the tipping point

[Jenniferathome]

I am, I think, a typical average cross dresser. I started by stealing my sisters panties and wearing them in bed when I was about 8. Over a few years, the typical progression of dressing with a few more items of clothing and gradually make up. I think I stalled a bit from age 10 to 12, never wearing more than a stuffed bra under a leotard. When I turned 13, I had a red letter day in my cross dressing activity. I put on my first dress. I can remember that day and dress like it was yesterday. It was a floral pattern and had a tight bodice, loose pleated skirt and zipped up the back. The funny thing about that day and that dress is that I was frozen in my sister's bedroom holding the dress and wondering if putting it on would make me gay! I mean, I was wearing a bra stuffed with socks and panties and pantyhose and I'm debating the wearing of a dress. Well, I put it on. I loved it. And I didn't become gay, just a cross dresser.

Did you ever have such a "moment"? Some particular outfit that you can recall that cemented your cross dressing mind?

[Ariamythe]

Mine was an outfit I wore the first and only time I went out in public dressed. It was high school "spirit week" and they did a cross-dressing day. Most of the guys who participated did corny, cartoony girl looks, but I cobbled together things from my mother's closet (I didn't have my own clothes) and went as en femme as I could. It was a blue knit sweater and a white skirt (like a stretchy jersey material) with pantyhose and sneakers. Best day of my high school!

[AmyGaleRT]

One of my major tipping points (or "awakenings" as I've come to think of them) was when I wore the first dress I'd bought for myself, a black sheath dress I'd ordered from JC Penney. Previous to that, all of my clothes had been nightgowns. But, in wearing this, I didn't feel the arousal undercurrent that had always been there with my gowns. Instead, I felt comfortable, and happy. I was smiling. That's when I began to suspect that there was more to my dressing than just the nightie fetish...and it led to my belief in myself as having a part-female soul, and also to my assembling other items and working towards a fully femme presentation. (I don't have that dress anymore...I discovered that sheath dresses don't really suit my body type, and I donated it. But I have many other dresses that work better now!)

- Amy

[Beverley Sims]

When I was 17 a group of girls made my face up.
I did not recognize myself.
When the wig went on I was just about out of it.
A dress was suggested with a bra and padding.
I was then taken out to a soda fountain and shopping for dresses.
We went to one of the girls places for dinner and watched TV.
When I was taken home my mother looked for a moment, gave me a night dress and told me to remove my makeup before I went to bed.
Boy/girl, was I confused.
After that all I wanted were a few encores.

[Julie Denier]

I dabbled with bits and pieces throughout my youth, but my "tipping point" was when I finally dressed head to toe, including wig and makeup, at age 38 (I'm 40 now). I just loved the look and feel, and knew it would continue to be a part of me.

[Krista1985]

Two and two finally made four when I discovered the existence of breast-forms about 4-5 years ago.

When I was about 14, I discovered/developed an affinity for TG transformation stories online. Erotic fiction about a man turning into a woman always did it for me, and I always put myself in the protagonists role in my daydreams. Around age 20, I started filling up water-baloons and stuffing them into an altered t-shirt to simulate breasts. I had zero access to femme clothes that fit at the time. Looking back, I suppose this was a form of crossdressing, but I never considered it as such because it didn't involve female clothes.

So when I stumbled onto an image of breast-forms on the internet one day, and a bra to house them, I felt the need to get myself a pair. Somehow I knew that if I got them, I was taking a huge step forward from fantasizing about being female-bodied (a fantasy that had always floated my boat) to actualizing the vision of myself as a member of the fairer sex. Nervous as could be, I rounded up some cash and headed to a TG specialty shop in a big city far from my home. No credit cards, no paper trail... I was paranoid. The moment of truth arrived, and I calmly made my purchase and embarked upon long journey home.

Agonizing about my decision during the long drive, I rationalized that if I tried this stuff on and liked it, that would make me an official crossdresser. It was the death-rattle of my lingering doubts and nothing more. I returned home, locked the door, pulled the shades down, put on my goodies, and BLAMO! A crossdresser was born. I didn't just like dressing myself up as a woman, I loved it. That was roughly 4 years ago.

That's my tipping point in a nutshell. The rest came later, wigs, dresses, make-up and foundation garments, but it was that initial attraction to forms that jump-started my transgender adventure.

[Skyeyes]

For me it was shortly after I was out of the army and living alone. I had worn my mother's underwear when I was young, but had not dressed in anything feminine since I was 15. Suddenly I had the desire to dress again. I left my apartment and went to a small ladies clothing store in a nearby city. I looked around and suddenly I saw a bra slip. It was so beautiful. It had lacy cups and a beautiful lace trim at the bottom. I knew I had to have it. I went to the counter and asked the sales lady to help me. She was very nice and selected a size that would fit me. My heart was racing as I drove home. Once in my apartment, I stripped down to nothing. I put the slip over my head and pulled it down. I can still remember the wonderful feeling of the silky material going across my body as I pulled it down. I stood in front of the full length mirror and looked at myself in this beautiful bra slip. I knew at that moment, I could not deny that I loved wearing women's underwear.

