It's funny how you can sometimes see a set-up coming and not be able to avoid it. And once it's been sprung how quickly it can become a one-way slide going faster and faster downward into a world from which there is no escape. The irony of it was that the very thing I was trying to defend, my male ego, would have to be subjected to a world of femininity just to prove my point. I don't even know if I could call it "Forced Feminisation" since I went along with each step even if at times it did seem that I had little choice. I could normally handle my elder sister but her "drop-dead-gorgeous" girlfriends were another matter. Then when my mother got involved even my own feelings were hard to understand. You'd think that collecting on my bet would have settled things once and for all yet I'm not really sure who was the real winner. You might have to judge for yourself.

 

Wearing The Pants

by Catherine Rose

Chapter 1 – The Sting

 

I thought it would be a safe bet to make. I may have been pressured into it, but I thought it would have been an easy one to win. And the prize? Well, that was worth the risk in itself.

It all started innocently enough while I was watching 'The Gena Davis Show' on TV. I thought Gena was a real fox and the way she dressed would have made women half her age drool with envy.

My sister must have been one of these for she always gave me a hard time whenever I watched the show. According to her, Gena had turned herself from the serious actress (ex-Thelma and Louise) to that of a bimbo. According to her, she had insulted all women by starring in such a "pointless show".

"If you've got it, then flaunt it," I'd say.

"At least she's not afraid of looking like a woman," I flippantly added one day," not like someone I know." I could tell immediately that I had scored a 'direct hit'.

"A woman can be a woman without having to wear dresses that barely reach beyond her navel," she screeched back at me.

"Come on, Sally, just look at you," I pressed home my advantage. " You're wearing pants, a sweater, sandals … and that's just what you wore to work today. Half the time you could be wearing my clothes and no one would even notice."

"How dare you! I spend more time and money on my clothes in a week than you would on yours in a year. Just because I don't dress like a 'dolly-bird' doesn't make me any less of a woman."

"Well, you shouldn't make fun of those who aren't afraid of showing their femininity."

"There's more to femininity than wearing short dresses."

"Like you would know…!"

And so it went on. I might as well have turned the TV off. It wasn't as if I could watch it with this going on. The truth was that I couldn't have cared what my sister wore. I just wanted to enjoy my show without having it spoilt by her negativity.

I was 17 years old, on holidays from school. My sister was 2 years my senior and acted like our birth order gave her some sort of divine superiority. We often erupted into these types of sparring matches. Usually they blew over as quickly as they started. Not this time, though. Sally was not about to drop this one in a hurry. What I didn't realise was the lengths she was prepared to fight it out.

The next week, while The Gena Davis Show was on, Sally was there with reinforcements in the way of her two girlfriends, Margaret and Sarah. Their very presence would have been enough to distract me from the TV but I pretended not to be interested in them.

The same argument was basically repeated from the week before, only this time there was three of them to one of me. I could 'smell a rat' but I couldn't tell what they were up to. Not until Sally started their 'offensive'.

"If you're so sure that there can be no femininity in wearing pants, then you won't mind wearing women's pants for a week to prove your point."

"Yeah!" added Margaret. "If you think our clothes are so much like yours then you won't mind wearing them instead of your own."

"Now, wait a minute," I said as I started to realise what they were up to. "If you think you are going to trick me into letting you dress me up like a girl, you've got another thing coming. I wasn't born yesterday, you know."

"Oh, no," Sally chipped in. "We don't want to dress you in women's clothes, only men's ones. You know, pants, t-shirts, sandals … No dresses or skirts, only men's clothes. The type that, according to you, real women wouldn't wear."

"No way! I'm not playing your little game."

"Then you admit that you were wrong and that we are right, " Sally pressed on.

I felt the noose tightening around my throat, If I let that one go I would never be able to face them again. Sally didn't matter, since was my sister. But the other two … they were another story. I had fantasised about them for as long as I could remember. They were a real turn-on irrespective of what they wore.

"All I'm saying is that you don't have to feel intimidated by women who aren't afraid to dress like women."

