Viewing 59 reply threads
New Forums
  • Author
    Posts
    • #628993

      Mine hands down was my outing at superman celebration I was dressed as supergirl and had a great time. I wrote an article about it on here. Whats yours??

    • #628996

      Hi Brandie

      Mine was Stephanie meeting my wife face to face for the first time and then my son and daughter (virtually) later. everything went brilliantly and I had some lovely compliments from all of them 😊 the future is looking incredibly rosy 🥰.

      This all happened last Sunday and I’m still high as a kite.

      Stephanie ❤️

    • #628998

      Hi Brandie

      Mine was last December 12th.

      Christmas night out with 24 of my work colleagues, 21 female, 3 males. Bianca first outing with them.

      The acceptance and kind comments I received was overwhelming, in my gold sequinned dress, heels, best hair and make up. Danced the night away surrounded by my female colleagues in their best glitz and glam.
      Most of the barriers we face are in our heads, when we manage to overcome them we can be our own wonderful self.   If others have a problem with what we do the problem is theirs, I choose not to let it be my problem.
      Bianca x

      • #629031
        Krissy
        Lady

        I think one of my proudest moments was when I finally admitted to myself that my feelings are all female and im happier and more confident being a woman, as for so many years well since I was about 7 or 8years old I told myself it’s just a phase and ill stop when I get older, well here I am 6mths away from my 55th birthday and it’s not gone away in fact the feelings have got stronger and stronger as when I was younger I just was happy wearing tights with knickers but that didn’t last and I started wearing a dress then oh my god shoes! I love them! And I will not be happy til I can live totally as a woman and I mean yes that useless thing between my legs will have to go! The sooner the better! As I thought I could just live 4,5 days as a female and a couple of days as a slightly whimpy man but I know I can’t do that as its all or nothing and I think I’ll be getting the op hopefully by this time next year as it’s something I’ve dreamt of and have always felt this way and it’s not going to change. So begin a new life is on the cards x

      • #629040
        Krissy
        Lady

        Exactly bianca, its not us that have the problem, its certain parts of society that dont like us. We are all happy being the way we are and if people and society dont like it well tough as this is the way we choose to be. Im very happy being a woman most of the time, just feel more uncomfortable as a man as i dont like what the male species is. Oh if i could just live in a city where its only people like us and bio females, no drab men. X

    • #629006
      Krissy
      Lady

      At finally becoming smooth all over and feeling more and more femme

      • #629034
        Krissy
        Lady

        I think being true to myself and saying to myself ” yes this is the way I am and its not going to change, once you are true to yourself its amazing as nothing is scary anymore and you can do and be anyone and anything. X

    • #629021

      Mine was this past Saturday.  I was dressed and out doing the weekly grocery shopping.  Our debit card had not been working recently, so at my first stop (Target) I tried using it and it was rejected.  I paid cash and went out to my car.  My Credit Union has a branch office across the street from Target — but I was Julie, not “Male Me”. If they asked for ID . . . .

      But I needed to get this matter fixed, so in I went.  (To be fair, it’s a branch I NEVER go in to)  I told the lady at the desk what was happening, and she sent me into an office with the manager.  He told me some of their debit cards had been hacked recently, so they froze all of them and have been issuing new ones for a week.  “No problem, we can print one here. I just need your ID”.  Soooooo . . .

      As I handed over my license, I told him a tale. “I’m an actor (which I am) and I’m on my way to an audition for a web series about transgender women.” He didn’t even blink. But he DID compliment me on my look! (I’ll try to post a photo in my gallery) I floated out of there on a Pink Cloud.

    • #629032

      Hi Brandie,  My moment was traveling a bit dolled up.  Floral leggings pantie lines, bust enhancing padded bra, painted toenails with sandals painted fingernails and some mascara.  Stopped to get gas and  stopped by the store and shopped to get camping supplies. Took some doing but glad I did.

    • #629033
      Krissy
      Lady

      I’ve had a lot of proud moments, one of the best was going in a lingerie shop and saying ” oh yes its for  me and can I try it on please” takes guts to be that open I think

      • #629053
        Krissy
        Lady

        Thinking about they are all proud moments when you finally decide this is the way i want to live x

      • #629221

        Had my first bra fitting last year in a local cosy little lingerie boutique by appointment only. Had the undivided attention of the owner and was just treated like I felt she would treat anybody else. I would recommend everybody do this. Now my bras are a lot more comfortable to wear all day, and gorgeous! More  expensive than supermarkets, but what is that kind of acceptance worth?

        B x

      • #646003

        I keep trying to write too much and keep starting over. I will keep it simple.

        My proudest moments are the times when another girl will contact me and tell me I was her inspiration to go out in the world and live. I have had many emails like that over the years and they always make me cry.

         

         

        <script src=”moz-extension://a5db4fb3-7504-42a5-af80-56e622fefbfe/js/app.js” type=”text/javascript”></script>

    • #629041
      Anonymous
      Lady

      Hi Brandie.

