A Brief History of Tina

"Well, Jack my darling. I wanted to see the full effect. Please, be honest, tell me."

I stood up and crossed the room to open the curtains, then turned to face him so that he got a good look.

"Tina, I can only confirm what I saw last night. The view from here is stunning. Really, I mean it, I see a woman, no more, no less. Definitely Tina, and no sign of Timothy whatsoever."

He certainly knew how to flatter a 'girl'. I crossed towards him, perhaps flaunting myself a little, sat on the bed beside him, and leaned over and kissed him briefly on the lips again.

"Thank you, Jack, that's what I really needed to know."

And as I moved my hand a little I encountered his leg through the bedclothes - and something else. I smiled. Before I had time to comment he spoke.

"Tina, don't so that. Please. Not now. This may be the place but it is not the time. I need to get up and dressed, we have things to do today."

I was puzzled, and perhaps it showed.

"Please, take your gorgeous legs downstairs, I need to shower and dress, I'll be down in 15 minutes."

Which he was. I had prepared, showing my feminine skills to the utmost, breakfast on the patio - juice, coffee and toast, and we sat in the morning sunshine, neither of us too sure about the consequences of the previous night's activities. In fact Uncle Jack kept staring at by boobs and my legs, and occasionally muttering 'fantastic' or 'gorgeous' or something like that. It was at the same time flattering and very off-putting, and made serious conversation impossible. Eventually we cleared up and I got round to thinking, now that I was dressed, just how I was going to spend the day. The gym visit was obviously out of the question. Uncle, though, had decided for me.

"Right, Tina, let's go, we have some serious shopping to do"

That floored me. Shopping? Well, of course it had to be done, I had often done the weekly shop on my way back from the gym. Whizzing round with a trolley, and then Uncle picked me up with the load afterwards. But today?

"Yes. Look, Tina, I keep telling you that you look good. You look the part. Apart from staring at your legs nobody will notice that you are not what you seem. Believe me, I wouldn't suggest it otherwise. I can't afford to be seen out with a man who is dressed like a woman, can I? Not with my position in this town. So come on, find a jacket, I'll get the car out."

I dashed upstairs and found a cream-coloured blazer style jacket, hoping it was not 'special' to Jack as far as Aunt Jean was concerned. Then, before going, I had to visit the bathroom, not as easy as it sounds when wearing a tight basque. I resolved to find, if I was in any way going to continue with this, a different style of under-garment to help control my figure while still allowing access when necessary.

Jack was sitting in the car when I got outside, I loved the thrill of sliding my bum onto his leather car seats and showing him my legs. He got the point, came up with an appreciative grunt as I struggled to fit the seat belt strap over my boobs.

"You never had that problem before, did you?" he joked.

I was worried at first about going round the supermarket with him. Though I wasn't well known in the area I had been to the local store several times. Someone there just might recognise me, or at least recognise Uncle Jack and put two and two together. But at the end of the street he turned left instead of right.

"I thought we should perhaps go somewhere different, how about that shopping complex just up the motorway?" he asked, obviously the same thought had occurred to him. "We'll get the ordinary shopping first and dump it in the car, then maybe have lunch and have a look in some of the other stores."

"OK, Jack, if all goes well that is"

"It will"

And it did.

I felt strange at first and very nervous indeed, I kept thinking someone in the store would 'spot' something was wrong and make a scene. But no-one did! And after only a few minutes I felt wonderful, strolling round the supermarket with my 'boyfriend', just doing shopping like any other couple. At the checkout I was a little hesitant, Jack did all the loading while I waited with my purse in hand. We really didn't have anything special, just ordinary things, except I had insisted to Jack that he let me buy myself some new stockings. I wanted several pairs but he insisted on only one pair, saying that I would 'get another chance later'.

After loading the stuff into the car Jack drove us back home again and I did my 'wifely' job of putting things where they belonged in the kitchen. Then he arrived at the door again carrying my jacket, insisting that we were going out again. That first 'proper' outing, when I associated with several other people, one of the shelf-stackers in the supermarket, the boy on the checkout, the guy collecting the trolleys in the car park, had done me the world of good in confidence terms. Nobody had given any indication at all that they didn't see me as I wanted to be seen, as a woman.