[Raychel]

For Me, I am sure that I have had a few of those moments in the past,
The first time I slippped on a pair of panties, The my first bra.
then my first dress. Ect, Ect, Ect.

But with my memory the way it is, Do you think i could ever remember any of those times.

But It doesn't really matter I guess, I still remember how to crossdress, that is all that matters.

[suzy1]

And I didn't become gay, just a cross dresser.

You didn’t become gay Jennifer!...............that’s odd?

To be honest the first article of female clothing did it for me. I was about 4 years old and used to put on an old nightdress and sleep in it all night. When my mom came in to kiss me good night I used to pull the covers up to my chin so she didn’t see.
I used to take some big risks in those days.

[Billie1]

For many years as a pre-teen, I had been putting on bits and and pieces of girl's undies, swimsuits, leotards, etc, whatever I could find, or sneak out of a dresser drawer. Didn't understand why, but was drawn to them. As a 15/16 year-old, I finally got the courage to by a pair of pantyhose at the supermarket. I went home, put them on, and that was it! The tight nylon hugging my legs, the feeling of my legs sliding together, put a spring to my step, energized me in a way I never had been before, and the rest is history. I've never looked back from that point, only forward!

[stephNE]

No, I don't think I ever had "a moment". This has been with me since 4 or 5. I've always been drawn to womens clothing.

[Erica Marie]

I dont know if I ever had an honest and true tipping point. My dressing started more as a sexual thing when I was about 13 and as the years progressed it changed slowly to more of a way to bring out my feminine side. Each time I get the chance to dress and see the transformation the little more I want to go ahead further. For me it will never be to change gender but express myself for who I am.

[Angela Campbell]

Yes I did have a "moment" that was quite intense and even life changing. I knew from around 4 years old I was different. I knew I should have been a girl not a boy, but also learned early to keep it to myself. I did dress in my mothers things and was very careful and never was caught. As I grew older I continued with panties, bras, slips and other items as I could but never actually dressed all the way. I got a job, got married, had kids and a mortgage, all the normal stuff we are supposed to do. I would often dress in my wife's underclothes when I was alone, and when out of town for business I would buy a few things and then throw them out before going home. So for years and years I dressed in private but was constrained by a very small selection and time designed to keep it a secret.

Life continued, moved along, I got divorced, married again and eventually divorced a second time. That brings me to the age of 54. For the first time in my life I was living alone. I found a wig my ex had left behind when she left and tried it on. I liked it so I decided to go out and get an entire outfit, with shoes, makeup and the works. Looking back I am sure this outfit was awful but for a beginner I guess not too bad. I put it all on and did some makeup. I looked in the full length mirror and in that one moment my life changed. It hit me hard and was something I never expected. I looked in the mirror and for the first time in my life I saw ME. A woman was looking back and it was the woman I always was but could never find before.

That moment was last July. Since that time I have begun a process to improve my look, losing over 85 lbs so far, using lotions to soften my body, trimming my eyebrows, shaving all over, and even beginning to go out in public. I spend about 3/4 of my time fully dressed now. That one moment did indeed change my life, for the better.

[Kelley]

I had two tipping points. The first was when I was around 6, alone while my older sister went next door. My younger sisters panties were on the floor in her room. I kept walking by looking at them and wondering what it would be like to try them on. I finally decided to to try them on and that started my obsession with lingerie. Less than a year ago my wife found my stash and after the "long talk" she accepted my CDing and I was able to wear my beautiful long nightgowns around the house with out the fear of getting caught. It was at that point that it became non-sexual and I finally understood what it was about. For me my avatar represents the end of one phase of my CDing life and the start of a wonderful journey.

[Maria S]

When I was young I used to watch Danny La Rue and Dame Edna Everidge on the telly. Even though I knew they were female impersonators you rarely saw them dressed as men so I got it into my head that they dressed like this all the time and probably enjoyed doing so (remember I was only a boy at the time). I had to see what the attraction was. I went into my mum's bedroom and put on a pair of tights for the first time. Aah that looked good and felt good as I stroked my hand down my leg. Right next a bit of shaping, lose the belly and a bit of bust required. My mum was a roll on user rather than bra or corset. Squeezed myself in and filled the cups with socks. Shoes, sorted through them and found a nice pair that fitted. This was the tipping point for me. As the days went on I gradually worked my way through skirts, dresses and tops to find what fitted and what looked good.

Maria

[Kate Simmons]

I never really hesitated to put a dress or anything else on Hon.

[reb.femme]

Major point for me was aged 17. I moved in with my then girlfriend (now my wife) and I adopted a whole wardrobe of clothing. I particularly liked a blue knee length skirt with hidden red detail in the 2 front pleats, a white blouse with little figures on and a zip up cardigan.

"Other than that, my memories are vague".......she lied.

Rebecca

[Miriam-J]

I think I've had two tipping points as well. The first was when I was a teen trying on items from my sisters' closet, and learning that I enjoyed it. This set the stage for years of covert, short-term dress-up, often sexual oriented. The second was after my separation from my first wife five years ago when I determined to explore crossdressing as a more overt activity, which was subsequently moved forward considerably with assistance from my current wife.