      My best moment was when I first stepped out the door in public. It was nothing really special but just walking down a busy street in daylight dressed to the nines. I felt like I was floating. All my fears and anxiety melted away. After so much worry for so long and the unfulfilled desire to be out, I had finally done it! It was such a rush to be where the world could see Michelle and no one was laughing and pointing fingers. The rest of the day was great too.

    • #629042
      ChloeC
      Duchess

      Hi Brandie, well, there have been some moments where I’ve been dressed and felt really good about myself, actually gone away from home or gone swimming in our pool (at our last house), which made me feel more complete as it were, but the proudest was coming out to my mother before she passed.  She had ‘caught’ me around age 15 with some of her things and lectured me on the pitfalls and problems one would face for being gay, which I knew full well I was not.  But I knew I had to tell her, and I sat down with her and said so about a year before she passed.  I’m not sure if she fully understood, but it was something I knew I had to do, and I felt a lot better for doing so.

      Hugs, ChloeC

    • #629046

      Five minutes ago I told a good male friend of mine about Stephanie, he was a little surprised at first but very pleased that I had entrusted him with this news :  )

      He is the first person outside my immediate family that I have told!    I think I’m in need of a drink and a sit down.

      Stephanie xx

      • #629049

        Have a drink on me

      • #629077
        Krissy
        Lady

        Really proud of anyone who reveals their true self as its empowering and you feel so much better 💕 I always found it hard to keep my secret a secret as was always gazing at female clothes and thinking wow hope they do that dress in my size and wow I love them ankle booties! ❤️ female thoughts were always there and always will be because a lot of us were born the wrong gender! I was useless as a male as I always wore clothes that were very femme as my body has always been apple shaped and I look very femme too. Proudest moment when I decided to take the journey and see if I reach the final destination! I’m closer than I’ve ever been as I dress 24/7 and only own I complete outfit of male clothes, so even if I wantEd to go back ( not that I would) I couldn’t, when you reach that tipping point and one looks better as a woman you just have to go for it! Im never going back to the drab world of maleness as I much prefer the femme world, I can be glamorous, sexy, beautiful and be told I’m beautiful too! 😍 that’s so nice when you get told you look amazing! Had it a few times now plus I love killer heels and the male world 🌎 has nothing like that. I love being sassy and sexy 😍

    • #629051
      Krissy
      Lady

      When you know your so much happier in female mode they are all proud moments! Being called “my love” when buying fruit the other day made me proud as I know I’m starting to blend into the female world🌎 x

      • #629074
        Krissy
        Lady

        Its these little things that make me feel happy as that fruit seller made me so happy! As it gives me so much hope that im blending in to the female world! 🙏 thats all i want is to not be noticed like ” theres a 50something stylish lady walking down the road.as my bio female friends taught me to blend in, like dont wear revealing skirts to the supermarket as bio women dont do that, there is a time and place for revealing clothes (friday, Saturday night) at a club or pub? Talking of pubs met some lovely people ( just like ys) at this pub, people all dressed like i do, could be my new home from home as it was chilled and comfy atmosphere too. Xx

    • #629059
      Liara Wolfe
      Duchess

      My proudest moment would be the day that it hit me that this is who I am and that I am happiest when I am Liara.

      Hugs, Liara

    • #629063

      Well I just had my first totally out experience, Thanks to the Ladies at Everyday Beautiful in Largo Fl. Just west of Tampa.

      I had seen a little piece on them on line, Gave a call and set up a in person meet the following week. I live a couple hundred miles away.  Showed up wearing drab outer wear but was underdressed and wearing 4″ black pumps. Walked in tall and proud even if I was a little nervous. They thought I was showing up for a makeup appointment but being I had a full face beard they were confused. (Seems fair, I have been confused about me for quite awhile.)

      I met the owners daughter Faith and we decided on a deportment lesson, I think she was surprised by my wearing heals and how well I did in them. Faith encouraged me to return the following month for a St. Patties day event that would eventually move to a local Gay bar that had a drag show that evening. Not really having a good path I agreed that after fifty years of muddling around with half efforts I should give it my all and see how I felt.

      The next thirty or so days were expensive, confusing and about as exciting as they could be. I ordered things on line, shopped in person, bought way more than I needed in all my excitement. I ended up with three very nice dresses, two different pairs of heals enough thigh hi stockings to outfit an entire team of cross dressers. And underthings galore.

      On the morning of the party I woke in Tampa and drove to Clearwater Fl for a Manicure pedicure appointment at Hot Stone Nails and Spa at the recommendation from Faith, I had reached out well in advance explaining what I thought I wanted and that I was clearly a man. They were very understanding and more then willing to help. I thought I was getting acrylic nails but after looking at my nails they decided to work with my real nails. what a thrill.  Beautifully done pink and white French tips. Then on to my pedicure and the same color on my toes. Pedicures are a wonderful treat, I love them. I had asked about fake eyelashes and they had exactly what I needed they also did a trim and waxing on my brows. Understanding I needed to revert to boy mode the following day. I was so happy with what they had done I could have stopped right there.

