The Old Neighborhood

Susan's post on Sunday ("Not like other boys") inspired me to write this post today.

Growing up, I thought I was just like the other boys, but some of the other boys disagreed. They thought I was a "sissy," a "fairy," a "faggot," etcetera and the bullies did what bullies do.

I did not understand what caused them to treat me that way.

One day, an older neighborhood kid took me aside and said I needed to "man up" or I would continue to be the bullies favorite target. I shrugged off his advice because I still thought I was just like the other boys, so why should I do anything different.

When I went away to college, nothing changed except that there was a new set of bullies.

After I completed my higher education, I moved back home, but the bullies had moved on.

I moved out of the neighborhood 35 years ago and slowly discovered why I had such a hard time in the old neighborhood. I was really a girl in a boy's body and I played the part so well in so many ways that the bullies could not abide by it.

I will return to the old neighborhood in a couple of weeks. PFLAG is organizing a new chapter in my old hometown. The first meeting will be held in a church two blocks from my old home and right next to the grammar school where I was bullied for so many years.

It will be the first time in my old neighborhood presenting as a woman. How can I not go!

Alison Krauss

Michał Rudaś femulates on the Polish version of television's Your Face Sounds Familiar.

Boys Wearing Dresses

Yesterday's post, Sara's First Time, refreshed my memory about young boys wearing dresses in previous eras.

My mother put me in a very girly dress for my baptism, but after the festivities, she put my dress away in her cedar chest and that was the end of my publicly-approved days as a boy in a dress.

Two or three generations earlier, I would be en femme full-time until I was breeched. I wonder what effect that would have had on my penchant for femininity. I'm sure it would have intensified my feminine ways and make the transition to boy mode unbearable.

Anyway, when I first discovered that once upon a time boys wore dresses, I researched the matter to see how widespread it was (it was) and why boys wore dresses in the first place.

According to a piece by Judy Mercer Tescher of the Pendleton Historical Museum in Indiana, "It appears the original decision to place boy infants in a dress was a practical choice to facilitate wearing or not wearing a diaper. Extending the number of years that boys wore dresses is a larger story of societal change, philosophy, industrial and marketing forces, emotional needs and an array of other factors."

If you are curious like I was, I urge you to read Ms. Tescher's revealing article, "In History: Why little boys wore dresses."

Wearing Temperley London dress, alice + olivia clutch and Aquazzura sandals.

German boys and girl participating in Geschlechtertausch, 2016.

Sara's First Time

General Douglas MacArthur

At about four years, my mother on wash day would pile up the clothes on the floor for washing. I would go to the pile of women's underwear and play with them. Putting on the panties, bras, slips: both grandmother and mom would laugh! I was not allowed my grandmother's most fine items.

My mother was born in the same month as Shirley Temple and was a fan for a lifetime. Her favorite gifts as a girl were Shirley Temple dresses! Many times they asked if I wanted to try on the dresses! I really did! The ladies got into this from time to time and even went to the point of starting with panties and slips and going to full little girl drag.

One way they found of tempting, was my grandmother had some of her silk little girls panties, that after first trying them on they felt so nice and good, that all my grandmother had to do was hand them to me after a bath, and I never refused!

Once at age five, they did it and mom and dad had words over my dress which was uncommon, they rarely ever had a fight out where others could see! The next Saturday after my bath, my grandmother hands me the silk panties, which I took and it started, with a bouffant little girls slip, on to a blue dress with girl’s frilly socks and topped with patent Mary Jane shoes. These events usually lasted an hour. But this time grand took me and using an electric old style curling iron did my shoulder length hair into little girl curls.

From Colonial times to the early last century, it was common for boys to be dressed as girls up to age 5 or 6. My Grandmother was a fan of General MacArthur and General Patton, she collected books on them; after I started to read she went through them as a way to help me read, MacArthur had a picture of himself at five, and a picture of his family in 1930 with first him and then his son at the age of 5-6 both were in girls dresses with long curls!

The biography of Patton said that he was dressed as a girl to age eight and as a boy only outside of the family until age 10 and was not allowed to read till age 12.

After an hour my father called from the living room as I popped by "come over here little girl!" After several repeats, I did. Dad pulled me up to his leg and said do you like your dress little girl?
“Yes.”