Miriam

[SandraInHose]

I'd don't know if 'tipping point' would be the best term for it, but...

Although I'd been dressing for several decades (99% of the time form the neck down) the moment I put on a real wig something clicked. I'd worn cheap Halloween wigs on rare occasions (I'm not passable...don't leave the house), but the look and feel of an expensive well-made wig, it took my breath away. Even considered for a moment of shaving off the goatee and seeing what I could actually look like all dolled up. I'm sure I'll end up doing someday!

[CassandraSmith]

To be honest the first article of female clothing did it for me. I was about 4 years old [....]

Wow, I was about 4 also and put on my mom's long girdle and jumped into bed with her. She realized I had it on and told me to take it off. I immediately knew I was different because I loved it. A few years later, I tried on her long line black lace bra and it was even more intense.

[flatlander_48]

Halloween, 2003

My wife and I had just separated in preparation for divorce. I had taken up with a woman, shortly before that time, that I had known (but not romantically) many years before. A couple of years after the divorce, we eventually got married. Anyway, we would spent weekends together and just had a wonderful time. We joked about going out on Halloween, but with both of us crossdressed. The more I hesitated, the more encouraging she became. She also knew that I was bisexual, so the idea of having a strong feminine side wasn't such a major leap.

So, after combining the bounty from a trip to the GoodWill (a dress) and some things that the wife left behind (a wig and black patent leather flats) I was ready to go (although VERY nervous!). I won't go into detail about what my future wife was wearing, but let it suffice to say that when she pulled up her long sweater, it revealed a lavender strap-on. Off we go!!

The first stop was a theater on the Cornell University campus that was showing the Rocky Horror Picture Show. You could get in for free if you were suitably attired. Needless to say that we were welcomed! My future wife even flashed the kids selling tickets. They were laughing so hard that I don't think they could have gotten the words out to charge us! The final stop was a gay bar in Ithaca that is now just a regular bar except for gay special occasions. We danced and drank and just felt like there was no place better to be. I also received my first compliment en femme. A woman told me I had nice legs. Definitely over the moon at that point!

Unfortunately I have not gone out dressed since. Basically it is due to circumstances and opportunity. However, since then I have underdressed about 75% of the time and over the past year, it's 95%+. My wardrobe is now fairly extensive although it is geared more towards warm weather. I'm usually fully dressed on weekends and nearly always sleep in a night gown or Victoria's Secret pajamas; often with bra and forms.

I think the significance of Halloween 2003 was that it seemed to legitimize what I was thinking about myself. For a while there I thought I was really strange, but the support of my wife (current wife) made a very big difference and still does. Who you are is who you are. It doesn't change because you happen to wear a dress.

[I Am Paula]

Boobs. Probably the single most important part of what I am. At about eleven, I put on one of my sisters bras, stuffed with socks. I had an experience of almost religous perportions. I discovered ME, just looking down at lumpy ole sock boobs, I became a different person. I felt like a super hero, and a supermodel, as my old persona disappeared, an a new bigger, better one emerged. When I was still jumping back and forth between male and female, working as a male, sometimes travelling as a male, the boobs kept my sanity. If I had no other feminine piece with me, I always knew I could put on some boobs, and the world would become a better place. I never thought of boobs as something sexual, it was never a fetish, they were just the part of me that defined me.
I've thought, I could give this all up, go back to just being one of the guys...if I could just keep the boobs. Luckily, if I sit down the thought passes. I like the whole package too much to ever quit.-Celeste

[Gillian Gigs]

I can think of three distinct points that tipped me into CDing. One first was beyond my control, as I was dressed in panties and girls clothes as a punishment off and on from 4 through to around 10, or so. The second was wearing some of my sisters clothes, by my own choice, one outfit being a cheerleaders outfit, and the other being a crinoline under a poodle skirt around age 13. Then the third was my first "release" around 13 or 14 while totally dressed to the "nines" in a combination of my Mum's and sister's clothes. From that point on it became a regular activity when ever no one was at home, and I spent alot of time alone as I was the yongest with both sisters married by the time I was 12, and parents who lead a very active social life. It was a tip, tip, and over the edge into gone from that point onward.

[janet p]

Mine was the first time I was at my buddies house and we but on some of his mothers old dresses (my was silk) so we could sneak into the girls camp and spy on them we were about 6 or 7 and I've never stopped.

[Ms. Laura]

This was a fun thread to read and think about!

I was always a typical, you know, excitement dresser. Well, one Halloween, my friends and I were looking for a group costume idea. My mother suggested we all be Miss America contestants. Well, of course I went at it with gusto! My wife had a "large" friend who lent me a gown, I bought some slingbacks, we all rented wigs, and made sashes. Someone's gilrfriend helped with makeup.

We all went downtown to a local Halloween festival and walked around and waved to people.

While this was a costume, not really an expression of me, it let me know that there was more to myself in there somewhere that wanted to come out!