My Full Weekend as Crystal: Lessons Learned and a Rebirth

Crystal Tyler is a crossdresser from the Chicago area who’s constantly exploring and looking for ways to “up her game.” She is a real-life Miss Fisher/Nancy Drew with a BS in Criminal Justice. When she is not exposing insurance fraud or depriving someone’s ex-spouse of their alimony, she enjoys her female time. We now join Crystal as she prepares for her first full weekend en femme.

On Thursday, my adventure began. First was a haircut so my wigs would fit better, then a brow wax. I have to say, this was probably the worst brow wax I ever received. I was afraid of what would happen if I asked the lady to correct it, so I lived with it. This was actually a blessing in disguise that I’ll get to later.

Next was picking up my bags which were already packed. I had two totes and two garment bags. Was this overkill? Of course, it was! Looking back, I could have brought half the stuff I did. I recently received a bunch of new clothes I had not had the chance to try on, so all of those came, as did the stuff I planned to wear. I brought some casual clothes like tops, a pair of jeans, and a pair of denim shorts. For shoes, I had a pair of pink Sketchers, a pair of black ballet flats (my new fav pair of shoes), and two pairs of chunk heel sandals, one black and one tan. I also brought a bra in each color I own and way too many pairs of panties.

LESSON LEARNED ON CLOTHING

Don’t bring half of your wardrobe with you. It is completely unnecessary. When I went out, I was wearing the jeans or the shorts. The evening gowns were tried on and that was it, back in the closet they went. I wore two different sexy outfits for play time and didn’t wear high heels out of the room. No woman goes to the store wearing 5-inch stilettos and a silk, full length evening gown. Part of the fun of dressing is looking sexy and glamorous, but to pass in the “real world”, clothes like these will make you stick out like a sore thumb. I have some pieces of clothing that I will be getting rid of and I will be looking to expand my casual wardrobe.

I checked into the hotel, unpacked, and got ready for my date. You might have seen me tagged in the photos. It was a HOT time for sure! I had not been a blonde in ages, and it is a look I will likely be pulling out from the drawer.

The next day, the dreaded “day job” came to haunt me. I spent the morning and the previous evening taking care of sudden last-minute work. No fun at all! During that time, I checked my schedule and realized that my nail appointment was for 12:30 pm, NOT 1:30 pm! I rushed to get ready, wearing a white striped top, long denim shorts, my new black chunk heel sandals, and a summer floppy hat. I needed a bit of makeup and thought a simple day time look with some blue eye shadow would be nice. One problem. I only had a brown pallet and a neon pallet.

So now was my first time shopping during this trip. I wore my big sunglasses and headed over to Target. All I needed was a simple 3 color pallet with blue. That should be easy. Hell no! There was NONE to be found! I ended up getting the Eye Tattoo eye shadow sticks. I’ve seen the ads for them and they look great. Word of warning: DO NOT BUY THIS CRAP! Remember the really cheap crayons that restaurants would give out so you could color when waiting for your food as a kid? Remember how much they actually sucked, and they were so waxy that the color looked like shit? That is the Eye Tattoo eye shadow. REALLY waxy stuff. I was stuck so I did the best I could and was off to my appointments.

Bonnie was a blast for the mani/pedi! She was recommended to me by Rori at Transformations. The 2 ½ hours spent n the chair and at her table was just too much fun! She was totally friendly, open, and accepting. I went with a classic red look on my fingers and toes. The only downside was that I developed a blister from walking in the new shoes. I wish there was some way to eliminate this problem. I mean this is the same damn thing that happens with hiking boots!

Next was a makeup session with the wonderful and amazing Rori. Any girl that wants to learn makeup, GO TO RORI! She will have you looking beautiful, natural, and passable and is VERY reasonably priced. She went with a smokey eye look using white, platinum, blue and black, a slight cat eye, AMAZING lashes that were wider and fanned at the outside. She asked if I wanted the wig or the lips to be the “cherry on top. I told her that I always put on my wig, then applied my lips, so she did the same. First, she brushed out my wig and this was a lesson in itself. After she put it on me, she did my lips with cherry red and. . .

I WAS IN HEAVEN! I could NOT believe how amazing I looked! The look was so amazing, so feminine, and so perfect! I damn near wanted to cry! THIS was how I ALWAYS wanted to look! Rori was kind enough to give me a container of the lip stain as a gift, then we took photos for her and some to send to Bonnie who had requested some. Rori asked me if it would be okay for her to use her pictures for promotion and advertising. I told her she would plaster me on a billboard if she wanted! I had NEVER had THIS level of confidence! Ladies, go to Transformations By Rori in Arlington Heights, it is SO worth it!

Now I was on clouds with my confidence and my new look. After watching Rori, I felt sure I could pull this look in the future. I had to test this look and what better place than a packed Walmart on a Friday evening? I needed some stuff for the gangbang, so I went right on in the store, no hat or sunglasses to hide behind. I walked right through the parking lot to the doors, never getting a second, or even a first glance or the “turn the head away” from people. Inside, I went and used the washroom, passing a couple women walking out. Again, not a second glance. Next, I walked across the store, head held high, hips with that gentle feminine sway and accentuated by my hip pads (cheapest foam pads on Amazon, a can’t miss and they’re great), and over to the birth control aisle. I grabbed a box of condoms, a couple tubes of lube, and two packs of wipes. Then it was back across the store to the self-checkout. Never once was I clocked. Back out to the car, my arms swaying, purse over my shoulder, next to a woman who happened to be parked next to me, still not clocked. I needed cigarettes and Red Bull and picked those up. A door was held open and the man said, “There you go, ma’am” and I made my purchase. My voice got a slight double take when I asked for smokes, but nothing major. I went back to the hotel, strolled through the lobby with a confidence I did not have the day before, and got ready for the party

Next time: Lesson Learned on Passing/Makeup

Tags: crossdressing, featured, Out & About, passing

Category: crossdressing