      A couple miles away I arrived at Everyday Beautiful just in time for my appointment.  Shortly after arriving Faith had helped me select the best dress and everything else. I purchased breast forms and a wig from them. then it was up into the makeup chair where Faith and her mother Laurie tag teamed my makeover.  Honestly I looked much better than I thought possible, Thats to say if you had a picture of me before and after you would not be able to tie the two together.

      After a little wait a couple more girls arrived for makeovers and makeup help and new wigs. (they specialize in real hair wigs.) Shortly the party began with about ten girls we snacked drank a little wine and got to know each other.

      I was the only one out for my first time so it was nice to ease into it.

      Then we all caravanned over to Quench a local gay bar that was having a drag show that evening. I had a good time it was a cold Florida evening and the cool breeze under my dress was a thrill.

      It was fun being out and especially with some like minded friends.

      Funny thing the following morning, while having breakfast dressed drab except for my beautiful nails. I did get a look or two but really didn’t mind. Overall a very positive experience.

      • #629087
        Anonymous
        Lady

        Hi Dani.

        Did you keep the beard?

        • #629205

          Oh no, Beard was gone for the first time in fifteen years, Shaved everywhere. Guess I thought I would get some action. Silly me.

          I need to figure out how to up load photos, So I can show everyone.

           

      • #654966
        Dawn Judson
        Ambassador

        Laurie & Faith are the best. They have monthly meet-ups. I try to attend whenever I can.

         

    • #629069
      Krissy
      Lady

      I think every moment is a proud one! My proudest was 6mths ago when i started living full-time as a female and stopped kidding myself that i was ever anygood as a man, ive always known i should live as a female as everything i did as a male felt wrong and fake, i used to kid myself that i could stop feeling femme but i just couldnt, i used to feel like a fake when i presented as a male and all the male clothes never fitted properly as i had these big old hips and almost bra size boobs too, so it was quite easy to make the change to dress as a woman and ever since i told myself that this is me, ive not looked back, i always used to feel so natural in femme attire and it fitted properly too, my mum used to say she always wanted a girl and she would pray that i was born a girl, well youve almost got your wish mum as im so close to the femme world as just one thing to lose and im there! X

    • #629075
      Angela Booth
      Hostess

      I think it was when I finally decided that I couldn’t stop Angelas progress. I had to tell someone and that someone was my mother. After telling her then having a talk, I was so proud to hear these words,’Well it doesn’t do any harm’. 

      The rest, as they say, is history.

       

    • #629085
      JOJO
      Lady

      Plain and simple: The first time I was addressed as “sweetie” when I was “dressed”. I had an inward and outward smile all at the same time.

    • #629105
      Revel
      Baroness

      My proudest moment(s) was when I finally had the courage to dress up and reveal Revel to my parents in-person. They were so kind, accepting, and supportive. My Mommy passed away so I’m glad that I did that when I had the chance before it was too late.

      • #659816
        Stevie Steiner
        Managing Ambassador

        Proudest, yet with regret for me Rev.  I waited too long with my mom.  Though she is still with us, she suffers from advanced Alzheimer’s.  I did  tell her and my family a couple years back, I wish I would have told her sooner when she could have appreciated and comprehended what I was saying.  And who I was deep down.

        Stevie

        • #659904
          Revel
          Baroness

          Stevie,

          Thanks for sharing that, and it’s so sad to know what’s happening to your Mother, but thankfully you told her about yourself. It may have been too late, but it’s better to be late than never. I’m so glad that my Mommy knew I’m a CD and supported me before she died. Once your loved ones are gone, there’s no going back.

          Rev

    • #629106
      Anonymous
      Lady

      Yesterday when I told my friend I was a CD and it could have changed how she looks at me in a very bad way forever. Instead she held my hands while I told her and hugged me twice after and was so happy for me.

      • #629126

        Thats how I felt when I came out to a female friend. Instead I got your body is a reverse triangle you need to dress for that. We are the same size shoes so I can pass on the ones I dont wear anymore.

    • #629150
      Janine
      Lady

      There’s been so many best moments, since I began crossdressing. One of my proudest moments was the day I went to Marathon Florida to see what its like to live as a female for a few days. I’d been out before in public, but I was always near where I live. This was different. I was going far away from where I live, dressed as a girl and didn’t have any male clothes with me. It was so exciting to travel as a girl who is going on vacation. It was something that I had always wanted to do. I was determined to see what its like to be seen as a girl and do things that girls do when they are on vacation. It was a incredible experience and I still think about it. Now that the Corona virus is not such a issue, I plan on doing it again this Memorial day weekend. I’ve already made reservations at the resort where I had stayed. Looking forward to another incredible weekend

       

      • #629209

        If you get a chance continue down to Key West, Very open to all.

