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Thread: Dating advice

  1. #1
    Junior Member Aubrey Skye's Avatar
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    Dating advice

    So, I know a lot of us usually just start the dating process and even marry, before ever bringing up anything about our other side. I was wondering if anyone here has been straight forward with the person very early in the relationship? I feel bad about hiding things and I feel like it should be something they know pretty early. That may not be the best approach though. For those with success, how did you go about this predicament of telling the person you were dating? How did you bring it up?

  2. #2
    Ice queen Lorileah's Avatar
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    When my GF was coming out to meet me from Cali I sent her photos BEFORE so she could change her mind if she wanted. She didn't and she actually liked the idea. We spent 15 years dating and went out together often
    The earth is the mother of all people and all people should have equal rights upon it.
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    Nez Perce



    “Love isn't a state of perfect caring. It is an active noun like struggle. To love someone is to strive to accept that person exactly the way he or she is, right here and now.” - Fred Rogers,

  3. #3
    Senior Member UNDERDRESSER's Avatar
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    There have been many threads about this.

    I told my SO before we actually started "dating" as such. Why?

    1. I felt it was going to be serious, I didn't want to be dishonest out of the gate.
    2. I was virtually certain she wouldn't out me, pretty certain that it wouldn't impact our friendship, somewhat confident that she would be OK with it.
    3. Very knowledgeable, smart, and perceptive woman, didn't think I could keep it a secret.

    As of now, I don't consider myself a CD, though I am by most definitions, I don't try to mimic a female body, but i wear female clothes that work for me. Mostly skirts, underwear and hosiery.
    "Normal is what you get when you average out the weirdness that everybody has." Quote from my SO

    Normal is a setting on a washing machine, or another word for average.

    The fact that I wear a skirt as a male should not be taken as a comment on what you do, or do not wear, or how you wear it.

  4. #4
    Rachel Rachelakld's Avatar
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    For same reasons as the others.
    Girls always find "hidden stuff" eventually, so when you figure this is the girl for you, then it's time to share yourself with her.
    Much better now than once you have 3 kids, mortgage etc and she views the marriage as a lie.

    For me, after I cooked a lovely meal for us, had a glass or two of wine, I moved the talk around to womens fashion and mentioned I enjoyed wearing womens clothes. She was a little stunned so I then invited her to have a look at my collection (which was at the time quite classy dresses & skirts and 1 wig). I asked her if she wanted to try any on, she said yes, had fun with the wig and after a few changes we realized we were both naked at the same time
    We have been married about 5 years now and loving every minute
    See all my photos, read many stories of my outings and my early days at
    http://rachelsauckland.blogspot.co.nz

  5. #5
    Senior Member MissTee's Avatar
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    If you can see yourself getting into a serious relationship with this person, then yes. Share early. Otherwise, until you know, it might be a waste of confidence.

  6. #6
    Aspiring Member LelaK's Avatar
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    I told a woman on a dating site whom I was messaging for a while that I crossdress. She said now she knows my secret and she blew me off, but not because of dressing. So in my last message I said, I sometimes wear women's pants that are indistinguishable from men's. That way I felt like she didn't have anything over on me and I didn't mention that I also wear dresses etc.
    T-shirt says: "Hi, I Crossdress!"

  7. #7
    Senior Member
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    The contrast in this thread is telling someone you know vs not knowing well.
    Also the individual girl made their choice. That says it all. Advice is great but
    the real choice is personal.
    Char

  8. #8
    Adventuress Kate Simmons's Avatar
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    I told her before we go any further, there is something you should know. She had never personally known anyone that CD'd and she said so what?
    Second star to the right and straight on till morning

  9. #9
    Platinum Blonde member Ressie's Avatar
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    Once the date becomes steady and more serious I always tell. There's always the risk that the GF will freak and tell all of her friends, but that could happen at any stage of the relationship. If you wait too long, you may never fess up.

    Now days, I think it's a good idea to find out how a woman feels about CDing before admitting to it. Of course, I'm single at this point of my life, so take this advice with a grain of salt!
    "You're the only one to see the changes you take yourself through", Stevie Wonder

  10. #10
    Junior Member flogo920's Avatar
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    My wife of 34 years knew about my having breasts at the gate, and within weeks of meeting I took her to the Queen Mary in LA to see the female impersonators. She commented how they look better than most women. I explained my bra and CD fetishes (right word ?) but as I explained that that was for her ears only.

    One X-mas she bought me "Girlfriend,Men, Women and Drag". We have had discussions. With the increase in our job intensities (surgeon and RN) and with the arrival of kids, one after 8 years of infertility one after 2.6 years of paperwork, a lot of $$ and a trip to Siberia CD ing took a distant back seat to our attendant responsibilities- between job and kids our really dream love affair went on an autopilot, but lost its intensity,

    Since there is nearly no time to breathe ( she's of to work, and with her evening class I will not see her again till 10- PM), CD ing has no longer been a topic of conversation, but I assume no interest on her part as she is also buried in activities she cannot delegate. It has become non-issue. I still partially dress in the solo privacy of my office when I have disagreeable paperwork to do, but that's all.

