Sugarmum

'I know I've not been an easy client but Anita knows what I want by now. I'm disappointed she didn't make more of you since you seem so willing.'

I frown confused with what she meant.

'Anita has chosen all of these based on your size so anything should fit.' she tuts disagreeably as she flicks through the cloths but from where I stood I couldn't see what she was selecting.

'What do you think of this?' she says pulling a pair of stressed jeans and faded sweat shirt from the wardrobe. I was surprised with her choice.

'Not much,' I say wrinkling my nose.

She smiled, 'correct answer.' She flung them back and pulled out a stuffy blue pin striped suit. 'and this?' I shook my head.

'Too formal.'

'Good, good,' she said nodding.

I smirk enjoying the game. Was this part of the interview I wonder? Next she pulled out a short floaty cocktail dress in flamenco pink. I looked at her carefully. I didn't know what to say. 'Yes,' she said impatiently. 'and...'

'It's very pretty,' I say cautiously. She says nothing but simply stare at me intently. I assume she wants a more detailed description. 'Luxurious fabric, very elegant, comfortable.' I add. Katie smiled broadly like a grinning cat.

'Yes that's what I thought.' she tossed it to me and in my surprise I caught it. It was of an incredibly light silk like fabric. I stood motionless for a few moments as she pulled open a draw from the closet. 'I think pink is such a pretty colour don't you?'

'Y...yes,' I stutter as she takes from the draw a matching suspender, bra and pantie set, nude stockings and a white slip. she hands them to me and again I automatically take them with my free hand. she then stood silently in front of me for a few minutes, neither of us spoke. 'Patience has never been my strong point. Are you going to stand there like a mute or are you going to put these things on?'

'what,' I gasp in surprise,' I can't.'

she flipped shut the wardrobe doors and gazed moodily at me. She had a devilish gleam in her eye. She came over to where I stood and crowded in close. I could feel her hot breath on my neck and her perfume was overpowering.

'Now,' said Katie, 'I'm telling you clearly if you want me to even consider your suitability, you must wear these things. I've seen you in slacks and a blouse which was enough to arouse my interest, I now want to see how you look in a dress.'

My heart sank at her words.

'But, she continued, I will make it worth your while.' I thought of Roberts Ferrari and felt a glimmer of hope.

'But Kate,' I stammered , 'I can't wear these. I can't wear a dress. I'm a man'.

Katie looked peeved. Theres little difference between this and what you had on earlier. You have such lovely legs. It's a shame to keep them covered. Besides if you're to work for me you're to do as I ask. Now don't argue that's not what I want. if I'm to choose you I don't want additional agro. I get enough of that at work on a daily basis.

'Sorry,' I say again.

'I really don't see the problem. What's the matter? I think there is chemistry between us, don't you?' Katie was looking hurt. 'I thought you wanted to work for me.'

'I do, I do.' I mumble.

'Hang on, there's an echo in here.'

I began to panic. What if she loses patience with me? What if she took offence by being turned down? what if she decided I'd had my chance and blown it? She might conclude I'm unsuitable and never see me again. Anita may not bother trying to place me elsewhere.

'I just don't want you to think I'm easy, that's all,' I said nervously. Because I'm not, but if I wear these ultra-feminine things you might think I am.'

I don't think that.' she gave me a lazy grin. 'I wouldn't think it.'

I looked worried. 'The thing is, you think you wouldn't think it, but deep down you would. You see, you're only saying this now because -'

'Whoa,' said Katie. 'Okay, enough. I give up.'

I bit my lip. Was this the smartest move of my life, or the stupidest?

'I'm going now,' she yawned and rose with reluctance to her feet, avoiding my panicky gaze as she searched for her things.

Oh God, I have blown it, I thought miserably. Before I could stop myself I blurted out, 'Does this mean I'm not suitable. The interview is over?'

'What? Oh ... of course. what's the point.' she still wasn't looking at me. Her manner was vague; she sounded as if she were making polite conversation to a stranger on a train.

How quickly the best interview of your life could turn into one of the worst. I felt my pride melt away.

'Okay,' I said in shaky voice, 'you can stop looking for your things.'

Katie glanced up.'Why?'

'I'll put this dress on for you.'

'And the stockings and suspenders, she says hopefully.

'Panties, bra, What ever you want,' I say surrendering.

She began to smile. The next minute she pulled me into her arms, 'You beauty!' she cried

I clung to her.

