This a story of how a mate of mine went from having a pint with me after work, to drinking things like white wine and soda with me on a night out

I was in the pub having the usual after work drink before heading home for my take away tea, when Steve starting chatting about an unusual incident he had had that afternoon.

Steve is a plasterer and so when he starts a wall he ends up having to finish it, no leaving it and coming back tomorrow, so when the customer asked if he was nearly finished and what time he would be done, Steve explained how it was likely to be a good two hours before he was ready to leave. The customer a pleasant enough bloke who I had done work for in the past, became flustered and paced about a bit so Steve says, the customer then said something like 'It's no good I shall have to get ready or I'll be late' Steve thought nothing of this and got on with his work, but aware that the man was spending a long time upstairs getting ready. Now comes the good bit. Steve says he was tidying up the tools when he saw a rather striking woman come down the stairs, at first he thought she had got in without him noticing and had been to see John the customer, about to say sorry and step to one side, he picked up on the general image of the woman and realised that it was not a woman but John. He still said sorry and stepped to one side, the 'thank you' in response confirmed this good looking woman was in fact his customer and was now 'ready' to go out. Steve says he made a polite but quick tidy up and left, his next stop being the pub and our chat.

His dilemma now was that he was meant to go back the next day and finish the room off but he was embarrassed about what he had seen. I tried to be helpful and say it is work, that John would have said something if he was offended by Steve's actions, then as a tease I suggested that if John was that good looking why not ask him/her out. He choked on his beer.

I heard nothing more of Steve for a week, so when I did, I asked him how the job had gone. He had indeed finished the job, and been paid. I pushed a little farther asking if John had said anything. Steve told me John had not said anything as such at the time, and it was not John but Jenny, 'oh' I said and asked for more detail. Steve had turned up at eight the next morning as usual but instead of John letting him in it was Jenny, dressed in nightie and wrap. Now this was getting interesting. He says he went in and started to set up for the next part of the job, Jenny brought him a cup of tea and asked if Steve had any objections to the way he was dressed. I can imagine Steve stumbling over his words as he said he was fine with him/her dressing however they liked and just got on with the job.

Mid morning and Jenny is still about and makes Steve another drink, this time Steve says in a smart trouser suit, silk blouse showing enough chest to imagine what is down there and the reddest stilettos he had ever seen. 'Still a looker?' I asked 'Oh yes' he confirmed. Steve was then left on his own to get on with the plastering as Jenny was going out. He made some comment about how John, sorry Jenny must have some balls to go out dressed like that in broad daylight, he could never imagine doing anything like that.

Late afternoon, Jenny returns with some shopping, Jenny makes him a drink then asks if Steve minds doing a favour, Steve says 'ok' and Jenny says she wants his opinion as a man on a new outfit she has just bought. Steve has agreed to this but worries what he has let himself in for. Fifteen minutes later he says there is a knock on his door and there is stood Jenny in a black and grey dress, virtually nothing to it he says, a short black under dress with a see through grey dress over it, barely black tights and towering black heels. Jenny asked him what he thought, but he was lost for words, this was a woman to lust after but he knew it to be a man, I knew he would be confused, Steve said he opened his mouth but could not think what to say and just stood there, Jenny said that was a perfect reaction and went off to change once more. This time into jeans and a shirt Steve said but I guess after all he had told me, it would have been a blouse. Then when he is finished Jenny makes him a coffee and pays him, but to confuse the poor man further asks him what he felt about having Jenny about instead of John. Steve apparently said it made no difference to him, and then for some reason said the tea always tastes better when made by a woman.

Anyway I rather expected that to be an end to the story, I had done the electrics a while back and thought the house must be pretty much renovated by then, I was wrong. A few weeks later Steve told me that he had been asked to do some more work at the house, I asked if he was taking it, he said yes, so I asked him to keep me informed if anything interesting happens.

I saw him after his first day and asked how it had gone. He said the first cup of tea was of Jenny in nightwear, then John reappeared and went out for the day, coming back late on. But before he left Jenny was back in a skirt and heels. Over a last drink Steve found out that the short dress he had viewed had indeed been a big success according to Jenny, Steve was clearly getting more comfortable with this person and asked if it was for a special occasion, Jenny said it was to celebrate a first anniversary which Steve took to be of a romantic sort. I asked him how he felt about such things, he surprised me by saying he would take her out if he did not know the truth, 'and seeing how you do know the truth?' he went all flustered and said something about the plumbing being all wrong and it would be awkward if it got all hot and sexy. So I told him girls like Jenny who like men have it all that worked out, to which he blushed some more. When we parted I found out he would be at the house at least two weeks doing various decorating and finishing jobs and flippantly suggested that he ought to be careful Jenny might have him under her spell by the end.