As Jack held the car door open for me to get out a few minutes later, I couldn't help it - I just smiled at him and kissed him yet again, there, in broad daylight, in public, in the café car park, I really was having a wonderful day. I took his hand as we walked into the café. We only had a slight snack but it was still fun, being treated as a woman, and on one occasion being addressed as 'Miss'.

And after all that, just when I was thinking we had done it all, Jack surprised me again. Instead of turning left out of the car park to head back home he turned right. I looked across at him, puzzled.

"More surprises in store, my darling" he said - the first time he had addressed me in that way.

And to back up the greeting, after changing gear, he put his hand on my knee and slid it up my thigh, under my skirt. I slapped his hand playfully and scowled at him.

"Not now my lovely."

A few minutes later we were pulling into yet another car park, in the shopping arcade at the other side of town, not one I had visited often. Again he took my hand as we strolled towards the shops. And he dragged me, well, escorted me really, straight into 'M'elle' - a rather swish ladies clothes shop! Before I could say anything he had summoned one of the assistants.

"Good afternoon sir, miss, can I help you?"

I realised straight away that she had checked straight away - noticed that I had no ring. I looked at Jack, hoping he wasn't going to expect me to reply but it became clear he had everything in hand.

"Yes, I rang on Thursday afternoon, to discuss a dress for my friend here. I got a message yesterday that you had some success....."

Thursday afternoon? That was before our session last night, what had Jack been thinking of? But now was not the time to ask him.

"If you will come with me miss, I can show you, we have two possibilities, size 12 isn't it?"

"Er - yes" I muttered, then hung back to whisper to Jack.

"What is going on here? What is this about two dresses?"

Jack spoke more loudly, so that the saleswoman could hear.

"It's a surprise my darling, we're having dinner tonight to celebrate. I thought a new dress would be in order."

He had me flummoxed. And trapped, I had no alternative but to go along. When we reached the changing area Jack sat down on a chair and picked up a magazine. I obviously did have to go ahead, on my own. The woman held open a curtain for me, I went in front of her into the changing area. To be greeted by another woman coming out of a small curtained area and posing in front of a full-length mirror, wearing only a bra on her top half! As I followed the assistant the posing woman turned towards me.

"Tell me dear, the assistant says this isn't too tight for me, but I think she's just trying to make a sale. Is it? What do you think?"

What could I do? This woman was standing there in front of me, insisting I look at her boobs and her cleavage. I swallowed, tried to speak calmly.

"It looks fine to me".

Which it did, she had a very impressive pair of tits and they were only inches from my face. I swallowed again, then gasped as she quickly and expertly reached behind her back to unhook the bra. It fell forward and her big boobs ballooned out - I was left facing two gorgeous breasts, big nipples standing out, I just had to look away and brush past her as she breathed in.

"OK, thanks" she called back to me as I walked into the cubicle next to hers. I heard her say "I'll take it, then", then managed to get my attention back to my own concerns.

When the assistant showed me the two dresses on hangers, my mind was made up instantly. The black one, it was gorgeous, a shiny black material, with small imitation gems stuck or sewn all over it, giving it a 'night-with-stars' appearance. I had to try it on but fortunately the assistant had to leave me to do so myself, she was called away. I stripped to my undies, managed to get it on with a little difficulty, it really was very tight, and satisfied myself with a look in the mirror that it was OK. Within only a few minutes I was back in the store holding it and smiling at Uncle Jack.

He paid for it, and of course I had to have a new co-ordinating handbag, and a pair of large pendant diamante earrings, and a black velvet choker with a single large central 'stone', and a pair of sheer black seamed stockings, I could have gone on but I didn't want to make too much of a hole in Uncle's card account. As we drove back home I kept thinking to myself... 'I've got the shoes, now, what sort of make-up shall I wear, and what about my nails, and shall I try to style my hair... '

All girly thoughts, I realised, I was really getting into this big-time......

We spent the rest of the afternoon just hanging round at home, Uncle Jack making appreciative comments about my figure and so on, then in the early evening he announced that he wanted me to 'dress' for dinner. I took that to mean in the new dress so I kissed him lightly on the cheek and went upstairs.