    • #629170

      I guess I’m shallow. My two best moments were about a year ago when a fourty year old wanted to take me home. That same night three drunk men were talking about which one of us. Me or my wife they would rather have. One of them chose me. Then a gentleman this winter said I could sit on his lap anytime I wanted. They were very busy. I guess I am shallow. Sorry. My wife thought it was funny.

      • #629207

        I think those are couple of great moments, very validating. And having your wife with you to witness and share is really nice.

    • #629171
      Caty Ryan
      Baroness

      As one of the more “mature” (as in age) CDH members I have experienced many events over the years that gave me the “warm inner Catherine glow”.

      Had many makeovers, been shopping in malls as Caty, (complete with the obligatory  “first visit to the ladies”), country drives, bought, sold and given away many outfits and other clothing pieces. The one thing left on my to do list is a femme bra fitting and that’s happening in about 3 weeks.

      But if I had to pick one, it would be my attendance at “Transformal 17”, the Australian version of Keystone, Diva Las Vegas, etc etc.

      OK much of the time spent there was marred by a serious and very painful lower back problem, but I still managed to make the Saturday night formal as “Scarlett O Caty”

      The “complete and unexpurgated” story can be found here

      https://www.crossdresserheaven.com/transformal-was-great-but-i-wont-be-going-back/

      Happy dressing (and reading)

       

      Caty

       

      PS Oh I also have taken much satisfaction about becoming a “mentor” to CD’s younger than myself and being responsible for setting up a lovely private email group of “gurls” from many countries.

       

      As the old saying goes, “they know who they are”.

       

       

    • #629227

      One memory that stands out was during an unexpected interaction with a woman at a restaurant.  I was sitting there, mostly empty, and ordered and then they move tables and it fills up for a poker contest with everyone like 6 feet from me.  She lost and came and just sat next to me and started talking.  It was the first time I ever said “My name is Nancy.”  The moment and feeling of saying will forever resonate with me.

    • #629622

      I’m member in kinky forum and one male saw my pics and asked if I could dominate him. After few messages he suddenly noticed clearly visible gender  from my profile. He was horrified and blocked me. It felt weird but at least he was enjoying my pics.

    • #629654

      I’m closeted so I haven’t had any moments in public but I would say my proudest moment would be the night I wore lingerie in front of my boyfriend for the first time and he told me how beautiful and gorgeous I looked in it. I was really nervous about him seeing me dressed for the first time so to get his admiration was heaven for me.

    • #629667

      Great question.  I probably could come up with a few things but one sticks in my mind that’s is fairly recent.  Some background,,,I came out to my wife last year and we are working through it and as long as I don’t want to transition.   We both know that while we are comfortable with where we both feel today, things could change but we are focusing on the today not tomorrow.    I’m lucky to say the least.  Being out to my wife allows me to start to get out which I did planning a 3 day trip which involved me meeting s9me CDH members en drab at lunch, going to dinner with a. Few as Carole, attending a party as Carole, getting a makeup lesson as Carole, and then another dinner with friends as s Carole another group get together.  Yes that is a lot but I have been on the closet for so long I let it loose.

      You might think that one of those planned events was what I was going to say was my proudest moment.  They were all wonderful but here is what really did it for me.  I went back to the hotel after the last group get together.  It was about 10pm and I was calling it a night and I was pretty proud of all I had done.  The hotel was lovely and had a beautiful bar…could I actually go to the bar by myself, totally unplanned and not knowing a soul in the bar toast to my wonderful days as Carole.  Would they be friendly, hopefully quiet, would I be accepted?  All questions going through my head and giving me reasons not to go.  But I did it!  When I walked out of the elevator the bar was packed!  Omg what do I do.  I spied one single seat open and I beeline to it said down and ordered my lemon drop martini.  Next thing you know a wedding party had ended and many people came up.  I was in the midst of all cis gender people .  The only one that’s not.  I steeled my nerves and kept to myself and my phone.  Somehow someone made a joke and next thing you know I start chatting with a younger couple next to me.  Two hours later it was last call, I had bought them Adriano and them me.  We talked about marriage, food , shoes, travel anything you can imagine and even exchange numbers so if they were visiting my town I could help them and visa versa.  I walked back to my room so proud feeling so accepted and empowered. It was wonderful!

      Had I not done that I would have missed the opportunity to be Carole unplanned and unstructured.  My advice which is a line for a movie where a family buys a zoo.  During it the son is interested in the girl and he thinks he missed his opportunity.  The father played by Matt Damon gives him this advice…”sometimes all you need is 20 seconds of insane courage, embarrassing bravery and I promise something good will come of it”…. I took his advice and that happened.

