Things haven't been going so well for Dorothy. Not only has she suffered the humiliation of having to wear a pull-on vagina and a pair of breast forms at the hands of her sister and her two girlfriends but now even her body is turning against her. Today she is due to be taken shopping and she is so apprehensive about what that might bring that the poor girl has not slept at all well.

  

Wearing The Pants

by Catherine Rose

Chapter 6 – Shop Till You Drop

  

My Sunday clothes seemed pretty ordinary while laid out on the chair, but they took on a personality of their own once I put them on. My panties were white with lacing at the front and a small ribbon at the top. My bra was white as well with silky soft fabric, somewhat thicker than the others I had worn till then. I was told that it was called a T-shirt bra, one you could wear under a thin top without the seams or nipples showing through. What really made it different was that it had only one strap which went from side to side at the front crossing the back of my neck. I was told that it was for wearing under halter neck tops.

The top was so "little girlish" I was instantly mortified. I felt a surge of discomfort as something tried unsuccessfully to rise between my legs. The top was three-quarter length, light cotton material, and pastel blue in colour with navy edging around the neck and arms. But what made it so juvenile was the little heart on the front in rainbow colours of pink, orange, and yellow between my breasts.

I spent most of the day adjusting it, stretching it out at the front to conceal my bra, and pulling it up at the back when it slid down. It almost became instinctive and, remembering seeing the same actions acted out by girls, only served to make me feel even more girlish.

Even the white pair of pants did nothing to restore my masculinity. They didn't even cover my hips properly with their top button failing short of my navel by about an inch. There was 6 inches of bare midriff between the bottom edge of my halter neck top and the top of my pants.

Then came another shock – pink shoes! They were quite flash, ones I imagined would not look out of place with a glamorous gown. They had a strap across where the tops my toes joined my feet, one across the bridge of my foot that did up around my ankles, with a strap joining the two together across the top of my foot. To add further humiliation to the whole outfit, they had an even higher heel than the ones I'd worn the night before.

As I stood there in all my glory, no part of me felt male. I put on the gold-chained necklace with a "D" for Dorothy that fell perfectly among the neckline opening of my top. I had a pair of clip-on earrings that dangled any time I moved my head, a stainless steel bracelet that slid on over my wrist, even an anklet with a pale pink imitation pearl. By the time I had my make-up on, I actually felt more like Dorothy than whoever I might have been before.

My mother nearly died of shock when she saw me.

"Dorothy, you look so cute," she finally blurted out. "The little heart on your top, my God, your D for Dorothy pendant, the shoes and anklet … Oh how I wish you could have been my daughter from the start."

My embarrassment knew no bounds. Yet I felt strangely gratified. I couldn't remember ever pleasing my mother as much. I had always suspected that she liked Sally better than me, that I had been a disappointment to her. It was as if I had received her approval for the first time.

She rushed over and gave me a big a hug. I did all I could not to break into tears as I flopped into her arms.

"I never realised how precious you are to me," she whispered into my ear.

"Come on you two," Sally called out with more than a tinge of jealousy. "We need to be going, now. The shops are calling us."

My mother rushed off and returned quickly, pressing something into my hand.

"I've been saving this for a special day. I'm sorry for being so hard on you all these years. Make sure you buy yourself something really nice with it."

I nearly fainted as I looked at the two one-hundred-dollar bills in my hand. It seemed pointless to remind my mother that I was still her son, and not her daughter. To do so would have taken away from what had obviously been a special moment for us both. I slipped the money into my purse inside my handbag, draped it over my shoulder and exchanged one final kiss with my mother. My self-consciousness seemed to have disappeared for I walked out of the house with some pride knowing that I was loved by my mother after all.

My newly discovered bravery lasted as long as it took to get to the mall. I went numb from the moment I stepped into the first clothes shop. Being surrounded by racks and shelves of women's clothes was a nerve-racking experience. The girls started flipping through them without a second thought. I nearly died of embarrassment when the girls started holding up various items against me to see what they might look like on me.

