How did you start crossdressing and why?

[WillowWriter]

Well, I'll start, duh, hey.

When I was 10 years old a friend of mine, who was a girl, thought I'd look cute as a girl, so she dressed me up, and bam! I looked real for a 10 year old kid, I was a little guy then, and I had longer hair, so I got mistake by substitute teachers every so often. It was fun, and we did it a few more times as we got older. I think it was when I was 12 1/2 when we stopped, because she moved away. At that time it was so much fun, but I was at an alternative school at the time. I was having a lot of problems, being bipolar and all, so I couldn't say anything or I'd get bullied more, and probably get beaten up. So, I had to lay low. I crossdressed once in a while in my freshman and sophomore year of high school, but then, I met a friend who crossdressed during Junior year, and we had a little fun. After graduating from high school, my dressing needed to be fed because it was a good year since I last did it, so this winter I came out to my two closest friends. I was extremely surprised how well they took it. My friend Jo said she wanted to go shopping with me sooner or later, basically when I'm ready. So now I'm working on getting in better shape, my hair is already at a good medium length, so just need to grow it a few more months, and I'm working on getting clothes, so I'm doing a lot better than a week ago. :P My best friend still finds it kinda funny that I'm into crossdressing, but he has no problem with it, and Jo hasn't said much since, but she is really good to me. I love them both. So...how did you start?

[AlannahNorth]

For me it was a long slow process. I was about 8 when I developed a real interest in feminine undies about the house, and things like earrings. I indulged occasionally as the years progressed, purged a couple of times, and only really got interested once my wife and I separated, years ago. It was an opportunity to try things in my own home without a chance of being surprised. Well, it led me to a new hobby! I've been laying low for about the past 5 years, but am now again enjoying things like skirts at home.

None of my friends know, it has to stay that way - a fact of reality for me here.

[WillowWriter]

Alannah, That's something. I'd be soooo much harder on me if I could tell at least my closest friends. You are strong, that's really good. You're lucking that you have free range with dressing, I'm not so lucky, only in the mornings for me. Mom and brothers go off to school and work, but I shouldn't complain.

[diannecourtney]

Oh, I got started much later in life, although there may have been hints as early as mid 30's when I found some spandex mens briefs. Wore em out and went to wife my girdles. Oh a time went by and the wife threw out her still lovely wedding truso - I travelled and they became wonderful nighties for a few months or so. At which time the Nehru look came in and the kid got 2inch heels. Well they died and eventually I saw a pair of ladies leg that I could die for and w/o knowing it I began to CD and find the forum and 3 yrs later the wife said she wasn't interested in a lesbian arrangement and cashed in the marriage. It has been fun ever since.

[Roberta Marie]

Willow,

First, to answer your question, the first that I can remember, I was somewhere between 6 & 9 years old and our family went to a cousin's wedding. Between the ceremony and the reception we walked to another cousin's house to change from our "church" clothes into some more comfortable (and durable) clothes. We were changing in my my older cousin Kathy's bedroom, and she left a pair of her pumps lying on the floor. For some reason I tried them on. They fit, both physically and mentally. Since then it's been a long (45+ years) road to self acceptance, but I'm finally starting to feel good about myself. I can't help but wonder how different things might have been if I could have had some help in figuring this out when I was your age. I think you are great for having the courage and insight to be who you are.

Second, I think it's great that you are finding some acceptance and understanding from good friends. Even more so, I think it's great that you were able to come out to them. You are awesome.

[WillowWriter]

Thanks Roberta, I'm glad you said that. You really made my day, thank you! I didn't have much of a childhood(Really rough life since I was 6 or so) I'm very big into knowledge so I looked stuff up everytime something felt weird or different about myself. Since I've been crossdressing a good while, I've managed to put a character into my book series(I'm a big time writer, plus I wanna get published one day) who is a crossdresser, and I like his character, very unique like myself, but I'm more like the main character, Kaz. Anyway... Thanks you for the compliment.

[AlannahNorth]

So, your situation has you exposed to some risk. Well, I can tell you one thing: the day you really let your guard down is when someone will walk in unexpectedly! I'm sure of this to the point that I would put money on it. That is something only you can decide for yourself, whether to be extremely careful and vigilant, or to be found out. What would happen if you were? If you search the posts here (they go back a long ways) you will find topics that may lead you to discover (carefully) how various family members would react.

