What is your crossdressing past?

[TracyUK]

I would like to hear of your crossdressing past, when and how you started and any near misses you may have had.

[sometimes_miss]

Read the link in my sig. It gives a pretty comprehensive tale of how I wound up becoming a crossdresser, as well as the TG/TS influences in my life.

[Rachelakld]

my story and potos are on my blog

[docrobbysherry]

Here's a unique story for u, Tracy:

When I was married, my ex and I went to a big Halloween party. Her as a tough little guy in a suit. And, me as a cheezy looking female. Beard, balloon boobs, $3 wig, etc. But, I was wearing nylons, low heels, and a cute skirt!

The crazy, drunken evening made such an impression on me that I didn't remember it again until 10 years after I began CDing!:eek:

[Helen_Highwater]

I would like to hear of your crossdressing past, when and how you started and any near misses you may have had.

Tracy,
Welcome to the forum.

It started with a fascination with my mom's girdles and stockings, moved on to wearing my GF's dresses, started my stash with items rescued from the jumble sale sack. Bought a few things from shops pretending they were presents. First trips out were night time drives and quick walks in a car park. The internet gave me access to sites like this and online shopping. Having a job that meant I worked at home alone on a regular basis gave me plenty of dressing time. One or 2 close calls when my SO came home early. Progressed to going out in daylight before attending a support group one evening who gave me the confidence to go dressed into my first shop and it's continued from there. Still in the closet. And that as they say is 5 decades of my CD'ing life in a nut shell.

Not a criticism but I noticed your posts so far have all been titled TracyUK. Can I suggest you title them to reflect what it is you're posting about or it will all get very confusing.

I hope you get as much out of being here as I have.

Helen

[heatherdress]

Tracy - Welcome. I hope you enjoy the site. How did you start crossdressing?

[Tina_gm]

Making it short- the desire was there since high school, but next to no actual dressing until nearly 30 years later.

[BLUE ORCHID]

Hi Tracy:hugs:, I'm 73 and I've been in this program for 69yrs. it's pretty much a lifelong thing for me. ~~...:daydreaming:...

[Chancey289]

When I was a little kid, I use to try on female clothes in secret, however that stopped when I was almost caught. It wasn't until about last year I got back in to it and I went all out. I started buying female clothes and make up. Started practicing it, and now I'm here. I think I've gotten quite good at it, and plan on making my first crossdressing public appearance at an anime convention coming up.

[Lorileah]

that is a pretty broad question. You can search replies to questions similar, or narrow your focus to something more specific :)

[Sister Rachel]

Dammit I just spent half an hour writing a full-on history of my crossdressing then managed to lose it while trying to preview it and simultaneously read your original post :doh:

In short ;

Started at three years old back in 1960 or '61, nearly got caught fully dressed ( bra, panties, tights, petticoat and two-piece skirt-suit ) in my mid-teens, then on and off, purge and splurge, deny and embrace, then, much too late, coming out to wife and family who have all been wonderfully accepting. I wish I'd had more fun before I became a UK size 20 ! Thin as a rail in my early twenties, could have worn all kinds of pretty girl-stuff then :daydreaming:

[Bruce64]

I dont know when I started, I know its not going to stop.

[SHY KIM]

To be honest I can't tell my story to many times:daydreaming:
It's still so clear of a memory which means it was right even that long ago.
Around 5yrs playing on the floor with my mom and another youngster I tried on her little nylon footies. I just remember liking the feel. As time went on I grew interested in watching my mom dress and would try her things on. I remember locking her out of flat once while I tried on her stockings and panty girdle. In preteen years I discovered her pantyhose and made a routine of wearing those along with a black bra and beautiful lacey black full slip. In teen years I outgrew her things and actually "lifted" a few things from neighbors clotheslines late at night on my way home from work.
In late teens I introduced my desires to my girlfriend (now wife of 29 yrs). We grew into things and by mid twenties I started leaving the house totally en fem. After a while I went to a few CD meetings in Chicago bit was still to quiet and shy to enjoy the experiences. Then I had to close things up for along time (at least 12yrs) And thank goodness, after a nice chat with my wife December 2015 Kim came back life FULL BORE!!!
That's my story
Kim

(in secrete -

[CallmeAlice]

I cant remember how I started but I was 12ish

I did it on and off til I was 15, now I do it as often as I can.

