You Wear It

I might have been attracted to Jules for all the wrong reasons. I mean, she was bigger than me, stronger than me, maybe even more masculine than me. You might think that she was a lesbian if you met her, but when we first got together, she was in a princess costume and she looked gorgeous.

"I don't wear these sorts of clothes normally," she said. But that was what she was wearing when she bowled me over. I sort of liked the roughness of her underneath the pink frills. But I liked the pink frills even more.

I was guilty of trying to make her into something she was not. That was what pissed her off. I bought her feminine things to wear. She always avoided putting them on, even in private.

"If you like dresses so much you should wear them," she said.

She had nice hair and she had it regularly treated and colored at the local salon. But she never did anything with it. I suggested that she put it up or try some waves or curls. She was having none of it. She wore it pulled back in a tight ponytail most of the time.

"Curl your own hair," she said.

She had strong facial features. Not so masculine, but not too feminine either. She had good skin and said she didn't like to paint her face with makeup. She used lipstick occasionally. That was enough for her. I suggested that when we went out at night, she should shape her eyes a little and maybe try some mascara and eyeshadow.

"If you're the expert, do it on yourself," she said.

I am not sure what I said that put her over the edge, but I suppose I knew she was getting increasingly pissed by my efforts to modify her look.

Has there ever been a time for you when you know you have gone too far already, but you just keep pushing it? For me, that was the dress. Jules had stayed overnight at my place. I had bought a pretty blue lacy dress that I thought she would look great in, a few days earlier. Before she came over the night before, I realized I could squeeze into the dress. While she was having breakfast I stepped into the room wearing it. She just glared at me.

"You would look great in this," I said, in the full knowledge that it would likely send her over the edge.

"Take it off," she snapped at me, with a murderous look in her eyes.

I just shrugged and when I came back a few minutes later she seemed to have calmed down. She had poured me a nice big cup of coffee. I was set to go to work so I downed it. And that was all she wrote.

The next thing I knew I woke up in my bed and it was dark outside. That could only mean that I had been unconscious for around 12 hours.

But I realized that things were not right. I felt trussed up like a turkey. There was something lying over my face, but as I raised my hand I saw that it did not look like my hand at all. It was a girl's hand -- soft and smooth with long fingernails painted pink. And I was using it to brush hair away from my face.

I struggled to sit up, but I still felt a bit woozy. I was wearing the dress. My legs were not right. They were smooth, like my hands and my arms -- stripped of hair and soft and moist to the touch. The hair was back in my face.

I needed to get to the mirror across the room. It was then that I realized that there were shoes on my feet. High-heeled shoes, strapped onto my ankles in a way that did not allow for them to come off. It seemed hardly possible that these had been fastened to my feet in such a fashion, but I had no choice but to totter across the room in these shoes, to look at myself.

And this is what I saw.

It was not a wig. Hair had been woven into or attached to my own hair and had been styled into an updo which had become just a little ragged while I had been lying down.

My face was completely smooth and somehow plumper than it normally was. The lips too were fuller. My face felt numb.

It had been made up by an expert, that was clear. There was a use of color and some heavy work on the eyes. My brows had been shaped.

Perhaps I should have been horrified, but in fact I was fascinated. It was clear what had happened. Jules had said: "If you like makeup, you wear it." She would look great if she had sat for a makeover like this, but instead, she had arranged for me to have it.

Her idea of a clever joke.

And I looked really good. More than pretty -- absolutely gorgeous.

The dress fitted perfectly now because underneath it I was wearing some kind of shaping garment. It gave me a bust, hips, a cute butt, and held my junk in super tight. It was cinched in at the waist to give me a sexy hourglass figure. That was accentuated by the heels which made my legs look a mile long, clad in black patterned stockings fastened to straps coming off the undergarment. Sure, the shoes were hard to walk in, but they were great for posing in front of the mirror.

I tried to force a smile, but it was not easy. What was wrong with my face? But it did look good.

I tottered into the living room. I expected Jules to be sitting there, doubled over with laughter. But she was not there. There was a card on the counter. A pink perfumed card with flowers on the front. I opened it.

