A Cross Dressing Short Story

A Cross Dressing Short Story

1It was in 1969 that I first revealed my secret to another woman…. I felt I just had to. I had invited my boss’s secretary for a drink and I felt she would understand. I slipped her a couple of photo’s of myself dressed as Christine. Yes, she understood alright, although she said she would never have suspected such a thing of me! The next week she visited me at my home. This became a regular event when we would sit and sip sherry in a ladylike fashion. Soon I was showing her my large range of lingerie.

One day she asked to feel the material of certain undies I was wearing. I stepped over to the armchair in which she was sitting, and her hand felt the nylon slip and then ran up and down my sheer black stockings until she touched the crotch of my panties. I gasped as it had a sensational effect on me. “Nice?” she asked, as her fingers began to move slowly up and down, brushing the nylon against my now stiffening penis. Of course, she went on until I exploded in a wonderful orgasm, and that was the beginning of a relationship which lasted some years. Every time she visited, or I visited her flat, it ended up with her giving me a lovely orgasm. Sometimes she would be at me almost before the downing of our first sherry or whatever we may be drinking. I hardly had time to strip down to my nice undies before her fingers would close around and work on me until I was trembling at the knees.

As I backed off and collapsed in an armchair breathing heavily, I still wanted more. On days when she  was feeling rather sexy herself, she would disappear to my bedroom and strip off, she would borrow my black sheer negligee and re-appear beside me and we both pleasured each other.

One day she asked if I wanted to meet a woman friend of hers called Bea, Bea liked to watch other please each other and she also had a friend called Mary who liked to apply make to cross dressers.

The four of us meeting together for the first time was mind blowing and this happened once a month.

My wife knew all about what went on and was happy to turn a blind eye, our children had flown the next and she was happy to go to work each day, we lead a normal life really. I now have a wild circle of female friends and still like to flaunt myself in front of them.

Spanking Special – A Short Dominatrix Story

Spanking Special – A Short Dominatrix Story

Red plastic basqueEddy Walsh rang the bell on the door of the Mews flat. It was swung open by a young lady in her early twenties. Eddy’s eyes widened, she was very pretty and dressed in a most attractive maid’s uniform-grey satin dress with a short, flared skirt topped by a tiny frilly apron and French maid’s cap to match. “yes” she inquired in a Swedish accent. “I’ve come to service the central heating” Eddy replied. Ah yes, Madam said you would be coming, please come in.

Once inside Eddy looked round at the expensive furniture and decorations with some envy. He had been working on his own for only two weeks and was not yet used to going into other people’s homes. Please follow me the maid said, and she led the way to the boiler room. Thanks love, Eddy said, I will start on the boiler then check the radiators. Eddy thought about the girl as he worked. What a little cracker and quite friendly. He would chat her up a bit, then insist that she came with him to check the radiators. Once in her bedroom, well, he would see what developed.

DominationEddy was just about to call her when she appeared. You like some tea? She asked. Oh, please. We can have a quick cuppa and then you can show me the radiators. Yes, what is you name please? Eddy, what’s yours? My name is Olga, please follow. As they sat in the kitchen drinking their tea, they started to make small talk. I am aupair to Madam Hastings she explained. An aupair? But I thought that meant living as one of the family. Oh yes, madam is very kind. But you have to wear a uniform? Yes, madam insists but I don’t mind. It looks very pretty, no?  Oh yes, Eddy said, very pretty, indeed.

We look at radiators now? Right, come on. Eddy got up and his hand went to her well, shaped bottom. As he squeezed she nestled back onto his palm, wriggling slightly. Come on your naughty boy, she said. Err, how long is your mistress going to be out? Olga fluttered her eyelashes, oh long enough I think. Actually, Eddy didn’t care. This girl was asking for it and she was going to get it.

DominationShe showed him round the flat until they came to a very large bedroom which contained a huge double bed. Eddy checked the radiator, then straightened up. And now, where is your bedroom? Here Olga replied. You mean you sleep in that bed? Yes. But where does your mistress sleep? Here, she said again. You sleep together? Oh yes Olga replied smiling broadly. And does she………? Eddy started. Olga was young but experienced. Yes, she does but she is very gentle with me. Too gentle sometimes and arched her eyebrows. Eddie was over to her in three strides and pushed her back on the bed. Her hand went to his crotch as he grasped one of her breasts. Each had a hand on the other’s buttocks. Their lips met, and her tongue pushed its way into his mouth. He stopped and got up. What is wrong? She asked. Just getting my jeans off. Get your knickers down. No, no Eddy, that is your job she replied with a giggle. Eddy did not take long to do it and very soon his bare buttocks were jumping up and down between her willing thighs.

DominationEventually Eddy gave a deep sigh and lay flat on Olga. And just what is going on here? Said a deep contralto voice. Eddy looked up. In the doorway stood a tall blonde woman in a long red cape and red knee-length boots. Eddy jumped up looking round for his jeans. Olga gave a squeal and scrambled off the bed. Just who the hell are you? The woman asked. I, er….came to service the central heating Eddy replied. Instead you service my maid, eh? I’m sorry Madam Olga started. I will deal with you in a minute young lady. You, you little rapist, what excuse, if any, have you got? I didn’t rape her Eddy protested. She looked at Olga. He did rape you didn’t he my dear? Oh err….. yes, madam. I could not stop him. Well young man, do I ring the police or do I deal with you? Eddy as trapped and he knew it. Please don’t ring the police, he begged. We will see. Both of you get all your clothes off. Olga had stripped already. Go and get the twelve inch tawse, Olga, madam ordered. By the tine Olga returned, Eddy was naked with his hands firmly clasped in front of him. The pair of you, over the bed side by side, Madam ordered. Please madam, he made me Olga said. Silly girl. That story is for the police. Now get over.

