50 something married bi crossdresser

I have worn ladies undies since i was 11 and had my first c*** at 13 now I'm 50 something married to a great woman. The issue is I still want to dress which I do. I wear panties and stockings to work every day under my work clothes. I dress fully when she or I am out of town. I also dress fully when I meet a man, I love s** with my wife but even more with men. I have tried to tell her but am afraid too. I brought up the subject early in our marriage but it did not go well so I dropped it. I still dress when ever I can. Can someone let me know if I should tell my wife and how they would?

May 7, 2019

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  • Do mot tell her

  • The cross dressing may be the easiest for her to accept. It is becoming more mainstream as time goes on. You know your wife...is she somewhat open minded, or does she have preconcieved notions that she's unwilling to change. The definition of love biblically is seeking what is best for the other person and not forcing your ideas upon them. You might try to bring up made up instances where you saw a man dressed up as a woman and get her to discuss that with you. That will give you some idea where her head is at. You might get her to accept your lingerie love, but getting her to accept you making love to a man, is a completely different subject. Unless she'll get into swinging, keep that a secret, and be diligent about hiding your tracks. H*** hath no fury like a woman scorned.

  • Oh, I wish I was there to hold you and tell you to continue your dressing desire. Don't tell any woman about this. They just don't understand that they aren't the only ones who can wear pretty things. Keep your secret and share it only with a like wise person. I bet you look cute all dressed up.

  • I think so, my panties and bras are far sexier then the wife's. I love to be as fem. as I can!

  • So do i

  • Thank you. I would love for you to hold me. What else would you like to do?
    I will have to keep secret since I do not want my wife to leave me. But I do desire a man's love and want to dress fem more hours of each day. if I was to tell her what do you think I should do or say to her?

  • You need to enjoy your love of women's clothes. Try to think of one thing that men wear that women can't. Ridiculous. Women have all the rights in the social world. It isn't fair or logical.

  • I agree with below, never do it.
    My mom was really supportive and used to buy my tights, girls leotard, nightie etc. Even from when I was about 8 I knew my feelings and actions of wearing womens clothes under my own or wearing them to bed was socially weird and kept it a secret.

    What I did not realise was that not all women were as open minded and chilled as my mom.

    So I told my wife. I think that planted the seed in her mind that I was faulty and had to be fixed. So even though when I realised she thought I was f***** up, I pulled back and stopped mentioning it and would secretly wear tights under my work pants and just did it in secret. Eventually she left me.

    So my advise is women say they want men to share their feeling but in reality they use it as an excuse to judge and condemn you.

    I still do not understand how my wife who proports to be a Christian and who goes to church and reads the bible can actually be so unforgiving, so judgemental, so vindictive and to build up such distain for me.

    In other areas of my life I seem to be OK. I get on with people. I play sport with mates. I enjoy my work colleagues. I think I am a pretty easy going person to be around. Once she dumped me I felt like crap but then I had a number of women proposition me. It was so nice to feel wanted. To feel human. But no way was I going to share my kink again. That is my secret.

  • Never do it. She can not understand your need.

  • This is not true. My husband dresses I help him with it. He has explained to me what it does for him and we embrace it. I even take him out, you just need to find the right person.

  • Can you tell me more about you two and his crossdressing?

  • He told me over 10 years ago I was young. took us a very long time to get to the point we are at. he tells me when he needs to release form life stresses and he steps into his other side. I help him with his wig makeup and I dress him, he enjoys when I pick out his outfits. we spend the time getting him all dressed up and then we usually go for a ride, picknick or out to dinner at a few select restaurants. he loves to wear satin pj's to bed and owns more panties than me which is fine by me! A man's package looks better in panties i think! we enjoy each other very much. I know for him it allows him to think and act differently. he is able to escape the stresses of one world and take a reprieve in another. I did go through all the typical mind questions does he love me? am I enough? is he going to leave me? After many trials tribulations and testing each other in every way possible. We have come out on the other side we are just very open and honest with one another in all aspects about life s** what he needs and what I need. We love our life and I'm sure we still have many more hurdles to go but h*** its been 16 years bring it on! He is an amazing man and I am the lucky one. I married a great guy plus I get a fun girlfriend too! Best of both worlds don't you think! that's our story if this can help someone great....wish you all the best!

  • That is great but all women don’t think and understand and process the way U do . I’m happy for u and him

  • Thank you for your input

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