Viewing 31 reply threads
New Forums
  • Author
    Posts
    • #723135

      I know that when I first started crossdressing, I always had dreamed of being just like the women that I admired and thought were very beautiful.  Then as my desire to emulate them became stronger, I would always have a lot of self doubt that I not only would or could be like some of the beautiful women that I saw, but I’d never actually look anything like a real woman.

      Well last weekend, I had purchased a new dress and couldn’t wait to try it on.  After I did all the makeup, and body shaping, I started my usual photo routine.  I was prepared to delete a bunch of pictures, but I kept getting ones that I really liked.  I only deleted a few which was very unusual.  So I went back and took some more, with the same result, not many deletions.  So, there I was, all dressed up, and admiring my pictures, I couldn’t stop looking at myself in the mirror.  So, I thought that I had finally done something that I had never thought that I could do, which was to be a passable woman.

      I was wondering if anyone else had experienced that kind of revelation, kind of a crossdresser culmination, or peak?

      It was a magical night, I had a hard time getting to sleep after that.

    • #723144

      I didn’t ever really give it much thought when I was younger. Knowing what I know now, take away 40-45 years, have the same income I do now. I would have transitioned back then. I have always viewed (and fought it) myself as a woman. I don’t pass, so I don’t go out, but somedays I fully dress as a woman in my home. I’m married and my crossdressing broke up one marriage (I’m on my third and final one) My wife knows but request I don’t free fully in front of her. She is still of working age so it works out. I never saw my self fully dressed as an adult. I used to sneak my mother’s clothing when I was home alone. () I have no sisters.It is kind of strange to dress now because it means so much to me. I thought when I was younger it “was just a phase” I was going through. I realize now it wasn’t a phase, but a part of what makes me, me.

    • #723147

      Thanks for sharing Jennifer, it is just the best when you realise you look so much better letting your feminine out to play.
      It’s so much fun and interesting, putting a look together, accessorising, make up etc, and a never ending source of different choices. My journey just keeps getting better and better, never would have thought 5  years ago that my life now would be so much richer and joyful.
      My latest indulgence is trying corsets and clothing with corsets incorporated, not the easiest to tie up the back yourself, but once it’s on I feel (and think I look) like a million dollars!

      B x

    • #723149
      Anonymous

      Jennifer
      Embrace those magical moments and memories ✨️ They get better with time and bravery
      Hugs Ginger

    • #723151
      CelesteCD
      Lady

      Jennifer, never in my wildest dreams did I think I would be at the point I am now.  Each step forward has had some missteps but I kept pushing my boundaries and moved forward. If I had a dollar for every time I said  to myself  “Oh I’ll just take it to this line” I’d be rich.   I came to realize that line was in sand and meant to be passed over and over and over and over….while  I have surprised myself on this journey and accomplished a lot I still feel like there is so much more to explore.  It is fulfilling to look in the mirror and exciting and nerve wracking to wonder what is ahead of me.   One thing I know…I keep taking steps forward.

    • #723163
      Leah
      Baroness

      our journey is a constant work in progress. If you would have asked me 10 or 20 years ago as to where my dressing is currently…I would have said no way.  It is nice to check some of those dressing up boxes

    • #723168

      Oh God YES, Kristen!
      To put my story in perspective, I didn’t put on my first dress until I was 31. After that for thirty years it was only sporadic, as I was deeply in the closet, with no one knowing, including my wife (now ex). Why? Many reasons, shame and guilt because of my Christian faith, work, rural area, etc. When I did dress I neither had the knowledge, experience, money, or time to even come close to passing (although I did venture out a few times with some humorous results). So I wasn’t a very pretty woman, not even close. Heck, I didn’t even know who or what I was. I certainly did not know myself as Jules.

      I used to only dream of dressing, going out, passing (kind of…lol),and living part time as a women, me, Jules.

      Then fifteen years ago I went through an unexpected and sudden divorce. (Nothing to do with my CD, as far as I know). Moving forward I met a wonderful accepting woman, now my beautiful wife, who I told before we tied the knot.

      Fast forward, with my wife’s blessing and help amid my male self’s chuckles I have finally the time, money (sort of) to have found myself, Jules.

      I love the thrill of transforming from my drab caterpillar into my feminine butterfly. Now when I look in the mirror I see the woman, the happy, confident (sort of), beautiful (in my eyes at least) women I feel I am. And that soft feminine joyful complete women is the one I once dreamed of, doing things she never thought she would. When Jules has her butterfly wings on she soars even higher than I ever thought possible while in that terrible dark confining closet.
      Hugs
      Jules

      • #723179

        I love that story, Jules,  good things come to those that wait.

    • #723202

      I had no idea or dream of being were I am now, and can only imagine what the future holds.

