Joanna’s First Time

My own first time was very late indeed. I was 24 and had a full-time job that I still have and my own flat. I had known that I wanted to crossdress for a long time, but had never done so.

As a child, I didn't see much difference in the girls I mixed with (though I was insanely jealous of their hair and dresses). My parents bought my clothes and took me to the hairdressers, so there wasn't a great deal of opportunity to express that part of me.

Also, my Mum's clothes were my Mum's, no chance of using hers, it wouldn't have been right. I did write stories about being zapped into a girl's body that dealt less with the physical changes and more with the wish-fulfillment. I find it interesting that none of them had the protagonist ever upset or simpering ― they were themselves as a girl.

In my teen years, I didn't even buy my own shirts because I was too scared of 'getting it wrong' so female clothing was out then, too. But I read about it and learned that it had a name, crossdressing. 

Around the age of 17 at university, I wore a pair of knickers for the first time that had been sent to me as a dare and to try and break me up with my first girlfriend by pretending I had a secret admirer. It didn't work, but I wore them a few times before finally throwing them out in disgust with myself. I had the biggest feeling that crossdressing was wrong, but without really understanding why. I struggled with this until I was 23. At this point I bought a pack of my own knickers (black and plain, full briefs) and wore them a few times to sleep and to make meals on an evening.

When I turned 24, a girl I liked convinced me to go back to her flat and try on a dress. It was a purple one with a corset-like bodice, scoop neck, puffed sleeves and a full skirt to the floor. I wore it over my actual clothes for the day and the girl tied the corset up in the back so that I couldn't take it off by myself. It was heavenly. It shimmered and flowed and I felt so right and at peace. It was a feeling I had never felt before. I could feel the skirt billowing, even though I wore jeans beneath, and the pull of the fabric on my shoulders (despite the shirt I wore). The color too ― it was soft and feminine and beautiful.

All the feelings about crossdressing that I had been struggling with for a good decade by this point seemed to melt away. I almost forgot about the girl I was with and when she told me to go and check out my reflection in the bathroom I did. She told me I suited the dress better than she did and, you know, I did feel that it suited me. I think she was being nice though ― she suited the dress better. My mind was in overdrive and my emotions all over the place. I couldn't think straight and I could barely breathe properly with the joy and the risk and the beauty of it all.

I was going to ask to borrow lingerie to fill out the top better, but my companion misunderstood my breathlessness and red face and asked if I wanted to take the dress off before the rest of her flatmates came home. She thought she was saving me from embarrassment and feared that she had made me do something I didn't want to do. I tried to stammer out that she was wrong, but it was too late. She undid the laces and hoisted the dress off me.

Afterwards, as we shared a coffee and I told her how I really felt in fits and starts because I just didn't have the vocabulary and was still trying to parse the whole sensation. But her friends arrived in the middle of this before I could ask to try again
.
For me, then, my first time was very late indeed, much later, I would wager, than most people who have crossdressed. But it confirmed in me that it wasn't really crossdressing, though I couldn't explain that at the time. I was so comfortable and happy in my own skin whilst in that dress that I instantly started buying clothing that would emulate that; starting a wardrobe that stayed small but lovely and remains now, though none of those original clothes remain (they were all purged when I was 29).

Now I know what I was unable to express at the time ― I was not cross-dressing, rather I was showing outwardly what I felt inside. I was presenting as myself for the very first time. In short, I was me. As a consequence, that first time remains wistful, hopeful and full of wonder. It is lost forever, of course, the girl and I shared a brief relationship and my next relationship ended in marriage. She does not approve of nor understand my feelings on clothing and so there are precious few opportunities to embrace who I am. I miss it.

I invite all femulators to share their first crossdressing experience. Try to recall that moment the first time you tried on a woman’s garment and began the process of unveiling and exploring your feminine self. To entice you to share your first time story, I will give away a free copy of my e-book Fantasia Fair Diaries to all whose stories I use in Femulate.

Wearing Metrostyle.

Jeremy Stockwell as Dinah East in the 1970 film of the same name.

Molly's First Time

When I was a teenager, I was dealing with a lot of conflicting emotions. Mainly, I really, really would have liked to dress like a girl.

I was a geeky boy, full of conflicting emotions. Sometimes I just wanted to try on a pair of panties, sometimes I wanted to sign up for full sex change surgery. There was no way I could tell anyone this.