Madam Hastings contemplated the two lovely young bottoms in front of her. She really enjoyed doing this. Six of the best each, then six more for him if he would not sign a full confession, and so on until he did.

DominationWhack, Whack< Whack, the strokes went on, reddening the bottoms more each time. Now madam said when they had each had their dose. You, miss, go and make my tea and you, young man, I want a signed confession, or you get six more. Eddy straightened up. But why? He said through his tears. You’re a good-looking young man. It will be convenient to be able to call on your services whenever I want to. There was a small desk and chair in the corner of the room. She plonked a pillow on the chair. Now sit down there and get writing…I will dictate.


Crossdressing Story

Crossdressing Story


WGS105It started when I was eleven years old, my fascination for girl’s clothing and crossdressing that is. I remember watching my older sister Katie walk around in skirts, dresses, blouses, all clothing that was infinitely better than anything I wore. It looked nicer, and when I hugged Katie, her clothes felt nicer against my skin, a lot nicer. There were times when I was left on my own in the house; my parents were either at work or out for the afternoon, and my sister was visiting her friends. I had freedom of the house, and since my fascination started, I had only wanted to do one thing: try on my sister’s clothing.

Many would have found it weird, an eleven year old boy wanting to try on girls clothing. I didn’t really care at the time, I didn’t know what kind of effects it would have on my future. At the time, when life seemed simple, I only saw it to be innocent curiosity that drove me to try on my sister’s clothes. I didn’t have any idea about the culture that followed it, I didn’t know that men and women dressed in clothing of the opposite gender as a lifestyle choice, I would find that out much later in my life.
When I entered my sister’s room, I had an idea of what it would be like. Pink, filled with girly things ranging from dolls to make up to posters of boy bands and actors. I was definitely mistaken. At the time my sister was sixteen and going through her GCSE’s. Her room was painted a cream colour, very few posters decorated the walls, shelves were filled with books and not dolls, and she had a large wardrobe up against the wall. That was my first port of call. I opened it up, and was stunned to see everything hanging up so neatly. My sister was a bit of a neat freak, everything was out of place, and it was rumoured that she could see from first glance whether or not something was out of place. I always believed that Katie had some sort of second sight for these things. It was proved right when I was first caught by her. Coincidently, it was also the same day I started trying on girl’s clothing.

WGS208When my parents and Katie had gone out, leaving me alone, I went into her room, and opened up Katie’s wardrobe. I was instantly drawn to the dresses. She had a ankle length purple dress with straps. Now on Katie, it would have went down to her ankles, but when I tried it on, it went down to the floor, and even bunched up leaving a small tail of fabric. It didn’t matter to me at the time; I simply stripped to my underwear and slipped the dress on over me. It didn’t even need to unbutton the back of the dress. I looked at myself in the mirror that was placed on the inside of the door. My green eyes staring at the figure in the oversized dress. I felt the satin against my skin, and I liked it. I still looked like a little boy trying on adult clothes though, I had short brown hair back then, my parents choosing my hair cuts and how I looked for my time at school.
I was going to take the dress and hang it back up to try on another item of my sister’s clothing when I heard the door open. Someone stepped inside, and I was unaware who it was until I Katie shout up to me.

“Rain! I’m home.” she called out to me.

I guess you are wondering about my name. Yes, I am called Rain. My full name is Rain Alexander Edmonds. My sister is Katie Elizabeth Edmonds and my mother and father are called Rebecca and John Edmonds respectively. I don’t know why my parents named me Rain, it wasn’t to do with the weather, I was born on Saturday October 20th, 1990, and according to my parents and sister it was a sweltering hot day so how Rain came into the conversation is a mystery.

Anyway, back to the story.

1When I found that my sister returned; the first thing that went through my mind was a close resemblance of the words “oh crap” ran through my mind. I still hadn’t changed out of Katie’s dress and my clothes were strewn over the floor. I was going to be found and instantly my mind told me to hide. I immediately jumped into the wardrobe, and closed the door behind me.
I remember that exact feeling when I was hiding from my sister. My heart was pounding, it felt like it was going to burst from my chest in a similar style to the Alien Quadrilogy. It would have solved some problems though, first off I would have been dead, and I wouldn’t have to face my sister’s wrath when she found I had tried on her clothes. She probably would have tried to resurrect my body and then kill me all over again for it.

“Rain, where are you?” I could hear Katie from outside the room, and I hoped she would think I was somewhere else. This was the moment I found my sister really did have a second sight. I overheard her muttering that she had shut the door to the bedroom before she left, and I foolishly left it open. She knew I would be in her room, and the fact that my clothes were left out for all to see didn’t help that. “Come on Rain, I know you are in here. If you don’t come out until the count of five then I will be forced to tell mum and dad.” she stated with a calm and methodical voice. Katie didn’t raise her tone, she didn’t have to.

wigKnowing that Katie would tell our parents that I had been hiding in her room was really the only contributing factor of actually giving myself up. That and if I had continued to hide in her wardrobe, any chance of denying it would be useless considering I had left my clothes out. She started counting down, and I knew it was now or face the wrath of my parents. They would never have understood it back then, but it was likely that they had taken it down to a phase in growing up. The old ‘curiosity killed the cat’ saying. They would have forgotten it, and just told me never to do it again. I didn’t even know how my sister would have reacted, but it didn’t matter. I had to come clean and so, I pushed open the door to the wardrobe, and shuffled out into plain sight of my sister.

