What kind of life do you have as a Cross-Dresser?

[Judy-Somthing]

Is it great, tuff or?

I started at about 5 and in my mid teens and turned my friends on to it!
In my mid teens 15 to 19 I cross-dressed with friends and the girls would do our makeup!
Yes pot and alcohol was also part of the fun.
My wife (to be) heard some of the stories but must have thought it was just fooling around.

Of course it's hard to remember what I was thinking back when I was twenty but, I don't think I considered cross-dressing as something I had to do, it was just something I enjoyed doing!

The Answer for me is "I hate that I can't dress unless it's totally in secret" I don't like sneaking around!
Another thing is that my friends, brothers, sisters, and mother, thought it was OK. so what was I to think?

[Kaylin]

Love the post. I started back when I was around 11 or 12. I started sneaking my aunts dresses and pantyhose and dressing up in them whenever I could until I was caught then she allowed it. i came out to my wife about 4 months ago. But she wasn't surprised. She's found stockings and pantyhose in my sock drawer over the years. And some skirts etc. She wasn't shocked. LoL all is good

[sometimes_miss]

Closeted forever, now I'm going to retire to a much smaller community (away from NYC metro area), so it's probably not wise to out myself and become a front line warrior for the cause at 63, in a redneck territory. I may need my neighbors at times, so potentially causing them to think me a freak is probably not a good idea. We'll see as time goes on how everyone feels about gender bending after I settle into my new home.
Crossdressing has been my cross to bear for most of my life. I'm used to it. If I must continue to remain in the closet, so be it.

[Abbey11]

Things have been ok but not great, too much secrecy, but things maybe getting better. Just put a post on the from that explains.

[BTWimRobin]

My crossdressing life started as a child. My mother's twos sisters lived in the upstairs apartment of our house. As a little kid 4 or 5ish I would always play dress up in their clothes. When I was around 11 or 12, I would experiment (for lack of a better term) with their lingerie and makeup. While I got caught a few times, they did seem to be all that upset. When I was around 20, my girlfriend, at the time, used to love to dress me up in full makeup, bra and panties. I loved the way I looked and how I felt. When we broke up I think I was more upset that I couldn't have someone do my make up anymore. Over the years my desires to desires to would come and go and were far and few between. When they did come, they were not so bad and I could easily suppress them. When I hit 50 they started to come more often. By the time I hit 56 I couldn't hold them back, giving into them. My wife is accepting and while she is somewhat supportive, she is far from encouraging. She doesn't mind me dressing as long as I keep it tasteful around her.

My life right now as a CD is pretty darn good. I am a lot less stressed and much happier now that I can openly express my feminine side in the safety of my own home.

[Maid_Marion]

Luckily I live in a rather accepting social bubble.

[Maria 60]

I don't remember the exact age but I remember sharing bedroom with my sister and wearing her things, mostly pantyhose and her slips. One week before marriage I threw everything out thinking I was never going to be wearing women's clothes again. Instead one week back from our honeymoon I put on her pantyhose and decided these feelings are real and I wasn't going to be a fugitive the rest of my life and when she came home from work I sat her down and told her everything from day one. My wife believed it was a fetish and wanted to see were I was going with it, she has called it a blessing and I call it a curse. Its a bitter sweet for her but she loves that she's the only one that shares my secret, she loves sharing things and shopping with me. Almost like she has the best of both words, a husband and a best friend. She believes we have a strong relationship because of the dressing. So I would think its ok because my wife enjoys it to, but sometimes I think it's a distraction in my life and stops me from other things. The bad part is always the fear of being caught and at time taking chances because in life we always want more.

[NancySue]

My cding life is great...Like many, began early, have come to terms with myself, and have a wonderful accepting, helpful wife. My only issue is going out. We live in a very conservative, low tolerance community. Yes, I, occasionally, venture out, mostly after dark, but with much trepidation...flat tire, police, but mostly being seen and recognized. We once drove to an out of town mall, and still saw people we knew. Thankfully, they didn’t see us. We are active in our community. The social consequences of getting read, caught..would not be good. It’s especially frustrating when my urges to go out hit.

[wendy]

For the longest time, I would classify my CDing as "tuff". When I lived with my parents, I had a lot of time to myself as my parents were usually at work, so I had a good chunk of time to CD. When I met my wife, it became much more challenging, as we spent much time together. When we decided to move in together, my CDing time plummeted, and when I did have time to myself, I was super paranoid for fear of being found out (I couldn't fully relax as Wendy as I feared my wife could come home at any time).

When I spent years in medical turmoil, my CDing practically stopped. After so many years, my medical issues have stabilized, and my CDing came back but with a vengeance. It was still a tuff time for me as my wife didn't know about Wendy.

After I admitted I to my wife about Wendy, I am classifying my CDing now as (very) good. She doesn't like me going out of the house as Wendy, but she has no problems with me being Wendy inside the house at all. Plus, when she is not around, I can fully relax as Wendy without any fear or paranoia of being caught.

