Jeremy has been turned into Dorothy by his sister, Sally, and her "to-die-for" girlfriends, Margaret and Sarah. It's on account of a bet about women wearing pants which Jeremy (or is it Dorothy) is confident of winning. But perhaps it is too early for anyone to be counting his or her chickens considering the bet officially only starts today.

  

Wearing The Pants

by Catherine Rose

Chapter 3 – A New Day Dawns

  

I couldn't believe it was only 6 o'clock when Sally woke me up. My 'Dutch Courage' from the night before had all evaporated to be replaced by a feeling of foreboding.

"Come on, sleepyhead," Sally said rousing me. "You've got lots to do to get ready."

I might have hoped that it all had just been a bad dream that would end upon waking. But my nail polish and the softness of my body clearly showed the reality of my nightmare. But the most frightening thing was that my penis was still tucked away in its little pouch behind my vagina. I was amazed that it had not slipped an inch during the night. In fact, it almost seemed as if it had adapted itself to its new position.

Showering only further reminded me of my hairlessness. My body seemed to be tingling all over, almost pleasurably. I still had to shave my face, but my embarrassment started all over again as soon as I started getting dressed.

It was quite unnerving dressing in women's clothes. The girls were not there to bully me along this time so it felt as if I was doing it out of my own choice. Neither were they there to help me as I struggled for ages with the clips at the back of my bra. It was almost by accident that I got them done up at all. By the time I had put on my panties, the word 'Dorothy' was echoing in my mind again. A cosy sweater, pants that zipped up on the wrong side, platform sandals that made me conscious of my every step … As I made my way down to breakfast, I couldn't help but feel as if this time it had been I that turned myself into a girl.

Mum was in the kitchen, fussing over me like a mother hen. Sally was there to tease me. Dad was conspicuous by his absence. If I ever had a name other than 'Dorothy' nobody was using it this morning. I couldn't wait to escape back upstairs to my room, even if it was only to put on my make-up and ready myself to go out. At least I could hide for a few minutes longer.

But Sally was soon banging on my door and leading me not just downstairs but outside. With dainty little steps, I moved my legs as fast as they would go. I jumped into Margaret's car and we were off …off onto the next stage of my nightmare.

Thankfully, the hairdressers where Margaret worked, was only 10 minutes drive from my parents' house. I was soon scampering from the car up to the front door. Margaret seemed to be fiddling about with the keys to the shop. She dropped them. She picked them up and fiddled about with them some more. It seemed like ages before I was able to slide into the safety of the shop.

We were there an hour before opening time so that Margaret could do my hair before the owner of the shop came in. At first, it felt like any other hair cut. A shampoo, a cut, before Margaret returned me to the basin to re-shampoo my hair. Then in the middle of it all, she said she had to go out the back to get things ready for her first customers.

She seemed to be gone for ages. All I could do was to sit there with my head resting back in the basin, staring across at the front door worried that someone might come in. When she finally returned, there was not so much as an explanation let alone any apology. But as she rinsed off my hair one last time and returned me to my seat to blow dry and style it, I suddenly realised what was going on.

"You, bitch!" I screamed as I noticed in the mirror that my previously brown hair had somehow turned blonde.

"Don't worry," she replied. "We can always return it to your previous colour afterwards. Then again, you might want to keep it as it is. Men dye their hair as well, you know."

As I examined my new hairstyle, I was quite sure that I would not want to keep it as it was. It might have been short like a men's hair cut, some men might have even dyed it like mine, but the way it was cut and styled had a definite womanly look about it. I scarcely looked like a male even to myself. As Margaret finished off with some hair spray, a tear slid down from my left eye as I reflected on what I'd become.

"Dorothy, my love," Margaret said proudly. "What do you think of that?"

"I hate it. You are a witch. Look at what have you done to me."

"I guess I'll have to take that as a compliment. I've done you a favour, Dorothy. At least no one will bother you on your way home."

"What do you mean?"

"Well you can't stay here forever, and I can't leave work just to take you home. I hope you brought some bus money."

"You mean I have to go home like this on my own?" I stammered.

"Quick! That's the owner driving up. You must go out the back."

"No way," I protested. "You can't send me out looking like this."

But even before the words had left my lips, my handbag had been thrust into my hands and I was shuffled out the back door.

"If you so much as even try to come inside, I swear I'll just deny any knowledge of you and call the police," were the last words I heard as the door slammed shut behind me.

I stood there in stunned silence for a full minute before I realised I had better scamper. But where do I go? Home, of course. But how do I get there? Buses go every 10 minutes, or it was about a half an hour walk.

I didn't have time to deal with the shock of my predicament. I just wanted to disappear. I didn't fancy myself waiting at the bus stop, as this would only invite attention. Then, I would have to sit on the bus in full view of whoever else was on it. I started off in a brisk walk home, figuring that a 'moving target' was better than a 'sitting duck'.

