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Thread: BF dropping hints: should I ask him?

  1. #26
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    i think you should go ahead and ask him. it sounds like you are supportive, so i would let him know that if you bring it up. it may help ease the tension a little. also, maybe a more serious approach would be effective. he may have thought you were trying to make fun of him when you were lightheartedly joking about things before.

  2. #27
    Senior Member Sally2005's Avatar
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    If you ask him directly, it might feel like you are accusing him of something and he might clam up. There are many forms CDing takes and it is a personal experience for many. I think you should talk to him, but do it in general terms and from your point of view. Tell him what you like about CDers and what concerns you have. If you are open and supporting, I think he may open up after some time and talk to you. One other way to do it, is just grab him and tell him you are going to give him a makeover... and fully transform him and see where it goes...

  3. #28
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    It sounds like he's very shy and sensitive about his habit and possibly could have even been hurt in the past.

    First....you should know what you are getting into. You are in the correct place for that, and are a great lady for reaching out for help. IMO the worst thing that can happen is that you tell him that you are completely accepting and then start to put restrictions on his dressing over time.

    If you are truly willing to accept what this may involve (and where it could lead) I would ease into it by giving hints that you are accepting and that you understand what is (or may be) involved. Acceptance and encouragement will go along way to him coming out to you. You need to make him feel completely comfortable about talking to you about dressing and/or his feminine side.

  4. #29
    Luv doing girl stuff CherylFlint's Avatar
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    Been there, done that. Go ahead and ask him, but don't share. Yours are yours, and hers are hers, understand? Good idea to set the groundrules from the get go, if there is one.

  5. #30
    Member Georgia Rose's Avatar
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    Some guys don't know how lucky there are. But there could be a lot of hurt in the past. Somehow you need to encourage him to talk. Maybe make a big deal of how much you would enjoy having a manicure/pedicure with him (or something similar) and get him to do it for you rather you doing it for him.

  6. #31
    Member AlisonRenee's Avatar
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    Tasha,

    Your SO is really lucky to have a girl so willing to accept this side of him. I've walked in the same shoes he's in so I really understand what he fears -- which is revealing something he's probably hidden all of his life, being "outed" and subject to ridicule...

    and losing not only his relationship with you, but your respect.

    I'm sure that you do feel like you're on eggshells, and I truly admire you for being sensitive to this side of him and wanting to give him that acceptance.

    Others have made very good suggestions. If I were him, I would likely welcome some light-hearted indications that you're just fine with the idea. He probably feels cornered; he needs to see that he's not in a corner, but instead that you're leading him OUT of the corner. Gift him with something fun but not over the top, and sooner or later you'll catch him with his guard down and get your opportunity to open him up. Keep it light, and keep it FUN. If it was me I would probably be hesitant - maybe finding it hard to believe that you're really this wonderful. You'll get there.
    Last edited by AlisonRenee; 11-28-2009 at 10:30 AM.
    [SIZE="3"]Ali[/SIZE]

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  7. #32
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    Tasha,

    What a lucky guy he is to have you.

    Yes, so many of us are conflicted over this....drawn to our desire of enjoying our femininity, and racked by the guilt we feel over this societal taboo.

    One thing you might try (since you are open minded and quite giving) is bringing him over to your place for a quiet evening in.

    After a glass of wine or two, ask him: "Would you mind if I give you a make-over? I've been wondering what you would look like if you were a woman."

    Now he can pretend that this is all your idea, and not feel guilty that he wants it so badly. You will see how much he enjoys it.

    Expect that afterwards there may be a few times that he denies how much fun it was (that's the guilt or shame I was speaking of).

    Repeat the experiment one more time, being a bit more elaborate this time.

    Overcoming his reluctance to accept this part of himself will take time.
    I hope he proves worthy of a great partner like you.

    Chris

  8. #33
    Want to Dream? susiej's Avatar
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    "Do, or do not -- there is no try"

    Tasha,

    Previous posts have said "you could try this ..." -- for some reason, they bring to mind Yoda's famous quote from Star Wars: "do, or do not. There is no try".

    In other words, IMHO you shouldn't "try" some strategem like giving him lingerie, asking him if he wants a make over. This opportunity for both of you is way too important to squander on "try". You've got only one chance to "do" it right the first time, and straightforwardness and honesty is the best approach.

