tagCelebrities & Fan FictionWearing Her Clothes

Wearing Her Clothes


This is going to be the best Halloween ever! I took off from work early to avoid the holiday traffic; it's always crazy on Halloween, with people becoming absolutely desperate to dress up as a nurse or a caveman or a pirate. Rushing around, going to their parties... I'm not going to a party; I'm spending Halloween on my own. I have a plan... I also have the best costume in the world!

I sink into the bath, watching the bubbles rise and almost spill from the tub as I relax in the warm water. I usually shower - I haven't had a bath in years. Bubbles and stuff always seem to be something that women do. Still, the bubble bath did come with the outfit! It was hers, so obviously I'm going to use it tonight!

I got lucky this year, real lucky. A few weeks ago, I'd been in Miami on business and stayed at one of the better hotels. On the evening of my third day, I went to reception to check for messages. Unbelievably, she was checking in! And they put her on the same floor I was on! We shared an elevator and engaged in small talk and, by the time I got to my room, I was ready for the best wank of my life!

We met a few more times after that, in the restaurant and bar. I actually sat with her in the bar for a while on the last evening of my stay in Miami. She was waiting for someone and he was running late. I never actually found out who she was waiting on, but I presumed it was her boyfriend or husband or something. I had another glorious wank that night, and in my fantasy she had been waiting for me at the bar. We'd come back to my room and I'd slowly remove her dress... I'm sure you get the idea!

Anyway, I booked out the following day and somehow the hotel managed to mix up her overnight bag with my luggage. I was so stunned at meeting my teenage idol and talking to her that I didn't spot the extra bag until I arrived home! My own overnight bag was in my suitcase - all my samples had been distributed, so there was plenty of space for it.

Here I was with the best possible souvenir ever! Inside the bag was the dress she had worn on that last night in the bar, the dress that had played a pivotal part of my fantasy! I had photographs of her in that dress, of the two of us sitting at the bar! Me and Molly Ringwald!

I lathered my legs and shaved them. It wasn't too difficult, I'd seem movies where women sit in a bathtub, a towel wrapped around their hair, to shave their legs. It always looked so feminine, and I was glad I had lit some scented candles as I imagined Molly shaving her legs... I felt my cock stiffening up as I stroked the razor over my legs, pretending that I was Molly. Of course, she didn't have to shave her chest!

My lust for Molly Ringwald began after seeing her in a few movies back in the eighties. My favorite was Breakfast Club, where she does a little dance... I guess I was drawn towards her because I have red hair too, unlike most of the people at my school. I could identify with her; we had something in common.

Now I had the chance to really identify with her - for one night, I could become her! I finished shaving my chest and stood up to depilate all those areas that had been under water. My cock was rigid as I worked, and I thought briefly about shaving my pubic hair off. No, perhaps later... I didn't know if Molly shaved down there, so for my first transformation I decided to keep my hair although I did even it out a little.

After discovering that I had inadvertently brought Molly's bag home with me, my first reaction was to return it to the hotel where they could re-unite it with Molly. My curiosity got the best of me, and as I looked through the contents of the overnighter, a plan began to form in my mind.

The bag held the black dress she had worn on that final night, some underwear, a skirt, three different tops ranging from smart-casual to lounging around in leggings, leggings, two pairs of shoes, a toiletry bag and a digital camera. I was amazed by how much she had managed to cram in there! With all of this stuff, it would be easy to imitate her for a few days...

I decided to return the camera to her - it was an expensive model, really top quality, and I couldn't keep that. I'd return some of the other stuff too, but only after I'd had some fun.

My body felt really smooth and tingly as I stepped from the bath. I dried myself as I contemplated my next step; should make up go on before or after my clothes? I decided to do my make up first, that way I could spend all my dress-up time in complete enjoyment of being Molly.

The Internet is a wonderful thing, with all sorts of pages on how to do make up properly! I'd even found some pages that explained how to achieve a realistic pair of breasts - that was on a site for cross-dressers. I picked up a few other hints and tips there, especially for men who want to look like women.

The make up went on easier than I thought it would - I really didn't look too bad once I had finished! My cock wasn't as hard as it had been earlier, it was still longer than usual but it was kind of relaxed... just nice.

