Match Making
by Lauran

I have mostly normal boring friends, but a few fall outside these boundaries. Two such people are Jerry and Phillipa.

Both are seemingly confused individuals who are unsure what they like in a partner, Jerry says he likes women but spends all his time in gay bars where he says he feels more comfortable, and has had a few relationships with men. Whereas Phillipa fancies women but will not admit to it, so goes from one man to the next each time getting all excited that this is 'mister right' only to say a few weeks later how wrong she was.

Well Jerry had split from his most recent partner a few weeks before I set up a blind date with Phillipa. I thought they might hit it off, mostly because Jerry when it comes down to it, he is such a girl, and Phillipa is the bossy controller who would look after Jerry; in my mind it was perfect.

I had felt a bar in town would make a good meeting place, of course Phillipa turned up at the time I said I would be there, but Jerry got himself mixed up with timetables and arrived late, rather as expected. Anyway after I had introduced them and they had accused me of setting them up, which I denied, but called me a schemer who one day will be set up myself. After a shaky start I managed to keep the chat going, we had a meal then went our separate ways.

It was a couple of weeks later when I saw Phillipa, I had to ask if she was seeing anyone, and admitted to having gone out with Jerry a few times, but he was hard work. She then told me his faults, which is usually a prelude to a break up, but underneath I could tell she liked him. She let slip how much she liked him, by saying that he would need to get some better clothes that suit him, and she was going to work on getting him organised. This seemed quite positive, and as I gave her a kiss, I said I hoped it worked out well; her reply was 'I hope so too, he is sweet'

The next time I bumped into them Jerry had lost his T-shirt and jeans look, instead he was wearing loose cotton trousers and a nice v-neck jumper. We kissed and I told him he looked nice, Phillipa was glad I liked the new look and told me they were on a diet. She was starting to control him I thought, but that is what he needs she would say.
I had lunch with Jerry later in the week, I wanted to know how it was going and if he was happy. Again was he dressed nicely, only this time it was a lemon jumper and jeans, which he would have had to pour himself into they were so tight. We chatted about general things, then I turned it to Phillipa, he was happy I could tell, he said he was in love and thought she loved him. I asked him about the clothes, he just said that he was rubbish with clothes, which was why he did the jeans and t-shirt before, but Phillipa was great she would find things that looked so good and felt lovely. When I asked about the jeans because there were no obvious underpants and they had a flat front, he admitted to wearing a girdle and that Phillipa does not like a bulging crutch look. So with my questions answered I left to wonder what else besides a girdle and lemon jumper she might get him to wear wear in the future.

Phillipa rang me and asked me out the next day. Jerry had talked about our meeting and she wanted to make sure I was not jumping to conclusions. So I told her how happy he seemed, and that he loved her. She blushed at that and said she knew. Then she asked what I thought about how he dressed, I said how nice he looked recently, which pleased her.
'He's not too effeminate is he?' she asked, I replied telling her he was such a girl at heart effeminate suited him. 'Oh that is good then, it was just I thought his hair would look good with highlights, what do you think?'
'Yes, but it needs tidying as well, it looks as though it has not been cut properly in years'
'I know' she confirmed 'He says he find barbers difficult, so I was going to suggest a unisex salon' I smiled at her
'When it is done let me know, I would love to see how it comes out' to my surprise she said 7pm Saturday.

So at 7 pm I found them having a coffee on the High St, at first I did not recognise them, Jerry had lost his pony tail and had lovely straight hair parted to the left a fringe sweeping across and behind his right ear, the dull mousy brown was brightened with silver and gold streaks. As if this was not enough he had a black shirt that shimmered as he moved and baggy linen trousers. He looked great, and as I leaned over to hug him told him so, and asked him to stand up and give me a twirl, which to my surprise he did. I then noticed Phillipa, she was different but not so much, her hair was slicked back, no make up (not that she ever wore that much) a plain cotton shirt and brown chinos. It was great to see them with their new image and looking so comfortable. I had a coffee with them and we chatted aimlessly. Then as we got up to leave Jerry picked up a black handbag, I suppose I should call it a man bag, but it looked so like a clutch bag, he noticed me looking at it and confidently told me the trousers did not have pockets, and if they did filling then with money, phone etc would spoil the line. Well I thought, that is not something you expect to come from a man is it. But then as we walked to find somewhere to eat he linked arms as a girl would, Phillipa just keeping her hands in her pockets. All I could think was, how right I had been, they were meant for each other.

