That Red Dress Started It...! Ch. 04

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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!
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Part 4

I almost stopped breathing. The shock hit me. There, on screen. walking towards what was obviously Helena's front door - was a woman wearing a red dress, a blonde woman in black stockings and high heels. I gulped. Shit!

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I started to speak but Helena was staring at me. Hell, how was I going to get out of this one? The answer was, of course, that I wasn't. I was caught, red handed or rather red-footed. Red all over in fact, the dress, the lipstick, the nails, the heels. Well, nearly all over. Red stockings would have looked better but I hadn't got any. Still the black looked OK. Hell what was I thinking about that for?

My face must certainly have been red at the time, I was so embarrassed. I looked over at Helena who was still watching the screen. It now showed me, Ben that is, in normal clothes, going out, then the screen went snowy again.

"The camera must have started working again, we thought it was broken" said Helena looking straight at me. "Just for a moment I thought that was me, the dress, you know. Then I noticed the hair style didn't look right. And the black stockings - or were you wearing tights?"

I just sat there dumbfounded. Getting found out was one thing, but by Helena, and in her dress too. I opened my mouth and a short grunt came out. I closed it, swallowed, and started again.

"Er - Mrs Warner. I'm so sorry. I didn't mean to - well, you know. It was just a bit of fun. I've never done it before, honest, it was just that one time."

She looked at me calmly.

"Ben, I do have to admit I am very surprised. I mean - I never suspected. A cross-dresser. You! Well! And don't try to tell me that was your first time. You looked so good, so convincing really, you've done that before, haven't you? Come on, be honest."

"Well Mrs Warner. I mean - I have dressed up before, yes, what I meant was - I haven't you know, in this house I mean. It was just that - that dress, it is so gorgeous, I just couldn't resist it. But I've never done that before. And obviously - "

I was thinking what to say next, trying not to sound such a fool really when the phone rang. Helena picked it up.

"Oh hello mother.... Yes, back a few hours ago ... yes, hang on a moment."

She pressed the mute button on the handset and looked over at me.

"Ben, can we talk about this later. Please. In about a quarter of an hour. I'll come round to the flat. OK?"

I weakly nodded a 'yes' and left, stumbling somewhat on my way back to my flat. I hadn't been really able to read how my landlady was taking this, she had seemed calm so far. But I realised I had made a major error. Aside from getting caught. Not that I should have revealed all, I mean you don't do that, do you. Not to a landlady, not one like Helena anyway. I wasn't tempted to go for vodka, that was really the drink I had when I was 'being' a woman. But I did get a beer from the fridge and felt a bit better after it, well, just a little better. Then, realising that all good things come to an end, I started on my papers, piled round the computer on my desk. I began packing them into a big box. Obviously I had to go. Helena surprised me when she came into the flat - maybe she should have knocked, but I had left the door ajar I think.

"What are you doing, Ben?"

"Packing. I mean, I think that's the best thing, if I just go. I really am so sorry."

"Ben, stop apologising. I do realise you shouldn't have done what you did, not the way you did, but there is more at stake here. I mean, OK, I know you like to dress as a woman. But does it go further? I mean, do you - you know - date men, that sort of thing. I mean - are you gay?"

I had to stop for a moment. The video had obviously shown me, dressed, at the door. That must have been when I switched the camera on, when I reset the system after that guy had left. She obviously hadn't seen any of that. But it was what she said next which changed my thinking.

"Ben, there's not a problem if you are. Please believe me. Out here in the sticks we don't see much of the gay scene, in fact I think I only know one gay man, he works at one of Charlie's shops. And I don't know a single lesbian, not that I know anyway."

"Well Mrs Warner. No I am not, I've only ever been with women. I mean, I'm interested in a way but I've never tried anything. Never really wanted to."

"OK Ben. And call me Helena, 'Mrs Warner' sounds so formal. Now, what are we going to do. You certainly have no need to leave. You said interested. Well I am interested - in you, with you, Ben? I really want to see what you are like. I didn't get a good look on the video. Do me a very big favour please. In fact two favours. One, stop packing. And two, I'd like to see you dressed. Would you do that for me?"