It was two weeks later that I saw Steve again, he could not stop as he was going out, 'anyone I know' I asked he just said 'yes' and was gone. Later the next week I got a full run down of the evening but not before I had pieced together his previous two weeks. Steve says Jenny was about most of the time only once did he meet with John. It seems Jenny kept Steve supplied with drinks and work for a couple of days, then as they were getting used to each other Jenny asked Steve if he was offended by Jenny being a man, Steve must have said not because he somehow ended up agreeing to going out with Jenny the day after to a Mexican restaurant. He said they had a great time, at first he was nervous that people would make comments about Jenny, but even though he knew, it seemed no one else picked up on the fact that they were in fact both men. After a while I could tell Steve was getting a buzz from being out with Jenny from the way he talked and the news that they had been out more than the once. I asked about the anniversary, it was not a romantic year like I might have celebrated but for Jenny it was a year since her first day out in the world as Jenny. And the sexy dress, Steve told me that was Jenny going out on a first planned date with a man, 'oh' I said 'It did not last the night, he was a knob just wanted inside her knickers' I paused to answer 'but in a dress like you described what did she expect?' 'My thoughts exactly' he agreed.

It appeared Steve had been working hard through the day and busy at night as well. They had been for meals out, had a drive in the countryside, gone clubbing one Saturday, all the things I would expect to do with a girl if I had one. When I left and suggested he could keep me informed, he replied that he was not sure how often he would make it to the pub in the future, I just said 'Jenny' he nodded a yes.

A week or so after that I needed to see Steve and ask him to look at a job, so on a chance I drove past the house where I knew he had been working, and I was in luck his van was outside. I knocked on the door and was greeted by a rather good looking lady, her cream dress covering a great figure. 'I am looking for Steve' I hoped this was the right house as the woman did not look like a drag queen. 'Steve' she called 'for you'. Steve came to the door, I forgot all about the work I wanted him to do, 'Is that her? Jenny?' 'yep' 'bloody hell Steve you sure she is you know not for real?' 'yep' he said with a big smile. I now knew why he was not at the pub that much lately, 'and the other you know what' he acted dumb 'what?' 'the plumbing' I asked 'oh that is fine, like you said she is not the first to be made that way' I must have looked bad because he asked if I was fine, I was just thinking about them together and having trouble thinking of Jenny as anything but a girl. In the end we got round to the reason for my call and asked if I would be seeing him at the pub, he said maybe which I took as a no, the woman stood nearby was a clear draw for any bloke. As I drove away I was shocked but not surprised to see Steve walk back into the house and Jenny who was standing at the door give him a peck on the check as he passed her/him.

Well I never saw Steve at the pub, so the next time we met was when he plastered over a job I had been doing. I found out quite quickly that Steve and Jenny were a couple of sorts, Steve was spending a lot of time round at the house even though it was finished, he was still going round for meals and the company he said. He asked about my love life and I told him it was non existent, which is a surprise to no one really as I feel awkward with women. At the end of his working for me I took him out for a beer and just chatted like old times, but very quickly it was clear he had to be off, Jenny had a meal waiting for him, so I was down on the priority list.

It must have been a month before I saw Steve again, he was shopping with his 'girlfriend', and if I had not been told the person with him in a long top, leggings and high sandals was really a man I would have been non the wiser. We said hello, Steve introduced me and she shook my hand letting me see the fantastic long red nails. We chatted for a bit then Jenny suggested we meet up for a drink when we were done shopping. So half an hour later I am drinking beer, Jenny has a lime and soda, Steve is on gin and tonic. Since when I asked, since I wanted to loose a little wieght. Jenny was as nice as Steve had told me and we got along fine, but though I took them to be a couple they seemed rather distant somehow.

Next thing I found out was that Steve had moved in with Jenny, which meant Steve was not rushing to get there of an evening and was able to join me for a drink after work before going to his new home for a home cooked meal. He was still not drinking beer though, diet coke mostly which took some getting used to.

Some six months after he moved in with Jenny I was working with him for a week and got a new insight into the life of Steve with Jenny. He had not cut his long hair in years but now it was well groomed I noticed, then I saw the ear studs but said nothing. On the third day he was stretching up and his shirt rode up exposing his back, imagine what went through my mind when I saw what I suspected to be a pair of pink thongs nestling in his bum checks. On the last day he was late and clearly suffering from a late night, and when I got a good look at his face those dark eyes were not just bags, he still had the remains of make up on them. I had a quiet word, something like 'go and look in a mirror', which he did and came back telling me he had been playing around with Jenny the night before and she had got him to try on some mascara. I thought there was more to it than that, but did not want to confront him with any of the evidence I had seen that week.

