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Chapter 3
by OathkeeperPath
what does Sebastian try, how does shaving go?
A cluster fuck, as normal.
Always being one to jump head first into any problem, no body wants to go feet first into the unknown, that's how you end up feeling the wood chipper. 'Another great life lesson from 20th Century Fox'.
Leaving Sebastian with a winning smile a quick "thanks man!" and left for the store.
It wasn't until I was half way there that I realized I was still in a dress, but having enough self awareness that going back may let me loss my momentum I pressed ahead, besides no one ever gained anything my being too scared to ignore the sunk cost fallacy.
I was contemplating the TEDx talk that I had watched over and over about the power of pushing through and keeping yourself in a positive mind set when a confused shop keeper at the 24 hr store asked "Do you need any help?... Sir?"
Standing in front of the razor section a look of profound concentration on my face in a ruffled dress, I must not have been a regular sight for her nightly work.
"Absolulty! What kind of razor is best for a woman? I'm trying to learn." Hopefully that clears up what ever questions she has about me.
"Is this for your Girlfriend or for you?" I guess it didn't clear anything up, lets try that again.
"For me, I'm trying to understand what it means to be a women, my roommate told me this would be the best way." Making a gesture at my current state of dress.
"_I don't get paid enough for this... _Well are you planning to shave everything or just your face?"
"My face? why?"
"Well while most women do grow hair all over like guys, its normally thinner and we'll shave it off a lot of the time anyway. So you might want to do that."
"Oh... then all over I guess, I really want to do this right."
"Then take these and you may want to try waxing next time if this is a long term thing." She hands me a combo pack of Venus razors and gel as she walks off.
"Long term..." the reality of just how much I might be committing to if my plan actual does work, but I shake those thoughts away as they sound like doubts in my own head, doubts are like fear and fear is the mind killer.
Checking out rattles my nerves a bit as I do my best to ignore the looks from the few other people in the store this late.
'I got worse looks from people when I was first trying to get in shape, so why does this make me feel... more ... I don't even know what, revealed, maybe?' I'll hunt down that feeling for the rest of the night, I can already tell. 'Like with all things, your emotions are just another thing you have to wrestle with for control and understanding.'
Life may be a constant fight for the next step but there is something soothing about any amount of progress.
I'm a little flustered when I get back and Sebastian is asleep, I was going to ask him how I should do this, I've never shaved my face fully, I've keep it trimmed and in a few different styles but never fully removed, let alone shaved my body. 'He always had a clean shaven face and I bet has had to shave for things in Theater.' was my train of though there, but whatever.
I grab my phone, left again because of a dress and purse that can't fit it, and head to the bathroom and turn on a YouTube video for background noise to and try to figure this out myself, these things can't be that much harder to use than the electric razor I use to trim.
An hour later and I'm done, covered in small cuts and in pain because I read the gel directions after I put it on, witch was a mistake becaue it was supposed to be put on before I shaved and definitely not on top of fresh cuts.
Lesson learned, I read the instructions and follow a link to their website that has tips on how to best use their product.
'Why did I always feel the need to try things before I learn what I'm doing!?' Is my self talk as I fall asleep in bed, cuts still burning a bit even after I got them to stop bleeding.
The whole next week I keep getting glances from Sebastian, 'clearly impressed that I went above and beyond', but he won't tell me what the plan for this weekend is besides whats hes already told me.
I don't end up seeing many of my old friend group now that I'm not trying to, but I still see a few cause I'm not avoiding them either, we really just didn't have that many overlaps in schedule, I didn't really realize how must effort we must all have been making to hang out that often. 'They might think I was avoiding them, the idea crossed my mind that they might be avoiding me but really that's not like us. Really they took the times I fell off the earth when I got serious about something pretty well each time I did it, this should hopefully be the same. Just need to make sure I don't ask her out when we do start hanging out again and everything should be fine, just need to show I'm her type now and let things be. If I'm right and this was the only thing stopping us from working than she may also want to be the one that asks...'
Hope springs eternal if we are willing to be open to the possibilities.
It was Saturday night again when I had to remind myself of that truth.
"Run that by me again?" I asked in disbelieving consternation, my voice pitching higher in disbelief.
Sebastian’s smirk was the kind of expression that could only mean disaster for me.
“You heard me,” he said, spinning his laptop around to show me a flyer for a drag queen contest happening that night at Club Three Dollar. Drag Night Extravaganza: Show Your Sass! it read, in bold, glittery font. “We’re going to this. You’re going to perform.”
I blinked at him. “You’re joking.”
“Absolutely not,” Sebastian said, his face way too serious for someone who was clearly enjoying this far too much. “You want to become more feminine, right? Well, what better way to explore that than going full drag queen?”
I stared at the flyer again. “That’s, like, the opposite of subtle. I was aiming for subtle.”
“You? Subtle? Really?,” he said, tossing a sequined bra and a ridiculously fluffy feather boa onto the bed. “If you can handle this, you’ll be able to handle anything. But if you want we can go with my original plan, I was going to have to go to a 'normal' club and see if you can get any numbers. Ready for that instead?”
“This feels more like you’re trying to screw with me, you're having too much fun messing with me.”
Sebastian put a hand on his heart, feigning offense. “Mess with you? No. Challenge you? Absolutely. Plus, it’s a great opportunity for you to really test your limits. Drag is all about confidence, and confidence is key.”
'Dad did always say all a man needed was confidence, fake it till you make it..'
I sighed, staring at the sparkly mess of accessories. “What am I even supposed to do? I can’t sing, and I definitely can’t dance.” I'll let him have his fun, as long as it was still helping me, it was a small price to pay, I guess.
“Lip sync, buddy. Just choose a song, sashay on stage, and commit. Trust me, no one cares if you can sing. It's all about attitude.” He pulled out a bag of makeup and what looked like a wig styled by a deranged Marie Antoinette. “I’ll even help you get ready. It’ll be fun!”
Keep moving forward or back out?
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Loving A Lesbian
Unrequited
You (Chris) fall in love with your best friend, sadly she does not feel the same way and things get awkward. When you find out its because she is into girl the same way you are it gives you an idea, to fix the friendship you broke, and at least get one date, you enlist the help of your college roommate to help you get feminine enough. Its not really any crazier than any of your other plans to be truthful. (Doing a RomCom this time, sexy scenes will still happen, its still me writing it after all,lol.)
- Tags
- Crossdressing, Crossdress, Trans, Confession, Romance, Comedy
Updated on Jan 20, 2025
by OathkeeperPath
Created on Sep 3, 2024
by OathkeeperPath
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