Several other questions on my clothes followed, then he picked me up and set me on his lap and said "Little girl, do you want to keep wearing your dress for the rest of the day?”

“Yes,” I replied demurely. At that point he grabbed my head and kissed me on the forehead then pulled me into an embrace and snuggled; that I had seen him only give to little girls in the family! It was great! Total acceptance as I stayed there for several minutes! Till both my mother and grand came in from the doorway.

No more was said.


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 Marciano.

Johnny Downs (right) in the 1941 film All-American Co-Ed.

Marie, A Girl Continued

This story is a continuation of Marie's First Time.

Regrettably, next day when we were reliving the events of the previous evening my wife announced now that I had experienced some of the joys of femininity she now expected me to cherish the memory but we would never have an encore performance. I was inwardly crushed but I was able to obtain some photos from the party and cut one down to wallet size, which I kept for many years as a small reminded of my first fully feminine adventure. I would not be able until many years later after we had three children - all girls - learned many another aspects of femininity. Was surrounded by this crew until the girls departed the nest and my wife suddenly passed away. Shortly afterward the girls came and cleaned out all my wife's things and I was left with an enormous walk-in rosewood closet with a full length beveled mirror and the delicate fragrance of her numerous flower caches. This started me into on exploration of my femininity, which had been dormant for twenty-four years.

During the next few weeks I recalled all the preparations for the Halloween Show Girl Team and mentally relived the preparation and the excitement and thrill of that evening in my mind. Without my "Girl Guide Partner," my first purchases were tentative and always mixed with other purchases. It took a few trial runs to determine my girl sizes (36B, eight in panties and skirts, and ten in dresses and twelve in well tailored ladies suits (skirts had to be taken in). The lingerie collection gradually grew to become came a rainbow of matching colors. The same with shoes and purses and of course a few good quality wigs. Although I had the run of the house and could do the housekeeping chores a la femme, and could walk outside on the two acres of property and travel down the driveway to deposit or pickup the mail my inner soul yearned for some female companionship and appreciation as well as makeup tips and feminine training. I was yearning to go out into the world and experience the life I had forgone those many years. The "web to the rescue."

It took me a few weeks of frustration and missed starts before I came up with my "Fairy Godmother." Finally after several weeks/month of searching under various terms, located the website of a makeup artist who also does photoshoots a few hours away. Made an appointment and began preparations including culling my wardrobe and purchasing a special outfit. On my arrival day, I was met by the "artist," an extremely friendly and lively woman who shortly I would learn was totally understanding and highly supportive of Marie. I was thrilled but also a little anxious as I entered this new world.

After a few minutes of chatting with a glass of wine in hand, I began the conversion from Bruce to Marie. Shave, shower, dusting powder, wig, lingerie, and dressing gown followed by a full professional makeover. Then we selected the outfits beginning with casual walking-out togs, moved to day dresses, then a stylish business suit, a wonderful cocktail number all with the appropriate jewelry, accessories, shoes and purses. There were camera shots galore, some posed but many candid as Marie transitioned from the casual afternoon shopping outfit through each of the progressively for feminine images.

I was in seventh heaven as someone coined ages ago. We eventually graduated to an off the shoulder low bodice ball gown worth matching shawl. Did I tell you the background music during the journey evolved to match the mood setting of each outfit. Totally enticed by this new and wonderful world changed back to a nice up-scale shopping outfit and departed for a light dinner at a warm, friendly and cozy restaurant. The three of us – my artist’s husband had joined us for dinner. Then a walk along the lakeside boardwalk with the evening breeze gently blowing my skirt and caressing my well rounded breasts with just a touch of cleavage showing. The clicking of our heels was the musical backdrop. The night was not over!! After Brad – the husband went back to work, we girls headed back to the studio and another whole chapter of delight and femininity awaited, although I was unaware at the time and due to the trance of euphoria I was in. Nothing could be better, I thought. I proved to be delightfully incorrect.

Upon pulling up at the studio my "Girl Guide" suggested I take a leisurely "soak" and she would be back in 45 minutes for another training lesson. Before ascending the stairs to her house, she chirped over her shoulder that I would find everything a lady needed in the bath off the studio and available myself of anything and everything I found finishing up with the reminder she would be back in 45 minutes and expected to fine a perfectly smooth skinned and moisturized “Marie” waiting for another chapter in femininity. With cheerful directions I slipped off my heels dangled them in one hand and with purse in other and flew up the stone steps.