I've never been caught.

[Nadine Robles]

Briefly speaking, it all started with a fascination for panties. How much variety of colors, shapes and fabric! early on I fantasized about how would it feel like to wear them on.Needless to say, once I had the chance to try it, there stayed in that special drawer for good...

[threeheavenshigh]

Briefly speaking, it all started with a fascination for panties. How much variety of colors, shapes and fabric! early on I fantasized about how would it feel like to wear them on.Needless to say, once I had the chance to try it, there stayed in that special drawer for good...

Me too. Started when I was 10 and been going for 30 years since.

[Maryesther M.]

In my early 40s I had to work abroad for a time and the isolation drove me to try a skirt I picked up in an 'offer' bin. I shaved my legs, donned the short skirt and saw that my bottom half looked like my spouse's. What a turn on! At that time things were acquired mail-order only, so 'progress' was gradual. I only ventured out at night, but the risk was half the fun.
That was 30 years ago now.

M.

[sara.rafaela]

I dressed when I was young, before leaving high school. Then I stopped for many years, 25? I just did not think of it.

One time, during the summer, I was home alone. I was about 17 maybe. I got dressed in my mother's skirt, hose, top, heels (open sandals and my toes stuck out). I did not have a wig so I used a scarf, like a Muslim woman. I decided to go out and walk a few blocks and come back. On my way back I saw some type of repair truck pull up to my house. I ran. I barely got inside before the guy got out of the truck. He saw me go in. Then I had to endure the multiple knocks and bell ringing before he went away. My parents never said anything.

[TracyUK]

Tracy - Welcome. I hope you enjoy the site. How did you start crossdressing?

I started aged about 7 with my mothers clothes, as I got older and had girlfriends I would when possible dress in hers or even her mothers if I found any in laundry pile. I am sure they must have wondered why I took so long in the bathroom.

- - - Updated - - -


Dammit I just spent half an hour writing a full-on history of my crossdressing then managed to lose it while trying to preview it and simultaneously read your original post :doh:

In short ;

Started at three years old back in 1960 or '61, nearly got caught fully dressed ( bra, panties, tights, petticoat and two-piece skirt-suit ) in my mid-teens, then on and off, purge and splurge, deny and embrace, then, much too late, coming out to wife and family who have all been wonderfully accepting. I wish I'd had more fun before I became a UK size 20 ! Thin as a rail in my early twenties, could have worn all kinds of pretty girl-stuff then :daydreaming:

Rachel, it was the for me, when I was much younger although tall I had a slim waist and wide hips giving a good female shape. Now I need some help.

[kittie60]

I was 7 at the time and had tried on my grandmothers slip and some of her stockings, got caught 3 times then she decide I had to go see a doctor. Finally at age 14 or 15 found out I was trans. This leads to a whole different outlook on myself which is another story later on. Never stopped dressing but always wanted more. Finally I knew what was missing and now 53 years later am very happy living full time as female.

[Abbey11]

I've had an interest in ladies shoes since my early years and my mother would wear her stilettos which I just had to try on. My actual crossdressing and going beyond just admiring women's clothes didn't happen until my 30s when I decided I wanted to try stilettos and went and bought a pair and for a while I just stuck with shoes. I started looking at this site and decided it was time that I went further and bought a dress. Since then it's progressed to to full blown wigs, makeup, skirts, tops, blouses, jewellery, bras, panties, suspenders, more shoes/boots, more dresses. I have purged along the way and until recently had not done any dressing for about a year, however now the desire has flamed again and I'm loving it.
If your interested I posted some very recent purchases on the 'I went shopping and guess what I bought' sticky, in the clothing and shopping forum, if anyone is interested
Hugs Abbey x
Just to add... All you ladies are a huge inspiration to me and for that I thank you x

[Andrea Renea]

I've been doing this for going on 52 years in some form or another. Even before I knew what the word "crossdresser" was. Started with mom's things. Now I have two full wardrobes, both male and female.

I'm my wife's best shopping buddy.

I wanted to wear girl clothes even before I every did, probably 4-5 years old.

I married we had three kids and now I have the title grandpa.