Well the job over, and for whatever reason I did not see Steve for a few weeks, but I did see Jenny in the supermarket and was still in shock as to how this woman could possibly be a bloke under the clothes, he behaved just like a girl as well, so maybe I figured it went deeper than what you wear. I mentioned that I had not seen Steve for a bit, she told me had been busy, and left it at that.

Three weeks later I was to find out what he had been busy on. I was in the supermarket once more and saw Jenny picking out some fruit so went over to say hello, at first I did not notice the woman beside her but eventually twigged that they were together, then I took a longer look at her friend, and I guess my face said it all. It was Steve! His hair was curled, face made up, a nice flower pattern top, plain cotton skirt, tights and heels were making the immediate recognition difficult, but my reaction was enough for him to freeze and tell Jenny it was a bad idea and he wanted to go back home. I felt bad if totally out of my depth and wanted to make things better and started saying how I had taken an age to work it out and how good he really looked, though why I should be telling my friend this was beyond me. Jenny had hold of his arm and was doing her best to calm him as well. After a few minutes I felt I could do nothing more and left them to do my shopping, but was constantly on the look out for my friend. I even sat in my car watching for them coming out just so I could see if Steve was as good as Jenny.

And he was good, not as good as Jenny, but she was I guessed fulltime whereas for Steve it was only a part time thing. Embarrassingly I was spotted and while Steve loaded their car, Jenny came over to me, got in the passenger seat, I was amazed at how much thigh was on show and the perfume smelt fantastic.
'Hi, get in why don't you'
'Look Greg, it is Greg isn't it. I know you are a good friend but please keep this quiet, don't go telling your mates, Stephie would be mortified if it got out'
'Stephie?' I said
'Yes the name she uses when not at work, please say you will keep the secret'
What could I say but yes.
She lent over kissed my cheek and told me I was wonderful and Stephie would be grateful.
All I could think of was how long has it been since I had been kissed by someone so good looking. Too long.
Before Jenny had made it back to the car I had sent a text to Steve telling him I was OK with everything and not to worry. I then went home mulled over what I had witnessed and just could not get the image of Steve out of my head.

If I thought that meeting would be forgotten easily I was mistaken, I kept on remembering how good Steve looked as a girl and thinking if I would ever manage to talk about it let alone see him dressed that way again.

Steve never happened by the pub after that meeting, but I did bump into him when I was picking up bits from a merchants yard, after a few regular pleasantries I could not stop myself saying 'you had me fooled the other week you know' he blushed, 'I had guessed before, you still wearing pink undies?'
still blushing 'how do you know that?'
'On that job we did together, they showed over the top of your jeans'
'Ow hell, I told her they would show'
'Are they comfortable'
'Well yes'
'So why worry'
'Dont want you all thinking I'm a sissy'
'Only I know and I just know that you are my mate Steve who happens to look like a bloody good woman when he wants too' he was still blushing 'anyway I had better be going, work to do'

I could not believe how sympathetic and caring I had sounded when all I wanted to say was 'dress up again'. This thought was totally unexpected and took me a while to sort out that I had fancied my male mate when he looked like a girl. This however was not an instant thing, it took a while before I was up to mentioning the incedent again, and when I did it was a fumbled job as I was not prepared. I bumped into Jenny and Steve at the supermarket, Jenny was looking perfect, summer dress and heels always look good to me, Steve was in jeans and trainers, so after the hellos I clumsily said something like, 'Jenny you are looking great, Steve you are letting the down side in those jeans' Jenny leaned towards me and said thanks for the compliment, Stephie was not feeling to confident in the daytime for anything other than a unisex look. So I asked when Stephie would be getting dressed up next. Jenny smiled at Steve and got a agreeing nod, then told me that Stephie would be in her full glory that evening. It was now me who blushed as I said 'oh?' Then with a smirk on her face she invited me to join them, all I could do was stumble over my words. Still smirking Jenny lent over kissed my cheek and said 'See you later then' not a question but a statement.