It was Monday the next week I had a call from Jerry, obviously feeling down and wanting to know if he was right for Phillipa, if I thought his new look was acceptable, did he look like a girl or a man? I tried to keep him calm telling him they were well suited and had never seen either of them more at ease in a relationship. As for the image, he should wear what he is comfortable in and he likes wearing, but comfortable does not always mean easy rather what he can feel relaxed in. Apparently someone at work had teased him about his new hair, and ten compliments can be undone with one sour word. So I told him to think of Phillipa and ring her.

Next I had a call from Phillipa worried by Jerry's call, she needed to know if they were right together and if Jerry was being too effeminate, I asked her if she had used her new look for work. Indeed she had and it was going down well, she was finding people reacted differently, it seemed getting things done was easier if you looked a bit butch. As for Jerry, I told her to let him find his feet; a new hairstyle always takes some getting used to for the person and those that see it. She seemed satisfied with my words and rang off saying she would be in touch.

Phillipa had said she would keep in touch, but my texts fell on deaf ears for at least three weeks. I was getting worried about Jerry, as he was not responding either. Then Jerry bumped into me quite by accident, as usual he looked pretty, and when I asked why he had not been in touch he said they felt they were using me too much as a support for their relationship and they needed to work things out between themselves, well that was the short version. So I insisted he meet me later for a take away and fill me in on what I have missed while I was not 'supporting them'.

He did come later, and he had a different outfit on, something the old Jerry would never have done. Now he had tight hipster jeans and a lilac slash neck jumper. I told him how nice he looked and how much I valued his friendship. He talked about how one person teased him at work, but how the women in particular seemed to be more relaxed around him, the men he had never really felt at ease with still had the same effect, except for the one that was horrible, and another who Jerry was sure was trying to chat him up. He also told me he was going to the salon again, when I asked why he said his hair needed tidying and the roots doing, besides he had liked the attention he got being pampered. It was about this time I noticed how nice his nails were, not long, just neat and manicured, he blushed when I pointed out how nice they were, he just said he was bored watching the TV a week ago and started filing them and one thing lead to another. What he did not say was how did the polishing kit happened to be in his place to start with. He left early because it was work next day, and I made him promise to call at least once a week, and Phillipa had to call me before the weekend.

Phillipa was a stunner next time we met, her hair was shorter, like a feminine boy cut, side burns, cut around the ears but with soft edges. She was never big chested but she must had had a sports bra on to be that flat. I did not know whether to hug or shake hands. She looked happy and told me how well they were getting on, apologised for keeping a distance, but they felt stronger now. She had got promotion at work, a move up in charge of a section, apparently they liked her no nonsense approach, she thought they chose her because the men did not feel she was using sex to get things, as the other women had turned up in low cut or short dresses for the interviews. When we discussed Jerry she went a little dewy eyed, still in love I thought, I asked how she coped with him being so girly did it not attract comment. She truthfully told me she would have him no other way and had bought him clothes to try at first but now he was buying his own, on his own, and promised to get him to come out at the weekend in his latest outfit. I said I couldn't wait, which was an understatement; I wanted to know what Jerry would wear that was going to be more OTT than I had already seen. I would just have to wait.

For all my eagerness at meeting them, I was delayed and met them later than arranged. They were in a bar with a dance floor and enjoying the dance when I eventually spotted them, which had not been easy. Phillipa was so butch, combats, boots and a loose jacket hid everything female, whereas Jerry was being feminine, as she had said he would, his hair had been treated to a session at the salon, still streaked but wavy in a scrunched up way with clips to hold some of the longer fringe hairs in place. If this was not enough, and it was the outfit I had come to see, he was in a pinkie/brown roll neck top, with cream silk trousers that were tight around his groin and arse but then flared out to an enormous hem, and though I did not see them till later he was wearing brown kitten heel shoes with pointed toes. Absolutely wonderful I told them when we found a drink and a quiet corner. 'You like it?' they asked 'I love it' I replied 'the hair, the clothes, the look, just brilliant'
We had an excellent night, I got asked for a few dances, but mostly I danced with my friends. I kept reminding them how lucky I was to have such wonderful friends.

