tagTransgender & CrossdressersCross Dressed Damsels

Cross Dressed Damsels



Copyright Oggbashan March 2018

The author asserts the moral right to be identified as the author of this work.

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons.


My husband Derek is a bedroom transvestite. He gets aroused and excited by dressing as a woman. He doesn't want to be a woman, or to dress as a woman would normally. He likes wearing ball gowns, wedding dresses, and massive hooped skirts. Most of all he likes pretending to be a damsel in distress. But he wants the villain who has captured him to be female -- me, his wife Anne.

I like playing damsel in distress too, captured by Derek. We take it in turns to be the damsel in our bedroom.


It all started several years ago when Derek and I joined a beginners' sewing class. I wanted to be able to do some dressmaking with a sewing machine. My grandmother had been a professional seamstress. My mother could sew on a button or repair a dropped hem but that was all.

Derek and I were both members of a re-enactment group. We wanted to be able to make some of our costumes because they were so expensive to buy. I hadn't known he would be at the sewing class too. We had been part of a group of friends for years but just that. We were friends and acquaintances and had never been on a date.

We had seriously underestimated the skills necessary to make costumes. Derek wanted to make soldiers' uniform jackets. I wanted to make gowns and dresses from medieval to Victorian. Although we had joined the beginners' class it was obvious from the first session that we were the only beginners. Every other woman -- of course Derek was the only man -- had been to two or more years of beginners classes. They all knew how to work a sewing machine, how to sew a seam, make a pleat, add a frill and much more. Derek and I could barely thread a needle. We had no idea how to use a sewing machine.

Janice, the tutor, saw in the first few minutes that Derek and I were absolute novices. She sat us together and spent more time with us than the rest of the class. By the coffee break we had hand-stitched a square of material. The other class members were working on projects from last term's session.

Derek was a hit with the other women over coffee. He was the first man to attend the sewing class. They were also interested in our desire to make costumes but dubious about whether we would actually reach that standard. Derek and I agreed to bring some of our costumes next week to show what we wanted to do. After coffee we practised sewing with a machine, doing straight lines on thin card with no thread. We were pleased that we had at least learned something.

Derek had come to the class by bus because his car was being serviced. He was pleased to accept a lift in my car at the end of the lesson. He asked me to wait a couple of minutes because our tutor Janice wanted a word with him.

I was surprised that he was so relaxed in the passenger seat.

"Why?" I asked.

"Why what, Anne?" he retorted.

"Why are you so calm while I'm driving?"

"Why shouldn't I be? You are competent, careful and a good driver."

"I am? My previous boyfriends hated being driven by me, Derek."

"I don't know why they hated it, unless they thought they should be driving, not you."

"That might be it. I wasn't happy with their driving. They drove too fast and took too many unnecessary risks."

"I think you're probably a better driver than I am, Anne," Derek said. "I used to leave things too late to go somewhere and have to drive faster than I like to make up the time. I know I do, so I have been allowing myself more time for a journey. It works most of the time."

"When do you get your car back?"

"It should be tomorrow morning. The garage will ring me at work. It's for a service and the annual roadworthiness check. I don't know of any problems so it should pass easily. If not? I can do without my car for a few days."

"OK. What did Janice want to talk to you about?

"She was concerned that I might be embarrassed over the next couple of lessons."


"The usual items for beginners to make are two or three gradually more ornate aprons and then a skirt."

"Is that a problem, Derek?"

"No. I expected something like that when I signed up. Making men's clothing is for advanced students. An apron is simple, so is a basic skirt."

"OK. So you'll do them?"

"Of course. That's the way to learn to sew."

"What costume will you be bringing to the class next week, Derek?"

"I thought I'd bring a hussar jacket. It has complex braiding that could be difficult to sew on to a jacket I'd made for myself. But I think I'll need the whole academic year to be minimally competent."

"Me too. I thought of bringing a bustled skirt from the 1890s. The bustle is difficult even just to wear it. I wish..."

"What do you wish?"

"I wish sometimes I could take part in some of the re-enactment battles instead of being a female onlooker."

