Crossdressing In Public

If reading all of this text isn’t your thing, I’ve included a “Takeaways” section at the end that just summarizes a few key points that I’ve learned from my experiences.

      For the longest time, the holy grail of my crossdressing escapades was dressing up in public. Back before my friends knew about Janna, the fear (and thrill) of potentially being recognized along with the freedom of finally being able to be her in person, in public, was really unmatched for me. Despite wanting to, dressing up in public just didn’t really fit my super shy personality. The juxtapositions didn’t end there, I was a boy that wanted to look like a girl, an extreme introvert that sought exhibition and an attention whore that hated standing out. Weirdly enough, I don’t think those traits are that rare for crossdressers and so I wanted to share my painfully slow experience and stories of how I became myself in public.

      I started crossdressing in high school. I remember the very first item of clothing I bought - a pair of lacy purple and lilac panties from Kohls. I remember it because it was the first thing I ever bought online, with a rebate card I got from Black Friday shopping. Thanks Fry’s. I vividly remember the fear I felt of worrying about what would happen if someone got to the package before I did, the relief when the package was actually in my hands and most of all the excitement of opening the package and being able to hold my very first pair of panties. A spotted black and white bra followed after, short shorts, more panties and by the summer before college I had amassed a small but very treasured set of clothes that I could call my girl closet. I bring this up because aside from one item, every single piece of clothing was bought online. I was not even brave enough to go into a physical store and buy girl clothes in person. I was that much of a coward. This combined with the anxiety of being caught and probably most importantly the fear of being judged meant that for the next four years I mostly enjoyed the hobby privately, from the comfort and safety of my own room.

Technically The First Time

      I say mostly, because technically, technically, I did dress in public once in high school. Senior year, we were split in groups and told to make a film on the books we read throughout the year. I naturally chose to work with my friends, and we ended up in a group of all guys. For the life of me, I cannot remember the plot of our film or even remotely what it was about, but I do remember that we discussed needing a female role. Obviously, no one wanted to play it and for a while we discussed what our alternatives were. At this point, I would like to say, I seized the opportunity and volunteered, but nope, I was way far too shy and far too insecure. Eventually, we just decided to take a trip to Party City and improvise our roles based on what costumes we could find (and afford). I knew that this was my last chance to volunteer, but boy did I take my time. While everyone else was checking out costumes, I was eyeing the wigs, the stockings, the girly stuff. Secretly of course, you know the quick walk you do, up and down the target aisle multiple times pretending to look for something, but really just sneaking glances at the forbidden items. Eventually we had mostly everything we needed and with no girl, the group was ready to write off the role. As we were checking out, I finally decided to man up (no pun intended) and volunteered. My best friend asked me if I was sure. Sure, it wasn’t a big deal. But of course it was, all the anxiety about being judged by the cashier, the fear of being judged by my friends and all of my classmates (including the girl who I had a crush on) who would inevitably see the film, all of that dread came up at once. But now was the time for action and so I acted. I picked up a pair of black stockings with matching black bows and then told my friends I would borrow the rest from an imaginary female friend.

      It’s hard to accurately reflect on whether I was being judged by my friends (remember this is high school). Was I able to play it off cool enough? I don’t know, because all I remember on the car ride back was the adrenaline rush. First, I picked up a really cute pair of stockings (my first of manyyy), but more significantly I had just confronted a myriad of my fears all at once and that was a big deal to 17-year-old me.

