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Thread: Big, crazy step

  1. #26
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    Good luck, I hope you have a good time.
    Let us know how goes.
    Sara

  2. #27
    Senior Member MissTee's Avatar
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    Bet of luck, Kaley. That trip sounds so exciting.

  3. #28
    Aspiring Member Fiona123's Avatar
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    Big step, but not at all crazy. All the best.

  4. #29
    Aspiring Member kaleyg's Avatar
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    Looks like we're postponing the retreat for June. But we've ordered a couple outfits online, along with a wig, forms, underwear, makeup, accessories, etc. She's ordering clothes that she likes and more in her sizes in hopes of expanding her wardrobe, but I'm not complaining. I would prefer to show some leg, but she likes maxi dresses and skirts. But she has AMAZING taste, so I feel like I'm getting a professional wardrobe consultant. I imagine that she may be thinking this will get it out of my system (someone suggested that), because we're not doing this half-way. When the forms came in the mail, and we tried them out, I think that was hard for her -- it was super awkward for me. I've never worn them before and certainly not with someone looking at me! I found myself crossing my arms to cover up like a girl would. But she helped me adjust the bra to fit with them. I will definitely shave my chest next time before adhering them! (using tapes) OUCH! Fortunately, my chest hair was really only 1/8 inch stubble, since I had shaved for a triathlon a couple weeks ago.
    I am a little surprised at how much money she's spending -- she's ordering the make up from her Mary Kay lady (she gets it all at cost). I'm used to buying make up at Walgreens -- the cheapest I can find. I'm assuming the make up is in her colors, too, rather than mine. But we're not that different.
    One thing she has made VERY clear is that we will not be leaving the hotel room. I'm hoping that after a bottle of wine, she'll send me down the hall or to the lobby for something. But she is absolutely TERRIFIED of us being recognized. So, I'm trying to come up with fun ideas for us to do in the hotel. I'm also assuming that I shouldn't make any attempt (even after a couple bottles of wine?) toward intimacy. I'm almost 100% sure she would FREAK OUT. But, I'll just see how things go.
    Love your feedback and advice! Thanks girls! xxoo

  5. #30
    Senior Member Diversity's Avatar
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    Good luck to you both, and I hope all goes very well!!! I hope to have such a weekend too, but it is doubtful, at this point in time.
    Please post an update, as it would be interesting to hear how things went for you both. I'm sending positive vibes your way, Kaleyg!
    Di

  6. #31
    Aspiring Member kaleyg's Avatar
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    Ok, the retreat is back on for the 25-26th! We tried on some things yesterday and with the waist cincher and forms I can't believe my figure. The forms & bra are only 38B, but with my waist cinched, they look bigger. I keep wondering what she thinks when she looks at me like that -- is it the way I would feel if she were wearing a fake beard and had a sock in her pants? Or does she think I'm cute/attractive? I guess I'll ask at some point, though I think she would have a very hard time admitting any thoughts/feelings that might make her feel anything but pure heterosexual. And that's fine. Some dresses coming in the mail that I haven't seen yet. Looking forward to trying them on!

  7. #32
    Nikki Windsor nikkiwindsor's Avatar
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    Kaley, What an amazing experience the two of you are planning! I know you don't take her for granted...from what you've shared w/ us she's someone very special! Nikki
    Wearing my fuschia bodycon dress:
    http://imgur.com/6WkdAts
    For the first time, outdoors during the day:
    http://i.imgur.com/RmjIxbY.jpg

  8. #33
    Platinum Member Beverley Sims's Avatar
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    I say all the best, you have had some good advice from others about not overwhelming the situation, so, play it carefully and let your wife lead.


    Don't seek any opportunity to push the issue, I think you are on a winner here.
    Work on your elegance,
    and beauty will follow.

  9. #34
    Senior Member Jenn A116's Avatar
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    Sounds like the whole package is coming together. Wishing both of you a very happy experience.
    Jenn A --- nothing fancy, just me.

  10. #35
    Aspiring Member kaleyg's Avatar
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    Ok need ideas!!! If she doesn't want to leave the hotel room, give your best ideas for a girls night in. ; )

  11. #36
    Silver Member ClosetED's Avatar
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    You are so lucky!
    I would definitely try to keep the interaction to two girlfriends/sisters, and not try any husband to wife actions, unless she initiates.
    So certainly with many new clothes and makeup, you can do a fashion show and take along a camera to take pictures of HER and she can choose to take pictures of you. You can sit and have tea,and just talk. She is likely to want to know what thoughts go through your mind while dressed, so bring up some topics like that. Are they the same thoughts as her husband, or more girly? You can watch a chick flick and talk about that and then do a pillow fight at bedtime.
    You can play act - pick a scene from the movies or TV and play it out for laughs.
    You can be the French maid and let her direct your actions.
    Be the masseuse and massage her, but that may be better for her husband to be the masseur.
    Just some thoughts
    Hugs, Ellen

  12. #37
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    Kaley, you need to discuss what she really fears. Is it being recognized only? Your safety? Hers? Something else?

    staying in and watching a move is not going to be the same as at home in boy mode. No holding hands, sitting close, etc., right?

    When my wife first went out with me she was so nervous for me, on constant alert, she couldn't enjoy anything. And we were in Hawaii! Once I spoke to her and understood her concern, I set her straight: I'm a big boy and can deal with whatever negative consequence may come (none have, of course). Now she has completely let go of any self imposed responsibility for my outing. In her words, "We are just two people out." She can enjoy herself now and see past the "costume." That kind of letting go is not immediate nor simple, but should be discussed.

