An interesting question

[Joansometimes]

I don't know if this has been asked before, if so I'm sorry.


Ok here it is. say when you were between 5 and 15 your mother caught you dressed up in her or your sisters clothes, when she started asking you all the questions and recieved all the answers she decided to ask you something. She asked you if you would like her to take you to a mall out of your area where no one would know you yo go and buy you some girls or womanly things.
Would you go with her?:daydreaming:

[Aubrey Skye]

Very interesting question. Looking back at how I was at that age I probably would not have gone. I honestly wasn't sure who I was back then and I only started dressing at 13. So probably no. But it definitely gives some good for thought about what would it have been like that have gotten that question. Can't wait to see some more posts on this. Good question!

[Natasha V]

Hi Joansometimes that would have been a dream come true i always enjoyed looking with envy at all the pretty things girls/women had. I would have really enjoyed being tought by my mom how to properly dress and learned girly mannerisms. Sigh , but that was never gonna happen.

[Mollyanne]

Actually my mom did indeed "catch" me dressed in her lingerie and we did talk. She actually asked me if I liked how I was dressed and I answered her honestly and YES. she then told me that I needed or wanted her help all I had to do was ask. And I did ask on some occasions. BTW, if she asked me to go to a mall to buy some feminine things I would have jumped at the chance. My mom kept our secret and took it to her grave.

Molly

[Teresa]

It would have been a case of over my Father's dead body ! No way would have that happened unless used for a punishment !
Besides there were enough clothes from various sources to keep a young CDer more than happy !!

[Jocelyn Quivers]

Actually my mother did ask me this question, but in a more stern/disapproving tone! In all reality even if she asked it in a more approving, supportive manner, I would have still denied everything and state I was simply "curious" or use some other wacky reason for wearing her clothes. Instead I would have asked for to take me to the mall to buy more video games.

[Jaylyn]

First of all at around age of twelve to fourteen I loved getting into moms hose and girdles. She has told me that she caught me more than once sitting in the floor rubbing her legs when she was wearing hose. She wanted a girl so bad for her first child that she had actually sewed several flour sacks together for the dresses. We didn't have malls when I was a kid and by the age of twelve dad had me doing men's work around the farm, so mom would not have ever asked me if I would want to dress like a girl. My sister came along and she got what she wanted, someone she could dress in frilly clothes. I always felt left out, after sister was born. I still had my stash of Sears and what was Montgomery Wards Catalouges to look at and wish though. After dad put a stop to mom dressing me in those dresses she sewed and dad taking me to get my blond curly locks burred off my girly side became pushed down deep inside but still I secretly watched when a woman would apply her lipstick or mom would dress and something inside of me would stir the pot of my feminine side. Long answer to get to no I would probably have not gone with her.

[Tina B.]

Would have been interesting, but being a child of the 50's a thing like that was unthinkable. Actually, I was caught one day by my father, a trip to the mall was not in the offering, but I was offered a trip to the woodshed.
It was made very clear to me this had to be a one time only, getting caught a second time, would have been detrimental to my health.
I stayed very deep in the closet after that day.

[laura.lapinski]

No, I would have been too embarrassed to admit to wanting to take it that far. I would have never dressed in my sisters or mothers clothes. CD is a type of sexual thing for me, and their clothes have too much psychological connection to them, which would have made it seem icky to me. I'm not criticizing others who did use their mothers/sisters clothes. I realized that CD is different in each of our minds. For many, it has nothing or little to do with a sexual thing.

[BillieAnneJean]

No.
I did not discover CDing until late in life.

[jennloves55]

I would have went in a heartbeat.

[Beverley Sims]

Being very young, that would have been a big opportunity lost for me.
I feel I would have regretted it to this day.

[Sarah Beth]

I did not have a sister and I would never have dared to put on anything that belongd to my mother. If my mother would have ever caught me dressed it probably would have been the end of me. I was a teenager in the 60's and there weren't malls in those days either. The bulk of the clothes I had in those days came from a trunk full of things left behind in a house near ours where the people moved away and left a bunch of stuff.

My biggest wish would have been to have had someone catch me at it who would have been that understanding and could have helped me at that age learn about being more feminine. By the time the time I was 16 I was so disgusted with myself of my urges to dress, and of course with rampant teenage hormones all that went with that, that I started doing what I could to seem more macho.