      I started with panties for just a few minutes as that was all I could handle. I had no plan to fully dress.  It was an experiment to see if it would stop the feelings that came over me with just panties for a few minutes.  I ended up fully dresses in “borrowed ” clothes hoping that my desires would stop.

      I now own an ever expanding wardrobe that gets to see the light of day out in public every day after work and on every weekend.  I am looking for ways to move my clothing choices into work as well. At this rate I will own no male clothing and everyone I know will know about my fashion choice.

      It does not seem to be out of the realm of possibility to talk to Doctor about other options.  I am terrified of going even further.  But then 4 Yeats ago I did not own any clothes of my own, and never thought I would be getting waxed, woried about washing instructions, fussing over mascara, lipstick, and have a beauty routine.

      This is the great thing about life, if you are open for what comes up you never know were you will end up.

      Paula

    • #723208
      Emily Alt
      Managing Ambassador

      This sounds like my 1st makeover and photo shoot.  Pretty much a life changing event.  The reflections in the mirror….the 100+ photos….stunning!  What I was seeing wasn’t an illusion….that attractive woman was me.  Looking good breeds confidence.  I knew there was no way I could stay hidden.  It was the beginning of a new chapter…..

      I couldn’t have imagined on that fateful day where my journey would take me.  Joined CDH.  Made hundreds of new friends.  Socialize with dozens.  Got comfortable in my own skin.  Tried on a few labels.  None stuck….until I got to trans.  Now I’m 18 months into transition and living a life I never thought possible.

      If I had a crystal ball 30+ years ago I would’ve done this way sooner!

      Good makeup and good photos CAN change your life….

      /EA

    • #723212
      Angela Booth
      Hostess

      I would dream but never thought I would be where I am today, just shows dreams can come true.

    • #723215
      Fiona Black
      Baroness - Annual

      Jennifer,

      It is indeed a very exhilarating, feminine feeling that washes over you when you finally realize that you can dress as a passable woman.

      For me the moment when I decided that I could be a passable woman was last April when I tried on my first wig. Before putting it on for the first time, I put on a nice dress and some lipstick. After putting the wig on I walked to a room with a floor to ceiling mirror, saw the attractive lady looking back, actually muttered “oh my” and sat down and stared at myself for 20 minutes. I then decided that the world was going to meet Fiona and I was out in public a few days later. I haven’t looked back since and now live virtually my entire life dressed as a woman.

      And if you had told me at some point in the past that I would be doing this I would have asked you what you were smoking. It had never crossed my mind that going out en femme was even remotely possible.

      Fiona

    • #723216
      Cassie Jayson
      Duchess

      Jennifer, I can imagine the high you were on from your photo session. You had much more than a pink fog you were deep in the pink soup.
      I know for me 10 years ago when I sometimes spent the afternoon crossdressing in the house often connected with arousal I would feel MUCH shame and relief at the same time.
      Then it was 4 years ago this month I started dressing in fem almost every night. By fall I had been caught cross dressing, and moved at a dizzying speed down the CD road. Now had my hair colored 3 times as Cassie, had my nails done at a salon at least 7 times, gone to sing as Cassie at my mother’s grave for the last 2 mother’s day and even gone to my HS class reunion as Cassie.
      If someone would have told me I was going to do all this 10 years ago I would look at them as if they were totally insane.

      BUT here I am as Cassie and loving it!!!!!

    • #723233
      Melinda
      Lady

      The short answer is no. I am temporarily in a two steps back pattern, but it’s nothing serious. My wife is considering attending a Crossdresser event as my date, which is hard to believe, and I may need seeing to believe it anyway. It’s been a long hard journey and it’s still difficult. One of you mentioned that money makes it easier and I concur. I have way more items than I ever imagined for sure. My marriage counselor asked what else gives me the same pleasure as dressing up. Really, in terms of a visceral gut feeling, nothing does. I have things in my life that are more important to me, but there is something thrilling that lingers for days after a great adventure. Hope to see you all with my date someday soon!

    • #723235
      Julie
      Lady

      I hope this is a okay answer. I was raised as a boy with really only wearing women’s clothes for fun and to be a old lady. Then when I did brief crossdressing in my 20’s then with doing female cosplays since my 20’s. Now last year for a bit of it doing crossdressing again but public this time from the start honey. Now this year since before today 3/7/2023 6:54 PM. I crossdress in public locally and online. I crossdress around everyone sweetie. I keep saying out loud what I announced on Facebook personal near end of Dec in 2022 while sick with random covid sister. I want to be a woman the beautiful woman Julie I see in the mirror! So once I’m her I’ll be truly happy again girlfriend! So did I think my current situation I’m in is where I’d be when growing up or after I grew up. Of course not doll. My parents raised me as a boy so I thought I had to be a boy hun. I also didn’t know and understand everything like I do now as an adult. So I know what I want now and I know you do have a choice of what gender you get to be sweetie. So I will be a woman for life! I hope all you lovely ladies love my truthful answer from the bottom of my heart dear.

