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Thread: Starting the dressing journey later in life.

  1. #26
    Just Being Me Paula G's Avatar
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    I was about 10 or 11 when I first tried nylons and heels, and my first skirt shortly after I got married at 25. I really did not start fully dressing until I was almost 40 though, and it was one of the best things I ever did!

  2. #27
    Silver Member Leslie Mary S's Avatar
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    Like I said before, I stated "sampling" about age 9 (@1952). around 1962 I stepped up my "Sampling". It was around 2006 before I became much more active. That was after the death of my first wife and after divoricing my second wife. I was living alone then. I did do some M to F dating for about 4 years from 2006 to 2012. since then It has been just me.
    Last edited by Leslie Mary S; 05-31-2020 at 06:19 PM.
    Leslie Mary Shy
    A Southern Belle Hippo in a Tutu. If you see a man in female clothes, he might be happy, but it does not mean he is gay.

  3. #28
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    I started underdressing in my 20's.

    But, I finally started dressing and going out as Claire once I turned 50. Felt like I needed to be me.

    Now, I wear panties every day. Nighties occasionally. Wife is reluctantly OK with this level.

    And (pre covid) go out 2x a month fully dressed and go shopping at the local crossdressing friendly stores (Soma, WHBM, Chico's, MAC counter for makeup application and tips, Nordstrom Rack, Old Navy). Wig, makeup, purse, press on nail, etc. Wife is unaware is this side of me.

    Amazed at how helpful all the staffs are. I don't feel passable, but even the other shoppers don't bat an eye, and occasionally, comment on how nice my outfit is. )))

  4. #29
    New Member ShoeziQ's Avatar
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    I would say I started sneaking into nylons and panties in my early teens. I was 27 when I bought my own lingerie and shoes. Now in my 40's I just buy what I like. Thankfully I know my sizes!

  5. #30
    Junior Member
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    If I am honest with myself, a little dabbling in high school, an occasional Halloween in college, then a gap until I finally figured out I might like dressing in my mid- to late-30's. Kind of dove in then while the (then) g/f wasn't all that into it. Fortunately after transitioning her out of my life, I met my now wife who is completely accepting and a willing participant. So, (as measured by another post on here), now currently a part-time (when my time allows and I feel like it) level 4 dresser and enjoy it when I can. So, I would say came to dressing mid-life and glad I didn't wait to figure it out any longer!

  6. #31
    Senior Member
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    I first discovered my mom's closest and lingerie drawer when I was 16 or 17, but it was the 1970's and the culture of my home was one of violent homophobia. Femininity in a male was the hugest taboo i could think of. So when I put on my moms pantyhose and found I ENJOYED it, I was horrified, disgusted, and fearful of what could happen if I were found out. It took a long, long time to come to terms with my feminine side and then come out to my wife, who then became horrified, disgusted and fearful. We are in our sixties now and she is just getting comfortable with me now. So yeah, a lot of things have to loosen up before one can speak frankly about their dressing.

    I am totally envious of the children growing up nowadays. Boys can, in limited situations like womanless pageants, express themselves more freely and their parents are increasingly supportive. There's a long way to go, but there's hope that people like us won't have to fight stigmatization over a simple bit of cloth. Who knows? Maybe sites like this won't be necessary as it becomes Not A Big Deal for a man to wear a skirt and heels if he so chooses. Its exciting to imagine a world where a boy has as much freedom as his sister.

  7. #32
    New Member adelinapa's Avatar
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    i remember my first affinity for clothes was spending more time in the Sears catalog looking at the women's section more than the toys section when i was very young but didn't sneak into my mom's things until high school. it wasn't until i was in my 30s was it actually a thing and then it wasn't until recently that i have stopped the purge cycle.

    I loved reading what everyone shared.