Molly Ringwald wouldn't be Molly Ringwald without wearing pink, and the bra and panties I had decided to wear were the perfect color! They weren't too skimpy but as I adjusted the panties, I realized that there wasn't enough give in the front of them for a cock. That didn't matter too much; the fact that I was now wearing Molly Ringwald panties was enough to please me and provoke another erection from my restrained cock! It looked really obscene, my cock pushing the pink triangle of material away from my body...

I fastened the bra and put in the special padding I had ordered from the web site. These were false breasts, but totally unlike any you would find in a Halloween store. They were very realistic, and they came with surgical glue to keep them attached to my chest. I moved them around a little until I was happy with their positioning, then glued them into place.

Molly's pantyhose were next... I wondered if she had washed them? They smelled clean enough, and I gently eased the sheer black fabric over my toes and up my leg. It felt really nice, that sensation of being encased in something so light and stretchy... I eased the other leg on and then stood up to bring the waistband up, feeling the pantyhose add to the constriction that my cock was under.

I looked in the mirror and was amazed by what I saw there! I didn't really look like Molly, that was too much to hope for, but I did look enough like her to make me very happy. I guess the main difference was that Molly wouldn't have had an erection sticking from the front of her pantyhose... Looking at myself just made me even harder, and I could feel my cock throbbing, desperate for a good wank.

I set my camera on self-timer and took a dozen pictures. If I were only going to do this once, I'd make certain that I'd have as many memories as I could!

I wasn't finished yet, however. I pulled the dress on and adjusted the fit in the mirror, once again noting how my cock pushed the clingy fabric out. Finally, I stepped into her shoes... They were black with silver trim, sort of like strappy sandals but with high heels. My toes slid in to a little pointy part at the front of the shoe while a few straps tied to my foot at the ankles to keep them on. I practiced walking in them for a few minutes before returning to my camera for more pictures.

As I posed, I became incredibly aware that I was wearing Molly Ringwald's clothes. This is how Molly's dress felt on her body, this is how her feet feel in these shoes, her pantyhose hugs her waist in exactly the same way that her pantyhose hugs my waist...

I was very hard and aching for release, but I wasn't ready for my wank just yet - I had many more pictures that I wanted to take! However, the memory card soon filled up on my camera and it was time to transfer the first batch to the computer. Sitting at the computer I crossed my legs, something I had seen Molly do in the restaurant and bar. It felt really good as my legs rubbed together, separated by only the thinnest of material, and I was soon looking through the results of my first photo session. It was fantastic, truly incredible, and I considered making up a web page to display this transformed me in all my glory! Then I remembered that Molly's camera had been in the bag...

Molly had been doing what I was doing! Self-portraits in this very dress! As I looked through the transferred pictures I saw that Molly was doing a slow strip down to the pink bra and panties that I was wearing! Then she took them off, her body intensely moody and seductive, for some nude shots. I searched through them all but it was all very soft-core stuff, not even one nip-slip...

I almost ran back to my impromptu studio and took another batch of pictures, this time posing as much like Molly as I could, right down to the nude shots. As soon as the camera filled up, I got dressed again.

The latest set of pics could wait - it was time for a break. I also had to eat, and I made up a sandwich to enjoy as I watched a movie - the one where Molly gets topless, of course! I'd watched all of my Molly Ringwald collection in the evenings running up to tonight and had saved Malicious for last. I only intended to watch that one scene, and settled down with my sandwich and a glass of wine.

Twenty minutes later, I switched the DVD off completely stunned by my reaction. I was rock hard again, of course, but while watching the scene I had begun to imagine that I was Molly Ringwald. I yearned to kiss her lover's chest and take my top off for him; I longed to feel his penis slide inside me... This is not what I had expected, and I sat for a while trying to figure out what this meant.

Was I gay? Did I want a sex change? Did I want to be Molly Ringwald? These were the three main questions in my mind, and I finally decided that the answers were no, no, and yes but only if I could change back to being me again. Perhaps wanting to be Molly made me want to do the things she did on screen...

