Crossdressing from A to Z

[Emily Anderson]

Many of us started crossdressing at an early age, borrowing our mother's or our sister's clothes. Often it started with panties or pantyhose, a slip, a skirt or a dress. But, what took us to the next step?

How did we evolve from that initial step to where we are today? What drove us to continue crossdressing after that initial experience?

[xoAmandaxo85]

thats a good question im going to have to think on that one for a while

[Joy Carter]

It's a very long story Emily. In short, I feel like I should have been born female.

[Sarah...]

Well, between 5 and 12 years old - I've no idea. After 12 it felt right en femme and wrong in drab. Now, once I've discovered a new style or colour that works for me, that's what keeps pushing it to the next step. A constant discovery of what goes with what and what looks good on me. Sheer bliss!!

Sarah...

[Nicole Erin]

Like any other good thing. Once someone has had a taste, they want more.

[trannie T]

It was not the bra or the panties that started it, it was the fact that I wanted to wear the bra and panties.

[Jonianne]

What drove us to continue crossdressing after that initial experience?

After putting on my Mom's cloths at age 7, the desire to touch or connect with the female never went away. It remained near the surface of my mind ever since. Whenever I would go to a park or amusement place with extended family, I would always dream that maybe my cloths would get messed up and I would have to wear one of my cousins dresses back home. That kind of stuff. I have no idea why I kept thinking of scenarios like that, but I did.

The drive, I guess, was just I needed to express or feel connected to my femme side.

[Chronos]

I can not honestly say how it started for me, it just did. It had always interested me, but for the life of me I can't remember any event that sparked that interest. :doh:

After I started looking into it more the urge to dress just got worse. :D

[Tara LaBelle]

One does not dissect gossamer

[Angela-Russell]

After trying on a dress at 12 or 13(sisters school dress actually), I found I was totally hooked & couldn't stop. I just wanted more & more to look like a girl, but I couldn't explain why. I'm glad to say that after all these years the urge to dress is still there, & I hope it never goes away.

[bah-bah-bobbie]

I was happy with high heel shoes for years. I was a teenager when I figured out pantyhose were worth the extra effort. Then in my early twenties came skirts, followed by blouses and dresses in my mid twenties. Late twenties brought experimentation with make-up. Early thirties (last year) I got breast forms. I am now waiting for halloween to find decent quality/priced wig.

[kym]

well it did start with pantyhose, but then i figured out that pantyhose look better on me when i have on heels, then a skirt and then..... well you get the picture.

[Farrah]

I honestly do not know. I just know one day I found myself in a skirt and wondering, "I should have done this a long time ago."

[Angela Dressing]

I was at home one day and mom was gone, for some reason i was gravitated to her clothing drawer and started putting on her undies. felt very nice went to her closet and found some dresses and shoes. I still have urges to wear ladies clothes but my wife's stuff doesnt fit very well. started buying my own panties but thats as far as i have gotten. Im very happy being a guy but there is a woman in me that keeps whispering in my ear.:eek:

[Andi]

I think the devil made me do it! LOL. :D

[CD Susan]

Emily, that is a somewhat hard question to answer. I don't think I have progressed in steps but rather a continuous transition into who I am now. I can remember wearing my sisters clothes over 40 years ago and that was the start of this long journey that I have been on all of my life. Through out the years I have stopped wondering about all of this and now accept it as who I am. I know that I can't change this part of who I am so I am willing to accept and enjoy it. To me this is a very enjoyable lifestyle and will never want to change it.

[jenalex]

I've crossdressed as long as I can remember

if there's something that started me off at age 3 (or younger) I've no idea what it was :battingeyelashes:

[Lisa O]

What possessed me to wear my older sister's clothes at about 4 is a mystery. Since then, a series of events sometimes years apart seemed to click. Working and family have slowed it a bit but there is still a progression. It has never gone away and I hope it never will.

[Janice1948]

For some unexplainable reason I tried on my mother's undies when I was 11 or 12 and over the next couple of years I "graduated" to her stockings, slips, shoes, dresses and makeup. Eventually there was sexual gratification from it, but I don't think that was why I continued. Of the course of many years, I purged several times because of my wife and children but, there was always and I mean always, some irresistible force that drew me back. Now in my later years, I have a closet full of femininity and dress somewhat every day. I'm sorry to digress from the question. I guess the bottom line is that I really don't know the psychology behind my desire to dress. I can only tell you that I feel my best when dressed.