    Understand that he's being very brave to drop these hints -- IMHO you must respond relatively soon, or by keeping silent, you will be implying that you do not approve. If he stops dropping the hints, don't think for a moment that he's changed his mind about dressing. As you read more posts in this forum, one thing you'll see we almost all agree on -- those of us who are born with this "privilege" of gender agility get to enjoy it our entire lives. If he stops hinting, he's giving up on you.

    Simply speak to him about his hints, and let him know you're supportive.

    And -- make sure you know just how supportive you are. Could you truly enjoy helping him dress? Shop? Shop en femme? Visualize the two of you out at a lesbian dance club. And, think about how the evening might conclude, at home. Does all, or even some of this work for you? Because if not, you're going to break his heart.

    Thanks for being so understanding! I wish both of you all the best!

    Oh -- and for Heavens' sake, keep us posted on how it goes!!

    Hugs,
    Susie

  9. #34
    Member lavistaa62's Avatar
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    He's Lucky

    He has not only an open and accepting partner but one who goes to great lengths to understand even those things which he may not have revealed to himself. Perhaps he's like myself- more open to unspoken communication which relies on the insight of both parties than the actual spoken word.

    Here's a scenario- a method of extending an invitation. Do you buy him clothes? Perhaps one of those purchases could mistakenly be the female version of something he'd like- jeans or pajamas come to mind. Jeans I guess are a better candidate but the idea is something not obviously female but which, if the spirit within him were to recognize it, he'd prefer in the female version. It shows you understand while not placing him directly in an uncomfortable or awkward situation. If he says no, no problem, just return them. If he puts them on you can compliment him on the fit and the way they make him look.

    Either way, he's a lucky man.

  10. #35
    Member Huntress's Avatar
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    Three Surefire Techniques

    1. Kidnap him and take him under mild duress to a mad scientist. Conversion to a hot babe coming right up. No... wait... maybe he's just a CD'r. Ok. Scratch this one.
    2. Have him abducted by Aliens. Conversion to a gorgeous babe coming right up. Oop... same problem as the first suggestion. Forget this one.
    3. Well, I guess that leaves open honest communication at the uptake both of you can bear. Throw in some Love, and you have won yourself a Twofer. Congratulations girl!

    Huntress

  11. #36
    Just an everyday girl Karen564's Avatar
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    Quote Originally Posted by tasha_shalala View Post
    Dear all,
    I am new here, and I would like to introduce myself:
    My name is Tasha. I am not yet officially a SO of a CDer...but I suspect I have the perspective of becoming one. This is the reason why I come here.

    I have been in a long distance relationship with my partner for more than 3 years now. Things are going steady, but something always seems to be there to hold him back. In the first glance, he seems to be your typical commitment-phobic guy (40, once divorced), who demands a lot of personal space. But during our last few holidays together, I had a feeling that he had been dropping hints: he told me he wanted to try on some of my clothing; he would like to try a manicure and pedicure and make-up session. In some trips, he also bought a lot of feminine accessories...for himself.
    In the beginning I took them as jokes, but eventually due to the frequency of these jokes, I realized it may be no joke at all. I have encouraged him lightheartedly. I jokingly suggested we went for a manicure/pedicure, he then only laughed nervously and said he'd be too shy.
    Once he let me use his computer, and I saw on the website address, there were entries of transvestite websites.

    He's someone very sensitive. That's why sometimes when he seemed to drop hints, I didn't want to poke further. He also has a great tendency to avoid conflict and confrontation. That's why I wonder if I never bring up the issue, will he ever come out to me? Will he ever be ready??? (Of course, provided if he really is a CDer)
    And if I should bring it up, how?
    I feel like walking on eggshell :-(

    I have to say, I sometimes fail to grasp what all the fuss about telling your CDing to your partner. Because for me, it's the person I love. Yet not until these few weeks I have been doing my research on internet, do I realize what a torment it could be.
    How should I go about with the situation now?
    Any input? Or experience to share?
    Tasha,
    My advise to you is very simple here because of your great & loving attitude, so, You need to take the initiative & make the 1st move, because I can pretty much guarantee you he wont, based on what your saying. Find a moment when both of you are alone & a private setting (bed rm?) to make him feel safe, and then come straight out and tell him basically the same as what you said here, that you love the person, not the clothes he's wearing, even if those clothes happen to be girl clothes, and let him know point blank that your fine with the CDing (as long as you really are) but you need him to be up front and tell you no matter how embarrassed or awkward he may feel talking about, but also say you can understand feeling that way, but this is very important to know the truth..
    I's very likely he has never told a sole before, and he may also feel shameful for being a crossdresser, but you also cant rule out the possibility he may have stronger transgender (TS, GID) issues lurking deep inside either, (for that is a more serious matter all together) and this is why it's so important that you need him to be totally honest with you now, rather than 5 to 10 or 20 years down the road if you two got married...