[Tiffany B.]

Back in the 60's was the first time I remember discovering my moms undies... They felt so soft and silky, that I just had to try them on and I didnt take them off for awhile... I remember one time leaving our house to visit Grandma and my mom saw that I was wearing her panties due to a hole in the seat of my pants.. From what I can remember, she turned to Grandma and screamed out an embarrassing comment about me wearing them... I ignored it and continued on my way and another word was never spoken...

However sometime around that time, my mom tried to talk to me about sex... and I just remember that I said my pecker would get all tingly when I saw people kiss on TV...

To answer the question... If my mom offered to support and help me back then..... I would have to say no... First I was way too young to understand what was going on.. and next, we're talking the 60's and 70's and gender bending was not socially acceptable back then... Now if you asked me what I would do today, I'd totally jump at the chance... :)

[bridget thronton]

Yes I would have gone with her (but I was not caught wearing her clothes)

[Isabella Ross]

No...I was completely mortified with the thought of anyone knowing "my secret", and being from a small, redneck town in Canada, it just would not have been possible.

[Stephanie47]

When I first tried on one of my mother's nylon slips it was strictly because of the feel of the fabric. I cannot remember any other article of clothing back then that would have been of nylon. I loved the feel. Of course, to fully enjoy the feel of nylon I had to try the slips on. I was too young to apply any sexuality to it. At a single digit age in the 1950's sex did not exist. Later as a teenager I started to dabble in my mother's lingerie draw. Soon I had expanded my interests to her panties, stockings, girdles and dresses. By that time sexuality start to arise. This created great conflict in me. I went into a period of self loathing. I detested wearing women's clothing. Back in the 1950's and 1960's to dress as a woman surely meant the male was a homosexual, which was not a good thing back then. I could not reconcile feelings for girls and dressing as a girl.

As to my parents? If I had been caught, they would have beat the shit out of me. I remember an instance when riding in a car two men in the car in front of us were sitting close together (bench seated car) and obviously romantically involved. My parents expressed some really negative thoughts on gay male sex. Another time while waiting for the Staten Island ferry we saw from the rear a person with long beautiful hair down to the ass checks. The person turned around and it was a bearded guy. Damn, beatniks is what he was called. Absolutely no tolerance for any expression of individuality.

Once I was almost caught. If the security chain on the apartment door had not held against my father trying to break it, I would have been caught in one of my mother's dresses. Once I let them into the apartment I could see their rage. I told them I was on the toilet, etc.

So, I would not have taken up an offer to get my own clothes because I seriously had doubts about my sexuality and was into a period of self loathing.

[Andrea Payer]

actually my mother caught me with one of her bras when i was 16. we talked about that but she didn't ask me this particular question.
maybe i would have said yes. maybe not. i can't answer that.

[stephNE]

When I was 5, and maybe younger, I loved putting on my mothers things. Our neighbors all had girls, so I played with them often, and a couple times they dressed me up in their clothes. When my mom caught me, a couple times she laughed at me. But later, maybe 8, 9, 10 years old, when she caught me she told my what i was doing was wrong, and if kids at school found out they would call me a sissy, and beat me up, and things like that. So at age 5, I would have loved a girly shopping trip. At later ages, no. My wife and I go shopping together now and it is wonderful.

[Kate Simmons]

Only if my Mom were serious in helping me to become a young woman. Then I would have embraced it. :)

[Rachael Leigh]

I would have been scared but I think I would have done I for sure it would have made me feel normal

[ShelbyDawn]

My initial reaction to this was that would be no way in creation that my mom would ever be that compassionate. And then I remembered that she caught me sleeping in my sisters panties once, she ripped the covers off because I wouldn't get out of bed. Shortly after that she started buying me men's bikini briefs instead of tighty whities...

I guess she was more understanding than I give her credit for and now I kinda wish she had caught me in the prom dress...

By the way, I think I would have taken her up on the offer. No telling where I would be now if it had happened...