      I encourage all to do the same !

      Love u all

      Carole

    • #629800
      Anonymous

      Mine came when a very attractive man offered to buy me a drink in a bar in Palm Springs.  I declined, but so wanted to say yes.

    • #630750

      For someone who is very shy and not very confident as a male, my proudest moment so far was building up the courage to see a psychiatrist and psychologist about my crossdressing and feelings. They gave me the formal diagnosis about my being transgendered. This was the first time I had sought help. Being completely honest with someone for the first time about how I felt, was both liberating and frightening. I have not started transitioning. I don’t think I’m strong enough for that yet.

      The other proud moment for me was when I was about 17 (and despite being so very shy), walking into a lingerie boutique and shopping for my own underwear. I still remember what I  bought on that day. Until then I had been wearing and borrowing my mother’s lingerie. After that I was also proud of the fact that I began to let the shop assistants know that I was shopping for myself. This was such a big step for someone with little self esteem, but I so needed to do it. I could relax while shopping, spend the time to look at everything and then try on items that only buy items that I really liked and looked good on me.

      These are my proud moments.😌

    • #646008
      Anonymous
      Lady

      I have two proud moments…the first was needing to go mail something and thinking no one would be there at the time I went. I was dressed and just didn’t want to change so off I go, when I got there there were so many cars still there. I sat there thinking I can’t, then I told myself I have as much right as anyone so I got out walked into the Post Office and mailed my letter and walked by at least 10 people coming and going. The other was last weekend. I go out frequently as Sandy but this would be different. I went to a Renaissance Fair dressed and this time instead of a few people in a store there had to have been at least 3 thousand people there. I so enjoyed myself with all the other people and was called My Lady so many times and had one woman ask where I got my festival dress.

       

    • #646009
      Patty Phose
      Duchess

      There’s so many, but if I had to be pinned down to one, it would be, while dressed in my Daisy Duke outfit in my little shorts, platform wedge heels and pantyhose, I went in a store and bought pantyhose. it took several false starts before I did it. Incredibly scary but amazingly exciting.

    • #646025

      This is a great topic:

      1. coming out to my wife and after a lot of conversation and therapy together we are much happier together and I also get to be Jessica without hiding, within limits.

      2. coming out to 2 of my friends and they being totally accepting!

      3. actually happened last week, I was home simply dressed in a cute top, skinny jeans, wig and lipstick, nothing too fancy and no beard cover at all. I received a package from the UPS guy and he called me mam, even though he definitely knew I wasn’t a cis-female. It was just a nice feeling to have a stranger acknowledge me as a woman!

    • #646104
      Amy Oxley
      Lady

      My proudest moment was telling my girlfriend (now my wife) about my crossdressing and her wonderful reaction. To this day she is the only person who knows, and I am incredibly grateful to be able to share this part of me with her.

    • #646108

      Years ago I kept close to home when I dressed. And I always kept my head down and never made eye contact with anyone.

      I worked hard on all things to reach a goal of “blending in”.

      That day came and got dressed and packed and took a trip to Ottawa.

       

      Alanna

      xoxox

    • #646113
      Fiona Black
      Baroness - Annual

      My proudest moment was the first time I went out dressed which was last month. I was hardly nervous at all and felt comfortable for the entire 3 hrs. that I was out. I also felt a sense of satisfaction for having worked up the nerve to do it. Since then I have been out 4 more times and love it.

    • #646131
      Amy Myers
      Baroness

      This is a surprisingly difficult question the answer, as I’ve been out in public for a few years now. The best I can do is a three way tie of sorts. My first trip to a mall where I was approached and a hard sell pitch at me for some high priced cosmetics. The nearly ruined my day, but I went to a coffee shop to have a coffee and settle down, determined not to let them ruin my day out! (written up here)

      Last Fall I was asked to participate in a trans fashion show at a nearby gala, as most entertainment was on hold due to the continuing restrictions here in Ontario. What a riot, and it certainly helps to give one confidence! (Also written up here)

      Though the proudest is perhaps when I told my adult kids and their SO’s about Amy early this year, and everyone was completely accepting, and now 5 months or so later nothing has changed in my relationship with them.

      Amy

    • #646153
      Denise Little
      Duchess - Annual

      My proudest moment was a month ago. I ventured inside a Starbucks and was greeted by a young gentlemen who went out of his way to make me feel comfortable and someone special.

    • #646609

      Hi Brandie, mine was going to a concrrt in Hobart, where the Aussie band, Human Nature were performing, dressed as Jane.
      My wife and I had a great time, singing along and most people just smile.
      Well done Brandie, live your life enjoy.
      Jane

    • #646737

      I was at a resale store that catered to tall and plus size ladies. The owner (who knew I was a CD) complimented me on how beautiful I looked in a dress I tried on. She may have just been trying to make a sale, but she made my day. I did end up buying it.

