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In an earlier post over a year ago, I mentioned that I cross-dressed out in the wilderness in the mountains. Since then, there have been a few other instances where I cross-dressed in the wilderness of the mountains.
I just got back from cross-dressing in the streets of my city for the 1st time! (Technically that was the case when I first started typing this. It took about an hour and 30 minutes for me to finish typing this post up). I’ve been planning this for days. Last night I couldn’t sleep so I got on my bike, and went shopping at Walmart for a few random things like new shoes.
Since it was 3:50 in the morning there were hardly any customers there so it was easy but nerve-wracking to pull a pair of women’s sandals down from the shelf, put them in my reusable Walmart bag, and buy them at the check-out line (bought the reusable Walmart bag too. I got it specifically to hide feminine clothing from the view of other customers. That way they just see a bulge, and know that I have merchandise in there). Now I have everything I need to pass in public.
This night I got up at about 2:45am, got my cross dressing clothes out of the laundry room, got dressed into my female outfit except for the sandals, and wig which I put in my backpack. I put a pair of male jeans that can pass as gender neutral after dark from a distance, a gender-neutral T-shirt, and a gender neutral hoodie over my female clothes.
I stuffed my bra with less panties than usual in order to accomplish what I call the golden bust. It’s enough where if I find myself wearing my wig with this outfit there’s enough bust for me to pass as a women but if I don’t have the wig on it’ll look like a larger male chest. That combined with wearing a loosely fitted, gender neutral hoodie, keeping my distance from passing cars, and the fact that it’s dark outside. The rest of the panties were in my jeans pockets.
I got on my bike, and rode it up the street still in male mode. Than I realized that I forgot to shave my face. I can’t shave my arms, and legs because people in my college classes will notice but nobody driving by will notice unshaven arms, and legs in the dark. However, I still wanted my face shaven because my face is what passing drivers will see the most, and because I can get away with shaving that. I stood there with my phone with the camera on, and my bike light to check my facial hair, and whenever a car passed I just pretended to be taking selfies. There was too much facial hair so I went back to my apartment, shaved my face, and went back out on my bike.
I ascended a bridge going over the Interstate using the sidewalk. There’s a concrete barrier between the sidewalk, and the road. There’s also a concrete barrier between the sidewalk and the Interstate beneath the bridge. The bridges curvature, combined with the darkness combined with me laying myself and my bike down would render me invisible to anybody on the sidewalk even if they can see the point between the bridge’s top, and the slant connecting the top to the regular road down below. It’s just too dark, and too far off. Also, there’s hardly anyone out at about 3:05am.
I rode my bike to the top of the bridge going over the interstate using the sidewalk, and scanned both sides (forwards, and backwards) of the sidewalk to see if any pedestrians were coming. There were none, and I could see the sidewalk for long distance on either side. I laid my bike down, and laid down on the sidewalk. I took my male clothes off but it was somewhat slow because I was laying down on the cement, and because I couldn’t raise my arms too high or else they’d be above the cement walls that barricade me from the bridge’s road, and the interstate.
Fortunately most of the cars were on the interstate, and there were hardly any of them. If my arms were to accidently raise too high when they were passing which did happen a couple times, those drivers would have to look up to see it, and me being so high up with it being so dark with them driving so fast would make it nearly impossible for them to notice, and even if they were too see they can’t exactly pull over, and investigate it.
Now when a car passes over the bridge, I cannot afford to let them see anything because they are more likely to notice, and they could pull over after they cross the bridge, and look over. They could even stop right then and there because they won’t have other cars coming up from behind that they’ll hold up. Every time I heard a car on the freeway underneath coming I had to assume that there was a car ascending the bridge because the sound of high-speed freeway cars driving underneath will muffle the sound of any low-speed car ascending the bridge. I never saw light from a car on the bridge when cars on the freeway underneath passed but I can’t be too careful. So I finally got all of my male clothes off, and got my wig on. I was officially dressed as a woman.
