What is your crossdressing past?

[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.