In what ways did your mom encourage your crossdressing?

My answer is a very confusing yes and no. As a small child, I would dress in my mom's shoes and walk around the house. For the first few years, there were no issues and she did not say anything and actually enjoyed it. However, as I got older she started telling me that a boy wearing womens shoes is wrong and began punishing me for wearing her shoes. Therein lies the confusion.
Unfortunately, I did not stop. On another post I outlined the first time I was caught wearing her clothes and the subsequent "talk". I got the usual "boys wear boy clothes, girls wear girl clothes, do you want us to dress you that way for school?" talk. I was caught and chastized several times afterwards. Mom would regularly search my room for clothes and each time would confiscate and throw away my clothes. She even went as far as searching my car for clothes on several occasions. If I owe anything to my mother in regards to my transvestism, I would have to say that she helped me learn how to hide my clothes well and how to look at all possible scenarios that would result in someone uncovering my stash. I hide my clothes very well now.
What I can also credit to mom was my fascination with womens clothing. Silk panties and bras, pantyhose, high heels, dresses, skirts, and silky blouses are all items that I still enjoy wearing to this day.

I guess the best answer I have is what could be called Passive Acceptence....My mom had an innate ability to show unconditional love for her children...I don't care how badly my Brothers/Sisters or I messed up we knew Mom still loved us.

She allowed us to grow up and become individuals and make many of our own choices....now the other side to this coin is that we also learned to live with the consequences of our own decisions and actions and this was difficult for several of my siblings who have had their share of run ins with the law...for while Mom and Dad allowed us the freedom to explore...they would quickly inform you that if you got into trouble with the law and were thrown in jail for your own stupidity...don't bother calling home expecting to be bailed out..it just didn't happen.

Like all Mom's...Mine knew that I snuck her shoes out of the closet she never confronted me with this in a manner that would have perhaps embarrassed me or stifled my exploration...so I guess you could call this encouragement of a passive nature.

Mom didn't "Officially" condone it, but she didn't do anything to stop it either. It was a don't say/don't tell kinda thing. That said, a stray pair of my Sister's panties would show up in my underware drawer sometimes...on one occasion I felt guilty about wearing them I went to put them back in her drawer where they belong...and they were already there. My mother had bought me my own (half a dozen pair or so) and was "slipping" them to me. Mom had two bikinis that I would sneak out and wear in the pool every now and then. Years later I realized that if they fit me there was no way they would fit my mom...she bought them for me. I had a "stash" in my closet (couple of bras, panties, clothes etc). When they were first found she piled them on my bed... I re-hid them. Soon after, they were back on my bed...cleaned/folded. I re-hid them. She found them again and this time put them in my dresser drawers where they should belong and hung my one dress, two tops and skirt in the front of my closet (where they had to be seen everytime you opened the door). But in all this she never said a thing waiting for me to bring it up I would emagine but I never did.
She always bought my clothes till I was out of high school and to this day I'm pretty sure most of them came from one or two trendy girls clothing stores in the area. They wern't obviously "girly", just plain tops and pants. I found this out shortly after I got my license. She broke her foot and I was driving her around while she healed. We stopped for something for my sister at one of these stores. While she "shopped" I was wondering through the racks and on one of them was the top I was wearing and an adjacnt rack the same royal blue pair of cordoroy pants I had on (zipper had a 1" ring on it and pulled down instead of up...I loved those!). On another rack was a pretty pesant blouse in a baby blue satin/poly. Feeling rather brave, I found my size and went into the changing room, put it on, then went back out and showed her. Her only comment was "If I buy it, your wearing it to school". We didn't, but in all of it it was her way of saying I love you anyway...

Jenn

Mom not only didn't encourage it or support it, she went bat-shit crazy when she found out when I was in high school and brought my dad into my room for "the talk" and the two of them made it their main focus to have me accept Jesus as my personal saviour and acknowledge crossdressing, as well as masturbation and premarital sex, was a huge sin and I would burn in hell forever if I didn't change my evil ways. Thanks to my parents, I enjoyed religious guilt for a few years of my life, but then I discovered "celebrity" and easy women, alcohol and swinging. So, thanks to my mom's freaking out, I was not turned into a religious prude, but rather an irreligious explorer of life and cognizant of a greater power than some man-made religion.