I was still laying on the ground, and if I were to get up with a car approaching they’ll see someone rising up on the sidewalk which will look suspicious. I had to listen for a car to come but it had to happen when there was no car on the Interstate passing beneath in order to be sure that no car was coming. Then a car ascended the bridge. It was in the oncoming lane which meant more distance but it was still a little nerve wracking. I pressed my body up against the cement wall between the sidewalk, and the road. The car passed, and didn’t see a thing.
I listened a little more, and heard nothing so I finally got up. Looked both ways (forwards and backwards), and saw that no cars were coming (and could see for a long ways in both directions). I took the remaining panties out of my jeans pockets, and stuffed them in my bra with there being no cars on the Interstate beneath either.
Then a car ascended the bridge with me sitting on my bike in my female attire wig and all. I immediately pulled out my phone pretending to check something in order to have an excuse to stay there because my backpack, and male clothes were still laying on the sidewalk. I turned the brightness all the way down (which is a normal thing to do in the middle of the night), and positioned myself so that the phone wasn’t lighting up my face but didn’t look suspicious, and also in such a way that I could have my head tilted downwards, and away from the car but not enough to make it look like I was trying to hide my face from them.
The car passed. It’s official. For the 1st time ever, someone saw me dressed as a woman but fortunately they didn’t realize that I was a cross dresser because it was dark, that bridge is poorly lit, there was a little more than a whole car lane’s worth of distance between us, and my face was turned away from them enough. It was a little nerve wracking but it also felt cool that they saw me but didn’t realize that I’m really a guy.
Then there were cars on the Interstate beneath while I was putting my male clothes into my backpack but I didn’t care because only those going north would notice anything, and they would be too far away to know what I was really doing; they’d think that I had just stopped to get something out of my backpack, and was putting it back. Unfortunately I couldn’t get 1 of my male shoes to fit inside my backpack with the other shoe, and my male clothes even though I folded my male clothes up decently (Knew I should’ve brought the Dakine instead of the Ogio. Next time I’ll be sure to do that). I rode my bike with the male shoe that wouldn’t fit in my hand. Of course, I can’t hold it for the whole trip because that’ll look suspicous. Especially where it’s a heavy duty hiking shoe with me wearing sandals on while riding a bike. It makes more sense logically to wear the heavy-duty hiking shoe while riding my bike. Before taking off I knew that there was a thicket of tall grass near the bridge’s descent, with a wirefence. The grass makes it easy for the shoe to be concealed, there’s a fence so it’s not like people are going to walk over there anyways unless they go out of their way by walking around to do so which they would virtually have no reason to, and it’s the middle of the night so hardly anyone is out on the streets anyways with the vast majority of what few people are out and about in their cars instead of on foot or on bicycle.
So now I have to return to this particular spot to change back instead of using 1 of the other spots that I found for changing in public or else I’ll be stuck wearing either no shoes, un-matching shoes, or women’s sandals with male attire on. To be fair the sandals could look male from a distance in the dark but would rather just be wearing male shoes when I change back into male mode.
Rode my bike around the streets of my city! Surprisingly I did not feel nervous at all. Then again there were absolutely no cars in sight. Then the thought of a car coming made me ever so slightly nervous but the fact that it was dark combined with distance combined with them seeing me from the confines of a car reminded me that I would be passable as a woman to them. During the day this would not have worked at all because my face shape is too masculine, my shoulders too broad, and my arms and legs unshaven, and no make-up on my face.
Then there were a couple cars that did come, and they saw me but they didn’t know that I was really a man. I was a little nervous about it, and would slightly turn my head downwards, and away but only enough for it to look casual instead of like I’m trying to hide my face from them.
Continued to ride around, and made it to the rich neighborhood that I wanted to ride around in. The great thing about neighborhoods is that the streets are poorly lit, and there are even less cars. Also, rich neighborhoods are far less likely to have dangerous thugs than ghetto ones. Also, the streets are really wide making it way easier for me to put plenty of distance between myself, and any car that might pass me whereas in some neighborhoods the streets are narrow and passing cars would be too close to me, and for that to happen with them going too slow would get me spotted.
