11 Responses to “Cross Dressing Confession: How Should You Tell Her?”

  1. DanAndJenn Says:
    February 3rd, 2009 at 5:27 pm

    did it hurt? are we talking play nibble or much, munch “yum that tasted great” type of nibble?

  2. SexMan856 Says:
    February 3rd, 2009 at 6:23 pm

    she actually started to nibble harder and harder like she was chewing or sumthing. it did hurt once she nibbled hard. i think she was probably hungry wen we were doing oral, it was night and we had no lunch or dinner. she said she wasnt hungry, but wen she was nibbling it sounded like she was daydreaming bout food or sumthing. i dont no, but it did hurt. i pushed her bak once she started nibbling TOO hard.

  3. KunoichiKira Says:
    February 3rd, 2009 at 6:25 pm

    i agree with the heart to heart idea, mainly because people can react badly to simple, shallow hints. if my boyfriend decided to crossdress, hey thats fine with me but i gotta see it coming. have a chance to get used to the idea, yknow.

  4. WAMadden4 Says:
    February 3rd, 2009 at 7:04 pm

    If a “man” crossdresses he is gay, no ifs ands or buts… what a loser!

  5. ursaucie Says:
    February 3rd, 2009 at 10:19 pm

    I am with you all the way Madden4!!!!

  6. Playgirl2day Says:
    February 5th, 2009 at 11:10 pm

    l just couldne see myself with a man who likes wearing womens cloths
    but then if its love who know what l’d except

  7. me100200300 Says:
    February 6th, 2009 at 3:14 am

    I dont think he should drop hints, I think he should just tell her, but I also think sex should be a fun thing, not over serious, so when he tells her if he makes it sound like it shouldn’t be a big deal, its just fun, then she might see it that way, but if hes going to be all dramatic and deep about it she might get dramatic too and think into it too deeply. But its hard to know without knowing the people and everything.

  8. Danzation36 Says:
    February 6th, 2009 at 7:24 am

    I would be alright with that, it’s not necessarily gay.

  9. mannhead79 Says:
    February 8th, 2009 at 11:47 am

    im a crossdressing bloke and think that some of those coments r pretty harsh….there arent too manu guys out there like us but i think that u girls should look at us as normal guys

  10. onewhoistoasted Says:
    February 8th, 2009 at 2:57 pm

    He don’t want to tell her :) that’s why he is on the defence.

  11. GentlemanJim Says:
    May 4th, 2009 at 4:46 am

    I have been married to two women that accepted this part of me. My first wife (died in 1984) was the first person I ever shared this with. It took her time to accept it, but in time she even enjoyed my cross dressing to some degree. She even borrowed some of my clothes. My second wife took the confession as if to say, “so that’s all there is?” She had no problem with it at all. It all comes down to how much trust and love there is between you and the woman in your life. Our divorce 19 years later had nothing at all to do with my cross dressing. My most recent relationship was with a very dominant woman that actually found it a turn on and was in fact part of the reason she was attracted to me. Sadly, that ended leaving me to look for love once again. I will tell the next woman I am attracted to. I can not and will not try to hide this part of me. But if you tell them to soon, you may turn them off and end what otherwise would have been a good relationship. On the other hand, I don’t want to wait until she feels deep commitment to me and this might hurt her. So it’s a hard callas to when to tell. Maybe just feel her out in general about different alternate lifestyles to see if she is judgmental or turned off to anything out of the so called norm. I am seeing someone now and believe me, it’s scary to think about telling her now. In time, I’ll know if she is open to it or if I need to find someone else…before that love bond is strong enough that either of us gets hurt.

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