"Intimidated, eh?" Margaret said as she snuggled up to me. Running her hand through my hair she gently whispered into my ear, "It seems to me that you are the one that is intimidated. Too scared to back up your wild opinions with any action, too scared because you know you are wrong. I dare you to wear our tops and pants for a week. If you can do that, not only will I dress up as a bimbo for you, but I'll also go out on a date with you so you can show me off to your chauvinistic friends."

"Me, too" said Sarah as she snuggled up to me from the other side.

Now they really had my attention. Both of these girls were real 'babes'. To even think that I could go out on a date with either of them was almost beyond my wildest dreams. But having to wear women's clothes to do it was drastic stuff by anyone's standards.

"Perhaps he doesn't want to go on a date with us. Perhaps he's gay!" whispered Margaret in my ear.

"I am not!" I protested.

"I don't know. You seem pretty whimpy to me".

"Okay! I'll do it. But it's only for one week, its only pants and tops, and you'll have to date me for a month afterwards," I said going back on the offensive.

"A month? Okay, then! But if you're going to force us to date you for that long, then you have to let us dress you in whatever we choose, excepting for dresses or skirts, of course."

"Hold on," I jumped up in panic. "It was only supposed to be tops and pants."

"Let's get this right," Sally interrupted. " You were the one that said that women can't be women while wearing pants. So it seems only fair that you allow us the chance to prove to you that there is more to femininity than wearing dresses."

"And it was you that raised the stakes to a month, " added Margaret. "It seems you are all big and mighty when it comes to opening your fat mouth but all whimpy when it comes to backing it up with action. The only question you have to answer is whether you are prepared to prove your point as we've discussed or just admit you were wrong and we'll forget all about it. Which is it?"

"You're on!" I was at boiling point by now and there was no going back. I was going to make them eat 'humble pie'. What did I have to lose? Sure, I might have to wear women's clothes for a while but it wasn't as if I had to wear dresses or anything. I was at home on holidays anyway. It wasn't as if anyone had to know about it. How bad could it be? And best of all I would probably be seeing Margaret and Sarah every day and I could date them for a month afterwards. Who knows what this all might lead to?

Barely had those fateful words left my lips when Sarah and Margaret each grabbed one of my hands and started leading me upstairs. I had that "Oh, my God! What have I got myself into?" feeling as Sally opened the door to her bedroom. Laid out on Sally's bed were some clothes, the same ones that she had worn the week before when this whole thing first started. I suddenly realised just how badly I had been set up. But it was too late to do anything about it by then…

  

Chapter 2 – The Nightmare Begins

Margaret and Sarah immediately started removing all my clothes and I was soon standing totally naked. Not for long, though. Sally handed over some clothes from the bed and before I could blink I was looking down at myself wearing a set of what was undoubtedly women's panties with a matching bra. They were purple with a floral print of red and white flowers. I don't know what embarrassed me more, how the bra had turned what had been a muscular chest into what now looked like a pair of women's breasts, or by the bulge blossoming inside my panties.

"You better turn around, Sally," Margaret said grabbing a handful of tissues from of the box. "You don't want to see what I'm about to do to your brother."

I felt a hand reach inside my knickers and within seconds I felt a familiar sensation flowing through my entire body. As I slowly became aware of my surroundings again, all I could hear was hysterical laughter.

"That didn't take long," mocked Margaret between breaths. "You are going to have to learn to control yourself better than that if you're expecting to date me."

"He's going to need a panty-liner," said Sally, "so he doesn't stain my clothes."

Before I knew it, I had one in my hands with instructions ringing in my ears on what to do with it.

"Peel off the backing, place it inside your panties, and fold the wings back so it doesn't slip on you."

Having just emptied my load, I feel like putty. I dutifully did as I was told as if I was a robot under remote control.

"We need to do something about that so it doesn't get free again," said Margaret reaching for her handbag. "I have an idea. Close your eyes. I want this to be a surprise."

She pulled out a scarf and tied it around my eyes. I felt my panties being pulled down and replaced by some sort of G-string with what seemed like a pouch for my penis.