So I ride around the neighborhood, and it felt nice. It didn’t feel scary. I just felt free. Free to be out and about the streets of my city cross dressing instead of having to stay in my bedroom or be out in the mountains (although doing it out in the mountains certainly feels more liberating than doing it in my bedroom).
I had a few cars drive past me both in the oncoming lane, and from behind but nobody reacted to my presence which means that they really thought I was a woman. I even stopped, and played some Pokemon Go but had to put my phone in my boobs, and start moving as soon as there as a car coming because I do not want to be standing still while crossdressing when there’s a car coming.
So then I get cold. When I had gone out to get my laundry in male jeans, a male T-shirt, and my heavy duty hiking boots I was fine, but now I was wearing a thin shirt, a thin short skirt, and sandals that expose most of my feet. As a result, there was a lot of heat rushing out my feet, and hands. My feet, and hands were freezing, and the rest of my body was cold. If my hands and feet would’ve been only as cold as the rest of my body it wouldn’t’ve bothered me but with freezing feet, and freezing hands I needed to get back into male mode, and then get home.
I rode in pain back to the bridge going over the interstate but not the way I had come (in other words, I went in a loop). Before it had been fun being out here on my bike dressed up as a woman with my wig but now I just wanted to be done. I need to buy a feminine jacket but more importantly feminine gloves. Could easily get those at Walmart the same way I got my sandals there.
I rode past my apartment complex wanting to go inside, and warm up but couldn’t because even though there was a 98% chance that my roommates were asleep or at least in their rooms laying in bed, still don’t want to chance them seeing me cross-dressed. Returned to the bridge, and began to get dressed back into male mode but it was harder to because my hands were numb. Also, with it being 5:28am there were somewhat more cars out driving because the really early morning shift people were driving to work, and the graveyard shift people were driving home.
This also meant slightly more cars crossing the bridge. This made it harder to change because I had to freeze more. It also didn’t help that my hands were numb which made it harder to pulled my jeans on over the top of my skirt. Took my sandals off, and pulled my male shoe out of my backpack.
Then I realized that I forgot to check east for pedestrians which meant that one could be coming without me realizing. Even though there was less than a 1% chance that this was the case, and even then a slim chance that they would approach the top of the bridge, and see me before I had enough time to get fully changed, and all that.
As a result I just grabbed my hoodie, and yanked it on without bothering to get my T-shirt on or take my wig off. My wig ended up getting stuck inside the hoodie. I pulled some of the panties out. I listened for cars but didn’t hear any coming so I stood up, and put the panties, sandals, and male T-shirt in my backpack. Shoved my foot inside my shoe without bothering to take the time for socks. By then there was a car coming but I was also moving, and the cement wall between me, and them meant that they wouldn’t notice that I had a bear foot as long as I coasted with the pedal for my barefoot being lower. Walked around the fence with the grass thicket, retrieved my shoe, returned to the sidewalk, and put my barefoot in it. Then another car came, and saw me but they would’ve just though that I had stopped to retie my shoe because it had come loose, and was slipping as a result.
Despite having to end the public cross dressing session sooner than I planned it turned out to be a good thing that I ended it then because there were already slightly more cars driving around so staying out as long as I planned would’ve meant even more cars out driving around which would’ve made it even harder to change because there would’ve been more instances were I would’ve had to have froze. While riding back to my apartment at about 5:50am I noticed a morning jogger. Don’t want joggers out while I’m chaning on the brigde because even though it’s speed-walking pedestrian proof, and heavily jogger (at least 90%) resistant it’s not completely jogger resistant.
I returned to my apartment, put my female clothes in their suitcase, and spent the next about an hour and 30 minutes typing this post in order to share my story with you guys.
I did it again last night (early morning of Friday, April 26th, 2019), but it was a different experience.
This time I brought my Dakine backpack instead of the Ogio which allowed me to fit both shoes in my backpack along with my male clothes. When I was laying down on the sidewalk for the bridge going over the interstate, I forgot to put my wig on before standing back up. Obviously there were no cars coming because I would’ve been listening for it but there still could’ve been a car off in the distance, and if they had been no more than a block from approaching the bridge I would not have been able to put my wig on without them noticing nor drop back down without them noticing. Need to stay down until I get the wig on. Fortunately no one was there.
