With only 3 days left of their bet, things have taken an astonishing new twist. I t is now Dorothy's sister Sally that is on the back foot. Not only is their mother fawning over Dorothy, she is also taking her shopping while Sally must go to work. Is this now a straight run home down to the finishing line for Dorothy or will there be any more unexpected twists or turns?

  

Wearing The Pants

by Catherine Rose

Chapter 8 – Shopping With Mum

 

I knew that shopping with my mother was going to be something special from the moment she insisted on selecting the clothes I would be wearing for the day.

It wasn't the clothes themselves, white fitted trousers and matching white shoes I'd worn before, or her red scoop-neck sweater (that I'd secretly tried on the previous day). It was that she took charge of all the details. She gave me money for the bus, directions where to catch it, what time, where to get off, and where to meet her in town. I felt much safer in mum's hands than I had since this whole nightmare began. She even lent me her gold handbag with a chain strap that she didn't even let Sally borrow.

She came up to me in food hall, gave me a big warm hug and quickly explained her plan for the afternoon.

"I want you to choose at least two complete outfits of your own, one for each of the next two days as well as your own sleepwear,' she said. " I will help you in your selections but you can have the final say."

Shopping with my mother was an amazing experience. She seemed to focus only on dresses and skirts with hardly a single pair of pants to try on. Everything she chose for me was so delightfully feminine.

"Mum, I can't ever wear any of these," I said. "Why are you even having me try them on?"

"It's okay, Dorothy," she replied. "I know you have been trying on my clothes. I'd rather you not have to do it on the sly."

I couldn't be sure she hadn't been bluffing but I knew that the embarrassment on my face had given the game away.

"I want you to have your own clothes so you don't have to sneak around in other people's wardrobes."

"But, mum," I pleaded. "I can't go around wearing dresses. The bet was for only pants and even that is over in a couple of days. What will the girls say?"

"The truth is, Dorothy, it doesn't really matter what anyone else says. You are obviously enjoying your newly discovered femininity and that's okay. Most girls do, at least those that aren't embarrassed by it. For one reason or another, boys are completely discouraged from it. I think this is one of the things that causes aggression. Boys are forced by society to deny their tender side having to always show their toughness. I wish you had been born a girl so that you didn't have to go through life being only half a person. At the very least, I should have been encouraging femininity in you all along. But now that you finally realise what you have been missing, I don't think you'll ever be able to completely dismiss this part of you. So you might as well enjoy yourself while you can.

"As for the girls, you have already won the bet. You've taken everything they dished out till there's nothing more that they can do to you. I admit I was sceptical at first, but you have really proved your point – There is nothing wrong in expressing your femininity. What better way to drive home your advantage now than by wearing the very types of clothes the girls won't allow themselves to wear?"

I had to admit that mum's logic was hard to fault. I suspected, however, that she was also enjoying picking clothes out for me and dressing me up in them like a little girl playing with her doll. But it was clear that she had seen right through me so there was no point in pretending any more with her. So I allowed myself to be the daughter she seemed to want me to be. In fact I started to quite like it.

In some way it could have been even more embarrassing shopping with my mother than it was with my sister and her friends. They seemed to treat me more as guy they had roped into a sick game. With my mother, on the other hand, I felt no belittlement. She treated me like a real girl almost as if she was educating me in womanhood. She would follow me into the changing booth and tell me exactly how to put on and take off each item of women's clothing; how to walk in them; how to sit. And the strangest thing was I was really enjoying myself.

The first thing she bought me was the most delightful floral print blouse. I was awe-struck by it as soon as I saw it on the rack. I couldn't wait to try it on and once on I didn't want to take it off. It took all of mum's effort to persuade me to allow the shop assistant to wrap it up for me.

"You'll have plenty of time to wear all of your new clothes tomorrow, " she tried reasoning with me. "Right now you've still got so many beautiful things to try on that you won't have on any single item for very long anyway."

I reluctantly took it off and carried it up to the front register as suggested.

I found myself discussing things I never imagined I could have with anyone let alone with my mother. Who would have thought that I would be telling anyone which style of dresses I preferred, what colours I liked best, and which fabrics felt the nicest? I suddenly realised that my opinions as to what girls should be wearing stemmed from what I actually yearned for myself.

