Disclaimer: If you are offended by strong transgender themes, medium-intensity BDSM situations, gay, straight, bisexual, and lesbian sex, any of a multitude of other fetishes, or occasional scenes of violence (non-sexual), then please stop reading now. Otherwise, proceed on...
This story is a work of fiction. Some elements are based on true occurances, but reality takes a backseat to fantasy as it is in most fiction. The characters in this story live in a world where you don't need to worry about pregnancy or STDs; however, we do. So please, be responsible and use protection during sex. Let's stop the spread of STDs, one safe session at a time. :)
Send feedback to mootinmexico@gmail.com if you liked/hated it.
"Okay, then, Erica, let's take a look at you!"
I turned around and gazed into the mirror, taken aback by the beauty of the new self that stared back at me. It was funny to see how dramatic a change I could go through in just one week, the male identity I had held for so long erased in a matter of days. I certainly wasn't complaining, though! My new self was as cute and feminine as I'd always envisioned: over the front of a maroon-and-white maid's uniform hung two cherry-red pigtails, in sharp contrast to the mop of decidedly Irish orange-red hair that had been there at the start of the week. My boxy horn-rims were replaced with thin gold wire-frames, my usually rough skin now delicate and silky, and my body now permanently removed of the faintest trace of body hair. I beamed happily. "You're amazing, Lucy. Thank you so much for letting me take this job!" Lucy, my new boss, chuckled lightheartedly. "Heh, you don't have to thank me when you're gonna make me so much money. We don't get many girls at this company as cute as you. let alone sissy-boys..." She paused for a moment to examine my face, my clothes, and my body, making sure that every detail of my appearance would be suitable for the job ahead. I had to be perfect for the client, after all. "You know, I don't think the maid's outfit will be best for this job... Perhaps if we put you in something simpler..."
I suppose it's best to explain just how I managed to get to this moment in time, and the circumstances I took this job under. My birth certainly didn't indicate the radical path in life I'd be taking; I was born Eric Young to two rabidly Catholic Irish parents in New York, a couple that might seem more in place at the turn of the 20th century than the time when I was born. My father was an auto-mechanic, a brash, hyper-masculine man who held the stereotypical Irish aggressiveness, if not the stereotypical affinity for drink. My mother was a quiet woman, who seemed eternally absorbed in the typical drudgery of housework. They were always kind and never abusive or cruel, but they carried with them an emotional distance which they kept everyone, including the other and their only 'son', apart with. I recall playing often in my room, with Legos or action figures(or dolls, when I could get my hands on them from the girls in the apartment across from us.) In school, I tended not to fit in and spent most of my school career with a extremely tight-knit group of friends whom have lasted me to this day. I was always smaller than other boys, and even now I'm only 5'6" and 130 pounds. I wasn't particularly promiscuous in high school; I was active with both men and women but my shyness usually inhibited me from having sex any more than once in a blue moon. Part of this shyness was derived from a guilt and shame I had built up over the years; for me, it was the norm to dress up as a woman on Saturday night after my parents had gone to bed, and go to Mass on Sunday at St. George's. It was extremely difficult to come to grips with my gender issues, especially when trying to keep up the image of a religious life. It was overcoming this shame which would perhaps bring me to live the way I later would.
I left home after high school, since my parents couldn't afford to send me to college. My friends went to community college, while I found a cheap apartment and shuffled between a few tedious jobs. The independence of this type of life opened my horizons considerably, however: I began to be less reticent and shy around others, and my reduced church attendance led me to begin enjoying my sex life. I soon discovered the enjoyment I derived from submission; but the sporadic game of chance that was searching for sex at the bar became tiresome, especially since I wasn't exactly alpha male material, the closest gay bars were more dedicated to bears than effeminate men like me, and I had never mustered the courage to introduce my transgender tendencies into my sex life. Life as a normal male was leading to ever-increasing sexual frustration for me, especially in light of the transgender desires I had kept secret from all but my closest friends. And this sexual frustration brought me one day to the company I would soon find myself the star employee of...