I often read of CDrs who seem to want to be 'discovered' and pursue behavior that will eventually lead to this end. I don't, and so I only dress when the situation is suitable (read SAFE). Once again, not my preference, but a necessity.

Being strong is often not a matter of choice. If I could go back in time with what I know now, my life would be very different. I would not likely be as strong, but my life would have been so much better. However, I do not have that choice, and I rarely ever sit there and wish it was all different - it would be a waste even more time.

So while I'm inside I indulge to some extent and enjoy the experience. Enjoy your mornings - and someday you will enjoy remembering them!

[AlannahNorth]

Willow,

By the way, you have something I've never yet experienced - you share this side of yourself with two (TWO - in bold) of your friends. That is FANTASTIC!

[WillowWriter]

I see what you're getting at. I understand what you mean. I shouldn't let my guard down lower than it is now, so I'll take what you said and keep it in my head. Thanks.

[WillowWriter]

Thanks Alannah, I try and be open with those two. I was really starting to kill me inside, always hiding stuff from them.

[Kim Welcher]

When I was 3 I had to wear some girl's underwear for some reason out of my control. Later on whenever I saw a show on television that featured a male wearing female clothes (like Bugs Bunny) I would catch myself asking "what would it be like to dress like a girl?" Some time when I was in seventh grade I waited till I was the only person in the house and tried on one of my mother's dresses. I've been dressing secretly ever since.

[WillowWriter]

That's cool Kim. Yeah, Bugs Bunny often crossdressed I noticed. It's great when you're all by yourself and have the freedom to dress up and have some fun. I stay upstairs, our main floor has too many windows. :P

[Roberta Marie]

If I could go back in time with what I know now, my life would be very different. I would not likely be as strong, but my life would have been so much better.

My life would definitely be different if I knew then (when I was Willow's age) what I know now, but I'm not convinced that it would be better. I have to wonder if I would even have met my fantastic wife or if we would have had our fantastic kids and grandkids. I've had a great career, and I'm currently in my second great career. Sure, it's taken me a long time to come to understand and accept who I am, and it's been, at times, a difficult journey. But it's been a journey that's had a lot of great times, too. And without both those difficult and those great times, I would not be the person that I am now, the person that it has taken me this long to accept.

To be honest, I don't know that I would change a thing in my life. I'm pretty happy with the way it's turning out.

A couple years ago I attended a Transgender Day of Rememberance. One of the speakers was a young transman who said something to the effect that when people ask him about being born in the wrong body, he replies that he was not born in the wrong body. Rather he was born in the body that God intended for him to be born with, so that he could make the journey that God intended him to take to become the man that God intended him to become. What he said gave me a whole new perpective from which to look at my life.

[joannemarie barker]

I was 10 or 11 when I saw my sisters one piece swimsuit hanging over the bath to dry.I tried it on and bang.I must've gone to the bathroom 15 times that day after that my sisters room was so much more than a bedroom

[zenfirefly]

Women's clothes are so much better than men's clothes. That's the bottom line. I started crossdressing when I was 16. It all started when I tried on some of my mother's old dance wear. Leotards, tights, stuff like that. I don't know what made me think to do this but I've been wearing women's clothes on and off ever since that day. Over the years, my desire to wear women's clothes has progressed. I've gone though many phases where I wanted to wear women's clothes, then I didn't, then I did again. In the end, the urge to wear women's clothes has won. As of January 1st 2011, I wear nothing but women's clothes. I do not own any men's clothes. It has been an interesting process. I have a lot of respect for everyone who shares their crossdressing experiences on this forum. It inspires me to continue to live my life the way I want to despite the expectations of what one should or should not wear.

[tinalynn]

I started way back in single digit age (4, 5?), when my older sisters dressed me up for fun. I remember trying on their clothes and my mom's clothes from age 10, or so. All I knew was that I loved wearing hose, heels, and dresses/skirts. I like the way they looked on me and how the felt/made me feel. I started going out when I was in the Navy, very careful not to be caught. (I would drive 100 miles just to get away from anyone that might see me.) On my own after the Navy, I dressed at home and went out as I pleased. It was great! But, looking back, I really wish I would have done more. I was very self-conscious about it when I should have explored it and learned so much more. The old adage 'if I knew then what I know now' sure does make sense! Now, being married with a son 2 months away, I can dress at home because the wife is okay with it. But when I travel for work, I get lost in the pink fog almost to the point that I can't wait to leave work! It is so much fun shopping, trying on cloths and shoes, and just plain walking among the living as a woman that I can't wait to go out of town! Odd, really, since I also love being at home with my wife...