My mind immediately said yes. But I knew I couldn't, shouldn't, keep things secret. I had to tell it all, whatever the consequences. I decided that Helena had to know everything, my earlier dressing, the few times I had been out dressed, the policewoman in that Ladies' loo - and the locksmith guy. Everything.

It took me half an hour. I wobbled between talking lucidly about getting dressed, muttering a bit when I talked about my trembles when I got close to people, and nervously going through my attempted rape step-by-step. I finished, I stopped, I just sat there. For a few moments Helena said nothing. Her face was - well, furious, no other word for it. She stood up and walked out, calling out 'back in a couple of minutes, Ben' over her shoulder.

Amazingly my thoughts were not on what I had said or on her reaction. They were on Helena's bum. I had seen it walk out of my house - and a glimpse of my own arse, in Helena's dress, caught on camera in Helena's hall shot into my mind. Her bum was definitely female and, amazingly I realised, mine was pretty good too! Helena returned after about five minutes. With surprising news.

"OK, Ben let's get you sorted out. I've just rung the security people. Told the boss there that his guy David – behaved totally inappropriately when he came. And I said he had to sack him."

Maybe I looked a little surprised. It was not what I had expected to hear.

"Look, don't worry, he deserved it. I told them I wouldn't press charges. Anyway the boss said he'd heard something about this guy from another customer. It sounds like you weren't the first. He's got what he deserves, so what about you?"

"What do you mean?"

I didn't understand what she was getting at but then I realised what she had said about getting dressed. But had she meant it. I looked straight at her and I knew this time what she was thinking. Yes she did.

"So, Ben. I have to go down to the shops. If you've nothing better to do I really would like to meet your female half when I return. About an hour and a half? OK?"

And she was gone. Two minutes later I peered out and saw her car disappear out of the drive. Then I shot into action. A quick look in my wardrobe, OK no gorgeous red dress but that's not what I was after this time. I was going to be inspected closely, or so I thought, this time, I had to do a good job, a convincing job. I was going to be inspected closely - by a woman.

The basic decisions were made, I didn't have much of a range of clothes, women's clothes that is and, though I know some things like T-shirts and jeans are basically unisex these days I just didn't fancy wearing anything like that. My own women's clothes were definitely separate from my men's. Like I said the decision was almost made for me. The only really suitable outfit I had was the one I had worn to go out shopping, that first time I had been nearly caught out.

The deep maroon business suit had been very cheap indeed, only £6 from a charity shop in Edgbaston. The heels weren't matching, I wish they had been, but I did manage to 'accessorise' and make them look not too bad. The suit had a thin black stripe running through it, and black pocket flaps. I was getting good at this by now, even allowing for the fact that I was very nervous, dressing 'for Helena'. I was ready in almost record time. About an hour and a half that is, to don the fake breasts, my black undies, the stockings and heels, I even did a pretty good job on my make-up though I say it myself.

I looked in the tall mirrored door of my wardrobe. Yes. I was ready. Ready for inspection. I had just wondered whether, since Helena hadn't returned, I should go across to the front door when I heard her knock. Gingerly I opened it.

"Do come in, please".

I kept by voice down, with the feminine lilt which had indeed been so successful with the security guy. And I am delighted to say that it seemed to work, in fact the whole thing seemed to. To the extent that, for a few seconds, Helena just stood on my doorstep, almost frozen. Then she came in and looked me over.

"Turn round Ben, let me see the full effect."

I did as she asked, managing very successfully on my heels.

"Ben. I have to say this. I'm in a way not surprised that man tried to rape you. You do look good. No, more than that, you look great. Really – very attractive. I am amazed, I mean. On the video you looked OK, in fact more than OK. But in the flesh - wow!"

I must have blushed. I didn't know how to respond really, so I decided to offer Helena some tea. She came with me into the kitchen to help prepare things. We ended up sitting on my sofa, sipping tea and having what I had always imagined to be a rather girly talk. Helena asked me loads of questions, about when I liked to dress, and how often, and what I liked to do - and again she asked me - did I think I was really gay?

That last one I hesitated about. For some reason I didn't want to answer it, I had been being a woman for so many minutes, hours that afternoon, I didn't want to admit again that I was a man. But I had to.

"I really don't know, Helena, I've not so much experience. I mean, that time with the lock guy, that was so disgusting, it really didn't count. See what I mean?"