[Mia27]

Haha, i use to always dream my mom would do that for me:P My mom is very anti-trans and anti-gay. She would kill me if she found out i was bi and a CDer!!! So if she asked me to go shopping, i would say yes!:)

[Terry V]

I was asked a simlar question many years ago, "if I wanted to dress as a girl" since she caught me trying on her daughters panties at the time I said no but after a couples of days she asked me again and I said yes I would like to see myself all dressed up. I was about 12 at the time and she told me to come back the next day and she would have something for me. The next day I went and found myself dressed in an Easter outfit of my other cousin and when I looked at myself I was shocked to see me as a pretty little girl and since that day I loved the look and the feeling of being dressed now as a woman. In the beginning I just knew something was wrong with me but my Aunt keep telling me if I like it what harm would it do and I found out she was right. After all these years I still feel good about it with no regrets

[~Joanne~]

I never got caught in mom's things because I never wore her (or my sisters) things. I actually started out with my own pair of Pantyhose. My Mother use to sell them and had a box full of free samples. So I stole a pair (or two lol). Now had she caught me and offered a trip to the store/mall I would have most certainly said No. Matter of fact, I would have been begging her not to tell anyone.

[natalie_cheryl]

Inner me would scream yes! But I probably would have said no

[Tiffany Jane]

As I went to every measure to not get caught when I was a kid, it was my own get away from the things that have bothered me. In a lot of ways it was an exploration into my sexuality in my teens as well. So no. Didn't want to be caught, didn't want to be questioned about it, didn't want to be punished for doing something that felt as much a part of who I was. Today, my wife is the only one who knows, and although I would like to be accepted for every part of my being, know enough of my family would make the desire to dress a heartache and a negative experience.

[Kim_Bitzflick]

I know that would NEVER have happened because she did catch me one time in a bra that I had purchased on my own. I received a VERY LOOOOOONG lecture and made to feel horrible about it.

So I can't even imagine something like that happening.

[JayeLefaye]

Oh good heavens NO!...But I only dressed once in a pair of my mother's panties when I was about 7, and it's a long story of what prompted it, and there was no interest at all after that until I stumbled on my sister's "things" in the family laundry hamper when I was 15(?), and raided her clothes for the next 3 years, and when she moved out, I was dormant, secret, ashamed, un-knowledgeable, for a long long time.

So I would have said "No" to my mother, because I was ALL BOY, and had no desire to dress in girlie things...But if my SISTER had caught me and made the same offer, in a supportive way, then I'd've probably said "Yes", so long as we could keep it a secret, and gotten a big heads-up as to my feminine side...But I don't know if that would have been a good thing or not...

Happy ending, so no complaints.....But interesting question.

Jaye

[Kris1775]

Probably not at that age. Now I would.

[Laura28]

Hard to say what i would have said, i did were her things i often wondered if she ever new if she did never said a thing to me. I think i would have said yes to see what it was like to be fully dressed, it wasnt till my late 40's that i started to dress fully Wig forms etc... when i think back of all the time i could have dressed i regret it. Now my wife and i shop and she is very supportive, always has been and we have been married for thirty years.

[DebbieL]

I don't know if this has been asked before, if so I'm sorry.

Actually it's a great question, and the answer is important.


Ok here it is. say when you were between 5 and 15 your mother caught you dressed up in her or your sisters clothes,

I was 6 years old when she caught me. I was wearing her slip, her girdle, her bra, and her dress. I'd locked myself in the bathroom, and she needed to go, so she used a hanger to pop the door open.


when she started asking you all the questions and received all the answers she decided to ask you something.
She asked you if you would like her to take you to a mall out of your area where no one would know you yo go and buy you some girls or womanly things.

She did have that conversation, and I told her flat out that I wanted to be a girl.
She did offer to take me shopping for girls' clothes.


Would you go with her?:daydreaming:

I DID go shopping with her. She bought me some pretty blue tights, a skirt, and a pretty blouse. She was on a really tight budget so no shoes.
I was on top of the world, I wore the outfit as much as I could, even slept in it sometimes. I wore the tights even after they were so laddered they looked like cob-webs.

Unfortunately, she was seeing a psychologist at the time, and when she told him about her new daughter, he told her that she should not encourage me and hope I grew out of it.
Mom knew I was dressing after that, and at one point confronted me for stealing some of her clothes. She start supporting me covertly by taking me shopping with her and helping her pick out clothes.
We were the same size and after she'd worn something I'd picked for her to work or church a couple times, she would put it in the "charity bag" which meant I could have it.
She even found excuses to buy a wig that was my color, and a pair of boots she could barely put on - that fit me perfectly.

