Jessica’s First Time

My experience is a bit scattered (as I imagine many stories are).

My absolute earliest memory of being intrigued by female attire (and why there was such a strict line between male and female clothing) was looking at my mom's heels in the closet when I was maybe 5 or 6 and looking at one blouse in particular. I think she mostly wore it during Halloween; it was a super shiny reflective silver top and I remember thinking how cool it looked reflecting so much light. All my shirts were dull fabric t-shirts.

Fast forward, oh maybe to age 14 or 15… My older brother had many girlfriends, and I remember trying on bras that were left behind; that didn't really thrill me much. Then this one time a girlfriend left behind an earring (couldn't wear it of course, just held it up to my ear and pretended) and a scrunchie (hair wasn't long, but I put it on my wrist as a bracelet which many girls at the time did when they let their hair down).

Then there was the holy grail of clothing, black nylons. I felt the fabric between my fingers. I wanted to try them on so badly, but I knew she was skinny and I was a somewhat plump kid. I didn't care, I had to know what they felt like. After putting them on I won't lie, I got excited. So much in fact that I "went" without even touching anything. I believe that ingrained my transgenderism, but more importantly my crossdreaming.

About a year later, my brother finally convinced my dad (parents divorced for a few years at this point) to let his girlfriend to move in. This was both a blessing and a curse. Blessing because I now had access to female clothing on a regular basis (a beautiful woman, in fact).

It was a curse because she too was smaller and I had to be very careful how I put things on. The worst sound in the world is stitching stretching until it makes that sound of cracking, which was the point where you take that article of clothing off, hang it back up and pray she doesn't notice. I remember a moment when she was arguing with my brother about how the washer and dryer was somehow ruining some of her clothes and stretching them out. I don't think I had felt more guilty up to that point in my life and to this day, I never confessed to it.

Of course, this only led to me wanting to acquire my own things. About age 17, I was entering local community college and had a part-time job while still living at home. I decided to acquire a PO box so things wouldn't be shipping directly to me at home. That way I could get female clothing catalogs like Lane Bryant and Fredericks of Hollywood delivered to a discreet mailbox and begin ordering clothing.

I could pick-up my order at the post office, walk into my room and hide them away. I had exciting moments in my life like anyone, nothing could possibly top placing an order for dresses and stockings, and then waiting the 5 to 7 days for those items to arrive. When it got closer to the time I thought it might arrive, I would stop by and check for a notice everyday (this was the days before tracking notifications to know when it was delivered).

I rented the smallest box I could get knowing if I had packages, they would store them in a bigger post office box for delivery. When my bag of clothes finally arrived, I rushed over to the box, opened it, grabbed the package and nervously put the key back in. I threw package on my front seat, not even opening it up to sneak a peek.

I arrived home, and my dad either wasn't home yet or he was sleeping on the couch like he often did since he worked third shift. I rushed into my bathroom, pulled that black dress out and excitedly tossed it over my head after I removed all my clothing. It was a cheap dress made mostly of nylon, but that shape hugging my body and giant flowing neckline in front was like nothing I had experienced before. It was probably on par with the first “oh.” It felt like a woman was wrapped around my whole body.

Since I had the typical bathroom with the giant mirror attached directly to the wall, I looked at myself and couldn't believe how just a dress could change my look so much. I remember getting weak-kneed and having to sit down on the toilet from excitement and just bending over with pleasure of how I finally got to enjoy this feeling for the first time in my life.

For years I collected all sorts of female clothing from bras, wigs, makeup, leggings, shoes, etc. I kept it all in a big cardboard box at the back of my closet buried under other miscellaneous boy things and my dad never found any of it.

To this day, neither of my parents know about my secret life. Only my wife knows my secret.

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 Polo.

Actor Patrick Stewart

Plan C

The dress I bought to wear to the Hamvention awards dinner was not compatible with any of the bras I own. The problem was that the straps of the dress did not cover the straps of my bra and the visible bra straps ruined the look of the dress.

Plan A was to wear the dress without a bra.

Plan B was to take the dress to my local lingerie shop and buy a bra that would work with the dress.

Then I came up with Plan C.

As you may or may not know, I am an Avon lady and while perusing the recent Avon catalog, I found something that might solve my problem: Body Illusions Seamless Smoothing Cami, which claims to smooth the midsection and back bulge and slim the entire waistline. It also had a roll-resistant hem and adjustable straps.

Its thin adjustable straps and $12.99 price tag sold me, so I ordered it on Sunday and it arrived yesterday.

Right after dinner, I tried it on. It looked too small out of the box, but stretched easily to fit and mold my full figure. That was all good and well, but would it work with the dress?

