Orginally posted this in r/genderotica as u/reusable_throwaway69. I’m a novice writer so criticism is much appreciated.
#The Help
I walked through a white empty space. “Where am I?” I thought. Looking around I saw nothing but white light as far as my eyes would allow. “Hello?” I shouted. “Anyone here?”. No response. I walked around, this time the sound of my sneakers on the hard floor was replaced with the soft clack of high heels. I turned around looking for the source, only to stumble and fall. Looking at my feet I saw they were encased in thigh high boot heels. Sitting up I went to undo them, only to have my torso be stiff as a board. The air was sucked out of my chest, I could only breath shallow short breaths. Looking down for the cause my vision was obstructed by my chest. My ample, D cupped, corset enclosed chest. I jumped to my feet, and started to run, feeling the swish of my many petticoats encasing my thighs down to my knees. “Where did those come from!?” I exclaimed. I started screaming for help, as my hair grew out and a ribbon tied it back into a neat pony tail, swishing behind my head. “Help!” “What’s happening!?” and then I was silenced. Something filled my mouth and muffled my voice. “MMMPH, MM MM MMMMF!” my tongue felt a rubber penis jammed into my opening. I collapsed on the floor sobbing mutely into my now manicured hands, as my black petticoats fell around me. I slowly left my dream, and entered reality.
I regained consciousness slowly. Drifting out of my apparent coma into a state of mental semi presence I tried to recall any memories that might reveal where I was, who I was, and how I got here. “I am… I am… … Jeremy! That’s it Jeremy, I’m 23… graduate… marathoner… “ My memories of myself and the rest of my life came to me slowly at first and then all at once. I was a college graduate, unemployed, in danger of losing my apartment, and rapidly losing friends to marriage. I could at least take comfort in knowing that my memories had returned, this felt like me.
The events that led to my current state were proving more difficult to recall. I was in a bar, with an old friend… no I had made a new friend, a woman! Oh she was a bombshell, how could I forget her? Long wavy blonde hair, aggressive red dress, hourglass figure, she had it all. Now what did she want with me? Oh right, someone to vent to. Figures, most women overlook me.
We had had a few drinks, I remember it so clearly now. “Men are pigs, did you know that?” “Funny, I don’t feel like a pig” I chuckled “Ha ha. I mean the men I’ve been with” “How bad was it?” “Bad enough I had to go looking around for the prenup we signed”
I seemed to be doing all right as her dumpster for emotional baggage, where did it go wrong? Did it go wrong? I think I just drank too much. No no, I only had those two beers, and the one cocktail she brought. Did I hurt myself? Couldn’t have been her boyfriend, not after such a recent divorce, did she do it? Oh no, it’s coming back to me. Oh I wish I could forget this part.
“Well the easiest part of your life is behind you, what now?” “Easiest part of my life?” “Being a housewife, not having to work, lounging, watching tv” “You think being a housewife is easy?” “Well it certainly isn’t hard!” I laughed “I’ve been busting my ass the working world and I’m just barely hanging on” “One day of being a housewife in my life would be the hardest day in your life” “Ha, even if I could walk a mile in your shoes they’d be the most comfortable shoes I’ve ever worn” “Oh we’ll see about that. But first I need another drink, let me get the next round” “Can’t wait”
She returned with the drinks as I was preparing my opening statements. Why am I such an insensitive ass? Trying to convince a woman that her life has been a cakewalk weeks after her bitter divorce? She should’ve have slapped me, or worse.
“Here you go. A toast?” “A toast” “To new perspectives” We sipped, and then my memory fizzled.
Blurs, spills, slurred words and then nothing. THE COCKTAIL! It’s all so obvious, why would she drug me? Oh no oh no oh no. Terrible things rushed into my mind. The jolt of realization was enough to knock me out of my semi conscious state into a fully conscious yet uncomfortable state.