For a moment Katie was quiet, she just stared at me. I was expecting her to start shouting and screaming at me, ordering me out of the dress and to get changed.

I was definitely wrong.

Katie hugged me. She stepped forward and wrapped her arms around me, a smile was on her face. I was dumbfounded, awestruck, amazed that I wasn’t deaf from the screaming and shouting that I had originally expected. She in fact explained to me that she had really wanted a little sister instead of a brother. I didn’t understand it at the time, but if I did fully take into account the words back then I might have been offended, but I knew she still loved me. Katie told me she was happy having a little brother, and when she saw me wear her dress, she actually liked it. Sure she was a bit annoyed that I tried her dress on without asking, but she didn’t let it overshadow the clear fact we had just come closer together. I explained to her my reasons, why I was wearing her dress and hiding from her. The fact that I liked the look and feel of girl’s clothing, and was curious to try something on. Katie asked me if I liked it, and I said yes. I truly did like wearing Katie’s dress, and I told her that I wanted to try more clothes on.
black and white studio photo of elegant naked lady

What she did next definitely surprised me. She took the dress off me and hung it up, instructing me to get changed into my previous clothes. When I was finished, Katie told me to follow her down to the basement. Now at the time when I was eleven years old, I had in fact been scared of the basement. My grandfather told me stories of monsters in the basement, and I’m ashamed to say that I believed him to that point.
It turned out that our parents had kept boxes of old clothes going back the years. Every outfit of value and importance was sitting in the cases. My first football kit. Katie’s first ballet outfit. Both mine and Katie’s school uniforms from school. Our parents had the odd habit of sorting things out into boxes with the ages written on, and it actually helped Katie with what she was doing. My sister brought out a box of clothes from when she was eleven years old. That was a great year, apparently. My aunt and uncle got married, Katie finished primary school, she performed the lead role in a ballet recital of Swan Lake, and there was the first family vacation, a cruise to the Mediterranean.
The outfits were going to be for me. Katie explained to me that she had always wanted a younger sister so that she could have someone to practice giving make-overs, and dressing up. Now that she had found out I wanted to wear girl’s clothing more, she explained to me that she was going to dress me up, and give me the make-overs she had wanted to give to a little sister. I was filling the shoes of being Katie’s younger sister, even if it was only at random dates and times. It would only happen when the parents were out. We would have started that day, but unfortunately our parents had returned earlier than expected. It didn’t matter to me, or to Katie though. It was the start of something new, a fun new experience that would bring us closer together as siblings.

A picture of a young woman resting her head on a towel over blue background

The first time we had together was the following weekend. Our parents had been invited for a ball in London. Katie had managed to talk them into allowing her to stay and look after me, without the help of our grandparents. During the week, Katie was only at school for half of each day and had a day off on the Thursday. During that time she went shopping, and she purchased a wig, along with a few essential supplies. The Saturday that my parents left, we got started. I found out about the wig, it was a blonde wig in the style of a pixie cut.
At first I was nervous of what was going to happen to me. The first chance to dress up had been going through my mind, it caused me to loose track of my school work at some points during lessons. My parents weren’t too pleased about it, but they just told me to pay attention at school. No one asked why I was distracted, something I was pleased to have avoided, but I could have easily used any excuse to get out of that. Luckily, the weekend came by quite quickly though, and soon, the Saturday my parents left for London came around, and Katie and I were left alone.
I thought we were going to start with what Katie called a ‘dressing up session’ straight away, but my sister had other ideas first. She told me to wait upstairs, and so I did. I sat for an hour playing computer games, at the same time I was getting anxious, I couldn’t wait to try on the clothes, and when the time came, Katie called me down to the basement.

Katie had been busy; she moved things around, creating two separate areas. The first area consisted of an old vanity table that had taken Katie a great deal of time to move out, and to fix the vanity mirror back on. It was made of white wood, and it had sat in their parents bedroom before they replaced it with the current vanity mirror.
On top of that was numerous articles of make up ranging from false nails to false lashes, along with lipstick, mascara, eye liner pencils and eye shadow sets. Various blush colours were ready, and the contributing brushes. Numerous foundation tubs were waiting with cotton wall pads. Next to the mirror, was a bust of some persons head made from marble. According to Katie it was a very expensive piece in which they had to be careful. (Little did we realise that three years later, my dad would only go and break it while taking it to be appraised and possibly sold on.)
TransgirlThe second area was for dressing up. A clothing rack of all the outfits I would be trying on had been set up, with a dressing screen and a basket to put the clothing I had been wearing at the time. Nothing was spared, Katie had thought of everything for what they were going to do. She had prepared bottles of water and glasses, a few biscuits and some snacks, she had even brought the phone down into the basement so that if their parents phoned like they said they would, then  we wouldn’t raise suspicion by being late to answer. (Our parents once scolded my aunt and uncle for not answering the phone by a certain time when they looked after me and Katie. It was purely because of the fact we had been sat out in the garden enjoying the sun.)