  11. #11
    Platinum Member Beverley Sims's Avatar
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    My reputation preceded me and most who dated already knew.

    Those that didn't were sucked into the fun of it and there was never any disappointment.
    Work on your elegance,
    and beauty will follow.

  12. #12
    Aspiring Member
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    It's been so long I can't remember but my wife and I have been together since 1987. Today I have every liberty possible with CD'ing or beyond. It started around our third date when we were getting serious about each other. I remember saying something like, "What do you think about _________?" "Because I like to occasionally wear panties and even a nightgown to bed."

    I waited for the bomb to drop and it didn't. Instead we talked more and I took it very s-l-o-w-l-y to say more and wait for her acceptance. Eventually she began to surpirse me with things after shopping. But I did take everything slow to allow her to adapt. I also probably overcompensated by bringing other qualities to our relationship to have her feel very secure being with me.

    Today it's all second nature for us.

    Bottom line is absolute honesty upfront and don't try to hide anything that destroys trust. It'll be a do-or-die experience. There are always more partners who would be great with you if another rejects this side of you. My parachute opened quite well! LOL!

    Cheryl
    Last edited by Cheryl Ann Owens; 09-30-2014 at 12:03 PM.

  13. #13
    Gold Member bridget thronton's Avatar
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    I think it depends on how soon you understand and know yourself as well as how sure the relationship will move past casual outings together

  14. #14
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    I told my wife on our 2nd date. I always knew I would not stop so I thought it only fair to both of us.

  15. #15
    Female Illusionist! docrobbysherry's Avatar
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    Exclamation I would suggest that it be on a "need to know" basis with dates and everyone.

    Tell her: If u suspect you're trans, you'll want tell your dates ASAP.

    Don't tell: If you're a closet CD. Wait until your relationship appears to be getting serious.

    Somewhere in between those 2 or farther down the Yellow Brick road? It's your call----
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  16. #16
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    After my last relationship ended for unrelated reasons, I had basically decided I was going to stop the CD part of my life because other things were more important to me. Bored/Drunk/I dont know what one night, I made a profile on a dating site that no one I knew was on where I flat out stated that I was a straight CD'er. A few months went my and it got a hit and I've been with the girl since. I'm glad things worked out the way they did, because even with me trying to stop cd'ing, I know I would eventually end up sneaking into a gf's closet. Find a way to be open from the start or very close to it. If this is a part of you, you need to accept that and make decisions based on the assumption it's not going away.

    I'd say treat it like any other sexual fetish(I know its not for a lot of people, but bear with me) timing wise. It's part of what makes you happy. Whenever you would normally tell her what your into would be when I would break the ice on the issue.
    Last edited by latex-steph; 09-30-2014 at 06:19 PM.

  17. #17
    Junior Member atlflygirl's Avatar
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    I am still very hesitant to say I crossdress since I'm gay, and most gay men want a masculine guy to date. They're much more stuck on that than women, in my opinion. The risk, I believe, is that they'll think I'm a potential transsexual since we as gay men aren't that far off brain-wise. While that is fine in my book, it's incredibly competitive to attract handsome gay men, so my crossdressing once in a while is something I don't automatically share. My interest in leather, however, is VERY important to me and I just about require that a potential suitor is open to wearing gear, going to seedy bars and fetish play. Definitely limits my choices.

  18. #18
    Gold Member Alice Torn's Avatar
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    I have told every woman i was interested in, the last several years, and each time, it turned them off, and was a deal breaker.

  19. #19
    Aspiring Member Steph_CD_62's Avatar
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    When I started dating my current wife I knew I didn't want to hide anything from her, and for her to be surprised later. I met her online, and had several conversations over the phone after we realized we lived near each other. I had told her over the phone my love for lingerie, but nothing else. When we finally met I knew she was the one for me and I didn't want to hide who I was. I knew if we were meant to be together I had to tell her early in our budding relationship. I told her within a week of meeting her face to face. She was a little shocked, but didn't say a lot. I explained as best as I could about who I was and where I was going with my dressing. We didn't talk for a couple days after that, and I didn't pressure her either. When we talked again she had questions and I answered all of them. That was 13 years ago and we are still together. She supports me although I know she wishes I would quit dressing, but she also loves me for who I am and doesn't really expect me to change either.

  20. #20
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    Every woman I have been in a relationship with, or even there was a possibility of such, knew about me. I met Old Lady though a mutual trans friend, so she knew before she even talked to me... and that was great, while it lasted...

    That might by why I am so lonely... but at least I am honest and upfront every time. Sadly, that doesn't keep me warm at night... alas.