    • #650353

      My wife told me this week that she loved having a husband that crossdresses.  It makes her/our life interesting and fun.  By far my proudest moment.  Looking forward to exploring these comments with her.  Inga

    • #650793

      There many big steps for me as far as what I have done but I would say “Pay it Forward”

      By this I mean helping others achieve a degree in their journey or evolution that may have been holding them back.

      When I became an out in public person I realized that it opened a Huge door. One of the things I like to do is help others take “That first step in public”. Maybe it’s going shopping or meeting at a restaurant and coming to their car and walking in with them. Promoting lunches or other activities that they might want to do but never could do it on there own. I’ve never kept or made count because it is not about numbers, it’s about people but as I type this I have to think it’s a few dozen or so but I’m not done yet!

      Sandy

      • #650824

        Hi Sandy, a noble endeavour to help crossdressers to realize their femme dream..it is about getting out in oublic whe you feel comfortable.
        Passing, for most of us is an effort, but My wife and I have a regular shopping dat, nd weekend trips. A loving time together.
        Well done Sandy
        Jane

        • #654957

          Jane, Great to hear you get out with your wife. You what I’m talking about when I say an “entire new world”

          Sandy

    • #650866

      Hi all
      I think my proudest and happiest moment was with my incredible wife. I had just finished sewing a new dress (I’ve made quite a few), and had tried it on and modelled it for her. She said it was a great fit, and that i looked lovely in it! I couldn’t be any happier!
      Jenny xx

    • #651063
      Beverly
      Lady

      I was in man mode when I looked in a jewellery shop window and saw a ring I loved. I went in and asked what sizes they went up to. When the assistant told me the sizes I said “actually its for me” so I tried it on and bought it. I wear it whenever I go out.

      • This reply was modified 1 year ago by Beverly.
    • #651311

      Hi Brandie

      Mine is probably going to be very different to everyone as I have just started crossdressing however my proudest moment would have to be ordering my first set of clothes the other week and wearing them for the very first time.

      For months (even a couple of years), I have been trying to build up the confidence to buy my first dress, bra and underwear and never had the guts to do it.

      Only a couple of weeks ago, I finally had the courage to do it and when I got my first order, I jumped straight into my clothes and felt beautiful and at peace.

      Might not mean a lot to everyone however it was the most proudest moment for me (so far).

      That will probably change for me (no doubt) in the future but I wanted to share my story.

      Lots of Love,

      Jacinta xoxo

    • #654978
      Jasmine
      Lady

      I think for me it would have to be when I came out to my brother cuz he’s like the 6′ 6 high schools jock Macho Man type person and when I told him his only answer was I already knew you didn’t have to keep it a secret for so long and I was like Jesus Christ

    • #658699
      Cassie Jayson
      Duchess

      I have had so many so far. Getting my hair colored twice, getting my nails done 4 times now. BUT the biggest is coming in 2 weeks at my high school class reunion, I am sooooooo excited and scared. Having my hair colored the day before and my nails done the week before and have a dress all picked out. Can’t wait to share all this with everyone here!!!!!

      . Cassie

    • #659701

      A few years back being dressed and my wife and I were at a club. I man walked up behind me and whispered over my shoulder that I was ver pretty and had an amazing body! I turned around and thanked him for the compliment and he looked at me wide eyed and said ” omg you look amazing I thought you were a real woman!” I laughed and said ” well I am on the inside lol” my wife laughed and we all talked for a while.

      As he went to leave he thanked us for chatting, nodded to my wife and kissed me on the cheek. He also whispered something very naughty to me that I kept to my self 😈 lol.

      • #659836

        Whatever was in that whisper, Riley, would have been the highlight of my life.

        Lucky you. I hate you!

        Of course not.

        With affectionate jealousy,

        Diane

    • #659715

      Mine was probably the time i got locked out my office. I had come to work dressed several times already but my office at that time was in a corner and many of the people in my department had still never seen me dressed. At the time i shared an office and my office mate had an interview with a student that needed to be kept confidential. When the student arrived i went down stairs to the computer lab to continue working. After an hour, when the interview was supposed to be over, i came back to the office and it was locked. I had my phone but my purse and keys were still inside. I sent a text to my office mate to see if she was around but no response. I went to the main office to get a spare key but it was lunch and everyone was gone. So, i went back to the lab and worked till after lunch. Still no one. While i was looking around and wondering what to do another proffessor and a grad student appeared. It was the first time i had mer the proffessor so we introduced ourselves. I found out then everyone was down on the quad at some homecoming activities. So, i went down to find a key. I had to take my heels off to walk across the grass. It felt very sexy to carry my heels and walk barefoot across the lawn. Pretty much everyone in the department was there, as well as tons of other people from the university (campus wide cornhole tournament) and many saw me dressed for the first time then. There were a few questions and everyone was very kind, but eberyone treared me just as they always did. I got the keys, retrieved my purse, went back to the quad to return the keys and then went to my car a few blocks away.