(sorry, next post will be shorter... LOL)

I too was supposed to be their first girl "Amanda" lol. Guess they kind of got their wish, though despite a lot of disappointment, a therapist and me coming home to all my stuff packed and my small (hidden) wardrobe laying on top of it...I think they assume I stopped once I moved out. Guess she didn't help much haha. She always refused to support it

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Originally Posted by Mikka

My mother did not encourage me or ever let on that I was raiding her closet. She must have known especially in the summer during my early teen years when I would stay home by myself and wear her clothes all the time. I could have never put everything back correctly where I found them. Mother probably knew but never said anything except for her comments on what nice legs I have and that most women would kill for legs like mine.

Mikka

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Yes, I wasn't really good at putting the clothes back and my mother still says I have legs most women would want. I'm not sure they're *that* good though. Wish they were.

Kind of sort of . When i was younger her closet was overflowing so she started putting her clothes into mine which eventually, curiosity killed the cat and i started trying them on .

"How did Mum encourage my cross dressing?" I'll say "indirectly"

She never dressed me up nor put on a single item of clothing. Instead she planted her ideas of what is perfection (Feminity) and what is evil (any thing male).

She held out the feminine form out as the ultimate vision of perfection. To Whit, when introducing the sibs to her friends, she would say "here is xxx the eldest, then came Kat, finally came my success story (my sister) zzz". Even the 3YO me could figure out the equation "If new sis == success, then brothers == failure".

Yes, she introduced her sole daughter as her success story leaving the unsaid implication that her sons were her miserable failures. This assessment has been reinforced in her senior years. Her granddaughters could do no wrong, while her grandsons can go pound sand.

You may think I exaggerate, but I assure you, I am pulling my punches. I sooooo want to go on about my feelings about the woman that bore me (I won't call her "Mom" as that suggests a relationship that never existed). Understand instead the effect on an offspring desiring to please a supposed-parent. Said parent praises the female form over all other. IMHO this is the best explanation of why I CD today. The desire to please a parent I could never please due to incorrect hardware.... She's dead now [cancer] and it's no relief. I Yam what I Yam,,, And I still want to piss on her <del>grave</del> burial site

Note to self... piss on here grave while in town next.

I started wearing her panties and slips very young.At puberty I too left "seminal "evidence on them and while I thought I hid her things well in my room they also were found.She never mentioned it to me even though I continued to take her things and wear them until I left home after graduating from high school.I do remember when quite young she dressed me as a girl and perform on stage as part of ballet lessons I was taking.I guess in a subtle way she encouraged my cross dressing.

My memories were locked away until I came to this forum. Something that I suppressed or simply had forgotten over the years.
I can now recall Mom putting nail polish on me at least once. She made me up on more than one occasion, replete with the reddest lipstick.........
I can still see her smile of approval and wish I could go back and experience it all again.

she did by buying me women's cloths when i was 15 and she also supported me after i told her i was gay.. Love ya mom...

I won't say she encouraged me, but she didn't discourage me either. About kindergarten/first grade she dressed me up as a witch. I remember she hand made the witches costume from a pattern, so it was a lot nicer then any regular commercial costume. There is actually a photo of me in the witches costume.

She also taught me a lot of more feminine crafts like sewing, crochet, needle point, etc. I got to point where I had actually sewn my own down coat, I wore to middle school/high school. I was easily the best in class in freshman home ec sewing. Now project runway is my favorite show on TV. I regularly discuss who should win with my wife.

Then 40 years later when I was recovering from bypass surgery, I came out to my mom about cross dressing. She didn't seem surprised at all.

My mother made dresses to sell to neighbor girls when was I around four years old. When she wanted to make the hem she would put the dress on me and have me stand on a chair so she could place straight pins to make the hem even. Sometimes wore dresses out to play with the other kids. Of course was teased by those kids. My father didn't know as he was confined to a Tuberculosis ward in a hospital for three years. I don't remember if she had me put on girls panties then.

Later after divorce those memories of my childhood came back. Started wearing panties and slowly added bras, garter belts, nylon stockings, slips and full female dresses or blouses and skirts. Now retired and stay mostly in my apartment when I dress in female attire. To many other tenants don't feel it is 'normal' for a male to be out in the public view in the building wearing female clothes. Although the building is non-discriminatory, one can not control what others may judge oneself.

My mother caught me wearing a dress when I was about four years old. She didn't yell at me but as she removed the dress she told me that boys don't wear dresses. When I asked her" why", she just said," because". Then one time when I was about ten she needed to know if a party dress would fit a girl in my class. I told her that Connie was my size. So, with my sister watching, my mother tried the dress on me. It fit wonderfully. But Connie got to wear it after that. Leanne

My mother didn't actually encourage my crossdressing, and I never officially came out to her as a budding CDer, but I'm sure she had her suspicions as I would often try on her clothes and shoes when the opportunity arose (I was a latch key kid). I always covered my tracks as best I could, but I am sure there were the occasional slip-ups - sometimes stretching out her shoes, and in one case actually putting a (never explained) tear into one of them come to mind.