At the same time, both of my parents tried to get me to accept being a boy as much as I could. Back in those days, transition wasn't an option. Even HRT wasn't an option.

[Madilyn A.]

Since I was never caught, this becomes a strictly hypothetical question. If caught "red handed" dressed where I would have no way of fabricating a story of this isn't what it looks like, then I would absolutely take the ride and be all the girl I could be. But if Dad or older brother found out.....oh my !!!!!

[Maria 60]

Good question, and I don't think its ever been asked. I don't think so, I was always in denial with my dressing, it was always "this time is the last time I am going to dress", even when caught red handed I wouldn't admit it. So I don't think I would go for it. Even though I would have loved it.

[Gillian Gigs]

This might sound odd, but I sometimes think that I was caught, but didn't know it, and was never confronted about it. I used to raid my mothers lingerie's drawer and there were several items that fit smaller than most. After awhile they disappeared and showed up in a dresser drawer that had never contained lingerie before. These were the items that I wore the most, as they fit me the best. Was it a coincidence, or did she know and was separating these items so I wouldn't make a mess of the rest of her things. She also moved several dresses to a down stairs closet, and the basement was basically my domain. In that closet were drawers in which she also put other old lingerie items. So why weren't they just thrown out??? Maybe she knew and just let it be her little secret, which she took to her grave. Who knows, it does make me wonder.

[Andy66]

Im glad you asked this queestion, Joan. Im grateful to be able to read all the different points of view because I happen to have a fourteen year old son who seems to be trying to figure himself out. The other day he asked me to get him some over the knee socks, then he changed his mind. I gave him my usual answer that I give about clothes: okay, if its not too expensive. I think he wants them, but hes just kind of shy about it.

[Kelly Greene]

To answer the question, If I knew then what I know now I would have loved the option of getting my own feminine things and exploring where I belonged in gender. In 197x when I was in my preteens and I was caught, I had zero understanding of what I felt and I think my parents were just as ignorant about all thing cross dressing / transgender, so the result of my being caught was me being given a model of a sailing ship I and being told to NEVER do it again. ( I never finished that model, and I never got caught again, which means I have never been able to resist the draw to the feminine.)

[Diane Smith]

My mom actually did take me downtown to a major department store and bought me my first pair of heels when I was 12 (in 1969). I was also wearing red lips and nail polish, and gold pierced earrings by that time. Must have been a sight for the SAs and other shoppers.

- Diane

[Melanie B]

I must have been about 8 or 9 when I was caught wearing Mum's bra and girdle, and a bit older than that when I was (rightly) accused of breaking the zip on a pair of her boots. But I was never given the option of a shopping trip...and although a visit to the doctor was mentioned, it was as a threat rather than a promise!
Hard to say how I would have reacted if she had offered me some clothes of my own, but I think I would have said "Yes".

[Stephanie Julianna]

Yes. However, it did not work out like that. My Mom caught me sleeping in a full slip. Went crazy. Calamed her down and said let's talk later. We did and she agreed to see me dressed. In those days, I was 17, I dressed in my room but did not do hair or make-up. I put on a very pretty green chiffon party dress I had and she said I looked very pretty. But, she added "It's just a phase. You'll get over it." I could tell that that was as much as she wanted to see or talk about it and that truly was the last we ever spoke of it.

[Giselle(Oshawa)]

I know my mom suspected that I had been in her nylons(runs) but never directly confronted me.
one year she got a dress from a friend who had an older daughter, and wanted me to wear it
on Halloween but I wouldn't do it as I was worried she would she how much I liked it and my
secret would be out and in the mid 1960's my life would have been over.

[Madilyn A.]

I am sure my mother must of known about my dressing due to stretched out, and slightly torn lingerie, runs in stockings, as well as my hurried undressing often caused her lingerie drawer to be not in the same order as she had left it..... I so wish she had confronted me in my early years. I still consider asking her if she knew. Wondering if there are any thoughts from others on this ?

[CherylFlint]

YES! (and I always wanted to dress for Halloween but was too timid).
But given the opportunity to have my own things, it would've been a dream come true.

[Annaliese]

I would know that my mother was open minded, even at that age so yes, I think that a open mother would have just taken me to the mall and started to shop for me. That would have been an exceptional mother.