      Its funny how a small mishap like getting locked out of your office can turn into one of your fondest memories. If anyone wants a visual, you can see a pic of the outfit that day in my pictures. Its probably my favorite ensemble, though my face looks goofy in that picture, lol.

    • #659735
      Rhonda Lee
      Baroness - Annual

      Hard to isolate my proudest moment, as I have had so many, but I will share a few:

      – My daughter, a psychology professor, leads a psychology club that meets weekly at her university. She invited me to speak to her group. Met me as Rhonda only when I arrive for the presentation on crossdressing. Faculty were present. She asked if I should introduce her as her father. I said she was free to do as she pleased. She did. I was very proud of her. She arranged subsequent events which attracted standing room only crowds, including top university officials, giving us a chance to educate. Recently she won a top university award, in part for her interest in promoting needs of the LBGTQ community. She and other university officials may help us get an IRB for a worldwide study on crossdressing that would satisfy standards so as to be viewed as credible for medical science.

      – I (as Rhonda) was asked to fill in for the minister of an MCC congregation on vacation. I focused my message on the importance of acceptance (removing the log from one’s own eye before removing the spec from another), brotherly love (one of the greatest commandments), and apologized to the congregation for having previously had negative prejudices that distanced me from caring to understand or associate with the LGBTQ community. All present made me feel very loved, welcome and comfortable

      – A member of that congregation asked me to play piano for her holy union ceremony with her lesbian partner… I wore an elegant dress she had donated to me from her wardrobe. Her partner dressed en drab. A wedding photo highlights the diversity of the three of us, of different races, sexual preference, and gender presentation, all accepting of each other and of one spirit.

      – I, along with a WPATH Board member and the chairwoman of Tri-Ess, presented to an annual conference of WPATH in an effort to revise the Standards of Practice to clearly include crossdressers among those considered “transgender,” and entitled to be treated as part of that community with respect to medical care and other privileges afforded that segment of the population. This was warmly received, revisions made, and led to modification of their training of others (primarily doctors and counselors) in their GEI (Global Education Initiative.)

    • #659739
      Anonymous

      I know this doesn’t sound like much but I have been called Ma’am a couple times when out dressed.  Do you think they thought I was a real woman or just being nice to a cd?

       

      Kerri

      • #659779

        I often wonder about things like this. Like, when people say i look nice, do i really or are they just being kind?

        I got called ma’am once entering a store. I was elated, then started doubting and wondered if that ma’am was meant to be sarcastic.

        Its probably best to take whatever you can get with grace and not overthink it.

        • #659814

          Don’t overthink it, Sarah. You were out and about. That’s what counts.

      • #659813

        Nice Stephanie!

    • #659780

      My proudest moments seem to be adding up.  The first being telling my wife.  The second was going to a hotel bar alone even though it was full and chatting a couple up and then finally accepting myself …I broke down in my car real losing how embarrassed I was of who I was since grade school…that started me on a journey of acceptance.
      So my newest is that I no longer have boxes of clothes…I have a wardrobe. I hired a stylist and we went through my existing clothes which was a mixed mashup of outfits most wrong for me due to size, design or color.  She figured out my colors, face size and what would look best in me.  The best day was shopping together.  Omg my nee outfits are amazing. I look younger and skinnier 😲😀.  My confidence has gone up a multiple of 100 and I feel great. More of a woman !  Look out world here I come !

       

    • #659784
      Anonymous

      I’ve had a few proud moments.  They include:  the first time I went out in public en femme; my first makeover (I was amazed at the image of a beautiful woman I saw in the mirror when it was complete.  The results left me speechless.  My reaction almost made the cosmetologist cry.); and when I was out shopping en femme and the lady behind me in line at the checkout complimented me on my appearance.

    • #659812

      I would say going to the nail salon. No breast forms or lipstick, but had a handbag and I was dressed VERY fem.

      Note. I went to me bi-weekly therapy session as the “full Diane”.

      What happens next? I can’t wait.

      • #659916

        Goodmorning Diane, a pleasure to read about your best moment dressing. We live our realities inside, so when we get too realize our dreams, we are having a great day.
        Itook my wife to the airport yesterday for a trip to Sydney, and I dressed up for the trip.
        We get used to being stared at, but we live our life and enjoy it.
        Best Wishes
        Jane

    • #659827
      Michelle
      Duchess

      Mine would have to be the night a little over a year ago that I went into a gay club for the first time. I had gone over to a friends house and on the way home decided to stop at the club, and after about 15 minutes sitting in the parking lot I finally got the nerve to walk in. It was a great moment for me, the bartender made me feel at ease. I now go there often in femme to watch the drag shows they have. And my confidence level has continued to grow with each time I go.

    • #659840
      Elaine
      Duchess

      An old lady friend was on vacation at a nearby town. Wife and I went to visit. I spent the day en femme with wife and her. Elaine’s best day ever!