It was the early 1990s and information on gender was hard to come by. I once waited several months to come by a copy of Caroline Cosey's autobiography. Then I immediately threw it away for fear of my parents finding it. I'd fantasize situations where I'd be 'forced' to play a female role, the hospital screw up where I'd get a sex change by mistake, the weird disease where I'd have to take massive dose of estrogen, the sneaky girlfriend who slipped hormones in my food, having to stand in for my (imaginary) older sister at her wedding. The list goes on.

But in 1992, the Internet came to my house in the form of a dial-up BBS (bulletin board system). For the first time in my life I could communicate anonymously and talk to people who maybe understood where I was coming from. At the age of 17, I came out to the local electronic world (the dial-up BBS only served one community).

Soon my prayers were answered in the form of a woman who was very sympathetic to my feelings. She said there was nothing wrong with what I was experiencing and if I was interested, she'd be happy to dress me.

Wow!

It wasn't long before I visited her house. She was a nice woman of about 30. After she sent her preschool son into the other room, she told me I'd make a wonderful girl and she'd be happy to help me on my journey. She offered to buy me clothes, take me shopping and provide opportunities to spend time as a female. She even let me try on some of her pantyhose. It was what I'd always dreamed of.

Except that her husband was there, too. And he watched us the whole time. He complimented me too, but in a way that made me feel very uncomfortable.

Afterward, they both e-mailed me. The woman mentioned how her husband was crushing on me (she was fine with this). Her husband was much more graphic about what he'd like to do to me. In retrospect, I'm lucky that didn't end badly. I never visited them again.

Also on the BBS, a friend mentioned (to my male persona) that some girl at his school was trying to find a date who'd be willing to go to homecoming in drag. I immediately told him to tell her I'd be interested (you know, as a joke). Two days later, I met a real life girl whom I hit it off with and told my friend not to bother.

The next year I was in college. I had freedom and privacy. Still I was too scared to contact an LGBT group. I just couldn't risk being found out. But the BBS’s came through for me again when I was contacted by a local crossdresser who told me about a local group for men who liked to dress in drag. He offered to take me along to the next meeting and to help me dress up. I went for it.

Chris was an extremely nice guy who made a very convincing woman. While I wouldn't shave my legs for the experience, Chris worked around that with dark hose. He did a phenomenal job with press-on nails, a wig, clip-on earrings, etc. He spent so much time on my appearance that he didn't have time to dress himself, so he escorted me “in drab.” as he put it. Going to a meeting (in a hotel conference center) on the arm of a man in his 20’s certainly gave me some interesting and exciting feelings.

It was thrilling at the age of 18, to be the youngest in a room full of gender-variant people. I was introduced as Molly (after my long time crush, Molly Ringwald). More than one person subtly asked if I was a genetic female.

A couple of months later I visited Chris again and this time we both went to the meeting en femme. I think Chris might have been romantically interested in me, but I may be flattering myself. In either case, he was a perfect gentleman and lady. Chris also introduced me to crossdressing fiction, which then was only available in printed form. Chris really opened my eyes to a lot of new experiences and I wish I could thank her again.

Sorry I do not have any pictures of Molly. She was a cute girl and I miss her.


I invite all femulators to share your first crossdressing experience. Try to recall that moment the first time you tried on a woman’s garment and began the process of unveiling and exploring your feminine self. To entice you to share your first time story, I will give away a free copy of my e-book Fantasia Fair Diaries to all whose stories I use in Femulate.

Wearing Nicholas.

Erik Handoko, male model

Donna's First Time

This another  installment of a new Femulate series in which I invite readers to share their first crossdressing experience. Try to recall that moment the first time you tried on a woman’s garment and began the process of unveiling and exploring your feminine self. 

To entice you to share your first time story, I will give away a free copy of my e-book Fantasia Fair Diaries to all whose stories I use in Femulate. 

Donna's story about her first time follows.

My sister was a few years older than me and when I was very little, I remember her dolls were so impeccably dressed, beautiful dresses, hats, stylish heels and purses. When I started getting GI Joes, I remember thinking how dull their clothing was, boots and khakis, and wondered how they would look in my sister’s doll clothing. 

Fortunately, by then my sister lost interest in her dolls and I discovered a treasure trove of their clothing. Well from that moment on GI Joe, regularly had tea parties (in war zones, of course) and fashion shows with all his friends. I remember James Bond with karate action was my best model!

