Page 1 of 3 123 LastLast
Results 1 to 25 of 56

Thread: What is Your Fondest Memory of Crossdressing?

  1. #1
    Member Katherine L.'s Avatar
    Join Date
    Jan 2012
    Location
    Mid-Atlantic
    Posts
    259

    What is Your Fondest Memory of Crossdressing?

    For me it was the first time my wife saw me wearing a bra. I was 27 years old at the time and we had only been married about 10 months. A few months before, my wife had discovered my only article of female clothing, a bra, that I had hidden among the male clothing in one of my drawers. Not surprisingly she reacted badly to the discovery, including tears, anger and all the normal questions. In the intervening months, she said little about the bra, but at least said I could keep it.

    On this particular evening, we were watching television and cuddling together on the couch. She was caressing my chest and playing with my nipples, something she knew I loved. I made the comment that if she kept doing that I was going to want to wear my bra. To my amazement she said go ahead.

    I went back to our bedroom and put on my bra, filled out the cups with some of her panties, and replaced my shirt. When I returned to the living room I was both terrified and excited, but mostly embarrassed. She quickly eased my fears and we began cuddling and caressing again. After a few minutes she took me to the bedroom where we completely undressed, except for my bra, and made love.

    We have now been married 35 years and since then she had seen me countless times in bras and other items of lingerie. Still, that first time remains my fondest memory ever of crossdressing.
    Last edited by Katherine L.; 08-09-2020 at 04:55 PM.
    WARNING: Any institutions or individuals using this site or any of its associated sites for studies, projects, or any other reasons, you do not have permission to use any of my profile or pictures in any form. If you do, it will be considered a violation of my privacy and will be subject to legal action.

  2. #2
    Silver Member
    Join Date
    Jan 2016
    Location
    Orange County, California
    Posts
    3,081
    My first time out with sister friends and having dinner. Thanks, Sherry and Cindi!

  3. #3
    Member Happilymarriedguy's Avatar
    Join Date
    Sep 2013
    Location
    Midwest USA
    Posts
    490
    I would have to say my fondest crossdressing moment would be when my wife saw me dressed in my lingerie for the first time. She was very accepting of who I am.

  4. #4
    New Member KimH's Avatar
    Join Date
    Aug 2020
    Location
    British Columbia
    Posts
    9
    Mine was very similar, my first positive "out" interaction.

    In my 20s I spent a beach week in and out of sundresses, skirts and my first ever bikinibat the cabin I was staying at. One afternoon I was on the deck reading in my bikini and had been pulling up a sarong when people came by. I wasn't paying as much attention as I thought I was and the guy staying in the neighboring cabin came up. I assume I looked like a deer in the headlights but he was very casual and exchanged a little small talk before heading in. It was only a few moments but the fact that the world didn't end and there and no angry mob appeared was a beautiful eye opener!

  5. #5
    New Member
    Join Date
    May 2020
    Location
    Texas
    Posts
    19
    So I have been closet dressing with lingerie since 10 or so. My first time to fully dress was just this weekend. I went to a well known transformation service and bought all I needed. The artist made me look super. I had always planned to go back to male before leaving. I was so embolden by her work that I left enfemme and went back to my hotel. I did run in quickly however. Still what a first experience.

  6. #6
    Senior Member BrendaPDX's Avatar
    Join Date
    May 2016
    Location
    Portland, Oregon
    Posts
    1,705
    The first time I met a fellow CD for coffee fully en femme, I was terrified! But the world didn't stop turning, and the coffee experience turned out to be "just no big deal to others" and a life changing moment for me.

  7. #7
    Senior Member NancySue's Avatar
    Join Date
    Jun 2016
    Location
    Southern Illinois
    Posts
    1,891
    Me too...the first time my wife saw me fully dressed. She smiled, complimented me and gave me a hug. I tentatively asked her if she?d like to see my lingerie. She paused and said ?if you want to?. I was a little hesitant, but I took my skirt and blouse off. There I was...full makeup, wig, bra, forms, panties, pantyhose, a half slip and heels..all black. She smiled and so did I. She asked me if I was comfortable. I just smiled. It was also the first time she teased me about finding underwires, pantyhose and heels comfortable. She hates all three...interesting..I can?t wait to put on...what she can?t wait to take off.

  8. #8
    New Member
    Join Date
    May 2020
    Location
    Texas
    Posts
    19
    What a wonderful moment between you two. LOVE LOVE LOVE!