As I entered the bath-suite, and that was what is was – the lights slow came on and climbed to a pleasant pinkish hue and soft music filling the air. I was stunned and captivated. Taking one last-long look in the full-length wall mirror, I carefully removed the walking-out dining outfit carefully hanging it on a cushioned and perfumed hangar. There were several. Each displaying a separate article of intimate apparel, including a short pink dressing gown, and a black satin sleeping gown and matching black negligee. Next to this mini-alcove was velvet covered cushioned stool. On it laid a black bra and panty plus a pair of near black thigh highs. The tub had been half drawn and the water was barely warm so on with the hot water tap and then in with the bottle of bubble bath that was perched on the side. While waiting a quick face cleaning and shave, then slide into the foaming delightful smelling blue liquid. There was a small book title “How to be a Girl.”

Only a quick perusal was allowed as only 20 minutes were left before my hostess would return. Gingerly, I stepped out of the porcelain tub and using the giant sized pink bath towel, dried and powered my smooth skin paying particular attention to my shoulders, throat and cleavage area. Then on with the lacy bra and equally lacy panties followed by carefully rolling the thigh-highs up taking special care not the cause a run in these gossamer encasements. Then the black heels and the thigh-length dressing gown.

Just as I was brushing my hair, I heard the chimes from the studio door and the cheerful voice of my hostess calling my name, "Marie, are you decent?" I quickly chirped back a positive reply and entered the studio and took a sit in the makeup chair where my face again become a palette of femininity and if I may say so, when finished glamorous.

As I stood in front of the full-length mirror, once more my hostess came behind me, wrapped a black satin and bone corset around my waist and began working the laces. She had me turn away from the mirror as she was performing this piece of magic. When finished, she added a pearl necklace, matching dangling earrings, ring and bracelet and a cloud of perfume from the crown of my carefully casually brushed hair down to my now naturally-enhanced cleavage. Then I was allowed to gracefully turn back to the mirror which she had now opened to it three full panels. A vision of femininity in spirit and body looked back. I was flabbergasted at the level of artistry my hostess had achieved and absolutely taken back by Marie.

Lastly, I was guided to a nearby bed and directed to strike several girly poses, while my hostess snapped pictures in a rapid suggestion. She then exited the studio and turning off the light, wished me a night full of wonderful dreams. Luxurious in the memories of the day and evening, I drifted off to a restful sleep.


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 Alexander Wang.

Hans Anton, professional femulator, circa 1910

Marie's First Time

My recollections are mixed about when I discovered/suspected I was not all male or should I say, had some female hiding in my inner core. My first positive but fearful incident occurred at about age 12 or 13 when one day I discovered my nipples were suddenly hard and sore and had a pronounced bud of perhaps a quarter in diameter, which was tender to the touch. I was terrified – am I turning into a girl? After a week or so, all the sensations and buds receded and I continued life as normal.

At about age 16 several things happened. Almost every day I walked past an upscale dry cleaner who usually had several ball gowns on display in the window and I found myself admiring them.

My movie heroes were John Wayne’s portrayals in westerns and war movies, but occasionally, I saw a Technicolor musical. Often these starred glorious women like Debbie Reynolds, Lana Turner, and Elizabeth Taylor. I always was fascinated by the delicious-looking clothes and in particular remember one scene in Cat on a Hot Tin Roof where Elizabeth Taylor was wearing a body-clinging slip. I thought that was fantastic and began to envy women for their ability to wear the clothes that looked great and offered freedom of expression and mood in sharp contrast to the dull drab colors and styles of men’s attire.

My next shocker came at summer camp where everyone wore shorts. My first day there I put on the uniform and when I stepped out of the tent, I got some whistles and comments from several girl campers about my great gams, which were “too good for a boy.” Was I embarrassed!! But I cataloged the incident in my brain.

