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.
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.
You could have used the disabled toilets (if any were available). They usually have no gender on them.
Hi Simone, thanks for you comment, and it’s an excellent point sweetie. My original article did include a sentence or 2 mentioning that the disabled toilets were engaged. In fact there sounded as though there was a small party going on in there. God only knows who was in there and what they were doing. I did wait 30 seconds or so, but when I heard someone from inside say “It’s my turn next" I decided to bite the bullet and use the ladies toilet instead. I had to cut this part out of my original article due to it… Read more »
I like the graphic you used. It succinctly summarizes the likely outcomes in some parts of the US. For my outings I have a loose plan. Confidence and resourcefulness do the rest.
Thanks Emily. Unfortunately it summarises the likely outcomes in some parts of the UK as well. I’m afraid “Confident" and “Resourceful" are 2 words that don’t spring to mind when I’m out and about as Carina. “Terrified and “Excited" are the 2 words that best describe how I feel on my little trips. But I am getting slightly more confident. One day I would love to be able to just go out as Carina, on a whim, with no planning. Thank you so much for taking the time to read my little article Emily, and for posting a comment, it’s… Read more »
You will get there Carina. Confidence will build as you work on your presentation and get out there. Eventually, all the planning will become routine. You won’t think about it. Kinda like when you’re getting ready to do something in guy mode.
Hugs, Emily
I certainly hope so Emily. Thank you for the encouraging words.
I am actually hoping to go to a local T girl social meeting this Friday (10th Sept). It’ll be the first time I’ve ever attended anything like this. One minute I’m filled with a sense of overwhelming excitement at the prospect of meeting and talking to other T girls like me. The next minute I’m engulfed by a feeling of total terror at the prospect of all the things that could go wrong. But I am determined to go. Wish me luck Emily
Hugs,
Carina xx
Hey Carina did you attend the local social? How did it go?
Hi Emily, Yes, I did attend, thanks for asking. It was almost a total disaster though. The meeting was in a village hall in a place called Clyst St George, but my car’s Sat Nav took me to the village hall in neighbouring Clyst St Mary, where the local Women’s Institute were having a meeting (I didn’t know this at the time though). I sat in my car, in the car park watching what I thought was one extremely convincing crossdresser after another enter the hall. At one stage 2 of them walked past my car close enough for me… Read more »
OMG that’s a great story! I laughed out loud. Brings new meaning to “Nav System Failure"! Glad it all worked out and you had a positive experience….and you handled the last minute surprise in your well laid plan!
Hi Emily,
Thank hun. Sometimes true stories are better than fiction. And you know, this was totally my fault, I can’t really blame the SAT NAV. I typed in “Clyst St" and the SAT NAV pre-empted what I was going to type next, and offered up “Clyst St Mary" as the top option, so I just selected it (the second option of “Clyst St George" is what I really should have chosen). I blame it on the fact that I wasn’t thinking too clearly due to being so nervous……..or maybe I’m just stupid .
Take care Emily,
Carina xx
I remember when I was at college in London in the 70s. I had a friend on the same course who lived in Soho as a result we often went there for meals and drinks. one day we were in a bar and I had to visit the toilet. As I went in I realised there was a lady in front of me. Confused I turned around , went out and checked the door. Sure enough it was the men’s so returning I was about to say excuse me madam I think you are in the wrong toilet when she… Read more »
Hi Lisa, You’re right there sweetie, times have certainly changed. Things that once shocked us (like your experience in Soho) are now deemed acceptable. And, in my opinion, that’s not a bad thing. The meaning of “Tolerance" and “Understanding" should be taught to everyone from an early age. A friend of mine informed me that there are plans to have a third option available when visiting public conveniences. Not sure how true this is, but apparently there’ll be a “Ladies", a “Gents" and a “Trans/Non Binary/Gender Fluid" etc etc. Actually, there are over 100 identified genders that currently exist. All… Read more »
Hi Carina,
Loved your account. I’ve been to Trago Mills, whilst on holiday a few years back so could picture your plight. I’ve been going outside since April but never on my own, yet. Despite this, my biggest concern is always the ladies toilets. It usually takes a few minutes of deliberation before I embark on a new toilet. Communal wash basins outside also cause me concern but I’m still here and still peeing. Good luck on your journey .
Carla x
Hi Carla, Thanks for taking the time to read my little article, glad you liked it. I think it’s brilliant that you’ve been going out since April, well done you . And, in my opinion, it doesn’t matter if you go out on your own or with someone else, it’s still a big step to take. Some T girls have told me that successfully using a ladies toilet is all a matter of confidence. Just walk on in, as if you’ve done it hundreds of times before, and it’s the most natural thing in the world. But that’s easier said… Read more »
I actually loved the part you made light of. Passing is everything! You crossed every proverbial tee, after the I’s were dotted. And realizing that you probably were dressed better than half the cis women there that day. So hitting the John at a less than peak time was most likely going to go smoothly as long as you weren’t required to speak, where your voice might crack. As a transgender woman who does do that much crossdressing e I am not known, I find these stories on cross dresser heaven exciting. I go to doctors appointments where I must… Read more »
Hi Cindy,
Thanks for taking the time to read my little article. You’ve actually hit the proverbial nail on the head there sweetie. No matter how good I think I look, I can’t disguise the voice. I have tried, but I end up sounding like the guys from Monty Python when they’re doing a sketch in drag. In other words…..bloody awful!!!!
Good luck on your trans journey Cindy
Stay safe.
Carina xx
I agree on the planning. For your issue described in your story one of my items I make sure to have is a large mouthed bottle in my vehicle. That way I always have a discreet option to relieve myself. It used to be you could easily find a spot to pee outside, but with cameras everywhere now it’s not as easy as it once was!
