Being a control freak, not always a bad thing

This week I needed to go on a business trip to one of our seaside resort cities. This involved an overnight stay and I took the opportunity to get some Daniella time in. I made sure that my air tickets were booked in such a way to allow me this time, but I delegated the accommodation booking to AN Other.

My wife and I discussed outfits and I packed my bag. The suitcase was FULL and the only non-girly contents were a toothbrush, toothpaste, undies, socks and a shirt. I had decided I would wear one (casual) outfit to the beach and another more glam outfit to my dinner ‘date’. I therefore had 2 full outfits (including shoes and underwear) as well as all the ‘additional’ crossdressing kit (breasts, razors etc).

I felt fully prepared as I had all my makeup, my wig and a plan. What could go wrong?

Just before leaving for the airport I received my accommodation voucher. Oh dear! I realised it was not the large and anonymous Holiday Inn I had requested, but a small guest house. I was concerned but thought ‘not to worry, it will be fine’.

After my meetings I drove to the guest house. Disaster! It was intimate to say the least. My room was placed in such a position that I had to walk through most of the house and gaining access as well as getting out meant interacting with the 24 hour security guard who would only open the gate on positive identification. What to do? I briefly considered abandoning the plan but decided not to be deterred.

My original plan was that I would shower, shave, beautify, dress in my denim mini, pink tank top and sandals and go to the beach for a couple of hours. I had then planned on returning to my room and changing into my sequined skirt, black top and stilettos and then go to dinner with another crossdresser.

This plan was not going to work. I decided to do only the one outfit and to then put my work shirt and jeans over this. I opted for the more glamorous look (I like my heels). It was very hot and even though I had the air conditioning on full blast I was ‘glowing’ profusely whilst I put my make up on. I put my wig, handbag and shoes in my laptop bag, donned my jeans and work shirt, put on my male shoes and headed out. I hunched my shoulders to reduce the size of my boobs and headed straight for my car keeping my head bowed all the way. I tried very hard to keep my rings and false nails hidden as well.

I don’t know what the security guard thought, but he opened up for me and I drove to a quiet street where I slipped off the jeans and shirt and replaced my shoes with my gladiator sandals. I donned my wig and hoped that it was straight. It was very hard to tell how I looked using the cars rear view mirror!

I headed for the beach. Found some parking and paid the parking attendant in cash who ‘ma’amed’ me 2 or 3 times. I walked on to the promenade where I was definitely looked at a few times by a number of men. I think a few must have clocked me, but nothing was said and even their body language was ok.

I suddenly realised that not only was I a bit ‘glam’ for the beach (I knew I would be) but that as a ‘woman’ alone in South Africa I stood out! This was the first time I had been out alone, all other excursions have been with my wife, and I suddenly realised that in South Africa women do not walk around alone, not even to the beach. All the other women around were either with male partners or other women.

I stood out. Oh well there was nothing to be done… I walked around, enjoyed the breeze, it was still very hot and I was fearing a make up melt down. I took some photographs of the view and even two selfies. I walked up and down the promenade and then returned to my car.

I then drove into the city for my dinner ‘date’ with my Facebook friend. Despite some very poor service we had a nice time discussing clothing, make up, breast forms the crossdressing communities in our respective cities and a range of other subjects.

After dinner I stopped in at a local trans friendly gay club to see what was happening. The place was very quiet and after 15 minutes I decided to head back to the guest house as I had an obscenely early flight the next day.

I drove back, stopped off at the quiet street, removed my wig, earrings, and shoes, slipped on my jeans and shirt and put on my male shoes. I returned to the guest house. The security guard opened up and I again did my Quasimodo impression to get in doors.

No one in the house saw me and I made it into my room unmolested.


Major lesson learned: stay in control of all elements of your trip. If you want to dress you need to plan all the details yourself or you will get tripped up. Anyway no harm done and I had a blast, despite the heat and the accommodation surprise. It seems that you attract more attention alone than when with someone else, or maybe I was just more aware of the attention, who knows. I would do it again, but I would take more effort to blend at the beach and I would be more careful where I walked. Walking past the bar and the liquor store after being at the beach, was a bit nerve wracking and I certainly garnered some attention there. I also now have more time for the mess that seems to accumulate in women’s cars. The extra pair of shoes, spare make up (my handbag was too small) and other feminine paraphernalia certainly accumulates fast!


Add yours →

  1. I would definitely agree being a control freak does pay off indeed. But there is one thing that you did that you didn’t mention which also very important.

    Sometimes we cannot be in total control or we slip up, and in those situations the important things is DON’T PANIC. You could have abandon the Daniella time because of the slip up you where not in your usual comfort zone. But revising the plan and some hope (I imagine walking past that security guard would have been hard) you manage to rescue it 🙂 Also learned some things in the process so it goes better the next time 🙂

    I think you might have been more aware of the attention being alone. I know I can become hyper aware when alone myself. Maybe also being alone as a woman on the beach might have garner some extra attention also. So a combination of the two.

    But I am really happy that it turned out good for you and had a wonderful time despite the problems 🙂

    Liked by 2 people

  2. For a cross dresser it is essential to visualize, plan & level headed see ones environment up in your mind & as you walk through every second of the way. Than I bet Daniella thinks even while not cds-ing, just like a computer multitasking, since that’s how I think really really fast in my mind! Being a control freak for cross dressing is a requirement, otherwise people walk over while you aren’t telepathic & taking advantage! There are some tricks & tips for being a male cds’r yet using technology as telepathy mind control.


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