Transgirl“What do you think?” Katie asked as she watched me walk on towards the vanity table, and then walk onto the rack of clothing that she had laid out. Katie had brought her bridesmaid dress out, the white gown with the green sash wrapped around the waist, tied in a bow behind, and the puffed sleeves. A pair of green flats had been brought to wear with them.
A pink gown with a darker pink sash, a dark pink rose attached to the front of the bodice and two strips of satin to wrap around the arms was hanging behind it. That had been Katie’s gown when they went on the cruise.
Her school uniform: A red pleated skirt, white long sleeve blouse, knee high socks and a bow tie. (my sister went to an all girl’s school that gave her more ideas than just being a make-up artist, but we’ll get to that later.) Sitting at the bottom of the rack of clothes were a pair of black loathers that she wore. Quite cute, if I do say so myself. Slip ons with a bow at the front of both shoes.
The next outfit was a costume that Katie had purchased during the week of Belle from Beauty and the Beast. There wasn’t another outfit hanging on the rack after the Belle costume, but according to Katie she was going to try and dig some more out for me, just to give an experience of wearing clothes other than those of a formal nature.
I was both happy and nervous by that fact. I would have been happy with just trying on the outfits Katie had prepared before hand. I knew what was coming, but hearing the prospect of something new being prepared gave me a small feeling of dread in the pit of my stomach. I didn’t know what to expect. Still, whatever was going to happen was happening because I wanted it to. My sister didn’t have to force me, she didn’t have to use blackmail or threaten to tell the parents.

The first part of the dressing up session was Katie sitting me down on the chair and getting to work. Katie worked on the foundation, covering my face and correcting the tone of my skin. Katie certainly was an expert at giving make overs. While she worked, Katie explained to me that she had volunteered to help out at her school during the past year with the drama department, helping out with the make-overs for every actress that was performing. Of course it was kept under wraps because of our parents, but I’m thankful that Katie actually kept up her make-up practice.
Objects of Desire - Stockings and Suspenders

After about forty-five minutes of working on my make-up, I found myself looking like a little girl which I was stunned to see. I looked in the mirror and from that point on I was known as Rin (again, it’s a strange name, I know. My sister liked to read fantasy novels, she still does.) and I was Katie’s younger sister.
The next task for us both was to get me dressed. My sister took me behind the dressing screen where she… well I won’t go into detail. You probably get the idea of what happened. I emerged moments later in white girl’s underwear and a pink dressing gown. While I sat down and had a biscuit, Katie went on and prepared the first outfit. I was dressed up as Belle. Now that was a weird outfit.
Petticoats on first, all three of them. I could never understand how women could wear those things. The gown afterwards was made of satin, and actually quite comfortable against my own body. I was surprised it fitted me. While I was being dressed, my sister explained that she purchased the outfit for a twelve year old. It would be a better fit on me than that of an outfit for an eleven year old. I didn’t understand it back then, but as time went on I came to understand that every outfit was different in terms of the body shape. The body structure between men and women are different, and so that while costumes will be the same age, the shape of the female outfit will not always fit the male body. (God I hope that made sense.)
The outfit had everything; the gloves, the shoes, even a wig, though we kept that off as it looked completely ridiculous. I wouldn’t have looked like Belle. This wig was short, curled with ribbons in the hair and unfortunately very irritating. (Looking back on it, I think the wig was styled after the hair styles of Southern Belles of America and not Belle from Disney movie.)
The Actress

That afternoon, I relaxed and took the weight of keeping my crossdressing secret off of my shoulders. I was happy, thankful that Katie was there with me, talking me through the stages of getting dressed up, the fabrics used to create every outfit and what they meant to me. Katie explained everything.
Amazingly, I was expecting something a little stranger and longer, but Katie dressed me in every outfit, explained what it included, and why they were being used and what for. A lot of it I had a vague idea, I remembered the cruise and what my sister had worn was for the formal evening dinners. That was just one of the gowns she wore, and as much as she looked, Katie couldn’t find the other two evening dresses she wore, which, in all honesty wasn’t much of a problem. I had tried on numerous clothes at that point and there were other times in the future that Katie and I did similar activities.
Blue floral outfitThat weekend, I was stunned to be offered £50 to be dressed in whatever my sister dressed me in, and while I was expecting something very feminine and scary, it wasn’t too bad. During the rest of the afternoon and the evening, I was dressed in something similar to my sister’s old school uniform. A pink knee length skirt, white socks, pink trainers, a white long sleeve blouse and a denim waistcoat. That was before dinner, in which I was dressed in the bridesmaid dress that I had tried on a few hours before, and I slept in a set of baby blue footsie pyjamas. Amazing, one evening, a night and a morning of being dressed up by my sister and I earned £50 from it. I didn’t tell anyone about it until I was seventeen years old and part of a college LGBT group. It was discussed between myself and my friends.

The next morning, we found our parents wouldn’t be back until later that evening, so it gave Katie enough time to set everything right. She cleared all of the make-up, and I helped with clearing up the basement, even while wearing my sister’s chosen outfit. We got through the clean up, and I was back into my original jogging bottoms and t shirt by 4 that afternoon. Our parents returned an hour later, and they were none the wiser.

Dawn’s Transgender Story

Dawn’s Transgender Story

Most of the time Dawn lives as a man using a male name. However, she considers herself to be transgender.

Dawn, who works as an occupational health nurse on an oil platform, describes growing up as a boy who liked to dress in girls’ clothes. She hid that part of her identity when she was in the Air Force, but in recent years she’s become more open about her feminine side.