And it wasn't just about clothes that we talked. When we sat down for a coffee she even asked me how I felt about the male strippers from earlier in the week. I was very embarrassed by her questions at first but found it helpful to have someone with whom to talk it through. I realised that while I was excited by it all in the moment I wasn't at all attracted to men.

"I don't think I've ever met anyone as attractive as Sarah and Margaret," I openly admitted for the first time. "If I had the chance, I'd marry them both."

The weirdest thing with mum was that it was easier being her daughter than it had ever been being her son. That afternoon turned out to be a most profound mother-daughter experience for us. We became closer than I had ever been with anyone. She had suddenly become my best friend.

When it came to sleepwear, she insisted I choose a satin chemise and matching robe.

"Cute shortie jarmies may be fine for little girls but you need to start wearing proper ladies nightwear," she advised.

They were all so beautiful that choosing only one was near impossible. I wished I could have them all so I could put on whichever one I liked at any given moment. But I did find the most delightful leopard flower design in the most gorgeous blue I'd ever seen. I could hardly wait for night time to put it on.

While I loved the look and feel of the chemise, sleeping in it was another matter. I found it difficult to tuck it under just right while lying down. It would either ride up too high and tangle around my waist, or stretch too far down and pull on my shoe-string straps. Yet I felt so girlie in it that I figured it was worth a bit of discomfort and soon got used to it.

The most exciting thing about the next day was that I could choose whatever I wanted to wear for the first time since I made the bet. It was a marvellous thing to open my wardrobe and find dresses hanging there knowing that they were all my very own.

As it was going too be a scorcher of a day, I chose a light mini-dress, which I wore with a denim jacket to keep my shoulders warm till the day heated up. It was refreshing to still be able to wear denim even though I was dressing as Dorothy. The buttons were on the left side, of course, for I wasn't about to wear any male clothes on such a momentous day.

It turned out that I was too excited by my new-found freedom to stay in the same outfit for any length of time. No sooner had I put one on than I got the urge to try on something different. By midday, however, it had got so warm that I reverted to my summer frock and had lunch sunning myself on the patio. Being on my own, I slid the straps of my dress off my shoulders to work on a tan while flipping through some women's magazines.

This time, however, instead of just admiring the latest fashions, I started reading some of the articles. Apart from lessons in make-up, body care and health tips I picked up, I also got engrossed in a serialised romance. I enjoyed it so much I had to search through the house for back copies so that I could catch up on the bits of the story that I'd missed. I could hardly wait for the next instalment.

Sarah and Margaret came around after dinner, so I had to model my purchases all over again. Sally was decidedly testy. I think she realised now that she was going to lose our bet and wasn't taking defeat at all well. Sally and Margaret on the other hand seemed totally unaffected by it all and looked as if they were looking forward to our date almost as much as I was.

"You better dust the mothballs off your shortest dresses," I teased. "Your day of reckoning is nigh."

"Don't get too excited, young Dorothy," fended Sarah. "You haven't won yet."

"Besides," Margaret shot back, "I'm not even sure you'll be able to handle the both of us."

"Oh, I will," I assured them. "I haven't come this far for nothing."

I slept really soundly that night knowing that upon waking I would be only one day away from attaining my ultimate dream.

Friday came and went pretty unspectacularly. Being too excited to know what to do with myself I spent quite a lot of time reflecting on the previous week. I felt bullet proof. There was nothing I couldn't handle. I had adapted remarkably well to everything.

I noticed that I now held my hands mostly with my fingers daintily bent backwards to avoid my long finger nails catching on anything. Among other things, this allowed me to play my Playstation games again although annoyingly this usually caused my nail polish to chip.

Crossing my legs as I sat down had become part of the one action, something I now did without even thinking. Since I'd been wearing dresses and skirts I'd even caught myself unconsciously stroking my legs, a thing I'd noticed that girls sometimes do that drives me crazy.

But by far the biggest change was in the way that I walked. My gait had become quite rhythmic with curt purposeful steps, one foot in front of the other, that I noticed made my hips wiggle. And when I had to run, like when avoiding traffic while crossing the road, it was more like a gentle little trot so that I didn't trip over my high heels or bob my boobs too much.

