I told my fiance I crossdress and this happened…

Girlfriend supports my crossdressing

Hi. I’m Robin. I’ve been crossdressing off and on since my early teens and only recently have I come out about it to a few select friends. I’ve never fully understood my desire to be girly. Part of it, I think, is that women’s clothes always seem to be more vibrant and sexy than anything I’ve ever found in the men’s department. That and that I’ve never felt quite confident as a man.

One of those with whom I recently shared my secret with is my fiance. I was sure that it would be the end of things, yet felt she needed to know. Much to my surprise and delight, she likes this about me and has even begun helping me to perfect my look. While I still have a long way to go so as to be the woman I want to be, it is so much easier now that I’ve got such a warm and caring woman in my life to help me. I’m thinking that this site will also be of great help to me, so thank you for creating it.

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  1. Jc Brewer 10 months ago

    Well that’s great I done that an when we broke up she went around telling everyone she new then I meet my wife an yes she was told this about me but didn’t tell me well I told her she like I love it and starts telling me how wants me to do this and all.. She even has a friend that crossdress. She’s a cosmetologist so she knows slot of people. She said let’s all good out y’all dress up and we will go to Oklahoma City to a club so. We didn’t went well and she has several pictures of me dressed up. Well now if we get in the least bit of disagreement she always bringing up that she will blast my pictures in around town and all over facebook. So it real makes me never want to tell anyone or even act or be myself around her. It’s to point where if I thought I could leave her and that not happen I would. And I would move away find someone from start that wants to be with a crossdresser and just start off that way because it has really brought my wife and I to a stop I don’t want to be with her over this and from that point on I just never could act same or fill same or show her love. I don’t trust her as my wife anymore. Not as messing around but with my heart my fillings that trust I had when I done it in front of her that it’s gone

  2. Aeva Knight 11 months ago

    my girlfriend know i like to dress as a woman.
    she wants me to go to a casino dressed up, but i am more of a closet dresser. we drove to her friends house one time which is 40 miles from home. I was so embarrased driving down the road hoping that no one saw me with a dress on. (no wig or makeup on).
    when we got to her friends house i put the makeup and wig on and hurried to the house hoping no one recognized me as a man.
    her friend didnt even flinch about it, but I quickly changed back to my regular clothes.
    Somedsy i would like to get a professional make over and go out in public if i could be passable and get the courage to go out in public but it would have to be in another town far from my own.

  3. Laura 12 months ago

    My wife is very supportive and buys me knickers on occasions, but has never helped me with dressing which I would love her to do. She always complements me on how I look and the sex is great.

  4. philippa 1 year ago

    This reminds of a fancy dress party that my wife and l whent to. she wanted me to be the female part and taking great fun in getting my outfit from head to toe ,the evening before she asked me to try it on and the look of shook as I came back in the room.I think
    she thought I’d look like the ugly sister but someone total passable with no makeup and wig .
    Both of us had great evening at the party as we walked home on a crisp cold evening the thrill for me of cold air around my skirt and stockings and heels on the pavement, I had not felt that for such a long time.
    The next morning as I was making breakfast my wife came in and with newspaper in hand started talking about yesterday evening party ,and how all her girlfriends were saying it was not me dressed up she felt jealous and proud at the same time then she asked if I would wear female clothes again not just for a party ,I shared second before replying and said yes.A weird smile came across her face and said she wants to meet that person again so once a month l change into this person and her and i have a great time doing so .

    • Charr Shannon 1 year ago

      What a blessing to be able to share the most intimate desires and needs with your best friend!

    • Shandy Temple 8 months ago

      Absolutely love the story. Made me smile all over.
      Hugs
      Shandy

  5. cassandra 1 year ago

    hi I started out as cd and am now close the transition to woman hood would like to correspond with any TG,s for friendship ,I live in Australia Cassandra

  6. Veronica Raines 1 year ago

    Hey girl. Which one are you?

  7. Celine 1 year ago

    Congratulations.i also like it very much.even your fiance is supportive.our thoughts must always be optimistic and positive so everything will be fine and smooth.
    It is a great privilege for u.you should carry on.love u

  8. Tamera Lynn 1 year ago

    Congratulations on your decision, Robin . . . . . and a special congrat’s to your fiancee, for being so loving, understanding, and supportive. You’ve got the makings of a great life together. Love to you both, Tamera

  9. Tom tossen Vossen 1 year ago

    A female friend of mine said i should just be me amd do my normal non-cotton brief wearing in her presence.
    It made me feel free-er all around….so i did a little..and requested she show me the panties i want to see her in…
    ..

    .

  10. You are a very lucky lady I wish there was someone out there like that for me who would help me hone my inner woman

  11. Jennifer 1 year ago

    i think its great that you have a loving and caring woman that will help you i told my wife and she said it was gross and wanted me to stop . i still dress but i have to hide it from her

  12. Annieurok Wright 1 year ago

    While i am getting older, I am not as concerned as to others finding out. I live in the Springs down main-line 25. I have to ask, with 60 being 30 now, how does feel to real as you maybe

  13. Robert Rogers 1 year ago

    Am I Transsexual, Cross Dresser, or other. I am 73 year old male, closet dresser in Denver, Co. and would like to talk and or meet someone to help me to decide or if I am to old. Thank you.

    • Robert……You are too old now to go thru what is necessary to be transgender. You tube shows the operation in real time and it is fairly complicated. I would say…….cross dressing is best. now.

      Regards……….Lady Victoria Graunwolf.

    • Renee Johnson 1 year ago

      If it feels right go for ti Your never too old.

  14. Samantha Troup 1 year ago

    I so wish I had found that right woman to help me my first wife we were married 34 years she divorce me when I dressed for a costume party as a French maid now I was secretly dressing for many years but she used it as an excuse my 2nd wife I told about me dressing after we got married I was going to dress she stopped me said she thought I was kidding with her I will not go out with anyone who isn’t good with me crossdressering before we have a 2nd date

  15. Sarah Ann Shae 2 years ago

    Good for you sister! My wife knows and has lots of fun helping me….hope you two find lots of joy together!
    XOXO….Sarah Ann

  16. Lisa Sweetie 2 years ago

    Wow that’s fantastic I am married and I was lucky enough to share an evening with my wife in nylons but ever since she has not been too keen but I hope that one day she will be OK with me being Lisa x

  17. Desiree Ford 2 years ago

    She’s talking to US! She is talking to Man AND Desiree! OMG! I SO hope this is real! She really spoke to Dee AND MAN in the same conversation! I am “standing here beside myself”. This is unreal! I will be online with any certainty.

  18. Desiree Ford 2 years ago

    Lucky you. When I tried on a pink chemise that she had in her summer clothes tote the other day(just playing around didn’t really think about it ), her reaction blew me away! She looked excited! But, later when we went bed and I had it on she said “No!! Absolutely not”
    We were supposed to get mani-pedis today, but, that’s been cancelled. Can’t put the Genie back the bottle. I wonder where we go from here.

  19. Miichelle4 mallory 2 years ago

    My ex left me when she discovered that I loved dressing up as a girl I’ve been doing it for 40 years love being a sissy girl

  20. Miichelle4 mallory 2 years ago

    My ex loved to dress me up as a girl until she discovered that I loved it then she despised me

    • Samantha Troup 1 year ago

      Oh hun I know what that is like I’m saying from experience but like I said it isn’t going to happen ever again love samatha

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