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Thread: Dilemma! Do I Or Don't I?

  1. #26
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    I'd suggest you go as Alan, and try to get a sense of what they're thinking about you. Since the socialising relates to your work environment, you should proceed very carefully. If you ever go out with them as Sara, all your colleagues will sooner or later know about your crossdressing. How will that affect your job?

    Just my

    Jan

  2. #27
    Member Girly Sara's Avatar
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    Hi girls!

    Thanks so much for taking the time to respond to my question. You've all raised some interesting and useful points. This scenario is a tricky one and i don't know what to do for the best.

    Not sure when the night out will be but will have to cross the bridge when i come to it. The thing is, i'm so relaxed and confident chatting about girly stuff at work, although i don't give a lot away. With this, i don't say "oh i've got a top like that" or "i must get my nails done like that" I just comment on their clothes and other stuff and it's clear i have an active interest.

    I'll update you as and when/if the night out occurs in due course and thanks again for your help, girls!

    Take care.

    Sara xxxx

  3. #28
    Platinum Member Barb Valentine's Avatar
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    Good luck Sara on what ever you decide
    But let know how you made out

    Barb
    I just don't have fun -- I make the fun

    Life's too short........Enjoy every day

  4. #29
    Lingerie Lover RachelDenise's Avatar
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    If you don't know them very well, I'd go as Alan, but wear some non-descript girly clothes. That way a hint or two is out there. Gauge them, get to know them and they you. If it seems like a good group and you have broken into some confidential conversation, then I assume you have been accepted. It's then up to you how you want to broach the subject. Be ready for the consequences....one of them may be jealous if you're prettier!!!!
    Rachel Denise

    [SIZE="2"]“One day Alice came to a fork in the road and saw a Cheshire cat in a tree. ‘Which road do I take?’ she asked. His response was a question: “Where do you want to go?’ ‘I don’t know,’ answered Alice. ‘Then,’ said the cat, ‘it doesn’t matter.' "
    - Lewis Carroll
    [/SIZE]

  5. #30
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    (curtsey)

    What the other girls said about casing the coworkers out is good advice.

    i know another CD who was in a similar situation with the party invite and he showed up dressed. The GGs freaked out, a couple of the gossip hounds put the word out at the workplace and he ended up having to leave a job he really liked. I hurt him in finding another job because he got a neutral reference.

    Scope it out well before you do anything.

    (curtsey)

    -sissy s.
    Last edited by sissy stacy; 08-06-2006 at 10:17 AM.

  6. #31
    It's Never Too Late QZ2's Avatar
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    Their idea

    Sara, it sounds like you have already well thought out the consequences of their finding out about your CDing and how it applies to you workplace.

    It was their idea to ask you to join them for the girl's night out. With a little ingenuity you could make it their idea that you go with them as a girl. Like, "How could I go with you girls on your fun night out without being a girl myself?" or, "If I was a girl I would be delighted to join you, it would be a lot of fun. Maybe I could borrow one of your dresses, ha?"

    Maybe they would think up a great idea themselves: Gee, we could dress him up, put make up on him and he would make a good looking girl. Let's try it!

    Good luck and have a great time. I wish I could join you.

    Luv, Susie
    “I am what I am and that’s all that I am"...Popeye

  7. #32
    Want to Dream? susiej's Avatar
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    Take your time, do it right

    Sara,

    What a golden opportunity this *might* be! We've seen several of posts like this on this forum, and mostly, the advice is "be very careful, this could be a disaster". But, the way they approached the subject with you makes me agree that, yes, they probably know or suspect, and they're at least sort of OK with it. What's more, it seems clear that they like you -- and, even better, they like you the way you are.

    Yes, this could be a fiendish diabolical female plot to embarass the %$#@ out of poor old Alan, but your story certainly doesn't read that way (one question that comes up as a result of this thought is, are you painting the picture excessively rosily for us?).

    When you go out with them the first time, and everybody has fun, and nobody's weirded out, it won't be the last. Rather, it could be the beginning of a splendid series of nights, that could be a turning point in your life in more ways than one.

    So, my advice is: 1) absolutely go do it, but 2) first time, no (big) surprises. Wear something consistent with what you wear to work, but maybe a little "more so". Give them the same spot on the boy-girl scale that they had at lunch, first time. The wonderful, delicious thing about this situation is, if they know, and they're OK with Sara, they will probably let you know. They might even encourage Sara to be more herself next time.

    And, first things first, you've been invited to a girls' night on the town, with a bunch of people you seem to like, and who seem to like you. Why optimize?

    Go, girl! You're in a dance with them, and they're leading. All you have to do is follow.

    Hugs,
    Susie

  8. #33
    Member fionasboots's Avatar
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    Be careful out there

    Well, first off I'd have to say you really could fit in as one of the girls as you look so convincing in your avatar and absolutely stunning - I'm really jealous!

    And maybe that could be a problem, like people have said before there could be one that just doesn't like the idea and if you really do go all the way with the dressing up that may only make matters worse.

    On the other hand, I ignored advice here when I asked about telling one of my coworkers about my CDing because I believed she would deal with it really well, and she did, in fact much much better than I had hoped.

    So it really could be the start of something really good and positive, but only if you can be sure they will all take it reasonably well and that either they'll keep it as a girlie secret amongst themselves OR that you don't care if the gossip about you gets out.

    I really, really hope you can go out as Sara and be one of the girls, it really does sound like it would be a wonderful thing to happen
    Fiona

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    Does my bum look big in this?

    http://uk.360.yahoo.com/fionasboots

  9. #34
    Member Jodi Lynn's Avatar
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    Quote Originally Posted by Sophia Rearen View Post
    Well, Sara, one of the toughest things to do is, how are you going to bring up the subject again? I'd say, "I'm sorry, ________ , I am a little confused by what you said at the pub, about going out for a girls night." If she repeats it in a similar fashion as in the pub, you may want to ask, "what did you have in mind?" My advice, go for it. To be one of the girls at work, is like a cders dream. If you don't, You may hate living with this lost opportunity.
    I agree with Sophia. I would ask if what they ment when they said a "Girls night out". I know i wouls love to go out with a bunch of gg's as one of them if I had the chance. Also , if you were to go with them yoyu know you would be out to everyone you work with not just the girls.
    Hugs Jodi Lynn

  10. #35
    Adventuress Kate Simmons's Avatar
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    My advice

    Go as Alan. I think you'd enjoy it more. Ericka

  11. #36
    Krysten Krystenw's Avatar
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    Been There

    Quite a few years ago I was the only guy working with 26 women.
    One year we were going to have an office party and to my surprise a couple of the nurses thought I should come as a lady since I was the only guy and they didn't want me to feel left out. Back then my hair was shoulder length even after it was permed. I usually combed it back so it wasn't too feminine looking.
    Jokingly I told them I didn't know where I could get a dress or shoes big enough to fit me. They told me that if I were man enough to go out with them in a dress they would find something for me to wear. That I should be at their house at 4:00 Saturday afternoon and to be sure to shave my legs.
    To everyone's suprise I showed up as directed. They had a very nice outfit for me and they all had a great time fixing my hair and makeup. They were all suprise to find that my ears were even pierced. They hadn't even notices before. When we were finished we all went to dinner and had a great time.
    Most of the ladies didn't even know who I was until I said something and then they recognized my voice.
    Anyway to get to the point. There were several there that didn't think it was right for a guy to go out in a dress and made things so miserable at work that within three months I found another job.
    So just be carefull.

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