tagTranssexuals & CrossdressersA Brief History of Tina

A Brief History of Tina



A series of stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me!


1 - Monday

It really has been one hell of a week and more to come maybe, though I really am not sure how this is all going to work out. An awful lot has happened since last Monday, I am just beginning to make sense of it. Or at least, some sense.

On Monday I decided to 'shake myself out of it'. Out of the depression of the past six weeks at least. I have been living here, in my Uncle Jack's house, since that awful day six weeks ago. Since the car crash.

Both my parents were killed. OK, at my age, I should have been able to cope with that, but on top of all my other problems it was a massive shock. Just before that my Dad's business folded, the shop we were running together had to close. Blasted hypermarkets, no good at all for the small retailer, the business I had helped start and get going fifteen years ago, it just couldn't compete. Then just after Christmas it really went wrong, unsold stock, bills, Dad just had to give it all up to pay the creditors.

Which left me jobless. Then to top it all two days later that big motorway pile-up, my parents' car was right in the middle of it. At least that put paid to any stories about suicide, the television pictures proved that. But the insurance money, what little there was, all got taken to help sort out the debts. The house too, the extra borrowing to try to keep going had eaten up that too.

Which left me on my own, Not entirely penniless, I know now why Dad insisted I keep an account in my own name, he wouldn't let me put everything of my own back into the store. Thankfully Uncle Jack, who had married Mum's younger sister, he took pity on me at the funeral, offered me a place to stay, he is on his own right now. He has had his own share of tragedy. His wife, my Aunt Jean, herself died about four years ago, a terrible wasting illness which left her fading and in some pain for about three months at the end. But at least he still had Emma, lovely Emma, she was away at college. He was on his own in this big house and welcomed some male company.


Well, yes. And we did get on together, he was very understanding, didn't push me, said I could take all the time I needed to think about a job, a place of my own. For five weeks we got on very well indeed, went to a couple of football matches, in the pub a few times, a couple of rounds of golf, helped each other with cooking and housework and so on. Not that he was at home much in the day, his own business has really taken off, he spends loads of time at the office, with clients and so on. So in the day I have been left to my own devices.

So to last Monday. It had really been coming for a while, I just KNEW it had to happen.

Twice in the previous week I had, for the first time in several years, indulged in my own rather peculiar hobby. Dressing up, that is. I just love it, wearing sexy underwear, a tight dress or skirt, high heels and so on. I know it's a bit odd but apparently quite a lot of guys get a kick out of it, dressing in women's clothes. I had investigated my cousin's wardrobe and found several items which would fit me. And more surprising, a lot of Aunt Jean's stuff in a wardrobe in my Uncle's room. I knew, I had heard several times from my own family, that Jack had taken her death very badly indeed, they had been extremely happily married for nearly twenty years. But I hadn't realised he was still so affected, even after this time he had still not sorted or got rid of many of her clothes.

She had been a very attractive woman, as had her sister, my mother. Whether subconsciously I wanted to bring her back, or my Aunt Jean, I don't know. But having not 'dressed' for maybe ten years myself, the urge returned when I saw her outfits, her shoes, even a wig. With those and some of Emma's stuff I thought I could do a good job on myself.

I had twice the previous week tried on some things, found some sling-back shoes I could adjust to nearly fit. That Monday was to be my first full try-out. Uncle Jack was going in late because he was having dinner later with a client, that gave me over nine hours on my own. And some of it in semi-darkness, I could maybe even go for a short walk in the garden and enjoy the breeze on my nylon-clad legs.

When Uncle Jack set off that day I moved into action, catching a bus into town and doing a little 'femme' shopping, I bought a pair of tights for myself, some panties, a few makeup items and pieces of jewellery. I got back to the house late afternoon and took a long, hot, sweet-smelling bath. After a light snack I spread my choice of clothing out over the bed in Emma's room. I felt the need for a slightly feminine environment to take on this task. It really didn't take me long, memories of my dressing up years earlier came flooding back, the thrill of sliding my legs into tights was still there. I had bought a pair of American tights, pantyhose they were called, not too sheer but nice enough to feel really good.

The make-up skills too, came back to me. I had always prided myself on my accomplishments there, on taking care to overdo it just a little to give a really feminine appearance to my masculine face.