[il.dso]

Great question.
I remember being so jealous when my mother would bring home a new dress for my sister.
I always wanted her to bring home girls clothes for me.
Regardless, I often wore my sister's and mother's clothes but wanted the clothes to be just for me!

[PattiL]

Actually my mother did ask me this question, but in a more stern/disapproving tone! In all reality even if she asked it in a more approving, supportive manner, I would have still denied everything and state I was simply "curious" or use some other wacky reason for wearing her clothes. Instead I would have asked for to take me to the mall to buy more video games.

Jocelyn, you read my mind - the exact same situation here.

[5150 Girl]

Well, it was a different time back when I was that age. I probably would have denied everything. However, If I were a 15 yr old in today's climate, She wouldn't have had to catch and ask me to go, I would be asking her to take me!

[Sarah Welch]

In the early 70’s I had been dressing for several years. I even had a female friend down the street who would help me by giving me her cast off clothes and showed me the world of makeup. One summer day my mom confronted me with a concerned tone, she held out a couple of tampons and the instruction sheet from the box of how to use them that was in a purse my friend gave me. Mom asked if I really wanted to be a girl so badly that I need to use tampons….well I didn’t know how to answer, I just started crying.

The next day, mom came into my room and gave me a shopping bag. In the bag was a pack of sanitary napkins, (the kind that required the belt to be used), a pair of pantyhose in my size, and a hi-leg panty girdle with matching bra in my size. She then told me if I needed any help with them I should not hesitate to ask her. Then she just said, I love you no matter what, turned and walked out of the room. This was the start of the best summer of my life.

[vallerie lacy]

I can't imagine my mother doing that, nor do I think I would go shopping with her. But I had an aunt who was my mother's younger sister, whose lingerie drawer I regularly raided. I used to do work for her around her apartment. I always wondered if she knew that I swiped her panties, I couldn't help myself. If she had confronted me about my love of her lingerie and offered to take me shopping, I believe I would have taken her up on her offer. She was a the type that I have always believed would have understood me.

[Sarah Welch]

When I finally got the courage to ask for help with my hair, she told me she would help. Two days later we both had appointments at the beauty salon. I got really nervous, but she just said not to worry and go get dressed and she would help with my makeup too. I wound up having one of the best days of my life with her, she took me shoe shopping later that day and got me my first pair of heels....I was in heaven. When I told her that I had never felt anything more feminine in my life, she just kissed my cheek and again told me she loved me and to never be afraid to share my feelings with her.

[Ally 2112]

Although i never got caught i came very close more than once .I know i would have been horrified at getting caught and not really sure if my mom would of asked that question .But if she did back then i would of unforunatly said no way.

[Amanda L.]

Hi Joan
What a great little fantasy to entertain. Had I ever been caught in this situation I would have to agree with many of the other girls here and say "no" but I guess let's look at the age spectrum. At 5 I probably would have gone as, well mum knows best and I may not have been brain washed to think that what I was doing was wrong, plus social interactions with other kids may not have shaped and negative perspective on the idea.
At 15, well the embarrassment would have been too great and heaven forbid if anyone found out!
As I write this I can recall a few minor incidents within that age bracket and now ponder how different life would now be if I were to have been encouraged to express my femininity.
Damn social norms!!!
Luv
Amanda

[MissTee]

My mom is proud of that fact that she raised 6 boys who are "all man." If she would have caught me dressing it would not have been supportive, but if she did offer to take me out I would have refused. Sorry, but I can't see her ever being proud of or encouraging dressing.

[Jacqueline1965]

OMG yes. I was caught several times. I have been wearing women's things since I was 3-4 years old. When I was about 13 my stepmother was about 32 and had an incredible collection of panties. When she was out my naughty self would go into her drawer and pick out some panties to wear around the house. Sometimes I would keep a pair or two and hide them between the mattress and box spring. Early one morning I was admiring myself in the mirror when she came up the stairs. I closed my robe real fast but she caught me red handed! She talked to my Dad about it and they talked to me about it...I had to give the items back and promise to never do it again...HA! I was afraid they were gonna ship me off somewhere to get "fixed". They chalked it up to puberty and a young man's curiosity. They just didn't ask me the right questions. Too bad she never offered to buy some for me. I would have gladly accepted even at 13. I was also caught by my mother at a much younger age but I don't remember what happened exactly. I was always envious going shopping with Mom and going to look at the lingerie. I always wanted to know (inside) why I couldn't buy some of the nice silky panties...life seemed so unfair. I never asked her to buy me any though. Maybe should would have if I had asked her.