    • #723247

      Hi ladies,

      Did I ever think I would be where I am today? The simple answer is no, but the dreams, the longings and wishing never went away, and now here I am, an older woman who has lived as one for almost a full year, looks 15 years younger than she is, and is legally a female.  All the wildest dreams from childhood on actually came true, and it is so wonderful, and feels so amazing, that I can’t find adequate words to describe it!

      Hugs,

      Ms. Lauren M

    • #723250

      i never dreamed i would be able to go out in public dressed as a woman.

      I worry that sooner rather than later i will never want to go out in male

      mode again and that would in effect end my marriage.

    • #723253
      Syndee
      Lady

      I can remember when I was caught by my sister growing up. I had “borrowed” a one piece swimsuit to wear and fell asleep in it. She came in to wake me up for school the next morning and lost her mind. She told my parents and it was off to therapy for me. They didn’t understand why I had taken my sister swimsuit or why I was wearing it. I spent about a year in therapy, reassuring my Mother and Step Father that it was just a one time thing. Years later I am married and find myself looking at my then wife’s underwear and wanting to try them on. That marriage ended sometime ago. I got remarried and for years was hiding who I was, I would go and buy myself panties to wear and throw them away, afraid my current wife would find them and leave. I finally got up the nerve to tell her and she was semi supportive of me. She had some rules she wanted followed and I agreed to them.  Now here I am, married to the same amazing woman. The rules are gone I wear what I want to wear. We go shopping together and have fashion shows at home when we are done. I get to truly be me, and she accepts me for that. Did I ever think I would be where I am today? Not in a million years, but I am happy that I have a supportive wife and good girl friends like the ones here that I can talk to about where I am and help me with my future.

    • #723269

      Hi Jennifer,

      The answer to your question is a resounding “YES”! It happened the second time I tried putting on my makeup, yes, the second time! I couldn’t believe it! The first time was a bad horror show and a sick joke, but the second time….. magic must have happened because I have no other answer. But it looked so good that I decided I needed to see how I looked fully dressed.

      When I was dressed and stepped in front of the mirror, I couldn’t believe my eyes. There she was. There was Jill standing there looking back at me, not Eric, but Jill. And as crazy as it sounds, I said out loud to my reflection, “It’s so nice to finally meet you, Jill.” I can’t describe the emotions, the confidence, the deep fulfilling happiness I felt at that moment, but I believe you already know what I mean. You’ve experienced it yourself.

      At last, I could see myself as a woman, not an overly pretty woman, but a passable woman and that was far more than I had thought possible. And it was that confidence that allowed me to finally go out in public for the first time three weeks ago. I’m still on an emotional high from that day!

      This was a great topic! Thank you.

      Hugs, Jill

      • This reply was modified 11 months ago by Jill Quinn.
      • #723292

        Thanks for your beautiful story.  I know exactly how you felt from my dressing last weekend.  You should post some pictures of Jill for us to meet.

        • #723296

          I’m actually considering adding pictures right now. And I’m glad you liked my story and more importantly, that you can relate!

    • #723311
      Patty Phose
      Duchess

      The first time I dressed fully femme and looked at myself in a mirror I was stunned and shocked at the girl looking back at me. She had, amazing sexy legs, beautiful breasts and such beautiful hair. It took my breath away. The pleasure and euphoria I felt was nothing I ever experienced before. I couldn’t keep my eyes off that girl in the mirror.

    • #723312
      Janet Woodham
      Duchess - Annual

      Hi Jennifer,

      I certainly experienced the same thing, it was actually when I posted my first photo on here.

    • #723329
      Diane Benson
      Baroness

      Hi Jennifer

      I am delighted that you your recent dressing session ended up being so magical. Having seen your recent photos I can see why you were so euphoric – no wonder you had trouble sleeping afterwards. I share your dream of looking like a real woman one day. My revelation came when I first saw myself after my a professional makeover and saw a rather attractive woman looking back at me in the mirror. The makeover showed me what is possible but unfortunately I don’t think I have come close to passing since. My makeup skills are steadily improving so I feel as though there is light at the end of the tunnel and that I will soon get there.

    • #723345
      Anonymous
      Lady

      Many years ago when I was still deep in the closet I could never imagine how things would be now. I live my dream every day dressing at home and under dressing in public and the wife knows which is amazing. Sometimes when I’m doing chores around the house while dressed I think about how far I’ve come and its almost unbelievable. I even go out in public dressed but not very often and wish I could do more. My wardrobe is many times larger than ever before and my feminine expression today is 1000% more than I could have ever thought. Life is good.

