A Wife's Crossdressing Success Story

This week I am truly honored to hear from Amy. This is the first time that a genetically born woman has shared her crossdressing success story on Crossdresser Heaven. Amy’s story is a blessing to all of us, and shows us that love’s embrace can strengthen even with – and sometimes because of –  crossdressing.

If you’d like to share you crossdressing success story, please take a moment to submit your story. I’d especially like to encourage wives and girlfriends of crossdressers to share their successes. Even if you’re still struggling with your loved one’s crossdressing your small successes will bring encouragement to many others who are walking the same journey.

Meet Amy

Hello, I’m Amy; I’m a 36-year old female who lives in a small town in Georgia.

Amy’s Crossdressing Success Story – A Wife’s Perspective

I don’t know if I can publish a story being a female, but I am so inspired by all of your stories that I had to tell mine. I met my husband about 5 years ago at a pizza restaurant where we both worked at the time. I had identified myself as a lesbian for 10 years, but hadn’t found the right woman. I had had two boyfriends, both of whom validated my reasons for choosing the lesbian lifestyle, even bearing a child from one of them.

But this one, 9 years younger than me, there was just something about him I couldn’t put my finger on, but I knew I had to have him. I heard was a preacher’s son and had a good reputation, unlike the last one who’d left me and my son 5 years earlier. Anyway, we hit it off and dated for 4 years before getting married. I always felt like he was more of a woman in bed, which naturally I liked, having been a lesbian before.

Now I had a kid, plus living in the Bible belt is not easy when you’re not living the “straight” and narrow, so I no longer had the desire to seek out a woman. So he was perfect, the best of both worlds. Little did I know just how perfect.

I knew he liked wearing my tank top I once put on him, but I thought it was no big deal since it never came up again. Later I found out that he was attracted to me from day one, having listened to my lesbian escapades. It seemed a part of him identified with/wanted to be one of those women. This might sound strange, but one night 3 years into our relationship, I heard in a dream or vision from a beautiful goddess (crazy, I know) telling me that I needed to tell him that it was ok to wear women’s clothes; that it was an ancient part of him that would be very healing if he would just allow it to happen.

I told him this, but he said nothing and I forgot about it. It wasn’t until our wedding night that I experienced the full extent of my husband’s desire to cross dress. We went and bought lingerie that I was hoping he would especially love on me. It seemed he cared more about himself wearing the clothes than me. I was actually jealous of a robe!

This was such a downer for me on our honeymoon. But how could I have known? We hadn’t been able to live together during our engagement, between his conservative background, and my not wanting to shack up only to be abandoned again. And he’s quite shy about such things.

Well, I am happy to say after nearly 2 years we have adjusted and grown together, and through a lot of communication and encouragement have created a beautiful relationship that is like no other. Thanks to Vanessa’s website, Vicki’s wise words for Christian Cross Dressers, and all the CD stories, I have come to understand why my husband feels the way he does; it even endears me to him more.

The stories have made me cry at times. One day I saw on Oprah a transgendered man (woman now) and her wife who would shop for jewelry together, and something about their story, their kinship made me cry as well. It wasn’t tears of sadness, but more of a cleansing and a relieving. It felt like, “Yes, that is it”, like a resounding truth.

Now I dress him up all the time. Occasionally he will put something on, but he is more passive and the thrill for him is someone else doing it to him. I no longer see his desire to wear women’s clothes as taking away from me. In fact, I think this has strengthened me to be more, to explore my masculine side, my dominating side (grin), and now I play video games with him and fix things around the house.

I’ve even explained to my 11 year old son that his step dad feels good in women’s clothes, and he was ok with that. He actually said it explained a lot and seemed relieved to now know the truth. (I’m sure he’s noticed him wearing my jeans and pj’s from time to time.)

My dream is for us to move to a place where he could be comfortable to be himself, be it in women’s clothes or makeup or even transitioning to transgendered. This whole experience has taught me that gender is a very complex thing and that we all have a varying degrees of masculinity and femininity in us.

It has taught me to question, what makes us a man or a woman? Doesn’t our Creator create us to express ourselves the way we want? Isn’t there a feminine aspect to our Creator that he/she wants to shine through us? What would the world be like if we were more free to express both male and female sides of us, or just one if that’s what gives us joy? I think it would be an infinitely better world.