While I hadn't known what to do with my hands since none of my clothes had pockets, I soon found it quite comforting to fold them across my chest under my breasts. Not only did this take the load off my bra but I also felt protected in a way I couldn't describe.

Having to constantly wear a bra was one thing I could never get used to. Sure I was grateful for the way it supported my breasts, I don't know how I could have done without one. However, I now sported a permanent monorail from the underwire, and my shoulders ached from the straps pulling down on them. It was always a relief to be able to go to bed at night time just to rid myself of those boulder holders.

As for the new arrangement between my legs, it was no problem at all. The fiddling about with clothes just to pee may have been annoying at first, but since I'd been wearing dresses and skirts it was just a matter of pulling down my panties and enjoying a quiet moment sitting down. I hadn't even masturbated in days, probably not since I'd started to allow myself to enjoy my femininity instead of fighting it.

And that was perhaps my biggest surprise – that I could learn to enjoy living as a girl. I'd always liked women's clothing, of course, when worn by attractive females. But I never dreamt how nice they'd be on me. Sure it was not all a cakewalk as my experiences with bras had shown. Yet I could never have imagined such freedom around clothes. I could effectively wear any of my male clothes and have that range extended tenfold through extra colours, styles and fabrics society only made available to women. This is not to mention such garments as dresses and skirts, pantyhose, camisoles, and accessories such as make-up and all manner of jewellery. I now felt naked till I put on some lippy and mascara. I also loved wearing bracelets and bangles on my wrists, while showing so much extra cleavage made a nice necklace almost a must. I only wished the girls had made me get my ears pierced so I could have tried on all their earrings, as I found the clip-ons much too painful to bother with.

But all these wonderful experiences paled into insignificance compared to the friendship I'd developed with Margaret and Sarah, and didn't compare at all with going on a date with them. I was on the phone to them several times during the day. I'd even missed watching the weekly episode of "The Gena Davis Show" because I was gasbagging with one of them at the time. I tried giving them a hard time over their 'impending doom' but they could give as well as they could take.

"How does it feel to have to dress like a real woman for the first time in your life?" I'd asked.

"I don't know," Sarah replied. "Why don't you tell me about it."

"I might practise on you some of the tricks I picked up from that male stripper," I'd say.

"If you don't measure up tomorrow night," Margaret warned, "I'll get that guy back to demonstrate on you what girls like from boys."

I easily drifted off into a deep sleep that night and unsurprisingly had what started off to be a very sexy dream. Margaret and Sarah were standing in a doorway of their room wearing identical clothes – a short-sleeved Angora top with a rounded neckline and a matching slip dress barely long enough to hug their cute little bottoms. Who would have thought you could look that good in wool? Everything they wore was in harmony with their pastel pink ensemble, lipstick, nail polish, even their pantyhose.

Provocatively they were running their hands over their bodies as if smoothing out invisible wrinkles in their clothes, all the while their eyes focusing seductively on me. I gravitated towards them immediately and soon their arms were soon all over me. I hardly noticed them easing me into their room until I heard the door slam shut behind me.

 

I looked around for the door but the scene had suddenly changed. I was now wearing those same clothes that I had moments earlier seen on Sarah and Margaret. I was standing outside and all I could see were houses in pink candy in whatever direction I looked. It was as if I had landed in fairyland or something. I started to panic. I started to cry. I started to run around aimlessly as quickly as my little pink shoes could carry me. But there was no one there. I was all alone.

The scene suddenly changed again. There I was, dressed as before, but sobbing away helplessly in my mother's arms. She was calmly stroking my hair and comforting me with her soothing voice:

"There, there little Dorothy. You are safe now. Everything will be okay. All your problems are sewn up … It's all sewn up … You're all sewn up … You're all sewn up … You're all sewn up…"

I continued to sob away uncontrollably until the door of my room mercifully woke me up from my nightmare.

"Congratulations, Dorothy" came my mother's voice. "The girls have conceded defeat. Your victory is all sewn up!"

"What did you say?" I said sitting straight up in my bed like a jack-in-the-box, scaring my mother half to death in the process.

