You Bet!

Part 3

By Kim Johns

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The next day, while at work, I got a phone call from Jean.

"John, I've been doing some thinking," she began, hardly waiting for me to finish my greeting.

"Always got to be a first time," I told her.

"Don't start. This is serious. Have you realised that Barry and Harry are going to want some proof that you've been to this party with me?"

"Proof? Well, you'll tell them, won't you?" It wasn't something that had occurred to me; I tended to accept what my friends told me as a matter of trust. Why wouldn't they believe what Jean or I told them?

"Of course I will, but you know what they're like. And there's six months beer involved in this!"

I paused to reflect. She was perfectly right. Money, in the practical form of liquid refreshment, was involved in this, and quite a lot if they held to their end of the bargain. Of course they'd be asking for hard evidence. How on earth could we convince them that I had been to the party dressed as a girl if they were unlikely to accept Jean's or my say-so?

"Anyway," Jean continued, "I've had an idea, if you're up for it."

"Go on."

"I thought we should meet on Friday night with you in your outfit."

"What?" I spluttered, feeling embarrassment creeping up the back of my neck like a red tide. "Meet at the pub dressed like that? I don't think so!" I looked quickly around the office to see if anyone had noticed my raised voice and was peering inquisitively at me. No. Good.

"Calm down, John. Think about it. Last night, even your mother didn't recognise you at first, so there's no chance anyone else will think you're anything but what you appear to be. And of course we want the boys to see what you're going to look like when you do go on Saturday. It might be the only way to convince them that you intend to go through with it."

I thought about her suggestion. It made sense. The only problem I could see was, would I have the brass nerve to show up in public dressed as I had been the night before? I knew I had to face the test on the Saturday, but that would be at a party in a private house. Bad, but bearable (probably). To go to a pub? That would really be an ordeal, and I wasn't too sure I was up to it. However, I knew I had to grasp the nettle sometime...

"OK," I said slowly, "How do you suggest we do it?"

"Well, if you're game, I don't think we should make it easy for the boys." She adopted a fake French accent. "Listen, for I'll say this only once ..."

Ignoring her reference to 'the boys,' I clasped the receiver closer to my ear.

Jean suggested that I phone Barry and tell him that I couldn't make it on Friday, that something urgent and unexpected to do with family had cropped up and I had to be elsewhere. Once I had done that, I should let Jean know, and she would then also phone Barry a few moments later to say that an old girlfriend of hers had unexpectedly turned up for the weekend and she was wondering if it would be OK to bring her to our Friday evening session. She would even suggest that her 'friend' might hit it off with Harry or John, hopefully then prompting Barry to reveal that John wouldn't be able to turn up that evening. Jean would be suitably surprised and arrive at the pub with her 'girlfriend' in tow. The plan was to see how long it would take the two boys to realise who I was!

I was a little sceptical, feeling that I would be outed as soon as they set eyes on me -- after all, we had known each other since primary school - but as the whole point was to show them what I would look like on the Saturday, and that I was determined to go through with the Saturday night experiment, I couldn't really fault the arrangement. My only concern was that I would walk in the pub and have a crowd of strangers laughing and pointing their fingers at me, nudging each other to have a look at the 'perv in the frock.'

Jean pooh-poohed that thought. "You might be surprised," she suggested. "I don't think anyone will give you a second glance. Well, perhaps the men will! I personally thought you looked great as a girl last night, and so did your mum. Why, she even got a bit tearful when she saw you!"

"True," I agreed, not completely convinced, but as I say I trust my friends. If Jean thought I could do it, I'd do it! "OK, we'll give it a whirl and see what happens."

"Also," Jean said as the thought occurred, "I'll tell Barry we'll meet at the pub because I'm taking you out during the day. That way you can get changed at yours and we'll go from there, rather than Barry picking me up from home. It would be a bit difficult to explain to my family why you were dressing up!"

"You're the boss," I told her. "Who ever said women were devious?"

She laughed and hung up. I listened to the dialling tone for a moment or two, my confused thoughts elsewhere, before replacing the receiver.
 

