That Red Dress Started It…! Ch. 05



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!


Part 5


Helena saw the look on his face too, she grabbed me and turned me towards the car. I looked at her.

“Yes” she said.

‘Fuck’ I thought.


Helena very quickly indeed bundled me and all my purchases into the car, than started up. I looked across, Andrew was still looking. The noise of the engine starting jolted him into action. His face changed from the blank stare and he began to move towards the car. But Helena, expertly as ever, swung out into the traffic – and we were off.

“Helena, he knows, doesn’t he? And I thought I had been doing so well.”

“Bethany my dear, you have done well, very well indeed. In fact I was amazed it took Andrew nearly ten minutes to spot you. And to be honest right now – I think he suspects but he’s not so sure. I mean, Kate had no idea. And neither had Vera in the other branch, nor your waiter friend nor the guy you gave the leg-show to. You have done so well today. I haven’t had such an exciting shopping trip for so long – and I haven’t actually bought myself anything!”

I thought for a minute, trying to make some sense of what Helena had said, then I realised there was something wrong.

“But – if you thought Andrew would find out about me – within a few minutes you said…?”

“Now it’s you who hasn’t realised, Bethany. Remember I told you, Charlie and I only know one gay person. Remember what Kate said about Andrew? I know he doesn’t go about in the gay scene in town but I do know he has come across one or two transvestites. I really thought he might spot you in a few seconds. But Bethany, you must be good, he didn’t. And as I said, even now I don’t think he’s certain. Now, we’re home, come on. Let’s get all your shopping in. “

Which we did, we didn’t talk any more about it, just got the bags into my flat and I started unwrapping. I paused as I got out the several bra and panties sets I had just acquired.

“Helena. Please. I really have had a fantastic time today, thank you so much. I was so worried when I saw that picture on the video but you have been so understanding. But I need to stop a bit and think. I really don’t know where I go from here. It rather seems that my ‘hobby’ has somewhat taken over.”

“It certainly has” said Helena, looking down at my legs as she drove.

“I mean that’s what it has been really, a hobby. And one which some people might look down on so I’ve kept it quiet. But now I do have to pause a little and think.”

Helena looked at me sympathetically.

“I can see what you mean, dear. This must have been a real shake-up for you. But I’m still glad we did it.”

“Oh Helena, so am I” I blurted out.

“And we will have to put things on hold for a while, Bethany – or rather Ben, now. Charlie and I have so much to see to over Christmas. Our time is so full over the next four or five days.”

She paused, rather suddenly, for a moment, then looked out of the window.

“But there is one more thing. I really think it has to be done. Charlie’s back. Ben, or rather I mean Bethany this time. Charlie and I have no secrets from each other. He has to know so – how do you want to manage this?”

I had to think myself. My relationship with Helena had taken a sudden new direction. Charlie and I. Apart from being landlord and tenant, we had been ‘mates’ up to now. Doing man things together sometimes. Despite the differences in our ages he was a good friend, something of a father figure or maybe a friendly uncle. How would that have to change?

“I suppose he does have to know?”

“Well, Bethany, if you were just about to suddenly stop your ‘hobby’ maybe it could be ignored. But I know and you know that isn’t going to happen, is it? Don’t worry, I can do any amount of persuading, Charlie will see things my way. I think he would anyway. So. Shall we go and introduce him – to Bethany?”

I had to agree, Helena was right, I just didn’t quite see how Charlie was going to react to me, young Ben, his ‘mate’, being a transvestite. I smiled weakly at Helena.

“OK, let’s go.”

We crossed the short path to Helena’s front door together, and went into the house. We could hear movement in the lounge, Charlie was speaking on the phone to someone. Helena signalled for me to go through into the kitchen and to wait there, then went seeking her husband herself. I heard muttering though I didn’t hear just what was being said. Then there was more, louder, muttering in the hall. I could hear Helena’s heels clicking on the wooden floor there.

“Come on, Charlie. I want you to meet someone.”

Helena came in, with Charlie behind her. I was standing by the kitchen table.

“Bethany. This is Charlie, my husband. Charlie, meet Bethany.”

He held out his hand and I gently shook 1080 porno it. He smiled at me. I realised, she hadn’t said anything – yet. And even Charlie, who I saw nearly every day, didn’t recognise me.