Instead of riding my bike around the top of that rich neighborhood up on the hill like I did before I rode around in multiple other neighborhoods. It was not as easy nor as peaceful as last time. There were several instances where I could’ve gotten spotted but didn’t because I did enough fast thinking.
In order to reach them, I had to ride east around my college campus. Some of the streets alongside it are better lit. Fortunately there were no cars coming but I was still nervous so I turned north onto a dark road, and then east onto a another dark road. Then I had to turn south onto a road that was less than a block away from the edge of my college campus but it was lit, and there was a car coming so I turned around going west onto the road that I was currently on. Then I came back out, and turned south onto the road leading back to the edge of my college campus.
I approached the brightly lit intersection but no one was there. Then there was a car coming up from behind! Crap! If they pass me while I’m crossing the intersection they’ll see my arm and leg hair, broader shoulders, and male-shaped legs! Book it! So I rushed across the intersection, and back into the dark before the car could pass me. Thought about riding west into my college campus but then I heard laughter over there (must’ve been students playing Pokemon Go. There’s a group of friends who like to play it on campus in the middle of the night). Turns out that car had ended up turning at the intersection.
I rode south into neighborhoods. Some of the streets were wider than others but none of them were too narrow. Saw a pedestrian on one of them. Technically it was on a main road going alongside the neighborhood. He was on the other side of the street, and that street was very wide and unlit so even though he turned his head, and glanced at me he would not have been able to tell that I’m really a guy.
I headed into some neighborhoods south of those neighborhoods. Then I rode on one of my city’s main street. Was trying to get to neighborhoods south of it. At first riding on the street was no sweat but then I realized that I was going to have to cross a brightly lit intersection, and even though there was only an occasional car on this road I could tell that it would be hard to cross it without there being a car there at the same time. I cannot have cars be that close to me under bright traffic, and street lights. As a result, I crossed the street, and used a side road to approach the intersection. But then the side road ran out, and I would have to cross Golden Corral’s parking lot which is also brightly lit. At least it was closed (obviously), and it meant enough distance between me, and any passing car to be far away enough (the distance can be less in the dark). Also heard the sound of employees in Golden Corral’s kitchen which was a little nerve wracking but they’re busy preparing stuff for morning.
I made it south of the Golden Corral Intersection. The road was a narrow 2-lane road with no shoulder other than several yards of dirt, and rocks. As soon as a car turned onto that road from behind me I immediately swerved quite a ways into those dirt and rocks (which I would’ve also done if I had been in male mode) but of course the car then turned onto another road into the neighborhood that I was trying to reach. Approached the foot of the mountain but there was someone in their garage with the door open. Normally I wouldn’t’ve cared but after 4 nerve-wracking situations I didn’t want to deal with it.
I rode through other parts of the neighborhood, and rode north back through each of the previous neighborhoods from this trip. Made it back to the bridge going over the interstate but still had time to be out, and about but not enough to venture far. The first time I had been out this long I was anxious to be done because I was freezing. This night it was warmer so that wasn’t an issue, and believe me I did not want to change into male mode, and go home.
I rode around the neighborhood just northwest of my college campus. Tried to cross the road with all the fast-food places, and gas stations but there was too much lighting, and a couple pedestrians with them being close enough to the intersection that they would spot me. Now if it weren’t for the lighting, their distance from the intersection would’ve been fine for me to cross it.
Had another nerve-wracking situation. Was approaching a neighborhood intersection with a bright street lamp. Then a car in the perpendicular road showed up. I immediately turned my head down, and right in order to avoid them seeing my face. Despite turning my head by a lot instead of turning my head at a subtle level I managed to make it look natural by making a sharp right turn onto that perpendicular road. Then the car sped away because they had been waiting on me. That was close.
