Trying something new

It only started with me sitting waiting, all ready to go out and Fay looking great as she fastened her ear rings on. An idle comment can have major consequences. I only said 'your dress looks great, those underskirts that make the skirt fill out are back in fashion, they always looked good in those old films.'
Fay smiled at me, 'yes it's new, I bought it last week, glad you like it.'
And then the comment that changed everything 'what does it feel like to wear? I mean the skirt is so full and the underskirts must feel different against your legs.'
'It's hard to say because you wear nothing like it so there is nothing to compare, I'll tell you what, if you are really good to me tonight I will let you find out for yourself.'
Now when Fay suggests I be good it is not a warning but an encouragement, meaning that she was feeling randy and wanted to enjoy the evening to the full, with more fun when we got back home later.

At two in the morning I was exhausted and so was Fay, we fell asleep the comment at least my on part, forgotten.

It was early afternoon before we were both up and functioning properly, and we both happened to be in the bedroom when Fay was sorting out her dress from the night before.
'You still curious about how this dress feels?'
'Oh er yes I suppose so.'
'You don't sound so sure as you did last night, you aren't frightened by a dress?'
That did it, I was no coward 'Well go on then lets give it a go.' and I lent over to pick the dress up.
'Not so fast, you don't just put a dress on, you need to sort out the preparations first.'
'Like what?'
'Like you need a bust to fill the top, and then some nice tights or stockings always make a dress feel better.'
'Oh come on I only need to put it on to know how it feels.'
'You are so wrong, to know how nice this dress is you cant just put it on, its like looking at a motorbike, sitting on one and riding one. to just put it on would be like sitting on your bike, no if you are going to know how nice this dress is then there is no way you are just putting it on.'
'Ok so I get the bike thing, what do you actually want me to do?
A long lingering kiss happened before Fay told me. 'I want you to just do everything I tell you to do, no questions, no being awkward, you be good and I am sure you will like the results.'
Resigned to it now 'ok what's first?'

Soon I was in the shower rinsing off her immac cream and watching my body hair going down the plug hole, I wanted to ask if it was necessary but when I dried myself i knew the answer, yes it was, my skin felt so different, sensitive and smooth, even more so after I moisturised. The satin wrap she gave me felt amazing now as I made my way into the bedroom, I thought that it would be put on the dress next but she guided me to her vanity and made me sit down. 'Now remember be good for me.' she repeated and then plucked a few eye brow hairs out, 'just needed to be a little neater, now lets see what features your face has.' She skillfully brushed powders onto my skin making me feel pampered, next she surprised me with some of her special evening underwear and told me to put it on, knickers were no problem besides getting my stirring penis to settle inside, the bra was trickier so she came round my back fastened it and kissed my neck 'you look great already.'
'Just wait till you get the dress on.'
From somewhere she produced a wig and secured it over my neat manly cut, brushing it into a style she wanted before spraying it with lacquer to fix it. Next rolled up tights pushed into the bra cups gave me a chest I had never had before. I could sense that I was looking more female with every action, but it was as I rolled the first stocking up my bare leg that I actually felt how nice this was, the second confirmed it and the tensioned suspender running over my arse just helped me along.
'You seem to be liking this' Fay smiled as she looked down at my extended knicker front. I dared not answer because I was not sure I should be reacting this way even if the evidence was there for us both to see. 'Nearly there.' She handed me the underskirt showing me how to step into it, my first skirt of any kind and I was not having a problem with it. 'Ok before you get the dress just a few small extras, and then we let you find out what this motorbike is like to ride.' A squirt of the scent I liked on her was evaporating from my skin as she clipped some pendant ear rings to my lobes, those hurt. 'I hope these fit, they are a bit big for me but you are not that much bigger than me, are you?'
'Yes heels, it would be like riding without your boots, it's part of the package.'
They were tight or snug depending on your point of view. 'Right you ready?'
'As ready as I ever will be.'
'Lift your arms and put them through the sleeves while I stop it ruining your hair.' She carefully maneuvered the dress down my body until it was sitting about right, then with a swift action I felt the zip rise up my back and pull my stomach in. A bit of fluffing out of the skirt and a necklace hung round my neck, she took a step back and smiled, 'oh silly me I forgot lipstick.' Carefully she applied the nice cream to my lips. 'Now come over here.' she took my hand and lead me to the full length mirror we have, the skirt was swishing round my legs, my free hand was caressing the smooth skirt as it moved. 'Now I think for a first time, you look rather good as a woman. Tell me how does the dress feel?'
'Er. I. Er. It is very different.'
'Obviously, but how does it feel, smooth, rough, tight, loose?'
'The dress is very nice and smooth, but you know I like your silk clothes, the underskirts feel like they are brushing my skin ever so gently.'
'Ok so walk about a bit and feel it moving.' I walked to the door and back, taking another look in the mirror watching the skirt move round me 'So you know how it feels, what I want to know is how it makes you feel, because you look amazing.'
I thought for a moment 'well the heels make me feel a little awkward, but I certainly feel different.'
'Nice different or unpleasant different.'
'Nice different.' I confirmed.
'Well in that case might I suggest we go downstairs and get something to eat and maybe watch a film.'

We ordered a Chinese and ate it with a bottle of wine, Fay remarked how nice it was to spend a night in with her girlfriend and how it would be nice to do it again, but next time both of us getting dressed up for the occasion. I just smiled and picked up another piece of chicken, thinking 'next time! does she like this?' We relocated to the sofa and watched some mindless rom com letting the wine relax us until it finished and Fay came out with another comment 'I know you like skirts because it allows easier access to my pleasure zone, well how does it feel to be in my position?' as she spoke she deftly slide her fingers up the inside of my thigh. 'Someone is enjoying themselves.' she said stating the obvious as she hit my pleasure zone and pressing her lips to mine, ' I must teach you how to do lipstick, yours has all worn off.'
'Is that necessary?'
'Oh you have so much to learn about what wearing a nice dress involves.'
'Do I?'
'And one thing to learn is just how sexy a dress can make you.'
'Oh' I was not expecting that.
'Not sexy in the way the usual way, no you make me want to take you not you taking me.'
'Oh come on, sexy woman that you are, I want you to be a sexy woman in bed now.'
This was getting out of my comfort zone, what was she suggesting. Then I discovered that Fay was not quite all she had lead me to believe, before we met she had enjoyed other women and assured me that I had got her randy, my next revelation was that hidden at the back of a drawer was a toy she had not let me see before, and until later that evening I had not known about. She left me to tidy up the glasses and plates before I followed her upstairs.

I was already aroused by her earlier attentions and to find her in seductive clothing only encouraged me, I started to get undressed but she soon put a stop to that and showed how it is to be made love to from the other side. I was aching to go inside her or for her to touch me but she refused and massaged my rear entrance instead, slipping a finger or two in, which I admit to quite enjoying, there was a brief pause while she said she wanted to introduce a toy, which is when I discovered more of her past and something of my future. She rolled over to face me once more only this time she had a cock to rival mine between her legs. 'on top or from behind?' she gave me no choice as to whether or not I wanted it, she was going to enter me one way or another, and I was putting up no resistance to her advances.

Half an hour later I was removing my make up and putting soiled clothing in the wash. My outer appearance would soon resemble the person of the night before, however the inner me was changed forever, I had enjoyed wearing a dress, looking pretty, being sexy, I had even enjoyed Fay fucking me until we both came in a fantastic orgasm. I would certainly be having more girls nights in with my girlfriend.

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