A
male
age
30-35,
anonymous
writes:Should I tell my girlfriend of nearly 8 years, soon to be married that I used to crossdress, and still wishes that I could?. I love my fiance very much, and I don't want to jeopardize my relationship in any way, but every day I wake up and think that something is not right. And then I realize I'm not going out on a Saturday in a nice dress, thong, bra, and a clutch bag, (oh and makeup). I really want to tell her but I don't want to lose her. she is the best thing in my life and i am so scared I might irreparably destroy what we have just because I want to feel pretty. Please help I don't know what to do.
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reader, anonymous, writes (20 December 2019): Why am I not surprised by this revelation?
Whatever you say my friend!
A
female
reader, Honeypie  +, writes (20 December 2019):
 Good for you! OP
And for the future, LEARN from this. HONESTY is important and so is trust. You both showed each other that you can be honest with each other and DO trust each other, so it's good - keep doing that but don't wait YEARS before confiding in her, ok?
Happy holidays, Merry Christmas
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A
reader, anonymous, writes (19 December 2019): This is verified as being by the original poster of the questionHi all, thank you to everyone that responded to my situation. Sorry, it has taken so long to reply, I just wanted to qualify something before I go any further. I have known my finance nearly all my life, we went to the same schools and live within 10 minutes from each other. so after saying that I took on board what you all said and I chose to come out!!!!!. To my surprise, she said she already knew. She has seen me in bars and clubs in my area dressed as a woman and she accepted me then. It turns out she was just as scared to tell me that she already new than me telling her!!. She fully embraces who I am and she even said it's a bit of a turn-on for her. Me and her are already planning new girls shopping and even talking about taking this to the bedroom. We are closer than ever and the marriage is still going ahead. We both told her parents and at first, they unsurprisingly shocked but said they accept it as long as she is happy. (My parents all ready new). I am so excited for the future thankyou again everyone telling me exactly what I needed to hear.
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reader, anonymous, writes (7 December 2019): Corrections:
"If your truth is, you need it in your life; then tell her now, and she can live her truth as well."
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reader, anonymous, writes (7 December 2019): Being a gay-man, I've made my choices; and considered how they affect the lives and feelings of others who love me. It's not all about me, and what I want. There are times I have to put others ahead of myself, because of how much I love them. I've also given-up things for my faith and love of God. I will never deny Him.
I'm scratching my head as to why you would jeopardize what you have now; when you've kept it under wraps for eight long years? You obviously want a heterosexual-marriage. A man and a woman. You've indicated that you "used to cross dress." I would assume you don't do that anymore. Why now that you want to get married???
Dear sir, women have to sacrifice much for the sake of love, and then for the sake of their children. While dealing with inequalities and double-standards society throws at them. They struggle with how society scrutinizes the female physique and appearance. If they are straight, want to get married, and have a family; they just want a straight-husband, and a happy marriage. With no cheating, scary surprises, or unusual sexual-fetishes.
Now you want to marry a presumably straight-woman, but dress like one too? You want to challenge her values and beliefs. You hid it because you know it is unlikely she wants that. You waited just long enough to be sure the choice would be a tough one for her to make. Now you want to emotionally-blackmail her; after she's in-love and has given you eight years of her life. "If you want to marry me, then you'll have to allow me to cross-dress too!" You don't have to say those words, the full implication speaks for itself!
Your love is unfairly conditional; therefore the choice is to accept cross-dressing, or be heartbroken! You will most likely deceive her; rather than be truthful. Insist on doing it secretly, after being told she preferred that you didn't. Leaving it all to chance that you might get caught, and she will really have no choice once bound in marriage! Why didn't you "come-out" as a crossdresser before you proposed to her? You put your own feelings and needs first. You are selfish!
My friend, don't do this to her!
What happened that caused you to stop cross-dressing? Why did you hide it? Why did you take eight years of her life, and decide you'll lay this on her now?
You could have told her at the very start, and all this would have been decided long ago. If she rejected you at the beginning, she would have had a chance to have moved on; and fallen in-love with someone she really knew. Not shaken to her very core with news hidden from her for eight years! I hate when gay or bisexual-men do this to women. I'm sure women feel exactly as I do about things like this! Anything that conflicts with their criteria, what they've been taught, and what they want and need in a man. Even gay-men have our set-limitations and criteria for other men whom we've chosen for our mates!