And within an hour I was there! Done! Finished! I stood looking into the long mirror in Emma's room, delighted with what I saw. A woman. Definitely, none of my old skills had gone. A smart and, I like to think, rather attractive woman, tight white sweater - Emma's - over black bra - Aunt Jean's - with a short-ish deep blue skirt, black tights and high-ish heels. I managed the shoes quite well even though they were a little small for me.

The wig had puzzled me at first but then I realised. Aunt Jean, by all accounts, had not been a vain woman (unlike me, I thought!) but she did like to look nice. And when she began to get ill her hair was badly affected. She must have bought the wig then, to delay the onset of the effect of the illness on her appearance. That partly explained it. The wig was basically her own colour and style, a deep red shade, basically the family colour. My own hair was the same, my Mother's had been similar, and Emma's too, though hers had become rather lighter after two months holiday in Australia last year.

What it did not explain was the other wig, longer, fuller, and a deep blonde shade. Both wigs were a far better quality than the one I had used some years earlier. I stuck to the red one, thinking it would go better with my basic skin tones.

I spent an hour wandering round downstairs, posing, sitting and crossing my legs, enjoying again the feel of nice hosiery on my legs and thighs, then went for a short walk down the garden in the evening sun. I realised the time was beginning to get on and headed back to the house, watching my reflection in the big picture window at the back.

I looked towards the back door.

"Timothy! TIMOTHY!"

Uncle Jack was standing there, silhouetted against the light! My heart missed several beats. Then before he had time to say anything else, I pushed past him, across the lounge and up the stairs. My mind was in a turmoil. Blast! I had NOT got the time wrong, he was not due back for several hours yet. But too late for recriminations, the damage was done.

"Timothy! Wait!" Uncle called after me.

I heard his footsteps, heavy on the stairs behind me. I dashed into the closest room and, since there was no lock on the door, quickly grabbed a chair and jammed it in place under the knob. Immediately I saw the knob turn and the door move, but it would not open. I sat on the bed and quickly tore off my wig and began to unfasten my shoes.

I realised I couldn't change, not fully anyway, most of my clothes were in my own room, I had dashed into Emma's bedroom in my hurry. I paused and breathed deeply. I heard Uncle Jack's voice outside the door.

"Timothy, please, wait. I'm not mad at you but we need to talk. Just stop and think for a minute."

That I had done.

"Are you listening, Timothy? I have something important to say. Please. I am going down to the kitchen, I need a drink and I think you maybe do too. Please, don't rush into changing or anything. Come down as you are. OK?"

"OK" I called out.

I heard Uncle shuffle and go down the stairs. I moved the chair, opened the door and, in stocking feet and without my wig, I followed.

In the kitchen, Uncle Jack was just getting two cans from the fridge. He opened both and pushed one across the table towards me, taking a long drink from the other. He sat on opposite sides of the small table there, silent for half a minute, drinking, thinking.

"Timothy, I am glad you came down. And I am glad this " - he looked me over, acknowledging my incongruous appearance - "is out in the open."

I shuffled slightly in my seat, nervously. I was a guest in this house and I had abused the hospitality offered to me. I wondered how Uncle Jack was taking this so calmly.

"Right, let me say what I need to say".

Here it comes, I thought, shuffling even more, and for once not really enjoying the thrill as my skirt rode up to expose my thighs.

"I can't pretend not to be concerned about this. But you may be wondering just why I am taking this so calmly."

Was Uncle Jack a mind-reader?

"But when you dashed past me to go upstairs, and I properly realised what was going on, I was annoyed - for about 15 seconds. And then I remembered something your Aunt Jean and I discussed during her last few weeks. Basically it gave me a whole new outlook on life, in one short sentence, it dictated how we spent our remaining weeks together."

I waited, wondering what Uncle Jack was going to say.

"In simple terms, life is too short, if there is something you really want to do, go for it!"

We spent nearly half an hour talking about the situation, why I did what I did, what I felt like, was I gay, did I ever go out dressed and so on. At the end of it I was much more relaxed, it had been really weird at first discussing such things with another person, specially Uncle Jack. But I did feel much more relaxed. I had assured him that in no way would I embarrass him by going out dressed, in fact I never had, until that day absolutely no-one had ever seen me 'dressed'.