In my bedroom I stripped, showered carefully so I didn't disturb my breast-forms and their 'make-up', shaved twice and towelled myself dry. I looked across at the dress, hanging there invitingly. I was surprised - it took me much less time this time to completely redo my 'look'. I did my basque as tightly as I could and slid my new sheer seamed stockings up my legs, enjoying the sensation as I stood up and felt the tension spread round my legs. I just about managed to squeeze into the dress. Then I sat down to redo my nails, this time choosing the extremely long pair I had bought earlier, and enjoying stoking the vibrant red nail varnish carefully onto them.

And then the eyes, I do so love doing my eye make-up. I used a mid-blue over the lids, shading to a mid-purple at the top, then to pink below my eyebrows. Then a thin, not too dark eyebrow pencil to give just a little accentuation to them. The eyelashes were new to me but I relished the thought. A thin smear of the adhesive along the edge, they were more awkward to fit than I had thought but I did it, got them firmly in just the right place. After waiting a few seconds for the adhesive to dry I stroked over them, and over my own upper lashes, thick mascara, good quality stuff, it produced long black lashes, gorgeously separated and curled. Careful application to my lower lashes too, the effect thrilled me. A deep blue eyeliner followed to complete the effect.

And finally after edging my mouth with a very thin line of deep purple lip-liner, my lipstick, the same bright red as my finger and toenails, thickly applied, this was supposedly 'kissproof'! I smeared a thin coat of gloss over my lower lip and just a little to my upper, then looked across at the clock. It had seemed like about 3 hours but had taken less than one to complete my dressing. I put on the glamorous diamante earrings and clipped the choker behind my neck, again luxuriating in the feel of my long blonde hair tumbling to my shoulders as I shook my wig to 'settle' it.

Finally a diamante bracelet which had been Aunt Jean's and a silver-coloured watch, and in all seven large and rather gaudy rings. I stood up and stepped into those shoes, my 6" heel black patent stilettos, and grabbed my bag. I turned and looked in the long mirror. The skirt of the dress was so tight and so short I could almost see the tops of my stockings. And the neckline was so plunging I was revealing a very convincing pair of bulging boobs.

The effect was well worth the effort, or so I thought, I hoped Uncle Jack would like my 'look' too. I stepped carefully down the stairs in my ultra-high heels, and then strode confidently into the lounge. Where Uncle Jack was not alone, he was talking to another man!

Jack turned to face me and, while the other guy was staring at me, stepped across the room, took my hand and kissed me on the cheek. I was taken aback by both events.

"Doesn't she look gorgeous, Sam" he said to the other man.

"Fantastic" he said - it was the only word I heard him say.

He picked up a box from the table beside him and left. I looked past him - the dining table was laid with silver cutlery, as I looked Jack lit one candle over the table, then turned the light down. It was just beginning to get dark, and with the gentle music I had just noticed coming from the stereo, it was a very romantic scene indeed. Jack reached out a hand, I took it gently.

"Tina, I just knew you would look sensational in that dress, and Sam thought so too, I could tell. You did such a good job with dinner the other night that I thought I would reciprocate."

Then I realised, as I heard a van start up outside. Sam was the caterer, Uncle had bought in a gorgeous meal for the two of us. He looked across at me again.

"Don't you dare kiss me again, Tina, I would not be at all responsible for anything which then happened. Let's eat'.

I realised then - I was famished. I hadn't eaten for hours. Over the meal, not enormous but very good quality, Uncle again kept paying me compliments, then at the end as he filled my wine glass again, came the big question.

"Well, Tina. You have certainly proved you can be totally a woman. So what happens to Timothy now?"

I didn't know, I seriously didn't know. I had SO MUCH fun dressing and being seen out as a woman, it seemed a very backward step to change back, to go back to trousers and shirt, flat shoes, just being an ordinary guy. While he was waiting for me to say something Uncle came round behind me and helped me from the chair, in an extremely gentlemanly fashion. We strolled hand-in-hand back into the lounge where he opened the champagne. Again we linked arms as we sipped from the delicate glasses.

I looked him straight in the eyes, trying to keep my expression neutral. I had been thinking about his question earlier, I knew it would come up sometime during the evening.

"Uncle..." I started to say, but couldn't put my thoughts into words.