[MelodyS.]

I would have in an instant.

This question reminds me of a Christmas years ago when I was young. My sister received a skirt and mom looked at it and was like, "This skirt would fir you better than it would her." (My sister was a bit larger than I)

First time home alone, I realized my mother was right, it sure did fit me better. :D

[RADER]

When I was 4 or 5, I would go into my mothers closet ant try on her girdles.
At the time, it was a big laugh.
At the age of about 10, she caught me hiding a few of her girdles under my mattress
of my bed. I got a "BIG" talking to. Well I discovered that I could build a secret hiding
place for "MY" things in the bottom of a built in dresser drawer in my closet.
So I built the secret compartment using it to hide 10 or 12 woman's fashions.
I had a few woman's bathing suits, those where my favorites.
We moved out of the house many years later; I bet there is still some things left behind
hidden there.
Rader

[Allisa]

I never really had the urge to dress up when I was younger and with 3 older sisters there were plenty of temptations, even when my sisters tried to dress me for Halloween my mother put her foot down and" no son of hers was going to dress up like a girl". Then around 13 I noticed girls for other reasons than their clothes which I tried to get them out of and not for me to wear. So I guess the answer would be no, phew took the long road on answering that question huh? But maybe in another lifetime Yes.

[tia61]

I can only wish I was caught by my mother. She was my ideal woman. Dressed so feminine and I always watched her. I would take her panties when I was 15 and never take them back. I ruined a pair of her shoes and a long night gown but she never said anything. I wanted so bad for her to know! Now she's gone and I regret never telling her. She would have loved a daughter.

[ericalynn]

I thought I was never caught, but then I remembered trying on a pair of my mother's heels, bright yellow. I was about 13 and my feet had already outgrown my mothers by 2 or 3 sizes, I forced my feet into the shoes with a shoehorn, tried walking and stretched (maybe ripped) the shoes on one side. I tried to glue them with some epoxy and painted with some model car paint. No way she could have missed it, but I never heard a word about it. If my mother had offered to take me shopping I would probably have been wary, but I would probably have gone.

[lingerieLiz]

My mother put me in panties at 5. I was out of underwear and she had me wear a pair my sister's panties. From then on I always wanted to wear girl's clothes. I think if she had asked me I would have said yes. But in the 50s there were no malls so it would have been dress shops.

[sometimes_miss]

What I do remember, is watching my mom get my older sister all pretty to go to school. I was 3 or 4, and such attention was never paid to me. So while that was going on, I went up stairs to the attic and took some of my sister's old clothes, put them on, went downstairs and presented myself, saying that I was ready to go to school too. Mom just got me changed back into my boy clothes, and we walked my sister to school. Then home again for me. At which, mom asked me if I really wanted to wear those clothes, but in such a way to imply that I should not, so of course I responded no, I just wanted to go to school like my sister did. That was the last time I openly wore girl clothes in front of anyone in my family.
At the time it happened, I didn't understand. I clearly remembered my mom dressing me up in girl clothes when I was much younger, so I thought it was OK. I had even rummaged through all the old clothes, and found the toddler dresses that my mom had dressed me up in. So discovering that now I wasn't supposed to wear girl clothes, was confusing. I wondered if maybe it was only OK for babies to dress up like that? What I did know was that I didn't ever see any other boys dressed as girls. I guess that was the first time I was learning to keep certain feelings to myself.

Edit. The concept that very young children ARE allowed to wear clothes of the opposite sex was reinforced to me a short time later, when a relative male child was baptised, and was dressed in a pretty gown. At later ages, it further confused me as I realized that my mom had kept dressing me as a girl at older ages than I knew other mom's did for boys.

[Beverley Sims]

At the time probably not, considering my age and experience then, but with what I feel now...
I would accept in a heartbeat also.