    • #723355

      I never thought I would be sitting here with my wife dressed in feminine lounge wear, including panties matching bra and satin robe All nice things she has bought for me. Never thought she would encourage me to get my ears pierced and give me wonderful earrings to wear.  for me a very manly man on the outside who wants to bring stephanie out it has been a great journey with a long way to go, but hard to believe I am here and so happy to be.

    • #723371

      No not in a million years would I have thought I’d be where I am today. Like most starting from a very young age with no where to turn to and now a crossdresser who has come out to many. The acceptance of myself, my wife being supportive and understanding, going out in public, wearing women’s clothes , perfume and makeup while still presenting as a man. Bra and panties daily. A huge leap from when I first started.

    • #723718
      Anonymous

      After what really amounted to years of practice with makeup and experimentation with different wigs, shareware and clothing, I did finally arrive at a point where I was close to, if not fully passable. I have some very good female friends who gave me guidance and encouragement along the way. Their advice made a huge difference.

    • #723722

      Where I started out young playing “dress-up”, with no wig and child feet too small for women’s heels; and growing up in the stereotypical “negative” age of what a transvestite was; the mid 70s to mid 80s, I still dreamed deep down that one day I might be able to go out in public dressed as a woman. Still, I never thought it would actually happen.

      Until in 2018; the perfect mixture of self acceptance, research, motivation, opportunity, determination, and fortunate luck; came together to make my dream a reality.

       

    • #723742
      AnnaBeth Black
      Duchess - Annual

      Jennifer

      Never did I ever think I would be where I am today.  I pale in comparison to some of the other girls but for me the fact that I recently came out to my wife and that I am even considering going out in public is huge. I couldn’t have ever thought that this might be possible. I’m so glad your pictures were all that you hoped for.

    • #723827

      Jennifer, I always dreamed but never truly thought I would be this far along with my Crossdressing. Some of my WOW moments are looking at myself in the mirror by a hotel elevator as I make my way to a restaurant dressed like a professional woman traveling for business or discussing with a sales associate what heels go with this dress or skirt and actually be taken seriously.                                                                                                                                      The most important wow moment is yet to come when I find the nerve to tell my lovely wife of 40 years Im a crossdresser.  Great topic thank you and by the way you look gorgeous I like your style.

      • #723843

        Thank you very much for your compliment on my photos, I really appreciate it.

    • #723877
      J J
      Lady

      No, I never thought I would end up where I am. I just started wearing panties, added bras and then other lingerie and eventually ended up fully dressed sitting in a restaurant enjoying a glass of wine. There was never any plan or desire, it just happened as my life strolled along.  I should have known when I got dressed up when I was about ten or eleven, but I pretty much forgot about that and just let my self do what I enjoyed. Kind of like the rest of my life, no real plan, I just followed where it took me.

    • #724399
      Caty Ryan
      Baroness

      As I oft state on this great site, I’d be one of the more, (ahem)  “mature” members on here. As such and looking back to my early  CD” “career”  ,with messing about in my mothers things in childhood and teenage years, we end up where I am today. Striving to be the “mature elegant lady”

      Starting up the “CD ladder” in my mid 20’s until where I am now, for me it was like the old company line, “our policy is one of constant improvement”.

      I was always on the conservative side, not much “bare flesh”, nor did I have the figure or desire for mini skirts or tight body con dresses.

      Naturally there have been highlights. EG the first time I ever was able to go braless with attachable breast forms, the first time I ever wore a bridal dress. (A LOONG time ago.) Thence fulfilling a CD life time ambition of owning/wearing a full on replica 17th century ball gown.

      Plus of course the many makeovers and “public outings” with last years femme bra fitting near the top of that list.(

      I could bang ona bit, but instead I’ll invite anyone who is interested to go to my articles and photos  on this wonderful site.

      Happy dressing

      Caty.

       

       

    • #724477

      Your photos look marvelous. Kiss.

      • #724483

        Thank you Kara, that is so nice of you to say that.  I love hearing it.

    • #725726
      Anonymous

      No I never thought It would go this far. I’m on the verge of going to a conference as a women and thought this would never be possible.

      I do rember when I had a similar moment as you. My first few times I dressed fully I thought I was a hot mess. I’m not sure why I even kept trying, I guess I just had the love for it. Once I tried makeup, I fell in love with the girl in the mirror. I thought there is no way that is me! My confidence went through the roof at that moment. I was so ready that I actually went out to a lgbtq bar that night, I just walked right in like I belonged and I haven’t looked back!

Viewing 31 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?