    Good Luck !!!
    [SIZE=3]Karen[/SIZE]

    [SIZE=2]I really do have the...Right To Be Wrong.. [/SIZE]http://www.youtube.com/watch?v=lkSTG...eature=channel [SIZE=2]and my mistakes will make me strong![/SIZE]

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  12. #37
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    you should ask him which outfits he would like to try on.

  13. #38
    Fishers by Indianapolis switcheralso's Avatar
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    Opposite

    I wrote my wife altter supporting her and telling her I loved her. I laid out my desires and past with C/D it went well and now she knows.

    I would take the hints your friend has given you and write a letter in support or tell him your feelings.
    True
    Friendship

    “A friend is one who knows us, but loves us anyway”
    Fr. Jerome Cummings

  14. #39
    Silver Member Jilmac's Avatar
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    Tasha, you sound like a very loving and supportive person, and talking from my own experience I can say that there is a lot of angst on the part of a CDer to come out to his SO. I believe if he has been dropping hints, he's searching for a positive reaction from you. I have a suggestion that might break the ice and free him from his emotional closet.

    As long as you have suspected his love of dressing, and you love him unconditionally, perhaps it should be you that makes the first move in his coming out. You could start by buying him a pretty feminine item (or perhaps an outfit), and surprise him with it. Assure him that you love him and encourage him to get comfortable wearing it in your presence.

    I'm willing to bet that he'll be elated by your acceptance and the bond between you will just grow stronger.
    Luv and Jill


    Straight, into Fantasy Land

  15. #40
    Aspiring Member Joni T's Avatar
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    I think you should ask him in a gentle way. I was closeted to my first wife (it had nothing to do with our divorce) and I came out to my second wife before we were married. We celebrated anniversary #23 two weeks ago. It hasn't all been a bed of roses but at least she knows and is supportive.
    Just my $.02
    Joni

  16. #41
    Silver Member Joanne f's Avatar
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    Quote Originally Posted by Holly View Post
    Hi Tasha and . Any chance CDing was involved in the break-up of his last relationship? That could explain a lot.

    How about trying this... Invite him over and have a nice dinner in planned. Have some soft music playing and a bottle of wine handy. Enjoy some conversation and then send him into the bedroom to "change into something more comfortable." On the bed you have placed some lingerie for for him and a pretty robe. If he comes out asking what the heck is going on, tell him you remember he once asked if he could try on some of your clothes and that you thought tonight would be a good time. If he is open to the idea, then great... you have an opening to engage in further conversation. If he is not open to the thought, the serve dinner and enjoy an intimate evening together. You've planted a seed. I suspect before the evening is over, the subject may come up again. . Oh, did I mention wine?
    That is as a good idea as any .
    [SIGPIC][/SIGPIC]Joanne

  17. #42
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    As A CDer who had a terrible time trying to tell my SO, I can tell you it can be very difficult. You say he has dropped some hints, so maybe you can find a way to capitalise on that. Maybe you can buy him something that you think he would look good in and accompany it with a very nice letter letting hi know how you feel.
    Just a thought, Let us know how it turns out.
    HUGS
    Phyliss TX CD the best of both worlds

  18. #43
    Senior Member kimmy p's Avatar
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    Hi Tasha, I can't give you any better advice than has already been offered. But I will say this, with your attitude about loving the person not the clothing I can guarantee that many here would dearly love to meet you if you and your SO ever part ways.

  19. #44
    Member Jessinthesprings's Avatar
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    Girl he's not dropping hints he's dropping bombshells. You are the dream of every transgendered SO.

    You might say something like this, "I love you. You have been giving me hints that you are a crossdresser. What ever the answer I will be there to support you. I would like for us to go out so we can buy you a new wardrobe and some makeup. It will be our special time."