Hi Darcy, Thank you for taking the time to read my little article, and for taking the time to send me a message as well. As silly as this sounds, I’ve never actually thought of using a bottle. What a simple but brilliant idea. I will keep an appropriate sized bottle in my car from now on. Thanks Darcy. You’re absolutely right about “Big Brother" watching our every move these days. I live in a relatively small city in the UK (Plymouth), but there are CCTV cameras everywhere you go. We do have a very low crime rate here, so… Read more »
One thing I have found – if you go ahead like you belong there, no one stops you. Just go in, do your “business" – make sure to wash your hands, young lady – and leave. All with confidence. My first trip to The Ladies was with 2 girl friends. We were at a casino, and as we go up from the table, Sarah said she needed to go. Being women, we ALL went, but I did hesitate going in. Sarah grabbed me by the arm and lead me into the Holy Sanctuary. We all tended to business and left… Read more »
Usually the best plan is to walk in and act like you own the place. Don’t be discourteous or anything but really it is the correct place to be. I have always found women to be much more accepting of cross-dressing than men
Hi Samantha, I am working on increasing Carina’s confidence, but having said that, I’ve also been working on my lead guitar technique for the past 20 years………and I still suck!!!!!! . I think you’re right about women being more tolerant of cross-dressing than men. Except in my family unfortunately. My partner (who knows nothing about Carina) once told me that she thought crossdressers were “Disgusting". And my dear old mum once said that she thought crossdressers were “Not real men". Both would disown me if they ever found out about Carina. But I digress, lets get back to the issue… Read more »
I wish arrogance was that enough to make me a good guitar player. I am okay but I know a bunch of really excellent players. They have definitely humbled me. The way things started for me going out was that I formed relationships with some of the sales girls at the stores I frequented. Got to the point with a couple of them that I would give them a fashion show and they would critique the outfits on me help me to make choices I was happier with in the end. After a while I got used to being seen… Read more »
LOL, I hear you Samantha. I sometimes think my guitar playing has definitely improved, and then I go to a live gig, and realise I’m still at the bottom of the guitar playing food chain. You know what Samantha, I think that’s a really inspirational little story you’ve written there. Especially the last sentence; “I think we worry more than we need to." That should be the slogan that all crossdressers adopt. Having said that, I think I would have been extremely worried if my car nearly ran out of petrol in a rough neighbourhood. Remember hun, if you’re going… Read more »
Hi Julie, Thanks for taking the time to read my little article, and also for taking the time to send me a message. Ah, there’s that word that keeps cropping up……CONFIDENCE. And you know what Julie, you’re absolutely right. Confidence is the key. I like to think that I’m a fairly confident person, or should I say confident male. My problem at the moment is that my confidence goes AWOL when I’m out dressed as Carina. I am hoping that, with practice, patience and time, my confidence will grow, until I emerge butterfly like from my dark chrysalis. Um…….sorry about… Read more »
Hardly rubbish, Sweetie! The butterfly analogy is most appropriate for what we do.
You’re right Julie, it is very appropriate.
Just going back to the subject of confidence, the lovely Samantha Peders shared a wonderful little story with me in which she included the line “I think we worry more than we need to". Which would make a wonderful crossdressing slogan, don’t you think?
I can’t say enough how interesting is to me to read these articles and follow the forums. I see that crossdressing is a long learning curve and so it is for those who are friends with the community. I learn so much here and always find myself spending hours and hours reading the articles, comments and even the responses ahahaha
Hopefully people will be more open to this in the future and maybe having the chance to be exposed to/involved with the situations like the one we just read, it makes them to be more understanding.
Frannie
Hi Frannie,
Thanks for taking the time to read my little article, glad you found it interesting.
Anyone who cross-dresses certainly has a lot to learn. I’ve been cross-dressing for a long time, but I’m still learning new things. And I agree with you sweetie, the articles and forums here are great places to share and gather knowledge and experiences.
Thank goodness for the internet.
Take care Frannie,
Carina xx
My god its a long time since I’ve heard the name Trago Mills. I used to live in Plymouth 30 years ago. I know what you mean about planning, I do my best to get everything sorted but sods law usually finds a way of ruining my idea. I found myself standing next to my unsuspecting friend at Ikea in the queue for coffee. She was in front of me so I spent time looking in my bag and staring at my shoes. I had my glasses on which helped. Other than the wc quandary it sounded as if you… Read more »
Hi Helene, I love your name by the way. I have received a few comments about good old Trago Mills. It’s certainly not a place that immediately springs to mind when thinking about places to go on a cross-dressing adventure. it’s not shopping in Harrods or a night at the opera in Covent Garden. But we’re simple folk down here in the South West of England . Where in Plymouth did you used to live Helene? I was born and bred in the St Budeaux area, but have lived in Plympton for the last 30 years. I think you’d notice… Read more »
I have yet to go out in public en femme, but I know that if and when I do, there will need to be planning.. particularly with this political brewhaha about laws regarding restroom..aka the Bathroom Bills in various legislatures. My question is would it be wise to do the following right now, given coronavirus, regardless of the clothing you wear. I write this in a serious tone..not meant as a joke. Would be wise to wear diapers under your clothes, given coronavirus issues? Toilets often are not the cleanest places, and we want no one getting sick. I am… Read more »
Hi Rose,
I certainly take your point sweetie. I now keep an appropriately sized bottle in my car for any toilet emergencies, as suggested earlier in this discussion by the lovely Darcy Grigsby (thank you once again Darcy ). Which, in my opinion, is perhaps a more straightforward way of relieving oneself when needed.
Take Care Rose,
Carina xx