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Thread: Vivid Memories Of Childhood Crossdressing with Sisters and Mother

  1. #1
    Aspiring Member Robbiegirl's Avatar
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    Vivid Memories Of Childhood Crossdressing with Sisters and Mother

    I still have vivid memories from my youth of episodes that I think had a huge impact on my dressing today! They actually had more to do with the Joyful reaction of the gals to me being in female attire that really sticks out to me. Anyone have stories from their youth of dressing up in girl clothes with females involved ?

    My first experience in Girl Clothes -
    Ok When I was about 7 and my older sister 8 were going to get a visit from the nanny who had help raise us from birth. Mary was now in her late 70s and we had not seen her in about 4 years. My aunt and girl cousin Annie was over since Annie had spent time with her also. My Mom turned to my sister and told her to go get dressed and that she had laid out a pretty dress like Annie was wearing. My Tom Boy sister Tammy turns to my mom and says why do I have to wear a dress and Sal doesn't. My mom says to her don't be silly he is a boy and you are a girl so get upstairs and put on your dress so I can fix your hair.
    Ten minutes later Tammy comes down wearing some of my nice clothes and a baseball cap. My Mom asks her what in the heck are you doing. And she responds I thought it might be fun and funny to trick Mary into thinking I am Robbie, Well my mother and aunt look at each other and burst out laughing and both agree its a great and clever idea. There is then a bit of silence and I start wondering in horror if they are thinking what I am thinking. Tammy then breaks the silence by saying so Sal you get to pretend to be me and wear " The Pretty Dress " Well they all howled in laughter but me. And my mom says oh what a great idea ! I of course said no way but my mother said oh yes.
    The Dress was Yellow ,short with puffyness at the hem and on the sleeves . After putting barrets and bows in my hair I saw myself in the mirror and almost died ! I looked Like a very girly little girl and felt so weak and exposed in the dress ! I have never seen my sisters happier, they were litterally jumping up and down with glee. My Mother and Aunt just kept giggling ans using terms like Adorable and Darling ! I had to pose for way too many pictures even a couple holding a doll ! And of course our old Nanny was late and of course she too enjoyed seeing me in the frilly dress !
    Again I remember just how much wearing the dress made me totally not feel like a strong boy at all but I have a greater memory of just how much fun and glee it gave all the females involved to see a boy easily turned into a Girl ! Of course for weeks my sisters and mother were always asking if I wanted to wear a dress since I looked so cute in them !

    Any thoughts or similiar experiences ? I have a couple more experiences but I will wait and see if there is interest

  2. #2
    Member Gi Gondin's Avatar
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    Hi Robbie. Thanks for sharing. Many of us search for answers and explanations from early age crossdressing experiences. And in my case I believe I found a turning point, or better stated a starting point.

    Since both of my parents worked, during summer vacations, they left each kid in a different relative home for weeks. And in more than one opportunity I stayed with two female cousins that were 5 and 7 years older than me. In those occasions they used me as their model doll and pretend I was a princess or a doll or just some younger baby girl. Those role playing games were very innocent and without any sexual or seductive behavior. Just a bunch of 10-15 year girls having fun during their summer vacation.

    But it took me decades to decifre the impact and the relevance of those experiences in my behavior and sexual drive. My current understanding is that I felt so special and cared and loved during those role playing games that “primed” in me a direct association between a female appearance and satisfaction. I can recall the anxiety and desire to be part of it even decades after - very strong.

    Of course I tried to emulate the same feelings as I grew older with my moms closet and make up, and in my adulthood with crossdressing.

    I am pretty sure that without those early child experiences, I would never crossdress. My girlfriend says that one day she will thank them (my cousins) for having me playing with them.
    Last edited by Gi Gondin; 08-07-2021 at 04:45 PM.

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    Hi Robbie Girl , Thanks for sharing such a wonderful memories with us,

    That never happened to me, >Orchid**o0**
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

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    Senior Member DianeT's Avatar
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    I was dressed in dance tights for a kindergarten school event at 5 (we were living in the US back then), and yes women dressed me like this (teachers and mothers). The tights probably were pink (I recently found the spectacle brochure in a pile of childhood souvenirs after losing a parent and we were playing three little pigs, and not little white rabbits as I fuzzily remembered), although I can't confirm the color in my souvenirs. What I vividly remember however is doing the show on all fours in front of a large audience with the very unsettling feeling of being dressed as a girl, and in intimate apparel with that.
    I never go out so maybe this was my only outing if that counts...

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    Aspiring Member Robbiegirl's Avatar
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    Thanks so much for sharing Gisele ! Also thanks for mentioning that your experience with your female cousins was not sexual, since my experiences with my sisters was also not. I do believe my being dressed as a little girl and being very convincing led me to be curios years later about how I would look in all my sisters outfits ! It was just pure fun and funny to see how I looked and could dance in their ballet tutus and dresses. I am sure they would have loved to have seen me in them since we were always doing crazy things. When I was about 11 another boy and I had to run around the block in my sisters tennis dresses, ruffle butt panties and head bands for losing at a game called spoons. All good fun !

  6. #6
    Connie Connie D50's Avatar
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    I had 3 sister (and 4 brothers)I was 8years old I had already been trying on older sisters and Moms panties . When Halloween came around my mom was our Cub Scouts pack leader. At the Cub scouts party she dressed me in my sisters leotards a long with her baton. I'll never forget that night.
    On one other occasion again in Cub Scouts we were doing a Beatie's skit for the total troop and she wanted screaming girl fans during the skit. You quested it I was one of those screaming fans In mini skirt. wig and of course white go go boots.