"You must try this on, Dorothy," said Sarah holding up a pink top against me.

I was almost relieved to be ushered into a changing booth where I thought I might be able to hide.

Unfortunately, that proved to be only a temporary reprieve. Having to take off and put on a succession of women's tops and pants was as bad as anything. I hardly needed to be continually reminded that I had on a bra and panties. The bra, especially, gave me no end of trouble, having to be adjusted with every clothes change. Sometimes I even had to re-attach the straps differently to suit some garments. And, of course, the girls insisted I paraded every change of clothes for them, outside of the safety of the booth, so that they could see me properly.

And so began a fashion parade of clothes I could never have dreamt of wearing. Countless bras in different styles and colours; camisoles and petticoats with all sorts of lacing and trimmings; tops in fabrics like nothing I'd ever come across; I couldn't even believe all the different colours and cuts that pants came in. I was overwhelmed by the choices.

And then there were the shoe shops. They were even worse. They had no place to hide. I had to sit and try on shoes in front of whoever was in the shop at the time. Again, the variety was unbelievable. The styles, the colours, the different heal shapes and heights. It was an education. How could these things have existed all this time without me even noticing them?

Every store had something new to discover. I never realised the number of places that carried jewellery. Earrings, necklaces, bracelets … Not to mention accessories like handbags and scarves … Then there were the perfume counters … It just went on and on … If I learned anything from this experience it was how different shopping was for girls than it was for guys. Every shop seemed to be a "candy store" of countless delights. It was almost too much to bear. I don't know how women could ever deal with such over-stimulation.

And the girls that were behind my "Mystery Tour" were not about to let me to miss a single ride. Passing through the make-up section of a department store, they roped me into having a makeover. There I was sitting as this woman daubed stuff all over my face with an endless prattle about skin tones, and when to use different colours of eye shadows, and how best to apply mascara. It all just went in one ear and out the other. I sat in a daze pretending to be taking it all in while the girls watched on giving me as hard a time as they could.

"Oh, Dorothy, that shade really suits your complexion."

"That lipstick looks so divine. You must get it."

"My god, Dorothy, you look like a fashion model. I'm really envious."

But the most horrific thing occurred late afternoon. I was in a changing booth in yet another clothes shop when Margaret brought in a dress for me to try on. I just refused. This wasn't part of our arrangement at all. There was no way I was going to go along with this, or so I thought.

"Oh don't make so much fuss, Dorothy," Margaret chided me. "People will be wondering what's going on. The last thing you would want to do is to draw any attention to yourself. You'll probably get arrested and thrown in jail. I shudder to think what your cell mates might make of you."

I had to admit she had a point. It wasn't as if the girls had any reason to ease off on me since it was I that was deep in their territory. It was I that was in the compromising situation. I felt the trap tightening on me even further.

"If you think women should always wear dresses and skirts then the least you can do is find out first hand how that feels like," butted in Sally. "Besides, it's not as if we are expecting you to wear it, only to try it on."

"Come on, Dorothy, pined Sarah. "Be a sport. It's only a bit of harmless fun. When else will you ever get such an opportunity?"

It felt more like torture than an opportunity but I didn't have much choice. The girls had once again got the better of me. And once I stepped out in my first dress, they pressed home their advantage. They soon had me modelling more dresses than pants. They even had me twirl around in some outfits so that the skirts flounced around with me.

"Careful, Dorothy," laughed Sally. "We nearly saw your panties that time."

But if I thought my situation had become as bad as it could get, nothing could have prepared me for what happened in one store. I was modelling a black shift mini-dress for the girls outside the changing booth when I suddenly heard an unfamiliar voice from behind.

"That looks fantastic on you." I wish I could get away with wearing something like that."

I nearly died as I turned around to find a middle-aged lady standing behind me, apparently the manager of the store.

"Is it for a school dance?" she inquired. "Try this chain with it around your waist. The dress is on sale for only $75 today but you can have the chain with it for free."