“So, let’s sit down, we have things to talk about.”

I didn’t really know what Helena was leading up to but she and I sat and I followed her lead, tried to relax, Charlie sat just facing me around the table. I crossed my legs and, five seconds later, Helena spoke up again.

“I knew it, Bethany, did you see? Charlie’s first reaction as you sat. He was inspecting your legs. I told you that you have nice legs, and that those heels and stockings do show them off nicely.”

I was beginning to get embarrassed and so was Charlie. He looked at me.

“Go on Charlie, we’re being a little unkind to you really. This is really unfair. You’ve had thirty seconds and you’ve not spotted it ….. “


“Now you have” said Helena.

Charlie stood up and looked at me.

“Ben. Streuth Ben, you look – well I was going to say you could have fooled me. In fact you did fool me. You look — amazing. Come on, what’s going on?”

Helena looked at me and stayed silent. I knew the next bit was up to me.

“Charlie, I’ve never told you this. It is a bit embarrassing and I wasn’t at all sure what you might think of me. It must be obvious now. I’m a transvestite.”

I stopped . That simple statement, combined with what Charlie could see for himself, was enough. I expected him to stay silent for a while and think but he carried on talking almost immediately.

“Christ, Ben, I’ve seen some trannies in my time, not really I mean but on the TV and on films. Some of them looked pretty good, convincing really. But you, well, if I didn’t know, I mean, you could be a woman. Wow, you look great, the make-up, the clothes, the figure, and yes you have got great legs. Come on you two, what’s been going on? Tell me about it.”

“I think I’d better” I said to Helena.

“OK, Bethany, I’ll put the kettle on, or would you like something stronger?”

“Whisky. Neat ” said Charlie.

“Well Helena, I could probably murder a G-and-T right now!” I said.

“Me too” added Helena.

She got us the drinks, I had to be careful not to take mine straight down to quell my nerves. Again I was in a new situation, again I had to explain myself. Over the next fifteen minutes with occasional additions from Helena I went through my story, from the initial dressing-up sessions at home all the way through to the question mark on Andrew’s face as we had parted that afternoon. Charlie sat there listening, frowning sometimes, smiling occasionally.

“And that’s it, Charlie. The whole story.”

Charlie was never one for silences, he came straight in.

“The bastard, that David bloke. Trying to seduce my wife. Bastard. He got what he deserved, well done Helena. Bastard.”

He did pause for a while now, then looked across at me.

“OK Bethany, stand up and give me a twirl, I want a good look at what I’m dealing with here.”

That surprised me but I did as asked, offering to get him another whisky which he agreed to. I walked up and down a little, then sat and crossed my legs again.

“Wow Ben, or indeed Bethany. Whichever. Obviously you shouldn’t have come in while we were away, that was an invasion of privacy but I think you realise that now. There could have been all sorts of problems, in fact there nearly were. But that’s water under the bridge now. So where do we go from here? Helena, you say absolutely nobody realised, and looking at this charming woman here I can believe that. Except maybe Andrew? What am I going to say to him tomorrow.”

“Don’t say anything. In fact get him to ring me, whatever he says. I’ll have a word with him. And don’t you worry Bethany. I won’t give your game away, at least not yet.”

I was a little concerned as to what Helena might say nevertheless, but suddenly our conversation had to stop. Helena had just noticed the clock above the fridge.

“Oh dear, Charlie, I’ve just realised. Weren’t you going to ring Vince – tonight you said?”

I realised that I had to make a move,

“Sorry Helena. And you too Charlie. I’ve taken up too much of your time. I really am glad that this is in some way out in the open. Though I am very surprised at the way it happened. But I need to go now, it’s nearly Christmas and you have things to do.”

“OK Bethany. But this isn’t over, let’s all take a couple of days to think it over, then we’ll see” said Helena as I stood up and reached for my handbag.

She walked with me to the front door and as she opened it, turned and smiled ever so sweetly, and gave me a light kiss on the cheek.

“Bye Bethany. It’s been fun.”

