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).

I wish it was me!

Femulating Taylor Swift

Back in January, I mentioned some YouTube femulation videos that impressed me. One in particular, by a tween-aged boy named Rowen, impressed me the most with his enhusiasm and reaction to his transformation; he thought he looked pretty and wanted "to stay like this." (I think we all can sympathize with those sentiments!)

The lovely Rowen is back with a new transformation video. This time his sister and cousin help turn him into (by popular demand) a near perfect likeness of singer Taylor Swift. I was impressed again and you will be too if you watch his transformation here. (I wish it was me!)

Wearing L'Agence.

Joseph Gordon-Levitt on MTV's Todrick.

Bullies

Throughout my school years, I was a target for bullies. I had a few things going against me that put me in their bullseye.

I was smart. I was always at or near the top of the honor roll and as a result, I was often the teacher's pet.

I was feminine. Compared to my male peers, I was a girly boy and was considered gay.

I was not athletic. Although I loved playing ball, I was usually one of the last to be chosen for a team.

The bullying subsided after I finished school and began working. Occasionally, as an adult, I would have a close encounter of the bullying kind, but most of the time, I was bully-free.

I assumed I would be bully-free for the rest of my life, but the bullies are back. Now they are trying to tell me where I can bathroom.

They claim that they have legitimate reasons to tell me where I can and can not go... to protect women and children in case I decide to become predator while I sit on the throne.

The trans-predator scenario never happened and never will. It is just a bully-sh*t excuse to bully because bullies got to bully and now they are trying to bully us.

 

Wearing Ann Taylor.

Grzegorz Wilk on Polish television's Twoja Twarz Brzmu Znajomo.

Herbert, Dagwood and Blondie

The parody ― National Lampoon Sunday Newspaper Parody, July 1978:

The real thing ― Blondie, #131, November 1959:

And Blondie, October 13, 2013: 

Source: Intermix

Arthur Lake as Dagwood Bumstead femulating in the 1941 film Blondie Goes Latin.

Twins Forever

Source: WhoWhatWear

Claire and John, circa 1915

On Sale Wherever Gaffs Are Sold...

Wearing Ted Baker London.

Audrius Janonis appears on Lithuanian television's Muzikinė Kaukė.

On the Road

This is the only photo I have of me and my Subaru. I must get more photos with the favorite car I ever owned.

I have driven my Subaru thousands of miles cross-country cross-dressed. My experiences as a woman driver were revealing to me.

(Funny story: After I purchased my Subaru back in 2007, a lesbian friend remarked, "How appropriate," because Subaru's are reputed to be the vehicle of choice among lesbians. I had no idea!)

• If I wear shorts or a short skirt or short dress when I drive, tractor trailer drivers will occasionally honk in appreciation of the view. Even though I am an old lady, I have had this experience more than once.

• No surprise here, but male drivers will take advantage of woman drivers. Men drive more aggressively when they cross paths with me. They assume that I will back off and give them the right of way, which I usually do, not because I am meek and mild, but because I am crossdressed. I do not want to get into an accident, then have to deal with civilians and police as an outed crossdresser, which showing my driver's license will clearly reveal.

•  Following up on the previous point, I drive legal as a woman driver. I closely follow all the rules of the road because I don't want to deal with police as a crossdresser. My understanding is that in my neck of the woods, dealing with the police is not an issue because they have been trained to deal respectfully with our kind. Beyond my neck of the woods, who knows? In any case, who wants to deal with the police respectfully or not?

• Car trouble as a woman driver is a piece of cake. You won't break a nail or get a smudge of car grease on your skirt fixing the problem. Being an AAA member is one solution, but instead of waiting for AAA to show up, just look helpless and soon a gentleman will stop by and do the dirty work. It happened to me once while shopping at a strip mall. When I returned to my car with my purchases, my car would not start, so I opened the hood to see if that would help. It did! Within minutes, two gents in a pickup truck pulled up, assessed the situation and determined that my battery was dead. They carefully explained to me how to start the car by popping the clutch and I was quickly on my way.

•   Passing is easy as a woman driver. Just use your turn signal to indicate what you are doing and when the passing lane is clear, speed up to enter the passing lane. After you passed, use your turn signal again and return to the travel lane. Seriously, passing as a woman is easier sitting inside your car. Tinted glass and reflections off the glass camouflage your appearance, so your are less likely to be read sitting in your Subaru. Waiting at a traffic light one night, a guy in the lane next to me rolled down the window on the passenger side of his car and tried earnestly to engage me in conversation. I ignored him, but I assumed that I passed especially since it was dark.

• During long roadtrips, you are likely to need to use a restroom. I have no fear about using the ladies' room in Connecticut because I know the state laws protect me, but I feel less comfortable using the ladies' rooms in other states because their state laws may not protect me. However, I will feel even more uncomfortable if I don't use the ladies' room, so I do what I have to do and have never had a problem. For what it's worth, I have successfully relieved myself in ladies' rooms in the following states: Connecticut, Massachusetts, New Jersey, New York, Pennsylvania, Ohio and West Virginia.

And so I go.

Wearing Elizabeth and James.

Artur Chamski on Polish television's Twoja Twarz Brzm Znajomo.

The Breakfast Club

By Paula Gaikowski

My dziewczyna Paula has been getting out a lot lately and she is dying to tell you all about it!