"OK then, Timothy. It's beginning to get late and I have to be up in the morning. But first - like I said, if you want to do something you should really go for it. So. Before we turn in, how about letting me have a proper look at my 'niece'? Go on back up while I clear things down here, put on your wig and re-fix your makeup, let me see just what - or rather who - we have been talking about."

I padded back upstairs and sat to re-do my makeup - I looked AWFUL. Whatever must Uncle Jack have thought of me? My mascara was smeared and without the wig I simply just looked like a man dressed rather stupidly. Which was not the impression I wanted to give. I took my time, removing and re-doing makeup took longer than I thought. I'd never had to do that before.

Finally I was ready. I stood and slid on the red wig, it really was a much better quality than I was used to, and slid my feet into the shoes.

"Timothy, are you OK? Ready?" I heard Uncle call from the foot of the stairs.

"Coming Uncle" I replied, my ears jarring a little at the un-feminine tone as I shouted. I must try, I thought, to keep my voice gentle, I imagined I could imitate a more feminine tone.

I headed down the stairs and into the lounge where my Uncle, sat with his newspaper, looked up. And, I was absolutely DELIGHTED to see, raised his eyebrows and grinned as he saw me, fully dressed, really for the first time.

"Well, Timothy. I am amazed. No, really, amazed. I only got a glimpse before but you really have done an exceptionally good job. If I didn't know the truth I think I really would take you for a woman. Please, just walk around a little, let me see."

And I did just that, strolled round and posed just like I had done before, but this time for an audience.

"OK, young lady, I promise you, you really do look the part. I'm glad you did this, Timothy, it does at least show me you are in some way serious about this, that means I have to be serious about it too."

We sat together and talked about the whole thing for several minutes more, the Uncle Jack rose and held his hand out towards me. I took it, and gave him a little squeeze.

"Uncle, thank you. Thank you so much for being so supportive, so understanding. You don't know what this means to me."

"Timothy. Just one thing. Please. That wig, you will realise, it is - or rather was - Jean's. She got it when she became ill. Well, you look very much like her when you are wearing it. There is another wig upstairs somewhere, I think I might prefer it if you tried that one. You do have in some way the 'Wilson' face, you have the look of Jean, your cousin Emma does too. When I saw you, just for a split second ' - I thought - "

"Uncle Timothy, I am sorry, I never would have - you know - if I had really thought -"

"That's OK, Timothy, you weren't expecting to be interrupted, were you?" he continued.

That night, after six weeks of unsettled nights, I slept well.

2 - Tuesday

The next morning over our usual light breakfast, Uncle Jack didn't refer to the previous evening's activities until the end, as we were clearing away the dishes.

"Timothy, I have to go now. Back at the usual time, I hope, just so you know."

He smiled, an acknowledgement that many things still stayed the same despite my revelations. I thought of dressing again later that day, but didn't. As a 'thank you' I spent the day gardening, mowing the lawn, something Uncle Jack didn't like doing. He had put it off the previous weekend, so I did it for him. And did a good job too, though I say it myself. Uncle Jack did come home at the usual time, I had a decent meal prepared for the two of us. We watched a little TV - television!! - and then Jack wanted to show me something upstairs. In his bedroom he opened the wardrobe where I had found Jane's skirt the previous day.

"That top you were wearing last night, Timothy, I think it was Emma's. I know you couldn't really have asked me but - I think it would be best not to wear her things. But all this was your Aunt Jane's, and I KNOW I should have sorted it before. It has been four years now."

I had a proper look at the contents of the rack in there, I could see more than I recalled.

"But now I can put it to good use. How about you sort through it all tomorrow? Take any things you want for yourself and bag the rest, we'll take it to the charity shop in town. OK?"

I was rather amazed. Uncle Jack was actually giving me clothes to dress in, as well as permission to do so. Mt reply was a bit flustered.

"Uncle Jack, I couldn't, these were Aunt Jean's clothes, I -"

"Nonsense Timothy, you'll be doing me a favour, I've just put off sorting these clothes too long. Please?"

I just had to say yes.