When I got in I changed immediately, and rapidly. ‘Bethany’ went away, at least she went into my wardrobe. And after cleaning the breast-forms with the solvent, and the nails too, removing my 2 k porno make-up and so on I did one thing different. I realised that I had just spent quite some time wearing my ‘femme’ clothes, not just the usual hour or two. So I washed them. Washed my undies and my stockings, and wiped my shoes over, feeling still in some way feminine as I hung them around the bathroom to dry. That night I slept surprisingly well.

Christmas actually went better than I thought it would, it had seemed to me as I got up on Christmas Eve that it may all seem an anticlimax. It was my first full Christmas away from home, from parents that is, and I had imagined myself missing the family atmosphere, the presents and so on. But things did fill in the time very enjoyably. That Christmas Eve I did first what I had decided to do the night before. I went out and got Helena and Charlie a decent present. I had already got Charlie a tie the previous week, one I knew he and Helena would approve of. But I decided to keep that in reserve for a birthday or something.

I wanted to get something totally non-tranny related. No clothes or jewellery of any sort, no make-up. OK the tie was just a tie and a nice one at that. But it was clothing. In my visits I had noticed they had two very nice decanters beside their drinks cabinet, quality stuff, I recognised the designer name. And I knew it would be expensive but – they deserved something nice.

And I knew where to buy another so I did. Same designer, different size and style, a decanter and a set of glasses which I knew would go very well in their lounge. When I handed it over Christmas morning I got the ‘you shouldn’t have’ and so on but I know it was appreciated, and they knew I really wanted to say thank you.

I met Vince that afternoon, Helena’s brother, when he and his wife came over to visit with their little Sam who was about six. And I made myself useful, looking after the little lad, playing a bit of football on the lawn, showing him one or two computer games, generally playing the extra uncle for him. We got on well. And Vince and Mary were very grateful.

“Really Ben” said Vince as they were about to drive off. “Thank you so much. We’ve had a great time, Mary and I got out on our own for about four hours. It’s usually so difficult to find time on our own in the holidays.”

And he actually tried to pay me for baby-sitting.

“No, Vince, no way” I insisted. “Charlie and I have an arrangement. I get slightly cheap rent and I help out in the house a bit. This counts in that, anyway. I enjoyed it. Have a good Christmas, this bit’s on me.”

I found a decent film on TV on Christmas night, for once. Then on Boxing day I decided to get on with my Masters’ project since I’d had several days away from it. And the trips to ‘CC’s had given me some sort of inspiration. I’d always realised that as a designer I’d never get into the very top end of the market, designing cars or aeroplanes. Even things like jewellery didn’t really spark any real interest in me. But I’d always liked the thought of ‘retail’. And at that stage I needed a theme to put to my Professor after the holiday, some peg to hand my own design thoughts on.

So I decided to have a real go at a design package for a retailer, the works, shop signs, logos, in-store features, clothing for staff maybe, an in-house magazine, that sort of thing. Making it uniform but not boring. I spent a couple of days at my PC laying some ideas down and was very pleased with what I had done. I even got Charlie to have a look at it just before the New Year, to see what he thought. I had hoped he might come up with some ideas himself for me. He didn’t though he did seem quite impressed and made a couple of useful comments.

I packaged my printouts and drove down to college to hand them in to my Professor’s secretary, knowing he wouldn’t be in until after the holiday but at least it was a load off my mind. And I did have a very fortuitous meeting that afternoon. A fellow graduate, Jenny, had dashed into college briefly for almost the same reason, to leave some stuff for the same Professor. She was stuck in Birmingham too but hoping to go home for the night the next day, New Year’s Eve. We got chatting and ended up back at her flat drinking and watching TV – and I struck lucky. I’d seen her around the place and thought she seemed nice, yet in our alcohol-amplified states that evening maybe we were both feeling a little lonely and looking for company.

I ended up staying the night and, to be honest, doing something to reassert my male ego in my own mind. I eventually left to drive home very carefully at about six in the morning feeling much recovered after several hours sleep – we had both enjoyed a very satisfying shagging session which had gone on for several hours. When I got back I slept solidly again for about four hours and woke up feeling reassured and refreshed. Then after a brief drive to do just a little shopping ready for the New Year break, there was a knock at 3 k porno my door. Helena came in.

