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Thread: My little 16 hour roadtrip - a prisoner no more

  1. #1
    Member Lena's Avatar
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    My little 16 hour roadtrip - a prisoner no more

    Previously, I posted about how crossdressing made me a prisoner in my own house. I can't leave, be seen, blah blah blah..... Others on here said I was a prisoner of my own choosing and I should just go take a ride to see what it was like. Boy, did I do that.

    Last week, I flew to Indiana to drive my wife's car home while she drove my mother-in-law home. (from Indiana to Texas - 1000 miles, 16 hours.) When I got to Indiana, I saw heels in the car and my wife said "I bought some heels and a dress at Goodwill while shopping." A little light went off inside my head. I'm driving her car alone. Nobody who sees me will know me. Yes! I'm driving home in a dress!!!

    On the day of the trip, I shaved my legs and chest in the shower, then started off with a quick trip to wal-mart to get some things. I bought flats, stockings, shorts (clearance for $2), a top and of course some snacks (haha) - oh, and a cheap Halloween wig (bad idea). I figured the wig would be enough disguise if I was seen on the road in a dress. Dang, was I wrong. All that cheap thing did was lose fibers all over the car.... but I digress.

    So, In the wal-mart parking lot, I put on shorts and blouse, stockings and flats. I felt so liberated. I put on the wig and away I went! Cruising down the highway, windows down, sunroof open. At first, when a car or truck would pass, I'd cover my face or look the other way..... as the day progressed, I didn't care anymore and let them look. Of all the cars that passed me, only 1 or 2 even had people looking. I waved and smiled.

    I stopped in IL at a rest park on the lake. It's a huge lake and there's a big park at the rest area to walk, picnic etc. I took a long walk along the beach. I was having a great time. I put the dress on in the car and walked along the lake taking pictures without a care in the world (until a second car came and parked next to mine..... crap!!!!) I stopped at another rest area on a hill in Arkansas where I sat on the picnic table in full view of drivers passing by.

    I filled my car in Texas at a gas station wearing a dress, flats and stockings. Dang pump wouldn't click, so I had to hold the nozzle the entire time it was filling.

    Anyway, in addition to the exhilaration of the outing, I learned that I will never take a long road trip in drab again. It was so comfortable to drive in a dress and short shorts; there was no binding, crushing, sweating etc that I usually experience with Jeans and dude-shorts.

    So, I had such an amazing time, I had to share it with someone. Next time, I'm bringing my wig though!!!!! (yeah, I know the pic on the lake with the wig is horrible, but look at the view I had.)
    Attached Images Attached Images

  2. #2
    Member mikayla1964's Avatar
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    way to go..congrats i'm glad you had a wonderful trip

  3. #3
    Danielle cdinmd206's Avatar
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    I agree with you Lena. Only way to travel down the highway and if by chance a little bare thigh, stocking top and garter strap were to be exposed......

  4. #4
    Gone to live my life
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    Hi Lena,

    Congrats on getting out there and enjoying your drive home.

    Cheers

    Isha

  5. #5
    Silver Member Maria 60's Avatar
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    I bet you wished the ride would never end. I sometimes drive long trips dressed and feels like it's faster when dressed, probably because I don't want the drive to end. Congrats on the courage and confidence and by the pictures looks like you enjoyed it and I could feel your excitement through your words.

  6. #6
    Senior Member UNDERDRESSER's Avatar
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    Long distance driving in a skirt (or dress) is the best way to do it!
    "Normal is what you get when you average out the weirdness that everybody has." Quote from my SO

    Normal is a setting on a washing machine, or another word for average.

    The fact that I wear a skirt as a male should not be taken as a comment on what you do, or do not wear, or how you wear it.

  7. #7
    Junior Member s.e.al's Avatar
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    I've been wanting to do that also, your story wants me to do it even thanks for sharing.

  8. #8
    Platinum Member Beverley Sims's Avatar
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    The only way to pass time on long trips.
    Keeps you awake and aware too.
    Work on your elegance,
    and beauty will follow.

  9. #9
    Member CourtneyBme's Avatar
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    There is nothing like a roadtrip while dressed. About a year ago I had a 2 hour trip home so I packed a bag and stopped at a rest stop to change. I wore something simple. Jeans, blouse, boots, wig, and jewelry. An amazing feeling for sure. I have another trip coming up next month and I will be doing the same to and from the airport

  10. #10
    Silver Member
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    Lena - Congratulations. I am glad you had a great experience. Thanks for sharing. It made me happy, too.

    Just think of the drivers in the hundreds of other cars and trucks that are on the road with you. Unless they are a cop, do you ever care, notice, look at or remember? You should dress the way you want to and feel liberated.

    I am glad for you. And your wife.

  11. #11
    Silver Member
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    I like this story very much and I am so pleased that you escaped the "prison", great pics and the view our the lake is stunning, you give us other "prisoners" hope, thanks for sharing

  12. #12
    Silver Member
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    Way to go! I especially like that you got progressively bolder as the drive went on. It's liberating to know how little others really care how you are dressed. Its not how you dress yourself, it's how you carry yourself. Congrats.

  13. #13
    Member Gabby6790's Avatar
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    So glad you got to get out and do this. I had to laugh at the part about holding the gas pump the whole time. I haven't gotten up the courage to pump my own gas and this would be the proverbial nightmare but it sounds like didn't let it bother you at all. Great job!

  14. #14
    formerly: aBoyNamedSue IamWren's Avatar
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    It was really enjoyable to read this Lena. I could feel your excitement as I read and as I got toward the end i thought, well if there no pics... It didn't happen."

    I guess it ry happened!
    Good for you! Glad it all went well and that you enjoyed yourself.
    I am not a woman nor am I a man... I am an enby. Hi, I am Wren.

  15. #15
    Lisa_vin lisa_vin's Avatar
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    Glad you had such a good time. Windows down, sunroof open........Dang lucky thing you didn't cross paths with any mean-spirited rednecks!
    Lisa

  16. #16
    Member Lena's Avatar
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    Thanks for all the positive comments. It was exhilarating, frightening and fun. I enjoyed the full range of emotions on this trip.

  17. #17
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    Thanks Lena,
    I think you've inspired me, I might make my debut on my next long distance drive
    Adelaide

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