Next morning I woke at Phillipa's place, sleeping on the couch just in my underwear. Barely awake Jerry put his head around the door to see how I was, and then stepped in with two coffees. It took a moment to register, but he was wearing long lilac silk kimono wrap and without any comment sat opposite me, wrapped the silk over his shaved legs and asked how I was. After a bit he explained he did not have a dressing gown but Phillipa had this one she let him borrow when he stayed over. Maybe I was not fully awake and the restrainers were not on my tongue, but as we chatted it slipped out about how easy he could be mistaken for a girl, he said it happens all the time, so I tried to find out more about why he was wearing such feminine clothes, like a silk kimono. All he would say was he enjoyed looking that way, I asked about how his crutch looked anything but male and neat like a girls and how it must be uncomfortable, he admitted it was a bit, but Phillipa liked a flat front and the clothes look so much better flat, which I could not deny. When Phillipa turned up in a rugby shirt and jeans, I knew this gender bending was not for show, but I would like to know how far they would go, but kept that one to myself.

The times we meet after that they were far less OTT, but still most definitely butch and girlie. Jerry seemed to be spending more and more time at Phillipa's, so it was no surprise to find out Jerry was moving in and as I had a car could I help. Of course I would

It started with a trip to a tip, then a more telling one to a charity shop, all of Jerry's pre Phillipa clothes were bundled up, and what I thought were his favourite jeans and t shirts were given away. Then we had to remove all his new clothes, I was impressed that a man could have so much and such a quantity of soft and luxurious fabrics, that was without thinking about the colours, this was definitely not a dark suit wardrobe, but the most interesting find was that he had more than the one pair of heels I had seen, he also had cowboy style boots with a block heel and some colourful flip flops with a wedge heel, not high, but high enough. All I wanted to find was a dress to satisfy my nosiness, but he either did not have one or it was well boxed already.

And so a week later I had Jerry alone one lunchtime, having a coffee when I felt bold enough to ask if he would ever go completely girlie and wear a dress. He was quite shocked by the comment, but I carried on by reminding him of the things he was already doing, the silk trousers, shaved legs, streaked and styled hair, manicured nails, need I go on I asked. It was then I noticed how well defined his eyes were, and added, mascara? 'Yes' he replied 'it makes my eyes look so much better, don't you think?'

I had to see Phillipa, so I 'accidentally' meet her after work. After a pointless chat, I asked how far Jerry might go, I mentioned all the things he had changed, and she loved them all, the smooth skin, the elegance of his hands, the way his eyes looked adding that he was going to ask the salon to pluck his brows next time he went.
'So when do you get him in full girlie dress?'
'Oh I don't know, but I shall not be surprised if he comes home having seen something he likes, and asking what I think'
'and what will you say when that happens'
'depends if it looks good on him'
I left it there and went off wondering just how girlie Jerry would become.

Our Saturday nights out were becoming more common, and Jerry was becoming more of a girl, as Phillipa would complain how long it took him to get ready. It was a few weeks since his last pampering at the salon, so I was not surprised to find he had been again and followed through with the brow plucking, but they were thinner than I had expected. The fine eye liner was unexpected as well, fortunately he had only had his hair washed and blow dried, so it was not that difficult to find him in the crowds on the evening. He was once again flamboyant, in silk trousers with a brown sheer top with full sleeves that finished at a satin cuff, and below the satin bow that sat at his neck I could clearly see a chemise, added to which the kitten heels I knew about had become 2" sandals. I said nothing except how lovely he looked, but to myself asked how long before he goes over completely.

I slept on their couch again, and once again had a coffee wrapped in a blanket the next morning, Phillipa was in a grey towelling wrap, and Jerry had satin pjs on, with the kimono covering him. As I had a wash I had a nosy in the laundry basket, there were nice knickers and boxers, some nice camisoles, knee highs and normal socks, nothing that I could say was not worn by one or the other equally, though the camisoles I doubted would be under Phillipa's shirts. Then I heard Jerry outside the door 'is this what you are looking for?'
'Pardon' I said,
'I think you should be less noisy when you start rooting'
I tried to sound confused 'sorry I don't know what you …..' I nearly said mean as I opened the door, but Jerry was dressed in a long gypsy skirt and a matching peasant top, so I temporarily lost the use of my mouth. 'Why didn't you tell me, you look great it suits you' I eventually managed,
'not for work though I think'
'no not for work, does Phillipa like it?'
'Loves it, but says I have to go for the complete look if I am to wear it for going out. So what size tits do you think would look good, and Phillipa would like?'
'Never thought, how much of a statement do you want to make?'
'Well they might as well be seen'
'C or a D then. I suppose you have everything else'
'nearly' he replied ' I need to have a lesson at the salon about make up, and I want to get my ears pierced'
I then hugged him 'I am so pleased for you'