  21. #21
    Luv doing girl stuff CherylFlint's Avatar
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    I put an ad in “LOVE AOL” and said that I was a CD, and the usual other stuff. I received a response from a girl the next town over and we met at a restaurant. We hit it off and she asked me to come over to her apartment that weekend and “dress” for her to see how she could handle it, which I did, and she had no problem.
    About a year later we were married.
    Matter of fact, she took complete charge immediately and would help me with my makeup and so forth.
    We went to a wig store and she picked-out a number of different wigs, and then she asked the SA to put them on me so she could choose which one she liked the best. She bought me a wig that day. I’ve wondered what the SA thought.
    When she wants me to dress she’ll just say, “Go get dressed”, and I’ll go into the 2nd bedroom and there she’ll have laid-out the outfit she wants me to wear, sometimes including the jewelry and, sometimes even the bra.
    My wife doesn’t even own a slip: I have many. My wife doesn’t own anything “see through” while most of blouses, skirts and dresses are see-through or almost. My wife always wears pantyhose while I always wear ff seamed nylons.
    I’m more girly than my wife is.
    NEXT DAY ADDITION: The reason why my wife makes the effort for me to "pass" is that, and I asked her once, that she'd rather be with and be looking at a nicely dressed girl than a sloppy CD.
    We're to the point that she'll say, "Get dressed" and she'll have laid-out slacks or jeans and a regular girl shirt and we'll walk the dog together.
    It's possible to have a good life as a CD with a woman but you've got to be up front about it.
    My ad was on AOL for two years before I hit the jackpot. Most of the hits were of the "I didn't know what a CD was" type of response. Or "I didn't read the part about 'crossdressing'". Lame, so true. Be, nevertheless, true.
    Many women who've I've come in contact with on the internet have expressed, "I wish there were more men out there who liked to dress".
    Keep searching, and if the one your dating freaks-out about it, don't worry. Keep looking, you'll hit the jackpot sometime, it just may not happen overnight.
    We have no problem with how the relationship works.
    When we go out it’s just like two girls together. In stores or restaurants she does all of the talking.
    We’ve been married for over 10 years and it works just fine. She’s the boss and I like it.
    So my advice? Tell her straight off. If she has a problem, that’s her fault, not yours. There are girls out there who like CD’s, and for proof, I married one.
    Many a time my wife will instruct me to wear my wig, bra, garter belt and stockings to bed. Works for me.
    Good luck.
    Last edited by CherylFlint; 10-01-2014 at 12:17 PM.

  22. #22
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    I told my wife about 3 months into dating, the relationship was getting serious enough that I felt I needed to get it out there before it went too far. I dated a lot of women before I married, but only told 3, usually at roughly the same point in the relationship.

  23. #23
    Ms D'Meener Cally's Avatar
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    I made the mistake of not telling my first wife until 12 years into our marriage and WOW, was that the wrong thing to do.
    She felt trapped and resentful that she did not know all the facts at the time we were married and that colored the relationship for ever after.
    We divorced about 10 painful and lonely years later.
    From that point on I vowed to disclose as soon as I thought the relationship was serious and found to my surprise that the women I told were actually appreciative and supportive.None went screaming off into the distance.
    It was so good to get the Genie out of the bottle early and be able to then see if the person I was dating was actually compatible on other levels. God knows I had a few disastrous relationships still, but at least I know they were not down to CD'ing.
    Basically, keeping secrets is not a good basis for a strong and lasting relationship.
    I persevered and have found a wonderful woman and we married earlier this year. She is completely supportive and I love her dearly.
    So my advice is - "If things are looking serious when relationships are starting out, be honest and respectful. If it doesn't pan out, well it wasn't meant to be. It's not as though there is not someone else out there who will understand and love you as you are - but they need to know who you are before they commit."

  24. #24
    AKA Lexi sometimes_miss's Avatar
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    Quote Originally Posted by LelaK View Post
    I told a woman on a dating site whom I was messaging for a while that I crossdress. She said now she knows my secret and she blew me off, but not because of dressing.
    See, that's also part of the problem. Lots of women might feel guilty about being politically incorrect about being uncomfortable with crossdressing, so they deny it's really the problem, and use some other reason for the split. At least, that's how it worked in my divorce. Turned out she could have dealt with almost anything else, but the crossdressing was the true reason. And this seems to be quite true; lots of women stay with men who lie to them, cheat on them, beat them, steal from them, etc., but they stay with the guy because they still have that attraction to him But screw up the sexual attraction, and all bets are off, because she'll always feel the urge and will just replace her desire for you, with the desire for another, more masculine male.
    That said, I carefully mention transgender things and see how the woman responds. I have yet to find a woman who finds crossdressing an attractive trait in a man. So, good luck, Aubrey. You'll need it.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  25. #25
    Silver Member Stephanie Julianna's Avatar
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    There is no easy way. You just have to preface the talk with, "I love you so much that I have to tell you about......" If it is really true love she will stay with you. That does not mean she will want to be a part of it. That's when some serious compromising will come and some soul searching on both your parts is needed.

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