"My God, Margaret!" shrieked Sally as the room filled with screeching and giggling. "Where did you get that from?"

"From a friend," replied Margaret somewhat evasively. "Not only does it hold his penis in place," she explained, "it also contains on opening so he can pee like a real girl."

As the scarf was removed from my eyes and my sight re-adjusted to the bright light, I looked down between my legs in utter disbelief. I was frozen in shock. All I could do was run my hands up and down the latex rubber feeling what looked like real hair surrounding a real vagina!

"Look," yelled Sarah almost crying with laughter. "He's fingering himself already. He's a natural at this."

Flashes blinded me momentarily as I suddenly realised someone was taking photos.

"What are you doing?" I screamed recovering from my stupor. I made a dash at Margaret but she was too quick for me. The camera was tossed around the room from girl to girl while I stumbled about pathetically.

"We can't keep calling him a 'him' any more, not looking like that. What shall we call our new girlfriend?"

"How about we call her 'Dorothy', like in 'The Wizard of Oz'?"

"Yeah! Dorothy! You are not in Kansas any more…"

I felt totally humiliated. This was not what I had expected. A girl I had the hots for had just given me a 'hand job' and I hadn't enjoyed it one bit. Well, I may have enjoyed the orgasm, but not what had come with it. The girls were really enjoying themselves at my expense and I felt hopeless to do anything about it. I stood there frozen with shock, barely able to breathe, let alone move. And now I had the additional humiliation of being called 'Dorothy'. They kept repeating it over and over to the sounds of ever-increasing bouts of uncontrolled laughter.

"Dorothy, why don't you ask the Great Wizard for a brain so you can learn to keep your chauvinistic mouth shut?"

"No! What Dorothy needs is a dildo for her new vagina so that she can really feel what it's like to be a woman."

I felt myself shrinking from humiliation. But not my penis. It was as hard as ever but with nowhere to go.

"Now, Dorothy," interrupted Sally. "One of the 'joys' of being a woman is that you are not allowed to have any body hair."

"No way!" I panicked as I watched her opening a packet of waxing strips.

"Don't look so worried, Dorothy," said Sarah, cuddling up close to me. "Even men wax their bodies, cyclists, body builders … It's just that us girls have no choice."

"Well, I'm exercising my choice right now. This has gone far enough. The bet is off."

"Oh well, we'll just have to post these photos on the web and email the address to all our friends", said Margaret. We'll tell them that we caught you trying on your Sally's clothes. I doubt if you'll get a date around this town after that."

"Oh, I don't know," said Margaret. "There might be a some dyke out there that might find Dorothy quite cute."

"You sneaky bitches,'' I cursed.

"Oh, come on, Dorothy," crooned Sarah. "It's only for a week and then I will be your reward. I'm actually looking forward to our date."

"There are two types of strips," continued Sally as if she had missed completely what had been going on. "One is for the general parts of you body like your legs, and this one is for the more sensitive areas like your bikini-line and your underarms."

Margaret and Sally eased my arms up to the top of my head while Sally patted one of the strips in the middle of my underarm. Without warning, there was a 'zip' sound that nearly sent me through the roof.

"Don't be such a baby, Dorothy," mocked Margaret amid fits of laughter. "Even little girls don't carry on like you do."

I tried as hard as I could not to show any pain, but couldn't help but wince to each 'zip'. I was amazed at how quickly every last hair had disappeared from under both my arms into a clump on two small strips. I nearly cried as what little hair I had accumulated on my chest soon disappeared as well.

"Now, let's rub in this lotion. By tomorrow morning your body and underarms will be as lovely and smooth as a baby's bottom. If you had shaved them, they would still be stinging and itchy a week later."

By now it was pointless to resist. Sally's red top with the cowl neck was next. The silky material actually felt quite nice. It had three quarter sleeves and I couldn't help but stroke the softness of the material on my arms. What shocked me most was what it did around my breasts. The bra may have rounded them up but the tight top seemed to accentuate them all the more. Even without any padding, I had a reasonable pair of breasts.