    • #659843

      The first time I dressed as Jenny, all for the pleasure of another man.

      Watching how happy and excited my fem appearance had made him made me feel very proud. I can still hear him saying “oh, wow” as I walked into the room. A life changing moment.

    • #660071
      JJ PHoser
      Lady

      I am almost completely an at-home dresser and/or underdresser in public, mainly hosiery and occasionally some lingerie. I have only worn nude pantyhose with men’s shorts in public a couple of times.

      But I am comfortable shopping for myself in public. My proudest moment is probably very minor for most of you in this forum. I was checking out with some pantyhose at a T.J. Maxx. (American discount clothing chain. I’ve often to find very fine hose there at great prices, including luxury brands like Wolford.) The middle aged cashier smirked and asked “Are these going to fit you?” I answered, with a completely straight face, “I’m not sure, but I have a couple pair just like these, and they seem to fit me just fine. After you get off work today, would you like to help me try on a pair, and let me know what you think about the fit?”

      She turned very bright red, and stammered something completely unrelated to my question.

      • #660082

        Good morning JJ
        Welcome to CDH, a great place to express your inner beauty. Whether at home or outside, it is your choice.
        It is a great feelinh to walk around a mall, have lunch. Also a werkend trip enfemme can work miracles.
        Hold your up, walk with a smile on your face. Enjoy.
        Best Wishes
        Jane

      • #660140
        Rhonda Lee
        Baroness - Annual

        Bravo!

    • #660088
      Jennifer
      Lady

      Hi,

      My proudest moment was when I got the courage to get fully dressed and drive to a friends house for some intimate time. I was so proud to let the woman in me come out and please my partner.

      Jennifer

    • #660218

      A whole day spent in a nice one piece dress. I did not go out but spent whole day in dress.

    • #669491

      Im a truck driver and used to deliver paint to home depot store in west virginia. I started at the company in the winter so when i was in the truck i could wear my breast plate with out worrying about some one making a rude comment. When i got out i would wear my bulky winter jacket to hide it. I always wore my tight jeans and shirts.i also wore a wig that i would take off when i got out. I had just recently started to openly wear female clothing after 31 years of doing it in secret. Winter was coming to an end and it was getting to hot to be wearing a winter coat all the time. I had 10 stores a week that i had to go to. My proudest momment was when One day i got out with the wig on and no winter coat amd went in to deliver the paint. My heart was racing at what people would say. To my surprise i wasnt treated any different They still talked and joked around with me at every store but one. This store would unload me but they didnt talk i wasnt allowed to be in the store they left my paperwork in the trailer and knocked on the wall when done. The other 9 stores even called me chloe and treated me like a female. There was questions they had but they werent rude. From that day on i went to west virginia as chloe all the time. I would get compliments on my outfits and dresses. I even had one of the managers invite me to her house and give me a basics on applying make up. I mever felt more proud and happy as i did that day.

    • #669492
      Anonymous

      I’m a bit wary of contributing to this, as I don’t want to be seen as a little black raincloud on what is a refreshingly positive forum! But, as that relative rarity of someone who got into cross-dressing by being forced, there have been a couple of moments from my youth that I can look back on.

      The first comes from my school days. Apart from the first time, when the sheer shock of the situation caused me to lose it completely, I always kept my composure around those who were responsible for my situation as I was determined not to give them the pleasure of seeing how much I hated being in a girdle.

      The second time was when I was a student – this is a more positive thing I guess, as it was my first step towards acceptance. I’d had to start underdressing again after leaving school – a consequence of indoctrination and psychological damage after the school years – and I hated myself for it. After a couple of years of wallowing in self-pity, I had returned to university for the start of the third year. I remember getting dressed that first morning and seeing myself in the mirror – black tights (pantyhose), bright white long-leg panty girdle, bright white longline bra overlapping my girdle – and for once I didn’t get that surge of self-loathing. I was long since used to the feel of wearing it, and for the first time ever I could see myself dressing like this for the rest of my life and not feel ashamed or appalled at the prospect.  I can’t say I had an “Saul on the road to Damascus” type epiphany and everything was sunshine and lollipops from then on. I still had my bad days, but that was the first of me seeing a light at the end of what had been a long, dark tunnel and realising the journey wasn’t going to end with me finding a way to stop wearing corsetry but instead finding a way to be able to live with wearing corsetry.

    • #669500
      jennifer
      Lady

      [postquote quote=659904]

      I went to walmart at christmas time ,it was real crouded.i got what i needed and went to self checkout and i was getting my debit card out when the teller said to me mam and i didnt pay atention and she said again mam this lane is open ao i checked out and left on cloud 9 as it was my first time out as a female

Viewing 59 reply threads
  • The forum ‘Personal Crossdressing Stories’ is closed to new topics and replies.
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?