Hello Girls, I got the biggest surprise on a recent vacation. A little over a year ago my girlfriend asked me to stop cross-dressing if I wanted to stay in a relationship with her. She had wanted this in our relationship and encouraged it for more than a year. I had been cross dressing in my own home privately for many years. I know being in a cross dressing relationship can be hard on the woman. She just couldn’t deal with it anymore. So I did a purge and decided I would rather be in a relationship with her.

We were on vacation last month at the beach. The nice part about going to the beach during that time of the year is the fact that the beach is not overly crowded in October and the weather is still really nice. So the first night there, we had gone out to eat and had gotten back from dinner rather early.

I was sitting out on the balcony of our condo drinking some bourbon when my girlfriend came out and she said, “Could you come in and help me with something?” So I walked into the bedroom she had some dress stockings and heels on the bed she asked me if I’d like to put them on. I just kind of looked at her. So I went ahead and got dressed for her in those items and we went out onto the balcony where we sat and finished a bottle of wine together. It just felt so nice being dressed again!

The next day we talked about it because she knows it makes me happy, however, she doesn’t know if she wants to let me do it full-time again.

The second day we were there, she painted my toenails and my fingernails She had brought a wig for me to on. We pretty much stayed in all that day and it was nice being seen as a woman again! She has told me when we are on vacation that I will be dressed as a girl all the time, she just doesn’t know if she wants me to bring it into the house again. She knows how happy it makes me feel. She loves me and I love her. It’s the first time she called me Sandra in over a year!

The rest of the vacation I was dressed every night in either a dress or some lingerie.

Please take time to send in comments to my article or answer one or more of the questions I’ve posted you below:

  • Have you gotten mixed messages from your wife or significant other pertaining to your thrill of cross dressing?
  • Are there certain limitations your wife or SO puts on your cross dressing which you find difficult to adhere to?
  • Has your wife or SO come forward positively with her acceptance of your cross dressing?

Thanks girls for reading my article and I look forward to reading your comments pertaining to my article or to any of the questions noted above!

Sincerely, Sondra





More Articles by Sondra

    View all articles by Sondra
    The following two tabs change content below.


    66 and kind of new to this. I wear panties every day now. Love my heel for sure.

    Latest posts by Sondra (see all)

    5 1 vote
    Article Rating
    Notify of
    Inline Feedbacks
    View all comments
    Susan North
    2 years ago

    Well, I first started to dress up in my mother’s lingerie when I was very young and fought with being a male and trying to suppress my inner voice to dress up and be a female. When I got married at a young age I always encouraged my wife to dress up sexy and show off her body and the things that she wore. This was ok till she found some of my own things and tried to understand. I suppressed my desire and it was a real fight and still is. Does she understand, not really! Does she support… Read more »

    Dani Grand
    Active Member
    2 years ago

    Good for you. And good for your girlfriend for adjusting, sharing her thoughts and feelings and even here suggesting you doll up on holiday and bringing the goods. For your questions… All messages these days are mixed. That’s on her as well as me. My desires for feminine display fluctuate – I think like all of us. How much I do depends on the ‘vibe’ I get. If the vibe is negative, I keep it low keyed or drab. In an indirect way, yes. For my SO, there are no greys, only black or white. Thus, I dress in a… Read more »

    Active Member
    2 years ago

    Thanks for sharing your experience. I have definitely experienced some mixed feelings from my wife over the past years. At first, she thought it was odd that I would dress as a female, but didn’t come to the point of telling/asking me not to. Then, for a while she was ok with it, even to the point of going shopping with me and allowing me to wear skirts around the house when she was home. Then it turned around again to “I just wish you would stop!” We are now at a don’t ask, don’t tell stage where she knows… Read more »

    Laurie Tidenow
    2 years ago

    Mixed messages and limitations OH YES! I’m 74 now and we met as 15-16 year olds. The Viet Nam war took us apart and 34 years later we remade the connection. As teenagers we experimented with her dressing me as I encourages her to. FF to 2002 I told her right off as she noticed I was wearing panties. I shipped some of Lauries things to the other coast so we could enjoy the two of us rekindling the idea of having someone completely accepting my crossdressing. The result was a sort of a purge as she encouraged me to… Read more »

    Lucinda Hawkns
    Trusted Member
    2 years ago

    wow what a vacation that was for you. yes i get 2 different waves of my wife with my cross dressing, she knows and tells me when i can dress up and she will not help me with make up, she has seen me getting dressed up, but will not let me sit in same room as her, she knows of all my female clothing, i have more then her and seem to wear them more then she does. i took over her dresses for she dont wear them any more and i fit into them just fine. she has… Read more »

    Cathy Ferguson
    1 year ago

    My wife is a little vague about where she stands with my dressing. She is 100% ok with me wearing skirts so I wear them everywhere, every day. Likewise underwear, all my “panties” are female, she is ok providing they aren’t overly frilly or floral. Tops too, as long as they have an androgynous look. Tights and pantyhose are ok, too. Ladies’ shoes, bras, makeup, dresses – all no-no’s. I love wearing dresses and heels, and do when she isn’t around, or if I’m away. It is my dream that she took positive action and led the way, or gave… Read more »

    Maria Heels
    1 year ago

    Hi Sondra! It sounds like she is trying to keep you happy and understanding your needs and for that, you must always respect her wishes. I have been dressing since I was a little child, never stopping, always in secret and through several years of a relationship and marriage to my wife. Of course, a year afterwards I got “caught” when she found some pictures and thankfully she didn’t freak out too much. On and off over the years, I’ve going through times of hiding and being out in the open…for several months it was go ahead and dress…where is… Read more »

    Active Member
    1 year ago
    Reply to  Maria Heels

    Everyone’s story is different and also the same in some ways. I am married 50 years and have accepted that my wife will never have anything to do with my femme side. I know if I had told my wife before we married she wouldn’t have married me. She knows 40 years. Balance is the keyword in my life.

    Celeste Starre
    Celeste Starre
    1 year ago
    • Have you gotten mixed messages from your wife or significant other pertaining to your thrill of cross dressing?

    Just once about 50 years ago. I told a woman about my dressing and she was very enthusiastic at first. Offered to share her clothes with me. Went shopping for sexy nighties that we both wore to bed etc etc. Then one day she came home and said that her minister told her I was an abomination in the eyes of the lord because I wore women’s clothing. Wasn’t long after that I showed her door and said bye.

    Michelle McQueen
    Michelle McQueen
    1 year ago

    Mixed messages? Yes. When I came out to the wife after 30+ years of being in the closet, she freaked then said she would help me buy clothes. For the next two years she went with me finding clothes and buying lingerie until out of the blue she said it just wasn’t her thing and she would no long shop with me or have anything to do with it. She has never seen me dressed and never wanted to either. That was about 5 years ago and now I enjoy limited dressing at home. I call it casual feminine. No… Read more »

    Rhonda Lee
    Active Member
    1 year ago

    I was drawn to women’s attire circa age 13… always felt guilty about it, tried to stop, and managed long stretches, thinking I was “cured”, so never said anything about it to my future wife. But urges came back ever stronger and I started hiding lingerie, which I’d take on trips. Ultimately she found my stash… thought I was seeing someone else. I eventually did a dumb thing and let her find me wearing an outfit she had put in the Goodwill bag. She just said “interesting”; neither of us dared talk of it. Then we hit a rocky patch… Read more »

    Would love your thoughts, please comment.x
    Subscribe To Our Newsletter

    Subscribe To Our Newsletter

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

    You have Successfully Subscribed!

    Log in with your credentials


    Forgot your details?

    Create Account

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