"Beautiful Steffi,

Date night tonight.

Expect full attention,

And the best sex you have ever had.

Be ready at 7:00 for your pick up.

XXX"

Steffi. This was my new name. Very funny. But the rest of the card was exciting. And even more exciting was looking at the clock and seeing that it was only a few minutes before 7:00 pm.

On the counter were a shawl and a silver handbag to match the shoes I was wearing. In it were lipstick, mascara, some tissues, and a tampon. What a comedienne.

Alright. Let's play this game. I did not appreciate the fact that I had obviously been drugged and stripped naked that morning, but no apparent damage was done. I could take a joke. I had been a prick to her after all.

My doorbell rang. I did not check to see that it was her. I pulled myself into a suitably vampish pose and I swung open the door.

A man was standing there. He was tall and wearing a very smart suit and tie. Even in those clothes I could see that he was powerfully built, and he had a face to match -- a square jaw and heavy brow. A very handsome and very masculine man. And I was standing in front of him, the very opposite.

"Steffi?" It was not really a question. "Wow, you look fantastic. And obviously ready to go. Great."

He crooked his arm towards me, inviting me to put my own through his, and to walk down to his car. It must be his car? The yellow Audi TT?

"Where is Jules?" I asked. It came out as a croak. I cleared my throat. "Is she watching?" This time it came out in a high pitch.

"I'm taking you to the best restaurant in town, as instructed," he said. "My name is Ken. I'm sorry that I did not introduce myself. I'm here to ensure that you have a great night."

That sounded OK. Those were the words. I should go with him. It seemed to be part of the joke. I looked around and I could not see her. I figured that she would be at the restaurant. The best one in town. I had no money. I would not be paying. I was all dressed up. What the hell. I slipped my arm into his. I said: "Pleased to meet you, Ken. Let's go."

So we did.

After we sat down, I spent maybe 10 minutes looking for Jules to arrive. But after that, I just kept listening to Ken. He was keen to talk about himself, but he was an interesting guy. He worked in resource development and he had travelled all over the world visiting developing countries and talking to indigenous landowners about how to look after what they had. It seemed like admirable work. He was an admirable guy.

My life seemed so uninteresting compared to his. That is exactly what I told him when he asked me about myself.

"Maybe I've fucked things up with Jules?" I said.

"Maybe," he said. "But that's why I'm here."

"So how did you get involved in this?"

"I'm interested in a special kind of woman," he said.

"Well, I'm sorry. I'm not one of those. I'm not any kind of woman."

"Really?" he said. "You sure look like a woman to me."

"I do, don't I?" I said. I could see my reflection in a mirrored panel on the far wall. I was holding up well. But the compliment made me wonder if I should freshen my mascara and lipstick. Except that I had no real idea how to do that. I mean, I had seen other girls do it. I should at least check.

Dessert arrived. Dessert? We had been talking for hours.

"You may think that this is a bit forward of me, but would you consider visiting my place before I take you home tonight? I want to show you something. Something that might change your life."

I was curious. He was not giving anything away, despite me pestering him in my increasingly girlish manner all through the last course. The only way I was going to find out what the life-changing thing was, would be to pay a visit to his home on the way back to my place. As I say, I was curious. And he was a complete gentleman.

His house was huge. It was on the point, overlooking the sea. The most expensive real estate in town. He assured me that he lived there alone, but this was large enough for many guests and big parties.

"The only thing missing is a hostess," he said.

"So what did you want to show me?" I asked him.

"I have a gallery of photos of all the interesting places I have been to and people I have met," he said. "But that wall at the end is devoted entirely to people like you."

"This wall. Well, they are all beautiful women. Quite a few of them naked. But tastefully so."

"They were all once boys," he said. "They are all now women. Happy and fulfilled. Here from Thailand. Here from the Phillipines. Colombia. India. Turkey. China. All now women."

"No, no," I told him. "That is not me. My girlfriend Jules is just messing with me. I'm not ...."

