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Thread: Does crossdressing ever get "boring?"

  1. #1
    Aspiring Member
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    Does crossdressing ever get "boring?"

    Well, certainly not for me.
    Just turned 50 and I'm enjoying crossdressing more than ever.
    I still love shopping for clothes, trying on new outfits,
    discovering new styles of lingerie, etc. etc. and, of course, learning
    from others on this wonderful website.
    So, for me, crossdressing never seems to get "boring" and
    I'm curious to know if that's the case for others out there?
    Last edited by il.dso; 03-10-2011 at 10:11 AM.

  2. #2
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    I can't say it gets boring, but it does get frustrating at times as things don't turn out exactly like we are hoping....

  3. #3
    Silver Member Tina B.'s Avatar
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    I don't know if it gets boring or not, but after 60 years of dressing, I still wake up planning what to put on and how I'm going to match them up. Last night I decided to go drab today, I've been dressing for quite a few days in a row, and figures maybe the wife might like a break. But then I woke up real early this morning, figured a had a few hours before she gets up, so maybe I will play for a while. by the time the wife got up, I have red nails, and toes. dressed in a cute scoop neck top that's white with black flowers all over, and a pair of black leggings, toped off with a wig, red heels and earrings and bracelet. The wife went to work, and I'm dressed for the day, and again, I missed that chance to show her my guy side, it's getting harder to find, and she sees it a lot less these days, because it's DRAB that I find boring.
    Tina B.

  4. #4
    Gold Member Cynthia Anne's Avatar
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    NO, no, not, nicks, never! Any way you say it! The answer always comes up the same!

  5. #5
    Silver Member RenneB's Avatar
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    Boring no, absolutely not. Costly, yes. The hair, makeup, undergarmets, pads, shoes, dresses, outfits. I'm shooting for an evening gown now and really lookin' forward to the next outfit that I can put together..

    It's just what I feel comfortable doing...

    Renne (.)(.)

  6. #6
    Life is for having fun. suzy1's Avatar
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    Because Suzy is a real part of me then it simply can’t become boring.
    It’s not a pastime or hobby for me. It is me!

    A happy, SUZY
    Last edited by suzy1; 03-09-2011 at 12:48 PM.

  7. #7
    darlingdenise hotskirt's Avatar
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    Never gets boring. Gets better every time I dress. Oh wat a wonderful dress!!

  8. #8
    ghost Anne2345's Avatar
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    Uh, no. As in no, no, and no. Did I mention no? If not, then no!

  9. #9
    Future Crazy Cat Lady josee's Avatar
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    Can't imagine ever thinking that getting dressed in hose, a silky slip and dress would become boring.

    If it did I'd just go Shopping!

  10. #10
    One Perky Goth Gurl Pythos's Avatar
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    Boring no. As stated earlier it can be frustrating. Usually due to the perception of what other people will think. Or having to hide from nosy parents, or un accepting SOs. It is also frustrating when reading of people who have the family and economic backing...hiding. It helps not one whit.
    I do feel though that I am approaching the end of my alternative style days. It is very depressing at times to be honest.

    But, boring? No. Drab, now that is boring.
    "I am not altogether on anyone's side as no one is all together on my side"
    Tree beard. Lord of the Rings, The Two Towers.

  11. #11
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    I personally think its gets better as time goes by...
    When i started dressing properly again a few years ago, i was content with just staring at myself in the mirror - usually wearing just a bra and stockings and perhaps gloves and silky gown, but now I love the time where I can dress, and i just don't notice it - i get on with own things, and then look down at a cup and see that it's my lipstick that has left a mark like that.

  12. #12
    Silver Member darla_g's Avatar
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    There has to be some level of satisfaction. After I am all made up and dressed I take a look in the mirror. If I like what i see then great! But there have been times i have been really unhappy with it and vowed to never do it again.

    Right now I am very happy doing it, but its not like I dress that often so it never is boring.

