Thank you to anyone who read the introduction to my experience, found here:
any comments or feedback is greatly welcomed!
I made my way up the metal stairs, my bag slung over my shoulder, every step i took being followed by the people in the bar, watching me from behind their drinks, a couple of the crossdressers on the sofa whispered to eachother and one even pointed at me, their hushed voices punctuated by giggles. I keep my head slightly down, focusing on each stair as I climbed up towards the next level, trying to resist the urge to turn around and flee out of the pub.
“This is your last chance to run” I thought to myself, pausing at the top of the stairs. A door to the right of me had a piece of paper stuck to it, “dressing area” crudely scrawled across it. I sigh, another heavy, troubled sound, before placing my hand on the handle, and turned and pushed it open. My eyes adjust to the light coming in from the window, it’s a lot brighter up here, and after being blinded for a couple of seconds I manage to focus on the room before me. Theres a dozen or so little tables with mirrors standing on them, a room divider runs along the room, separating the dressing area from a staff kitchen, the faint smell of grease is overpowered by the smell of perfume, a small stereo is pumping out a Madonna song and there’s 7 or 8 other people in the room, all in various states of dress and undress, makeup half applied and feminine clothing flung all over the place. A youngish looking guy flashes me a smile as he combs a black bob wig in his hands, another older queen says hi to me whilst tucking his balls into a thong 2 sizes too small. I loiter at the doorway for a moment or two, unsure of what to do or where to go. A tall girl over in the corner is applying someone else’s makeup, a sign behind her tells me she does this for a fee, and her name is Pearl.
“Are you going to be doing your own makeup darling?” She calls over to me, looking me up and down with a barely concealed smirk on her face, clearly everyone here knows everyone else, and I seem to stick out like a sore thumb.
“N.. no I’m fine… I…. I’ll do myself, thanks” manage to sputter out, before swiftly sitting down at a table as far away from everyone else as I can, and proceed to take my stuff out of my bag. I start by taking all my makeup out and arranging it on the table, mascara, eyeliner and shadow on one side, concealer, foundation, highlighter, blush and contour pallette in the middle, lipstick, lip liner on the other side, my brushes and sponges spread out in front. I remove my wig from its netting, placing it carefully over the wooden prong on the back of my chair, before unpacking my dress and heels. I leave my condoms, butt plug, lube and extra panties in my bag hidden out of site for now.
I kick off my converses, before deciding to take my shirt off first, my heart beating in my chest as I unbutton it, slowly exposing the soft red lace of my bra hidden underneath, my freshly shaved body soft and smooth under the heavy fabric of the plaid shirt. I shimmy the shift off my shoulders and scoop up my dress, throwing it over my head and sliding my arms through the cap sleeves, pulling the floaty fabric down over my bra and down over my butt. I then undo my jeans and slip them off, exposing my stocking clad legs, hairless and moisturised underneath the sheer nylon. I hastily bundle up my guy clothes and stuff them into the duffel bag. I sit down upon the chair and look at the man I see, sat there in a dress, gawping awkwardly at his own features. I close my eyes and tell myself, “there’s no going back now”.
This is my happy place, sitting infront of a mirror, my face the canvas, my makeup my artistic equipment. I open my eyes again, and reach for my first tools. I apply my concealer and foundation, using my favourite sponges, before slowly applying contour across my face, sculpting my cheeks into a womanly curve, narrowing and softening my nose, pinching in my forehead and rounding off my chin and jawbone. I then take the highlighter, focusing on the top of my cheekbones, above my eyes, the middle and tip of my nose and under my lips, feminising my face and defining my features. I plaster over my eyebrows before redrawing them on, soft, thin and gently curved, letting my mind wander as I work at my creation, redrawing myself into my own idea of an attractive woman, thinking about what I am about to do, the thrill of being in a public place whilst dressed, and a sex club no less! I get that familiar twitch in my panties, and suddenly feel self conscious about being locked in a place like this, is anyone else here in chastity? What will they make of it? Will I even get to a stage where people will find out?