After a short while, I wondered how I would feel in girl’s clothing. I remember vividly my mom’s pantyhose drying on the shower rod in the bathroom. After trying them on I was hooked! They felt so soft and smooth. 

The next opportunity, I also tried one of her girdles. I vividly remember the smell of clean lingerie and I loved how it hugged me. My mom’s bra did not fit, but my sister’s did, stuffed with socks or tissues. The finishing touch was her half- slip. I remember looking at myself in the mirror and feeling happy, really happy. You see, I grew up in a very dysfunctional, abusive home and really happy feeling were hard to come by.

I tried to put things away exactly as I found them. Looking back, I probably made a few mistakes but nobody ever said anything to me. Thank you mom, sis, GI Joe and James Bond (with karate action).

Wearing Valentino.

Gene/Jean Malin femulating in the 1933 film Arizona to Broadway.

It Fits

The dress I ordered online from Dress Barn arrived and fit perfectly. It is gorgeous and will be the dress I wear when I accept my award at Hamvention next month. I just have to decide how to accessorize.

Wearing BCBGeneration.

The 2016 Miss Koovagam Transgender Beauty Contest in Villupuram, India.

Marie Anne's First Time

This another  installment of a new Femulate series in which I invite readers to share their first crossdressing experience. Try to recall that moment the first time you tried on a woman’s garment and began the process of unveiling and exploring your feminine self. 

To entice you to share your first time story, I will give away a free copy of my e-book Fantasia Fair Diaries to all whose stories I use in Femulate. 

Without further ado, here is Marie Anne's first time story.

My earliest memories of dressing as a girl were wet days in the garage where we had a huge dressing-up box that included a selection of mother's discarded clothes. No secret as to what attracted me then, of course, the normal forays into my mother's wardrobe and underwear drawers when I was alone in the house. 

This was in the mid 1950's when foundations were well, restrictive stockings still with seams and full skirts, even for a 40-plus year old lady. Hats and gloves were there also, but underwear and dresses were the objects of desire. I guess then that I would also have tried on her shoes. She must have known, but nothing said. 

However, my most important memory dates from the time I was, I think, 17. I was with my girlfriend in her house with the rest of the family out and I asked with terrible fear, whether I could dress up in her clothes. The "Yes, of course," surprised me and she laid out a dress, took out panties and a matching black bra with some old balled-up stockings as padding, a suspender belt and stockings. My feet were too big for her shoes and there was no wig, but when I was dressed completely, she gave me lovely red lips and we went downstairs for tea. 

I was a boy in a dress, but, oh, what emotions! Guilt, awkwardness, pleasure all overloading my brain. Before her mother was back, the "girl" had gone and with this friend, never again. 

I would love to be able to tell her 55 years on, what a wonderful experience she gave me, but contact was lost years ago and she would probably does not even remember the incident. With another girl later the experience was repeated again, this time with a cheap wig and some make-up. Still a boy in a dress, but a little more of the journey to being a girl and then woman.

Now this woman occupies a fair amount of my wardrobe and is quite frequently out and about. But it has taken a long time, death and divorce included, but fortunately, supportive women friends.

Wearing Max Mara.

Joanna Lumley descends the staircase in the drag ball segment from the 1971 British film Lady Chatterly Versus Fanny Hill.

Probably the only cisgender female in this segment, Ms. Lumley plays Fanny Hill and imitates a man attending the ball as a woman! This softcore porn film also goes by the name Games Lovers Play and has little redeeming value. It is only of interest because of the extended drag ball segment. 

An amusing part of this segment has two policemen standing by as limos arrive outside the drag ball venue to drop off the attendees. When one particular limo arrives, a "girl" gets out and as she sashays to the entrance, she says in a deep male voice, "Good evening, officers." The policemen reply, "Good evening, Captain."

That's what brothers are for

Wearing Boston Proper.

Jeremy Lloyd descends the staircase in the fabulous drag ball scene
from the 1971 British film Lady Chatterly Versus Fanny Hill.

Amy's First Time

This is another installment of a new Femulate series in which I invite readers to share their first crossdressing experience. Try to recall that moment the first time you tried on a woman’s garment and began the process of unveiling and exploring your feminine self. 