The following two tabs change content below.
Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.

Latest posts by Vanessa Law (see all)

  1. Michael Behrle 1 year ago

    Hi my name is mike. I like the stories of crossdresserss. That the wife dresses them up ib cute stuff plus when they things to gethet they have them wear a silk head scarf and have it tied under the chin

  2. Sonya 1 year ago

    I myself have a wife who when found out about my crossdressing said she was willing to help me,but only on her terms.Her terms where all or nothing,so over time she has feminized me to the point where I be coke her sister.We go out every where as females and she has encouraged me to date men. She picks what I’m to wear each day, I’ve had to let my hear grow to where it is will over my shoulders and has been coloured a deep rich red with highlights.

    • Wendy 12 months ago

      I’m happy for you, how much things have changed since I got divorced back in 04.
      Most people I have known all of my life in the middle 50s in age 45 years ago was when I first put my mother’s bra and nylons on. Quick to aquire my own female clothing,around 12 after new friends moved in hot looking mom that shopped Frederick’s of Hollywood

  3. Tim Boyd 1 year ago

    I have been crossdressing for 40+ years sex with men and women too. Just feels so good

  4. Ginger 1 year ago

    My long term gf has known of my love of wearing pretty things.

    She fully accepts and encourages me to dress openly. I’m kinda shy living in Bible Belt.

    Last year I got a beautiful card with cash for Christmas. Sounds like an impersonal gift. However, there was a handwritten note included that said I was not to pay bills with the money. It is (was) to be used to buy pretty undies and things when She took me shopping.

    A little thing like that note meant so much. I knew she knew but I wasn’t sure if she fully accepted my love of dressing Or just put up with.

    The note and her eagerness to take me shopping assured me that my secret did not have to remain a secret.

    Since then we have shared many tender moments and shopping endeavors. My fem side is getting all it needs and she enjoys the experience.

  5. Michelle 2 years ago

    My wife was aware of my crossdressing when we married. She does not encourage me, or participate in any way. I keep my legs and body smooth shaven, and how I would enjoy my wife encouraging, even ordering me to wear sheer nylons on a regular basis. It would also be fun if she teased me about my crossdressing, calling me her feminine, ” husband bitch”, would be a real turn-on, as it would show a dominant side of her nature. I’ve had these feelings, and other fantasies since I’ve known her, but was never able to express them to her, as I didn’t feel she could be open-minded and accepting enough to include them in our relationship and marriage. Maybe too little, too late.

  6. Michelle 2 years ago

    I truly wish my wife would accept and encourage my feminine side, and at the very least encourage me to wear sheer nylons on a regular basis. In return for my crossdressing, I’d even accept and encourage her to see other men if this was something she desired and would enjoy. How I wish I could tell her about my kinky fantasies and fetishes. She’d just never accept and understand.

  7. Kate love 2 years ago

    My name is Kate and my wife has known for at least 15 of the 22 yrs together. I’m 41 and she is 37 we have 2 kids. She does NOT approve or understand and thinks I’m gay. She used to help but now seems disgusted by me even though I do not show any feminine side around her but she has started to make bad comments about mannerisms that are not any different than my whole life and are not feminine but I think she is just trying to use that as her way out even though it’s not around her or anyone. It’s good to hear not everyone is like that.

  8. Samantha 2 years ago

    I love these crossdressing stories. My wife knows that I love the feminine life more but really don’t want me to be Samantha like I want. We used to keep matching toenails, but now she doesn’t want to. It is sad to hide my female side.

  9. Wendy Tissy 2 years ago

    Well, here goes my story.
    I met my wife in Thailand some 14yrs ago this September, I couldn’t take my eyes off her when she was cooking in this restaurant that I went to often…to see her and the food was great too. I eventually talked her into coming for a meal with me, she’s a chef and didn’t see the point. We dated for a month while trying to speak to her with my phrase book and broken Thai that I’d learnt over my time there..