"But I'd like to do something for the clothes, how about I give an extra donation to the charity shop, to sort-of pay for them. In a good cause?"

"Great idea, Timothy."

3 - Wednesday

So I did just that, I spent the next morning going through the wardrobe in the big bedroom, sorting through the clothes in there. Many were - and were always going to be - too small for me. I ended up putting these and, I very much regretted, most of the shoes, in three large bags to go to the charity shop. It was a surprisingly exciting time, but sad too, remembering that all these had been worn by my late aunt. By mid-afternoon I was nearly done, the final item I discovered was a suit. In one sense an ordinary suit, jacket and skirt, but I was enthralled by it. It is a deep grey with a thin maroon stripe, very classy, an 'executive' suit. Expensive, obviously, and either hardly worn or very well looked after. I looked at the clock - two hours, that's how much time I would have if ......

I headed for the bathroom, stripped and showered, then began my makeover once more but this time I was not out to impress just myself. Within ninety minutes I was down in the kitchen, assembling dinner, well, not a full meal today, more of a major snack, for the two of us. The suit fits me, I am delighted to say, like a glove, mid-length jacket over a classic white ruffled blouse, tight-ish skirt, straight, hemline about eight inches above my knees. I had done my nails too, in a deep-ish pink gloss which matched my lipstick, and I was very surprised the wig colour, the shiny ash-blonde, suited my own colouring so well. The wig was also a more glamorous style than the straight-cut red one. This one is longer and fuller, more curly, definitely more 'glam'.

I was sitting at the dining table when Uncle Jack came in, my legs crossed and showing quite a bit of thigh. As he entered I sipped at the glass of white wine I had just poured, then I smiled and offered a glass to him.

"I thought this would go rather well with the meal" I suggested gently, holding out the glass to him, trying to keep my voice quiet and, I hoped, convincing.

"Well, what do you think?" I asked, somewhat nervously.

It was obvious I wasn't asking him about the wine. He sipped the glass himself, looking me over, then smiled.

"Timothy, I am VERY impressed, I thought you looked good on Monday night, right now I am absolutely delighted. I see an attractive woman. Very smart, well groomed, one who takes care of herself, who likes to look good and works at it. Very good indeed."

I glowed with satisfaction. 'Herself' He'd said 'herself'.

"Thank you, Uncle Jack, you don't know how much that means to me."

And I spent the whole of that evening, dressed, in company, happy. We had our meal, I served it, cleared away and then did coffee. We sat together afterwards discussing things, changes, then Uncle Jack surprised me.

"Timothy you really do make an attractive woman. Look, my car is still out, let's go out."

Out? Out?!! I was aghast at the thought, Jack could see I was beginning to panic.

"Hang on, Timothy, nothing major. There's a little woodland about half a mile from here, Emma and I often go there to relax in the evening, a short stroll along the path there, that's all I am suggesting. Nobody else around usually. How about it?"

So we did. Uncle Jack drove us there and we strolled side by side along the path, about 200 yards, then back towards the car. He could see I was thrilled by this until, just as we approached the car, another pulled up beside his and another couple got out. An older man, maybe nearly sixty, and someone I took to be his wife were headed towards us, hand-in-hand. Jack grabbed my hand, I was shaking.

"Timothy, calm down, just keep on walking, they won't give you a second glance I promise."

And they walked right past us, Jack acknowledged the man's greeting with a 'Good Evening' in reply, and we strolled on. I was relieved to sit in the car again.

"Sorry, Timothy, he DID give you a second glance."

Obviously I must have looked worried.

"He was checking out your legs!"

4 - Thursday

The next morning we were both up early to breakfast together. I was 'Timothy' again. Uncle said he was due back a little late that day, he had a business lunch and wouldn't need a full meal. Again he was helping me, letting me know I could greet him dressed if I wanted to. I really did want to but that day it would not be possible. I had a 'date' myself, or rather an appointment, at the employment bureau in the afternoon.

I was after a job, I couldn't just hang round living off Uncle Jack full-time. But just after lunch, as I was about to set off to catch the bus into town, the phone rang. They had staffing problems at the bureau, could I re-arrange for next week. Sure I could.

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byBethanyJ© 7 comments/ 83491 views/ 50 favorites

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