Did you try on your grandmothers clothes?

You must be logged in to participate.
  • Yes
  • No
  • Creator
  • #587919
    Registered On: October 3, 2019
    Topics: 11
    Replies: 145
    Has thanked: 500 times
    Been thanked: 956 times

    I remember when growing up I stayed at my grandmothers house on weekends.   She always slept downstairs and I upstairs.  The next bedroom over my grandmother had her things in it.  People call her stuff vintage now days.  Lol.  Dresses, shoes, lingerie, wigs and more.  Many fond memories sneaking into her room and trying on everything from girdles, bras and wigs.  It was a great time because I was finding myself with such a wardrobe at my fingers.   I some how think she knew.  Lol

    anyone else enjoy wearing their grandmothers things?

    • This topic was modified 5 months ago by Gabriela Romani. Reason: Moved to polls forum
Viewing 18 reply threads
  • Author
    • #606370
      Kristen Smithly
      Registered On: September 25, 2020
      Topics: 5
      Replies: 93
      Has thanked: 389 times
      Been thanked: 487 times

      Only once, and that wasn’t a planned thing. I was maybe 7 or 8 yrs old at the time. My parents were on their way to my aunt’s in another state where my brother’s had been staying for a while. I din’t want to go (long, boring car ride and at the time, both parents smoked heavily with the windows up) so mom packed me a bag and they dropped me off for a visit at my grandmother’s, which I look forward to because she was a nice fun person. Mom forgot to pack me some pajamas, so grandma offered me one of nighties to wear, I wasn’t sure what a nightie was, but I said yes because I needed something to wear. It wasn’t anything sexy (she was a grandma, after all) but it was light, airy material with lace trim. The moment I put it on I felt wonderful. It was a little long, but she wasn’t a tall woman so it reached to about my ankles. I loved the feel of it, the lace, the somewhat sheerness of it. Wonderful. It was the only time I ever wore any of my grandmothers clothing.


      1 user thanked author for this post.
    • #591252
      Ozark Mountain
      Registered On: July 23, 2021
      Topics: 0
      Replies: 2
      Has thanked: 6 times
      Been thanked: 2 times

      My grandparents had a river cabin outside of St. Louis. My two brothers and I as we were growing up would spend weekends out there with them. My granpa snored and slept in a bed across the cabin, my two brothers slept in a convert a bed a couch that the back folded down for a ‘bed’… very uncomfortable. I slept in the double bed with grandma.
      usually we slept in our briefs. Grandma wore night gowns and robes, even at the cabin.
      Pleasant memory.

    • #590547
      Registered On: January 9, 2021
      Topics: 19
      Replies: 236
      Has thanked: 671 times
      Been thanked: 1448 times

      Absolutely have done this rosiebeth and in very much the same way. I remember being drawn to that closet and next thing I knew I was powerless against the urge to try her blouses and skirts on. She had such pretty things. Maybe that’s why to this day I enjoy that retro look. I was like a kid in a candy store! Such fond memories and such a irresistible opportunity as a 10 or 12 year old for me personally at least.

      2 users thanked author for this post.
    • #588886
      Rachael Wanttobe
      Registered On: July 21, 2021
      Topics: 1
      Replies: 55
      Has thanked: 188 times
      Been thanked: 183 times

      Not grandmother but mother.

      2 users thanked author for this post.
    • #588756
      Amy Myers
      Registered On: February 11, 2019
      Topics: 23
      Replies: 1644
      Has thanked: 4875 times
      Been thanked: 5351 times

      I started out by wearing my Mother’s clothes, I never had a chance to wear a grandmother’s clothes, though I am not at all sure I would have as they were so much more conservative than my Mom’s.


      2 users thanked author for this post.
    • #588385
      Samantha Peders
      Registered On: May 12, 2020
      Topics: 5
      Replies: 50
      Has thanked: 97 times
      Been thanked: 180 times

      When I was three years old I liked to wear my grandma’s hats and shoes. I then started wearing her camisoles as slips. They thought it was cute until then. She started keeping them from me after that.