"She'll take it," said Margaret. "Go get your purse, Dorothy."

"What are you doing?" I said through clenched teeth on the way back to the booth.

"Don't worry," said Margaret reassuringly. "You can bring it back later for a refund. I just wanted to get rid of that lady before she cottoned on to what we were doing. Get changed quickly now and pay the nice lady so we can get out of here. Meet you outside."

I slipped out of the dress and back into my own clothes (??). I couldn't believe that I could feel relieved to be wearing them again. I couldn't believe I was walking up to the counter with a dress draped over my arm. I couldn't believe I was reaching into my handbag for my purse. It seemed like an eternity till I was served. The shop assistant seemed to take ages folding the dress and putting it in a carry-bag. I then had to wait for the change and the receipt before I could finally walk out the door, my handbag draped from one shoulder with my other hand holding what was obviously a bag from a woman's clothing shop.

"That was the most embarrassing thing I've ever been through," I said under my breath as I caught up with the girls outside. But they scarcely heard a word I said as they giggled and laughed away uncontrollably at my expense.

"Never mind, Dorothy," said Sarah. "Let's all go to the café for some coffee and cake."

"Yeah! Let's celebrate Dorothy buying her first dress," said Sally. "I can't wait to show mum what you have chosen for yourself with the money she gave you."

It was a relief to sit down and relax for a while. I still felt totally humiliated. All I could do was blindly follow the girls around for the rest of the day like a sheep. I even started flicking through clothes racks myself. At one stage, while they were in change booths trying on clothes themselves, I found myself walking in with some items that I had picked out.

As I looked at myself in the mirror wearing an asymmetric pink skirt, a lilac cami top, and a blue nylon cardigan with ¾ folded up sleeves, I suddenly realised that I had ventured into unfamiliar territory once again. Not only had I chosen these items myself, but I also felt amazingly pleased with my choice. I knew I was in trouble. I wanted to take it all off before any of the girls sprung me, but it was too late.

"Wow!" gasped Sarah peering into my booth. "Where did you find those? Those clothes look sensational on you. Did you choose them yourself?"

"Let me see, let me see," chimed Margaret and Sally.

Before I knew what was happening, I was standing in the middle of the shop with all eyes on me.

"I don't know how much all that costs," exclaimed Margaret, "but you have got to get it all. It suits you so well."

"I'm jealous, Dorothy," said Sarah. You have got to help me find something as nice as that."

The girls never allowed me to take off those clothes. They simply pulled off the tags and gave them directly to the nearby attendant. This time, it was my old clothes I carried to the counter to be packed away in yet another shopping bag as I reached into my handbag for my purse. The events of the day and of the day before must have taken me beyond all embarrassment and humiliation. As I walked out of the shop in my new outfit I had to admit that I felt quite pleased with myself.

We continued looking around the shops till closing time, even though I had no more money to spend. I felt a lot more relaxed about things than I had before. After all, no one had suspected my true identity in the slightest. I felt as if I had infiltrated into another world. In this world I could just about get away with wearing anything. I was starting to enjoy the charade as if it was a joke I was playing on everyone else in the world.

But the joke was about to turn on me as soon as we got home.

"Mum, come and look at what Dorothy has bought," yelled Sally as soon as she'd opened the door.

As you can image what followed was even more sighs of disbelief from my mother and even more compliments from all concern. My mother was almost beside herself. She even noticed my makeover.

"Oh, Dorothy," you look so beautiful."

"Wait till you see what else Dorothy has bought for herself," teased Sally.

I reached inside the bag for the dress, "No, No! You have to put it on first," insisted the girls.

And with that I was shuffled upstairs. I slipped into my dress and apprehensively made my entrance into the lounge room.

"Dorothy, you look sensational," my mother gasped. "That dress really suits you. Oh how I wish you could stay my daughter. I'm so glad we still have a whole week ahead. Perhaps, on Wednesday when I get off at lunchtime, you could meet me in town and we can go shopping together."