      Despite this accomplishment, at this point, I have yet to actually crossdress in public or even in front of anyone else. That came a few days later when we started filming the project. We met up at one of the guy’s house. With me I brought a subset of my secret stash. The stockings of course, a pair of very short shorts, a tee and for my own benefit, the lilac lacy panties. I left the bra at home because it was too much. The shorts and shirt is explainable and no one is going to see the panties, but a bra would be hard to explain. I remember scheming on how to get dressed to make it the least weird. Do I try bits and pieces on or just put it all on? Should I make jokes, what should I say? I tend to overthink situations, and this certainly was no different. Eventually, I just took everything into the guest bathroom and started putting each item on. I’m not going to be too humble about it, but figure wise, I really did look good. I’m fairly skinny today, but 17-year-old me was even skinnier, just as tall and with a way more feminine build. The additions of the stockings really accentuated my legs and from the neck down it was actually fairly convincing. Obviously without a wig and a boat load of makeup, I wasn’t going to trap anyone, but I was proud. I must’ve been too proud because I distinctively remember hearing through the bathroom door one of my friends asking where I had gone and that’s when I realized I had been checking myself out in the bathroom far too long. Taking one last look over to make sure everything that needed to be covered was covered, I readied myself and stepped out.

      I don’t remember if there was a brief moment of silence, but either way my friends were surprisingly impressed. They told me that much. Aside from the initial reaction, there wasn’t that much fanfare. No one made fun of me, called me names or much of anything, at least not to my face. I guess to them, I was just doing the group a favor and happened to have an unusually feminine figure. A photo of my exact outfit doesn’t exist anymore (and thankfully so), but it was somewhat similar to this (same shorts and stockings) just with an actual shirt.

      The days we spent “filming” for that project were honestly amazing. Nothing significant happened, but I got to spend most of it dressed up. Even if we weren’t filming, I stayed dressed up which was just altogether a difference experience. One of the nights we decided to go hang out in the neighborhood park, it was far too dark to film anything useful, but I went in my short shorts and my stockings and just got to hang out on the playground with my friends.

      The only scene from the project I have a recollection of was the first time I appeared dressed up. The shot had me walking down a flight of stairs only showing my legs as I descended the stairs until my full body was in view to for the surprise reveal. The only reason I remembered it was because when it was finally our turn to show the film, my head was thoroughly buried, face down, in my arms. With my friends, with a semi valid excuse, crossdressing was fun. In front of a bunch of less close classmates, on screen, at school, that just felt awkward. I think the reason boils down to when it comes to a boy wearing girl clothes, you can’t really half-ass it. Either you make absolutely no attempt to pass and play it off as a joke or you fully commit and blow it out of the water. Either way, you must be confident about it. And confident, I was not. The fact that the film was pretty garbage didn’t help either. Thankfully there were no real long-term ramifications, I wasn’t bullied because of it, nor did I really hear about it beyond the first few days. Luckily for me the only embarrassing result of the event was when the on again, off again boyfriend of the girl I had a crush on told me I had nice legs and was genuinely surprised at the reveal. Life just kind of went on.

Actually The First Time

      I don’t really consider stockings and shorts to be my first real outing. It was a sampling that scratched an itch, but it didn’t count, I mean Janna didn’t even exist back then. The real first came four years later during my senior year at college. My girl closet was way more than just a bag of a few items now thanks to very generous fans from across the world. I had made a small name for myself in the various online crossdressing communities on Reddit and Tumblr as a side-effect of trying to satisfy the exhibitionist side of me. And while it mostly had, my final frontier, the holy grail of dressing in public still eluded me. The perfect opportunity came again thanks to school.

      Halloween of 2014 fell on a Wednesday and the professor of my Automated Software Design courses told us that if we came dressed up in a Halloween costume on that Wednesday, we would get extra credit on our final semester grade. I’m embarrassed to admit it because usually I pride myself as being a very good student, but truth be told, I really needed the points because I had absolutely no idea what was going on in that course. Either way, extra credit is extra credit and I made the bold decision to go to class as Janna. The question was, what would I wear. At the time, my closet was, kindly put, more bedroom appropriate than public appropriate. The costumes probably even less so. My favorites were the maid and schoolgirl costumes, but there was no way I was going to wear those in public, let alone to class. On the more costume, less lingerie side, I had a couple of flight attendant outfits, sailor ones and a nurse one. I remember, the night before, I donned my makeup, picked out a normal wig and then tried each one of the costumes and took of a video of each outfit from every angle. If I was going to do this, I wasn’t going to half-ass it again. Eventually, I settled on the nurse costume with a button up shirt to cover up the low cut on the back, a black bra for some shape and white stockings with pink bows to wrap my legs. It was public appropriate, but just barely. Think Angela’s sexy nurse outfit during The Office’s $15,000 in savings coupon book costume contest.

