person in the world who is walking alone. I hold onto the phone.
        ‘Yes, I think you are a gorgeous girly,’ I say.
        ‘Do you think I’m a pervert?’
        ‘Yes.’
        ‘Do you want to see me in my stockings?’
        ‘If you beg me nicely,’ I say and frown at a woman who smiles apologetically because her little blonde boy just bumped into my hip while looking up to watch his kite take off.
        ‘If you beg me nicely,’ I repeat as I move on. ‘I will allow you to put on your wig and to kneel down in front of your mirror to watch the pathetic little girl you are wank herself off in her pathetic little pink blouse.’
        ‘Oh thank you, Mistress, thank you so much.’
        Walking through the happy Sunday afternoon crowd with the cross dressing wanker on the line I’m suddenly scared. I’ll never be the mother of a blonde boy running along the river with a kite, nobody will ever buy me sugared almonds and I will forever stare alone at the soft waves of the river Thames.
        ‘Ohmegod, what a gorgeous girly I am. Thank you Mistress, oh thank you, oh, oh, oh oooooh,’ he moans.
        I switch off the phone. Although the sun is still out I shiver.

The next day he is back:
        FrouFrou: do you want me on my knees?
        PinkParanoia: yes, but I’m beginning to think that –
        FrouFrou: what?
        PinkParanoia: never mind
        FrouFrou: do you want to be submissive?
        PinkParanoia: not sure
        FrouFrou: but you feel dominant with me, don’t you?
        PinkParanoia: you’re too easy to dominate
        FrouFrou: I met a real dominatrix on a site called alt
        PinkParanoia: good for you
        FrouFrou: she doesn’t want me to contact her. she will contact me when she so desires
        PinkParanoia: smart bitch
        FrouFrou: do you think she likes me?
        PinkParanoia: ask her
        FrouFrou: she said if I fail the test of not contacting her there will be no suspender snapping for me
        PinkParanoia: she likes you
        FrouFrou: you think?
        PinkParanoia: why else would she want to test you?
        FrouFrou: do you think she will contact me, if I stay quiet?
        PinkParanoia: only one way to find out
        FrouFrou: stay quiet
        PinkParanoia: what a great way to get rid of unwanted suitors
        FrouFrou: you think I’m an unwanted suitor for her?
        PinkParanoia: probably not
        FrouFrou: so should I call her?
        PinkParanoia: don’t think so
        FrouFrou: she’s got me on a leash already
        PinkParanoia: sounds like it
        FrouFrou: she doesn’t want to meet me does she?
        PinkParanoia: forcing you to stay away might be a good sign – she knows you want to suffer
        FrouFrou: and this is the best way of making me
        PinkParanoia: but then again – maybe she just wants you to stay away
        FrouFrou: I’m so depressed. it will go nowhere like this

There is a silence of two years.
        Then he reappears on my screen. He managed to hook up with the Dominatrix but their relationship has run its course. Do I want to see him in make up and stockings?
        Before I know it he has switched on his web cam and weasels around in front of it, putting on blusher, eye shadow, lip stick and earrings. He tries several wigs and asks my opinion on each of them. I minimize him and continue with my work, only occasionally making polite comments on his gorgeousness. He seems content enough with that.
        After several similar sessions I ask him to come to a club with me, where lots of people might be interested in what he has to offer.
        He sounds intrigued.
        Four or five times I invite him but he never shows up.

He probably won’t come back online when he reads this. I wouldn’t blame him. After all, we are truly not compatible. But I do hope he finds what he needs. And I thank him for being the first who made me wonder what it is I might need.