I couldn't believe what had transpired in the space of only 48 hours. While my embarrassment was undeniable, I detected an element of satisfaction as well. Sitting around with my silky smooth legs visible underneath my dress for the rest of the night with mum almost beside herself the whole time was something I could never have imagined in my wildest dreams. Not to mention my new haircut, my makeover, my new body and my new name. My former self was becoming a distant memory.

That night I dreamt I had been turned into a girl by a fairy godmother. I had to get home before midnight or the spell would become permanent. But I was enjoying myself so much I completely lost track of time. As the clock began to strike 12, I turned to leave the room in a panic, but my high heels prevented me from reaching anything more than a pathetic little trot. I wasn't going to make it. Then suddenly I tripped on the steps outside and tumbled onto the pavement. As the clock continued to strike, I lay there unconscious. A buzzer went off and I awoke in a cold sweat. It was my alarm clock sounding off. I immediately reached down between my legs to find my penis still there, albeit still firmly tucked away. Thank God it was only a dream.

  

Chapter 7 – A Change of Heart

I didn't need to be shown what to wear Monday morning. It was obvious that it was going to be the outfit I had chosen the day before. I quite enjoyed putting it on, partly because I had coordinated it myself, and partly because I felt wonderful in it.

There was no one else home. They had all left for work. So I was able to revel in my new clothes without fear of being found out. I put my face through the cleansing routine I was shown during my makeover the day before. I took my time putting on my make-up trying to savour the moment as much as possible. I even touched up my nail polish.

At times a little voice of self-doubt would try to bring me to my senses:

"You are a boy! You shouldn't be doing this. What is wrong with you?"

Almost as quickly another voice would come to re-assure me:

"This is only a game. You might as well enjoy it as much as you can, knowing that on Saturday you can return to being a boy and dating the women of your dreams."

The day sped past quite quickly. I flicked through a pile of women's magazines I found in a cupboard. To be truthful, I always knew they were there. I frequently looked through them when I was on my own to jerk off to the women in the pictures. This time, however, there would be no masturbation. I realised I was more interested in the clothes than the girls themselves. I chuckled when I noticed that one of the model's names was Dorothy and started imagining what life might have been like for me if I was able to wear such beautiful outfits and be paid for the pleasure.

I even decided to go outside for a walk. As I strolled along part of the way where not 2 days earlier I had rushed home in embarrassment for the hairdressers, I realised how much I'd changed in such a short time. Today I walked quite proudly in my outfit. I wasn't at all embarrassed that other people might see me. In fact, I welcomed any attention as it affirmed me as I was.

I made sure I was home before my family returned from work. It was a quiet family night at home with Sally and Margaret not even coming over. Dad seemed more resigned to my situation, even calling me Dorothy a couple of times. Mum, on the other hand couldn't seem to leave me alone. So much so that I could swear Sally was getting jealous.

Something even weirder happened the next day. Sally was running late for work and the girls had forgotten to discuss their "tactics" the night before. She told me that, other than my underwear and shoes, I could wear whatever clothes I wanted, including my own. I had sensed they might have been losing interest in our bet and that I might be gaining the ascendancy but yet another surprise was awaiting me.

As I walked around the house in my own jeans and denim shirt, the barometer between my legs clearly showed that something was not quite right. I suddenly realised that while wearing women's clothes I had felt like an actor playing the role of a woman. In wearing my own clothes over the top of my women's underwear, I felt as if I was hiding the fact that I had become a woman. I didn't know what to do with myself.

Seeing my make-up items laid out on my dressing table made things even worse. I had an unmistakable urge to do myself up. I realised makeup had been a bit of a bother for me over the preceding week, continuously having to touch it up throughout the day, yet I hadn't expected to suddenly feel undressed without it.

The same thing occurred around jewellery. My hands seemed to be crying out for some bangles and my neck felt naked without a necklace. I even missed the dangling of earrings from my ears. What was happening to me?