      3 users thanked author for this post.
    • #588377
      Topics: 0
      Replies: 0
      Has thanked: 0 times
      Been thanked: 0 times

      No both my grandmothers were 3500 miles away and my mother dressed like Mrs Doubtfire. I loved my mom dearly but her fashion sense was not the greatest. I used to raid my sisters stuff. She was very pretty  and always dressed well.

      3 users thanked author for this post.
    • #588266
      Dawn Judson
      Registered On: November 26, 2017
      Topics: 11
      Replies: 137
      Has thanked: 355 times
      Been thanked: 668 times

      I can only think of one thing, of my grandmother’s, that I ever tried on. I was 11 (when my femme feeling had started to surface) & she had passed a few years earlier. One day, I was looking for something in the garage & came across a box that had some of her things in it– including a pair of high heels. I tried them on & wouldn’t you know it? That’s when my mom opened the garage door & caught me.

      I don’t remember what was said, but I immediately took them off & nothing was ever said about that incident again.

      2 users thanked author for this post.
    • #588176
      Roberta Broussard
      Registered On: July 20, 2020
      Topics: 5
      Replies: 239
      Has thanked: 3556 times
      Been thanked: 1128 times

      Nothing she had caught me curious but i never would have had an opportunity anyhow. Now my Mother was a different story. After trying on her swimsuit, I couldn’t get enough of it. I even skipped school sometimes just to go back home any try on her things.   I was so confused about it all, I was truly a lost soul for a while.

      2 users thanked author for this post.
    • #588172
      Lacy Satin
      Registered On: June 27, 2018
      Topics: 7
      Replies: 486
      Has thanked: 442 times
      Been thanked: 2232 times

      I wanted too so bad!

      My grandmother lived with us for a few years and always walked around wearing a full slip. nothing else. At the time a slip was one thing I had never worn. I had sneaked into her room and she had a drawer full of pretty slips but I only could look and dream about taking one.

      My grandmother was extremely neat and everything was folded perfectly and my fear was I would never be able to refold it as well as she did so I never touched them.

      She moved out and got her own apartment. When she passed away I had my chance to go to her apartment and take as many as I wanted, if not all of them.

      Again, I passed on the opportunity because something inside me felt it was wrong and it would have felt a little creepy going in there and taking her lingerie. Something inside me felt she would be looking down on me and I would be punished for my actions.

      I believe I’ve told this story before but it’s worth sharing again.

      After my grandmother passed away, and I’m not sure how long after she was gone, this strange event happened to me.

      I was a member of Stage crew in high school and had access to the basement of the stage. One day I skipped out of class and went to the basement of the stage to hide out. As I was walking through the very dimly lit basement I was shocked to see this very pretty full slip just hanging there on a pipe in the middle of the basement.

      Why was it there? Who would have hung it there? I walked past it several times admiring all the pretty lace and my heart was pounding. I never touched any of my grandmothers pretty slips that were just like this one, and now there one was, hanging there for the taking.

      Sadly, I walked away in fear it was a setup. If I were to even tough it, I felt my friends would come running out of the dark corners of the basement and start laughing at me. I don’t think any of my friends knew about my crossdressing but I was in fear of taking that chance.

      I made several more trips through the basement over the next few days just walking past it and wanting to take it so bad but still couldn’t get over the fear of it being a setup.

      I believe on around the 4th day I walked through again and sadly I saw it hanging there with graffiti written all over it. I was so upset to see what happened to this pretty slip I just couldn’t let it hang there anymore and I took it and stuffed it in my pants.

      I got it home and tried my best to get the graffiti off with no sucess. It was my first slip so I still wore it and enjoyed it even covered with graffiti.

      As I look back on this encounter with the fantom slip I can’t help to think, could it have been a gift from my grandmother? Strange as it sounds, but I can’t think of any logical explanation as to why it was there and where it could have come from.