[jjjjohanne]

I was never caught, but I have a somewhat related story. When I was in my early 20s, I was asked to help out with an event. I would need to dress like a woman. Even though I was on a purge cycle, I immediately accepted on the opportunity. I asked a friendly female co-worker who was tall, and size 18/20 if I could borrow a dress for the event. She gladly helped. Then I went to a department store and for the first time, I bought pantyhose admitting they were for myself. I was brave enough to claim them because I had an excuse. I went to my girlfriend's house and used the bathroom. I came out of the bathroom wearing the pantyhose and dress. She didn't turn my way. I was standing there in obviously female clothes, in front of someone who knows me, for the first time, and she did not notice. When she finally turned toward me, and saw I was there in a dress, she laughed and discussed it briefly, and then I went and took it off. I commented on how I liked how the hose felt. I kind of hoped that she was say, "If you like them, wear them," but she did not. On some subsequent days, I suggested me putting on the pantyhose, and she disapproved. Later, my girlfriend and I bought some androgynous men's shoes to wear with the dress and to work in the following year. We went to a wig shop and bought a $25 cast-off wig. It was curly and bushed out a bit much, but it looked good enough. I sat in the wig hairdresser's chair. While she styled my hair, she told me some stories about some of her other male shoppers who shop for their female persona. She was respectful of them.

As the date of the event approached, my mother helped me with my costume. I put on what I had and she laughed until tears flowed. Then she started making me a bra with padding. She had to put an extension on the clasp because my chest was so much wider than hers. She produced a slip that was not silky. :( Somehow along the way, I was allowed to try on a different color of pantyhose. She presented her pantyhose drawer to me and I was free to try on whatever I wanted. Now, I had done this many times, but never with her knowing... I tried on several colors and showed her each. I sat there in pantyhose in front of my mother for an hour or two. At one point, while wearing some nude hose and shorts, I went into the living room and watched TV with my dad. This was amazing! At one point, I hinted to my mother about me wearing panties instead of my briefs (purge cycle had removed any female clothes from my stash). She disapproved.

The date of the event came. I shaved my legs for the first time in my life. My mom and girlfriend were surprised. I got dressed. My girlfriend did my makeup. We went to the event. Afterward, I dressed in men's clothes, but kept the pantyhose on. I realized that I had forgotten my socks. I was brave and kept on my navy blue hose and had no socks. We went as a group to a fast food restaurant. I worried that the general public would notice, but of course no one did. Later, some of my friends saw that I still had on the hose, but the didn't say anything. When we got back to the house, the friends I was staying with for the night mentioned the hose were still on. I explained I forgot socks in my bag (honestly, I did!). I took off my shoes and said something positive about them. They (my friends and my girlfriend) openly suggested it was time to take them off. So I did. Much later when I confessed my dressing to my girlfriend, she never suggested that she thought anything of the incident. She already knew that I liked the feel of the fabric from when she had worn them around me.

A few weeks after the event, I was washing dishes with my mother and I confessed that I had worn the hose in the previous week. I assume she had seen them in my sock drawer. She reacted in an awkward, disapproving way. I told her because I wanted to see if she would react like it was nothing. It might have been an opportunity to own some hose openly. Since she was disapproving, I dropped it. The week after that, I gave her the hose since "I had no need for them." And then, I was back to being purged.

[NicoleScott]

Yes, it is an interesting question. It's easy for this old brain to say "Yes" but my young embarrassed self probably would have said "no". Around age 10 or so I was caught playing with lipstick and punished by my dad with my mom silently compliant. Without his strong religious-based conservative lead, I think she would have been more understanding. Until, that is, she learned that I crossdressed for sexual excitement. I don't think she could have supported that. Not all of us are girly-guys inside.

[Cheryl James]

My mother never confronted me about knowing that I regularly dressed in her clothes. She did know, though, but chose to look the other way rather than confront me and embarrass both of us. Once,when I was about 12-13, however, I was shopping with her in a department store. We passed a bin full of bras for young girls. She, pointedly, asked me if I wanted her to buy me a couple. I was too embarrassed to say yes, but I kicked myself repeatedly for not doing so. If I had said yes, she would have, either, followed through on her offer, or not. It would, however, have led to being able to communicate with her about my true desires. What that would have led to, I have no idea. On the one hand, I believe that she would have rather had a daughter. On the otherhand, she was enormously proud of me as her son. Also, this occurred in the early 60's when men were men and women were women. My refusal of her offer led me down the well-worn path. Who really knows what would have transpired had I said yes. I do know that I am still dressing.

[Amy Lynn3]

My Mom, brother and sister caught me a number of time. I was really young and did not know enough to hide very well. At that young age and into adulthood I though I were some type freak, because I like to wear female clothing. Knowing that I would have never gone with anyone to be dressed or buy cloths.

