You Bet!

Part 2

By Kim Johns

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On Saturday afternoon I telephoned Jean.

"Oh, hi John. How are you feeling?"

I grunted, my head still swimming a little, my mind clearing slightly. "Jean, I had a really strange dream last night," I began.

She laughed. "Oh, yes?"

"Yes. I dreamt you agreed to take me to a party dressed as a girl ..."

"Yes, but only if I thought you could get away with it."

Silence on my part. Then: "You mean it's true?"

"Well yes. You said you'd do it if Harry and Barry paid for your beer for six m..."

"Shit. Still, I'd never pass for a girl, would I?"

There was a silence from Jean this time.

"Jean?" I said. That silence had been just a little frightening, and had lasted just a little too long. I felt strange constrictions in my stomach, and a sudden urgent need to urinate.

Cautiously, Jean said "Actually, John, I think you might. I'd need to sort a few things out for you, but I think you just might be able to do it!"

"You mean I look like a girl?"

"No, John, that's not what I mean. But if you are going through with it, I think you have half a chance of getting away with it."

I thought about that. Finally, "Can you think of any way I can gracefully get out of this?" I asked her.

"Oh, yes," she told me immediately.

"How?"

"Well, you just buy Barry and Harry beer for the next six months."

I said a word that she pretended to be intensely shocked by.

"Of course," she continued, "If you've really decided not to do it ..."

I interrupted. "You've got the final say, though, haven't you? You can stop it?"

This, I thought, would be my fail-safe. Jean would soon see I could never be mistaken for a girl, and tell the boys all bets were off.

"Yes. I wouldn't let you or my girl-friends down."

"What have I got to do?" I sighed, bending to the inevitable.

"Well, I thought I ought to come round in the week and see what we can make of you. I'll bring some bits and pieces with me, and we'll try you out."

"OK." It was my turn to be cautious. "When did you have in mind?"

"How about Monday? Then if everything works and it looks good, we've still got a few days before the weekend to perfect everything?"

I can't say I liked the sound of that, and the ache in my stomach and genital area grew in proportion to my anxiety, but I agreed. What else could I do? If I refused point blank the guys would never let me live it down. And there was always the beer. There would always be the beer. The die was cast.
 

*          *          *
 
The doorbell rang on Monday night, and when I answered it Jean stood there with a smallish suitcase in one hand and a long green canvas dress carrier in the other. Damn. I'd hoped she would have forgotten, but she had a memory like an elephant. Still, hope springs eternal.

"Come to stay?" I asked, taking the case from her and leading the way upstairs.

She laughed. "Just some odd bits and pieces. Make-up, underwear and some dresses. Where's your mum?"

"She's out this evening. Won't be in 'til late." Subconsciously my brain had registered the word 'underwear.' What had I let myself in for?

"Oh, that's good. We won't be interrupted then."

I dumped the suitcase on my bed. "OK, then. What do you want me to do?"

Jean smiled. "It sounds a bit forward," she said, "But you need to strip off."

I sighed. "All right, let's get on with it."

I turned my back on her, and stripped down to my underpants. "How's that?"

"You're a bit hairy," she commented, rubbing a gentle finger over my arms and chest. "Not too badly, but you're going to need to shave all over. You don't see too many hairy girls. Still, I thought of that." She took a bottle from the case, and we went into the bathroom. Jean turned on the taps, and shook liquid into the hot water as it steamed from the taps. It immediately foamed up, releasing a pleasing, but intensely feminine, fragrance into the room.

"I want you to have a bit of a soak in the bath, and then shave your whole body," Jean told me. "Legs, arms, chest, and under your arms. And your face. Girls are nice and smooth all over, and that's what you're going to have to be. When you're done, and you've dried yourself, put these on and come back into the bedroom."

She handed me what appeared to be the smallest pair of panties I had ever seen, not that I had seen many, soft and white with a satin feel. Embarrassed, I quickly put them on the bathroom stool, feeling my penis quiver in anticipation of what I was about to do.

Jean left me to it, and I sank into the bath, relishing the scented water that seemed to soak into my skin, relaxing me, softening me. I leaned my head back, closing my eyes. I'd never realised a bath could feel so sensual before. The steam enveloped me and I drifted away ...