"I do, Ben, I do. But it's something you're going to have to think about. I mean, when you go out dressed like that you're bound to attract attention, you know. You're going to get men looking at you. And maybe wanting to do more?"

'When you go out ....?' What did that mean? I looked straight at Helena. She read everything into my look, worked it all out, answered all my questions in one go.

"Yes, go out. You can't go back, Ben. This charming woman I see in front of me, 'she' has to come back, to be seen, to go out, well, just to - be. In fact - hang on here for a few minutes, Ben. I'll be back."

With which words Helena put down her cup, stood up and fairly dashed out of the door. Obviously she had just thought of something, I didn't know what. So I busied myself in clearing the tea things and generally tidying for a while. Not with any special pleasure in doing housewife things while dressed, it's just that they needed to be seen to. I had just finished when I heard her come back, I returned to my small living room.

Helena was indeed there but she had changed out of her jeans. With a speed I could only admire and envy she had transformed herself, with a careful dash of make-up, a sweater and a skirt and proper shoes instead of trainers, she was not just quite good looking anymore, she was positively attractive. She slipped on her leather blouson as she came in and then surprised me.

"Come on then. We're off out."

Out? In daylight, now? I couldn't. But I could see from the way she was standing there, with the door open behind her, I was going to. I was relieved and pleased. This was an appreciation of my efforts, a recognition that I had done a good job. Obviously Helena, wife of a prominent local businessman, would not be seen out with a man dressed in a frock, indeed with any person obviously male and dressed as a woman. So I must look all right. Internally I smiled. I picked up my handbag and slipped my door keys in, slung it over my shoulder and followed her. Out.

Out into the big wide world. My previous escapades paled into insignificance compared to this. We went in Helena's car. Soon she was speeding along the ring road, then she turned back towards town a half mile or so and pulled into a car parking space in the jewellery quarter of town. I got out and looked around, never having been in this area before. Quickly Helena came round the car and took my arm and we walked along, for all the world two girl friends out to look at the shops. We had to walk about fifty yards to the arcade we could see in front of us, on the way Helena asked me what she should call me.

"I can't say 'Ben' can I? You have to have a girl's name. Any ideas?"

I didn't have to think.

"Well, for a while I've often thought about 'Bethany'. It's a little like Ben and a nice name, I think."

"Perfect" said Helena, looking over at me and smiling. "I like it."

And then I noticed where we were. Outside a clothes shop, in fact outside 'CC's', one of her husband's stores. I was a little nervous but Helena was obviously on home ground. As soon as we entered one of the shop-girls came over to greet us.

"Hello Mrs Warner, nice to see you. You look well - how was your holiday?"

They chatted for just a minute or so, then Helena turned to me.

"And this, Vera, is my friend Bethany. She's after quite a lot of stuff today, some problem with her luggage I think. Can you lend us a hand please?"

And she did. Vera came round the shop with us, offering advice on sizes and materials and so on. Within twenty minutes I had a basket full of clothes, undies, three or four skirts, several tops and sweater, tights, stockings. I was in a tranny dream, this was gorgeous. I wasn't at all sure about paying. I did have my credit card with me but - it said 'Ben Jackson' on it. Whether Helena realised this or not I didn't know.

"OK Vera, put this on my card will you? And can I do an application for Bethany while we're here? I think she may need to come back after Christmas. She's a close friend, can we do a gold card for her? I'll approve it, Charlie wouldn't mind I know."

A few minutes later I was signing the application form with my 'new' name and Vera handed over a small card in a clear plastic wallet.

"OK Bethany, still now please. This is for the real card."

I looked up, there was a young man beside Vera - with a camera! I must have looked shocked, Vera reached and took my hand and squeezed it gently.

"It's OK, Bethany, this is for the ID on the proper card. It should only take a few hours to have it done. Don't worry, this is Erik, he's very nice really, he won't bite. "

I relaxed a little as I realised what was going on. Erik asked me to stand still for a moment and took a photo. My very first, the first picture of 'Bethany' on film! I couldn't help smiling to myself, then Helena took my hand.