The next adventurer was self-induced. While baby-sitting for a relative, I discovered an evening gown – probably a bridesmaid’s – hanging in the hallway in a pink plastic bag. Carefully I raised the plastic and found a gorgeous green velvet floor-length gown with a princess neckline. I was drawn to trying it on. Quickly I took in into the spacious bathroom, took a very quick shower, then stepped into heaven and zipped up the back. My cotton boy socks filled out the bodice wonderfully. The off-the-shoulder style added a degree of daring and romance. It reminded me of Scarlet O’Hara in Gone With The Wind and her gown made from the living room draperies.

I was ecstatic, but after a few twirls in front of the full-length mirror, I was seized simultaneously with near euphoria and panic. Quickly, but very carefully I unzipped and let the green velvet cloud slowly slide to the floor, where after gracefully stepping out of its warm circle, I very gingerly hung it up, covered it in its plastic protective cocoon and returned this marvel of femininity to its original position.


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 JustFab.

An all male cast performs Guys and Dolls at the UK Caldicott Prep School in 2015.

Tricia’s First Time and Beyond

My earliest memories of crossdressing are circa primary school days.

There was a trunk full of women's clothes in the garage of our home and I remember enjoying getting the dresses out and putting them on. My Mother also had an old one-piece swimsuit she kept in our laundry and when she was not home, I'd go in there and try it on. I think I can also recall donning the swimsuit and a wig for a "dress up session" with one of my male cousins who dressed as a beatnik, all this in front of some relatives. Yes, it was that long ago! Worse still!!! ...about that time I found an encyclopedia article on women's period dress quite fascinating, so I guess my love of wearing women's clothes stems from that time.

I can also clearly recall how beautiful my Mum looked when she and my father were attending a formal ball and I guess I wanted to look like her: all beautifully coiffed, perfumed, made up and dressed in a long evening gown. Perhaps that's where my ongoing love of formal wear came from too!

Moving to my early teens, my parents had a holiday cottage where, though it would never be allowed these days, I refused to go for winter weekends as there was "nothing to do." So this gave me the chance to be on my own and dress in all my mother's finery. Tennis balls had to make do for breasts in one of her bras, but that was OK. I especially enjoyed the tightness of her panty girdles and feeling the tautness of the suspenders attached to her stockings.

This went on for some time until, inevitably, some relatives called in to check on me one night and I was well and truly "sprung." Being a typical "father of the age," i.e. the 60's, my father's "severe talking to" about this "hobby" of mine centered on the retribution I would face when I got older if the "boys in the pub" found out about my penchant for things feminine!

A Lady Bracknell femulation in a North Carolina private school production of The Importance of Being Earnest.

I attended a trade-oriented, all-male high school where drama and plays were hardly given a mention. So it can only be imagined how jealous I was when I read a newspaper article about how in the best tradition of all-male private schools of the era, boys were selected to play the female roles in the school's annual production. Males playing Lady Bracknell in the Importance of Being Earnest have had me green with envy ever since!

Onwards into my 20's and once married "this will all fade away." But of course, it did not and the need to be Tricia caused much tension in the marriage and eventually was one of the main reasons for the divorce. Siring two girls did not help because when they matured, there were even more "frillies" about the house!

My career involved a lot of interstate and overseas travel so that's when Tricia would appear, mostly in a hotel room somewhere. Though she did venture out occasionally in such places far from home as London and Toronto and a couple of crossdresser group meetings in Perth, Australia, she's been retired for quite some time now and the location of where she lives and the circumstances of that location, plus her current relationship allows Tricia reasonably frequent occasions to "emerge." Period and evening gowns are still favorites, as is classy cocktail wear and lingerie.

Tricia would love to go out in public more often, but not in the small rural community where she resides. The gossip mill would go into meltdown if she was "sprung" and whilst she may be able to withstand all of the above, the burden on her beloved partner would be most unfair!

Furthermore, Tricia knows that one day, hopefully quite some time away, "advancing years' will decree a move to a retirement village back to the City. How this will affect not only her but her clothes, makeup, jewelry ,etc. wearing and storage remains to be seen.

Happy dressing everyone,

Tricia

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.

Jerzy Grzechnik femulating Adele on Polish television's Twoja Twarz Brzmi Znajomo.

Carollyn's Other Times

This is part 2 of "Carollyn's First Time," which I posted here on Monday.

Skipping to October 2004...