'Just as long you don't think I'm cheap or can be bought easily,' I emphasised. 'I'm not a transvestite, all right? I don't make a habit of this. In fact I've never done it before.'

She sent me off to the bathroom with orders to shave my entire body baby smooth using the women's razors in the bathroom.

'A little make-up would do you wonders.' she says, 'knowing Anita she will have left some out for you. if you smarten yourself up you could probably look quite passable, maybe even pretty.' I shut the door.

I stood in the shower and shaved my legs with the pink razor. 'Don't forget your underarms', Kate called through the door. When I was done I got out of the shower and patted myself dry with the towel my body felt like velvet.

'I haven't long,' she calls. I've an important meeting in 60 minutes.'

What a weird situation I had got my self into. but funnily having spent the past hour dressed in Antia's effeminate clothes the transition to the dress didn't seem so great and with nothing on I felt the need to wear something.

I fingered the delicate lingerie. it was scarlet. id always though it had a racy reputation, but these were different. with a little broderie anglaise and some sweet ribbons they looked super pretty. They must have been very expensive and wouldn't make me look cheap. I thought it was the kind of lingerie a girlfriend would wear if she were feeling lucky. I pulled the panties up my smooth legs. They felt wonderful as the cool nylon encased my rear and to my surprise they were remarkably comfortable. The seemed to shape my body. I caught my reflection in the mirror and saw a flattering silhouette. The bra was difficult but after a few minutes of struggling I got it on. I wrapped and fastened the suspender belt round my waist. I let the silky demi slip cascade over my shoulders. It felt wonderful and fell to just below my hips. I noticed a wig on a bust some more jewellery and a selection of make-up. Katie was right Anita must have left them for me on the assumption that we would get this far. I shrugged my shoulders and thought in for a penny in for a pound. I didn't want to let Anita down and I wanted to please Katie so I placed the wig over my head and brushed it in place. I then tried to apply the make-up. I used the moisturiser on my face and applied some liquid make-up. The smell was delicious. I used pencils and shadows on my eyes and hurriedly applied a pair of false lashes. Blusher and lipstick, I really didn't know what I was doing but after a few minutes a feminine face began to appear. My face was that of a woman's. Arched eyebrows over long lashed doe eyes. Pink blusher brought out my cheekbones and my lips were pursed, very plump and kissable red. I put on the stockings and clipped them on my suspender belt They felt so wonderful on my smooth lotioned legs and the ankle chain made my leg look long and willowy. After filling out my bra cups with the synthetic pads I climbed into the dress. It fit after a little struggling. It's bodice was very tight but I assumed it was meant to be. It had puffy sleeves and was made of pink satin. It pulled me in at the waist and the flounced skirt created the illusion of feminine curves.

I picked up the long bangle clip on earrings and clipped them on my ears and the few bangles on each wrist and a woman's watch.

I stood and looked in the full length mirror. Looking back was a beautiful woman. She was dressed all in pink and had beautiful blonde hair in long soft curls caressing her face. Her make-up was not flawless but all things considered it was poretty dramatic, but at the same time very natural. The woman in the mirror turned and raised herself on her toes and spun in the mirror like all women do. I was ready and from that moment soemthing odd happened. I felt different as if id changed gender. After all I was only wearing drag and yet there was something about the softness of my libngerie. the caress of the dress agianst my stockinged legs. the hair sawying on my cheeks that made me feel like a dfferent person. like abeautuful lady. I clocked myslf one more time in the miror. I was ready.yet just before I opened the door I chuckled to myself as this was the most unusual interview i'd had.

I took a deep breath and stepped my stockinged feet back into the bedroom. Katie was on her mobile phone talking animatedly. She barely acknowledged me. She continued to talk in French on the phone. I stood by the door and fingered my dress awkwardly. I wanted to flirt with her but I didn't know how. Not in a dress. I tried to copy what girls had done to me. I strut about the room, waggle my hips, toss my hair and bend at the waist supposidly adjusting my stockings. It works. She marvels at the sight of me as I flutter not just my eyelashes but my whole body at her.

'Pardon,' she says holding the phone from her face. 'Shoes,' she barks pointing to the bottom of the wardrobe. I follow her outstretched finger. There neatly lay a pair of towering high heels that matched my outfit.