I looked down towards the ground each time anyone approached from the other direction. No one seemed to bother much about me until two guys whistled at me. I kept walking on ahead in disbelief, hoping to God that they hadn't started following me. Thankfully, they soon disappeared and I breathed a big sigh of relief as I walked into the safety of the front door of my home.

"Is that you, Dorothy?" asked my mother coming out from the kitchen. "Wow, you look great! I love the colour. Did you choose it yourself?"

"No," I replied indignantly, "I did not!"

"I was wondering how you would be getting home. Did Margaret drop you back?"

"No, she didn't," I snapped again. "I had to walk home."

"At least you've had some practice passing off as a woman for when we go out tonight," laughed Sally from behind me.

"No way!" I exclaimed spinning around.

"Why, of course, you will," teased Sally. "Part of this bet is being able to do everything that us girls do while wearing only men's clothes. Besides, I've just come back from the shop with the photos from last night. You might like to look at them before you start complaining too much."

Noticing that the negatives had been removed from the pouch, I flicked through the photos in utter horror. It was one thing to see myself in the mirror but it was something entirely different to see myself as others might see me. I was done for. I could feel the noose around my neck getting even tighter. Why had I ever agreed to this bet?

  

Chapter 4 – Life From A New Perspective

I escaped into my room hoping that I could forget about my predicament by staying out of everybody's way. Fat chance of that! I tried playing my Playstation games but my long fingernails made this near impossible. Then there was the matter of the toilet. It was bad enough having to pull down my pants and panties just to pee. Having to sit there and listen to the acoustics of the constant steady trickle of water splashing directly into the bowl reminded me of waiting outside the door for my mother or sister to finish their business. It was horrifying to think that this same sound was now emanating from me.

Even sitting down to read caused me grief. I was so self-conscious about my new vagina that I felt I needed to keep my legs crossed just to keep everything properly tucked away. And of course I could always feel my penis squashed in underneath me. I found that by tightening and releasing my thighs my penis slid backwards and forwards between them getting harder and harder. I raced for the toilet as I recognised the point of no return. I quickly slipped off my pants and panties and squatted over the bowl. As I wiped my 'undercarriage', I shuddered as I realised I was now even cumming as a girl.

My bra by now had become quite uncomfortable. The underwire felt as if it was about to cut me in half, while the little clips that adjust the lengths of the straps were rubbing against the top of my chest. In addition the day was warming up and I was starting to overheat. So I was most relieved when Sarah turned up at my door with a change of clothes.

"Here, you might feel cooler wearing these," she said handing me pink denim shorts and a red shoe-string top. "You can take off your bra if you like since the top has a shelf-bra built into it."

I didn't need a second invitation, although I could have done with some help removing my bra. But Sally left as abruptly as she arrived, leaving me to once again get dressed on my own as if this whole thing was my idea.

Much as I was relieved to cool down, I soon realised what Sally had meant by the top. It had an inner lining with an elasticised edge that hugged me under my breasts. The outer lining gathered up everything underneath it to make the most of whatever breasts I had. Not even my shorts could give me the respite I might have hoped for. Apart from being pink, any time my legs brushed against one another (like when I sat cross-legged) I was even more aware of their silky smoothness.

I scarcely had time to get accustomed to my new clothes when my mother came knocking at my door.

"Dorothy, dear," she pleaded on opening the door. "Could you help me with lunch, please. It's such a beautiful day I thought we might have it outside on the patio."

It wasn't as if I could really refuse her.

"You look really nice in that top, dear," she said matter-of-factly as I got up to follow her.

"Thanks, mum," I replied shyly, going as red as my top.

Helping out with lunch amounted to little more than laying out of the plates and cutlery and the cold meats and salads that mum had already prepared. Opening and serving a tin of beetroot was as complicated as it got for me. Mum seemed really easygoing, explaining that my long nails would make it hard for me in the kitchen.

"Ladies with manicured nails usually do little more than stack dishwashers," she said. "But I thought you needed to experience some of the difficulty first hand."

"Don't worry, mum," I reassured her. "My nails are complicating everything. I nearly poked my eye out this morning washing my face."

I relaxed a bit more around my mother's casualness. I was grateful to her for treating me with such nonchalance. She seemed to have the same calming effect on Sally and to a lesser extent even on dad. I started enjoying myself out in the sun until Sarah and Margaret, who worked only half days on Saturday, dropped around in the early afternoon.

There was great hilarity as Sarah appeared in a similar outfit to mine but in different colours.

"Gee, Dorothy," Sarah remarked. "I hope you remembered your sun block."

Sure enough, when I looked closely at my shoulders, I noticed strap lines already starting to show.