It all began innocently, or as innocent as it got for me on the weekends. Feeling particularly dirty, I made an appointment at my most-frequented underground fetish club, the Whip's Crack, with a rather popular Russian dominatrix, Mistress Katya. As I entered, my booth, I saw her in a leather corset, lace panties biker's cap, her black hair flowing over her back and her full red lips looking particularly beautiful. What I didn't expect, however, were the silk stockings, leather miniskirt, slutty-looking tube top, and black thong panties laying at her feet. She looked at me with the steely, commanding eyes she had during each of our sessions. The hostess locked the door behind me, leaving only my mistress and I in the red-lighted, metal-walled room. "I see tonight's pet has arrived on time. I've got a special game to play with you, slave." She pointed to the floor at the clothes at her feet and beckoned me over. "Put these on, now!" I nervously obliged, removing my street clothes and putting on the clothes, secretly savoring the feeling of the stockings going up my legs, the panties around my crotch, and the dirty feeling of the skirt and shirt. I felt like a whore, and I loved it. I felt my erection straining against my panties almost as soon as I had finished putting on my clothes. "Does my toy enjoy being dressed up like a slut?" I nodded obediently. "Yes, mistress... I love it." "Does my toy want to be treated like a slut, like the sissy girl he really is?" I nodded, this time more fervently. "Oh, yes! Please treat me like a slut!" She smiled wickedly and stood up to her full height of 6'1. She towered over me, her D-cup breasts almost spilling out of her corset. "Very well, then our slut will get on her knees and pay respect to her mistress." She pulled down the black lace, revealing a well-trimmed bush of black hair covering a beautiful, tight, pink pussy. She pushed me to my knees and grabbed a fistful of my hair, pushing my face into her pussy. My tongue was awash in her juices almost instantly; I savored its flavor as I drew it from her dripping hole and as I ran my tongue over her clit. "You fucking slut... Give me more tongue, dammit!" Her normally commanding voice shuddered as I laved her cunt with my salivating tongue. Her moans and sighs began to culminate in a loud, almost screaming orgasm, as my face was nearly drenched in her luscious juice. She pushed my head away from her thighs and stared down at me. "Wonderful job, slave.. Perhaps a reward is in order for a slut who does her job so well." She took a cock-ring hanging off a hook on the wall, pulled down my stockings and panties, and slid if over my straining cock. "And perhaps if you're really good, we'll even let you have release!" She stood me back up and gently kissed the tip of my erection. She licked gently around the head a few times, and took all six and a half inches into her throat. I cried out in pleasure. I had never been this aroused; already, I wanted desperately for the ring to be removed so that I could come. Her head slowly bobbed back and forth on my shaft as she ran her tongue up and down my head. "M-mistress... please, please let me cum!!" She looked up angrily at me and took her mouth off my cock. "Perhaps our slave needs to learn a lesson about patience!" She pushed me to the ground and straddled my hips. "Thirty minutes without complaining, slave, and perhaps if I feel generous I'll let you climax..." She slid downwards, taking the full length of my hard penis into her. She began slowly riding up and down on me, moaning softly as I pumped in and out. Already, my balls ached so badly I could die. She began to pick up speed, fucking me harder and harder as I counted down thirty minutes. I was in agony at the end of thirty minutes, and she had already cum twice when she looked down at me. "My pet... slide that ring off, now." I happily obliged, and as soon as I had pulled it off I sprayed my mistress with several long jets of semen as I cried out in pure euphoria. As my climax winded down, my mistress pulled me back up. "Now... my sluts needs to clean up the mess she has made. With her tongue." I weakly licked up the cum that was on her legs and her corset. A few moments passed as she pulled the women's clothing off me and pulled me to my feet. "Did the slave like his moment as a girl?" I nodded. "Does he want to keep doing it?" "Y-yes, mistress... I'd love to..." She grinned and handed me a card. Her voice immediately dropped from the commanding dominatrix voice to a normal, colloquial tone as I put my street clothes back on. "Call this number, and ask for Lucy. We need more cute shemales like you at our company." I looked down at the card. It said, simply, "Heaven Industries", with the number at the bottom. I thanked her and walked out.
