Memories of Pinkfest 2017 — A Girl’s First Time Out in Daylight

Pinkfest 2017: My first time at Pinkfest — also my first time day-walking, so a huge boost to my confidence. Hope you enjoy this rather detailed account of a day that was very special to me. By the way, if you’re interested in the 2019 Pinkfest schedule, you can find it here. Here are my thoughts regarding my first time out en femme during the day.

The day started like most — got the kids up, fed and off to school. Got home, jumped in the shower, and then a nice close shave. All of my Julie ‘equipment’ had been packed into a small carry-on suitcase the day before, so I was just about ready to go by 9 a.m. My plan was to leave by 9:30 a.m., get to my changing location by 10, hour and half for makeup and outfit, and we would make it to the restaurant by noon. Since I was a little ahead of schedule, I offered my wife a back massage. We had discussed my plans a few days earlier, so I figured it would be a good idea to leave the house on a high note.

My Host

While I dress at home, I have yet to enter or exit our high rise apartment building en femme — I’m not out to the kids, so I probably shouldn’t bring things too close to home. The bottom line is that I needed a place to change early in the morning and luckily I found Valerie, a most generous and trusting soul. She’s from out of town and was renting an AirBnB room and convinced the owner to allow me to construct at her place. When I arrived I met the owner and the other guests, of course in drab. By the time I finished getting my full Julie on, they were all gone, which was a bit of a disappointment, cuz I missed out on what I hoped would be a few comments like ‘I can’t believe you’re the same person!’ 

Flats and skinny jeans.

The Outfit

Since this was a daytime event it called for a casual outfit, shopping was in order. I already had a good pair of skinny jeans and some nice flats, but didn’t have the right top. I started at Nordstrom’s Rack — almost got a really nice white top with black piping. Luckily, I tried it on and discovered that white is not good for us girls with big shoulders. Then I went to Burlington, found two tops and was checked out by a trans girl. She asked “Are these for your. . .” I cut her off. No, those are for me. I’m going out to lunch next week. Do you think those sparkles are too much for lunch? She said that sparkles are always good. It was such a pleasant exchange.

Unfortunately, when I got home, I discovered that sparkles are not good for all occasions and both tops were a disaster. The next day I went to Target and found the top in the pictures, basically the mirror image of the one I almost got at N-Rack. 

The Girly Problem

Two days before the lunch I started feeling that the outfit I picked just wasn’t girly enough and I kinda felt like just a dude in skinny jeans. I was thinking maybe I should switch to a skirt with black tights (but all my skirts were too tight for blending) or maybe ditch the flats and wear some heels. My online pal Michelle was great and suggested I stick with the flats and get some big lashes and french tip nails, both of which would never let me forget my girlieness. So, I stopped at my local CVS, got both and figured I was good to go.

Later that night I met some of the Pinkfest girls at Big Chicks. I was in drab, so it was less fun for me, but definitely a good time. I told them about my girly problem and they encouraged the heels solution. Valerie even offered to wear heels that day — in solidarity. (Did I tell you how awesome she is?! She ended up wearing skinny jeans also, with bright pink heels and matching top and lipstick — she looked incredible.) The next day, I did another dry run and found that my nude heels went perfectly with that outfit — gave a good feminine posture without being over the top and would never let me forget I was in girl mode. It’s a good thing I decided on the heels, cuz due to time constraints I never got the nails out of the box and gave up on the lashes after 15 minutes of trying (There was a time when I could put those things on with almost no effort, I guess they’re not like riding a bike and require constant practice.)

Deconstruction Plan

So, my original thought was just lunch. However, after corresponding with Valerie it became clear that to do so would mean that she would have to accompany me back to her place, wait for me to deconstruct and then travel another half hour to get back to the activities. She offered to do that, but I of course couldn’t accept in good conscience. So, plan B was for me to deconstruct at the wine tasting. (The owner of the wine shop is trans.) The obvious downside is that I would need to bring my little carry-on suitcase with me the whole day. So, I ordered an Uber from Valerie’s place, which of course passed us up, cuz the driver was not looking for a girl named Julie, but a dude named ****. Once in the Uber we engaged the driver, an older African American gentlemen, in some conversation. Fairly quickly he became disinterested in how we were dressed, cuz Valerie started talking about her skydiving experiences.