“As far back as infant school I remember playing with dolls and dressing in my sister’s clothes. I also remember feeling upset that girls wore skirts and boys didn’t.

“When I was about 10 or 11, I used to escape through the bedroom window at night and walk around town in girls’ clothes. Once, I got caught by the police and taken home. My mother then took me to see a psychologist.

“I think we saw the psychologist two or three times. At one stage, he asked me: ‘Do you want to be a girl?’ My parents were sitting with me, so I gave an answer they wanted to hear rather than the truthful answer. Looking back, I think if they hadn’t been there, things might have been different.

“After that, I kept that side of me hidden even more because it upset my parents. I kept myself as busy as possible at home, but the feelings never went away.

“I chose the name Dawn when I was about 12 years old. I wanted to be ‘me’, and my given male name didn’t have a female version. I thought for a long time before settling on Dawn.

“Dawn has many meanings: the start of a new day, or a realisation. But I chose it mainly because I like the name, and the few people I knew who were called Dawn seemed like nice people.

“I lived in a small town in Wiltshire with few job prospects, so when I was 16 I joined the Air Force. I became an aircraft mechanic for a short time before switching to nursing. That’s what I’ve done ever since.

“Back then, being trans in the Air Force was a big problem, so I kept it hidden. I found out about trans groups through other people and from newspaper articles. In the 1970s and 1980s there wasn’t much publicity, so you heard about it from agony aunts such as Clare Rayner and Marje Proops.

“While I was still in the Air Force, I visited trans groups in Bristol and London. It was an opportunity to meet like-minded people and to realise that I wasn’t alone.”

Meeting my partner, Jules

“In 1985 I moved to London and left the Air Force. It was the first time I’d lived completely on my own. As I was away from family and friends, I seriously considered transitioning [living full-time as a woman]. For nearly one year I dressed as a woman except when I was at work.

“Then I met Jules, my partner, an absolutely wonderful woman. I decided that my priority was to stay with her rather than transition.

“Shortly after we started going out together, we moved to the coast. Cornwall, our new home, was very different from London, and I hid my trans side initially.

“Only in recent years have we started being more open. I dress in women’s clothes maybe once or twice a week when I’m at home, and when Jules and I go to National Trust places, to the cinema or for dinner. But we generally do it away from our home town so that people who know us won’t see us.

“My two sisters know that I’m trans. My parents don’t know, or if they do know they haven’t said anything about it. Jules’ parents know. She told them when we first started dating, and I’ve been out with them dressed in women’s clothes.

“We try to tell people only if they need to know, but I don’t like hiding it. l’d like everyone to know and not worry about it, but Jules would rather keep it a bit quieter.”

Being found out at work

“Recently I was found out at work. I’m a nurse on an oil platform, and I was moving to another platform. Somebody emptied my locker for me and sent the contents to the next platform. People on my new platform also saw photographs of me on the internet.

“It was quite upsetting when I got a phone call warning me to be careful at work because all this information was out.

“I was expecting ridicule, abuse and possibly discrimination from the management team, but it was the total opposite. The management team supported me 100%, and the people who made a big fuss about it were taken off the platform.

“Being accepted at work was a humbling experience. My work colleagues’ support and relaxed attitude has made me feel valued and wanted.

“I don’t tell people that I’m trans. It doesn’t come up in conversation, and it’s not important to my work, but I don’t have to keep it a secret any more.

“Being a transgender person isn’t easy, although I’ve had an easier time than most people. I’ve had a lot of frustration. I’ve had to keep my feminine side secret, and I try to conform to what society expects. But now that I’m older, I feel more confident about my gender identity.

“I like to think that having a strong feminine side has helped me to help other people, which is good for my nursing. It possibly gives me a more caring nature. But as I’ve always been trans, I have nothing to compare it against.

“I know that if I were given the option, I wouldn’t like to lose the feminine side of my life. I wouldn’t be me.”



Nighties, whether designed to be worn by men or women, have been a first preference for all looking for comfort wear.  All across the world, nighties have been designed to be worn by women whereas pyjamas, trousers and shirts have been designed for men’s nightwear.

However, a handful of men all across the world have a passion to wear female nighties rather than male’s nightwear. Reason for this liking amongst men is the fact that the female wear is more comfortable and relaxing.

On the other hand, not all men, and a majority of females, do not like the idea of wearing nighties. Rather they prefer a pyjama’s or other men’s nightwear as nighties is not a socially acceptable phenomenon for men.

Therefore   a lot of people have a query of whether men can wear these nighties or not. One of the most commonly asked questions by many wives from all across the globe, and which can be found on almost every blog is whether their husbands can wear nighties or not?

Since my grandfather’s era men have stopped buying ‘Nightshirts’ which were a long soft shirt-like gown. My son wears a long oversized ‘T-shirt’ (or nothing). Since women wear pajama’s there is no right or wrong answer. The answer to this query will depend upon your own perception and your will to go against rather meaningless old fashioned fashion statements. Really, who cares in the dark at night.

Every individual has the freedom and the right to do anything and everything he wants to do.  However, a few people tend to follow these and do whatever they like, whereas some tend to follow the norms set by obscure people in the fashion industry and our nervous ‘Peer Pressure’ society and fail to break or deviate from those values.

Wearing of nighties by males is not socially acceptable but still a small minority tend to wear it. Furthermore, many females consider males wearing nighties at night sexier as compared to their looks in the men’s night wear.