"You've won," she replied trying to regain her composure. "You know, the bet? Victory is all sewn up. The enemy has conceded defeat. All you have to do is to come downstairs for breakfast one last time as Dorothy to prove you've seen out the whole week and you can start negotiating your prize."

Now that really put a smile on my face. I quickly jumped out of bed forgetting all about my dream. I slipped my feet into my fluffy slippers, wrapped myself in the satin robe, and skipped on down the stairs and into the kitchen.

 

Chapter 9 – Pay Day

The funny thing was that my sister didn't even go with us on our date. She had scored a date of her own, someone with whom she had been trading glances for quite some time, so she wasn't about to let that opportunity pass.

I didn't much care. Sarah and Margaret were the objects of my affection and they had both laid it on hard and thick a week ago so there was never going to be any doubt about their participation in their side of the bargain. True to their words, they turned up on our doorstep, totally "drop dead gorgeous". Both of their dresses looked like they had been sprayed on, accentuating their every bump and curve. Much as I had been able to pass as a girl over the last week, what little they had on between them left no doubt as to their gender. You should have seen how my father's eyes nearly popped out of their sockets as he answered the knock at the door. The only time his eyes left them was to slyly wink at me. We were father and son again and he wasn't about to say anything derogatory about my bet now.

It was my mother that seemed most ill at ease. Her mood seemed to go flat as I returned to being Jeremy buzzing in excited expectation of the coming night. She wasn't saying anything but I could tell that she was already missing Dorothy. I might have missed her too if it wasn't for the two babes that were about to escort me on the night of my life.

It hadn't been easy getting myself ready that afternoon. I found returning to men's underwear a bit of a let down. After the clothes I'd been wearing over the past week, my old clothes felt quite boring. It was my own trousers and shirt that now seemed to zip and button up back to front, not to mention being completely shapeless and without any style. I felt quite undressed without any jewellery and made a mental note to explore the male counters in jewellery stores at my soonest opportunity. My eyes looked featureless without make-up and my lips felt listless without lipstick. It was a strange sensation getting re-accustomed to being a male.

But one thing that hadn't changed was the bulge in my pants. No longer wearing a gaff, I was glad that my pants were as baggy as they were. The manner in which I carried myself when I walked seemed to have changed back to how I remembered it, helped no doubt by being able to wear flat shoed shoes again and no bra. There was no more of that girlie wiggle that I had feared might plague me forever. I felt marvellously masculine that night and I was certain that it showed.

We had no trouble getting into any club that night. Being arm in arm with Sarah and Margaret on either side meant that no one even bothered to look at me. Everyone's eyes were firmly on the girls all night while Sarah and Margaret, true to their word, kept their eyes firmly on me. I felt 12 feet tall. I wished that night could have gone on forever.

But all good things must come to an end, unless, that is, they get better! It had struck me that Sarah and Margaret hadn't needed much encouragement to follow through their end of the bargain. It seemed to me that they had enjoyed our date as much as I had. So it should not have come as a surprise when we ended up at their flat afterwards.

As I became aware of where we were heading, I was suddenly overcome with performance anxiety. Being with one such a girl would have been worrying enough. Being with two was positively outrageous. I wasn't quite sure what was expected of me in such a situation.

I need not have worried. They walked me up from the car to the front door of their flat in the same intertwined way we had manoeuvred all night. No sooner had the door closed behind me, I was being sensuously kissed and undressed by them. I hadn't even noticed when they had undressed themselves but then I suppose they had precious little to take off.

The three of us rolled around in all sorts of positions, holds, and combinations till it finally happened. There was Sarah lying back on the edge of the bed with her legs pointing towards opposite ends of the ceiling, while I knelt at the foot of the bed with my tongue dancing around the entrance to her cave. As I slowly rose to my feet, I slid my tongue in the valley between her breasts and onto her neck, when all at once my penis found its way into heaven.

Our bodies wriggled together as if dancing to a beautiful symphony. It was the most amazing feeling I had ever experienced. Surely nothing in the world could top it, or so I thought.

