Carollyn's First Time

My life as Carollyn Olson has been quite a satisfying ride.

Over the last three decades, Carollyn has figuratively flourished and matured, and developed so many great friends. I would not change a thing.

My story is a little different than many of yours. I did not start dressing until 35 years ago and it was very accidental. To make a long story short, I can blame it on the cat.

I was home working on my spouse’s dresser when she was out of town. Our cat decided to jump into a drawer and damaged two pair of nylons. I was going to show them to my spouse and let her throw them away, but for some reason I put them on. Before I knew it, I was dressed in her clothes, wig and shoes. Oh, what a feeling!

By the next weekend, when she was once again away from home, I had bought heels, two dresses, pantyhose, and had studied how my spouse applied her makeup. I completely dressed and went out for the first time. The first time I really looked in the mirror, I could not believe how good I looked.

Where did I go? I drove to the local mall, walked around a bit, went in to a couple of shops, had a bite to eat and sat on a bench to watch other women walk through the mall so I could study their mannerisms and how they walked and talked. Was I nervous? Yes, a bit, but not overly. I was “passing” and enjoying myself. When I look back at that first time today, I still wonder how I did it.

Since then, I try to dress two or three times a month. However, I have had to be careful with my dressing (my wife is unware of my hobby even though she has dressed me twice for Halloween parties).

I invite all Femulate 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.

Wearing Polo.

Harvey Korman (center) on television's The Carol Burnett Show (circa 1972).

Both Mother and Father

A single Dad celebrates Mother's Day.

Wearing Madeleine.

Diego Ramos and Nico Scarpino on the Buenos Aires stage in Casa Valentina (2016).

Saturday Night Lives

Third Saturday of the month, we dine with our friends, Bill and Rosemary Lucas. We take turns, one month at their house and one month at our house.

Last month at our house, Rosemary and my wife Karen discussed how men can be self-involved. As an example, Rosemary went on and on about how Bill spent a lot of time and money on photography.

Not to be outdone, Karen mentioned how I spent a lot of time and money crossdressing.

I turned beet red with embarrassment. My crossdressing was a family secret. I was incredulous that Karen would let the cat out of the bag, but in the heat of the moment, she wanted to up Rosemary's complaints about Bill.

"Who would have thought that about Stanley," commented Rosemary.

"I'm shocked," said Bill.

"Yes, 'Stan the Man' likes to become 'Pearl the Girl' about once a week," added Karen.

"I'd like to meet her," Bill said with a Cheshire Cat grin.

With a twinkle in her eye, Rosemary suggested, "Maybe Pearl can dine with us next month."

"I think that can be arranged," Karen replied.

"I can't wait!" Rosemary exclaimed. The subject was dropped for other topics that I cannot recall because my head was spinning about what just happened.

On the way home, Karen apologized for telling Bill and Rosemary about Pearl.

"I accept your apology, but why did you go along with Rosie's idea about Pearl showing up for dinner next month?"

"At first, I thought it would be too embarrassing for you, but Rosie and Bill were so enthusiastic that I thought, why not. Pearl is a beautiful woman and she deserves to go out and be seen."

"I'll think about it," was where I left it.

The month passed and I thought it was a dead issue.

Over breakfast on the morning of our next dinner with the Bill and Rosemary, Karen asked, "What is Pearl wearing tonight?"

I didn't see that coming.

"Stan was planning to go to dinner without Pearl tonight," I replied.

"Rosie and Bill were expecting to see Pearl. In fact, I was expecting to see Pearl, too."

"But..."

"You are going to disappoint everyone. Why don't you stop being so self-centered and think about others for a change."

Karen was angry... very angry and I felt guilty and started reconsidering. Maybe it wouldn't be so bad. Bill and Rosie already know and it might be fun to get out of the house en femme, as the "girls" say.

I finally relented, "I guess Pearl can make an appearance tonight."

Karen's anger turned to elation, "Great! I'm so happy that she changed her mind."

I completed my Saturday chores by mid-afternoon and began transforming myself into Pearl.

I disrobed and applied hair removal cream on my legs, arms, breasts and as far as I could reach on my back. While waiting for the cream to do its job, I applied a shaving gel to my face, neck and armpits, put a fresh blade in my razor and got in the shower.