The only reason for discouraging men from wearing nighties at night is the fact that it has been associated with females and has a distinct ‘Dress shape’ to it.
All these associations have been socially developed, and take great courage from men to be revolutionised.

Rainy Days – A Short Story

 Rainy Days – A Short Story

WGS208A few days ago, I received my new white mackintosh. I tried it on and immediately experienced the heady aroma of fresh rubber. It was a perfect fit, right down to my calves since it had been made to measure. I drew up the hood and tied the strings in a neat bow just below my chin, my blonde shoulder length hair showing just out of the side and forehead yet cosily tucked in from the elements. Being double breasted it buttoned up the front and fastened with a buckle belt. I stood admiring my image in the mirror, thrusting my hands into the slit pockets and did a twirl. Having hung the lovely garment on a clothes hanger and read the cleaning instructions, I left it in the bedroom and planned my next step.

I have a sympathetic lady friend who knows my secret, so I suggested we take the car to the canal and take a walk along the tow path. I’ll wear my yellow plastic mac because the weather forecast shows that’s its going to be a wet day, so we’ll need wellies she said. I wore my green wellingtons and she had on her black pair. I pulled up my hood and snuggled my hands into the inviting rubber lined pockets. The only thing we passed along the canal was the odd sailing boat or motor launch with their crews clad in oilskins. Beneath my mac I felt the firm control of the basque -corset that gripped my nylon tops tautly and over this I had on a slip directoire in peach, over which I wore a blue cotton polyester pleated skirt secured with a thick wide black plastic belt, lemon long sleeved blouse and a headscarf serving as a neck covering.


This outfit was topped by a roomy long sleeved bright button cardi that keeps your body completely dry, although there are vents in the mackintosh allowing the garment to breath. We hardly spoke because we were meditating on the peace and quiet of Mother nature. Later that afternoon we returned to my friends, comfortable new bungalow where I hung my wet mac next to hers. She made us tea after which I changed back to male attire. We might plan another day out in the rain and when we do I’ll let you know.

My First Bra Fitting

My First Bra Fitting

lingerie_interstitial_01I have agreed to do this but I am so scared, yes scared though my wife thinks I am being stupid. I have shaved and am smooth as can be, my makeup is perfect and I start to dress and know that I am shaking too much but she just laughs at me. I put on my panties and bra, adjust my bra to fit my breast forms perfectly and then slip on my carefully chosen cami “look, no one will know” my wife tries to assure me, but still I shake. I pull on my tights over my silky legs, and then slip into my cream blouse and smart knee length skirt and as I put on my business heels admire my painted toe and finger nails.

We go outside, it is a weekday so all my neighbours are at work, or at least I hope they are as I slide into the passenger seat of our car. Mt wife expertly drives us into town and through the maze of one way systems to the car park where I quake again. We get out, I have been out many times before but this is so different that even my wife cannot understand. We travel down in a lift to the shopping mall with a couple of oldies whose male member hold the doors open for us , “ladies” he says politely – it doesn’t reassure me.

We walk into the shop after much agonising on my part and much reassurance on my wife’s and we head for the underwear department. I stand nervously as my wife seeks out who we have come for and a matronly woman in a smart skirt suit appears and smiles and asks us “to follow me”. She takes us into the female changing area and asks us to take off our tops..I cringe and wish I could run away but stay and take off my blouse. For some reason I fuss over it, making sure it is not creased – why should I care at this moment?

braThe lady takes out her tape and expertly measures my wife’s bust and then notes to us all that she is a 36 D and then turns to me “madam would you mind taking off your cami?” she says smiling in that professional shop worker way. I panic but my wife smiles and nods at me and I decide to go for it and slip it off. Of course I have breast forms, of course even the most blind can see that they are not real even with my cleavage enhanced as it is with my diva bra but the lady, who I understand is called Jane, does not appear fussed in any way. She pulls the tap around my breast and takes her measurements and then says “madam, I suggest a 42 DD” and turns away, “I will be outside”. My heart is thumping as I dress but I also have a fantastic feeling in my panty area.

My wife and I dress again and go out into the shop where Jane walks through the bras in stock and recommends to both my wife and I the best type for our shape. As she packs my new bra and panties she smiles and says how much they will suit me.

A Transgender Poem

A Transgender Poem 

As I look in the mirror, who do I see

A reflection of the woman that I want to be.

Born into a body that fights every day

To keep all of my feminine feelings at bay.


Living my life as someone I am not

Lying and cheating, this has to stop

I have to be true, hold my head high

Be who I am, no longer have to lie.


Slowly and gently I take hold of the reins

To steer myself onwards, break free from these chains.

Achieving acceptance from family and friends

Each day is a bonus as my heartache now ends.


I now look in the mirror, who do I see

The reflection of the woman I wanted to be

Comfortable in my body, happy and free

When I look in the mirror, I just see me.

Crossdresser Story

Crossdresser Story

Ever since I can remember, I’ve been drawn towards femininity, from wearing my mum’s silk nightdress when I was just four, tottering around in oversized heels and making a colourful mess of my face at the dressing table. It was good, it was girly, it was me… but it was wrong, or so I thought! I was a boy, and dressing up with makeup was for girls. But it was also so very right for the crossdressing transvestite within me. So my anxieties didn’t stop me from my early experimentation, trying different lipsticks, playing with eye shadows and mascara, and looking on enviously as girls got to wear the clothes that I wanted to wear.