[Jodie_Lynn]

It's been a mixed bag, full of ups and downs.

[deebra]

Judy it's hard to believe you turned your friends on to crossdressing. Also that your friends, brothers, sister and mother thought it was O.K. You said it, I believe you, just hard to believe that many would be O.K. with a guy dressing in girl clothes.

[Sarah S]

I love to dress every day when I get home from work and I'm lucky to have the support of my wife who loves me as Sarah

[AllieBellema]

Mostly closeted, outside of what I do cosplay wise.

Started in my mid-to-late teens and kept to my room. Mostly was girly halloween costumes, but occasionally I was able to search through my grandmas huge collection of clothes (she was a "KMartaholic") whenever I had the house to myself for a couple hours. Not too much clicked with me though. Got my first southern belle dress my senior year of HS when I managed to convince my grandpa to let me use his credit card for an "expensive halloween costume", which he never saw... except almost did when I was prepared to show him on Halloween, but got cold feet waiting for him to get off the phone.

These days, most of my public stuff has been cosplay related, with a few non cosplay stuff. Although, my choice of clothing makes it very hard to blend in so I'm pretty much limited to any conventions I go to where weird and unusual dress up is expected so I can get away with wearing a princess dress in public. So outside of that, I'm still pretty much closeted outside of what my friends have seen from me.

[Jean. Ann]

Crossdressing has brought joy and happiness
to my life . Too bad I can not share it more
The joy has by far outweighed the
hardships it may have caused .

JAS

[Giselle(Oshawa)]

the urge to crossdress(or maybe to transistion) has made my life so difficult and i have never really been a happy person even now with a tolerant wife

[Tracii G]

Its never been a hardship being me.
I don't worry what people think so that helps.Of course I care what my kids and my really close friends think because I care about them. They all know about me.
I have had my share of hardships and ups and downs like everyone else.

[Rosie_Sometimes]

I am married and in the closet and will probably remain so. I do not work anymore due to a car accident several years ago , but my wife still does. Therefore I am able to dress whenever she's away and I use every opportunity to do so. These are precious moments to me. I have been crossdressing for about 15 years now and can not imagine life without it.

[Leslie Mary S]

Evolution of the Leslie Mary Shy plant

I am triple-retired, widower, hermit, and later bloomer.

Probably started like a slow growing mold until @1960 when I started to become a very slow growing mushroom in my closet. I started to take the form of a twig about 1990s. It was in 2005 or so when I started to grow. In about 2010 started to put forth small blooms. I am still putting out small blooms, that need nurturing. Bids and Insects do NOT come to rest on my limbs, they don't like the closest I'm in.

Attachment 305641

We southern girls all have a bit of Magnolia in us. But I also have a bit of Mountain Laurel in me too. but mostly Dandelion.

[Vintage4sarah]

My life as Sarah (when the opportunity arises) has been a journey of ups and downs. Through all of this I have carved out a niche of balancing my real life with who I really am inside. My wife and I have worked this all out with compromises from both of us.

Right now Sarah gets to emerge at least twice a month whether it be at home when the wife is away or best yet, when Sarah gets to go out to big events like FE, meet-ups with friends and just plain venturing out in the real world as a mature classy woman. Occasionally, I also get to be away for business and other hobbies and I try to make the most of it as Sarah.

[Thelise]

the urge to crossdress(or maybe to transistion) has made my life so difficult and i have never really been a happy person even now with a tolerant wife

You need to talk more honey. Why is it so difficult? What is the weight you're bearing?

[Micki_Finn]

Pretty fantastic actually... like in the most literal sense. I’ve taken up drag, have a fashion designer for a friend, and my wife loves me turning a look.

[Cheryl T]

The early years were not so great. All the shame, guilt and hiding took it's toll on me.
Once I finally came out to my wife and to my delight she was fully accepting things have been so much better. I'd love more, but that's just my nature. Now we live in an area that's not very active in the lifestyle and I long for more interaction with others who share my feelings. We go out, but not as much now as before and I'd love to change that.

[April Rose]

it has gotten better over time.

[Jenny22]

Freedom to dress daily and to go out when and where I please. Life is beautiful!

[Thelise]

Dressing at the moment staves off despair and a deeper depression. It's comforting. Without it I'd be looking for distractions. The further I push the dressing the better I feel about myself, which leads me to think it's not a kinky crutch. The types of clothing I'm looking at hint at an overall style or aesthetic that encompasses both reveal and reserve. But blimey, it's an expensive exercise! My personal style as a male is thrifty, simple, "alternative", a little grungy, and it suites growing old in my opinion. But my developing girl persona is a lot more glamorous, and more demanding of an income, which I barely have. Tricky. We have to dress smart.
Linda from TV show Becker said: "You can be old, you can be poor, but not both." Huh, I'll show her!