      With the “what” question solved, I looked at the other logistical problem on how I was going to get to class. The Computer Science building was around a seven minute bike ride from my apartment, but biking in a short dress didn’t seem like the greatest of ideas. Neither though, was walking 20 minutes through campus dressed as a semi-slutty nurse. Eventually I decided to just wear boy clothes over the nurse outfit, bring the wig in my backpack and just get dressed in the bathroom near class. The makeup I would have to put on at home and just hope no one notices while I speed to school on my bike.

      I don’t remember being particularly nervous the day of. My class was at 2:00 PM and I had no commitments before then, so I got to take my time. Granted my makeup skills back then were elementary at best so time didn’t really help too much. Like the night before, I drew on my eyeliner, eyeshadow and my mascara. I debated if bras and panties would be a good idea, but eventually thought back to my high school experience, if I was going to commit, I might as well not half-ass it. Finally, I slipped into my nurse costume. To check the full outfit one last time, I threw on the wig. I wasn’t feeling too confident about it all. Dressing up in public is just so much different than dressing up in private in front of a mirror or camera. Even ignoring the whole “you’re in public now thing”, a crossdresser’s best friend is being able to control the camera angle and the lighting, but out in public, you lose all of that. However, at this point I would be late for class if I chickened out, so I put the wig back in the bag and into my backpack. My sweatpants went on over the dress and a jacket went over the top. At the last second, I decided to grab my sunglasses so I could pretend to stay in incognito mode just a little bit longer. Without any more excuses to procrastinate, I hopped on my bike and started the seven minute bike ride to school. I’m not sure why I was anxious about the commute. Everyone had a place to be and I certainly wasn’t going to garner a second glance from anyone. Unsurprisingly I made it into a bathroom stall next to class without any fanfare, yet my anxiety was at an all-time high and I was scared. I was scared that my classmates were going to think of me as a freak, I was scared that a nurse costume wasn’t the best idea and I was just generally scared to be Janna outside of my safe space for the first time. Running out of time, I stripped down, stored all my boy clothes in my backpack and put on the wig. Making sure no one else was in the bathroom, I stepped out of the stall and adjusted my outfit in front of the mirror. Like all significant events in one’s life, I snapped a picture to commemorate the milestone.

      Oddly enough, looking at myself in the bathroom mirror at school, I felt a little better about it all. While things were far from perfect (there are so many things I wish I could tell me younger self), I was satisfied. With just a few minutes left before class started, I went to push the bathroom door open and immediately ran into another student coming into the bathroom. I’m not sure who was more startled, me because I was having excellent luck avoiding people all the way until now or him for seeing someone dressed as a girl in the men’s bathroom. Honestly, it was probably him because he let out a surprised “Whoa” and the emotion I was experiencing can better be described as embarrassed than startled. I ducked my head and walked across the hallway into the classroom. Being a graduate level computer science class, there were about ten guys and one girl (I guess now two, hah!) students. The guys didn’t say anything to me which wasn’t really all that different from any normal day although I imagined some were staring. My female classmate however, did. She told me I was awesome (true story) and liked my look and even asked for a picture which I shyly obliged. With the boost to my ego, I sat down in my seat for the lecture. A couple of other students dressed up for extra credit, so I wasn’t entirely out of place, but it certainly was an interesting experience and definitely my first and only time going to class in girl mode. At the end of the semester, I ended up picking up an A- in the class and I would like to think crossdressing helped get me there.