*          *          *
 
Everything appeared to be running quite smoothly for our plans, and thoughts of Friday were far from my mind as my mother and I ate our evening meal, washed up and put away the dishes that night.

We settled down to an evening of television, each of us with our own preferred alcoholic beverage, but as the hours plodded by I became very aware that my mother seemed to have something else on her mind. Far from being engrossed in the programme being transmitted she kept glancing over at me where I sat in an armchair, opening her mouth as if to speak and then hesitating and returning her eyes to the flickering screen.

After a couple of hours of this plainly apparent fidgeting on her part I finally sat forward in my chair, looking at her.

"Mum, what's on your mind? You're no more interested in this sit-com than I am, and it's as clear as clear that you want to say something! What have I done wrong now?"

The last question wasn't necessary; I merely used it as a lead-in to assist my mother. Had I been at fault over anything in any way whatsoever she would have had no hesitation in apprising me of the fact.

She looked over at me, clearly embarrassed, and again paused before speaking.

"I was thinking," she finally said, "Of last night."

Drag night, I thought, mentally raising my eyes to the ceiling. Now what?

"Oh, yeah." I commented. I wasn't going to give her any encouragement.

A pause. Then: "I...er...thought you looked pretty good in that get up."

I sighed. "By 'get up' I suppose you mean the dress and everything?"

"Yes."

"Well, thanks, I guess. Do you think I can get away with being a girl for an evening?"

She gave me a strange look, and nodded. "Absolutely. You had me fooled until Jean let the cat out of the bag by mentioning you were going to an all-girl night."

"You wondered how I might have wangled an invitation?"

"I'm not silly, John. Unless you were going as a male stripper -- which I know for a fact is something you'd never do -- there had to be something more to it. Then I registered the 'dare' comment.""

"Why would I not be a male stripper?" I flexed my muscles reflectively. "Something you're trying to tell me?"

She laughed. "I'm not saying you couldn't be -- I'm just saying that, knowing you as I do, it's not something I can see you being involved in."

I grunted, mollified. Actually she was right. Never in a million years, even if I thought I had the physique, would I contemplate doing something like that! Whilst the thought of a crowd of girls screaming over my nearly-nude torso was extremely titillating, I was enough of a realist to know it would never happen in my lifetime.

There was a brief silence. My mother continued looking at me.

"Something else?" I asked.

She nodded. "Actually, yes. And I feel not only embarrassed but silly in saying it...but here goes, anyway."

But instead of here-going she again paused, and took a sip of her drink. I waited patiently.

"I was just wondering...whether you felt you might need a bit more practice before Friday..."

I heard the words but they didn't signify anything to me. "More practice?"

"Yes. I mean, you've only done it once, briefly, the dressing up I mean, and I know Friday is really a try-out, too...but don't you think you should try again -- perhaps a couple of times, before then..." she was looking at me oddly, almost appealing to me "...just to make sure you've got it completely right?"

The penny dropped then, and so did my jaw. I looked at her in wonder. "Mum, you want me to dress up again?"

She nodded again, silently, her eyes liquid in the harsh light from the television set.

"You want to see me as a girl again?" I didn't know whether it was anger or incredulity I felt. I was confused.

"I think I'd like to, yes," she admitted quietly.

I felt the corners of my mouth turn down. "I thought last night, when we were chatting with Jean and I was dressed like that, that you might have preferred to have had a girl instead of a boy for a child. Looks like I was right!" I couldn't disguise the bitterness in my voice. I felt a bit choked up. Had my feelings been right? Had my mother been regretting her boy-child for the last seventeen years?

Startled by my vehement reaction, she got up quickly and came over to me, kneeling in front of me and raising her hand gently to my cheek. I jerked my head back, feeling tears pricking the back of my eyes.

"I don't mean it like that, John," she said soothingly. "I love my boy...my man. You've turned out just as I had hoped, and managed it without a father figure in your life. I'm proud of you."

"Then why-?"