I called the number the next morning, and got in touch with Lucy. She told me to come to the offices that afternoon, and that we could talk. When I got there, I noticed a clean, carpeted office that felt less like a place for slutty slave boy-girls and more like a dentist's office. A secretary sat behind a desk, typing idly at her PC. I approached her and leaned over the desk. "Um, hi, I'm Eric Young, here to see Lucy Pearlman?" She looked up and smiled. "Oh, hello Eric. We've been expecting you." She led me to Lucy's office, a large room with a huge window and papers strewn everywhere. Lucy beamed as she saw me. She was about five foot nine, and dressed a little less than conservatively. Her brunette hair was extremely long, going down almost to her waist and pulled back into a ponytail. She had fairly small but perky breasts. Not bad, I supposed. "So you must be Eric! Nice to meet you!" She stood up and shook my hand. "You're the one who's interested in a position here at Heaven Industries, right?" I nodded and shook her hand firmly. The secretary left the room and Lucy closed the blinds. I noticed an immediate change in her mannerisms as she shut the door. She sat down at her desk and folded her hands. "Okay, Eric. Let's be frank. Basically, we're a prostitution company, ever since prostitution was legalized in the US and most developed countries from 2008 to 2010. We have many different branches, straight men, straight women, shemales, gay males, lesbian females, bisexual males and females, doms, subs, and switches. Katya, however, tells me that you're most interested in being a transvestite?" I nodded. "Yes... I've always had a fascination for feminization and crossdressing." She grinned. "You know, we get a lot of requests for types like you... How flexible are you, sexually? Are you bisexual, straight, or gay?" "Bisexual." "Are you dom, sub, or switch?" "Um, I guess sub, although I could probably try domination if you needed me to." "What won't you do, sexually?" I laughed and thought for a second. "Um, I'm up for anything not involving a dog, shit, or death." She nodded and jotted down a few things on a form. "Very well... I'll need your signature here. This will be a ten-year contract. Are you sure you want this? Quitting will be a very difficult process if you sign." I signed, I didn't even have to think. I knew being a sissy slave was what I had wanted for years. "Very good, Mr. Young. Or, Ms. Young, soon enough... Come with me." I stood up and walked out with Lucy.
"How it works at Heaven Industries is on an appointment basis, sort of like a hairdresser's shop. We get requests for your kind from all over the world, so you'll probably be seeing the world when you're on call. You'll have to be extremely flexible, as well; you'll be receiving requests of all types, from dominatrixes seeking slaves, men looking for temporary fucktoys, lonely women looking for a friendly fuck, and any other sexual situation you can imagine. As you probably know, sexual laws are a lot less Puritanical than they used to be, but you have to report anything illegal that goes on when you're on duty. We're legally bound to protect our employees and our clients. Did you get all that?" I nodded. "Yeah, go on..." "Okay, so what we do for men like you is a process of feminization that usually takes about five to ten days. We'll make you over completely, remove all your body hair, treat your skin and make it soft and delicate, give you a more feminine hairstyle, and get you some more suitable clothing. You'll pretty much be living as a girl most of the time, so we have to make you convincing for the public eye." I smiled at the thought of being a girl all the time... I was liking this job more and more. "So, take off your clothes and let's go back to the office." I tried to do this with as little protest as possible, but randomly being commanded to take off my clothes was still rather odd to me. I obliged, however, and stood naked next to the desk. "Okay... so, Eric, bend over that desk, would you?" I turned around and bent over, spreading my legs apart slightly and resting my elbows on stacks of applications. She took my balls in her hands first, gently feeling their texture and size. "Hmm... good..." She then spread apart my asshole, which hurt slightly considering how little anal sex I'd received in my life. "I see... tight... but is it clean?" She leaned her head down and licked my sphincter, gently pushing her tongue into the passage. "Not too bad..." She then stood up and leaned over me, her breasts pressing against my back. She gently started to play with my nipples, gently leaning her head down and licking one while pinching the other. "Are you sensitive here?" I nodded fervently, my penis now becoming quite hard. She pulled away and kneeled down again. "Okay... You're big enough for the job, too. I think this will work out quite nicely." She put her hand around my shaft and started stroking gently. "Alright... Tell me when you're about to cum." Her thumb pressed into my head as she began to stroke faster and faster. She licked my balls and started sucking gently on them. For several minutes, I was in ecstasy under her expert hand and mouth. "I-I'm getting close, Lucy..." She nodded and, quite suddenly, pushed her finger into my ass. The shock of it sent me over the edge. She cupped the hand that had been stroking me and caught my cum in her hand, bringing it up to her lips. "Mm!! So sweet!" She stood up and offered the rest to me. I obediently drank it from her hand and smiled.
"Well, Eric, I think we can begin transforming you to your feminine self by tomorrow. Welcome to Heaven."
And that's where it all began...