Folsom, Pride and Sissies

      When people confide in me about their fears of dressing up in public, the one advice I have for them is the same every time. Find an event in your city where everyone is weird and go to it. For me, the event that finally got me comfortable in my own skin was Folsom Street Fair. For those unfamiliar with Folsom, it’s an annual San Francisco subculture street fair that largely revolves around BDSM and other kink. For one Sunday every year, multiple blocks within the heart of San Francisco are shut down for one of the largest public kink exhibitions in the world. While it’s not the weirdest thing I’ve seen in the city, it is probably the most unique. If this has piqued your interest, I encourage you to check it out especially if you happen to be in San Francisco. Folsom was the perfect event for me because my greatest fear when crossdressing in public is sticking out. Regardless of how far I’ve progressed in terms of accepting my oddities and quirks, when in public, all I want to do is blend it. It is a frankly contradicting want considering I’m usually dressed in short shorts and crop top with some unnaturally colorful wig to garner attention, but it’s what my mind desires. Fortunately, with Folsom, no matter what you wear or who you come as, you’re almost certainly not going to be out of place. And for me, that safe environment was exactly what I needed.

      My first Folsom Street fair was in 2016. I had just graduated college and was living across the bay in Oakland but had heard from various more seasoned San Franciscians that Folsom was worth checking out. I even convinced my then long-distance girlfriend, who was visiting me at the time, to come with me. If you’ve made it this far (and I do want to apologize for my ramblings), you’ll know I’m big on logistics planning. For an outfit, I picked my favorite black overall skater skirt, a white crop top that I had bought for the outing and a cute kitty ear head band. It was extremely vanilla and entirely not weird enough for Folsom, but hey, it was my first time. Then, how to get there. The thirteen blocks of the street fair was the safe zone, but I had to figure out how was I going to get there from Oakland. Looking back, I probably should have just gotten dressed, walked to the BART (Bay Area subway) station and walked to the fair, but I was inexperienced, naive and scared. Plus, for those not from the Bay Area, BART has a certain ill-gained reputation for not being the most ideal place to be. So, I decided on a plan that involved Ubering to a friend’s place in San Francisco, getting dressed at their place then Ubering to the fair. Simple. Some useful advice, when there is a large event going on in the city where multiple streets are shut down, don’t bother with driving or rideshares. The car ride that usually took 20 minutes, took over an hour and a half. By the time I got to my friend’s apartment, the street fair was winding down and I was honestly a little heart broken. Today was supposed to be my big day, Janna’s big day. Regardless, I started getting dressed and my girlfriend helped me do my makeup. 30 minutes later I was out in in public, in front of my friend’s apartment and for the second time that day, erroneously stepped into an Uber. The decision ended up costing even more time and by the time I got to the fair, there was only about an hour left.

      My first Folsom, was not amazing or everything I hoped it to be, but it was eye opening. For one whole hour, I got to walk around as Janna and just observe. I saw leased pups, I saw people being whipped, I saw a ton of naked people, both my girlfriend and I were propositioned for sexual activities, but most of all, I saw people who just didn’t give a fuck. Regardless of how weird they may have looked or how much the myriad of tourists were probably judging, they were having fun just being themselves. And I realized, I could (almost) be that person if I just stopped being so afraid. I will probably always worry about the judgement of my peers, but it clicked to me that the most important thing is just to aim to enjoy yourself. Be confident and unashamed of how you present yourself and learn to be comfortable being uncomfortable or you’ll never want to leave the safety of your own home. Those were my takeaways from that day. Actually implementing it would take quite a few more years and many more events.

      I went back to Folsom Street Fair in 2018 and again in 2019, having missed it in 2017 because of Splunk .conf (boooo). Honestly, I don’t think I ever figured out Folsom and I’m pretty sure there was a lot more to the Folsom weekend that I was missing, but I do know that each year I’ve grown more confident and more comfortable sharing who I was. I think my Folsom outfit choices over the years certainly showed that. Unfortunately, with the 2020 event being cancelled due to the global pandemic and me leaving the Bay Area this year, I will probably never get to figure it out.