      I never touched my grandmothers slips and she just may have somehow returned to leave me a gift.

      Spooky story but very real! Any thoughts on this would be very interesting to here.



      2 users thanked author for this post.
    • #588166
      Carolyn Kay
      Baroness - Annual
      Registered On: August 25, 2016
      Topics: 21
      Replies: 381
      Has thanked: 1620 times
      Been thanked: 1833 times

      I had to vote no but not because I didn’t want to try them on, I just never had the opportunity.

      3 users thanked author for this post.
    • #588127
      Registered On: October 7, 2021
      Topics: 33
      Replies: 397
      Has thanked: 2694 times
      Been thanked: 1793 times

      Never had the chance to wear their clothes. My father’s mother died before I was born and my mum’s mother had my aunt and two cousins living with her.


      2 users thanked author for this post.
    • #587990
      Carolyne Sherman
      Registered On: February 20, 2018
      Topics: 10
      Replies: 544
      Has thanked: 529 times
      Been thanked: 2174 times

      I did try some of my grandmothers things as she was always a classy lady. I have to think she probably knew I was her secret granddaughter as she did buy me things throughout my youth that even though they were boys clothes they definitely had a feminine flair. I wish I would have told her. She was very much the matriarch of the family and if she would have supported  me no one would have dared stand against her.

      4 users thanked author for this post.
    • #587969
      Topics: 0
      Replies: 0
      Has thanked: 0 times
      Been thanked: 0 times

      Did  try on few things that took a interest to  her fur jackets and heels. and panty hose.


      5 users thanked author for this post.
      • #587973
        Michelle McQueen
        Registered On: June 14, 2021
        Topics: 24
        Replies: 1234
        Has thanked: 7572 times
        Been thanked: 6118 times

        Hi Donna. Sounds like you had a sophisticated, sexy, grandmother

        2 users thanked author for this post.
        • #587977
          Topics: 0
          Replies: 0
          Has thanked: 0 times
          Been thanked: 0 times

          yes she was back in the days.

    • #587967
      Michelle McQueen
      Registered On: June 14, 2021
      Topics: 24
      Replies: 1234
      Has thanked: 7572 times
      Been thanked: 6118 times

      No, because what my grandmother wore had no appeal for me at all. She collected dolls and I longed to wear pretty dresses like her dolls wore.

      4 users thanked author for this post.
    • #587965
      Emily Alt
      Duchess - Annual
      Registered On: August 24, 2019
      Topics: 14
      Replies: 758
      Has thanked: 626 times
      Been thanked: 3620 times

      No.  My maternal grandmother died before I was born.  My paternal grandmother was very traditional and didn’t own any flattering clothes.  My mother worked in the banking industry and had plenty of eye catching garments that I “borrowed “.

      3 users thanked author for this post.
    • #587927
      Registered On: September 13, 2018
      Topics: 36
      Replies: 1759
      Has thanked: 2298 times
      Been thanked: 5704 times

      I didn’t need to. She always bought me the prettiest clothes!
      She knew before I did!

      4 users thanked author for this post.
    • #587926
      Celeste Starre
      Registered On: June 26, 2018
      Topics: 49
      Replies: 1376
      Has thanked: 382 times
      Been thanked: 5050 times

      No,my grandmother had really ugly clothes.

      4 users thanked author for this post.
    • #587925
      Tara Ryan
      Registered On: April 20, 2021
      Topics: 4
      Replies: 451
      Has thanked: 1417 times
      Been thanked: 1753 times

      Hi Rosiebeth,

      While I would have loved the opportunity to dress in my grandmother’s vintage clothes, unfortunately my grandmother was quiet ancient even when I was child and the bloomers and support stockings didn’t really have much of an appeal.


      Tara x.

      4 users thanked author for this post.
Viewing 18 reply threads
  • You must be logged in to reply to this topic.
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials


Forgot your details?

Create Account

If you don't see the captcha above please disable ad and tracking blockers and reload the page.