'They'll cripple me,' I moan but Katie wasn't istening instead she returns to her call as I bend at the knee and slip them on my stockinged feet. Katie watches with amusement and smiles as she sees me stagger and sway as I try to get accustomed to the heels. 'Pardon,' she says again to the caller and she waves her arms about pointing to my dress and my bottom. I had no idea what she meant. she mouthed something to me and I frowned. I didn't understand what she meant.

'Panties,' she says irritably. 'Are you wearing the pretty panties?'

I nod and ran my hands over my rounded bottom.

'Show me. I won't be long. I'm almost done.' she says. 'do hurry.'

I turn my back to her, bend at the waist and lean over the bureau. I hold tightly the hem of my dress, flip it up over my back to expose my smooth rounded arse cheeks. I hear Katie sigh so I play to the audience by wiggling my hips. Unsure what to do next I look behind me to see her smiling broadly while still talking on her mobile animatedly.

'Good girl,' she says then promptly resumes her telephone conversation her eyes sparkling lustfully. As she talked, she put the phone under her chin and not taking her eyes off me strode across the bedroom picking a surgical glove from her suit pocket. I felt a hard lump develop in my throat and my heart began to race as she stood behind me. Still in deep conversation she calmly placed a gloved hand on my panties. she stroked the material affectionately and her fingers slowly worked under the delicate lace and felt my arse. I squirmed slightly but as she gently touched my hole I did something very out of character. I pushed back onto her probinng fingers assuming this is what she wanted. but she withdrew her gloved fingers and dipped them in her champagne flute. Wet and lubricated she touched my hole again. This time I felt a long fingernail tease my opening. This woman was extrodinary as she continued to talk business and played with my most intermit orifice as if I wasn't there. I tightened my grip on the burea and relaxed my anus muscles so she could plop a moist finger in my arse. I gasped as once inside she slid it smoothly and dare I say deliciously up my anal shaft. She teased me by pumping her hot finger deep into me and then back out so that only the bare tip of her nail remained embedded in my hot canal. I grabbed the bureau frantically as if my life depended on it and again pushed against her finger but this time I let out a slow moan. It lulled me into spaced-outness and by the time she thrust her finger back into me I'd lost the power of speech. After a few exploritory thrusts backwards and forwrads she finnished her call, threw her phone on the bed and slapped my rump with her other hand.

'My god your tight,' she marvells. 'Much better than almost any pussy I've ever fingered! You've past this part of the interview. Flying colours. Full marks.'

Good news maybe but I didn't really care. Now that i'd let this strange woman dress me in these ultra-feminine clothes and probe me in a way i'd never experienced. I was in heaven. I loved the feel of her long hard finger slowly gliding up and down my chute, loveingly caressing my prostate, sending chills along my spine.

'Will I do?' I gasp.

'Hmm! not bad,' she replies thoughtfully. 'Almost done.'

Then as quickly as she begun she withdrew her finger and dramatically peeled off her glove with a medical air. Unsure what to do I remained in the unflattering exposed position .

'What's your ideal, I mean, short or tall, blonde or dark? I ask.

'I like confidence, but really I like all kinds,' she said tossing the soiled glove into the waste bin. 'Anyway personality's more important than looks.'

Sure I thought but somehow I couldn't see Katie employing some hairy arsed builder because he told good jokes.

'So,' she eventually says studying me as if a painting at an auction. 'How do you feel? Nice? Katie had a strange look in her eye. It was almost a possessive look of desire. She sat on a chair and patted her lap. 'Come and sit on my knee.'

I mince across the room to where she sits adjusting my dress. I hadn't sat on a ladies lap since Auntie Margaret came then I was five. Smoothing the back of my skirt down i gingerly sat on her trousered leg.

'That's nice isn't it?' she said touching my hair. 'You look fantastic. You're very pretty. Your hair is so shiny, full and soft. I could see myself spoiling you.' She took my chin in her hand, lifted my head until I was looking her in the eye. 'You've done this before havent you?'

I shake my head.

'I don't believe you. Well...You could do very nicely..'

I nod perhaps a little too eagerly and shes quite for a few moments. With one hand round my waist she put the other hand in my lap and pressed down on my now spasaming cock. I blushed. My little cock had become very aroused during her finger probing and now it was straining in my panties bursting with energy. Katie would have been dead not too notice.

'Oh! you naughty girl,' she says mockingly. 'You're no longer nervous, you're getting all excited.'

I feel my face redden.