    She was losing her job and I asked if she wanted to join me on the island of Samui, she asked her mother (she was 26, that’s Thailand for you!!) she agreed and I said that if we stayed together and got on well then I would set her up in a restaurant of her own. Her family did the copy of my passport thing, sensible of them. Then we made our way to the island. We’d been together for about 6mths and we really got on well. A friend asked me after tasting my wife’s food if we wanted to take over running the restaurant part of his beach bar & restaurant, we jumped at the chance. I knew if things were going to progress between us that I had to come clean about me being a TV, possibly a TG person!

    She looked at me and asked if I was gay, I said no, she said…OK then! I then asked if she would go out with me to get some clothes, a dress, knickers, bras, shoes etc…she agreed but seemed concerned…I went back for my father’s funeral in 04′ and on my return brought her some rubber fetish clothes and a expensive corset…she loved them along with the magazines too…I was overjoyed..

    After enjoying ourselves with the new clothes she didn’t seem to want to play with my way of life and only seemed to want me to be a man….I was troubled that she was only with me for the security, even though we got on so well it was untrue, even with language and cultural differences….Anyhoo, after being together for 4yrs we got married even though things weren’t really how I’d hoped they would be as I stressed that she really had to accept me for who I am or the relationship wouldn’t work, as I can’t change myself that much, or want to.

    ‘We’ got pregnant and lost our 1st baby, then we got pregnant again and have the most amazing little lady I have ever known (not being biased, she’s incredibly clever and super gorgeous!) I was missing dressing up and the markets that came to our area arrived again and we went there one evening. I saw some knickers and bras that would fit me and asked if she would get me some..She held up the bra to my chest in front of the Thai woman who never batted an eye and then picked out some knickers too…gave them to the woman and said he will wear them later….I was a bit embarrassed and thought that it might be a punishment and that problems may ensue later…
    To my surprise she was true to her word and once we got home she told me to go and put them on. Our daughter was very young then and went to sleep. My wife came upstairs and giggled then adjusted my bra for a better fit and said to my amazement…That’s better…I now have a few very nice bras and lots of knickers…I have a dress but need a new one as it’s getting old now…

    Then, about 18mths ago she told me that she had a confession to make! I thought the worst, but yet again I was wrong…She told me that she wanted me to dress like a baby gurl for her…she said she didn’t want to tell me for years & years! I didn’t know what to think and said that I’d try it…she wanted me to wear a diaper too!! I wasn’t so keen on that but thought that she’d accepted my womanly side so I owed it to her…We then went on some websites and I found these cute little baby doll dresses etc and Lolita clothes, she said that she loved them too…I thought she meant that she wanted them for me to wear, but what she really meant was that she wanted us both to be little gurls together….I was flabbergasted….we’ve been experimenting now for about a year and things have really exploded in our life, we laugh loads at each other and she loves that I have accepted her quirk too…

    I am still a bit…well…freaked…..But, I get to wear gorgeous little numbers that are more gurly than baby..my manipulation techniques I suppose….
    I have satin and silk things and get to wear lots more than I ever dreamed of…it’s still a bit odd to me, but she’s super happy and keeps asking me if I am OK with her fetish… I feel more secure than I ever did in our relationship and she’s getting kinkier than ever….Which is very nice…

    Wow, that was long and I have never, ever told anyone this ever before!! So, I am trusting you ladies a lot not to judge and rip the piss out of me…LOL…

    I do hope you don’t find me weird or anything….I just love to be able to wear cute female clothes, socks, knickers, and shoes…I even get to wear high heeled pumps…I am not sure how that fits into the baby thing for her….or the make up that I love to wear…but as I like a subtle look (in baby style clothes!! But, not all the time I hasten to add!!…I do get to be a woman a lot too!!)

    So, that’s the kitty kat out of the bag….what do you all think?! Are we odd or what?!