I opened my eyes suddenly, aware that the water was starting to cool, and grabbed my razor. Starting with my legs I began shaving. It was a time-consuming task, but I tackled it with patience, pausing every now and then to slide my hands over the newly hairless parts of my body and revel in the unaccustomed softness and smoothness. Oh my God, I thought, I'm beginning to feel like a girl!

Finally finished, I dried myself carefully and picked up the panties, sure they would never fit me. However, I was mistaken. Pulling the soft material up my legs and over my hips I realised how stretchy the fabric was, hugging my body intimately. They felt comfortable and snug and protecting. I enjoyed wearing them, and again felt the twitching of my manhood as it became excited at the sensual feel of the garment.
 

*          *          *
 
I returned to my bedroom, where I found Jean had emptied the contents of the case onto my bed. She turned as I entered, and looked me up and down appraisingly.

"You've done a good job," she remarked. "How do your panties feel?"

"All right," I said, blushing hotly as she glanced down at the bulge between my legs. She smiled.

"That's no good," she remarked, indicating my erection, "We'll have to get rid of that. Girls don't have penises. Well, not their own, anyway."

She reached for me, pulling my stiffened manhood free through a leg of the panties, and stroked it with her thumb before glancing at me with a wicked glint in her eyes. I shivered, and it wasn't with cold.

"It would be a shame to waste this," she murmured, looking me boldly in the eye. "Perhaps we should give it one last fling before you renounce masculinity forever!"
 

*          *          *
 
As my mind tried to compute what she meant by 'forever,' she pulled me forward by tugging gently on my erect member, then sat on my bed. She lifted her feet and swung them up onto the bedspread, then slid backwards towards the pillows. My knees touched the edge of the bed, and I moved forward and knelt in front of her as she continued softly pulling me. Slowly she lifted her skirt with her free hand, circling her waist with it and revealing a pair of lacy white panties. Moving her hand again she peeled the panties down to her knees, revealing the triangular-shaped growth of hair at the base of her stomach. Giving another gentle pull she opened her legs a little, and I felt a gigantic aching in my testicles and the enormous growth of my penis.

"Barry," I began, but her free hand now covered my mouth. She leaned up towards me, and kissed me on the lips, a warm, exciting, dangerous kiss, slipping her tongue into my mouth and playing with mine.

I compulsively moved forward and entered the warm, slippery dampness of her, filling her completely, feeling her clasping me inside her. Her arms folded around me, pulling me close, and our lips kissed and our tongues played, and I moved within her in a rhythm programmed by nature until, unable to restrain myself any longer I felt myself burst inside her, felt the urgent flowing of juices from me to her, and sank exhausted on top of her.

She nuzzled my ear as my penis slowly deflated, until I rolled from her and lay on my back on the bed, wondering what had just happened between us. I hoped in my heart it wasn't just sex, but her next words disillusioned me.

"That," she said, "Was between you and me. Barry will never know about it. Agreed?"

I nodded dumbly.

She smiled down at me. "Thanks. Now, when you feel able, we've got a bra fitting to do!"

I stood up and adjusted the panties, but Jean put a hand out to stop me.

"Let's see if we can make this right," she murmured, and walked behind me.

Placing one hand over my stomach she pulled the top of the panties away from my body, and slid the other hand down inside the panties until the tips of her fingers found my penis. Palm towards my body she moved her hand slightly downwards and then pressed gently, forcing my penis and testicles back between my legs. Holding her hand there she then adjusted the panties so that they were pulled tightly upwards, and slid her hand out.

"How does that feel?"

My manhood was held securely between my legs by the elastic pull of the feminine garment, and I felt surprisingly comfortable. Looking downwards, I saw the smooth roundness of my stomach and no masculine lumps pushing the panties out of shape.

Jean smiled. "That's a bit more girly," she said. "We don't want strange bits sticking out from your body suddenly, do we? In a room full of girlies, someone just might get suspicious!"

She picked up a white satin bra from the bed, a match for the panties, and turning it inside out and backwards showed me how to fasten it at the front of my chest before manoeuvring it around my body and putting my arms through the straps. Once on, she fiddled with the adjustable shoulder straps and stepped back a pace to look at me thoughtfully.

"You need boobs," she remarked. "I'll have to think about that. In the meantime, let me have a couple of pairs of your socks."

I fished in a drawer, puzzled, and handed the socks to her. She rolled each pair into a ball, and then put each ball into one of the bra cups. Again a bit of fiddling until she smiled. "What a well-endowed girl you are," she remarked. "You've got a bigger bosom than me!"