I slipped on the dress, zipped it up and examined the results in the mirror. After a slight adjustment to the cami straps, it was perfect!

I was so happy with the cami that I plan to buy another, as well as purchase a Body Illusions Bodysuit.

Wearing Cushnie Et Ochs dress, Sophia Webster sandal and Edie Parker clutch.

Celebrity makeup artist Andrew Sotomayor

Pondering and Wondering

In anticipation of my upcoming five-day stint as a woman, a faithful reader asked how my female voice practice is working out.

I think my voice is good to go, so I am practicing less than I did a few weeks ago. My main concern now is what I am going to say when I accept my award, not so much how I am going to say it.

***

If you have shopped online for womenswear, you probably get womenswear catalogs in the mail. I often wonder if my mail person wonders why I get all the womenswear catalogs, while my wife gets none.

Anyway, one catalog I receive regularly (like every two weeks) is the Woman Within catalog. I seldom buy anything from Woman Within, but I love their name. Since they sell sizes 12W and up, I am sure that the name is very appropriate for a significant number of their customers.

***

On WhoWhatWear, Bobby Schuessler suggested the following trick for walking in high heels without pain: run your feet under cold water (even if it's a sink in the bathroom), put a little hand lotion on your feet while they're a little damp, then put your stilettos back on. Just make sure you put your feet back in your shoes damp, not completely wet.

Bobby claims that you can get another four hours out of a pair of heels doing this mid-event.

And it works because the lotion seals in the moisture of the cold water and lubricates against any sore spots.

I' love wearing my heels, so I'll try this trick and let you know how it works for me.

Wearing A.L.C. Rhodes top, Intermix shorts, Star Mela Pelli bag and Joie Tonni sandals.

Male modeling the Denis Gagnon Fall 2012 Collection in Montreal.

Christina Marie’s First Time

Ah, the wonderful and fun 80’s!

It was in 1985 when I first thought about trying on ladies’ clothing. My oldest sister was getting married and I couldn’t be happier! I couldn’t decide if it was one less sibling in the house or the wedding gowns that were worn.

Come to think of it, I always loved going to weddings and seeing all the beautiful gowns the ladies wore. Lifting their dresses to reveal the most beautiful of shoes was always a treat for me as well.

With all the people staying at our house with us, my sisters and I had to sleep in other rooms. I got the pleasure of sleeping in a room my father and I built; it was then they started to shove all the wedding stuff into the room with me. I started to hate life until I started to rummage through stuff. And what did I come across? Shoes, beautiful high-heeled shoes!

I was curious if I could fit them, so one by one I tried them on. It sucked having big feet and not being able to fit in any of them, but then, success. I was able to fit my feet into a pair of 5-inch heels. I stumbled around a little at first, but then I caught on rather fast.

It was still a couple days before the wedding and I continued to put the heels on and walk around. At one point everyone left and I even got up enough nerve to walk around outside and into the rest of the house. Everything was fine until my dad came home. I slipped them off right before he saw me and he never found out.

The night before the wedding, my dad moved the wedding gowns into the room with me. I wondered what it was like to wear a dress. I had already tried the shoes, so what the heck. I remember it was really late at night when everyone was sleeping. I picked the largest dress and slipped it on along with the shoes. OMG it was such a rush. I just wanted to put on panties, bra, long hair and even more. Alas, I had to take off the dress and the shoes.

The next day was the wedding and I helped move everything to the church. My sister’s friend, who was to wear the dress I had on, asked why it was a wrinkled. I told her it fell on the floor and I forgot to pick it up. Well it did, after I took it off. LOL That started me off on my newfound femulating path.

In the following years to come, I tried different things like nylons, panties, bras, nightgowns and even a neighbor’s dress (another story to tell sometime). Nothing ever felt as good or as right as when I was in the wedding gown.

Finally, years later I got to be the bride with a wrinkled gown no less, and put on my favorite red holiday gown, too.

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 Blank Itinerary.

Actors femulating in the 1972 Australian film The Adventures of Barry McKenzie.

In living color, too!

Wearing Diane von Furstenberg.

Michael Andrews in a 1983 television movie Murder Me, Murder You. 

Everything you need to know about the transgender bathroom debate

"To paraphrase Denzel Washington’s character in Philadelphia, can someone explain this transgender bathroom controversy to me like I’m a 6-year-old?

"Someone needs to because nothing about the current debate is making any sense."

Gersh Kuntzman did an excellent job making sense of it in the Daily News. Please read what he wrote here.

Wearing Zimmerman.

Rocker Pete Doherty

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.