This isn't just your simple everyday run-of-the-mill hobby you're talking about! It leaves to question what your actual sexual-orientation is, and should children be brought into such a controversial environment? If she accepts it now, she might have second-thoughts sometime down the road. Seeing you in full-drag, just might be more than she can really deal with.
If she has already purchased a wedding gown, money has been spent in preparation for a wedding, the reception, wedding invitations sent, and her parents have no idea their future son-in-law like to wear bras and thongs; the humiliation and financial losses incurred could be unimaginable! Wedding-planners are not cheap! Nor are deposits and fees, catering, or other expenses for the ceremony!
Come on! It's not something that causes severe physical-withdrawal; or that if you don't do it, your ears will fall-off! You've done without it this long, just give it up for good. It's not a habit you can't give-up! If you truth is, you need it in your live; then tell her now, and she can live her truth as well.
I just can't see upsetting her with something like that, and risking everything; because you have some compulsion that you've supposedly given-up anyway. Now that you want to get married; you want to spring something on her that you know will seriously cause her angst and concern.
Is this all that you've hidden from her???
I don't think you should get married, unless the secret is disclosed. I think you should make a choice between cross-dressing; or a happy marriage, with her being the one who wears the pearls, makeup, dresses, pumps, with matching clutch bag.
It's better to lose her, than to force her to live an unhappy life for your sake.
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male
reader, anonymous, writes (6 December 2019): You need to tell her. Otherwise you are going to spend our life living in secrecy. Dressing in secret and then purging. Why love a lie if you love her and she loves you you should be able to reach some kind of agreement.
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female
reader, anonymous, writes (5 December 2019): If you feel this strongly about it then your partner really doesn't know you at all. She's marrying someone who is keeping a huge secret from her. And maybe when you tell her she won't care about the cross dressing but she will very likely care that you kept it a secret for eight years. Do it now. Do not wait to do it until after you're married. No one can guarantee that she will be ok with it, we dont' know her. But if she isn't, then it's something you need to know because it's going to bother you for the rest of your life.
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female
reader, anonymous, writes (5 December 2019): You need to be open with her. It’s not fair for you to keep this as a secret from her and if she finds out later down the line, which she inevitably will, she will be even more hurt. Marriages are about honesty.
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female
reader, KeW +, writes (5 December 2019):
 Hello,
Thank you for sharing. It’s brave of you to ask for help. It’s understandable that you’re scared of rejection. However, you need to be your true self with whomever you want to marry. That means telling them about your interests: including dressing up as a woman sometimes. Marriages are ruined by secrets, OP.
If this woman is the right one for you, she will accept you as you are - including your hobby. If she isn’t, you will break up and that is for the best because there ARE people out there who will love all of you - including when you dress up. You’ll most likely need to be with a bisexual partner, though - as they are open to men and women, and some will be attracted to you in male clothes and female clothes.
OP, you HAVE to be honest with anyone you love. There’s no happiness in being with someone who doesn’t know the real you and it will break her if you betray her trust in you by marrying her without telling her of this first. For most people, it’s a deal-breaker, but that doesn’t mean it’s wrong to do; just that you’ll need to find someone who embraces that part of you.
For someone to love you for who you are, you need to accept this side of you. This may mean the end of your relationship, but it means you can live honestly and enjoy your life fully. There are online communities for others who enjoy cross-dressing and they can help you accept yourself, then to find a partner who is happy with ALL of who you are.
Please do not marry someone while hiding secrets from them. It’s not fair to them, nor is it fair for you to hide who you are for the rest of your life.
Best wishes.
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A
female
reader, Honeypie +, writes (5 December 2019):
Let's say you were dating someone and then engaged to a person who wanted to "dress up and act as a guy, go to biker bars( or wherever) and do "whatever" as a guy" - wouldn't YOU want to know BEFORE getting married?
I think, in all honesty, that you OWE her the truth, if she can't accept that it is part of you then MAYBE she really isn't the best partner for you, because I can tell you this NOT telling her BEFORE you marry her and then all of a sudden AFTER the wedding spill the beans is UNFAIR.
Why have you not disclosed this a LONG time ago? 8 YEARS of being with her and you haven't thought to SHARE this?
Now I totally get the being scared she won't accept it, but HOW would you feel if the shoe was on the other foot? Wouldn't you feel bamboozled in to marrying someone you REALLY don't know as well as you thought?
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