Finally fessed up and told my wife after 18 yrs of marriage. Surprisingly she was really accepting and fussed at me for not telling her sooner. Yes! I'm very lucky.

Next month will be our 36 anniversary

[Jennifer0874]

My start was thanks to my older sister who would dress me up when I was 1-2 years old. I have no memory of it, just the stories my family would tell about how cute it was. Then one day I guess my dad put a stop to it. Although I do recall really wanting to be Wonder Woman around age 5 and stealing my younger sister's underoos. I also remember staring at my moms closet around that age.

Then at 13 it all came back and I've been dressing ever since. Within the past two years I mostly wear women's clothing.

[Cd_scarlett]

My past is not much different. Started very early for me wearing panties and pantyhose. I secretly dressed all through my teens but slowed down in college. Not sure why. By the end of college the desire had returned and increased. I dressed a ton and began going out and meeting people. I had some very interesting encounters with other gurls while en femme during those years... Now I don't get to dress as much as I like due to living arrangement. I have a full wardrobe and make-up now but in just sits in the closet.

[CarlaWestin]

that is a pretty broad question. You can search replies to questions similar, or narrow your focus to something more specific :)

Youngest w/sisters watched makeup curlers then mom's bra excited about forbidden fantasy connected to BD interest shame denial but continued then revelation acceptance still ridiculed divorced tweener insane but thought boobs were cool meltdown single again full reign to CD met wife cool about alternative lifestyle but not CD so now DADT senior heading for retirement hoping to soften situation but still can CD 12 hours every day/night and wanting more currently dressed like naughty teacher gray wig frumpy dress with fabulous sexy lingerie underneath.

:straightface:

[AllieBellema]

I do have a good one about almost being caught...

One Saturday night, after I had a small collection of outfits (half were female costumes that I wore as dresses anyway), I decided to quietly setup a photo shoot using my film camera. Some of the dresses included my first southern belle dress (that I sadly purged when I moved from Michigan), a poodle skirt Halloween costume, a Spanish dress looking Halloween costume, and a couple other outfits that I found unused and unloved among my grandmothers numerous bags of clothes. I also had a pair of panties on too. It was about 1-2 AM and both of my grandparents were asleep, I was setup in the living room with our old large bathroom mirror leaned against a cabinet. I quietly put stuff on and took photos, then swapped outfits and so forth. At one point, I could hear my grandfather wake up and get out of his recliner. I panicked and quickly stuffed all the clothes between the coffee table and the couch and took everything off of my body... right down to the point where I was butt naked. I turned the lights off and laid quietly on the couch as I was naked there. My grandfather came out and went to the kitchen to get something to drink... he was right around the corner.

I quietly laid motionless... he got his drink... and went back to his room and I heard him lay back in his recliner to go back to sleep. I was one light switch away from him catching me with all these women clothing stuffed between the couch I was laying naked on and the coffee table... and of course, me laying there naked. Once I knew he was asleep, I got back to taking photos and finished up quickly so I could take everything back to my room and go back to normal teenage boy stuff.

Knowing how he was ok with me later on no matter how I was aslong as I was happy... I do wonder if he would have turned the light on, how he would have reacted. Granted, it probably wouldn't have been good and would have been fun explaining why I was naked on the couch... lol.

I do got a couple other stories for later times over how my grandmother could have caught me in my southern belle dress... and how my grandfather opened the box that contained my hoop skirt.

[susan54]

Some of the stories here are distressing, involving abuse.

I had a charmed time. Yes, my mother caught me - I was about 20 - followed by purge she persuaded me to have- but after one particular relationship ended I went for it big time. Got the whole outfit, boobs, wig, make up and for 20+ years not only dressed regularly but went out a lot. Now I wear women's clothes almost all of my free time but with no make up or wig and use these only for going out, which I have cut down from 2-3 times a month to once every 2-3 months, and cut down the purchases because I have more than enough clothes - about 750 dresses and almost 1000 skirts. I have had relationships with wonderful women who remain good friends but am now single and perfectly happy. I do not have gender issues - I am happy to be a man. So no traumas, no abuse, no gender issues, just a very nice life of which cross-dressing is only a lovely part. I don't regard this as a problem and all my experiences in these outfits has been good. Later in life my mother came to stay for an extended period and I just told her I would be dressing in women's clothes and she was fine with it. I have a wonderful job,friends and home - and wardrobe. I am not out, but I don't see any need to be - there are people I trust and they have never abused this trust. Life is entirely happy - so there is happy ever after in cross-dressing. Please be aware of this if you are having problems or are the partner of a cross-dresser.