  9. #9
    Member
    Join Date
    Aug 2018
    Posts
    306
    I'd have to say that it was the first time she reached up under my dress to explore without warning...

  10. #10
    Aspiring Member jacques's Avatar
    Join Date
    Sep 2008
    Location
    East Yorkshire UK
    Posts
    731
    hello Katherine,
    probably the fondest memory is when I came out to my wife and she said "Is that all. It's only clothes, I thought you were going to say something important!"
    I am still trying to process that!
    Stay healthy
    luv J

  11. #11
    Silver Member Micki_Finn's Avatar
    Join Date
    Aug 2016
    Location
    Southern California
    Posts
    3,588
    Oh so many to choose from... first time in full drag? First time performing? First time asked to perform? Pretty much any year at DragCon? All pretty wonderful.

  12. #12
    Member Zoeytgtx's Avatar
    Join Date
    Oct 2017
    Location
    Middle of AR.
    Posts
    294
    Being out for dinner and accepted as ?one of the girls? with a group of GG?s.

  13. #13
    Senior Member Pumped's Avatar
    Join Date
    Aug 2013
    Posts
    1,910
    Every time my wife says, "I think we need to dress up this weekend!" Which happens fairly often. We have our girl's nights where we dress up in anything from dresses to just some skimpy lingerie and do out nails and sit and talk or watch a movie. Some evenings I get so touched that she has accepted this so well I get emotional and teary eyes. It was just a short few years ago I was afraid the marriage was over.

  14. #14
    Silver Member Kandi Robbins's Avatar
    Join Date
    Dec 2014
    Location
    Kandi's Land!
    Posts
    2,377
    This will probably be viewed as a cop out, but my fondest memory is the last time. After 50+ years of hating myself for this, finally embracing it six years ago, I find complete joy each and every time I do so (I only do so with the intention to either go out in public or take photographs to share on my blog and Flickr page). I have been out well over 500 times, never a negative experience, almost always blissful. I have received hugs from total strangers (no more, these days, sadly), thousands of complements, had drinks and meals purchased for me, shared meals or cocktails with people I did not previously know, etc.... Every time out, a treat, especially now!
    Visit Kandi's Land (http://www.kandis-land.com/) daily! Nothing but positive and uplifting posts!
    Pictures and stories of every time out: https://www.flickr.com/photos/131254150@N06/.
    Kandi on Facebook: https://www.facebook.com/kandi.robbins.167/

  15. #15
    Junior Member DianaW's Avatar
    Join Date
    Aug 2020
    Location
    New Jersey
    Posts
    92
    I'm very new to crossdressing but I don't think I will ever forget how it felt trying on a dress for the first time. I actually let out a soft moan as I felt the dress encase my skin for the first time. And I knew in that moment that my life will never be the same.
    I'm just starting on this new journey. I'm still figuring things out. Who knows where it will lead?

  16. #16
    Aspiring Member dominique's Avatar
    Join Date
    Feb 2008
    Location
    west central scotland
    Posts
    515
    For me it's got to be when I plucked up the courage to go out dressed for the first time. It was a feeling that I will never forget.

  17. #17
    Senior Member Angela1954's Avatar
    Join Date
    Feb 2015
    Posts
    1,033
    After a makeover. I was relatively new to dressing and drove about 100 miles away to get a makeover. I have to admit I loved the look. Anyway I drove home and went to my bathroom to change. I looked in the mirror and thought "I really do look good. I should finally go out" I had never been out in public during the day completely dressed. Even at night I only rode in the car. I decided to take the plunge. I went to a market away from my home. As I got out of the car my stomach was in knots. I passed a man on the way in. He gave me a look that I guess can best be described as a flirt. I did some shopping and went home. No problems. From that point on I never had a problem going out dressed.

  18. #18
    Aspiring Member MonicaPVD's Avatar
    Join Date
    Jul 2018
    Location
    New England
    Posts
    574
    A few years back, I was traveling on business and had a day and a half to myself at the tail end of the trip. I spent that entire time dressed. Went shopping, sightseeing, and even met someone on line who I had drinks with later on. That was the first time that I actually spent more than a couple of hours as Monica and it was just amazing.

  19. #19
    Member Karine's Avatar
    Join Date
    Jan 2015
    Location
    Europe
    Posts
    158
    Mine is pretty simple. It was the first time my SO and I were fully comfortable while I was fully dressing up.
    We were watching TV and cuddling on the sofa as usual.
    Boys who dress as girls have more fun.