Next weekend we met for a meal, Phillipa not to be outdone was in a neat suit with a collar and tie, Jerry was in the gypsy outfit, but the top was filled with a chest, he had hoops in his ears, his face made up disguising any remains of the man, his neat nails were a delicate pink, and he had gone for black stiletto sandals, and a proper handbag that hung of his shoulder. I knew it would come, but calling Phillipa, Phil took some getting used to, whereas Jerry just stayed the same, though I guess he was spelling it differently.

Over the next months I meet the couple on various occasions, when it was daytime they toned down their obvious alternative gender positions, Jerry would most likely be in linen trousers or hipster jeans with a cashmere top, whereas Phil would be in a suit or chinos as management roles required a certain dress code she said. But of an evening and weekend, Jerry in particular went overboard, certainly he would wear some fabulous trousers and tops, but increasingly he was buying skirts, and of a more sexy nature, but no matter what he wore he was always a lady away from work, with make up done to perfection.

One night he was dressed in a silver tube dress that was so clinging it showed the suspender clips through the fabric, as always he looked brilliant, and after a few drinks I asked if the ever thought of taking it further with drugs and surgery, the look of shock was not expected. Phil who had been fondling Jerry all night was first to say 'Oh no, we couldn't loose those bits, might not be big, but quality counts don't you think' Not for the first time I had lost the use of my tongue, how could I possibly respond to that? So I didn't.

It was about two months later; Jerry was home alone with Phil working away, when he invited me round for a Chinese take away. As always he was pretty, pink top with spray on trousers. We chatted about things then there was a pause, as he seemed to be building up for something.
'Do you think Phil would like me to have real breasts?' in the silence that followed I looked at his chest, the pink top would look good with a cleavage but Jerry is a man.
'Would you like them?'
'I think so, and Phil does like me wearing the falsies, so I wondered about getting some real ones'
I was trying hard to think fast 'it would move you from effeminate, flat chested man to definitely female you realise'
'Yes I know that, and I would need to put across as female all the time' this made me smile, when had Jerry ever come across as manly?
'And how would it go down at work?'
'No problem, got a new job starting next month, working for a firm that cleans peoples houses'
I thought again and sipped my wine 'So when are you going to tell Phil? And how are you going to get the extras?'
'Phil doesn't know, and I was hoping you would run me to the clinic tomorrow, and pick me up in a couple of days' he smiled and gave me a puppy dog look. How could I refuse him, so I stopped overnight, and rang into work saying I would be late, then ran him to the clinic and left only when I felt happy he was settled. I wanted to call Phil but was made to promise it was to be Jerry's surprise.

I picked him up a few days later with a bandaged chest and a handbag full of painkillers, I made him stop at mine till Phil was back, then he would just rest. His plan was to have the bandages off and a bra on when Phil returned. The bandages come off the Friday before Phil was due home on the Saturday. He was still sore but in his soft supporting cups, the chest looked perfect. I only wished I could have been there when they meet. But I did get a call from Phil thanking me for looking after her partner, and telling me how good he looked.

I found some weak excuse to call round, though I really did not need one, but I wanted to see the unwrapped Jerry. So with time to get ready for my visit he went all out to impress, or that is how it seemed to me, forget the silk trousers and 3" sandals, it was the bustier below the bare shoulders that took me all my time to stop staring at, there was even a fair bit of bust pushing out the top of the purple satin leaving nothing to the imagination top.
'I guess you like the finished article?' they both asked,
I tore my eyes away and tried humour 'you seem to have put on a little weight' was all my mouth could come up with, while my head was saying gorgeous.

Jerry was soon at work, and enjoying his Mrs Mop job, but still found work clothes that flattered his figure, not bad when you wear a tabard with the company logo on it. Phil was moving up the cooperate ladder, but promised never to be away so long that Jerry had time to do anything quite so dramatic without her knowledge, the chest was nice, but did not want any more changes.

I had only thought that they might get on well when I first set up the meeting, that they would end up living together as husband and wife virtually was beyond my imagination. But now when I saw them together they seemed so comfortable with each other, and with themselves.