Suddenly I became aware of Margaret again. She was gently stroking my anus with something cold, a soothing gel of some sort. Then while she held onto the sides of my hips I suddenly felt something long and hard penetrating my rear. As Margaret gently rocked backward and forward into me I seemed to rock forward and backward into Sarah. The symphony by now was encompassing the three of us. I must have blown a fuse for my mind just completely fried.

It was not until we were all nestled together naked on the top of the bed that I noticed the strapped on dildo that Margaret was wearing. I could not believe that something so menacing could have possibly found space inside of me. Yet I wasn't complaining. I was revelling in the whole experience. I have often fantasised about my first "score" but never in my wildest dreams could I have ever imagined such a performance.

 

Chapter 10 – Wrap Up

I had no idea that Sarah and Margaret were bisexual. I wasn't even sure if Sally knew. I could hardly ask her about it since that would surely let the cat out of the bag as to our own Sexual Olympics. Much as I would have loved to brag about our lovemaking, I was afraid that if word got back to my parents they might try putting an end to our little tryst. I had a month of my agreement to go and when you are on a good time you don't want to do anything to rock the boat. So I walked around instead with a big cheesy grin on my face, allowing everyone to make his or her own assumptions as to what we had been up to.

As fantastic as it was to date Sarah and Margaret I could sense myself getting jealous over their freedom to wear whatever they wanted. Even when they wore what I might have once teased them about being menswear I often felt it was unfair that they could wear all manner of tops and pants and shoes that I could not. I also missed wearing make-up while men's jewellery just didn't have the same appeal. The best and the worst time for me was after we had made love. Lying amongst their panties and bras was almost too much. I had to admit I was missing wearing women's clothes.

When Margaret suggested we go out to a gay nightclub, it was the excuse I needed to resurrect Dorothy from out of the closet. All I'll say about the place that we went to was that it completely redefined my concept of womanhood. Some of the women there were so butch they would have given Mike Tyson a run for his money. Jeremy would surely have been in danger in a place like that.

Our relationship took on a new dimension from thereon. At first I continued to wear only men's clothing at home, while wearing whatever took my fancy when I went out with Sarah and Margaret. Sometimes Jeremy would greet them at the door while at other times it was Dorothy. It was so liberating being able to express my moods through my clothes irrespective of whether I felt soft and delicate or hard and tough. It was wonderful having Sarah and Margaret excited about seeing me irrespective of what I wore.

My mother, of course, was delighted to see Dorothy again and encouraged me in this regard. She even insisted on setting aside one day a month for us to do girlie things together so that we could continue to nurture our mother-daughter relationship. It was hard to resist her when we usually had such a good time together although I sometimes wished she'd be less of a mother and more of a girlfriend to me.

My father wasn't at all happy about all this, yet I was often enough in men's clothes for him to never be able to complain about my masculinity, especially as I continued to court not one but two gorgeous girlfriends. While he never gave me any sex talks as such, he somehow felt compelled to keep up my stock of condoms. I guessed that in his mind this not only kept Sarah and Margaret from getting pregnant but also served to remind me of my own gender. After my initial embarrassment, I started to regard it as being quite cute, as if it a scene out of the movie "American Pie".

My sister Sally faded out of the scene once she started dating Rex. The two of them seemed so preoccupied with each other that we hardly saw them at all. They got engaged last week. It all seems quite sudden to me but it's really none of my business. The only thing I'm wondering is whether she'll want me as a groomsman or a bridesmaid.

To say that my life has changed from this bet would be the understatement of the millennium. I am a million years away from the nerdy kid who was once fixated on a mini-skirted TV star. Not only have I my own sexy girlfriends to focus on but I can also dress as a Gena Davis lookalike anytime I want. I could never return to being exclusively a male, not if it meant having to give up all the pleasures I discovered while being Dorothy. How could I possibly go through life never again being able to wear a dress? How could I possibly force myself to walk past the cosmetic counters in all those department stores without stopping to have a closer look? How could I ever ignore all that glorious lingerie? The joy of my life is that I don't have to any more!

Yet how could I equally deny the appendage between my legs, my attraction to girls, and the need to be boisterous and physical from time to time? That's where my two girlfriends have come to my rescue. I thank god for them and for Gena Davis.

 

The End

© 2002

  

  

  

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