The doorbell rang. Shit, the doorbell rang and I was dressed like this! I started to panic but then remembered that it was Halloween - lots of people were dressed differently! I decided to answer the door dressed as Molly Ringwald.

Molly Ringwald stood there. She too was dressed as Molly Ringwald.

"Hi, you might not remember... We stayed at the same hotel a few weeks ago. One of my bags went missing and..." she said breathlessly. Then she did a double-take. Molly's jaw dropped as she saw what I was wearing. "Is that my dress? Are those my shoes?"

She glared at me and I almost wilted, such was the intensity of the look in her eyes. I couldn't move, couldn't speak, couldn't do anything except for start to cry. I am a grown man and now I start to cry? What was happening to me?

"I suppose I'd better come in," she said, looking disdainfully at the dress.

"I never even imagined that I was popular in transvestite circles..." she said as she sat on my couch. (Molly Ringwald sitting on my couch! Exactly where I had sat!) "Cher, Madonna, Janet Jackson, yes... but not me!"

"Sorry," I managed to say.

"I suppose I should be pleased... Still popular after all these years? Okay, I came here to see if you had my bag. Obviously you do, and you've... ah... looked through it. There was a camera in there with some very personal pictures in it. Give me that back and I'll leave, although I should really have you arrested!"

I went and got the camera, placing it on the table next to the couch. Molly looked at it and then looked at me.

"There's no point in asking if you looked at the pictures or not, you'd probably lie," she said.

"I did," I replied. "They were beautiful."

"Okay, that is so not the answer that I was expecting!" she said, turning away from me. "Have you worn everything?"

"No, just this... just for Halloween." I said.

"So you're going to a party?"

"Um, no..." I replied. "This is... This is just for me."

"Well," Molly said, looking at me appraisingly. Something seemed to pass between us just then, some spiritual thing, as if our souls recognized each other. "You've done a great job! Do you do this sort of thing often? Dress up in someone else's clothes?"

"No, first time," I said.


"Why?" I replied. "I'm not really sure... I think it was mostly for an adventure, you know? To be a bit more like you, after identifying with some of the characters you played in your early movies."

"Back when I had a career?" she laughed. "Oh, I should be furious..."

"Would you like something to drink?" I asked.

"Yes..." she replied. "Iced water, please."

"Sure... It's the least I can do."

We sat together on the couch, a big distance between us, as Molly drank her water and asked me lots of questions. Mainly she asked about why I had done this, but then she asked me how it felt.

"Good, really good," I said. "Very intense... I think I almost feel like I am you, or at least my projection of how you are."

"What do you mean by that?" she asked, turning to face me and moving slightly closer in the process.

"I lost my sense of self, to an extent. I wasn't me anymore, and it was nice to be someone different, to do the things they do. Come on, I'll show you."

I led Molly into my home office and sat her on the computer chair, pulling up the folder I had transferred my photographs to. I also opened the folder containing her own photos so that she could compare.

"Oh my god!" she cried as she saw the first of my photos. I had forgotten all about being very hard when I took those! "Well, you can keep those panties!"

She looked through the rest of the photos, her face becoming thoughtful as she progressed through them all. Finally she turned away and looked directly at me, appraising her dress on my body.

"I might have an idea..." she said.

We returned to the couch in the living room to discuss her idea. Molly was in the process of setting up a production company doing offbeat human dramas and was searching for stories to transform into tele-movies. Her idea was that a man, me (and played by me!), would dress up as a woman. The man dressed as woman role would be played by Molly - this is how the man would picture himself as he interacted with all of those he came into contact with as his evenings progressed. It would have one of those clever twists at the end when the man dressed as a woman suddenly gets reality intruding in on his perceptions and fills with the knowledge of how those little meetings with other people actually went.

"Too depressing," I said. "This experience, if you pardon my saying so in the circumstances, has been incredible. You should make it a story of empowerment, of those little things that people do to get through the day. I do like the idea of you playing me when I'm dressed up, though. Nice touch."

"Okay," she said. "Tentatively, you'd get credit as a co-producer and story by... would you be willing to develop this further?"

"Yes, yes - I think so," I replied. "There should be a scene where we meet... I mean, the me dressed as a man and the me, that would be you, dressed as a woman..."