[Jillt]

Like JAT about 3 yrs old, but I definately recall seeing the most beautiful lace slip (older sister's) and thinking thats me once the slip and panties were on the skirt n blouce followed quickly the rest is history

[dominique]

For me it was just the variety of clothes women could wear. I tried them on and thought this is for me. Now it's a large part of my life and I do enjoy every single minute of it. I wouldn't want to have it any other way.

[girl_in_pantyhose]

What can i say pantyhose are the gateway to crossdressing for me! from there it was all down hill. When i was old enough to go shopping alone around 15 or 16 i started to buy dresses and as soon as i could get a credit card i was shopping for heels online. then just a year ago i put it all together and i will never be the same! I don't know why i waited so long. but that is my A-Z

[Claire3]

Sorry Emily,cant really help.It just all kinda fell into place.:love:

[Kendra (Tx)]

It's really tough to say what actually got me started...:thinking:...I do know it was when I was about 6..For some strange reason I was "drawn" to my moms things...( stockings, slips, and bras )...I didn't consciously say "Today, I'm going to try on some of moms things"...It just happened...And I loved it...Perhaps I was meant to be a woman...Who knows...All I know is..I am more comfortable as Kendra, and I consider her a part of who I am...I actually got "serious" about dressing back in 98...And I think I've "evolved" pretty well...I only regret not starting much earlier in my life...Who knows where this girl would be..:daydreaming:


http://kendra954.com/kendra2.jpgMy very first pic ever posted on the net ( circa 1998 )


http://kendra954.com/June02/kendra22.jpg And one of my later looks...I think I "evolved" nicely...:battingeyelashes:

http://kendra954.com

[FlygrlChristy]

Same here, just somehow drawn to Mom's knickers, nylons, garters, shoes, girdles, bras, etc. I just couldn't get enough of the feeling, and kept on wanting progessively more, and just couldn't stop. I always wondered why I was so drawn to feminine things, I still remember looking at one particularly gorgeous girl at my bus stop when I was in Jr. High, and thinking that I wanted to be just like her.

This thread makes me wonder, since there seems to be a common theme among most of us that starts with either our mothers or sisters clothes, how many of us, started doing this with out either one around or available, and why such a strong connection there?

Christy

[joann07]

What can i say pantyhose are the gateway to crossdressing for me! from there it was all down hill. When i was old enough to go shopping alone around 15 or 16 i started to buy dresses and as soon as i could get a credit card i was shopping for heels online. then just a year ago i put it all together and i will never be the same! I don't know why i waited so long. but that is my A-Z

Hey girl! You're a copy cat! Ha ha! :heehee:
Pantyhose was the definitely the precursor to my dressing. I secretly wore them from my early tweens until today. It was only a few years ago when I started fully crossdressing.

Hugs!

[Dawna Ellen Bays]

An aunt of mine (who was young herself at the time) had an AMAZING pair of boots (soft brown leather with zippers up the sides that I could easily slip on and enjoy. I had NO idea that "innocent" experience (I was maybe 5 or 6 at the time) would lead to a "feminine side." When I was 14 or 15 and home alone for an entire day, I experimented with my sister's makeup and wrapped a scarf around my head and stared at my "visage" in the mirror all day. I STILL had no idea that I was a transvestite/crossdresser. When I turned 18, right after my high school graduation, a friend lent me a "dirty stories" magazine (like Penthouse Variations), and there were two stories I'll never forget: one was about a guy whose female roommates completely dolled him up, the other was about a guy who would dress like a high-class call girl and would get "picked up" by his wife (who dressed in a man's business suit). When he described his "long red nails" and "sexy black sheath," I finally realized what I was, and I was damn happy about it!

[Angie G]

I dressed hear and there for years nothing like I do now that the wife knows. That was a big step up for me. :hugs:
Angie

[allisonrn06]

Until I was about 18, I hadn't anything but pantyhose, and occasionally heels and hadn't really thought about anything else. Then I started reading stories in a magazine( which will remain nameless) about others who liked wearing all women's clothes and realized that I wanted to be a complete CD too. Ididn't dress fully for the first time till I was about 21, and with only occasional pauses since then. Having an accepting wife now, there will probably be no more pauses!!