"However much I feel about you, no mother with only a male child, or children, will ever stop wondering how a daughter might have turned out had she had one. I won't deny I'm not envious of my friends with daughters, they've had the fun and the joy of seeing them grow, and of dressing them up to look pretty and nice, and some of them of seeing their daughters married, walking down the aisle like a princess all in white, looking radiant and happy. I have never had that, and never will, and will always wonder, but it doesn't mean I didn't want you as you are, or think the less of you."

"So what is it about this girl thing?" I wanted to know.

"John, last night, without intending to, you gave me the opportunity of seeing how the daughter I never had might have looked at this point in her life. I can't explain how I felt when I saw you looking like that. It was as if history had been re-written. I saw before me my beautiful teenage girl just as I had always envisaged her in my mind's eye, and it was you and Jean who gave me that chance!"

"OK," I said non-commitally. What was this 'beautiful teenage girl' comment? However, I wasn't stupid. I could see what she meant, could understand what she was telling me. My petulance dissipated as I stood up, bringing her with me, led her to the settee and sat her down, dropping easily beside her.

I gave her a hug. "You want to see your daughter again?" I said.

She hugged me back and nodded. "If you don't mind. I know that after Saturday she'll disappear again forever, and I just wanted the chance to spend some time with her. Do you think I'm a silly old woman?"

"Yes, but I still love you."

She slapped me, playfully.

I made a decision. "OK, Mum, you're probably right. Yesterday Jean helped me, and that's why you got to see me as Miss Perfect. I suppose I should try to get used to dressing up on my own, even putting the make-up on myself...but you could help me with that, if needs be, couldn't you?"

She nodded eagerly.

"Tomorrow, then," I told her. "Tomorrow when you get home Miss P will be here to greet you. I can't guarantee she'll look as good as last night, but hell, we girls have got to learn sometime how to look as great as we can with the little we've got!"

My mother kissed me on the cheek. "Thank you. I know it's something you don't really want to do, but I'm grateful to you. I love you, John."

"Hey!" I wiped my cheek. "I love you, too, but I prefer my stubble black, not lipstick red!"
 

*          *          *
 
Mindful of my commitment, when I got home the next day I freshened up in the shower, and showed a razor to the light stubble on my face. Then with a towel wrapped around my waist I sat on my bed and dried my hair.

Finished, I ran experimental fingers over my body. I was still smooth from when I had shaved on Monday. I finished towelling off, and then stood naked in the middle of my bedroom, working out where to start.

First, I rummaged through the small suitcase Jean had left, which contained not only make-up but lots of lacy underwear. Perplexed by what exactly was in there I upended the contents of the case onto the bed, put it in a corner, and examined the residue.

As I sorted out the pile of clothing into panties, bras, and whatever else, I felt my penis swelling uncontrollably. There was absolutely no doubt whatever that the flimsy, lightweight clothes girls wore under their dresses had the power to turn a man on, even when they weren't wearing them! This man, anyway!

I picked out a peach-coloured bra and matching panties that were of a material so cobwebby that I imagined my erect member poking a hole in them as I tried to manoeuvre them over it. The material, however, was much stronger than it looked, and extremely elastic, so that as my excitement ebbed I was able to push my boy bits downwards and backwards between my legs and feel them safe and secure within the constraining fabric.

After a bit of mental spatial exercise I worked out that the best way to wear the bra was to put it on with the inside out and upside down, and fasten it at the front before swishing it round my chest and putting my arms through the straps. This worked a treat, and remembering Jean's idea I put a couple of pairs of my rolled up socks into the bra cups.

I stood up straight and wiggled my body. The panties felt immediately natural and comfortable to wear, the bra felt a bit odd about my torso and the lumps at the front strange at first, but looking in the mirror I felt reasonably satisfied that I was beginning to take on a girly shape again. There was something peculiarly sexual about being a male in female underclothing, and the old trouser snake started its twitching game again. I was amused at how such thin material kept the old boy under control.

Sitting in front of the mirror I experimented with the bag of make-up. First, I knew, Jean had rubbed some skin-coloured cream all over my face. I found the pot of foundation and scooped some out with my finger. Then I dabbed it all over my face before smoothing out the dabs with the tips of my fingers. When I had finished I saw, to my satisfaction, that any hint of five-o-clock shadow appeared to have been eradicated, and my face had a healthy glow.