I moved my head in a circular motion and shrugged, easing the foreign feeling of straps across my shoulders and taut elastic round my torso. There was a buzz of excitement slowly building up inside me, a strange eagerness suddenly to know just what it would be like to be female, to wear those flimsy fripperies that, as a male, always excited me when I saw women wearing them, sending my pulse racing.

Jean gently pushed me in the chest, jerking me out of my reverie, and my knees folded against the side of the bed, forcing me to sit.

"I've brought tights with me," she said mischievously, "But you look a bit like a stockings and suspender girl to me. However, that can come later. In the meantime, I'm going to put these on you because I don't want you laddering them."

She showed me a pair of shiny black tights, and deftly inserted her hand into one leg before folding it up and easing it over my foot and up to my knee. She repeated the action with the other leg and made me stand up. She then teased the rest of the tights bit by bit up each thigh in turn until she reached my crotch. Again with that impish grin she smoothed the elastic material up into my groin sending erotic messages buzzing to my brain before finally pulling the garment round my waist. I don't think I had ever felt anything quite so sensual as the pull of the tights massaging my newly smooth legs as I experimentally walked around the bedroom, getting used to the feel of them.
 

*          *          *
 
Somewhere between my legs in its secure little nest I felt my penis twitching yet again. Jean noticed my quick downward glance and chuckled. "It's OK," she told me, continuing quite mistakenly: "There's nothing moving down there!"

"Now then," she continued briskly, picking up a small bag from where it had lain hidden amongst the female fripperies covering my bed, "Come and sit over here by the window."

She moved my bedside chair close to the light and I obediently sat.

"This may take a little time," Jean told me, putting an assortment of small tubes and brushes on my dressing table, "And you may not like the eye bits, but if you do what I tell you everything should work out fine."

She picked out a pair of tweezers. I eyed them suspiciously.

"I'm going to pluck your eyebrows," she explained.

"Hey, guess what," I told her. "No, you're not!"

Jean smiled. "It won't hurt. And I'm not going to do much, just shape them a little bit. Yours are a bit bushy, so if I go carefully they'll look OK whether you're dressed as a boy or a girl!"

"Hmm."

Taking my response as agreement she began to torture me, and I did my hurt baby routine, mainly because it hurt like hell and I was a big baby.

She finally put the metal instrument away with a rueful smile and reached for the small bag again.

"Sorry to stop," she murmured, "I could see you were enjoying that."
 

*          *          *
 
As she applied the various items of make-up to my face and, particularly, my eyes, she issued instructions, telling me to turn this way or that, to close my eyes, open my eyes, stare at the ceiling or to the left and right, and all the time I could feel light touches to my eyelids and cheeks, to my eyelashes and lips, catching sight of brushes and tubes and pencils with my peripheral vision. It seemed to take ages, but finally Jean looked down at me critically, and blinked in apparent surprise.

"Well," she said, "I actually don't believe this. You're very pretty!"

"Don't be daft," I told her, standing up and glancing in my small wall mirror, "Blokes aren't pretty..." I stopped short, staring in amazement at the girl who looked back at me. She was indeed pretty, with make-up that complemented her features in a minimalistic way, and the only jarring anomaly was her hair, which was short for a girl and still recovering from the effects of the bath.

"Bloody hell," I exclaimed.

Jean put her hand on my shoulder. "I'm sorry to say this," she told me, "But more and more I'm beginning to think you might just win this bet of yours!"

"But my hair," I started to say, and she put a finger on my lips.

"I think I can do something with your hair, even though it is short, but just in case," and she leaned over to a small carrier bag beside the bed, "I've got this."

'This' was a wig which she shook fairly vigorously before placing it on my head and tugging it in various directions until apparently satisfied with the effect. "Now sit back down," she ordered, and began gently brushing the hairpiece.

Although the hair only came to my shoulders, I again experienced a feeling of sensuality as it swished against my bare skin while Jean styled it, brushing and combing until satisfied.

"Now look in the mirror," she said.

I could not believe that the gorgeous creature staring back at me was in fact me! If I had seen my face across a crowded room I would have wanted to approach me and try to chat me up! These confused thoughts sped across my mind as I touched the hair surrounding my face.

"Come on, beautiful," Jean urged me away from my reverie, "Dress and shoes and then we'll form an opinion!"

Jean had hung the dress carrier in my wardrobe. Unzipping it she looked thoughtfully at the items within before finally making a decision and easing one out.