"Why not, Anne? Some few women already do. In a crowd in a battle scenario no one notices that they are not men. Historic uniforms are usually baggy except for cavalry. Even World War Two British battledress tops are loose fitting. If you put your hair up? You could try."

"I wouldn't want to wear a man's uniform in public without trying first."

"Of course not."


As I dropped Derek at his home he asked me for a date. I agreed. We would go out for the day on Sunday, to a costume museum both of us had intended to visit but never had. If his car was ready he would drive. If not, he would walk to my place and we would go in my car.

Derek's car wasn't ready on Sunday. It needed a replacement part that was on order to be delivered and fitted on Monday. He arrived on my doorstep about five minutes before the time we had agreed. The weather was threatening rain. It arrived as we were en route to the museum about thirty miles from our town.

Both of us had never been to the museum. We knew it was busy during school holidays and had many school parties during the week. They provided replica costumes to try on, mainly in children's sizes but they had some adult sizes too. The main reason we hadn't gone was that we didn't want to go alone.

The museum was very quiet when we arrived. We had some rooms to ourselves. We had both brought cameras. We took many pictures of the costumes without using flash. We were delighted that the details were clearly visible on my pictures. I was slightly puzzled that Derek took pictures of women's clothing not male outfits. We went to the museum's cafe for lunch.

"Why did you take so many pictures of dresses and underwear?" I asked bluntly as we were waiting for our order to come from the kitchen.

Derek blushed slightly.

"My excuse, and it is an excuse, is that I wear military uniforms at the re-enactment events, even for ballroom dancing. Men's civilian clothing is of no interest to me. There are books and clear detailed references on line for any military uniform for any period and for any European country. But women's dress is much more variable and changes over decades."

"And...?" I prompted.

Derek blushed again.

"I like women wearing ball gowns, big skirts, hoops... There were many great examples in the museum displays. Sometimes I am disappointed with the inaccuracy of some of the women's clothes at our events. They wear colours that didn't exist, mix periods in the accessories, and sometimes they are just impossible for the era."

"So you're a costume nerd, Derek?"

"If I am, you might be too, Anne. Whatever you wear for our events is always correct."

I mimicked a curtsey to Derek.

"Thank you, sir. I try."

"And you succeed, Anne."

Over lunch we discussed what we had seen and what we wanted to go back to look at again. Derek complimented me on my driving -- again.

I sighed.

"Why?" He asked.

"My driving and theirs has ended two potential relationships. Two men who I thought might be more than friends couldn't or wouldn't drive so I felt safe. They hated my careful driving. We argued about driving and the relationships ended. But you, Derek, like my driving. That's a good start."

"You haven't been a passenger in my car yet, Anne. Perhaps you might find something else about me you don't like?"

"Like what? I know you are a costume nerd. So am I. Maybe you have too much of an interest in women's fashion. That might be an asset. I could discuss things with you that I'd never have been able to do with them."

"I haven't been able to persuade possible girlfriends to have any interest in re-enactment. You are already involved..."

"And we'll be fellow students at the sewing class. Even if we don't have a deeper relationship we'll be seeing each other every Thursday evening in term times. Which reminds me. What size will you be making the skirts?"

"I hadn't really thought. Does it matter?"

"I think it might. We have to make clothes that fit."

Derek looked at me.

"I think if I made a skirt it would fit either of us."

I looked at him.

"You could be right..."

After the meal we went back into the museum. That afternoon they had costumed guides in each section wearing modern replicas of some of the clothing on display. There were some to try on with help. In the 1890s section I started talking to the woman wearing a bustled evening gown. I have had trouble with using a bustle. The woman explained using a replica, how it should be fitted and adjusted. She offered to demonstrate on me.

"Not on me," I said. "I won't see how it's done. Put it on him."

"Him?" the guide queried.

"You won't mind, will you, Derek?" I asked.

"I suppose not. It's important to you."

The guide and I were giggling as Derek demonstrated the bustle. Even Derek started laughing as he was shown how to hitch up the bustle to sit elegantly. The guide added a heavy skirt to show the effect when the bustle was hidden. I think Derek was right. That skirt could have fitted on me.