"Come on Bethany darling, lots to do"

If Helena had called me 'darling' in other circumstances, well ... But then I realised, I wasn't thinking of her in quite the same way as before. OK, she was a very attractive woman. But in some way she wasn't simply an object of desire. She was a friend. A girl-friend. Not a 'girlfriend' as a man would think of her but a friend who was a girl. Like me!

She led me by the hand out of the shop and towards her car.

"OK Bethany, I'm feeling just a little peckish. There's a wine bar just up the road here, let's go there for a bit of a snack. Then I want to take you somewhere else."

I was having difficulty keeping up, Helena seemed to be enjoying herself. And so was I. We put all our purchases into the boot of the car and Helena drove us, less than a quarter of a mile. She pulled into the car park - at 'Senoritas'.

"Helena, hang on, I'm not sure about this" I muttered as she pulled to a halt. I was worried - again. "I know this bar, it's a well-known pickup place. Several of my friends come here regularly, what if I meet someone I know?"

Helena looked across at me, her gaze swept from my head and down my body to my legs.

"Bethany, if anyone you know sees you here all he'll do is try to get off with you. In no way will anyone recognise 'Ben' in you. Believe me. Anyway it livens up mid-evening, right now there won't be many people here. We can just get a sandwich and a drink. I really am quite famished, you must be too, we didn't have any time for lunch. Come on girl, go for it,"

Helena really did give me confidence, so I 'went for it'. A few minutes later we were sitting at a small table near the bar as a waiter brought us a couple of sandwiches and two glasses of white wine.

"I told you we'd be OK" said Helena. "There's only about ten people in right now, the place will be heaving at nine. And - any problems, anyone you know?"

I sipped my drink, then gulped slightly.

"The waiter!" I giggled.

"What!" said Helena, almost shouting.

"He's called Harry" I said. "I knew him quite well last year. We even played football together once"

"Well Bethany, you've got away with that one haven't you. I told you so. I was watching when he came over. Apart from checking out your legs - and mine - and our left hands of course, he didn't show any signs of recognition at all did he?"

"Left hands?" I muttered. Thick, I must have been, I should have realised.

"Yes. For rings. So he knows I'm married. And more than that he knows you're available. Well, what about it? Do you fancy him?"

I looked across at Helena, somewhat aghast. Then I realised she was joking with me. But I had an appropriate response.

"Actually, no. Don't fancy him at all. And I have seen him naked in the showers, he's nothing to write home about."

We both giggled again. But I thought I should ask Helena what she was thinking - about the whole thing, me, dressing up, Bethany. And the clothes she had bought me. Why?

She stayed quiet for a moment, then put a hand over mine. I looked. It was weird, but comforting. And my train of thought went sideways yet again. What was I thinking? I was thinking 'nice nail varnish, looks nicer than mine'. Then Helena spoke.

"Well Ben. Let me speak to you as Ben for just a moment. To be honest I'm quite enjoying the dress-up part of this. Like having a doll but life size, and alive. Weird, isn't it? But really there's much more to it than that. "

We ate our late lunch and sipped our wine and talked on.

"It's like getting to know a new person. Like you, Bethany, I know you're really Ben but you're very different. Obviously to look at but also to talk to. Like a sort-of sister really, I always wished I'd had a sister. Two brothers, that's who I grew up with, both older than me. Not exactly lonely but you can't talk to a man the same way as you can to a woman. Really you can't. OK, I've got Charlie now and we are very happy together but apart from one friend, Kate, I haven't got any other really close woman friends.

And, with you Ben, there is something else as well. I must be careful, I do keep swapping genders don't I? There really is a thrill. A sort-of sexual thrill but not like sex. Just knowing that the guys in here are looking at us, imagining they'd like to screw us. And with you, it's such a vicarious thrill, knowing that all that lust is really in vain. So tell me Bethany, for you, what has been the most exciting moment of your feminine life?"

I had to think. Suddenly in the last few days, indeed the last few hours, so much had happened.

"Well Helena. I'm not really sure. The very first time I went out dressed, in my mother's business suit when she and Dad were on holiday. I walked down the street and round the corner and I felt so free. Even when a man stopped me to ask for a light, I didn't smoke at all then so I had to say no. But he had taken me for a woman, that was so much fun. And when I got let off by the policeman in that supermarket, that was some sort of fun in a way. And ... no."