Throughout my crossdressing journey, there is one thing that I’ve found to be of paramount importance above all other things. You might perhaps think makeup. Getting that particular issue right is certainly important. I for one use enough foundation to plaster the walls of a large warehouse. Maybe it’s choosing the correct wig. No one wants to look like Radagast the Brown wizard from Lord of the Rings.

For many, it will definitely be the clothes. If the old proverb “Clothes maketh the man” is true for the male species, I would suggest it’s even more so for those of us who crossdress. How many have purchased a dress online, one that looks absolutely gorgeous on the female model, only to be disappointed when tried on. Standing in front of a mirror you see what looks like something your great grandmother made out of some old curtains.

For some, it’ll be the footwear. Do I look better in boots or shoes?  Heels or flats?  I absolutely adore women’s shoes, high heels in particular.  I love the way heels make my legs look feminine by accentuating my calf muscles.  Of course, the downside to wearing high heels is that I can’t really walk normally in them. I either look as though I’ve had too many strawberry-lemonade vodkas or as if I’ve had a little accident in my white Dolce and Gabbana silk lace panties (Possibly as a result of too many strawberry lemonade vodkas).

Actually, for me personally, it’s none of the above. The single most important thing when it comes to my life as a crossdresser is…. PLANNING!!  Planning is everything. In my opinion, to get the most out of every crossdressing “Session,” it is vitally important that you plan ahead. With that pearl of wisdom ringing in your ears, I would like to regale you with a short, true story about one of my crossdressing experiences.

I had it in my head to take a trip to a local store called Trago Mills. A huge place selling most things you can think of. I could easily spend a lovely couple of hours there as Carina checking out everything from women’s clothes and shoes to the latest power tool accessories. I put my planning head-on and got to work, everything laid out in detail. From the makeup, wig, shoes, and clothes to wear to the date and time of the trip and the car park I would use when I got there.

The day came around and I was very excited. Up since 6 am, showered and shaved (which takes a while when you look like teen wolf’s dad.) I did my makeup, had my wig and clothes looking pretty good. I parked in exactly the place I had planned to. A short walk to the store entrance and a 10-minute wait before they opened—this was actually part of my plan. Queuing up with other people enabled me to judge whether I stood out or blended in.  Were they staring at me?  Were small children running back to their parents horrified at witnessing such an apparition? Was the elderly lady in front of me frowning because she thought I was disgusting or because she just hated queuing?  Did that security guard just smile at me because he liked the look of me, or was he just suffering from wind?  Hard to know, but I felt confident enough to continue my trip as the doors opened and people streamed in, well four of us actually ambled in.

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I was in a face mask, and I felt good. Part of me was slightly disappointed because I’d spent ages doing my makeup and now most of it was covered by a bloody face mask. I spent a wonderful 90 minutes or so looking at just about everything in the store, and then it happened! I knew I shouldn’t have had that 3rd cup of coffee before I left the house. I desperately needed to pee; what do I do?  I could make a mad dash back to the car and 20-minute drive home. I could use the lady’s toilets on site. I felt that I looked convincing, but there’s always that doubt.

The last thing one wants to hear is, “Excuse me sir, but would you mind coming with me please,” coming from a security guard. The last option was to use the gents’ toilets on site.  Again, I’d probably be in danger of incurring the wrath of the on-site security people. “Excuse me madam, but would you mind coming with me please.”  This is marginally better than the other option. A choice not really a choice would be to go outside and find a quiet spot, where I could just do what men are lucky enough to be able to do in situations like this—except for the CCTV cameras that Trago Mills have perched on every available vantage point.

I could just imagine the excitement in the security control room when they catch someone on CCTV doing something other than shoplifting, minor vandalism or letting their dog mess on the pavement.  So, I quickly weighed up my options, and decided on……. (Drum roll) ……. Using the women’s toilet.  I quickly marched to the nearest conveniences, luckily there was absolutely no one around. So, in I went.  Again, luckily there was no one in there.

The moral of this story is quite simple really gurls; no matter how meticulously you plan something there is always something else that you didn’t think of that could potentially ruin everything. Luckily for me the “To pee or not to pee” episode actually enhanced my little trip out. After all, not only did I spend a few wonderful hours as Carina, I used the ladies’ toilets as well.

Happy days!!!!  Oh, by the way,  I don’t actually own any white Dolce and Gabbana silk lace panties……they’re far too expensive.

More Articles by Carina Cross

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    Edwina Sissykins
    9 days ago

    I have thought about being discreetly fingered and penetrated and fantasize about my husband having all my dresses modified with a vertical opening running over my bottom in the middle of my ass cheeks so he could stand behind me and discreetly penetrate me from behind with his penis and also insert any objects he wants to and my dress would still appear to be normal. Also a horizontal slit 6 inches wide at the waistband so he can finger me in public discreetly.

    Carla Roberts
    8 days ago

    When I first began going out in public, almost fifteen years ago, it was part of a closed event where I felt safe to use the restroom appropriate for my presentation. Eventually, after stepping out in more public areas, my confidence increased to the point where I felt pretty comfortable in women’s restrooms, but I was careful to avoid crowded areas, entering and leaving as discretely as possible. So with my confidence intact, I felt much more comfortable, to the point that I was not so careful about my restroom visits. So, as fate would have it, I entered what… Read more »

    Last edited 8 days ago by Carla Roberts
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