I did not have time to finish because his tongue was in my mouth. I was in his huge powerful arms and he was kissing me. And of course, I was doing my best to fight his off. Well, maybe I thought about it. For a nanosecond. Then after that I was kissing back.

Was it the wine? Was I still affected by the drugs that had me unconscious only 5 hours before that? Or was it him? Or me?

"I want to make love to you," he said.

"I can't," I insisted. Not "I won't" or "Fuck off you pervert;" no, just: "I can't," as in: "I would if I could, but I can't."

"You can," he said. His face was close to mine. The smell of him still affecting me. "You're ready. Let's get that underwear off you."

Now that sounded like a good idea. My waist was squeezed tight, I was busting to piss, and I felt as if I was lined up for a huge dump.

"I do need to borrow your bathroom," I said. I was thinking that when I got in there, I would lock the door, do what I had to do, and get my thoughts together. I was behaving very strangely. It was as if I had turned gay. Dressing as a woman had turned me into a faggot.

I slipped the dress off and looked at myself in this garment. I could not get my shoes off as I could not find a buckle, and nor could I find some way out of this panty, corset and bustier thing.

"Ken, I'm going to need your help," I called through the door.

He was standing right outside. "Unlock the door then, I will help you."

He seemed to know exactly what to do, which was troubling. Under the feature on the top of the shoes was a latch which freed them. He helped me take off the shoes and he rolled down my stockings one by one, stroking my hairless legs as he did so. The sensation was not unpleasant, but the circumstances were still odd. At the back of the shaping garment there was a hidden catch which allowed it the break into pieces.

The bustier came off first. It had padding and had forced the flesh on my chest up into a cleavage with such force that it almost appeared as if, once it was off, that I still had a pair of tiny breasts. Next the corset came off and left behind something of the curvy shape of my abdomen. Finally, the front part of the panty fell away. My penis had been secured back between my legs and my balls pushed up. They seemed reluctant to drop back down. But the back of the panty section seemed still attached to me.

"You will need to sit down on the toilet for this, and pull it forward," he said. I was puzzled, but I needed to go.

I suddenly realized as I moved to the toilet, that there was something in my butthole. I seemed crazy that I had woken, walked around and sat down to dinner for hours, without noticing it. Now getting what ever it was, out of me, was a priority.

"Take it easy now," he said. "Slowly."

It came out easily with a pop and what followed it was a cascade of liquid into the bowl. In my hand was the panty part of what I had been wearing complete with a large dildo attached that had been plugging me. It was so big that it made me shiver and made me realize that my anal sphincter had yet to fully close. The smell coming from the toilet bowl was not of diarrhea but of flowers. Whatever the liquid was that had come out of me, it was not shit.

"Oh my God," I said. He helped me to my feet and took some toilet paper to wipe my butt. Has anybody ever done that for you? Somehow having it done by somebody else makes you feel totally helpless and childlike. He took my hand and led me back to bed.

"Now we can make love," he said.

I looked up at him and I was still in some kind of disbelieving trancelike state. But when I felt his penis enter me it seemed to just glide in. Somehow I had been prepared for this hours before.

"Can you squeeze me?" he asked.

I had no idea how to do what he wanted, but somehow I did. He sighed with a look of joy on his face. He kissed my nipple and then my lips. He wriggled to bring me into position beneath me. I could feel him. I could feel every stroke inside me, and I could hear the slurping sounds of a well-lubricated butt being pounded by a virile man.

"Is this what you want?" he whispered in my ear, without breaking his rhythm.

What could I say? 24 hours previously I had been a man wanting nothing more than to be in his position now, fucking Jules, about to come inside her. Now I lay beneath a man, and he was about to come inside me. But not before ....

"Oh, oh, oh, yes, yes, yes. This is what I want. This is what I want. Yes." It was me. A girly squeal, but out of my mouth. My little cock was squirting my own jizz all over my face, while his was filling me up with his seed.

There was no going back from that. He was looking down at me and smiling.

"I promised you my full attention and the best sex you have ever had," he said. "Did I deliver?"

He wrote the card, not Jules. He wrote the card.

"Yes," I said. "Yes, you did."

The End