Viewing 11 reply threads
New Forums
  • Author
    Posts
    • #604397

      Well, it was truly a baby step but for the first time I was out today dressed entirely in ladies attire and in the daytime!  My only other outside dressed experiences were a Halloween party some 30 years ago and a late night drive nearly 45 years ago.  This excursion has been a while in the making and was planned out but once I had my first outfit in hand I sorta jumped the gun and took my plunge.  The baby step part is that my outfit today was femme but leaned quite a bit on the androgynous side.

      The plan for my first outside outfit was to shift my daily exercise gear from male to female to wear on the many walking paths we use in nearby communities. I purchased a number of ladies v-neck silky exercise tees in decidedly bright colors, a couple pairs of womens lightweight cargo style walking shorts and ladies running shoes and no-show white socks.   And of course an appropriate sports bra.

      It all felt great wearing together and I was very excited as I’ve been a life long runner/walker and exercise participant and have ALWAYS had the desire to dress and exercise in all the wonderful attire I have seen on the ladies over the many years.   The weather turned very favorable today and my wife wanted me to run some errands after lunch.  So I just decided that today was going to be the day to go out dressed and the shopping center in a nearby town was where it was going to happen!

      I applied some light eye makeup, made sure my bare legs were smooth, selected my favorite satin panties and put my outfit on.  My wife was a little bit surprised but when asked she told me that I would attract little to no undue attention in what she saw as a pretty androgynous look and to her I looked like I was just coming from the gym or a run.  No matter to me, it was all about how I felt inside and that was a little nervous but otherwise elated!

      I drove myself to the shopping center where I first used the lobby ATM at the bank and then it was over to the supermarket.  The COVID/flu is hitting pretty strong here right now so I received a little bit more anonymity by wearing a face mask and I also added my wife’s small brimmed walking hat to lessen the impact of my thinning pate.

      The sensation of walking in these fairly skimpy clothes for January was sublime, especially  as I went through parking lot and  inside near the cool air of the refrigerated sections of the market.  As I wound up and down each aisle the nerves eased up and I was able to just take in and enjoy the moment.  And my wife was right again – for the most part I went unnoticed except for when I felt a couple of older women may have given me an extra second on their glances as we passed each other.  There was also a man who seemed to shadow me for a couple of aisles and then come up and pause closely behind me as I scanned and knelt to pick up items on the shelves…but then again I may have just been imagining that.  The young lady checker also gave me just a bit more notice than I ever normally received but was also very much more friendly and talkative than I was used to so I’m sure she knew something was up with me but obviously wasn’t bothered by it a bit.

      The cherry on top of the cake was when I got home and while unloading the groceries, my neighbor came over to talk to me about some work he was getting done on his house.  I just decided to stand tall in front of him and not try to hide at all.  He also didn’t seem to notice anything out of place with me, even though I’ve never worn anything so bright, tight or leggy outside in the neighborhood.  I’ll chalk that one up to knowing that men can be pretty non-observant. LOL

      So it all went well and I can’t wait to hit the walking trails in semi-fem presentation now with new confidence. I think the experience today is also is an encouraging sign toward my goal of working up to a much more complete and unquestionably feminine mode of dressing in the open world.

      – Kayla

       

       

    • #604407

      Congrats to you Kayla. A memory that will stay sith you. It shows that people dont care, as lng as they are not affected. But we still suffer from worry over what others think.

      Best wishes
      Jane

      • #604549

        So true this will be a lasting memory Jane. But now I feel much of the worry has melted away and so time for the journey to continue!

    • #604409
      Anonymous
      Lady

      WAY TO GO, KAYLA!!  That first baby step is a big one!  It brings an entire new world into view and, if you’re like me, now that you’ve done it once, you want to do it ALL the time!  The first time is just SO thrilling and nerve-racking at the same time! Congrats!!

      *kisses* tara 🙂

      • #604548

        Spot on Tara, now that I’ve broken through that wall of trepidation I so feel that there’s no going back!

    • #604411
      Twilla Thompson
      Baroness - Annual

      Awesome outing!  Perhaps the cashier was just being chatty with another lady!

      Toodles

    • #604493

      Way to go Kayla,

       

      It is great you are getting outside.  Enjoy your adventures.

      Paula

    • #604522

      Hi Michaela,

      Baby steps is exactly how i started and it truly is a confidence builder. Keep going! It only gets better and you’ll get braver and braver.
      I too am an avid walker and walking the beach or on the treadmill at the gym with my arms and legs bare and my cute 5inch lined running shorts for all to see is exhilerating.

      Thanks for sharing.
      Happy walking!
      -joanne

      • #604546

        You know it Joanne! My shorts are 5″ also and I love that they show off plenty of my best female attribute. 🙂

    • #604529

      Congratulations!!!!

      Sharing your first baby steps remember our first steps out and encourages others.

      My first baby steps….I put the garbage out dressed…lol

      Alanna

       

      • #604551

        Such a baby step you took Alanna but it’s no less of an important one!  I’m very happy to share my baby step here, yes let it encourage others.

    • #604535
      Stephanie Flowers
      Ambassador

      Certainly a wonderful feeling indeed,  congratulations.. 🌷

    • #604578
      Gillian
      Lady

      Great to hear your first time out went so well.

      I haven’t been out much. My first time was aged 17 in the dead of night. I twisted my ankle falling of my wedges!! But luckily I was never caught.

      I’ve been out a few times since usually a walk round the block at night or a short drive.

       

       

    • #604596

      Igo to a cd gay bar in Boston one nigh t I offered a cd Kathy a ride home I said let me go change remove wig shoes and put on jogging pants over skit she said no and made me do the walk of shame back to car heels and all after I dropped her I had to drive home dressed I was so carful did want to get pulled over looking fem with male id
      Love you peace Jennifer

    • #604598
      Liara Wolfe
      Duchess

      Happy for you.

      Hugs, Liara

    • #605426
      Diana W
      Lady

      Congratulations on taking what was a pretty significant baby step.  I’m glad it went so well for you.

Viewing 11 reply threads
  • The forum ‘Personal Crossdressing Stories’ is closed to new topics and replies.
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?