The eye bits were trickier, and I used a lot of tissue 'rubbing out' and starting again, but finally I was satisfied with what I saw. My eyelids had understated colour and I had managed to outline my eyes with a black pencil, avoiding what I had heard Jean call the 'panda look.' More difficult had been the mascara, and I had narrowly avoided putting my eyes out with the vicious looking applicator on more than one occasion, but again, at the conclusion, I was fairly happy with my now long dark lashes.

Again, what appeared to be a fairly simple task was more complicated than it looked. Lipstick had this strange way of smearing itself in places you didn't want it to go, and I used up quite a bit of toilet paper before all the smudging disappeared and I had what I felt to be eminently kissable lips.

I avoided the blusher after two failed attempts. Whatever I did with it, I looked like a clown. It came off and stayed off.

Now came another tricky bit. Jean had put my tights on me last time, and I only vaguely remembered the operation. I knew it had something to do with working from the toes up, so I scrunched up one leg of a pair of black shiny tights and, sitting on the bed, eased them on.

I quickly worked out that you couldn't get one leg completely on and then start on the other. No, it wasn't as easy as socks. You had to work both legs up bit by bit, up to the knee with one leg, then the other, then up to the thigh with one leg, then the other, until with a bit of bum-wriggling and hip-swaying you managed to work the top of the tights around the waist. All this while trying to avoid poking a finger through the darn things! The only plus I found with all this was the incredibly sexy feeling of the tights once they were on my legs, smooth, lightweight, stretchy and supportive. I almost had an orgasm walking around in them, just like last time!

Finally I looked at the dresses Jean had brought. I wasn't going to wear the little black number again, that was reserved for Friday and Saturday. Of the two remaining, one was a flimsy summer dress with thin straps and the other what I later learned was a shift dress with a rounded neck and no sleeves. It was also 'fitted,' which meant when you wore it, it clung to the shape of your body.

After trying them both on, I decided on the shift dress, thinking it made me look much more girly, and after all that's what my mother wanted. The only problem with it was the zip, which ran down the back and caused me a great deal of contortion and swearing before I figured out the best way to do it.

The shoes were easy, they just slipped on, and I reached for the wig that Jean had left, and a hair brush.

Hell's bells! Having put the thing on I found that when I tried to brush it, it slipped out of place all the time. Because I'm pretty quick, it only took three or four cuss-words and two or three times stretching down to pick it up off the floor to make me realise that if I brushed it pretty carefully before I put it on, I wouldn't need to do much work on it after it was in place.

I looked at myself in the full length mirror.

Call me narcissistic if you like, but there was that babe again! She didn't look quite as...polished as I had seen her last time, but in essence she was everything I had aimed for. I fancied her something rotten, but I suppose that's a bit like saying you fancy your sister. A very odd feeling, and the boy bits were straining big time down there trying to show their appreciation as well. If only, I thought to myself, I could meet a real girl half as nice looking, one who might just fancy me...

I just hoped my mother would appreciate all the trouble I'd gone to.
 

*          *          *
 
Looking at my watch, I wondered where the time had gone. No wonder it took women so long to get ready. My mother would be home shortly.

I decided to get a meal ready for us, and ran downstairs to the kitchen. Well, perhaps ran is the wrong word. The shift dress didn't give my legs much freedom to operate properly, and I was soon reminded of the slight heel on the shoes. I negotiated the stairs very cautiously indeed.

As I began organising things in the kitchen I realised that food is pretty messy, and the last thing I wanted to do was muck up Jean's dress. I found Mum's pinafore, a sort of apron with a bib that had frilly bits all around it. I tied it up at the back in a bow, and got on with things.

It took me a while to get used to the normal cooking operations whilst wearing female apparel, of feeling the light touch of the dress as it brushed the nylon of my tights, making a strangely sexy swishing sound as it did so, and having hair flopping over my face whenever I leaned forward to cut or chop, and a mental image flashed before me. I visualised my mother shaking the hair back from her face as she prepared food or wrote a letter or did some sewing. Now I knew why, and I also remembered the girls at school wearing their hair brushed back and fastened in a pony tail! Vanity has its drawbacks! As I reached and stretched I felt the elasticity of the bra straps marking my every movement around my chest and shoulders.

