It was a simple enough mistake, I thought Adam was gay, or at least I hoped he was. He was a friend of my sister, it was a large group connected by a football team they all followed. So home games especially she was out and watching the match, coming home late evening after going on with some of this group for a few drinks to celebrate or commiserate.

Now as I said I am gay, I share a house with my sister who behaves quite laddish, and with me being anything but laddish we sort of compliment each other. There were times when work allowed that I would tag along with her and go to a match, which is where I saw Adam the first time. I didn't speak to him I don't think, but I got a good look at him and admired his good looks and ease with which he handled himself.

After a couple more matches I had introduced myself and tried to be friendly, I was also hoping that he may just be gay because he was even nicer once I got to know him. A few more matches and I think I have a problem, I can't stop thinking about him. And then I bump into him on a weekday evening, we go for drink and get a kebab on the way home. He is just gorgeous, he never seems to have a girlfriend, so my hopes of him being gay ramp up. I haven't had a crush since I was a teenager, but I was having a crush.

When I got home my sister asks where I have been, so I told her. It was then my secret was aired, 'you fancy him don't you?' I went all pathetic and camp, but she isn't heartless, a hug and words of sympathy about understanding how all the nice guys are unavailable. I went of to bed realising that I was just normal in fancying the wrong person and maybe I should just abandon the hope.

Well my sister isn't the most discrete person, I didn't need to tell people I was gay, she did it for me. And you guessed it, she told someone, in confidence she assured me, but soon that one was two and then three, until it seemed everyone must know. Including Adam.

That he knew became knowledge to me when I happened to bump into him again midweek. I felt so nervous worried that he must know by now, and he did. 'I hear that you fancy me?' slipped into the conversation with such ease I was catch off guard, but it was what followed that threw me 'I like my partners to look pretty and wear a dress' I was staring at him trying to work out what he was saying, I was expecting him to go off on a homophobic rant or at least say quite bluntly I had no chance, but he didn't, he paused took a long swallow of beer while I nervously fiddled with a beer mat ready for the crushing blow. 'Can you do that?' Like an idiot I asked 'Do what?' He smiled and laughed a little 'wear a dress and look pretty?' I stumbled over words trying to work out the best ones to answer with, but my mind was working out if I could comply with his wishes just so I could go out with him. I tried a laugh 'very funny, but am just a regular guy not a cross dresser. If you aren't gay just say so, I have been there before' He was keeping eye contact as he replied. 'No you missed the point, I would go out with you, but only if you look like a woman' On the one hand he had said he would go out with me, and then took it away with his conditions that I felt unrealistic.

As you can imagine that more or less ended the evening. I got home in a miserable mood, I had never been rejected in such a way before. Amy might be many things but one thing she is good at as spotting my moods. She had me sit beside her while she hugged me and listened to yet another of my rejection tales. When I had finished and a silence was lingering she quite quietly said 'so what's wrong with wearing a dress, even I have a few'. I turned so I could face her 'but I am a lad!' 'So what' she replied and went on to point out how she wore men's clothes, why not the other way round, and in this age of trans everything what was stopping me from expressing me feminine side? In the end she summed it up 'if you want to go out with Adam then wear a dress. If you don't want to wear a dress then forget Adam' Why does it have to be so hard?

I tried to bring the subject up again two evenings later, wondering if he actually meant it, and could I possibly go out as a girl. She bluntly told me the only way to find out was to say yo would do it, and yes I would look fine as a girl, then went on to list all my 'good' points. Plenty of hair, not much beard, long slim legs, ability to walk camp, small hands. I told her to stop she wasn't helping. It was an away match that week, so she suggested I see how good I looked and then see if I could pass in public. My thing for Adam was overriding all common sense and I agreed, Amy asked my shoe size and said she would get everything I would need.

Saturday, I finished work at midday and went home wondering what Amy might have in store for me. She was waiting for me outside the store, making sure I went home. Then talked non stop all the way home, maybe she was as nervous as me, but possibly more excited than me. Once inside the the house I lost all my clothes and nearly my dignity as she pointed out I am not very hairy for a man. A good point she said 'be easy to get you hair free' as she pushed me into the shower with a lady razor. All showered and smelling of shampoo she passed me unfamiliar clothes. A tight pair of panties, all elastic so it flattened my little man. Next a bra with some very realistic forms inside them, bit of adjusting to make sure they were in the right position. 'Now to make you pretty' she sat me down and proceeded to put stuff on my face explaining what she was doing. My lips tasted different and my lashes stuck together with the mascara, but until I looked in a mirror I knew of nothing else. So I am looking in her mirror as she is positioning a wig on my head, and all I can do is stare at the reflection, I unbelievably look the part. 'Ok stop day dreaming, you look gorgeous. Now let me finish you off'. 'Stockings?' I asked 'Every bloke has a fantasy about his girl wearing stockings, so why not you? They feel good?' I said nothing because I didn't want her to know how much I was liking this experience. 'Right because this is just an experiment, nothing to fancy, a simple blouse and an easy skirt' The blouse was so soft it was luxurious, and the skirt was just long enough to cover the stockings. A pair of plain shoes, some modest jewelry and a squirt of scent and she declared me finished. I stared once more in the mirror at Amy's incredible transformation. 'Now have you thought of a name, can hardly call you Richard' 'what? why do I need a name?' 'Because my dear sister, when Adam asks you what you want to drink, he can hardly say, which cocktail do you fancy Richard. It would be a bit of a give away'

Amy left me to get used to the new version of me, the mirror and the heels were both proving a bit distracting.
In the end I just wondered round the house trying to be busy tidying up.

My next surprise was for Amy to come downstairs looking like a girl for a change, still in jeans, but in heels, makeup and styled hair. She looked really pretty like I had never seen before. 'Sisters are know for their rivalry' she informed me when I kept on staring at her. 'Can't have you looking better than me'.