I returned to the bridge going over the interstate at about 5:00am. I did not want to be done but knew that I must because at 5:45am there would be an early morning jogger who would come out, and only be a couple blocks from this bridge, and I don’t know if he would cross the bridge or not. There would also be other early morning joggers that would start to come out. I make it a priority to return to this bridge at about 5:00am in order to change back into male-mode before the early morning joggers come out. Sure, pedestrians can’t see me laying down on that bridge’s sidewalk when it’s dark until they reach the top but joggers can reach the top a lot sooner than walkers.
Stood there for a couple minutes looking out onto the interstate down below. Checked both sides of the bridge (forwards, and backwards) for pedestrians but there were none, and no cars coming either so I laid down. This time I had a lot of difficulty getting my hoodie back because I could get my head into the hoodie but couldn’t find the other end that my head was supposed to pop out of. Try doing that while your laying down, and can’t get up in order to avoid being seen and you’ll get nervous real fast. It also didn’t help that there were constantly cars driving on the interstate underneath the bridge so I couldn’t hear if there was a car ascending the bridge so I had to assume that there was, and stay down. Took the hoodie off, and tried again and succeeded.
Then my biggest fear came coming. There was someone ascending the bridge but they were on the sidewalk! Gasp! The light on their head gave it away. Now, if it had been a car or motorcycle on the road, I would’ve just had to keep laying down in order to avoid being seen. Same goes for someone on the sidewalk for the other side of the bridge. That wasn’t the case. It was someone on the same sidewalk as me and they were already ascending the bridge.
At that point I was already back in my male clothes except for my shoes, but my wig, and woman’s sandals were on the ground. Also still had fully blown boobs instead of the golden bust. I immediately said a quick prayer, and threw the wig, and woman’s sandals into my backpack. Began to shove my right foot into it’s shoe. Then the man was at the top of the bridge. If he asks what I’m doing (after all my bike was laying on the ground, my backpack was on the ground, and I was putting my shoes on) I’ll just say that I fell off the bike so I’m putting my shoes back on because they came off when it happened. There, that’ll work. Hopefully. Was hunched over while putting my left foot into my left shoe. That combined with a loose-gender neutral hoodie would be enough to keep him from noticing the bulge from my breasts. I lifted my bike up for him to pass which also required me to be hunched over. Thankfully he didn’t say anything when he passed me. He just continued his jog like nothing had happened.
I don’t know if that was my prayer being answered or if he was already the kind of person who didn’t care. Also, can’t tell if he found the behavior suspicious and didn’t say anything or if he just thought that I had just stopped to fix my shoe or something. Either way, that was way too close, and I will not be using that bridge to change between male, and female mode again. To be fair I did come up with a way to prevent the hoodie malfunction which would cause me to be able to get back into male mode faster, and therefore have more time to put things into my backpack, and get my male shoes on before a jogger comes but if I mess up on that again, or mess up on something else than I run the risk of having another really close call. Regardless of whether or not that jogger found my behavior suspicious, it’s one thing for him to see me like that once, but if he were to see me in that same state a 2nd time that would be more than enough for him to say something about it. Just no.
I’ll be cross dressing in public again tonight but I’m going to use a different hiding spot to get changed. There were 3 others that I already had in mind, but then I came up with 2 more. The purpose of making a lengthy post for each session so far it not to do this for every cross-dressing in public session. I did it for these 2 because the first one was about my first time doing this, and the 2nd one had nerve wracking situations, and 2 close calls with one of them being too close.
At first I thought it was annoying for him to have a headlight but looking back that is actually the reason I knew he was coming in the first place. Also, even though using the bridge to switch between the 2 gender modes is impractical, and tricky which is why it made me feel “cool, and stealthy” for doing it, it was also nerve wracking every time I did it. Especially when changing back into male mode because I have to put clothes on while I’m laying down pressed up against a wall instead of just taking them off.
1 of my other hiding places is like that too but still safer than the bridge going over the interstate, and I can stand up for the other 4 places which means that I’ll be able to switch between the 2 gender modes much more quickly which will make it safer even though it’ll take several more minutes to reach them. It’s worth it.
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