    Good luck

  13. #38
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    A wonderful thing is happening to you both. For the hotel plan an exquisite dinner in your room. Table cloth, candles, champagne and wonderful meal. That and a deep and real conversation could be a perfect evening with nothing else planned. May you both have a beautiful evening. And maybe a stroll later in the evening, after dusk in a pretty area if she feels comfortable. Alice

  14. #39
    Senior Member Diversity's Avatar
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    Good luck to you both. I hope that you both have a lot of fun and celebrate your time in doing this with all the love and mutual respect you each are demonstrating to one another.
    Good luck, and I hope you post an update of this experience.
    Di

  15. #40
    Aspiring Member kaleyg's Avatar
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    We're doing a "dress rehearsal" tomorrow to see how things fit and practice with make up. (I really haven't let on how experienced I am.) Hopefully she is able to get the beard cover down! I hope to have a pic of that tomorrow. Maybe even of us together!
    Apparently she's read some things on sexual addiction and cross dressing and is hoping that doing this will help break the "addiction". But, in any case, it feels like progress.
    I may look different because of the wig she ordered. It seems like she wants to be in control of things.

  16. #41
    Madam Ambassador Heidi Stevens's Avatar
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    Hey Kaley, as long as she's interested, let her control things this go round! Make adjustments when she's not looking. See if she's up to doing a run to Sonic and interact with others. Tell her to watch others reactions. I got a feeling she's going to see every day life! Have fun on the trip.
    Be yourself. Everyone else is taken!

  17. #42
    Aspiring Member kaleyg's Avatar
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    dress rehearsal pics!

    here's a few pics from the "dress rehearsal" today (completely un-doctored!). The one in the bathroom she took, the others I took. I thought the hair style would be fun, but I don't like it in the pics. The dress really seems to give me the inverted triangle -- broad shoulders -- yuk! Hip pads on the way! Probably need more makeup. : ) Not my usual look, but she did a good job. and OMG my eyebrows!!!! aaauugghh! I tried to get her to take a selfie with me, but nope. Maybe next week. ;-)
    Attachment 261415
    Attachment 261416
    Attachment 261417

  18. #43
    Silver Member ClosetED's Avatar
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    Again, let her be in control and do what she feels comfortable with. You certainly look feminine, so she needs to be OK with that. She may not be ready for too girly.
    Let her do it, then later, offer to make a change and see what she thinks of it.
    Hugs, Ellen

  19. #44
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    Quote Originally Posted by kaleyg View Post
    ...Apparently she's read some things on sexual addiction and cross dressing and is hoping that doing this will help break the "addiction". ..
    Kaley, I am shocked that you wrote this and then followed that it felt like progress. If this is her understanding, cross dressing is like sex addiction and can somehow be "treated" she is a long ways from your understanding of your cross dressing. This is THE discussion you two need to have. What happens when you two return to your house and she thinks it's now over? That you've gotten it out of your system or is now under control? There is life after the weekend....

    Quote Originally Posted by kaleyg View Post
    ... I thought the hair style would be fun, but I don't like it in the pics...
    The typical,problem with pulled back hair on cross dressers is that it highlights the male jawline. Not something we typically want.

  20. #45
    Aspiring Member kaleyg's Avatar
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    Jennifer -- I think, for me, there are two sides to cross dressing: a sexual side and a non-sexual side. The sexual side does feel addictive, like the way other men use porn. I'd love to be rid of that -- it makes me obsess over dressing. and I'd rather spend my sexual "capital" on my wife. But there's a non-sexual side that is just expressing something feminine inside me, and I'm hoping she'll see that and how happy it makes me. once she sees that it doesn't have to be sexual, I'm hoping she'll be more open to it. And I wasn't about to turn down the retreat or her participation! : )

    As for the hair, yeah, I'm keeping it down next time!

  21. #46
    Ice queen Lorileah's Avatar
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    I think you look fine. So many here say you need to "blend" and the hairstyle is one that women would wear at least while driving, to keep the ends from tangling. Also, the shape of your body is fine. The pull to the side helps. Of course hip pads never hurt.
    The earth is the mother of all people and all people should have equal rights upon it.
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    “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,

  22. #47
    Madam Ambassador Heidi Stevens's Avatar
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    I'm with Lorileah, Kaley, if you can round up some hip pads before you go, you'd be 100% to go in my opinion!
    Be yourself. Everyone else is taken!

  23. #48
    Aspiring Member kaleyg's Avatar
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    Hip pads are on the way! Friday night, as part of our "dress rehearsal," we decided I should sleep with my forms in my new cotton night gown. I know this sounds unbelievable, but again, I really think she's hoping this will *decrease* my desire to crossdress. I'm hoping that the retreat will help her become more comfy with the idea of me dressed. We ordered another dress on amazon that is super fun. I'm about 90% sure we'll have pics to share after the retreat.

    I'd still love to hear activity ideas, or small ways I can be seen around the hotel without us "going out." I'm just about certain that's not happening.

  24. #49
    Aspiring Member kaleyg's Avatar
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    Tomorrow is the big day! I can't wait. I'll start a new thread in the picture gallery on thursday, hopefully. Last minute tips or ideas?

  25. #50
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    Good Luck on the great adventure and let us know how it turns out!

    Of course we want to see pictures!!!

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