The three of us talked about the particular era and how bustles changed over time before disappearing. The guide was slightly startled that Derek and I seemed to be as knowledgeable as she was. She hurriedly removed the skirt and bustle as we heard other people approaching up the stairs.

"You've been a great model," she said to Derek, "and one of the first men who really knows my era."

We explained that we were both members of a re-enactment society but that Derek usually wore military uniform.

I asked whether I could put on the bustle and skirt by myself to see whether I had followed the guide's explanation correctly. I had. The skirt fitted me just as it had on Derek but I wasn't embarrassed when two older ladies joined us to watch.


I didn't ask Derek to be a model again. He helped me dress myself as a woman from the mid 1860s with a large hoop extending backwards. I had worn hoops before but not that particular era. He took several photos of me. I hadn't told him I had secretly taken pictures of him wearing a bustle and skirt. Why hadn't I? I wanted reference pictures. If I had asked, I'm sure Derek would have agreed, but perhaps not for pictures showing his face. I felt guilty that I hadn't asked him.

We had enjoyed ourselves all day. We seemed to be on the same wavelength. We already knew we had similar interests in historic costume and re-enactment.

I asked Derek whether I could try on some of his uniforms.

"When?" he asked.

"This evening? I'll cook a meal for both of us. Is it a deal?"

"Yes, Anne. If you stop at my house I can get a couple of uniforms in a few minutes. I assume you want to cook at your home?"

"Yes. It would be easier. I've got a casserole in the fridge. It will take an hour or so to heat through, plenty of time for me to try dressing up."


I didn't have to wait long outside Derek's house. He came out with a large suitcase that he put on the back seat. He carried it into the large living room, the only reasonable space in my small house. I put the oven on to warm up and made tea for us.

Derek had opened the suitcase and laid out some of the uniform. As soon as the oven was up to temperature I put the casserole in. It would take an hour and a half, ample time for a dressing up session.

"Derek," I said, "I'm going to have to strip to my sensible bra and panties. Any objection?"

"No, Anne. If that's what you need to do."

I went to my bedroom and changed into a sports bra. It reduced my breasts but they were still obvious. Derek seemed to appreciate them even flattened.

I tried on a 19th Century officer's uniform first. The trousers were skin tight but Derek was right about the jackets. Once it was on and buttoned up my breasts were not obvious. My face and hair looked odd as I looked in a mirror. If I cleaned my make up off and put my hair up in a hat I could look like an officer until someone was really close. I asked Derek to take some photos of me.

"I'm sorry, Derek, I shouldn't have," I said before I handed the phone over, "but I took some pictures of the bustle and skirt on you."

"You did what? I don't want anyone seeing pictures of me wearing skirts, Anne."

I didn't appreciate -- then -- that he had used the plural skirts.

"I need them to get my bustle fitting correctly, Derek. If I have to, I'll crop them so your face doesn't show."

"Face or not, Anne, I would be embarrassed if you shared them with anyone."

"I won't. I promise. They're just for me, for reference. Is that OK?"

"I suppose so. I have to trust you, Anne."

I kissed him. He was startled at first but soon responded.

"And I've got something else embarrassing to ask you, Derek," I said as our lips parted.

"You have?"

"Yes. I want to fit MY bustle and skirt on you. I've tried on myself several times but failed. Now we have been shown..."

"OK, Anne, if you want to..."

I kissed him again. Minutes later he had taken several photos of me in several of his uniforms. I went to the spare bedroom to get the bustle and skirt. He had to shed his shoes and jeans. For a first date we were more undressed than either of us had expected. Both of us were rather nervous about it. But using the photos I had taken of Derek in the museum I was able to get that bustle correctly fitted. The skirt sat properly. Although I took more pictures I was careful to take Derek from chest downwards, not showing his face.

I took several more pictures and video of Derek walking in the skirt. After that I shed the uniform and tried to put the bustle on myself. I had to ask Derek for help. I put the black silk petticoat on before the skirt. It seemed to move better as Derek took pictures and video. They showed me wearing nothing but the sports bra above the waist but that revealed less than I would show in a bikini top.