The dress she showed me was black, with thin straps across the shoulders and a slightly scooped neck, and was hemmed with some sort of net material in a scalloped fashion. Jean unzipped it and held it in front of her. "Step in," she commanded.

I stepped in, and felt the light, smooth material kissing my skin as Jean lifted it up my body, pausing once to let me put my arms through the straps and then again as she eased it over my bust, being careful not to disarrange her boob job. Finally she stood behind me and zipped up the dress, and I felt it arrange itself around my figure, close but not uncomfortable, and feeling very, very sexy. My penis twitched again.

"I got the largest size shoes I could find," Jean said, producing a pair of black patent leather court shoes with (I discovered later) a two inch heel. "Try 'em on, they're sevens."

"My size," I muttered, slipping my stockinged feet into the shoes and taking a few steps around the room, "And they fit perfectly!"

"And you can walk in them straight away," marvelled Jean. "Have you done this before?"

She moved around me, straightening the dress here and there, lifting the skirt to check my panties were still in place properly and comfortably, and further minutely adjusting the bra to improve the shape of my upper body.

"There," she said, finally satisfied. "Have you got a full length mirror anywhere?"

The only one we had was fitted to the door of my mother's wardrobe, so we went into her bedroom for a final assessment.

I stood in front of the mirror amazed and not a little frightened. Gone was the reflection I was so used to seeing, the somewhat unkempt youth who tended to dress in old jeans and t-shirts, in fact gone was the John I knew so intimately, vanished without trace. In his place stood a pretty young lady (I hesitate to use the term beautiful when applying it to myself, but I was extremely taken with her!) with a trim figure and nice legs, dressed for a party and looking very attractive indeed. I felt a rush of sexual excitement, not only at the appearance of this creature in front of me but also from the combined feel of the clothing I was wearing, a feeling of sexy sensuality, and the knowledge that this gorgeous creature was me! My penis stiffened and I experienced an involuntary orgasm, feeling the hot semen rush into my tight panties. I groaned and put my hand out, leaning weakly against the mirror.

"John, are you all right?" asked Jean, concern spreading across her face as she put her arms around me to steady me.

"Sorry," I said thickly, and explained what had happened, somewhat shamefacedly. Jean hugged me. "Don't worry," she said, "I'm not surprised. These are lovely clothes to wear, and although I hate to admit it you look absolutely stunning in them. Wait here."

She vanished, and I heard the sound of a bathroom tap. When she returned she was holding a wet flannel and a towel.

"Lie back," she said, and I felt her gently lifting the skirt of my dress and pulling down my tights and panties. Carefully she cleaned me up, and dried me, before pulling the panties and tights back in place and smoothing down my dress. I sat up and hunched forward, still a little dizzy, leaning my elbows on my knees and with my head in my hands, feeling confused and worried as she returned to the bathroom.

Neither of us had heard the front door open and close, or the sound of feet on the stairs. The first thing I became aware of through my fugue was my mother's voice as she stood outside the bedroom door.

"Hello, Jean," she said in a surprised tone, "Where's John? And who's this!"

Startled, I rose to my feet, a blush starting on my face, but twisted my foot in the unfamiliar heeled shoes and lurched sideways.

My mother took two steps into the bedroom and caught my arm as I staggered, steadying me, as Jean also entered to lend a hand.

"Are you alright, dear?" asked my mother, concern written over her face. "Sit on the bed and I'll get you a drink of water." Motioning Jean to stay with me, she left the room.

I grabbed Jean's hand. "Oh God, what am I going to do now?" I whispered, terrified, feeling desperately that I wanted to urinate. For my mother to find me like this was the worst thing imaginable. My anticipation of the unknown was causing pain in my stomach, tautness in my groin. I felt pale and weak. What would her reaction be? It felt as if the end of the world was, finally, at hand!

Jean shook her head, baffled.

"I suppose we'll have to tell her the truth," I muttered, visions of I knew not what kind of response my mother would display when reacting to the news that her son was a drag queen!

"Let me try," Jean said as my mother returned and handed me a glass of water. I took it gratefully, muttering my thanks as I raised the glass to my lips, effectively covering my face.

"Where's John?" asked my mother again, turning to Jean.

The girl paused. "Harry and Barry set him a dare," she explained carefully, doing her best not to tell a downright lie. "I came over to help him sort it out."