1The only girl’s clothes in the house belonged to my mum, and they were far too big: not right the crossdressing transvestite clothes for me. Even then I just wanted to feel absolutely right as a girl: truly feminine and stylish. I remember growing up not knowing anything about being a crossdressing transvestite. I just remember liking girl stuff. Then, I saw a film on the television: to this day I don’t know the name of the film, but it’s had a long-lasting impression on me. It was about a man, who met and befriended some crossdressers. It was set in the 1930s. He was ‘straight’ (whatever that means), and they slowly brought him into their world with a little peer pressure, bit by bit.

For him being a crossdressing transvestite started with a loan of a lipstick; he tried it, enjoyed it, and was a little turned on. When they met, they’d ask questions, and lipstick became mascara, blusher, eye shadow … he tried a dress for the first time, stirring those crossdressing transvestite emotions deep within him: it was exciting, now for heels, lingerie, the hair and nails … eventually, he was meeting his friends as a woman, he had ‘changed’ and it was natural. This moment was a life changing not just for the man in the film but for me too. I didn’t know other people felt the same; I hadn’t heard of a crossdressing transvestite before and certainly didn’t connect myself to being one. I needed to know more about this incredible world.

2These were the days before the Internet. The mere thought of being a crossdressing transvestite was taboo. Alone with only the memories of the film and a growing urge to become more feminine myself. But I wasn’t gay: I don’t fancy men. I was confused and didn’t understand. I always had a strange feeling of being a woman in a previous life, and drawn to a certain style of crossdressing transvestite clothes: long skirts, corsetry, long hair pulled back. Then I saw crossdressing transvestite adverts in papers: telephone numbers to call and speak to someone like me. This was too much to resist and I started calling other crossdressing transvestites just to chat.

I’d dress up as a crossdressing transvestite as much as I could, when my parents were out the house, and just enjoy feeling complete. Then as I grew up, and started going out with girls, I’d be dating the girls I wanted to be! My crossdressing transvestite dream girls! I’d be attracted by their hair, clothes and makeup, and at times, and sometimes even tried some of their clothes without them knowing.

I got a job and started earning money, but I couldn’t buy my own crossdressing transvestite clothes. I had nowhere to put them. All the time, I was still one of the lads, I had many girlfriends and I kept my crossdressing transvestite secret hidden. I suppressed it for a while.

3I got married and have a wonderful wife and a couple of great kids. I love them dearly, but I still have the same inner feelings! I now know so much more of this crossdressing transvestite world. It’s helped me understand that I’m not alone, and that it’s ok!! However, being a crossdressing transvestite is not something I’m willing to share with anyone – there’s just too much for me to lose! I’ve tried the occasional dressing service for a makeover. I’ve bought makeup and heels the occasional dress, and become my true identity ‘Cassie’ every now and again when I’m in a hotel overnight away with work. But I always get a guilty feeling, a thought of I shouldn’t be doing this. And when I look in the mirror, it’s not the same crossdressing transvestite girl that’s in my head.

I want to enjoy my crossdressing transvestite life; and it’s not hurting anyone if they don’t know! But it’s really difficult not being able to share Cassie with anyone! I’ve often had a fantasy of being kidnapped, and transformed into a woman against my will, and having to live my life out as Cassie: my delicious crossdressing transvestite dream! I’d stumbled across feminization hypnosis by chance, and saw a link to JJ at ‘Dress Me Up’. Well, my first thought was, “She’s absolutely stunning; she wears clothes that I could only dream about and her makeup is to die for.” I realised at that moment that I would have to meet her.

UND957Could she help me become the crossdressing transvestite girl I’d dreamed about my whole life? Could she help get rid of the guilty feelings and give me the feminine outlet for which I craved? I put it off a few times and then plucked up the courage to call. She so understood right away and made me feel so at ease on that first tentative telephone call, that I couldn’t wait to meet her and help find Cassie together. I booked a crossdressing transvestite appointment, and couldn’t wait to get there. I booked a day off work, but planned to travel overnight, allowing myself the luxury of going straight to a hotel after my visit.

I pulled up outside her apartment, my heart racing by this point, and called to say I’d arrived. I knocked at the door, and when it opened I met my JJ for the first time. She was gentle, supportive, understanding … and so completely sexy and appealing to all the senses: true sensuality with a wonderful clear-headed intelligence and fun-loving personality to match. We sat and talked about Cassie, who she was, what she liked, what clothes, makeup, look, feel, her deepest desires … I was in heaven, I haven’t been able to talk like this with anyone in my whole life, and I had four fabulous hours ahead of me. This was the start of my crossdressing transvestite dream becoming a reality.

lingerie_interstitial_01I stripped from my male clothes, and stepped into the crossdressing transvestite unknown. I was guided to the bathroom, a bathroom with candles, feminine scents, perfumes, and cleansing lotions and face masks, I was about to start my journey, the crossdressing transvestite journey to find out who I am, who Cassie is. After cleansing my face, JJ had run me a luxurious bubble bath. I climbed in. I’ve had bubble baths before, but this was different, my senses were heightened with the depth of my anticipation. JJ brought me a glass of champagne and applied a facemask, to deep cleanse my face for my crossdressing transvestite makeover: delicious!

I stepped from the bath, dried myself and pulled on a beautiful and feminine silken robe, stepped into heeled slipper and I’m sure I glided into the boudoir. This was genuinely intoxicating, and I felt so at ease, chatting with JJ as if we’d been girlfriends for years. As I sat in the boudoir, we chatted about the crossdressing transvestite look I was going for. I’m a girly girl, not a tart or diva, so wanted just to feel as feminine as I could. I’d asked for some false nails, I’ve always wanted long nails, painted … so feminine. JJ had bought some for me, but didn’t have any sticking pads, only glue … acetone was used to remove them later. Well, I had business meetings the next day and had to drive to London, I couldn’t run the risk of them getting stuck!