My mother came home just as everything was bubbling away nicely, steam issuing from saucepans in a very homely way, and found me at the sink washing up a few pots and pans.

I sensed her standing in the doorway, watching, and glanced round.

Her face was a picture. She was staring wonderingly at me, her mouth slightly open. I grinned.

"John?"

"Who else?" I asked.

She entered the kitchen and sat down at the table, shaking her head. "I don't believe this," she said. "If I didn't know it was you, I'd think a real live girl was in my kitchen."

I went over to a cupboard and brought out a bottle and glass, and poured her a little of her favourite tipple.

"For tonight," I told her, handing her the glass, "I am a real live girl, and that real live girl is your only daughter. And your daughter has prepared a meal which is almost ready, so get changed while I lay the table so we can eat it while it's hot!"

I shooed her away and got on with things, and by the time she returned the food was on the table. We sat down to eat.

It was indeed an interesting evening. My mother spoke to me, treated me, as I had observed her conversing and reacting with any other female with whom she was spending time, and I was achingly aware that her attitude towards me was totally different to that which she employed when I was in my male persona. I, too, was aware of myself responding to her differently, and realised with a sudden shock of comprehension that I felt almost completely female in her presence.

Our conversation never halted, and we discussed a variety of subjects, of things and people, without so much as a pause. Our normal evening chatter would be very intermittent, interrupting television advertising time between programmes and not really saying anything, just reassuring each other that we were still there. I'm not saying my mother and I rarely spoke, because we often had intense discussions, but in comparison to our normal evening discourse tonight we sparkled. I enjoyed it intensely.

Finally, as we prepared for bed, Mum took me to one side and gave me a hug and a long and loving kiss on the cheek.

"What's that for?" I asked, embarrassed.

"Just for being you," she told me. "You've always been a lovely son, and now I know that, had you been born a girl, you would have grown up no differently. Thank you for tonight. You've made me very, very happy."

I hugged her, embarrassed by the brightness of unshed tears in her eyes, and as I got changed for bed, and underwent the interminable task of removing my make-up, I pondered over the evening.

Had we actually got on better tonight? I mean, we always 'got on,' but tonight seemed different to me. We had sparkled off each other, gelled, integrated in a way I had never experienced as a male.

Something at the back of my mind was asking me whether I was starting to enjoy my girl persona, perhaps even beginning to prefer it, but I quickly tossed that idea into oblivion. Whilst I had undoubtedly thoroughly enjoyed the evening, this was being done to win a bet; this was for the beer, wasn't it? There were no other subtle underlying reasons for my doing this, surely?

I had almost convinced myself that this night would be sufficient; but the next evening I found myself hurrying home from work with no other thought in my head than to be my Mother's daughter once more.

Showering and changing felt perfectly natural -- it was as if my body and mind had finally accepted that sometimes I wore masculine clothing, and sometimes feminine. Of course, my boy bits reacted as usual to the first touch of the lightweight, delicate feel of female underwear, but eventually became controllable. And, whilst I wore just a plain bra and panties and the summer dress that night, it was as magical, both for me and my mother, as the first.

At the end of that Thursday night I lay in bed with my arms behind my head and stared at the ceiling in puzzlement. I had actually enjoyed being a girl -- twice! Was I going through some strange sort of transformation? Was it possible that my physical and mental states were being slowly feminized because of a silly bet over alcohol?

Oh well, tomorrow night was the big test. At least Jean would be helping me get dressed and made up, so I would look as good as I ever could under the circumstances. How long, I wondered, would it take my pals to discover who I really was? Not long, I guessed, ever the eternal pessimist.

On the other hand, perhaps my strangely surreal acceptance of this alternative female role had subtly altered me, made me not only different in my mental attitude but also, to an extent, in my physical appearance. Maybe I was, in fact, changing into a girl.

I shook my head as sleep drifted over me. I didn't believe in magic, or the supernatural, or things that went bump in the night...
 

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