  8. #33
    Aspiring Member
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    Yeah, the Sears and Penney's catalogs were interesting to me as well. Had to be careful to not get caught in the wrong section. Then it was trying on my mom's clothes at about an early teen age..That continued through HS and never got caught, or at least no one ever said anything. Then married and kids so that ended it for many years. About my middle 40's and on when I was alone in the house more with no kids around I began to experiment more. My job also led to me traveling for meetings and such so that allowed some freedom for me to purchase some women's clothes and other accessories. Now at the age of 70 and both my wife and I retired it's back to not so much. I know I will be told I should have told my wife years ago but knowing her as I do there is no way she would be OK with me dressing.

  9. #34
    Aspiring Member Angela1954's Avatar
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    I began by wearing my mothers tights when I was about 11 or 12. I wore them only in the house. I'm a runner, so when running tights came on the scene I was thrilled. I always had the desire to dress fully. When I started living alone I began experimenting with makeup. The first time I went out dressed and in makeup was a quick trip for gas. Luckily it was at night and I looked ghastly lol. I finally got a makeover and was absolutely stunned at my appearance. I was around 52 or 53 at the time and have dressed since then. If I had been born at a different time I would have started dressing much earlier and may have transitioned.

  10. #35
    Daviana Kristine Jessie Mae's Avatar
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    Nothing until age 64. When I started dressing, it was full femme; wig, makeup, clothes. All or nothing.
    With my wife's full knowledge and support (thank god).
    Still not sure how it happened. But looking back there were "signs".
    Last edited by Jessie Mae; 06-03-2020 at 06:36 AM.
    Please call me Daviana

  11. #36
    New Member crobeson96's Avatar
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    The mention of gender issues caught my attention. Just the type of discussion that makes me happy this website exists! For most of my life homosexuality was society's worst taboo and crossdressing just a step on the way to perdition. Thankfully today you can easily find more enlightened consideration of a range of behaviors and their likely bases.

    First I believe science has established that masculinity-femininity is an analog rather than binary variable. Second, much of our behavior is learned rather than innate.

    Those two factors alone make living with 'unusual' behaviors possible.

    I'd assume a desire to wear women's clothing was simply that. The professional's rule is that unless a behavior is affecting your life in a way you find negative, you can work your way past any unpleasant feelings and simply enjoy it. I'm not one (a professional) so anyone wanting to correct or enlighten, I welcome your thoughts. As for me I'm just thinking out loud -

    As for the topic of the post, CD began at an early age much as everyone else describes.
    Last edited by crobeson96; 06-03-2020 at 08:20 AM.

  12. #37
    Super Moderator Raychel's Avatar
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    For me it was basically under garments, until I was about 45 years old

    But with the change of events at that age, (I told my then wife)

    from that point on I progressed to full dressing. And enjoying being dressed as I feel most comfortable.
    Pretty much full dress from the neck down.
    It is confusing to many people I am sure. But in my mind it works.
    Crazy place in my mind,

    No gender issues, I am still a man, absolutely no desire for anything else.

    So yes, definitely started really accepting me later in life.
    my sister's reply when I told her how I prefer to dress

    "Everyone has there thing, all that matters is that you are happy, love what you do and who you do it with"

  13. #38
    Senior Member BrendaPDX's Avatar
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    Freshmen year in high school was the age I bought my first dress.

  14. #39
    New Member bobbi1957's Avatar
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    i had thoughts about dressing during my life but didnt start till i was 56. i now love getting out fem

  15. #40
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    When I was young I would put on my moms knee highs and some old heels while watching ?Bosom Buddies? and she knew. Early teens my chores became laundry. I discovered how amazing nice pantyhose felt. My mom worked at a higher end department store. Teen years it was morefor self gratification, hose heels bra, a teddy she did not wear.

    When my wife and I started dating I list the ?need? to do it. Over the next 20 years not much of anything. I found some cheap drug store pantyhose in a suitcase I loaned my mom. Every now and then I would put them on.

    Since 2011 i lost my mom, my dad?s mother and most recently my dad 3.5 years ago, in other words my entire family in laws not included.) At 42, I ordered my first dress, bra, hose and heels from Amazon. That was three years ago this month.

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