My eyes blinked open and noticed two things immediately. The first was that this was not a room I recognized, the second was that my eyelashes were much longer than usual. I hoped this was a residual effect of the drug, I was wrong. My clothes felt soft and tight, my chest heavy. My feet arched into an uncomfortable position, and my earlobes were in sharp pain. My mouth was stiff and sore, and my ass had a fullness I had never felt before.
I sat up quickly, feeling two soft thumps against my back and I was greeted by the reflection of a woman in the mirror at the edge of my bed. I scanned the room looking for her, feeling two soft thumps on myself behind wherever I was looking. Going back to the mirror I noticed she was staring right at me.
She was sitting on the bed mirroring every motion I made. It couldn’t be me, this was some cruel trick. I rose to my feet stumbling at the edge of the bed, looking down I found the cause. Looking in the mirror I was reminded of it. My growing suspicion became my horrible realization! Standing up and steadying myself I got a good long look at myself.
My hair was jet black, and in thick pigtail braids that extended to my mid back. My mouth covered by a panel gag with thin straps that disappeared under my bangs and a harness that attached to the leather collar under my thick turtleneck. My eyes were smoky with mascara, and my eyelashes long enough to bat. Feather earrings hung from me earlobes, tickling my neck.
I was wearing a knit sweater dress with a hem just above my knees. It was grey with thick cream stripes around my ample bosom, and buttocks, that had intricate black patterns printed on the stripes. I had black cable knit stockings that disappeared under the hem and grey chunky heeled ankle boots that kept me stumbling.
By the time I had examined myself, I had already had enough. I began pulling off my turtleneck sweater dress, only to have it get stuck on my neck and choke me. I felt a leather collar around my neck, and rolled up the turtleneck to see not only was it sewn into the fabric, but it was locked tightly on me with a tiny heart shaped padlock. Feeling around my waist I felt a similar leather, but not as tight allowing for gentle curves around my waist, and a tiny heart shaped padlock hanging out of my dress in the back of my waist, securing the leather waist belt in place.
Rolling up my hem, I examined my groin. From the thighs to my belly button I was encased by and elastic white fabric with thick pads in the hips, and the buttocks, that stretched from under the thigh high stockings, where they were sewn to them, to where the leather waist belt was under my dress. It connected to the waist belt by belt loops which interlocked with the loops on the inside of the dress holding onto my waist belt. I didn’t even bother trying to remove the ankle boots, which had a small heart shaped padlock hanging off the side of each on the outside of my ankle, I knew futility when I saw it.
I grabbed my wig by the pigtails and pulled with all my might, only to pull my gag into the back of my throat and fall back on the bed. The wig was fastened quite securely to the top of the harness on my panel gag, which was locked to the collar encased in my knit turtleneck.
Realizing I was defeated, I arose to look at myself once more, the C cupped, hourglass shaped, sweater dressed, smokey eyed, girl. It would seem my captor had left one more surprise for me, as my involuntary arousal at my own sight was also greeted by a dull pain, followed by a feeling of frustration. Rolling up my hem, and looking down, the soft knit of my turtleneck tickling my chin, I examined my crotch. Finding a small tab, I yanked it, which pulled down a velcro flap right where pant zippers would be. Inside I found my swelling manhood, struggling against the steel confines of a locked chastity cage. This knitted prison was here to stay, I turned for the door, feeling the soft thumps of my braids on my back, and stumbled towards it.
Steadying myself on the wall I felt the heavy jiggle of my bosom with every clumsy step, however the C cup sized lumps were attached it definitely wasn’t with a bra. Even with the stumble and the jiggle, my ass made an almost involuntary wiggle with every step, its strange fullness being the cause. I struggled towards the door, my soft prison hobbling me, my feather earrings tickling me, and my heels humiliating me. “This can’t be happening” I thought.
Source: reddit.com/r/Erotica/comments/745cli/story_about_a_young_man_locked_in_a_feminine