[frenchie]

Hi Emily, well I used to do kissograms as a man dressed in all sorts of things such as tarzan, policeman etc(i was muscular but not to big and my legs were always quite slim looking)
Then I was asked if I would dress up as a woman for a kissogram.I thought hey ok,I was about twenty two then.After that I got more work as a kissogram and it became virtually a full time/after work job earning extra money.I only did these kissograms for women and they found it really interesting/amazing that they had a bloke dressed up as a woman.I then stopped for a few years as I got kinda fed up with it.Then I met my wife
i told her what I used to do and then started Kissograms again with her support, though at the time we both didn't really understand that I liked to CD.I stopped after a few months because it was too much hassle( getting dressed up night after night was playing hell with my face i was getting such a rash).
A few years later we both decided to move to France, and after some nights playing around at dressing up after a few glasses of wine ( my wife thought I looked good in heels), we jointly came to the decision that i liked dressing as a woman.I was relieved, I had been feeling it for a little while by then.My wife at first though was worried that I was Gay and thanks to her finding this website, all her fears kinda vanished overnight( well after a few weeks anyways).
When I mentioned about being gay earlier i just want to say I'm not having a go at anyone who is Gay it's just that it was important to my wife to know that i wasn't,we have been married for nearly 10 years now, and hey i think that would be a bigger blow to her than realisng I just want to share some of her clothes.
Well what can I say we have a great realtionship, we're trying for a baby, we love each other very much.My wife has two brothers and has not known what it's like to have a sister,until now.Sometimes I say to her Is it ok If Gina comes round for the evening? and sometimes she'll say to me that she wants Gina to come over and have a bit of a girly chat.
I'm gonna stop there as I think I'm waffling on now and I may have started to bore you all ..................Frenchie ...........Gina

[Jennifer Giovannetta]

I am going to need some time to think of this more. But what comes to mind initially is that the feelings built up, and the urge became stronger over time. I also believe that as we get older, we see life differently. When my father died, for the first time I saw how fragile life is. I am going to die someday. Maybe soon, hopefully later. But while I am here I want to make the best of it. Even if society does not want me to. Sometimes life is hard and can be disappointing (more often than not). Crossdressing is something that allows me to escape.

Even today I am still moving forward as far as dressing is concerned. There are still some things that I feel funny about doing. Like applying fake fingernails. But then again, i felt the same way about makeup. Now I love to put on makeup. It seems that for me it is a journey. Tonight I am going give myself a pedicure in a pink polish. I have never done this before. Usually I do my toes in a color that does not stand out.

The whole thing for me was a gradual. Although sometimes I wish that I made these discoveries earlier, but better late than never I guess.

[Charla]

It started for me when I was 10 - I fond my sister's panties and bars and tried them on and liked the feeling of it. Later, when I was out of school and had ot stay at my grandmom's house (where my sister lived) I would put on her panties and wear them for a couple of hours.

[Jilmac]

I'm not really sure how it evolved for me. I know I always loved dressing in feminine clothes and yes, I did borrow my sisters' panties and bras. I think when I was able to buy my own panties is when it escalated for me. But there was also the mystique of the forbidden fruit which could have been a driving force. Luv and :hugs: Jill

[Deelite]

Like others here ive dressed from an early age wearing underwear, swimwear, shoes, boots, hosery from your mothers wardrobe, i did'nt really understand my urges, i just had an uncontrollable desire to wear them.

Thinking about it's only since being a member here that i've discovered myself, by talking to others here, understanding i am not a freak and my feelings for dressing are not unique.

Since joining this site, Dee has evolved and i am slowly understanding why i got all those urges when i was 6 or 7 and i've learned to accept them and they are a part of me.

All i can say is thankyou girls for helping me understand me!

[satin_luva]

For me, I think it was discovering my stepmum's satin nightie on her bed. I felt compelled put it on and after I did I felt great.

Deelite, have you got anymore pictures of that seeminly hot (English?) maid uniform?