My thoughts are suddenly snapped away from as a petite brunette with a sheer top and black leather micro skirt approaches me.
“Hey hun, I don’t recognise you, is it your first time here?”
“Yes it is” I squeak
“I’m Nancy, me and Bob my husband run this party, he’s on the door downstairs, if theres anything you need, come find one of us and we’ll help you out ok?” She smiled, a kind, warm smile, and it soothed me immediately.
“Have fun today, and don’t do anything you don’t want to, ok?” She said to me quietly, casting a look over at a couple of the more rowdy queens getting ready over by the window.
“Ok Nancy, thank you” I replied.
I turned back to my mirror, deciding to turn my attention to my eyes, I choose a metallic silver Shadow and compliment it with heavy mascara, a winged eye line and a dash of silvery white glitter across the top of each lid. I choose a bright red lip stain and lip pencil, slowly drawing an exaggerated version of my lips, making them look plump and fuller than they actually are, arching my Cupid’s bow up more than usual, and applying the stain heavily to both lips, before using a clear gloss over the top to give me full blown “blowjob lips” as I like to call them.
I study my face in the mirror, my flawless complexion, the slightly over the top womanly features, the crisp lines of my eyes and lips, but something is missing. I grab my wig, a silvery grey wig with dark brown roots, the ends of the hair falling in long loose waves, and pull it over my head, fixing it in place, then brush any loose ends into place.
There she is! Felicity, my womanly alter ego, finally stares back at me through the mirror. I feel my apprehension fade away, replaced by confidence and self assurance, I look good, and I know it. I apply some women’s deodorant and spray a lot of perfume on, paying close attention to my neck, wrists and a couple of spritzes between my legs. I reach down into my bag and retrieve my purse and clutch bag, I transfer my phone and my money into them, alongside some mints, a few condoms, some more lipstick to reapply if needed, and a small bottle of lube. My hands graze my plug, still nestled in the bottom of my bag, my extra panties wrapped around it. I cast a look over the room and see a toilet sign over in the opposite corner to the entrance. My excitement rises, and the mixture of my new found confidence, the rum from earlier and my horniness leads me to the cubicle in the toilets within a couple of moments.
I lock the door behind me, and hike up my dress, before pulling my panties down to my ankles. I grab my plug, the metal cold to the touch, the pink jewel affixed to it sparkling in the light emanating from the sconce above my head. I place it in my mouth, warming it up, as I squirt some lube on my fingers and proceed to circle my tight hole, letting out a small gasp as I penetrate myself, first one finger, then two, working them in and out of myself, gently relaxing my entrance as I suckle on my plug. I go for a third, whimpering slightly as I force myself more open, my little cock squished against the confines of my cage, before extracting the plug out of my mouth and pressing it against my ass. It pops in without too much resistance, the wide stem holds me open slightly, the bulbous head giving me a nice full feeling, gently pressing against my prostate. I remove my panties, a red thong that matches my bra, and shove them into my handbag. I decide to grab my other pair, a lace set of open crotch panties in black, they fit snugly over my hips and ass, the opening allowing my cage to be free and my plug to be readily accessible. I unlock the cubicle and step back out into the bathroom, touch up my lipstick that smudged slightly on my plug, and with a grin and a wink to my own reflection, sashay out and back into the dressing area.
I make my way back down the metal stairs, taking great care not to trip in my mega heels, before slowly walking across the bar to the other side of the building, where a slightly heavy set man with mane of grey hair and beard to match was sitting infront of a door marked “Sweet Wednesday”. I catch the barman staring, as was the guy in the suit. In fact, everyone seemed to be staring, the crossdressers on the sofa weren’t whispering anymore, they all just sat and gawked at me, but now I wasn’t awkward and uncomfortable, know I’m Felicity, and I’m loving the attention!
Source: reddit.com/r/gonewildstories/comments/hmwx3o/sweet_wednesday_the_preparation_mt