MOTORWAY FLIRTATION - A Short StoryBut, at that moment, I was becoming Cassie. The crossdressing transvestite atmosphere, the femininity of JJ’s boudoir and everything about the moment said do it, be as feminine as you can be, enjoy it and live with whatever comes, it was titillating, exciting. The rush of crossdressing transvestite adrenaline I had when I said “do it” was a moment that will live with me forever! JJ asked if I was sure, but there was no turning back I wanted so much to be a woman at that point being a crossdressing transvestite scared and excited me in one go.

As each nail was applied, and glued in place, I started to feel like a girl. I changed inside, I felt Cassie taking over, I can’t describe it, JJ kept winking at me, and I loved every crossdressing transvestite minute! My nails were on, and they felt like they were never coming off, we painted them, and my toe nails, and then it was time to apply my makeup. The feeling of having foundation applied, powder, eyebrows pencilled, blusher, eye shadow, eyeliner, mascara and then lipstick was my every crossdressing transvestite fantasy, I now felt like a woman. I had desires I’d never known before. I wanted my dress and heels, I wanted my breasts to grow, and oh, how I wanted to stay like that forever.

The Actress

And perhaps the strangest sensation of all: I wanted a man: I was a woman and it was utterly delicious. Being with JJ had allowed me to go beyond being a crossdressing transvestite into true femininity. Don’t ask me to explain! My time that crossdressing transvestite afternoon with my JJ was the happiest few hours I’ve had in a long time, and only JJ and I know about it. This is only the start of my journey to find Cassie, but it’s a journey I’m going to share with JJ. I can trust her, and she knows what I want, she’ll help me get there.

It was good, it was girly, it was me … and it was so right!

My First Time Visiting Bath

My First Time Visiting  Bath


I have been a secret cross dresser for many years but have only recently developed sufficient confidence to walk out in public.  Fortunately I have the support of my wife who has been a big help in getting the look right.  After much trial and error, I finally have an outfit I feel confident in. We both enjoy our occasional weekends away which combine a short out of season break with an opportunity for me to cross dress.

I have found that the easiest places to walk out are busy city streets in the early evening. The Christmas shopping period is particularly good because people rush about a lot and don’t take too much notice of passers-by. The city of Bath is an ideal choice because it bustles with shoppers and tourists and has many streets with interesting window shopping. The narrow pavements and cobble stones provide a real sense of satisfaction when walking in high heels but make sure the shoes are well broken in first!!

The  Saturday morning was spent on conventional shopping and used to acquaint ourselves with the layout of the roads and car parks. This is important because it gives confidence and helps minimise the stress of actually going out later in a strange area. Fortunately Bath has a large street level car park with many screening hedges which provides an ideal starting point.

At the end of the morning we returned to our lovely old hotel near Bath which fortunately has some rooms in converted stables. This make it easy to dress in the late afternoon and walk straight to the car in daylight. A quick glance is sufficient to ensure none of the staff are about. There is no need to worry too much about other guests as they are mostly out that time of day.

Once in the car we joined the anonymous local traffic for the return journey to Bath. The car journey is never a problem, as in the grey light of autumn it is virtually impossible to read a cross dresser through a car window. By the time we got back to Bath is was just going dark, but there were still plenty of shoppers about and fortunately a good selection of spaces on out chosen car park. After a few nervous moments we got out of the car to buy a parking ticket and then walked towards the shops.

I usually walk round with my wife not far away in case of trouble, but sometimes I walk by myself while she goes into a shop. On this occasion I had built up enough confidence in my latest outfit to actually risk going into a shop for the first time. We had selected Marks and Spencer for the trial run and my secret ambition was to try on a pair of shoes I had seen earlier.  The store was very brightly lit and I felt rather nervous. At first we stayed on the ground floor where there were many tall stands to give more cover. After a few minutes I felt more confident and we ventured upstairs to look at the lingerie. The upstairs was more open and had fewer people around  so I felt more exposed but still felt confident. I then wanted to try the ultimate test and visit the shoe department. As I headed along the open gangway to the shoe area I was immediately ‘read’ by a chap who was standing there waiting for his wife. He had the time for a long leisurely look and as I walked towards him he discreetly pointed me out to his wife. After a momentary glance at the shoes I made a rather swift about turn and headed back to the stairs and out into the safety of the street.

In many ways the chap in Marks and Spencer had done me a favour. The next day I felt strangely relaxed from the experience. At last I had tested my outfit and discovered its limitations. I am no longer hiding behind my own mirror image, but real world experience. I don’t yet know where the weakness is, but it gives me something to work on and an ambition to try and achieve a totally convincing look.


The hard part is knowing what to try next. I think I will invest in another Transformation Changeaway and try to pick up a few tips. Certainly the make-up could be further refined, perhaps a more feminine walk is required or maybe I somehow looked tense and did not smile enough. I think the real problem is to strike a balance between looking totally convincing, but at the same time sufficiently conventional as to avoid a long and searching look.

I hope my experience gives others the courage to walk out for the first time. Remember to use the crowd as your friend and to walk along with everyone else. The more people there are milling about the less conspicuous you become!!!!!