"Don't worry about it, Dorothy," said Margaret. "It's too late to do anything now. Let's go upstairs, I've got a surprise for you."

I was more than a little apprehensive about Margaret's little surprises after the vagina she had furnished me with the night before. However, I was also anxious to get out of the sun to avoid any more branding so I dutifully followed her and the other girls.

Once in Sally's room, Margaret pulled off my top without another word and blindfolded me like the night before. I could hear stifled giggling and gasping in the background as Margaret applied what felt like sun block on my chest, at least until she pressed something hard against it that seemed to tug my skin downward. It wasn't till she repeated this on the other side that I cottoned onto what was going on.

"What are you doing?" I screamed as I ripped off my blindfold. Then, "Oh my god!" as I looked down at the two well-formed breasts that were hanging from my chest.

"Nice joke," I said hopefully. "Now how do I get them off?"

"You admit you were wrong all along," taunted Sally.

"Or you just wait till the week is up like a good little girl," offered Margaret.

"You can hardly call her little any more," complained Sarah. "She's bigger than me."

It was useless arguing with them. It hadn't done me any good till then and they weren't about to give away any ground now. These falsies were apparently called Breast Forms and were used by, among others, women who have had mastectomies. This explained how authentic they looked. Margaret soon demonstrated (on me) how with the careful use of makeup around where they bordered the skin, they could be made to look almost be undetectable.

"Why don't you remove your panties, Dorothy, so we can get a proper picture of your new body?" joked Margaret.

"No way," I screamed, slipping my top back on quickly. Unfortunately, it did very little to conceal my new pair of 36Cs. Not only was I sporting a fabulous cleavage now but the outlines of my teats were clearly visible through my top.

"Don't be so modest," exclaimed Sally as I instinctively put my hands on opposite shoulders to cover myself up. "After all, wasn't it you that said that 'If you got it, then you should flaunt it'?"

She had me there. I felt totally defeated. I should have apologised there and then and called the whole thing off. I had learnt my lesson well and truly. I felt sorry for myself and for how I'd been towards her. But the words just couldn't pass my lips and they would have been too late anyway, as I doubted if the girls would have let me off the hook now they had got me this far. All I could do was to bite my tongue and accept my medicine. Like it or not I now had to get accustomed to a new pair of breasts.

I found I had to stand straighter than before to compensate for the sacks that clung to my chest. This only seemed to push them further forward. The slightest movement on my part caused them to bounce around in all different directions as if they had minds of their own. I wished I could put my bra back on to round them up but it probably wouldn't fit me now.

When Sarah and Margaret finally left, Sally suggested I start getting ready for tonight by relaxing with a nice hot bath. She ran the water for me, mixing in special oils and soaps that would 'revitalise my aching muscles'. I was relieved to be able to hide my breasts under the soapy suds. I was relieved to have managed to keep them motionless for a while. I was relieved to be able to have some timeout on my own. As I lay there I started to cry for first time since I could remember.

"My god," I thought. "I'm even blubbering like a girl."

Every now and again I'd sit up straight and pull on the breasts hoping that they might have been loosened by the hot water, but to no avail.

And then I started doing something inexplicable. I started sponging them down with a face cloth. I couldn't feel anything of course except through my hands yet I felt strangely aroused. I was even more so as I slowly moved down to my vagina beneath which I could feel my penis. As I orgasmed from what might have seemed to be vaginal stimulation, I wondered if I hadn't struck rock bottom. I fell asleep thinking - "Surely it can't get any worse than this."

   

Chapter 5 – Girls' Night Out

My peace was suddenly disturbed by a loud scream as the bathroom door opened, then by a series of "Oh my gods" as my father beat a hasty retreat down the hallway. I sat frozen in the tub, not daring to move even an eyelash until Sarah came with a towel. She tried hard to contain her laughter as she showed me how pat myself dry and how to wrap myself in the towel as women do. I realised I must have been dozing for quite a while as Sally was all dressed up for our night out. So were Sarah and Margaret who turned up just as we were making our way into Sally's room.

As I removed my towel to put on the bra and panties Sally had passed to me, the flash of Margaret's camera again blinded me. This time I had no fight left in me. I meekly slipped on my black lace panties and did my best with the matching bra, which seemed even more complicated now that I had something needing to be positioned inside. It was so sheer that it left little to the imagination. Nevertheless, I appreciated for the first time how well a bra did its job of supporting breasts. All the while the camera kept flashing.

Next I was handed a pair of white flared pants. Again they were really tight around my waist, if you could say they reached my waist at all. My shoes were a pair of sandals with a thick strap across my toes and one across the bridge of my foot atop a 4-inch heel. I didn't need to worry about sliding out of them. The heels were so high my toe simply slid into the front of the shoe while the rest of my foot followed behind. When I walked, I felt like Peggy Bundy from the 'Married With Children' TV Show.