I spent the rest of the day in total confusion, should I go, should I stay away. The bar they had told me to meet them in I knew was a gay bar and one I would never have gone into ordinarily, but then I had never wanted to see Steve as Stephie before. By six o'clock I had got myself ready in what I hoped was a fashionable t shirt and my best jeans. Eight o'clock and I was sat in a corner clutching my pint and watching the gay men being very gay and making me feel like a fish completely out of water. I was just beginning to think I had been set up when I saw Jenny walk in, she was in the black and grey dress Steve had once described and looked so hot I could see why he was taken in by her. Then I spotted Stephie, head of hair full of curls, a short black top covering a rather large chest, demin shorts hiding his secret very well as they were so tight and fishnet tights leading my eyes down to some strappy spike heels. He was a fantastic sight, I bought them a drink, Baileys, how girlie I commented, 'Cant drink pints looking like this' I had to agree.

The evening was great fun once I had relaxed. They took me to a few other bars and seemed to be quite familiar with many of the other people there, Jenny I half expected to be a bit flirty but was surprised to see Stephie chatting with men and behaving quite easily with them with lots of touching that I was unfamiliar with in the old Steve. What was nice, was to walk along the road between bars with a hot girl on each arm, a totally new experience for someone not at ease with women, but these women were at ease with me it seemed. Late on I noticed Jenny had disappeared leaving Stephie alone with me, I asked where she was, it was then I discovered the two were not a couple as I had thought, Jenny was off with a man she had picked up and Stephie was looking after me. So for a reason I don't know I put an arm round his bare waist and said it was just the two of us, Stephie nodded so I asked how I was going to be looked after. Being close enough for the breasts to be pressing on my chest already, she asked if I needed looking after, then put a hand on my shoulder and pulled me round to face her. I must have been totally relaxed as I told her how hot she looked and did not flinch when my mate kissed my lips. The kiss got deeper and more passionate until she broke and suggested we go to another bar.

I just could not believe what other people would be seeing, which was me, the most inept girl chaser, with a great looking girl holding my hand, I was in heaven. In between our kissing I found a little more about Jenny, Steve and Stephie's home arrangements. Jenny was living virtually fulltime as a woman, doing online translation work which meant she hardly ever needs to meet the customers, Steve I knew was still doing his plastering, but when he was at home relaxing or going out then it was as Stephie more and more. As to what I thought about them being a couple, well they had a very open relationship, both have a double bed, but Jenny likes Steve in bed but Stephie for company, so tonight Jenny was looking for a man as Steve was Stephie and not in the running. I asked if it was a problem, Stephie said not, as Steve he gets to have sex with a hot looking girl, but if he fancies it, Stephie can enjoy being on the recieving end if the desire and a good bloke are there. When I asked if he/she was gay, the answer was no, when with Jenny it is as a man, when as Stephie it is as a woman, I could understand this as I was quite happily getting randy with Stephie who I had no problem thinking of as a woman, especially when she pressed her chest against me and ground her hips onto my erection, as long as I kept the memory of Steve who I would never be intimate with, out of my head.

Come midnight I suggested we get a taxi back home, then outside Jenny's house Stephie asked me in for a coffee, I accepted even though it would mean a few mile walk later, I just did not want to let the evening end. Inside the lights were on and it was clear Jenny was entertaining someone in the lounge, so Stephie took me through to the kitchen and made the right moves so I thought I was going to get a coffee, but while the kettle boiled we started kissing again, then heard Jenny giggling her way upstairs. I was lead to the living room to see enough disarrayed clothing to imagine what had been happening, so instead of settling down in there, Stephie suggested it was too messy and maybe I would like to see her room. Well I was shown into the bedroom and told to wait a minute. Within seconds Stephie was stood at the door having changed into a very sexy sheer baby doll outfit. I will leave your imagination to work out what happened next. What I shall tell you is that I shared my coffee at ten o'clock the next morning with a still sexy looking Stephie, a fully dressed Jenny and a man I found out was called Pete and stopped over from time to time, a banker of some sort he tried to explain. It was all rather awkward for me, I had never had the morning after situation and definitely not with another couple who had clearly been up to the same tricks as me.

Eventually I left and went home, but not before Stephie had continued the girlfriend role and had made it clear she was happy if we went out again, but as I said 'best not broadcast our activities too widely'

Mid week Steve saw my van parked outside a job and called in, he looked completely different, I certainly did not fancy him in his work clothes even though when I looked his eye brows were a little too thin and his nails a bit too neat. But even though I was not looking at Stephie, it was Stephie that I invited out on Friday night.

And so began my longest ever sexual relationship, it is now a year on and I see Stephie on a regular basis, I see Steve ocassionally, but it is Stephie that appeals to me. Some weekends she stops the night and it is very odd to now have knickers drying in the bathroom alongside my boxers. I have got used to waking up with a sexily dressed partner lying beside me, more often than not having enjoyed some great sex previously. Where it goes from here I have no idea but for now I am happy to let the situation continue for as long as possible.