As the water washed the depilated hair from my body. I shaved. Then I cleansed my whole body, rinsed and stepped out of the shower.

After drying myself, I rubbed moisturizer into my soft skin, then I slipped on a pair of black lace panties (the only kind I will wear) and sat at the vanity to do my makeup.

I used some concealer to hide the faint shadow of my beard, then applied foundation and powder. I did my eyes next. The eyeliner makes them stand out and a deft application of mascara and eyeshadow make them look smoky and mysterious. Some blush and muted lipstick followed.

Pearl is a blond and has a variety of hair styles at her disposal, so I had to decide which coiffure she would wear. I selected a short wispy layered cut with flipped ends and dark roots that add authenticity to the wig. I slipped the wig onto my head, straightened it and finger-styled it.

I removed my undies from the bureau and pulled on a high waist panty girdle, while tucking Willy and his friends out of sight. Next came the matching long line bra and silicone breast forms that went into its cups.

Sitting on the bed, I put my pink-polished toes into a pair of suntan control-top sandalfoot pantyhose and worked the sheer nylon up my legs and over my girdle.

I slipped a black sheath dress over my head being careful not to smudge my makeup on the fabric.

Then I asked my spouse, "Karen, would you please zip up my dress?"

"Yes, honey," she answered. She stopped combing her hair to assist with my zipper.

"There you go," she said when she finished zipping me up and closing the clasp just above the zipper.

"Thank-you, sweetheart."

I completed my look with some tasteful jewelry: a silver watch on my slender wrist, silver heart clip-on earrings and my wedding band and engagement ring. Finally, I added a set of stick-on nails to my fingers.

I straightened out my dress and smoothed the hem, which fell about three inches above my knees,then slipped on a pair of 4-inch black patent pumps. A spritz of perfume on my wrists and on the nape of my neck, and I stand back to admire the finished product in our full-length mirror. Stan has left the building and Pearl was in his place!

I announced, "I'm ready," using a feminized version of my voice.

"You certainly are, Miss Pearl! I'm almost ready, too. Can you return the favor?"

Karen had just slipped on her green belted sweater dress and was waiting for me to zip her up.

"Sure thing," I said and I zipped up her dress.

"Check me out, honey, to make sure I look okay," she asked.

She spun around with her arms posed akimbo so that I could see any flaws in her ensemble.

"You look perfect," I said, "I am so lucky to be married to a drop, dead gorgeous woman." Then I spun around with my arms posed akimbo so that she could see any flaws in my ensemble.

"Perfect... I am lucky to be married to a drop, dead gorgeous woman, too," she replied.

We air-kissed each other so as not to smudge our makeup, grabbed our purses and walked to the garage.

Although it was only a half-mile ride to the Lucas home, Karen drove because I had never driven wearing high heels. Karen parked the car on the street and we walked hand-in-hand to the front door.

Karen rang the bell and we soon heard the clicking of high heels approach the door from the inside. The door was opened by a beautiful woman, who I didn't recognize.

Karen said, "Hi, Bill. You look lovely."

"Thank-you, but Bill's not here. Please call me 'Pamela.' May I assume your beautiful girlfriend is Pearl?"

"You assumed correctly, Pamela."

I was speechless. Pamela nee Bill looked fantastic. He was wearing a white jacquard mini-dress, off white metallic pantyhose, and silver strappy 4-inch sandals. His shoulder-length chestnut hair was up and his makeup was perfect.

"You look fabulous," I gushed.

"You, too, girlfriend. Let's take some photos!"

Wearing Caroline Constas.

Jerzy Grzechnik on Polish television's Twoja Twarz Brzmi Znajomo (2016).

A New American

Create, Adobe's online magazine, has an interesting article, The New Americans: A Photographic Exploration.

Inspired in part by legendary photographer Robert Frank, whose 1958 book The Americans presented portraits of everyday Americans and changed the way we saw our country, photographers Elle Wildhagen and Zachary Domes set out on a six-week road trip. Their goal was to present today’s Americans as they saw them: inspiring, hopeful, and “full of so much good.”

One of the new Americans they encountered was Jacob, who...

...made a strong impression on the pair: “It wasn’t just about Jacob and him expressing himself,” says Elle. “It was really about allowing anyone, however they want to express themselves, to feel comfortable and confident.”