    Granted you would want to say it in your own words, but if he was anything like me when my wife got me to confess to her, she had to be direct, and had to reasure me that no matter what she would be there to support me, and she also had to be persistant.

    You may also point out that life is better out than bottled up and kept to himself.
    I was told that I was "Way out there In left field", but I don't even know where that is.

    Jess

  20. #45
    Member Maxi's Avatar
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    Turn on a program like RuPauls drag race, and give positive comments on what you like about the girls. This may help to soften him up. See what kind of responce he has. To a macho guy, admitting to having a feminen side is a hard thing to admit to.

  21. #46
    Senior Member paulaN's Avatar
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    Talk, talk, and then talk some more. It's the best, and only way to find out what he is thinking. You have got to start sharing more of your selves with each other.
    keep on gurlin everyone. paula may

  22. #47
    Member Kate17's Avatar
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    If he already said he wanted to try on your clothes, thats the green light. Get something very sexy and get in a sexy state of mind and then ask him if he would try some things on for you. Important -if he accepts the invitation, snuggle together with him wearing the clothes. It sounds to me like he is mentally begging for you to take the next step which will tell him its all right.

  23. #48
    Gold Member sherri52's Avatar
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    Hi Tasha: Nice to have you with us. You have already shown your love by joining us here. Your BF didn't drop little hints, he spelled it out for you. By all means confront him with it even ask if he wants to go shopping while he has your clothes on. The iceberg will be broken and he will respond.

  24. #49
    New Member tasha_shalala's Avatar
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    Dear girls,
    Sorry I have been traveling, hence this late reply. Before I left for my trip, I printed out all your replies and was reading them on my journey. I am so touched!
    My heartfelt thank you to all of you!!!!!!!!!!!!!

    I saw BF only briefly before my trip. The mood was not exactly right and I didn't think it was a good idea to ask him or to have a talk or whatever in haste. So I am still waiting for a better opportunity.
    --This is one of the big problems of having a long-distance relationship, I reckon :-(

    The other day on the phone, we were talking about hosting a few friends from abroad in his holiday house for a weekend. Out of the blue, he asked, "you think they wouldn't find me too strange to wear whatever I usually wear around the house?"
    For one second, I was stunned by the question. But then I realized, he always wears silky house-robe or silky pjs around the house. They are not too feminine, but I guess not totally masculine either! Yet it has never even occured to me that it is the least bit out-of-norm?!?!?!
    So I told him, "It's your house, you wear whatever you like. If you like them, why not? If they don't like it, it's their problem."
    He was in silence for a little while, and then he repeated my words, "yeh...if they don't like it, it's their problem."
    I was hoping he would say something more, but he changed the topic soon after. *SIGH*

    For those of you who suggested my letting him to wear my clothes...there's absolutely no way. Not only he is much taller than me, I also have a more-than-average petite frame. Most of the time, I shop in kid's (not even teenager's) section, so go figure...

    Anyway, I will keep you updated on how things go. As I said before, I am not used to be in a forum, so I may need to learn to be more responsive. But I can't tell you how happy I am to find the community here

    Have a nice weekend,
    Tasha

  25. #50
    Member Amanda Styles's Avatar
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    Quote Originally Posted by Karen564 View Post
    Tasha,
    My advise to you is very simple here because of your great & loving attitude, so, You need to take the initiative & make the 1st move, because I can pretty much guarantee you he wont, based on what your saying. Find a moment when both of you are alone & a private setting (bed rm?) to make him feel safe, and then come straight out and tell him basically the same as what you said here, that you love the person, not the clothes he's wearing, even if those clothes happen to be girl clothes, and let him know point blank that your fine with the CDing (as long as you really are) but you need him to be up front and tell you no matter how embarrassed or awkward he may feel talking about, but also say you can understand feeling that way, but this is very important to know the truth..
    I's very likely he has never told a sole before, and he may also feel shameful for being a crossdresser, but you also cant rule out the possibility he may have stronger transgender (TS, GID) issues lurking deep inside either, (for that is a more serious matter all together) and this is why it's so important that you need him to be totally honest with you now, rather than 5 to 10 or 20 years down the road if you two got married...

    Good Luck !!!
    I can't agree more. Just offer you love and support it everything will work out for the best, IMO.

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