Lunch

At lunch I met Annie and Michelle for the first time along with the incomparable Laura, who I had met at Big Chicks. She has the greatest dry sense of humor. We finished lunch at one and then had to figure out what to do until 2:30 — the meeting time of the next event, dessert at a trans owned bakery. I took the extra time to grab a smoke outside, which of course had the bonus of my being seen by more of the locals. (During this time, I was slowly discovering that I’m quite the attention diva). While out on the sidewalk, the store window gave me my first full length reflection of the day. “Look’n good! Really work’n it with those heels. Makeup looks good and the volume and color of my favorite wig is why it’s my favorite wig.” Yes, feel’n like quite the diva — might need to tone that down a bit — could get me in trouble. 

The Neighborhood

Given the time between events, Valerie, Michelle and I decide to do a little shopping. Now this neighborhood is rather trendy — not touristy like Michigan Avenue nor classy like River North, but kind of a nonconformist hip type of area — it’s Boystown adjacent and known for having numerous goth and fetish shops. So the fact that three crossdressers would be walking down the street is not shocking.

So the hour and a half was filled by visiting a number of local shops, starting with a year-round costume store where I tried on a couple of used dresses — my first time trying on dresses at any store. Every sales associate at every store was totally friendly and maybe a little extra enthusiastic to see the three of us walking in. Really an ideal location for my first daytime excursion.

The Walk

Okay — this is my favorite part. I’m so glad I decided to go with the heels. Cuz, I was really starting to feel the girly walk. You know what I’m talking about — the imaginary straight line that you aim your feet for, the one that gives your hips that little sway. Girls I tell you I had it goin’ on. Adding to that I had a cute purse on my arm, which put my hand out there with a dainty bend. What’s more, I had that little carry-on suitcase in tow the whole time. The combination of the three (girly walk in heels, dainty look of the purse on my bent arm and finally the little suitcase trailing behind me) made me feel like the girlieist girl on the planet. One of those first time experiences that I will not to soon forget. 

My First Admirer

So the bakery had really delicious pastries, but was facing southwest and had only windows. As you might expect, heat is this girl’s kryptonite and that bakery was like the crossing the desert scene in Lawrence of Arabia. To escape the heat I went out for another smoke, on the side of the building and under the shade of a tree. There was a side door where I caught my reflection and, just for fun, struck a few poses. Looking back to the street I noticed a man noticing me and driving slowly. I gave a friendly wave and he drove on. I had actually been doing that the whole afternoon — if anyone made eye contact I would say hi, of course in my guy voice, which didn’t really surprise anyone. About half an hour later, Valerie noticed Laura across the street and walking past the bakery. So, I jumped up, went outside and called for her (any excuse to get out of that furnace). She turned and then I noticed that that guy was back, just sitting there is his car. As Laura approached, he said something to me that I couldn’t make out. So I stepped closer and he said “You look like a fun person. Lemme pull over over there and we can talk.” Not knowing what to say I came up with ‘I’m not that much fun’ turned and walked back into the bakery. Laura thought that this was the funniest thing ever and proceeded to tease me for the next 5 minutes. I took it in stride and figured I should be a bit more careful about who I’m waving to, especially that close to Boystown and 20 feet from being under the L tracks. 

My Feet and My Second Admirer

While in the bakery I decide to take off my shoes, just for a quick breather, and notice blood on my toes (the ones next to my pinky toes). I was not wearing hose of any kind, which I figured was what anyone else would wear with such an outfit. While my feet didn’t hurt from the height of the heels, there must have been some rubbing on my bare feet. This was actually a good thing, cuz it gave me a good excuse to suggest we leave the Burning Man heat of the bakery and head to the air conditioned (evil) Target to pick up some peds. Just as we approach the Target entrance there was a guy asking us for a cigarette. Just as we were waving him off, he notices that we were not regular girls and he says something to me, but we were in the store before he could finish. We quickly find the hosiery rack and I pick out my first pair of peds (never needed them before). I look up from the rack and the guy from outside is standing right in front of me. He says “I’ll buy you anything you could ever want.” I’m like ‘No, not interested.’ He persists. I get frustrated, raise my voice and say “YOU KNOW I’M A DUDE RIGHT!” He kinda nods with a facial expression that says “Yeah I know, that’s why I’m here.” I backup into the main aisle and start looking around for a manager. He notices this and finally gives up and disappears. Amazingly, I’m not really shaken (more flattered than anything else, which is probably not a good thing), and go back to the business of making my purchase and getting those peds on my feet. 