[LovelyLeesa]

I started at 9 when I tried on a pair of pantyhose. Loved it and went from there wearing panties and bras and hose whenever I was home alone. For the longest time my sisters stuff fit me so I would borrow her dresses and heels and sneak my moms blonde wig and go out for walks. I felt so great! And scared! Almost caught a few times but I learned to be quick when I saw the headlights pull in. In my teens I would still dress up when I could and when my parents would go on a trip and leave me for a few weeks I would dress all the time! If I was out and about I would have a stash of my own clothes in case I had to change before going home (sometimes we would get people and deliveries unexpectedly). I would also go for a drive at night fully dressed. I got to be pretty good at makeup too. I stopped at a store a few towns over one night when I was 17. I really needed to go to the bathroom and wanted some snacks. I sucked up the courage and went in. I quickly walked past the guy at the cash with my face behind my wig and headed for the bathroom. Since I was dressed I thought I may as well use the womens room. After I finished and checked everything in the mirror I got the courage and walked out into the store. There were a few other customers and I noticed that despite my fears no one payed me any attention. I grabbed some snacks and went up to the cash. The guy was obviously bored and wanted to chat. He actually made a few nice compliments about my dress and I tried to speak as little as possible as I was freaking out! Just as I grabbed my stuff he asked for my number! I quickly jotted a fake one down on a receipt and left. My heart was pounding at that point. I hopped back in the car and drove away!

I've never told that story before!

I've been dressing up whenever I can. I am 45 now. As I write this from my room away from home I feel so at home in my lingerie and hose and little black dress. If it wasn't that I don't have a wig here I would go for a walk outside!

Enjoy life!

Leesa
xo

[flatlander_48]

T:

I have bits and pieces of memories from childhood, but no clear sense of the chronology. What I do know is that the closet in my room was the overflow for my mother's clothing and shoes that she wore less frequently or were out of season. Instead of going to bed, sometimes I would hunt for something interesting and try it on. For sure that's where my liking for wedge heeled slides started. While I don't remember getting caught (or I may have blocked it out), I do remember a number of close calls. The only thing that saved me was that it was quite a few stairs to get to the 2nd floor, and that I had j-u-s-t enough time.

The first time I went out dressed was Halloween 2003 at the age of nearly 55. The next time was January 2014. In between I accumulated undergarments, dresses, skorts and tops and spent 6 years working outside of the US. I started dressing and going out in earnest just before Christmas 2014. Since then I've gone out fully dressed 2 to 4 times per month to gatherings of a social group, a support group and a weekend breakfast group. Attending these various gatherings has helped me be comfortable as DeeAnn in the outside world. I've shopped for DeeAnn as DeeAnn and as Don.

In the time that I have been dressing, I've felt very little of the shame and guilt that people talk about. I've never purged. Until this past October, all of DeeAnn's outings were in other towns; 30 minutes to 90 minutes away. But, in October DeeAnn was the Mistress of Ceremonies for an entertainment event in front of ~130 people. I presented my alter-ego as a stylish and appropriately dressed "older" woman. All totalled with 2 other events that included a photo from the previous event and an explanation about DeeAnn and talking to my kids, 8 close friends and my department manager, the result was outting myself to 200+ people. It is a case of being able to lay that burden down...

DeeAnn

[Sister Rachel]

TracyUK,

I'm tall too, I've spent money on lovely dresses but even the ones from Long Tall Sally are a bit too short in the bodice, they hang in my wardrobe to be admired but I rarely wear them, it's usually a skirt and top for practicality!

[Cristy2]

My crossdressing past? To be one hundred percent honest, I really do not have one to speak of. The late Christinac was one of my best friends and I was around her a lot especially when she really began to seriously question her sexual identity and she began to crossdress more and more. I wore a few of Christina's skirts before out of just playing around with her, but I never took it seriously. However, here very recently ( with in the last few months) I have found myself asking myself the same questions that Christina struggled with, so in a way, I'm on an adventure to find out who I am.