Fortunately, I had learned to take short deliberate steps from wearing the platform shoes over the preceding 24 hours. This helped me to get accustomed to walking in 4-inch heels a lot quicker otherwise I'm not sure I could have even stood up in them. But I wasn't prepared for the clippity-clop noise they made when I walked around in them or how quickly my toes, ankles and calves would get sore from wearing them.

But the coup de grace was yet to come. It was a sheer black blouse with scalloped edging at the bottom and around its elbow length sleeves. It hug me so tight that it seemed to accentuate my breasts even more. What was worse was that it was so transparent that you could see my breasts through both it and my bra! But what threw me most was that the only word I could think to describe it was - gorgeous! I could feel myself starting to enjoy my new clothes! At that moment I knew I had gone in way over my head.

"I can't wear this, " I exclaimed. "I'll get arrested … if I don't get attacked first."

"If it will make you feel more comfortable, you can put this on underneath," replied Sally handing me a black camisole.

I was so unsettled by the blouse that I slipped on the camisole without hesitation. It was only then that I noticed its silky softness and its intricate lacing. I quickly pulled the blouse back on, hoping to conceal the camisole. It was hopeless. I now looked even more alluring than before. I stood mesmerised by my own reflection in the mirror. Any girl wearing what I had on would have got a rise out of me, yet I could never have imagined that I could get so turned on by myself. Fortunately, the pull-on vagina, my cute little panties, and the tight pants I was wearing more than adequately kept my 'arousal' concealed. Only my embarrassment showed.

"Oh, don't be so shy, Dorothy," cooed Margaret ever so sweetly. "You look really sexy! And you shouldn't have to worry about any unwanted attention from guys where we're taking you tonight."

You can guess what followed. I received another lesson in makeup, this time with more striking colours for the evening. The girls even had me spray on some perfume. There was no escaping its hypnotic scent, which seemed to permeate every cell of my being. Any remaining resistance to the waves of femininity that had swamped me over the preceding 24 hours seemed to drain from me altogether. As I wiggled my way to the car onto more uncertainty with the girls, it felt as if I had changed sex entirely, inside and out.

We parked outside a pub and headed inside. I shuddered as I noticed a poster announcing it was 'Ladies Night'. Before I realised what was going on we were sitting ourselves down at a table ordering drinks. I could not believe that no one had even challenged my gender let alone my age. Having everyone accept me as a young woman had me resigning to the same myself. That is, until the lights were dimmed and floorshow started.

I turned my chair towards the centre of the room and shivered as male dancers started strutting their stuff. I went red with embarrassment as they stripped down to their G-strings. Music pounded as women around me behaved like sex-crazed animals. I had seen nothing like it. If it had been men behaving in that way towards women strippers, they would have surely been labelled as some sort of perverts. Yet women seemed to be able to do so with immunity.

I nearly died when one of the guys, sensing my discomfort, came up and straddled my lap. Holding my shoulders and arching himself in towards me, he started gyrating his hips. Everyone erupted into screams and howls. The guy then gently sat on top of me, grabbed my hand and had me touch a bulge in his G-string. I yanked my hand back instantaneously and heard the room explode into laughter.

To make matters worse the reaction around the room had been so uproarious that in succeeding dances different guys seemed to seek me out from the crowd. One even pulled me up to dance along with him on the stage. I don't know what became of me but I found myself willingly following along. At one stage, we arched our hips towards one another and I felt his penis rubbing against me.

I never heard the end of it from Sally, Margaret and Sarah.

"I bet you really would have liked to have had that guy inside your panties, Dorothy."

"He got so close to you we'll have to give you a pregnancy test when we get home."

"I'm so jealous, Dorothy. Those guys fancied you so much, they didn't even notice me."

I wished the world had opened up beneath me and mercifully swallowed me away. But, no. I had to put up with it all the way home and then again in front of my mother.

"Hey, mum" yelled Sally as soon as we walked in the front door. "I think Dorothy might be ready for a talk about 'the birds and the bees'."

"You should have seen what a great dancer your new daughter is."

"Yeah, we had to beat the guys off her with a stick."

I was still in a state of shock when I finally managed to escape into bed. Not even my pretty pink shortie jarmies could relax me. I was ashamed at how my body had behaved. Even it had betrayed me. I lay trembling inside with the image of those naked guys etched in my mind with the feeling of hardness behind my vagina wondering what had become of me.

Every time things had appeared to hit a new high in humiliation, they just seemed to get worse. I could hardly sleep at all from the apprehension of what the following day might bring.

 

To Be Continued

ฉ 2002

  

  

  

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ฉ 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.