"Oh yeah," laughed Molly. "And what would we do?"

"I don't know," I replied. "Make love or something!"

"You want to make love to me?"

"With all my heart..." I replied before realizing what I was doing. I was no longer talking about the movie...

Molly placed her hand on my thigh. I think she was trying to be comforting, but the feeling of her warm hand through the pantyhose was absolutely wonderful. I felt my cock grow stiff once more.

"What possible reason could there be for that?" asked Molly. I hoped she was unaware of what was happening in the panties she no longer wanted.

"Hope," I replied, thinking quickly. "Oh, I've got it - it's a fantasy sequence, yes? His male side feels like it's constantly at war with his female side, but then they join together at the climax of the lovemaking scene. The whole transcends the sum of the parts, yin and yang combine, anima and animus unite... and there's the climax to the movie, I can dress how I want and when I want and I'm a better person for it!"

"You want to make love to me," said Molly.

"Yes," I replied. There was nothing else that I could say. "I want to make love with you."

Molly slid her hand up my thigh, under the dress. Her skin felt electric as it brushed along the pantyhose until her fingers connected with my erection. She moved closer to me, bending her head towards me. Her lips parted slightly and she licked her top lip before moving even closer to kiss me.

I wrapped my arms around her, feeling how warm she was and breathing in the scent of her perfume. The fragrance brought an image to mind - strawberries on a warm summer day, and my lips parted to taste her tongue as it pushed into my mouth.

We moved closer until my false breasts were almost touching Molly's real breasts, her fingers still on my throbbing cock, our pantyhosed legs brushing together as we embraced. It was an uncomfortable position - too many points of contact and not enough direct access, and we stood up to face each other. Molly wrapped her hands behind my neck and drew me close for another kiss.

We pressed together properly this time, our breasts (fake and real) touching through our dresses, my hard cock pressing against her as we kissed. I felt my legs go weak but I never wanted to end this moment as Molly pulled away slightly to look at me, biting her bottom lip as her eyes stared into mine.

"I can't believe I'm doing this," she said as she backed me towards the bedroom.

I reached up to undo the strap behind her neck. The front of her dress fell free as we edged towards the bedroom and I looked at her creamy skin, her cleavage almost bare now. She stepped away from me as we reached the bedroom door, pulling her dress down to expose her wonderful breasts.

Reaching out very slowly, I gently stroked the skin between her breasts, barely aware that she hadn't been wearing a bra. The cups of her dress must have built-in supports, as her breasts sagged slightly without the material over them. My fingers explored outwards, gently touching her soft skin and brushing past her proud nipple.

Molly sighed and closed her eyes, content to enjoy this exploration as I enjoyed it. I briefly wondered if Molly was imagining it to be herself that was touching her as I cupped her breast. My fingers moved gently as my palm supported her, and I could feel her cool breath against me as I moved my hand lower.

Eventually my fingers slid under the waist of her dress, touching the top of her pantyhose. I slid my other hand around her back, undoing the zip to let her dress fall down, while easing my fingers into her pantyhose.

I'm not sure if it was Molly or me who trembled slightly - perhaps it was both of us as we stood there, my hand on her abdomen under her pantyhose. Finally I moved closer to her to kiss her again, my cock throbbing as never before under my layers of clothes.

Molly turned away from me, walking towards the bed. There was just enough light in the bedroom for me to see that she hadn't been wearing any panties, and I decided to try that for myself as soon as possible.

I couldn't believe how beautiful she looked as she lay down, waiting for me to join her. I walked to the side of the bed, watching her carefully all the time, committing every detail to memory...

Molly reached up under my dress, feeling for my erection again. She stroked me through the panties and nylon, and I swayed in time with the movements of her fingers. Molly hadn't taken her shoes off when she got onto the bed and I decided to do the same, kneeling beside her with her hand exploring me as I bent to kiss her tummy.

I rested my hand on her thigh as I kissed and licked her tummy, working my tongue down to the waistband of her pantyhose as my fingers slid up the inside of her thigh, feeling how damp and hot she had become.

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byTheEvelyn© 2 comments/ 40297 views/ 2 favorites

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