Eventually we dressed in our normal clothes to eat the meal. I think it was a relief to both of us. For a first proper date we had shown more, and seen more than we expected. I think Derek was more embarrassed than I was. Both of us were slightly self-conscious about our exposure. I know Derek was worried by the photos I took at the museum.


Over the next few weeks we saw each other at the sewing class and at least an evening a week as well. We were working together at the class. By the end of the fourth session both of us had produced two basic blue gingham aprons each and a white cotton maid's waist apron with a frilled hem around the apron's skirt. The next project would be a full Victorian style apron, nearly floor length, with a decorated bib and frilled shoulder caps. Neither of us were sure we were competent to do that properly.

One weekend we went to a Victorian re-enactment of a Boer War battle. It took me some courage to go as a soldier, not as a lady. With my face bare of make-up and my hair up, no one really noticed that I wasn't male. My shoulder was bruised by the recoil even from blank cartridges. Derek had to help me reload. I was far too slow to keep up with the volley fire.

Some evenings we practised sewing. We made several more aprons in different materials and added details such as pockets, braiding and pin-tucking. Some of those aprons were not quite square on the waistband, or puckered at the seams. It didn't matter. We were learning how to use my electric sewing machine. Derek had one in his house, an older hand operated one. His machine was easier to control but our one-handed seams needed practice.

We recorded our efforts, sometimes with me wearing the apron, sometimes with it wrapped around Derek. Our waist sizes were very similar. If I could wear it, so could Derek. My suspicion that Derek liked wearing female clothing was turning into an almost certainty. I could ask him to model any of my historic skirts. The larger the skirt, particularly with a hooped petticoat, the more excited he seemed to get. I hadn't yet tried to get him to wear a full female costume.

"Derek," I said one evening "I have a mid 19th Century maid costume I have never worn. I can't put it on by myself. I'm not sure it fits me. Do you mind if I try it on you?"

He was slightly reluctant.

"Please?" I asked. "That costume is the reason I joined the sewing class. I think I need to reduce the waist. The buttons at the back are impossible without help."

"OK, Anne, if that's what you want, I suppose you can."

"Thank you, Derek. I'll make sure you won't regret it. You will need a fake bust to make it sit properly."

He looked startled by the idea of a fake bust. I got him to strip to his Y-fronts. I could see by the bulge in them that he was actually excited.

I had temporarily sewn padded cones of material into one of my old bras to give Derek some shape. I started with elbow length white satin gloves. Derek didn't seem to appreciate that a maid wouldn't wear gloves like those. I dressed him in a high necked blouse over that bra. The long cuffs buttoned over the gloves. He couldn't take those gloves off even if he wanted to. I tied the long pantaloons at his waist, added the under petticoat and the hoop -- he looked right, except for his hair.

It was a struggle to get the dress settled over the hoop which was probably just too large. I fastened the dozen or so buttons at the back of the bodice. The high neck of the blouse concealed Derek's Adam's apple. The dress's waist was several inches too large. We hadn't yet started on the full scale long aprons so all I had were the waist ones. I grabbed a white maid's apron to pull the dress's waist inwards. I knotted it tightly behind Derek's waist.

I asked him to walk up and down wearing that dress while I took pictures and more video. His head sticking out of the neckline looked wrong.

"Derek, I need to see the real effect. Hang on a second."

I produced a brunette wig styled as a Victorian maid would have worn her hair.

Derek shook his head.

"Please? This and a little make-up will show me how I would look."

I kissed him. That seemed to be effective. I kissed him several times.

"OK, Anne, just this once."

I lifted the skirt and hoop to sat him down on a stool. I worked as quickly as I could to apply minimal foundation, eyeliner and lipstick. I was surprised just how different Derek looked. Once I had stuck the wig to his head with double-sided tape Derek appeared as a very acceptable woman. He looked apprehensive and slightly worried as I recorded my handiwork.

"This was going to be my damsel-in-distress costume," I said casually, watching for Derek's reaction.

"Damsel in distress?" He queried.

"Yes. I like the idea of sometimes being a distressed damsel."

"How? This is just a maid's dress."

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