Looking back, I think she might have put out the occasional tentative feeler to see if I was inclined in that direction, but I didn't clue in at the time. Of course, I always protested at any suggestion that I might have a "girly" side to me since that was what boys were supposed to do. One incidence which comes to mind was when I was about 9 or 10 years old and she bought a party dress - ostensibly as a gift for my girl cousin who was the same age I was - and asked me to try it on to see if it would fit her as well, as we were about the same size at the time. I protested vehemently of course, but deep inside I felt pure ecstasy over the experience.

Another time was when I was a teenager, and she made a point of drawing my attention to a newspaper article on Thailand's katoeys (ladyboys), thinking that I might be interested in reading it. Needless to say, I lapped it up while feigning only a passing interest in it to keep my "secret" safe. Then again, we're talking the late '50's/early '60's here when there wasn't much information out there about transgenderism, and what little there was painted us as fetishists and deviants. In fact, people were still coming to grips with Christine Jorgensen's sex change operation, which was a huge sensation at the time.

I also distinctly remember developing a fondness for embroidery when I was a pre-teen. I don't recall how I managed to get over my hang-ups in admitting to liking such a "girly" type of activity in pursuing this hobby, but I do remember my mother being very supportive of it and constantly praising my efforts.

I've often wondered how things might have turned out had I admitted to my mother at the time that I enjoyed wearing girls' clothes. I was an only child, and she might just have enjoyed having a part-time "daughter" as much as I would have loved being one. But she has passed away now, and we will never know...

My mom never forced me to wear anything, but she did dress me as a girl for Halloween a couple time, mainly when I was younger. When I was little, she gave mean old net petticoat of hers to wear when I wanted, and when I was may 9 or 10, she loaned me a pair of her sister's nylon satin pajamas to wear (we were storing some of her younger sister's stuff for a while). About that same time (I was her size at this time, so her clothes all fit me perfectly, I knew from dressing in her clothes on the sly) she wanted to totally dress me as a woman for Halloween with plucked eyebrows, full makeup, stockings, high heels and everything, but I foolishly chickened out. I've regretted that ever since

Carol

My mother made no secret of the fact she wanted a girl. I suspect she dressed me as a girl from the time I was born. I've seen pictures of myself dressed in girl's clothes when I was little. I got to wear boy's clothes when I started school but my mom was continually having me try on girl's clothes that she made. I don't know who she was making these clothes for but I now know they were for me.

When I was 8 I got a little sister and she never dressed me as a girl again. I didn't need any help after then anyway, I did it on my own

I would not say she discouraged or encouraged it. I had a Shirley Temple hair do until I was 5 (that was my first hair cut). I also played with two girls across the street and we played dress-up. We also put nail polish on our nails. I didn't get any negative comments from my mother on the dress up or the nail polish. Later I discovered here underwear drawer. Anytime I was left alone I would try things on. Once I heard her saying to my father, someone as been in my drawer again. But nothing was ever said to me. I just became more careful to put everything back as I had found it.

Happy you, if your parents go along, my mother can not deal with it and rejects it extremly :(

Yes she was a big influence. She tossed me out so i was free to dress any way i wanted too lol

My brother used to say when i was very young my mom put me in a dress for a photo. Ive seen the photo and it was probably shorts. My mom always said it was shorts. But he mentioned it many times. Ive often wondered if my embarrassment about that teasing led to interest in the subject. That is important pyschologically. Hair of the dog that bit you.

You are too hot to be Cd

There goes Kelly teasing poor Seanmuscle AGAIN..! LOL

My mom, from the time my sister was born, made it very clear that my sis was wayyyyy more important than I. Then when I tried on the shapewear and pantyhose I got the "talk". When I didn't stop I was punished. Then when I moved out I wore what I wanted. Turns out I still like pantyhose/tights, shapeware, and pretty much anything feminine.

She always said that she wanted a girl and once she put me in a dress, when I was about 7. She said (or pretended!) that it was a present for her friend's daughter who was about my height and she wanted to check it was the right size. I loved it - I didn't want to take it off! And I also loved trying on her very feminine clothes and underwear when she was out. I so wish I had been born a girl!