My real life as Carollyn started on the 17th of October. My wife and family went to Disneyland while I had to stay at home. For six days, it was feminine bliss. By that time, I settled on my name, my overall look and style.

That week, other than work, I lived as a woman. It was wonderful. I went to movies, dinner, shopping, the casino and did many other "girlish" things. I was never harassed and was always accepted as a woman.

I had been using my wife's short wig, as my second-hand wig was "big hair" and I wanted a change. I visited a nearby salon where I had purchased my first wig. The ladies at the store were so helpful, especially Linda. She took my "big hair" and trimmed it into something more stylish.

I had first gone to the shop in male persona, but the girls insisted I come back dressed when I picked up the new hair. Unfortunately, the day we set for my return, my wife had to cancel her plans, so I would not have an opportunity to dress. I phoned the ladies at the shop and told them of my dilemma and they insisted that I dress there. So I did, and spent four hours with the ladies in my new hair while learning etiquette from one of the ladies who was a former model. I felt I was all set until a few months later.

The following May, I had the luxury of making a trip to I Love It Girl (ILIG) in Fremont, California. ILIG was a TG paradise with tons of clothes, wigs, shoes, etc., and a lovely and helpful owner in JoAnn. I was on a business trip to the San Francisco Bay Area and decided to visit on a non-social night. (ILIG has Wednesday night socials every week).

When I arrived, JoAnn was busy, but greeted me with open arms. I was dressed in a red skirt outfit and matching heels and she gave me so many compliments while she worked with another client. After a short time, she sat me down and chatted about dressing and then without asking my size, pulled out a number of different dresses for me to wear for pictures. For what seemed to be hours, I played dress-up with her help and we took numerous pictures.

Close to midnight, I drove back to my motel dressed, but with a new hair style and a new attitude... and total confidence. I was a woman. I even went to dinner the following evening to a fancy hotel restaurant as Carollyn.

During the next few months in 2005, I met a friend, Linda Holmes, who moved to my area from Maine. We got together numerous times to dress and go out on the town during the day for lunch, shopping and lots of pictures. Linda was about two years into her transition. She was a sweetheart and the co-founder of Mature Women Group.

My salon friend, Linda, recommended I change my hair style to what it is today. She told me that my current style makes me look 10 to 15 years younger.

In November 2005, I received the first "shock" of my life. I had been a member of URNotAlone and VickiRene.net, but my good friend, Lauren Phillips, nominated me for the prestigious Vanity Club. I applied with some hesitation concerned that I would not be accepted, but I received enough votes to become a member.

My second "shock" occurred in March 2006 when KC Tyler selected me to be a member of KC's Top 10. KC's was the first TG site I found on the Internet. I never thought that I would become a friend and a member of her equally prestigious site.

Now, we must jump to Christmas and New Year’s...

I decided to be daring! I had never worn a formal dress except at ILIG, so I paid a visit to my local JC Penney's and "borrowed" a red chiffon formal and a black party dress. My desire was to take pictures and send e-mail Christmas cards to my friends. So, in male persona, I made the purchases and one evening prior to Christmas, I dressed in a long red strapless formal and took my pictures. A few days before New Year’s, I wore a black strapless party dress. Both dresses were so great to wear and I felt so good being dressed "to the nines."

A week after New Year’s, I was back in the Bay Area and another trip to ILIG. I took the black dress with me and JoAnn flipped when she saw the new "complete" product. After a little touchup of my makeup and a few accessories, we took tons of pictures. I stayed for four hours and wore a couple of other dresses JoAnn had selected. Had I had the time, I would have stayed into the night. I drove home dressed and stopped at JC Penney's to return the black dress, as I had no place to wear it again. Sigh!!!

Life as Carollyn has been fabulous. I love dressing as often as possible and enjoying life as a lady. When I dress, I want to create an illusion of a classy, perky and joyful conservative woman. When out, I want to honor women and blend in with others without drawing attention to myself.

I strongly want to help other girls and that was one of the reason the now-deceased Linda and I formed the Mature Women Group ten years ago. I don't consider myself an expert and blush when others consider me an icon in the community. All I want to do is assist other girls and walk hand-in-hand with them on the same, wonderful journey I'm taking.

Wearing Bebe.

Logan Kesler at the 2011 Theatre Under The Stars' Tommy Tune Awards

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).

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.

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