Click on Jacob's photo in the article to view a video about Jacob. (You won't be disappointed.)

Wearing Rockins scarf, Equipment blouse and Theory skirt.

Tim Elliot on stage in Compleat Female Stage Beauty (2011)

Beth's First Time

I am guessing that my first dressing experience occurred early in my elementary school years, possibly first or second grade. I don’t think it was during my time in kindergarten, although it may have been.

Both of my parents worked, so I would get dropped off at my grandma’s house during school breaks including the summer vacation.

My grandma’s house was built in the '30s, and it was essentially a four square plan ― very traditional and classic. She lived in a traditional small lot neighborhood with a small front yard, slightly larger back yard. All the houses were lined up next to each other. Everyone had a front porch and a single car garage at the back of their property

.

There was a back bedroom, which I believe that grandma used as hers. In the bedroom there was a dresser filled with all sorts of slips and petticoats. All of them were white. Many of them were full-length slips. And this is what she wore on a daily basis under her dresses. This was circa 1962 lingerie; you get the idea of the type and quality it was.

To this day, I do not know if she encouraged me to try on her slips or if I did this of my own volition. However, my first clear memory of dressing is wearing one of her white full length slips. I still remember how strange and wonderful it felt. I remember her being pleased with how I looked. And I remember being disappointed that she would not let me go outside with the slip on to play with the other neighborhood kids.

Either during this first time I had her slip on or subsequent times, I distinctly remember being aroused. I will always wonder if my first arousal was due to wearing her lingerie. All I know is that this was the first time that I remember being aroused.

I really don’t know if my grandma allowed or encouraged me to dress on a regular basis. As I said, I was at her house all day for summer vacations. My guess is that my slip wearing at her house was infrequent.

I firmly believe that my path was established as a result of these positive and reinforcing dressing interactions with my grandma. I have a couple of full-length white slips and everytime I see them in my lingerie drawer, I have very warm feelings.

I invite all Femulate 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.

Wearing Ronny Kobo.

Winner of the Hancock (Mississippi) High School's 2016 womanless
beauty pageant Trevor Ladner, poses with brother, Trenton.

Tippi!

Sunday night, while I was switching back and forth between the Red Sox-Yankee game on ESPN and The Birds on Sundance, I recalled that growing up, Ted Williams was my idol. But a girl's got to know her limitations and I knew I would never grow up to be Ted Williams (who would?). But maybe I could grow up to be Tippi Hedren.

Was she gorgeous or what? The outfits she wore in her films were to die for. I wanted to dress up and be a woman just like her.

Ah, to be young and Tippi again!

Wearing Apiece Apart skirt.

A recent womanless beauty pageant contestant.

Alison's Weekend

By Alison, WA1YKL

This past weekend, I attended one of the largest Amateur Radio "hamfests" in the northeast. Its known currently as Nearfest, the New England Amateur Radio Festival, in Deerfield, New Hampshire It's a twice a year chance to paw over old and new radio and electronics equipment of all types, attend a seminar and meet many old friends.

Although I dressed primarily in "boy" mode, one ham who I met, also in "drab," must have taken notice of my long hair, pink nails, and long earrings. He carefully asked me if I was in transition. To which I replied,that I was only a "part timer." That was enough to break the ice and we had a very nice chat about the options for exploring gender identity and how this seems to becoming more common for those of us in the 50+ age bracket, including some hams!

I also had a prearranged meeting with another ham sister, Stephanie, who I had met recently online.  We chatted about our common interests in dressing and radio. I also invited her to attend a local Tri Ess meeting.

In addition to seeing all of the radio "stuff," I enjoy going to Nearfest as a way to reconnect with many old friends and colleagues, some who I have known for over 30 years.

On the second day, as the weather was much warmer, I wore a tee shirt with the First Event name and logo on it. While it didn't attract any mention from other sisters, it did not garner any rude comments from the mostly cisgender hams either.

Wearing Polo.

Peter Sramek on Hungarian television's Sztarban Sztar.

Brides Wear White

Wearing Alexander Wang.

Héctor Medina in the 2015 Cuban-Irish film Viva.
(Thank you, Zoe, for the heads-up about Viva.)

Proud Daddy

Wearing Polo.

Zach Villa (right) in the 2015 US film Honeyglue.
(Thank you, Zoe, for the heads-up about this film.)

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