So, Willow, take advantage of what you have with your friends now. Go shopping with Jo. Explore, learn, try new things... You may not always have the opportunity to do this, but you have it now. But please do be careful while you explore - understand that, in time, your friends may find it a bit too much. Work with them and they'll stay friends.

[Rachel Lea]

When I was 13 a friend of mine was dressed a a girl by his sister for halloween. I thought it was so cool, I was jelous, I wanted to dress that way. Then I found a pair of my mom's pantyhose in the basement tried them on and I was hooked, they felt great. After that I stayed home for family vacations and played with clothes all week. But at that age I did not stay in them long always thinking I would be caught. What I know now I wished I had been caught I then I could have come out.

[Foxy Lady]

I was 9 or10 and mom had a Playtex OBG laying out and for some reason I had to try it on. This went on for about amonth when she caught me. Instead of getting upset the next weekend from Friday afternoon to Monday morning I was dresses as a young lady. That was over 50 year ago and still hooked.

[Marge]

the first thing that got me started was moms one piece swimsuit i tried it on and felt so good couldnt believe how great if felt been crossdressing ever since.

[dana8656]

goes back to my early years, parents gave me a book "Everything you wanted to know about sex, but were afraid to ask" (my sex education), there was a section in the book about crossdressing, some boy put on his mothers angora sweater and how it felt, I just had to try it, and I liked it.

[KellyCD]

It's been over 20 years since I started so I'm trying to remember back that far....so if my memory serves me correctly...

I was 7 years old and my older sister who by the way looks like Rebecca Romijn's twin, was staying at our house and I remember seeing some of her clothes and was awestruck by them. I didn't wear underwear anyways (much fighting was done between my mother and I for that) but once I saw my first set of bra and panties for some reason I was compelled to put them on. So I snuck a bra and pair of panties into my room and tried them on and instantly felt comfortable. I looked in the mirror and thought I was "pretty". I had already knew at the time that "boys don't wear that" kind of stuff, and it was widely regarded as "gay" and "only fags do that" (I was born and raised in Kentucky).

[Veronica Lacey]

Hi WillowWriter...

As a young child my parents, brother and I lived in a rather small abode, a two bedroom 1,000 sq ft rancher. My brother and I shared a small room and each had a separate single bed; mine was pushed up against the closet. The closet my folks had was too small for all of their things so my mother hung her dresses and other items in the closet in our room.

Low and behold, over time I would find myself reaching into the closet to feel those soft, satiny dresses and just loved the feel. I would occasionally crawl up inside the hanging garments, enveloping myself in the satin or nylon and rayon. I felt very comfortable. I was about 7 when all that began.

When I was nine we moved into a larger house and I had my own room. I soon found some of my mother's old nylons and panties and, in my new-found privacy, I began the journey that has lead to where I am today.

Indeed, I occasionally ponder whether or not I would have engaged in dressing had my mother not had her clothes in our closet. There will never be an answer for that. Ah well.

Good for you for being yourself with some friends. I believe that life will not be so cruel to you as it has been for others who cannot find the means to come to terms with themselves and current family.

[Kate Simmons]

I started wearing my Mom's clothes. I began to have feelings that my generation inferred that only girls should have. I felt I had no other option but to look like a girl as much as possible to "legally" have those feelings. The rest, as they say, is history.

[susan2010]

The first time I remember I was 4 or 5. I snuck into my sister's room, took off all my clothes, and put on her white petticoat. Looking back on it I don't think that was the first time I did it. That was about 50 years ago.

[Lucy_Bella]

oh boy!!.. If the walls had eyes.. I would say my earlist memories of xdressing started around 3ish.. It was when my lil sister was over one years of age.. For punishment , my stepfather use to dress us up in her clothes and I mean even the panties at family events when we acted up.. I use to dress in them even after , suppose I didn't know any better but was caught doing it by my mother..

Every since then it has always been on my mind..