To entice you to share your first time story, I will give away a free copy of my e-book Fantasia Fair Diaries to all whose stories I use in Femulate. Amy's story follows.

The first time I can recall dressing as a girl, is committed to memory like it only happened recently.

Our parents were out of town for a week and a good friend of theirs (an older woman) and frequent baby sitter was over and in charge. My older sister decided to dress me up and send me down the hall to the living room to give our sitter a fashion show. So with Nancy’s party dress, eyelet socks and patent shoes, I proudly marched into the living room to show the sitter. Of course she heaped praise on me and I ran back to Nancy’s room.

Another outfit was chosen and I was off down the hall a second time. I can still hear our sitter telling me how beautiful I was! I don't remember feeling the least bit embarrassed or naughty. I also don't remember our sitter being the least be apprehensive about our game.

I must have tried on several of Nancy’s dresses and skirts and the show was repeated in the following days. I also got to spend more time just hanging around the house playing "sisters" to the delight of my sister.

It was quite a week! Thus began a guilt free life of exploring!

Wearing Bebe.

Womanless beauty pageants are not something new. "Girls" were competing as far back as 1949
when this photo was taken at Cradock High School in Portsmouth, Virginia.

And shave your legs

Wearing Self Portrait jumper, Mercedes Salazar earrings and Alexandre Birman Keane sandals.

Ken Chan femulating on television's Destiny Rose (Philippines, 2015-2016).

Alison's First Time

This is the second installment of a new Femulate series in which I invite readers to share their first crossdressing experience. Try to recall that moment the first time you tried on a woman’s garment and began the process of unveiling and exploring your feminine self. 

To entice you to share your first time story, I will give away a free copy of my e-book Fantasia Fair Diaries to all whose stories I use in Femulate.

Alison was the first person to accept my offer and here is her first time story.

My first time wearing feminine attire was when I was about 10 years old.

I had become curious about women's lingerie after seeing pictures in the Sears catalog. My Mother would leave her freshly-washed clothes on a drying rack in a spare room. One night after everyone was asleep, I got out of bed and sneaked into the room where she had left her things to dry. Her bra was a fairly basic, Playtex Cross-Your-Heart (I think) type. Nothing particularly elegant. But when I picked it up and examined it, I was entranced by some magical aura that it had.

It took a few minutes to figure out how I should put it on, especially since it was way too big for me, (40C). I stuffed the cups with some tissues and it was just oh so special. I then tried on some of her panties that were hanging there as well. These were just basic, white nylon briefs, but they felt so much nicer than my cotton, boy briefs. Next was her slip. It was so soft and smooth as it draped over my body.

I repeated trying her things on many more times. I was always worried that I might be caught, or that she would notice something out of place. I guess that I was lucky as this never occurred, but this did mark the beginning of my life-long affinity for lingerie.

Wearing Alice + Olivia.

Coco Martin femulating in television's Ang Probinsyano (Philippines, 2015).

The Dress: Plan B

When I asked for your advice about what to wear to my big award's dinner next month, about one third of the suggestions advised me to dress my age and dress conservatively. And about two-thirds of suggestions were similar to Mandy's advice, "It's your night to shine...so go for it, girl! Rock that dress!"

I took the advice of the majority to to "go for it" and I ordered the gorgeous cocktail dress from Bebe that I had included in that post.

I had never owned a Bebe dress, so I did not know what to expect. Petra mentioned that Bebe dresses run small and that I should order my size and one size larger just in case.

The problem is that my size was the largest size they offered, so it was that or nothing. I figured that that size would not be big enough, but I would never know if I didn't try, so I went for it.

UPS delivered the dress yesterday and it was as gorgeous in person as it was in its photos. It was also a high quality dress and when I held it up to myself, I thought it would be a close call when I tried it on.

I got out of my boy costume and put on my waist cincher, a Spanx panty and a Spanx cami to smooth things out. I did not wear a bra because the style of the dress screamed "bra-less" to me.

I unzipped the dress, stepped into it and managed to zip it up about one-third of the way. There was no way that the zipper was going any further without damaging the dress, so I sighed, unzipped the dress and removed it.

Before I unzipped, I did look in the mirror and sighed again because I would have really rocked that dress!

I had no Plan B, so I began looking around and I am now considering the Dress Barn confection that accompanies this post.

Wearing Spiegel.

Ken Chan femulating on television's Destiny Rose (Philippines, 2015-2016).