Giving Up on Stubbornness

After leaving the Target, we again have a fair amount of time before we need to head out to the wine tasting. Michelle has been looking for a vinyl record store all day, so with a little Googling we find one and head out. Turns out to be about 8 blocks away. At the start Valerie says there’d be no shame in giving up on the heels, but I’m just not ready yet. About half way there, I feel that my strut is getting a bit less girly, which puts the nail in the coffin. As soon as we get to the record store, I open my little suitcase and change into the flats. It’s almost 5 p.m. so I feel good about making it that far, but immediately get that just-took-off-the -ski-boots-feeling and have no regrets on giving up. 

Cool, Quiet and Julie’s First Train Ride

While the girls are in the record store, I go to the restaurant next door and get a seat at one of the outside tables. The waitress is totally accepting and I enjoy a lemonade in the shade. Once Valerie and Michelle join, I ask if I have any lipstick left after a full day of dabbing. Rather than go to the bathroom to re-apply, I pull out a compact mirror — another first for me. Now rather than the sexy lipstick application that you’re imagining, my inexperience with a little mirror makes it more like a random dotting as I try not smear it all over my face, fearing that I’ll end up looking like Miranda Sings (Google her, she is hilarious).

On the way to the train station, a vintage dress in a store front window catches my eye and I suggest we stop and look in. Again, the sale people were just fabulous and eventually we made our way downstairs to check out the lingerie. One of the sales girls helped me pick out a new garter belt, while Michelle found a new camisole.

I was about to head upstairs to check out, when I felt something strange  . . . my wig cap suddenly lost its grip and snapped off my head. It’s under my wig so no one would notice, but if this has happened to you, you’ll know how disconcerting this can be. Luckily, we were still in the basement, out of street view, and I was able to take off my wig, fix things up, and in no time, I was back in business. If that had happened on the train it would have been a very uncomfortable 40 minute ride. The train ride (my first ride en femme) was actually uneventful. It was packed, but everyone was just trying to get home from work and, for the most part, didn’t even notice us. 

Deconstruction and My Third Admirer

Once at the wine bar, I decided that while I could deconstruct there it was not ideal. Then Michelle offered  the use of her hotel room. It was on my way home and on the way to the blues club she was going to, solo I might add. So, after dinner next door at R Public House, I got an Uber for the two of us. The train would have been cheaper, but I was done with long boring train rides for the day.

Just as we were walking into the hotel a homeless guy notices us and started showing some interest. We exchange some friendly words, and then Michelle and I head up. I quickly deconstruct (way better than the bathroom plan) and we are off — me home and Michelle to the blues club (actually not too far from my house). We’re about to pay to get on the train and I notice the homeless guy from in front of the hotel. I go up to him and say ‘Hey do you remember me . . . from a half hour ago?’ He’s at a total loss, but then notices Michelle (who’s still en femme) and his eyes get big and is like “holy . . . no f’n way!” I’m totally ecstatic from his reaction and enter the station with a big smile on my face. After a short train ride, I walk Michelle to the blues club, we share a big hug and I get home about 9:30. I’m totally exhausted and nearly pass out immediately. 

Final Thoughts

My big takeaway from the day? Definitely an enormous amount of fun. Definitely my confidence was growing by leaps and bounds. Definitely going to do it again (I did 3 days in 2018 and will do 4 in 2019). But on the other side, by the end of the day I was totally ready to deconstruct (actually another first for me), which tells me that any thoughts of going full time or being concerned that I might want to one day transition are more on the side of a fun fantasy and not really in my heart. Let me say it another way. At no point during the day did I feel like “Ah . . . this is what it’s like to be a woman.” Of course, for girls that have those feelings, I totally support you 100%, but in my case I never forgot that I was just me being me. The fun of the day was being able to be pretty, out on the streets, basically accepted by just about everyone and not having an ounce of guilt or shame. I’ll take that any day of the week.

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Tags: crossdressing, featured, Out & About

Category: Out & About