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Thread: Short first outing with wife last night

  1. #1
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    Short first outing with wife last night

    I've been mostly at home dresser, although I have driven places dressed up before, but have never really went out otherwise. Lately my wife has been very positive about my dressing and has encouraged us to go out. This weekend we had an overnight sitter and while the bulk of our evening was a more standard boy-mode date night, later in the evening we decided we should go on a short trip we me dressed up, we decided to go a very friendly dessert place in nearby gay neighborhood. I drove us there, we are able to find parking only about a block away. After getting out of the car we walked right past a large gay bar on the way and the doorman was friendly as we walked past, then we got to the dessert place and we were greeted to "good evening ladies", I'd never been addressed that way before, so it was nice. When we made our order, I let my wife do most the talking and checking out and the guy at the counter asked how the night was going, complimented her earrings she made herself, took a business card from her, while I sort of shyly stood nearby, but it was nice.

    After that we decided we didn't have enough booze at home, so we decided to extend the outing to include a trip the drug store across the street. It was late, but there were a good amount of people there, but everyone was focused on their own thing and in that neighborhood a crossdresser isn't exactly the most exotic thing to see anyway. So we got our alcohol and walked back to the car and finished the evening back our place.

    It was a small simple outing, but it helped break the ice for me and for my wife and it was all positive, so I expect when he have the child care set up to do it again, we'll probably try to go out again and try to extend how much of it is dressed up.

  2. #2
    Junior Member JocelynRenee's Avatar
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    What a lovely story and what a lovely relationship you two have. The outing may have been short, but it sounds like a perfect first night out. I hope there are many more to come.

  3. #3
    Member katlee's Avatar
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    I think it is great that your SO accepts you and embraces the complete you to go out. Any small thing is a big thing when it comes from a person that we care about, especially when it is in the TG community
    I think I feel more like Natalie than I do Kat. I think from this point I will go by Natalie.

    Part of a recently ended relationship where a reason why it ended was my crossdressing.

  4. #4
    MIDI warrior princess Amy Fakley's Avatar
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    What a beautiful story!
    "Why shouldn't art be pretty? There are enough unpleasant things in the world." -Pierre-Auguste Renoir

  5. #5
    Martini Girl Katey888's Avatar
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    What a sweet tale, Cara - thanks for relating it... sounds like you have quite the neighbourhood scene going on and it's great that both of you can share the experience...

    Katey x
    "Put some lipstick on - Perfume your neck and slip your high heels on
    Rinse and curl your hair - Loosen your hips, and get a dress to wear"
    Stefani Germanotta

  6. #6
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    That's great. My wife's really supportive too and I would love to go out dressed with her. It's still new for her so I'm hoping one day we will make that step. Baby steps!

  7. #7
    Gone to live my life
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    Hi Cara . . . what a great story. Sometimes the simplest adventures are the most pleasant and it is particularly nice to be able to share it with your lovely wife. CONGRATS on getting out there.

    Hugs

    Isha

  8. #8
    Member Megan b's Avatar
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    Nice story. I hope to someday meet a lady like your wife. Your so lucky.

  9. #9
    Aspiring Member EllenJo's Avatar
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    What a sweet story. You are so fortunate to have such a supporting wife.
    Hugs
    Ellen Jo
    Somtimes the light's all shining on me, Other times I can barely see.
    Lately it's occured to me.....What a long strange trip it has been.
    Truckin by the Grateful Dead

  10. #10
    Ex prisoner in paradise CostaRicaRachel's Avatar
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    That's sounds like fun! Congratulations. What did you wear on your first night out?
    Although your current visions might be grounded in reality,
    there are no shortcuts to get from here to there.
    Face the facts and realize that you still may have to manifest this
    dream the old-fashioned way: by creating a concrete plan,
    putting in the hard work and maintaining an
    unwavering determination to make it happen.

  11. #11
    Style Icon Sara Jessica's Avatar
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    Sounds like you went to the Hillcrest district, a place that is in fact overwhelmingly accepting. Glad you got out and that your wife was so on board. There are so many fun places to go in SD, your fun has just begun!!!
    Like a corpse deep in the earth I'm so alone, restless thoughts torment my soul, as fears they lay confirmed, but my life has always been this way - Virginia Astley, "Some Small Hope" (1986)
    Sunlight falls, my wings open wide. There's a beauty here I cannot deny - David Sylvian, "Orpheus" (1987)

  12. #12
    Did you say shopping? Caden Lane's Avatar
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    Sounds like an awesome icebreaker trip for the both of you. Hopefully it will be the first of many outings for the both of you.

    Ever & Always,
    Caden Lane

  13. #13
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    Thanks everyone for the nice responses. I wanted to get my positive experience out there, I know when I was lurking this site it was always good to come here and see positive stories and responses, to know you can do what you want things can be ok.

    Quote Originally Posted by Sara Jessica View Post
    Sounds like you went to the Hillcrest district, a place that is in fact overwhelmingly accepting. Glad you got out and that your wife was so on board. There are so many fun places to go in SD, your fun has just begun!!!
    Yes we went to Hillcrest, for now if we go out that is where we are going, the easily the most friendly neighborhood for something like this and it's one of our go to neighbors to go out to anyway, although our daughter significantly cut into our going out.

    Quote Originally Posted by CostaRicaRachel View Post
    That's sounds like fun! Congratulations. What did you wear on your first night out?
    Black top, leopard skirt, some hosiery and flats. The flats were a good low stress choice, so I wasn't overly tall, not awkwardly wobbling around, they are quiet to walk in and just a bit more blending. My wife prefers flats for me too, she likes when we are around the same size. I wore my fake glasses I have too, to be a bit more obscured and I think they are cute anyway. Maybe I'll post a pic of the outfit later, need to get it off my phone.

  14. #14
    Platinum Member Beverley Sims's Avatar
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    Carah,
    It is those smal outings that lead to better things.
    Enjoy your progress.
    Work on your elegance,
    and beauty will follow.

  15. #15
    Neanderthal in nylons Julie Denier's Avatar
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    That's terrific, Cara! Sounds like a great way to dip your toe in the water. So nice to have that kind of support at home, too

  16. #16
    New Member FemmeMonique's Avatar
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    Does your wife have a single sister?

  17. #17
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    Quote Originally Posted by FemmeMonique View Post
    Does your wife have a single sister?
    Yes actually, she gave me one of the tops I'm wearing in the post I just made pics section. I don't know if she's currently looking though. For anyone interested in what I wore for this outing I included a pic of the outfit there.

  18. #18
    Diamond Member Persephone's Avatar
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    Congratulations!

    Hugs,
    Persephone.
    "If you are living the life you want to live you've successfully transitioned to being the person you want to be." - Eryn.

    "If you truly care about me you should damn well want for me what I want for myself" - Michael Westen (Burn Notice)

    -.-. --.-/-.-. --.-/-.-. -../ Persephone™ and Persephone™ are trademarks of Persephone herself, accept no substitutes. The terms "en femme" and "en drab" originated with Marcia Sampson/Staylace (OBM).

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