[Jorja]

I only wish my mother could have caught me and offered to help. She died of cancer when I was six. My father caught me a few times and that meant a fist to the face and being knocked clear across the room then left in a lump on the floor until I could get back to my feet.

[Lorileah]

Just a thought...why are there always extra panties (sister's or wife's) but men's underwear seems to always be in short supply :confused:

[Ceera]

Not back then, no. Because even if my mom and my sister both fully accepted the idea of me cross dressing, and even if I never hoped to wear the girly stuff outside our home, I am certain my father and grandparents would have died of shame, and would have disowned me. And for that matter, most of my friends back then would probably not have accepted seeing me dressing up as a girl. I can only think of one person I knew when I was that age that I might have felt would accept me cross dressing, and that was the older boy that gave me my first intimate sexual experience. But I was too confused and ashamed to follow up with him after our one and only intimate encounter, and he died in a traffic accident less than a year later, so I wouldn't have even had him for support. I didn't tell anyone about that one early gay experience or about my bisexual leanings or trying on mom's clothes until I married a woman when I was 23 or so, and admitted it to her before we tied the knot. And my wife only knew I wore girly panties, when I started trying that after my father died a few years ago. She never knew I wanted to fully cross dress.

On the other hand, after my wife died and when I recently came out of the closet as an adult to my 18 year old daughter, my daughter volunteered to take me to the mall and shop for girly stuff with me, and we DO go mall shopping together once a week now. Haven't had the courage to go to the mall with her yet en-femme, but we shop for clothes and jewelry together, and I even slip into the dressing rooms and try things on there (though usually I take the girl clothes to a men's dressing room to try them, since I look fully male). She wants me to go to the mall with her as Ceera, and some day soon, I will...

[mariehart]

I was never caught which is a miracle in a small three bedroom house with six children. My Mother did once insist I wore a pair of my sister's panties but that was for the pragmatic reason that mine were all dirty. I was reluctant but she pointed out that no one would notice and they were rather plain.

Speculating though, if she did catch me it would have been around the age of twelve onwards because that's when it started. I wonder what her reaction would be. I never wore her clothes ever by the way. I suspect she would have told me to take them off and never do it again and left it at that. She is a kind but practical woman and with five other kids to worry about and hardly any money in the house, bringing me shopping was not a likely event. I often did go shopping with her though which I always loved. She has great taste but never had the money to express it. She would try on things and ask my opinion and we would dig into various piles of clothes in the cheaper shops in the city. That would happen even until recent years. She didn't like so much shopping with my sisters as they are often impatient and bossy. I am more chilled.

As it is many of my sister's clothes came from her best friend in Chicago. The arrival of the parcel from America every few months loaded with exotic American clothes was a great event. All girls stuff and too small for me anyway. A lot of Sears stuff which gave me the impression that Sears was a fabulous place! My first visit to a Sears store when I got to America was a nostalgia trip.

But I digress. There is a real possibility she did know but said nothing. I did notice a few hints over the years but nothing obvious. That would be typical of her.

Sadly she is ill now and may not be around much longer.

[Sharon B.]

My mother did catch me a few times trying on my sister's panty girdle, she always offer to buy me one but never did. I often wonder what would have happened if she did. But here I am some fifty years later and still enjoy wearing my own feminine attire. Now if I could just push that door open once again like I was doing about ten years ago. I used to go out during the day and evenings and didn't care who saw me. Took a rest from it now find it hard to push that door back open.

[Jorja]

Jorja oils the door hinges for Sharon. ;)

[Evelyn S]

Yes, I would have gone with my mother to buy girl clothes. We shopped together frequently for my boy clothes and she often brought me along for company while she bought clothes for herself. On top of it, she was seamstress, so I was used to being with her in dress shops and the women's clothing sections of department stores. She never knew (or at least let on that she knew) about my crossdressing while growing up, but if she did and was supportive of it, I would have been very comforable going to stores to buy girl clothes for me.

[Diane1950]

I never got caught either, altho there were some close calls. My mother would have raised aall kinds of hell, though, if she ever found out. My a** would have been grass, as we used to say.

[BLUE ORCHID]

Hi Joan, I've never been caught, :daydreaming: but it's a great fantasy.