But there was no time to dwell on things like that. I gritted my teeth as the girls waxed my legs and bikini-line. It was really painful but I held it all in to deny the girls any more opportunity to make fun of me. I have to admit, though, I did enjoy how they rubbed in moisturiser afterwards, especially as they made their way up around my crotch. From what I could tell, they didn't seem to mind it too much themselves. If this is what came with waxing then it may just have been worth it. I put my panties back on almost relieved to be covering up what I could only describe as a 'nightmare' between my legs.

I slipped on a pair of Sally's trousers without protest. They didn't feel like any I'd ever worn. They may have had a fly like my own, but it opened on the wrong side. They didn't even have any pockets. They seemed really tight around my hips and between my legs. I couldn't believe how flat the front of stomach was where there had once been a bulge. I had to admit that they looked quite stylish. I wasn't sure if my legs were tingling with coldness from the waxing or from the softness of the material.

The girls started painting their toenails and showed me how to do my own. Their humiliating laughter seemed to have turned into playful giggling. This must be what girls do when they get together I thought.

It seemed like I had been accepted into their inner sanctum. I sat around with them with my legs crossed in ladylike fashion. No one had told me to do that. It just seemed to be the obvious thing to do given my predicament. They cut some false nails to fit my fingers and showed me how to stick them on. I made a bit of a mess painting them, but the girls helped fix them up for me.

By this time my toenails had dried well enough to put on a pair of Sally's shoes on my feet. They were platform sandals and, forgetting for a moment that I was looking down at my own feet, I caught myself admiring how attractive my painted toenails looked poking out from beneath the straps.

"This next bit is going to take a bit of practise, Dorothy, but it is something us girls have to do everyday," said Sally, as the girls started applying make-up to my face. "Lipstick and mascara are essential, some light eye shadow and blusher add a nice touch as well."

"There!" announced Sally. "Stand up so we can look at you properly."

"Wow, Dorothy" said Margaret. "You don't look half-bad. If I was a guy, I reckon I could go for you."

"Now you truly can be one of us," wailed Sarah.

I played along with them for a bit of a joke, prancing like a model on a catwalk.

"Don't get too comfortable with this just yet," said Sally as if concerned that things might be getting out of her control. "This is just the beginning. Your week starts tomorrow. These are the clothes you need to put on in the morning. Margaret is going to pick you up at 7 to take you to do your hair."

I went red in the face as I remembered that Margaret was a hairdresser. But any fear about what she might do to my hair paled into insignificance at the thought that I would have to go outside dressed as I was.

"On, no!" I said. "I can't do that!"

"Don't look so worried, Dorothy," said Margaret putting her arm around me. "I'll look after you. We'll have you in and out of the shop before anyone else arrives. I'll give you a nice practical hair style you can wear all week long without requiring too much looking after."

"You'll also need a handbag if you are going out," interrupted Sally before I even had time to complain. "This one's got most of what you'll need. You can also use this purse but you'll have to put your own money in it."

The girls strapped the handbag over my shoulder and once again started leading me by my hands.

"Where are you taking me now?" I asked with some trepidation.

"To show you off to mum and dad," said Sally. "It wouldn't be fair for them to miss out on all this fun."

"Please," I begged to deaf ears. "Enough, already." Before I knew it, I was at the bottom of the stairs being dragged into the lounge room.

"Mum, dad, I'd like to introduce to you our new girlfriend, Dorothy," Sally declared.

"Oh my God," muttered my mother, "I can't believe you actually went through with this."

"Mother," I exclaimed with a tinge of betrayal. "You actually knew about this?"

"Now, Jeremy…" mum started saying with a chuckle.

"It's Dorothy, mum," corrected Sally. "Jeremy is away this week. Dorothy is taking his place."

"Dorothy, is it?" mum burst out laughing. "It's a pleasure to meet you, Dorothy. You look very nice today ... Look, this business is between you and Sally. As a woman myself, I have to say that I was somewhat offended by your comments. So, in a way, I'm glad it has come to this. You might be surprised at what we women have to go through. This experience might teach you some compassion and humility. How do you like it so far?"