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    Senior Member GretchenM's Avatar
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    I suspect you are on to something regarding some kind of an origin point for your dressing as an adult. However, according to some theories being dressed like a girl may or may not trigger a desire to dress later in youth and adulthood. There are plenty of studies to show that this happening causes a person to identify, at least to some extent, as female-like where boys followed that route. But there are plenty of stories where being dressed as a girl in youth had no lasting effect, other than feeling repulsive.

    It is thought that events like this can easily activate a predisposition to associate femaleness with yourself and all that follows that. If a predisposition exists in these individuals then it is probably a matter of some kind of genetically linked behavior that is a predisposition. Predispositions remain inactive until triggered by something or a series of events that reach threshold that triggers activation. The thing is, predispositions do not come supplied with off switches. Once activated they persist. But the degree of activation, that is how strongly the feeling is, varies probably because of other factors that influence the predisposition's actions.

    Many of us here can tell similar stories and a memory that the events seemed to trigger something very deep in our identity that is often persistent. It didn't happen that way with me, but the finer points of predispositions can vary as to what turns it on. So, if that is the case then it is unlikely the predisposition will ever go away. So, so long as you have it, enjoy it; it is a part of who you are. Resisting its effects just produces dysphoria which can lead to serious depression. Not a good idea to go there.

    Humans have tons of predispositions. One of the favorite examples is handedness. Thirty five genes are involved in developing this predisposition. You are born with the predisposition turned off. Very early in your life you reach for things. The hand that logs the most successful contacts will activate the predisposition. If you have a predisposition for being right handed at some point your success in using your right hand triggers the predisposition and you are right handed for life. But what if you had that predisposition but were born with a deformed right hand? Your highest success would be with your left hand and that induces left handedness because the right hand predisposition is never activated. Your left handedness though is not a predisposition; it is that way because it is the only way available. Predispositions are attached to things that can go either way depending on what happens to you. Some are not activated for years and years and then, wham, the behavior becomes established. But they are all based in genetics.

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    Senior Member April Rose's Avatar
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    I never had such an event, though I had a lot of daydreams about that sort of thing. I had an older cousin who was always pushing me toward girls activities, though I always resisted it. I think that might have served as my trigger.

    What Gretchen says makes a lot of sense. I am pretty sure I am left handed because of poor vision in my right eye. My evidence for this is because as I have gotten older I have gradually become more and more ambidextrous.
    I am a vessel of the goddess. Let me express my calling to a feminine life through nurturing love and relatedness.

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    Aspiring Member Robbiegirl's Avatar
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    Quote Originally Posted by Connie D50 View Post
    I had 3 sister (and 4 brothers)I was 8years old I had already been trying on older sisters and Moms panties . When Halloween came around my mom was our Cub Scouts pack leader. At the Cub scouts party she dressed me in my sisters leotards a long with her baton. I'll never forget that night.
    On one other occasion again in Cub Scouts we were doing a Beatie's skit for the total troop and she wanted screaming girl fans during the skit. You quested it I was one of those screaming fans In mini skirt. wig and of course white go go boots.
    Well your mother clearly had a great sense of humor, and you were quite brave ! I do wonder what your brothers and sisters thought about your costumes and if they had similiar stories ?
    Also just wondering, did your sisters ever do girl scouts or Brownies and did you ever try on one of those cute outfits ?

  10. #10
    Connie Connie D50's Avatar
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    Robbie I don't remember any problem from my brothers or sisters on those two occasions. I also don't remember her dressing up any of the other boys. Yes sister were in Brownies and yes I had to try on those cute brownie uniforms :-).

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    Senior Member SaraLin's Avatar
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    I only had two "approved" CD events in childhood. I've talked about them before, so I'll be brief this time.

    1. Mom had me dress as a girl one Halloween. Neighbor lady loved it, saying I was "The cat's pajamas"
    2. Cub scout play. I was the "damsel in distress" that the brave knight rescued. I gave him my heart as a reward (carboard, covered in foil)

    That's it. No other incidents where it was OK.

  12. #12
    Aspiring Member Robbiegirl's Avatar
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    Wow I should have been a Cub Scout ! Who knew that the scouts did such fun plays where some boys had to dress as Girls !

    To my point, I am sure the Den Mothers loved dressing the boys as Girls !

  13. #13
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    Quote Originally Posted by Robbiegirl View Post
    I still have vivid memories from my youth of episodes that I think had a huge impact on my dressing today! They actually had more to do with the Joyful reaction of the gals to me being in female attire that really sticks out to me. Anyone have stories from their youth of dressing up in girl clothes with females involved ?
    I can totally relate to this and have vivid memories of those occasions. I was so scared of being caught and/or family knowing?and I?m guessing my father/brother/sister said something that made me uncomfortable about it. But my mother like to have fun?curl my hair, etc. But there were plenty of other experiences with girlfriends. But I was such a wimp, so I didn?t take advantage of it, out of fear of being caught.

    The irony? My own wife would get a kick out of other little boys (young and old) that she?d see dressed for Halloween or other things and even contribute. She knew I loved this stuff, but just didn?t surprise me.

    Thankfully she is totally down with my feelings and encourages me to dress. However, unless she?s the one doing the dressing, it just doesn?t have the same buzz for me?which is totally fine. Life should be fun, but I think we should all be able to separate life with fantasy, and keep them separate (my two cents). But again your post resonated with me so much and I could feel the excitement as I read it.

    However, I also think GretchenM has a point. That is some will be triggered by this?and probably in different ways, some will be embarrassed, humiliated, and maybe even angry about it. I obviously wasn?t one of these.

    Thankfully, I?m totally at peace with my background. I realize that it isn?t something I chose, but I also recognize the responsibility I have to keep things in check?and I?m grateful I know how to do this.

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