    Hope that everyone doesn’t think I am a freak or anything, but I do like the way she and the dressing up makes me feel…I relax and we have fun…

    Tissy. <3

    • Wendy Tissy 2 years ago

      She has even bought me hormones and gotten our Trans friend to speak to the doctor for me and he will give me check ups after a short while…she said she wants me to be more feminine and she’s always having dreams to being with another women, she says that it’s me!! She says she wants me to grow little breasts and have a more female physique…I was so happy when she said that, but I am worried that our daughter will notice…till she found my clothes, as I am working away. My wife just said matter of frankly that ‘Daddy has to wear ladies clothes as his don’t fit him so well’!! LOL I only took the hormones for a month so don’t be too concerned yet ladies and they are a every low dose…I will see what the doctor says once I get back in about a month..If she wants me to go further…

  10. Zeta 2 years ago

    Once all our children had left home I began again to explore the pleasure of wearing women’s ( and pretty men’s a la Xdress and La Mystere) clothes. My wife (now married over 50 years) was OK with it, and in fact joined in erotic play while i was in lingerie.

    I was still subject to the shame and purging that most of us have felt and it was this, my getting rid of women’s clothing i spent a lot of money on, that I think made her less enthusiastic.

    Now I’m near 80, have girly babydolls to wear to bed along with some less feminine and fussy that she has made me, skirts she has kindly lent me and slacks and shirts that zip and button from the left, and Victoria’s Secret panties.

    No more erotic games, but her generous acceptance is more than enough.

  11. Paula Hayes 2 years ago

    I love the stories, I’ve heard many . Everyone is so different, & everyone has a different outlook . I’m on my own now so I only have my self to please. I don’t like the word cross dress , I’ve worn female clothes for 44 years now on and off. I’ve had 2 marrages , both ended , but neither for being fem, I’ve been out fully for 5 years now , but even now confused why , but so happy .

  12. Kristi2613 2 years ago

    This is a good post…my ex and I explored role reversal…I dressed in womens clothes since i was 8…but when she brought this to me I was accepting. It played along for years as she would have me try on dresses she bought. She was irritated I know from things she bought that looked better on me than her. I remember a night we going to dinner and she was mad cause she did not have any hose…I reached into my wardrobe and gave her a new pair…she refused to use them…I think it really distresses a woman sometimes to know the man they married looks better than they do. It’s a twisted knot. Now many years later she is sending me Avon books in good way. It’s a strange world. Today I am living on my own and do what I want…and that is to not fall to everyone’s wishes. Makes me happy!

  13. MiMi Pope 2 years ago

    Hi Amy,

    I’m MiMi & a Cross Dresser.

    I Thank you so much for the story you have shared with us all.

    I tell everyone now a days that I am a Cross Dresser but had lost faith that I would find a female that would except this about me.

    Your story has resparked the faith with in me that their could be a female out their for me that would expect me & Dress me up too.

    Sure I figure their could be a man out their to but that was only because I figured I would find no female that would marry or at least date a man like me.

    Thank You so much for sharing.

    MiMi Have a Blessed New Years.

  14. Kadie 2 years ago

    I have been a CD my entire life. I made it open early in my marriage. At first she accepted my feminine quirks. My wife would by me undergarments, she would sew outfits for me. But after a period of time, it became a conflict. She refused to partake in any feminine time. She would be hateful if I dressed once in awhile. She definitely despised me, when I would shave my legs in the winter. There was no sexual play, for she stated if she wanted to be with a woman she, she would have found her one.
    After a divorce and then reuniting, she knows I never gave up my feminine side. But My female persona is upstairs, and comes out when she is not home.

  15. Victoria P 3 years ago

    In my past I have met 5 women who were great with my crossdressing,however these words may upset a few of you. I have also met other CD/TG who wives have eventually had enough.
    My recent breakup only a month ago with my gf or nearly 6 years was just amazing with it all.
    In the last few months she found she disliked Caitlyn Jenner and thought I was also TS which I am not but I thought I may be TG…? some counsellors think I may be,but nothing 100% evidence wise just yet.

    So anyway she gave up on me completely becoming revolted by it all. Sure we had one or two other problems BUT ever since I went out in pulbic to mseet another ‘sister’ at a coffee shop ,she was freaked right out.That did it for her,but she never told me how it affected her so badly,I am 100% loyal and stupid me always has been but I did nothing but go for a little chat and a nice coffee.

    Now we are split and thought trying to be friends she;s already on a dating site which increase my pain and anxiety.