      Aside from Folsom the other large event that helped me come out of my shell was San Francisco Pride. I don’t really have much too add regarding Pride aside from if events like Folsom aren’t your thing, Pride is definitely a lot easier to swallow (heh). The first time I went to SF Pride was also the first time that I publicly came out to my friends about my alter ego (that’s a topic for another day, this one has gone on far too long) and the most recent time I went, I got to go with my trans sister which made for a fun family bonding event.

      The downside of large events is of course if you are an introvert like me, making friends when everyone already seems to know someone is difficult. And that’s my second piece of advice for people that want to get out in public: find a community or at least friends that share this hobby that will go to things with you. Most of my crossdressing friends I happened to find on Discord, but meetups and munches like the monthly Crossdressing/Sissies Club in San Francisco are another great place to not only meet friends but also a place to dress up without fear. I remember the first time I went; I was living only a ten minute walk from the cafe where the meetup was hosted so I decided to walk there at 8:00 PM on a Wednesday night. I wasn’t sure what to expect at the meetup but I did want to flaunt a little bit, so I brought out my favorite outfit again: black skater dress, white crop top and a bubblegum wig. In addition, I had just picked up a fairly convincing, although all together unrealistically sized breast place that I wanted to show off as well. I’m an attention whore, what can I say. The specific month that I had picked also happened to be a clothing exchange event which if you’ve never been to one, is a wonderful idea. The reason I remember this was because I was so nervous about walking alone at night that I completely forgot to bring the bag of clothes that I wanted to donate until I was well on my way and then I had to walk all the way back to my apartment to grab it. The event itself is held at the Wicked Grounds cafe and is perfect if you need an outlet to dress up for a few hours. I think there were around 20 people that first time I went with a wide, diverse group. Some people passed, many didn’t, some were dressed, some weren’t, but it didn’t matter because the focus was just on having fun and sharing experiences. My favorite part about the meetup however was what happens after it ends. At 10:00, the group gets kicked out of Wicked Grounds and goes around the corner to the Kat Club for Bondage-a-Go-Go which is a kink club event that happens every Wednesday. If talking and sharing stories isn’t your thing, then hopefully drinking and dancing is. I think the highlight of all of my nights there was having a dollar bill stuffed in my skirt when I went up in the bird cage to dance. I would never cut it as a go-go dancer, but for one brief moment, I got to feel like one.

Festivals and Cons

      Originally I wanted to dedicate a section to Anime Conventions because of how important they were to me for getting used to crossdressing in public, but I realized the topic was so broad that I couldn’t cover it all here. So instead I’ll just say, I can’t think of many communities where crossdressing is more normalized than that of the cosplay community. The way I see it, crossdressing is just pretending to be someone that you want to be and that’s not so different than cosplaying. Give it a shot.

      Finally, if BSDM events, pride celebrations, kink munches nor weeb fests are your thing then music festivals might be. To be perfectly honest, I’ve left this as last because I still haven’t gone to a music festival in full girl mode yet. Not because I don’t want to or have been too scared to, but just the idea of being crammed together in a jumping crowd while wearing a wig and full makeup is just…bleh. My first time in semi-femboy mode was at a Seven Lion’s concert in San Francisco. At this point, all my friends already knew that I crossdressed so I figured it would be a fun opportunity to go in something different than just your normal “bro” raving attire. My friend helped me do my eye shadow, put on eyeliner and painted my nails. In hindsight I wish I had gone a little further because after I was all done, it looked like I had just gone for a K-Pop look. On the other hand, it was the first time my friends saw me kind of dressed up, so maybe it was a good idea to start small. Either way, I got a couple compliments from my friends and that edged me to go bolder next time.