  20. #20
    Silver Member Stephanie Julianna's Avatar
    Join Date
    Dec 2013
    Location
    Prospect, CT
    Posts
    2,481
    Hard to pick just one. But they are all the same theme when I am passing well in public. Back in the '90's my then boyfriend and I were clubbing in NYC and we went to a new club we heard about called The Monster. (I think). Crossdressers got in free with their dates and single guys paid a cover charge. When we approached the guy with the velvet rope he politely told me "Sorry Miss, this is for Queens only." With my deepest voice I thanked him for his compliment and he smiled and held the rope open for us to enter and said something like "Looking Fine, Honey." So any time someone asks me when I transitioned or the general public totally accepts me as Stephanie is a fond memory in the making.

  21. #21
    New Member DanniBell's Avatar
    Join Date
    Jun 2019
    Location
    The Midwest
    Posts
    7
    Two stand out: The first time I received attention from a man (a construction worker in a pickup) when dressed. He gave me a wolf whistle when I was in my family's backyard, wearing a short blue skating skirt and a loose red Mexican blouse, as he drove by. Just because I realized I was passing. I was only 14. But, still. The road across from our house was under construction forever, and the only vehicles that went down it were construction. I was far enough away that I felt safe enough to be seen by them after that, and I definitely was.

    And then a couple of years later the first time my friend Kim took me to a party on the West side of town after really helping me put things together. Spent a couple of hours comfortably being her friend as far as anyone knew, feeling safe and confident and not running from attention....

    -D

  22. #22
    Member
    Join Date
    Jul 2009
    Posts
    155
    It has to be the first time I went out in public. I thought: there's no point in half measures so I went to a dressing service who did my makeup and I dressed to kill. At first I was scared but I realised I was doing nobody any harm and I had a great evening looking and feeling feminine and sexy. I've done it many times since and it's always great!

  23. #23
    Aspiring Member
    Join Date
    Feb 2010
    Posts
    752
    My fondest memory was going to an alumni event as Sheren. I was the only trans person there and felt completely comfortable in my own skin, so much so that I now have an alumni (picture) ID card that recognizes me as a female alumni. https://www.crossdressers.com/forums...ner&highlight=
    Last edited by Sheren Kelly; 08-12-2020 at 06:59 AM.
    Warmly,
    Sheren Kelly

  24. #24
    Silver Member Leslie Mary S's Avatar
    Join Date
    Feb 2009
    Location
    Madison AL
    Posts
    2,830
    The first time I went out fully dressed.
    I know, I was cheating because it was for a charity and I had entered into the woman-less Beauty Pageant. Back stage the other contestants where asking me for tip and hint, and help. Some of them didn't realize I was a contestant and thought I was a woman there to help them.
    I didn't win. The winner rightly so, was the person who had raised the most money (a real fireman). But after the show my two of my GG model friends and I went to several places about the small rural red-neck town and had a lovely night.
    I found the batch of photos from that night.
    Here is one.
    Last edited by Leslie Mary S; 08-13-2020 at 03:50 AM.
    Leslie Mary Shy
    Remember this:
    The PINK FOG may seem, at times, to go away, but in fact it just ebbs and flows but does not go away._
    _________________________

  25. #25
    Member Brenda Freeman's Avatar
    Join Date
    Jul 2009
    Location
    Portland,OR
    Posts
    494
    I have many but two stand out. 1st the first time I had make up professionally done put on my wig and I looked in the mirror. I could not believe how feminine I looked and new this was only the beginning. 2nd my wife is okay with my dressing but prefers not to see my when dressed. I had put on a french maid costume with petticoats and dark hosiery to go to a Halloween party at a LGBT friendly bar, thought I looked good and asked her if she would mind taking a picture. She said okay and when she saw me she looked me over took the picture and as I walked away to go she said nice legs. Loved that so much.

Posting Permissions

  • You may not post new threads
  • You may not post replies
  • You may not post attachments
  • You may not edit your posts
  •  


Check out these other hot web properties:
Catholic Personals | Jewish Personals | Millionaire Personals | Unsigned Artists | Crossdressing Relationship
BBW Personals | Latino Personals | Black Personals | Crossdresser Chat | Crossdressing QA
Biker Personals | CD Relationship | Crossdressing Dating | FTM Relationship | Dating | TG Relationship


The crossdressing community is one that needs to stick together and continue to be there for each other for whatever one needs.
We are always trying to improve the forum to better serve the crossdresser in all of us.

Browse Crossdressers By State