I had two road trips in the recent month and of course had time to get out as Paula

The first trip was to suburban Philadelphia.

When I am on the road, I tend to wake up very early, like 4:00-4:30. So I decided to organize my clothes and started trying on different outfits. Well I decided to get all dressed up with makeup and all – just as I would if I were going to be able to spend the day as a business woman. So there I am all dolled-up, and its 6:30 AM and the dining room is open, so off I went purse, laptop, looking very businesslike.

The waitress brought me coffee and addressed me as “Ma’am.” In one respect, it was remarkably mundane, however, the fact that I am out in the world doing everyday things as a woman is marvelously wonderful.

I truly want this every day.

I went back to the room and Cinderella morphed back into Cinderfella. I was so sad.

I must have missed some makeup because later that day one of my co-workers asked, “Hey, what’s on your eye?”

Thinking quickly I replied, “Oh, car trouble must be grease.”

A lady I’ve known many years quipped, “Yeah right!!”

I blushed and moved the conversation back to business.

I had nice weather in Long Beach, California the next week and decided to wear one of my skirt suits that I love so much. I loved my new glasses and had so much fun using my new makeup mirror that you can see to the right in the photo. Having a magnifying mirror made makeup application so easy.

I can’t stress enough what a help a mirror like this is! Please listen girls, the detail you get from the light and magnification is so helpful. It also solves the problem of putting on eye makeup without glasses. For once I could see in detail how I was putting on shadow and eyeliner! It’s lightweight and travels well; I use my hip pads to protect it in my luggage, at Walmart.

I had fun going to M·A·C and having an edgy young makeup artist teach me how to put on eyeliner the correct way. When it was all said and done, I was into it for $50, but oh so much fun and well worth the advice and experience of just being out there in Girl Land.

I bought a bottle of water at the front desk and had a conversation with the clerk, then went to the California Fish Grill and had dinner. While waiting to order, I could see out of the corner of my eye a guy about 45 looking me over, his gaze focused on my backside, then my legs.

“My gosh,” I thought, “He’s checking me out!” Whether or not I’m to his liking didn’t matter; just the fact that he is appraising me as a woman as a “possibility” is all it took for something to stir inside, something long hidden and forbidden coming to the surface.

I grabbed my dinner and walked out and felt my face blush.

Wearing Bebe.

Jack Clarke (right) of the Royal Canadian Air Force competed for the title of Miss Toronto, 1941. He was encouraged to enter the female beauty pageant by his squadron mates, who helped transform him into a viable competitor. (Source: One of the Boys by Paul Jackson)

My First Time: Stana in Wonderland

This is the first 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.

To kick off My First Time, I will tell you my own story.

My Self-Portrait

I was a renaissance boy.

Growing up, I was interested in many things and some of those things resided on the feminine side of the street called “Life.” My parents did not dissuade me from my feminine interests and my sister accepted my interests because it gave her an in-house feminine playmate.

So I thought that playing house was just as “normal” as playing baseball. And even though some of my peers let me know that I might be a “fairy” because of my feminine proclivities, I ignored them and happily skipped on board the Good Ship Lollipop.

And so it went until one day at the age of 12, I was home alone and heard a voice calling me. The voice was emanating from my parent’s bedroom. More specifically, the voice came from the drawer of my mother’s bureau that contained her intimates.

I felt like Alice in Wonderland as I opened the bureau drawer and my mother’s nylon s beckoned, “Try me!”

I carefully removed a pair of my mother’s nylons from the drawer and rolled each one up my prepubescent hairless legs just as I had seen my mother do so many times in the past. But something was missing.

When my mother put on her nylons, she finished by attaching each nylon to the garters of her panty girdle. My briefs did not have garters, so the nylons were loose on my thighs and slipping to my knees. I needed a girdle. Conveniently, my mother stored her girdles in the same drawer as her nylons, so I borrowed one from my mother’s stash and squeezed my chubby figure into it.

As I carefully attached my nylons to the garters of my girdle, I was impressed on how well the girdle shaped a chubby boy into a feminine figure. But something was missing.

Although I now had a nice figure from the waist down, my girdle pushed some of my body fat up over the top of the girdle joining up with my boy boobs to create an unsightly muffin top. This will never do, so I revisited my mother’s bureau and found the perfect solution: a long line bra. After I slipped on the bra, everything seemed to be in place and I opened my mother’s closet to look at myself in the full-length mirror hanging on the inside of the closet door.

Wow! I was impressed with the female figure that I saw in mirror. I thought I looked a lot like those women I saw in the Playtex and Maidenform advertisements!

As I admired the girl I saw in the mirror, I noticed the stacks of shoeboxes stored in the back of my mother’s closet. I did not hesitate as that voice urged me to go for it. So I searched through the shoeboxes and retrieved a pair of high heel pumps that I quickly slipped on and then revisited my reflection in the mirror.

Wow again! Not only did I have a figure that rivaled a shapely female, but now my legs were as shapely as any female’s!

After admiring myself for a few minutes, I decided that I better disrobe before someone came home. So I carefully removed all my mother’s finery and returned them to their proper place. But my Pandora had escaped and I would often return to my mother’s wardrobe to adorn myself as the girl I discovered in my soul.

Wearing Boston Proper.

David Castiblanco