      Coachella! Normally, because I’m so introverted, I’m not super into multi-day music festivals, but fortunately my friends are, and I was convinced to go to Coachella in 2019. Part of the fun for our group was deciding what outfits we wanted to do for each of the days. In term of vanilla guy outfits, unless you wanted to burn in the desert sun, the choices are pretty limited and, in my opinion, pretty boring. Instead for one of the days, I wanted to go in girl mode (or I guess more accurately femboy mode). Settling on an outfit was surprisingly difficult partially because of my indecisiveness and partially because of my lack of “normal” clothes. I even resorted to enlisting the help of my Instagram followers to help me decide (thank you!). Eventually I decided to go with a mesh crop hoodie, white shorts, a choker and fishnets stockings with my normal girl makeup minus a wig. Nothing groundbreaking happened that day, but it was a ton of fun attending a “normal” event with friends all dressed up. Music aside, I think the highlight of the day for me was when one of the event photographers asked me to pose for some photos. I was never able to find the photos online, but it was nice knowing someone appreciated my outfit. The only advice I would add is if you ever do decide to go to Coachella dressed up, I would not recommend camping. I only dressed up in girl mode the first day, so it wasn’t too bad, but I felt really sorry for all the girls in our group who had to do their makeup every day at our camp site.

Being Safe

      Fun and adventure aside, dressing up in public is not always smooth sailing and it would be remiss of me to not warn those that do decide to take the first step in dressing up in public that the occasional harassment is to expected. As much as I wish everyone was open-minded and kind, it’s just not true. The unfortunate truth is that a man dressing up as a woman or at least one that wears women clothes is still not generally socially accepted and many still find it weird. While the mass majority of people fall into the category of being encouraging, apathetic or at least willing to keep their judgement to themselves, there are a select few that will make their displeasure known. The first time it happened to me was on my way home from San Francisco Pride. After the parade was over and the festivities ended, I took the BART home still dressed in my bubble gum wig, all-too-short shorts and crop top. As I was walking home from the BART station, I made brief eye contact with a man on the sidewalk and immediately regretted it. The next words I heard from him were I know you're not really a girl, I know you're a man, don't try to pretend. Wanting to avoid further confrontation, I just kept walking and after one last remark from him, I finally got out of earshot. The fact that it happened right after Pride made it all the more hurtful. After a whole day of people being really supportive, the comments of one person brought me back down to earth again and reminded me that not everyone is going to be supportive of you when you stick out.

      Aside from off-hand comments, being in girl mode in public, especially at night has made me wary of being alone. Part of it could just be implied vulnerability, but there have been a few occasions where I’ve been heckled or approached for sexual acts coming out of clubs at night. Granted, I’m still six feet tall and wouldn’t consider myself an easy target so I’ve yet to feel truly afraid from just the words that have been thrown my way, but it has forced me to glimpse a little into what women probably have to experience on a more frequent basis. Either way, my point is just, be a little bit more careful and mindful of your surroundings when you’re no longer in a “safe space”.

Takeaways

      Through the course of writing this, my girlfriend has given me so much flak for writing what is basically an essay. For those of you who don’t feel like reading my ramblings and I sincerely don’t blame you if you don’t, there are a few short takeaways that I’ve learned from this decade long journey.

1. Perform a risk assessment. Every one needs to weigh the risk and gains when deciding if dressing up in public is worth it. Why do you want to dress in public? Are there adverse consequences if you are recognized? Is it safe?
2. Realize that very very few crossdressers pass in public. I know I certainly don’t. It’s important to embrace this going in and don’t let people who call you out on it let you down. You’re doing this for yourself, not anyone else.
3. Find an event where you won’t stick out to ease yourself into it. Pride events, crossdressing munches, anime conventions all work. Once you’re comfortable here, then expand out to more normal activities.
4. Make friends. Friends make going to events that much more fun and easy. Plus there is safety in numbers.
5. Be more careful. Expect the occasional harassment and just be extra wary of your surroundings. Obviously this depends entirely on where you are located. Few places in the world are as “safe” for crossdressing as San Francisco so while I can say I rarely felt threatened walking home from bars, the same is definitely not going to be true for everyone.
6. Don’t half-ass it. There’s no getting around the fact that a boy dressing up in girl clothes is a little bit weird. Own it and be confident.