Mum laughed. "What sort of a dare?"

"He has to go to a party with me."

Again my mother laughed, her brow furrowing in puzzlement. "I'm sure that would be no problem for him, Jean. You know how he enjoys parties. I'm surprised Barry is letting him take you, though."

"Well," said Jean slowly, "It's more a matter of me taking him." She paused again as my mother looked curiously at her, then at me. "It's a girls-only party," she blurted.

Mum looked even more puzzled. "So you and your friend both came over to help John go to a girls' get-together?" she said slowly. She glanced at me again, then back to Jean, then, startled, back to me, looking closely at my partially concealed features as sudden realisation dawned.

"John?" She said to me, moving the hand that held the glass away from my face.

I sighed and put the glass down, looking up at her, the long hair of the wig caressing my cheeks as I did so. "Mum," was all I could think of saying.

My mother took a step backwards, mixed emotions flickering over her face as she stared at me. "What have you done to yourself?" She said, both hands raised to her mouth.

"Mum," I repeated, trying to start an explanation.

"Just look at you! You...you look..."

She again glanced at Jean, then back at me, then back at Jean. "John..." she faltered, gazing incredulously at the sight I presented.

My cheeks blazed. I wanted to tear the wig from my head and wipe the make-up from my face, to show her I was still her son beneath the feminine facade.

"Stand up," she ordered faintly.

I carefully rose to my feet, remembering to treat the shoes with caution, and faced her, unconsciously smoothing the skirt of the dress down from my hips as I did so.

She put out a hand and gently felt the hair around my shoulders, then cupped my chin in her hands. "Just look at you," she said. I saw her eyes grow soft, misty.

"Mum, I can explain..." I began, but she placed a gentle finger against my lips.

"I often wondered what it would be like," she said, "If I'd had a daughter, how she would look now."

My mother was being totally confusing. She was looking at me with a strange light in her eyes, sentimentality mixed with curiosity and wonder.

I looked at Jean, then back at mum, puzzled by her reaction. The least I had expected was a grade 12 storm, certainly not this seemingly docile acceptance.

"Now I know," she continued. "John, you look beautiful." Surprisingly she put her arms around me and gave me a hug, and a kiss on the cheek. "Jean," she turned to the girl," Did you do this?"

Jean smiled nervously. "Well, yes," she said, "John wanted to know if I thought he could get away with it, so I said I'd help him dress up and see."

"And what do you think?"

"I think there wouldn't be many, if any, of the girls who would guess he wasn't one of them, unless he made a really big mistake."

Mum nodded her eyes bright with unshed tears. "I think you're right." She looked at me again, smiling. "My daughter!" She exclaimed. "Who would have thought it?"

"Mum," I intervened, shifting my body uncomfortably," I'm still your son. I'm only doing this as a dare!"

She laughed, suddenly her normal self again. "Yes, I know, but let me enjoy the occasion!" she said.

"So you're not mad at me?"

"John, why should I be? It's not as if you're a secret cross-dresser, is it? Or is there something you want to tell me? You look great for someone who's doing this for the first time!"

"Mum!" I protested, feebly.

"Come on, the two of you," Mum ignored me, "Let's sit down in the front room and have a drink. I certainly need one after this shock."

As I turned towards my bedroom she caught hold of my arm. "Where are you going?"

I stopped. "I'm going to change out of these things," I started to say.

"Please don't. If I'm to have a daughter, let me have her for as long as possible, John. Come and sit down as you are. It will please me, and it'll be practice for you."

With some reluctance I followed my mother and Jean into the front room, a little uncomfortably and incredibly embarrassed. My mother was taking my sudden transformation better than I would ever have imagined, and as we sat and drank and chatted about the party, and my new appearance, and life in general, the sneaking feeling crossed my mind that, perhaps, all my life she had wished I had been born a girl rather than a boy. The thought made me bite my lower lip a little as a tinge of jealousy and resentment spread over me. Could it be true? My mother secretly wishing for a girl, hating the fact that I was male? Surely not.
 

*          *          *
 
Changing out of my female attire and cleaning the make-up from my face as I prepared for bed, my brain ached with confusion. Jean had been impressed by my transformation, and I had to confess that even I had been somewhat startled by the female me; the fact that my somewhat unpredictable mother had also accepted my 'change' was strangely unsettling, and as I settled down to read before sleeping I wondered just what sort of outcome this odd wager was going to have on my life...
 

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