I took his hand and sat down on the sofa, pulled him down next to me. I took his left hand and placed it on my knee and looked t him again. He slid the hand up inside my dress. I felt it move over my stocking tops, slide across my bare leg and touch my silk panties. Without speaking his other hand cupped my bulging right breast. I leaned over and kissed him, hard and passionately. We separated.

"Uncle, you remember you said 'go for it'?"

"Yes, Tina, and I meant every word of it"

"Uncle. Will you seduce me?"

"Tina, my darling, if you hadn't asked, well, I am as hot as hell right now, I reckon I might have raped you before the night is over!"

As he smiled I leaned towards him to offer my most passionate kiss yet. Then he led me up to his own bedroom. As we entered I turned my back to him, inviting him to unzip my dress. This he did, snaking an arm round my waist and burying his lips in my neck as he fondled my boobs from behind. I allowed the dress to slip down, standing there, in front of my Uncle Jack, feeling like a wanton tart, my boobs thrusting upwards and outwards from my tight black basque, sheer black seamed nylons and massive heeled stilettos, my jewellery flashing in the light.

I felt fantastic, I felt promiscuous, I felt lustful.

"Now stand still, Jack my darling, I want to undress you"

And I did, undoing his tie, opening his shirt and sliding my nails through his slightly hairy chest, then unbuckling his trousers and helping him remove them, and his pants and shoes and socks. He stood up, naked. I saw for the first time in that situation a nude man, and wondered if I was in any way seeing him as a woman would. He struck me as rather 'tall, dark and handsome' - I thought for a moment. 'I want to have sex with this man'.

His erect cock was standing proud and stiff, I teased it with my fingers, Jack started moaning a little, I had to kiss him again to quieten him as we tumbled onto the bed. Then he slowly begin to rub my left thigh, stroke my garter, feel the roundness of my arse. He began to kiss my legs, playfully running his finger and then his tongue along my panty line. I reached down and felt his throbbing cock.

I kissed it, then moved lower to his balls, as he arched his back to give my mouth access. I spent long minutes licking, sucking and kissing them, enjoying their swelling and the hairy feeling in my mouth. My tongue darted down and briefly sucked at his hole before returning to lick his long shaft. I sucked round the base of the shaft, making it glisten in the light. I moved on to the bulging head of his cock, flicking the tip with my tongue, playing with it. Quickly, I covered his whole shaft with my eager mouth.

Forcing the whole cock into my throat, I can still feel the firm head as it nearly gagged me as it slid down my open mouth. Slowly then with increasing speed I began to thrust my mouth up and down the shaft, sucking hard as I moved rhythmically. Jack was moaning loudly now, trying to hold back, I could feel his muscles tighten as the first pre- cum trickled out of the tip of his cock. He held my head in his hands, thrusting when I did, working with me, until with a final devastating eruption he climaxed, filling my mouth and throat with his hot cum.

He pulled out just before I began to choke, his thick cum was warm, and sticky and gorgeous. He eagerly kissed me, and our mouths and tongues mingled with his semen. I gulped and swallowed, feeling the heat as the fluid pulsed down my awaiting throat, sensing the warmth as it moved into my stomach. This was sensational!

Together, we rolled back and forth across the bed, the memory of Jack's climax heightening the excitement of the moment. I relaxed briefly, then I could feel his hardness pushing at me again. He slowly moved on top of me, pushing down with his hips against my groin. My own cock was rock hard, straining against the lace of my panties.

Jack moved his hand down along my stomach and began to gently stroke my panties, pushing back on my shaft, teasing the head though the fabric as it rubbed across the very sensitive tip. I felt every delightful movement across the skin. He pulled my panties down a little further, his fingers probing into the hot chasm of my arse, digging at the hole of my anus. Then he pushed a finger into my arse.

I gasped as he rolled me over, his stiff wet rod square in my face. It was really erect again, I stroked his cock gently.

"Jack, you really are a very good lover you know."

"And so are you, Tina, I've never known a woman like you."

I felt great!! I took his glistening cock in my mouth again, and as I did so, it began to regain strength even more, growing larger with each squeeze of my lips, I just had to let it go. We shifted across the bed, our lips meeting passionately again.

As we parted Jack spoke.

"Timothy, this has gone way too far, this is serious, I am in absolute ecstasy right now, I am desperate to shoot my sperm up you. You never did really answer my question, where is all this leading?"