'Oh you cheeky thing. I should put you across my knee.'

I blush and my cock twiches wildly. Katie notices my reaction. Next thing I know shes guiding me up onto my feet bending me over her knee. With my hands in front of me supporting my weight my blood rushed to my head, my soft hair cascaded forward partly restrictng my view. Staring at the ground I saw her handbag open in front of me. I couldn't help but look. Inside was a small jewellery styled box wrapped with red ribbon. I wondered if it was for me again as the thought of Robert and the lavish gifts his lady showered upon him flashed through my mind. Katie saw my gaze. 'Naughty girl, you've seen my little surprise. I wasn't sure if you'd like it. Oh go on take it.' I tried to get up but Katie pushed me by the neck down.

'No,' she says firmly, 'from here.'

It was awkward unwrapping the pretty box, bent over her knee but after a few moments I held the object of my inqusitive curiosisty. I wasn't sure what it was at first. A butt plug. I gulped loudly and the lump at the back of my throat returned.

She took it from my trembling finger. 'Let me put it in for you shall we?'

She didn't wait for me to reply instead she dipped it back in her champagne and I knew what to expect. Moments later having had my panties peeled down and the plug, which felt much larger than it looked, safely inserted up my arse she seemed restless.

'If you're succesfull I'd expect you to wear this when ever I see you.' she says. 'along with the necklace and ankle braclet.' I nod my head. My bottom aiive with a stuffed sensation.

'Good I knew you would and I'm sure we'll get on well.'

'Does that mean i've got the job?' I ask.

'Not quite,' she says pulling up my panties and rearranging my skirt for me as if a mother loiking afte her child. 'I want you to come with me to the hotel reception dressed as you are to meet Anita and give her the good news. I'll then get my secretary to handle the formalties.'

I climb off her lap and wiggle my hips as the plug settles deep withing my arse. 'I can't go downstairs dressed like this.'

Katie looked stern. 'You look fantastic just like a convincing woman which is good as this part is integral to your interview. If you can't brave the outside world in your new cloths this won't work.' Her tone was very commanding. 'You don't think I would embark on this relationship unless I know you can pass as a woman do you?' I said I like a confident pretty girl. You asked me that. I don't want a girl that keeps herself locked away. I have public engagements.'

I shrug my shouldes

'Do this, carry it off convincigly and you will have succesfully past and I'll be delighted to offer you the job. That's if you still want it.'

I nod.

'Now stop being so indecisve and follow me.'

It was funny but before, when dressed in the effeminate trousers and blouse I just felt girlsh but now made-up, wearing the flowing dress, pretty lingerie, hosery, high heels and with the butt plug up my arse I really did feel like a woman.

Outside our room the maid had worked along the coridor but this time she hardly gave me a second glance. My heart fluttered. I concentrated on my poisture which was difficult in my heels, and held my arms like a womans

'Good morning ladies,' she said merrily.

'Good moning,' Katie said in reply. Inside the crowded lift I felt humilated sandwiched bewteen two burley men in business suits.I could smell my feminine scent and my legs rasped as I rubbed my nylons togther. The lift took an age to descend and I couldn't be sure but was fairly convinced that one of the men pinched my bottom but to my surprise I was not laughed at or noticed particularly. In fact one young man gave me a very suggestive look and even winked as he got off on the 3rd floor.

'I see I'm going to have to watch you,' Katie whispers. 'remeber who employs you.'

In the reception Anita saw us before we saw her.

'Well, hello ladies,' Anita says chirpliy walking towards us. Her eyes scaning me from my heels to my hair. 'You needn't say a word. I can see that you got on famously.' she fingered my dress material. 'I knew he would look good in this. Tell me. Are you wearing everything?'

Katie was the first to speak. 'You shoud have seen him, Anita, dressed in those pretty panties and with those sexy suspenders he looked so glamourous. ' My face reddens. 'You've surpased all my expectations. Great job. He's the girl of my dreams.' She gave me a squeeze and winked at Anita. 'I like a cosy armful, don't you?'

I'm not sure if I liked being called a 'cosey armful' but I didn't want to object, especially as i'd past all her exacting requirments

'Thank you,' Katie says suddenly becoming all business like as if concluding a business deal. 'I'll get my secretary to formalise the paperwork.' She shakes Anita's hand and kisses me on both cheeks and squeezes my shoulders affectionately. 'I'll be in touch.'