Halloween Evening in Full Display

Hi everyone, it’s been a while since I last posted here… so let me correct that! This is a story I’m currently writing and sharing on my Tumblr. My storytelling skills aren’t great, and I don’t put in much effort either; I simply want to share my experience as I recall it. I don’t proofread or anything like that—I just write the way I speak, as if telling the tale to a friend. Heads up: this is going to be long!

Halloween evening part 1 - Preparation As a European guy, I never really got into Halloween. As someone who crossdresses, I’ve always lacked the courage to dress up in front of others for costume parties or during the holiday. Usually, the go-to outfit for teenage boys and young guys is often that poorly executed, slutty girl look. A lot of dudes show up with a pink wig, a short skirt, and a tank top that’s two sizes too small, revealing bra straps stretched to their limit. And naturally, they pair these outfits with regular men’s shoes… But I’ve always wanted to dress properly, making it look nice and believable. You know how when you try to cosplay as Batman or a cowboy, you do your best to get the outfit perfect? Well, for some reason, when men crossdress, we seem to enjoy looking bad about it and laughing at ourselves. My fear of dressing up too well for a party—worrying people might suspect I don’t wear pantyhose and walk in (low) heels all the time—pushed me toward other costume options and often made me dread those events. Moving abroad and growing older helped me realize that I enjoy dressing up and going to parties with friends without being judged, and it’s high time to show off and have fun without worrying about being discovered. Last year, I tried attending a Halloween party as a girl, but ended up looking like a stereotypical magician… I was disappointed that I didn’t quite manage the look I wanted. Having the excuse of public exposure—more importantly, being exposed specifically to my friends—made it easier. This time, Goddess and I planned to go out dressed up. She loves parading me around when I’m looking girly and enjoys helping me overcome my fear of public eyes. I really enjoy nice sunny days on our balcony during spring while wearing my shiny pantyhose with the neighbors’ windows quite close:) It’s such a thrill! Anyway, this outing was different from all my previous walks. I used to go out occasionally, maybe once a year or so. I would dress up and head somewhere dark, walking for about 5 minutes, hiding my heels as much as possible while wearing male clothes on top of my feminine outfit. But this time, we planned for me to go into the city fully dressed up. For those few days leading up to Halloween, I was nervous, thinking about it and wanting to back out. I felt aroused yet scared on the actual day and tried hard to cancel, but she was determined to make us have fun. So in the evening, around 10:30 pm, I started getting ready: thick black pantyhose that kept me warm while still revealing my skin; a short black and grey dress (just above the knee) covering a nice, slightly shiny, light grey body with long sleeves and a collar. To complete the look, I put on my black leather knee-high boots with 4” heels. For my face, I applied red lipstick and searched for my good wig but couldn’t find it, so we went with the ugly one instead, brushed it up, and there I was, all ready for a little stroll through the busy city center streets. Almost midnight when we’re both ready to step out. She pulls off looking like a respectable macho guy quite well, wearing nice pants, a shirt, and my jacket. She applied some makeup to “grow” a beard on her face, and I put on my long coat before leaving the flat. My heart started racing as soon as I felt the cold air from the corridor sliding over my pantyhose… Hearing my heels click against the floor also increased my heartbeat, but there was no turning back now. I wanted to do this, she did too, and we were just going to walk through a few streets before heading home. Waiting for the lift, I couldn’t stop thinking about how aroused I felt and how happy I was to be able to share this with her. To be continued…

You can read the story on my Tumblr as well (and follow me if you like): I’ll post updates regularly depending on the feedback I receive;) Edit: maybe that should go in the “true story” section?