    Advice do NOT tell your wife or GF that you dress if you want a relationship to last because divorce statistics show that CDing RUINS marriage and relationships.
    She may accept at first BUT most women’s acceptance has an EXPIRY DATE.

    Good Luck to you all though

    I shall NEVER tell another woman as long as I live

  16. Ashley Lim 3 years ago

    The first time my wife knew about my crossdressing was almost 15 years ago when she saw my photographs and she does not really like it or gave her support, maybe she is an old fashion lady who think that men should be macho. Since now I kept the secret away from her. Usually I go outstation twice yearly to meet up in a special gathering with my CD and Tg friends. I am very happy when we meet up occasionally. Now I am quite frustrated that
    I cannot go further than just secretly Crossdressing out once in a while when she is not in the house. Sometimes I feel that my life as a female is gone because now I am 68 years old.

  17. Sunshine 3 years ago

    I have only recently opened up to my wife about crossdressing. She has astounded me at her openmindness. Just to day we raided her clothing to see what Looked good on me. She is so amazing about everything shes given me panties, and i love the way she grins when she slides them off of me. For us my exploration into crossdressing started with my disire for pegging. Living in the bible belt(even in todays times) you were always straight or gay but with my wife i have found out i belong somwhere in the middle. When i dress i see myself as my wifes gf. The awsome part is ive never told her that yet she told me that its like i become her new gf, now i dont know if this is why ive only dated bi girls before but with my wife it has made this alot more fun. She dose my make up and tells me how pretty i am and i just eat it up. Now i know this is all new and could change and it scares me to death, but for now at least she is very much apart of my girlish side and takes

    • Sunshine 3 years ago

      Part in every aspect. On top of all this our sex life has exploded and she is helping me learn about this side of myself as she dose the same. Now i dont always feel that side of me and she can now tell what mood im in and i can tell sorta what her desires are and in the bed we play it by ear. Ive felt these feelings most of my life relating to the old joke a lesbian trapped in a mans body one day the next the hippy king of the streets. Though i never let myself think on them. My wife has been the most engouraging person on this side of things. She has even planed away for me to feel comfortable in public at first. Emily your both my bi-sexal love goddess and the queen of my castle i would have never explored this side of me with out you. No matter what clothing i wear or who i feel like you are the most beautiful sexy adorable wife i could ever ask for. As atractive as you are brilant, and as funny as you are execpting.

  18. Janet 3 years ago

    I would love to meet a woman like Amy. I’ve always dreamed of being with a woman who preferred me as a woman also. My Ex started dressing me for fun but I became so obsessed with becoming a woman she started to back away. She said I enjoyed being the woman in bed too much for her liking. I would do my nails and wear pretty lipstick for her. She finally said that I’d become too much of a woman and we divorced. I still dress but would love a lesbian relationship with a Genetic woman who appreciates me for the woman I’ve become.


  19. Vanna 3 years ago

    She finally kissed my lipsticked lips, it was hers after all. Asked me to finish vacuuming then neatly put the dress back in her closet, but “keep the shoes…you ruined them for me” and that was that. She didn’t like it when she saw me in her clothes. We stayed together another 3 years, but nothing was the same.

  20. Vanna 3 years ago

    I know that feeling, Michelle. I was married to a woman who encouraged me to wear her sexier clothes… But only when she was out of town. I had my own panties and bras, but she told me where her silicone breasts were so I could fill out the dresses. Her 2″ heels and 5″ heels fit me, so you know which ones I wore. Those stiletto pumps were the best. Until she came home early while I was vacuuming and she just stared… Waited for me to notice her (my heart stopped and raced when I saw her because I was scared and excited) then she smirked and said “are those MY shoes?!” I was stunned. I hurried to her bedroom before she could close the door to tell her I’d get her another pair, but she just sat at her dresser and asked what being dressed like “that” did for me. I tried to get her to look at me… Really look at me. The same man she married, same man she gave thongs to, same man she told to wear what I had on. She just couldn’t stand to see it.

    • Vanessa Law 3 years ago

      I’m sorry hon, that’s a hard surprise for you and her.

Leave a reply

Your email address will not be published. Required fields are marked *


People Who viewed ThisX

People Who Like Thisx


Log in with your credentials


Forgot your details?

Create Account