  13. #13
    Silver Member AKAMichelle's Avatar
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    It can become mundane, but that when you have crossed over the line and become much more than a crossdresser. At that point it is more about being true to yourself.
    Michelle

  14. #14
    The Girl Next Door windycissy's Avatar
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    Great question. For me, just trying on those wonderful, forbidden clothes was excitement enough for the longest time, but eventually I felt bored and frustrated just sitting around my pad or some hotel room, all dressed up with no place to go. What really changed everything for me was going out, first with baby steps, eventually becoming more confident until I finally started meeting people as a woman, now I never dress up just to put on the clothes, it's always to go do something as Cissy!

  15. #15
    Junior Member Laura De Santis's Avatar
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    boring ,boring.....
    yes it s boring when i can't get dressed as Laura
    and ABSOLUTLY NO when i can do it

  16. #16
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    Then only thing that gets boring for me when dressing is shaving my legs...hehe...As much as I loved my legs done, it seems like the same old thing every time...But it must be done....
    "WE may not all be compatible, BUT there's no reason why we can't all be friends"

  17. #17
    Jeannie Jeannie's Avatar
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    I try to give my wife a break by not dressing everyday and since I don't go out dressed I am in drab more than I am dressed as Jeannie. When I do have the opportunity it seems to be more fun and satisfying and I can do it for a whole day with makeup and everything. I am happy with the situation and don't mind having to be drab because I have a ton of remodeling to do on our house and for me it easier to do it in drab. Besides I don't mess up my skirts and blouses with sweat, paint and glue all of which I manage to get all over the place.

    Jeannie

  18. #18
    Platinum Member
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    Boring never as I get older it just gets better some evenings I may be to tired but never bored.
    I have enough of a collection that I can keep different all the time although I do have
    some favorite outfits, shoes & wigs that are aways in the ready position in the head of the line.

    Orchid

  19. #19
    Truth, Love, Freedom Angiemead12's Avatar
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    the only boring bit is getting all dolled up and got no where to go!

  20. #20
    Aspiring Member Sandy Banks's Avatar
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    Well, I believe it's becoming more and more addictive..................................is anyone else experiencing this????
    [SIGPIC]

  21. #21
    Member DianeDeBris's Avatar
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    For me, as one individual, I always love the clothes, the look and tactile feel of my things, all of the sensory inputs -- the opportunities I have to get out and about are precious to me -- and I'm in Seventh Heaven when I am able to get myself done and get out -- my interest and enjoyment never flag -- yet sometimes it is simply too much work, takes too much time and effort, in comparison to the time I'd be able to enjoy my presentation, and I simply have to make a basic cost/benefit analysis that leads me to do something less demanding -- being a woman is a lot of work!

  22. #22
    Female Illusionist! docrobbysherry's Avatar
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    Boring, Il? Yes, of course! After 2 weeks of planning and an entire weekend wasted dressing and shooting pics, well, u know! I've had enuff of THAT NONSENSE! So many more productive things to do with my time!

    Organize the garage. Clean the house. Read a newspaper. Watch the Lakers or Ducks.

    OMG! Did u see the dress on that hottie in the 1st row? I think I saw one like it at Goodwill. I MUST head over tomorrow and see if they still have it! Oh yeah, and I need some brown knee hi boots, a new Spanx, and I'll go by the 99 Cents store for some dark tites------what else? I just KNOW I'm forgetting something!?
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  23. #23
    Complex Lolita...
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    Quote Originally Posted by il.dso
    Does crossdressing ever get "boring?"
    [SIZE="2"]It only gets boring when I find myself “discussing” the same old subjects over and over AND OVER with the same members, or new members, or anyone unfamiliar with the mysteries (or terminology) of crossdressing. It’s always fun, and never boring, to crossdress, but thinking too much about it turns a beautiful thing into a tedious exercise – I mean, it’s fun to talk about, but it’s much more fun to simply enjoy crossdressing and live with the inevitable consequences. Once I’m dressed, boredom is impossible to achieve…
    [/SIZE]

  24. #24
    Member Tanya C's Avatar
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    Well, every once in a while crossdressing may seem a little boing, but it's certainly not a problem that a new outfit wouln't solve. Or a new pair of cute shoes.

  25. #25
    Gold Member erickka's Avatar
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    Not at all. If anything, the older I get, the more interesting and fulfilling crossdressing has become.

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