“Hi there Ben, good Christmas? I’ve not seen you about for a couple of days.”

I think she was wondering if I had been ‘dressing’ in private maybe but from my reaction it was obvious that wasn’t the case. I told her that I had been busy with some college work and had made some worthwhile progress. I was surprised that Charlie hadn’t mentioned what I had shown him to her but I realised that if he thought it was work-related maybe he didn’t want to discuss it over the holiday period. I just didn’t mention the previous night.

“OK Ben. Now, one thing, I did talk about this with Charlie a couple of days ago. I didn’t mention anything earlier because I thought you might fret too much thinking about it. Tonight. Charlie and I are having a Party. Are you letting in the New Year with anyone this year? Going home maybe?”

I had explained the problem with Christmas where my stepfather was concerned, and said that the same thing applied this time too. I did hope to be able to go home to see my mother, and maybe him briefly too, in a couple of days time before college started. But no, I was just planning a quiet night in my myself. What I didn’t say was that I had been hoping to recover from the previous night.

“Well then. Ben. How about coming round to join in the party? It will be rather noisy, I think, and I don’t really like the thought of you sitting here all on your own at midnight if all that is going on around you.”

It was a kind thought although I maybe should have realised what was coming next before I agreed.

“Good Ben. Just one thing – you have to wear this.”

With which she stood up and opened my door and reached out, bringing in something which had obviously been hanging on the hook outside for the past few minutes. I looked. My surprise was genuine, I just hadn’t realised – Helena was holding a clothes hanger. On which was hung – that red dress!

“In case you hadn’t realised Ben, we would like ‘Bethany’ to come to the party. And before you start asking questions we have discussed this though I told Charlie not to say anything yet. It’s just a few people from work including Kate, you met her the other day, remember? In the Edgbaston branch? And, before you ask, Andrew can’t make it, he’s spending the New Year with his parents in Coventry. So. Just say yes.”

I thought about it, but not for long.


Not that I wanted to say no but Helena had obviously thought this through. But in that dress? I mean, it is a gorgeous dress. And she looked sensational in it. And I thought I looked pretty good. At least it had fooled that David person. But at a party, in company? Well?

“OK Ben, that’s settled. I’m wearing a little white dress Charlie got me for Christmas and I know you will look gorgeous. Give you a chance to try some of the lingerie we got just before Christmas. I’m off now to have my hair done. Can you change this afternoon, have you time? Can you be there by about six? “

And when she left I sat down hard, to consider what I had just agreed to. Basically a superb idea but as you might expect the self doubt started up again. But Helena trusted me, presumably Charlie thought I could get away with it. And I realised the best way to increase my self-confidence, and to enjoy the opportunity as much as I desperately wanted to, was to get on with it. Sure I could be ready by six o’clock but I would need the time.

So I got to it. I looked at the dress, then quickly got out all my ‘accessories’ on the bed, everything I was going to need to complete the look. I mentally checked through things, going through the actual dressing process. With everything ready I decided there was time for a brief, hot fragrant bath after which I did my toenails. With that dress again it was going to be scarlet – I got very excited at the thought as I carefully caressed the deep gloss varnish over the nails.

I went through the next stages — breast-forms, my new red bra and hi-cut panties and black seamed hold-up stockings – quicker than I imagined. Which really did give me time to concentrate on my make-up itself. As I finished adding the second gloss coat to my scarlet lips yet another tingle of excitement went through me. It was getting nearer – the dress!

But I still had to sort a few other things first. I chose a diamanté choker I had been ‘saving’ for a special occasion, which this certainly was, and matching rings on four of my fingers. A little over the top but heck, this was a party, a great opportunity for any girl to show off. I took great care with my wig, teasing the curls out to give me real ‘big hair’, I really did want to impress. The diamanté earrings were rather special, matching the choker and my rings and hanging down nearly 4″ from my earlobes. After I slipped my feet into the red ultra-high heels and stood back to look at my reflection. I looked good!

And then – the dress! It really did slide on beautifully, as if it had been made for me, so snug and tight, so short at the hem, so low-cut over my breasts, such bulging mounds I was getting turned on myself! I sat down for a while to calm down, moving a few things into my small scarlet clutch purse.

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