It was an awkward moment. I didn't want to admit my embarrassment, as it would have meant that I had been wrong. On the other hand, I didn't want to sound as if I was enjoying myself either.

"It's no big deal," I lied, pretending to be blasé about it all. "They're just clothes."

"Oh, come on, Dorothy," teased Sally. "You're one of the girls now. Come and sit down with us."

I looked to my father.

"You're on your own on this one, Dorothy" was all he could say. "I'm glad I'm not you."

He poured us all some drinks, which helped me to relax a little and to make the evening pass quicker. The girls made me drink Irish Cream instead of my usual beer and I found it surprisingly quite strong. I ended up more than a bit tipsy and even caught myself giggling at times.

There was no mistaking the lipstick smudges on my glass or the long red fingernails on the end of my hands. They were ongoing reminders of my circumstances. Keeping my legs crossed and my hands folded on my lap in proper ladylike manner while sitting wasn't as easy as I might have imagined. I found myself having to gently rock my leg from time to time and to twirl my foot around so that my muscles wouldn't fall asleep.

As my body continued to behave as if it had a mind of its own, I realised I was feeling quite delightfully feminine. I put it down to the affects of the alcohol and didn't worry about it too much. I didn't dare admit it to anyone but I was actually starting to enjoy myself … as a girl. It was something I'd never experienced before and I secretly allowed myself to revel in it a bit.

Gradually the conversation went from me onto other things and the rest of the evening went like any other. The girls still teased me every now and then and I played along with them. When the conversation got onto the post-summer sales on around town, mum couldn't resist saying,

"You must take Dorothy to Katies. They have some wonderful clothes at give-away prices that would really suit her."

"Oh we will," said Sally ominously. "We are going to hit the malls early on Sunday and 'shop till we drop'. But first thing tomorrow, Dorothy is having her hair done."

"Yes, of course," Margaret replied. "I nearly forgot that tomorrow is an early start for Dorothy and I. I really must get going."

With that, Margaret and Sarah said their farewells. I was relieved when they had finally gone and all the "Bye, Dorothys," had finished. But my night was far from over.

Sally took me upstairs and showed me how to remove my make-up. She left me with a pair of satin shortie pyjamas and went off to her room saying,

"Be sure to hang up your clothes nicely so they don't get creased. You want them looking good for tomorrow."

As soon as the door closed, I raced for the tissue box, allowed my pants and panties to fall to my ankles, and released the juice that had built up in my penis. It was a bit weird having the cum drip out my new hole but no less pleasurable.

I picked up the pyjamas. They weren't a lot different to any that I might have worn myself, yet no self-respecting guy would ever be seen in these. They buttoned on the wrong side, of course, but I was getting used to girls doing everything back-to-front. The problem was how cute these jarmies were. They had these little brown bears going shopping in patterns over bright pink background. The satin felt so silky against my body, like wearing boxers only all over. I was suddenly aware of how much I was enjoying wearing them. I couldn't help myself. With no one there to see me, I slid into bed feeling remarkably contented.

Reflecting on the evening, I had to admit that I hadn't had so much fun in a long time. Sure, it was a shock to be transformed into Dorothy by the girls. However, it felt as if I had become best friends with Margaret and Sarah. And while it was pretty embarrassing having to face mum and dad in this way, after spending time sitting around talking with them, it no longer felt like such a big deal. But the scariest thing by far was that Dorothy had enjoyed herself. It made the prospect of going outside tomorrow morning somewhat easier to handle.

Technically speaking, I had already lost my bet. I now realised how vastly different wearing Sally's clothes was to that of my own. There were times I had felt so feminine it was almost scary, excepting for the fact that it had also felt so nice. But I wasn't going to admit that to anyone. I was going to milk this for everything it was worth. I feel asleep dreaming a dream I had dreamt many times before – making love with both Margaret and Sarah. It now seemed closer to reality than ever before. I could hardly wait for tomorrow.

To Be Continued …

© 2002

  

  

  

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