I decided that this must have been caused by the fact that I had a mixture of men's and women's clothes on and that I'd be okay if I just wore all of one or the other. Since I couldn't escape my bet for a couple more days, the choice of which clothes to take off and which to put on was virtually made for me. Inexplicably, I slipped on the black dress I had bought on the weekend. Before I had any time to think about it, I had done my make-up, put on my jewellery, and went downstairs to relax into an easy chair in the lounge room.

As I sat cross-legged, I suddenly started to wonder why I had chosen a dress. I had my choice of wearing any clothes I wanted and I had chosen a dress? I couldn't believe it. What was wrong with me? I quickly jumped up to get changed again. But as I reached the top of the stairs, instead of opening the door on the right into my room, I turned left into Sally's.

For the next 2-3 hours, I spent trying on every dress and skirt I could find. After going through all of Sally's clothes, I went in and started with my mother's. I don't know what got into me. I'd been trying so hard not to be affected by my clothes. I'd been trying so hard to shield myself from all the femininity I'd been subjected to. And now it seemed to have taken me over completely. Yet it felt so nice that I couldn't get enough of it.

I wore all the things normally unavailable to me. I raided Sally and mum's jewellery boxes, wishing my ears were pierced so I try on all their earrings as well. I raided their make-up tables, trying on different shades of lipstick and eye shadow. I even rifled their underwear drawers. I couldn't resist trying on some pantyhose. If I had thought that the softness of my bare legs rubbing against one another in a dress felt wonderful, encasing them in pantyhose was simply divine. I was amazed what they did to me.

It was all an exhilarating experience. It was like going shopping with the girls only better. Because I had no one looking over my shoulder I felt free to choose whatever interested me. Most importantly I could allow myself to enjoy it!

I felt so wonderfully feminine in all the clothes. All the fabrics felt so nice. Different styles, different colours, different cuts were suddenly all available to me. I found myself floating around the house in a world of feelings I could never even have dreamt of.

And then it was time to put it all back. People would soon be coming home from work. My joy was replaced by fear, fear I might get caught, fear I might not put everything back in the right place, fear that no one found out that I had been enjoying myself wearing women's clothes.

As I sat in the lounge-room ready for everyone to start arriving from work, I felt cheated that such pleasures would be denied me just because I was a guy. I felt cheated that I had to act tough all the time. Why couldn't I feel soft and feminine at times? If it was okay that women wear jeans whenever they liked, why couldn't I sometimes wear dresses if that was how I felt? It didn't seem fair.

"You don't look very happy, Dorothy," Sally said as she saw me sitting glumly on the sofa in my jeans and denim shirt.

"What's wrong, honey?" Asked mum as she walked in behind her.

"It feels weird having to wear my own clothes over this girlie stuff," I lamented.

"Well, that's easily fixed," teased Sally. "Why don't you just put on that new dress you bought?"

"I can't do that!"

"Of course you can, dear," said mother coming over to me. "You looked so lovely in it the other day. In another couple of days I won't be able to see you this way ever again. Please put it on for me one last time."

With her pleading eyes looking into mine and her hand holding my hand, I felt myself lifted up from the sofa and headed upstairs. I couldn't believe that even my own mother would be encouraging me to be a girl. At least I now had the excuse I needed to get out of my own clothes. After all, she had paid for that dress. The least I could do was to wear it for her when she asked.

I felt both embarrassed and oddly contented as I made my why back downstairs in full regalia again. Sarah and Margaret could not believe their eyes when they dropped by after dinner. They seemed nearly as pleased as my mum did. The only one that seemed to not be enjoying herself was Sally. And who could blame her? Not only had I taken her power over me away from her but I had also become the centre of attention among her two closest friends. And then tomorrow while she had to go to work I would be shopping with our mum, bonding together as mother and daughter.

 

To Be Continued …

© 2002

  

  

  

*********************************************
© 2003 by Catherine Rose. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.