'Right. If this is going to work you will have to get used to going out, it's what couples do, and you still fancy being a couple with Adam?' This was now real and I was nervous, did I want Adam to see me like this, never mind all those people I didn't know but may well spot me as a bloke in a dress, bad enough being gay in some places, being a tranny could be even worse. 'Well you just have to make people think they are seeing a woman, not a man then' was her simple solution.

'Right then, next step in this plan is to see if you can walk out the front door. So how about I get you a coat and handbag and we see how much you want to be with Adam?' This had been fun, the idea of being with Adam as a girl, the dressing up and disguising the man I really am was amusing and amazing to see, but this was going to be a challenge, walk out the door, along our street of terraced houses wondering how many might recognise me, frightened that strangers might see through the disguise. 'Right you have to do this, I have spent all day prepping for you, so think up a cover story just in case you are spotted, though I am quite proud of how pretty you are.' We agreed that I was a cousin if I was not rumbled, if I was outed then we are going to a fancy dress party.

The door opened and I stepped out, the cooler air hitting my near naked legs, then the click of Amy closing the door behind us blocked my return. 'Remember. Walk upright. Confidently. Don't make eye contact. Just act normal'
'But this isn't normal.'
'Maybe not for you, but for everyone else we appear like a normal women on our way out' So I followed her advice, looking down only when I had kerbs or steps to negotiate. Thankfully the walk didn't last long, but the bus ride seemed to last forever, even though it was only a few stops. Thankfully we were in the anonymous city centre. A bar that was serving food was our first stop, though how I ate when I was so nervous surprised me. Then a walk round, to get me used to being seen, she said, to make my feet hurt I said.

As the minutes ticked by I began to realise that Amy was right, nobody was taking an interest in me, yes people looked at me occasionally but no more than usual. Outside on the street I felt ok but when we went in a shop and had to stand in a queue I felt one or two were staring, Amy just pointed out I was the only one there in heels and a skirt, and people look at dressed up women.

With our mints bought she fancied another drink. I thought we were just looking for a pub that looked ok and walked past a few until Amy pointed at one 'Let's try that on, I've heard it's good'. I didn't have a choice really as she walked straight to it leaving me struggling to keep up with her seasoned walking on heels style.

I caught her up at the bar as she ordered two glasses of wine. 'I'll pay for those' a familiar voice said, I turned round to see Adam stood behind us with a note in his hand. Amy casually said 'thanks', I just stood there dumbstruck as I realised Amy had set me up. 'Thanks Adam, not sure you know my cousin Bella'. He gave Amy a hug then hugged me long enough to whisper in my ear 'You look fucking amazing'. He then lead us over to a table and deliberately sat next to me so we were squeezed into each other on a bench seat, Amy sat across from us smirking as she looked at me clearly not sure what to do but also clearly got myself on a date with Adam.

The conversation quickly became stilted because it was obvious why I was there, but it was still a surprise when Amy picked her glass up, tipped the contents down her neck and stood up. 'Well I'll leave you two to it, I don't think you need my help any more' and before I could get myself out from behind the table, she was gone. I was standing there wearing women's clothes with Adam in a strange pub, I felt panic rising as Amy disappeared. I felt Adam touch my hand 'At least finish your drink' I sat back down, only this time Adam's arm was round me. 'So Bella, you wanted to go out with me, and you have gone to all this trouble to make this date happen, so how about we go to a club and see how the night develops?' How could I refuse, I had wanted this date and allowed myself to get dressed up as he wished, he hadn't rejected me because I looked like a bloke this time, he was actually holding me in a way I wished more of my ex's would have done. 'So you are happy to be seen with me looking like this?' He gave me a squeeze 'more than happy, when I said I would go out with anything in a skirt I was maybe not being to honest, what I actually like are feminine boys dressed in skirts. Let's just say it is my kink, I like men but don't want to be an equal, I also like how some boys can look so pretty and behave like a coy girl'

I was sitting there fiddling with the hem of the skirt, pulling it down and feeling self conscious about showing so much leg. The silence was dragging and I felt the need to fill it. 'So you are sort of gay, why have I never seen you in any of the gay pubs?' 'Oh that's easy, I don't like all that macho stuff, and like I say, I don't want guys chatting me up, I want to take the lead. So drink up, I think I should take you to a club I like that plays great music and the bonus is girl's get in free' I was liking him even more, some gay men just want sex, Adam wanted to spend the evening together, I tried one more question 'so I guess you like being the top' 'obviously, but only with a willing partner who asks me' I turned to look in his eyes 'are you this nice to every girl you meet' 'I try to be, but then there aren't many girls like you so I don't get much chance to find out'. And then he kissed me, a gentle meeting of lips before he got up, took my hand and led me out of the pub.

'Come on, this might be your first time being a girlfriend, who knows it might be your last, but you look great and I fancy spending time getting to know you' I didn't know what to say, I didn't fancy just walking away, besides him being a perfect gentleman it was no getting late and the thought of walking about looking like this on my own was not a great option. I took hold of his hand 'So where is this great club that play fantastic music?'

By two in the morning I had learnt that dancing in heels is something I had not mastered, I had learnt an awful lot about Adam and why he disguises his homosexuality behind trans people. I had also learnt that he was a great lover. I had come to the conclusion that if he asked me out again it would be worth getting dressed up for him. I had also realised that I need to plan better, because come the morning I will have to get home and will only have the clothes I was wearing when I followed Adam to his house. Just how was I going to get home? Much to my surprise I had few qualms about putting the skirt back on, but before a next time I had better learn how to do makeup, just so I can feel more complete as a woman and girlfriend.