This story is a work of fiction. It's not real. None of it is.
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I kind of ran out of drive on this one, barely finishing it. I might update it some other time, but please enjoy it anyways.
I usually prefer to keep to myself and avoid confrontations. I recently took a few weeks off from my job as a programmer, telling human resources that I'm suffering from work related anxiety, getting a note from my psychiatrist to back up my claim. Of course , being timid and non-confrontational, I didn't tell her exactly why my psychiatrist had order me two weeks off to rest, but seeing as how I've not taken a day off since my high school graduation ceremony, they were eager to let me so as to avoid any liability if I had a nervous breakdown at work or something. In hind- sight, I guess I actually enjoyed being miserable most of the time and part of me not telling her was to wallow in my self-pity. This all could have been avoided had I come clean with her in the first place. To be clear, it wasn't anything weird. I had an issue with workplace bullying.
The guys doing the bullying weren't bad guys either; they're just the typical office frat boy that kind of never grew out of their college days. What was happened was since I first started working for the company I became the target of weekly office pranks. I wasn't the only one, but I was hit more frequently. Typical stuff, like whoopee cushions, snakes in a can of nuts, cubicle draws filled with packing peanuts. I never complained, so I guess they assumed I thought it was funny, and afterwards they'd have a laugh with me, I'd put on a fake smile and go about my business. I started working for this company when I was seventeen to support myself through high school and college, not intending to stay, but the job market for English majors who minored in C++ is stagnant, especially if you have anxiety problems standing in front of an unruly classroom full of children.
I'm twenty-two now, so for five years their pranks have worn on me like an old sock. It wasn't just their pranks too; I've had other things on my mind. I've been sexually confused for a major part of my life, but also the stress of supporting myself, no vacations, and the stress of work. It all came to a head when I had a panic attack one day while waiting for some code to compile. Nobody bothered that day me so I pretty much stayed it out in my cubicle.
My Psychologist ordered me to take a vacation. So for two weeks I spent a lot of time painting little pewter figurines for Dungeons and Dragons and a lot of drinking. Not drinking, like drown my sorrows, alcoholic drinking, I had collected a lot of spirits I meant to try out some time. I also spent a great deal of time pouring over women's lingerie catalogs and online clothing stores. Up until this time, except for DnD nights, I didn't have much free time, even to indulge in some of my desires. Surviving was more important than my wished to be a woman.
After two weeks, I came back to work to find my entire cubicle covered in aluminum foil. Everything was covered. Pencils, pens, computer, monitor, keyboard, desk, my personal effects...
My anxiety was at an all-time high, I was sure I was going into a panic attack. Of
course nobody really understood and these things happened to anyone else when they went on vacation, despite my note to HR and the email I sent out asking for these kinds of pranks to not happen to me.
I just broke down after my manger told me that I was going to clean it up and get to work within the hour or else I'd be speaking with HR about not doing my work and taking a personal leave. I took some pictures, documented some complaints to HR and left for the day.
The first thing I did when I got home was cry in the shower for a good five hours. I kind of emerged from the bath room after realizing I was freezing. After calming down, I checked my phone for messages to find out that I had been fired. I called my psychologist who called an attorney who called my work who called me saying I had not been fired, and I was "free to come back to work tomorrow and would receive a written letter of apology."
It might seem extreme to you, but I didn't go back for a week, and when I did I was only there to hand in my letter of resignation. My cubicle was still covered in foil. I sued them for creating a hostile work environment and settled for an undisclosed amount of cash. The Frat Boys and the Manager were fired.
For the next month or so I was in a daze. This time for real I found myself drinking heavily just to get drunk. Sometime in June I ran out of booze and found myself sober. I found myself looking at the lingerie magazines again. I suddenly was well off to do whatever I liked. I ordered some women's pajamas and panties, some sex toys and makeup. While waiting for my packages to arrive, I looked around at my condo. Half of it reflected the desires that I struggled for years with. The other half was typical male apartment garage. Silk flowers sitting in a crystal vase that belonged to my mother on top on a coffee table made up of orang crates and a chunk of plywood. That theme pretty much played out throughout the entire condo. I went to the hardware store and Ikea and came home with pink paint and pink furniture.
Without even thinking, I decided to start indulging myself. At first it was just my bedroom antics. With my new pink walls, my new pink bed, my pink shelves and my pink throw rungs, I masturbated my ass with a pink vibrating dildo in my pretty pink pajamas with red hearts and pink panties with a little rosebud on the front.
I wasn't a big man. I'm only just barely five and an half feet tall. A lot of my problems probably stemmed from my timid little frail body. But being so small did have i ts advantages I found out. Being young and small, transforming myself into a woman would be all the easier. I confessed to my psychologist and begged him to put me on hormones. It took me almost half a year to get him to write the prescription, but by now I had taken the change in full force. Every day I would spend my days at home, reading raunchy romance novels, dressing up in women's clothing and practicing my makeup. Eventually with my now long black and curly hair and my skill with the applicator, I could pass of a very pretty cross dresser.
My first night on the town ended brilliantly. I booked a ticket for San Francisco and would have my coming out on Castro. I checked in as a man, when I walked back out of that Hilton, I was a drag queen. I wore a sexy black cocktail dress, high heels, and a new pair of breast forms. My hair was still unstylish, but I went to a salon and had my first perm and manicure. I found myself in a gay club. There were, as you might imagine lots of neon rainbows, men making out with men, women dancing with women and the cheap club scene pop music that plays at every club. I was still nervous and found myself to be a really talented wallflower. I just watched for a few hours until I was asked to dance by a most handsome stud. His hair was bleached, his skin was tanned, his abs were ripped and his skin was soft like velvet. The scent of old spice lingered off his chest and I was taken back and the Adonis standing in front of me.
"I'm a man." I kind of mumbled out, tripping over my tongue, afraid he thought I was a woman.
"No shit." he replied tome as he led me to the dance floor.
Saying he asked me to dance, is a bit of an overstatement. He just yanked my arm and said something inaudible over the bass track booming throughout the venue. I'd been drinking a few foo foo drinks by then and a little uninhibited. ME, being the shut-in had no idea what to do. At first it was me, looking dumbfounded while the stud muffin just humped me. Some women and another drag queen helped me get the danc e down eventually and in no time
I was bumping an grinding with some really, hot men.
I only spent a few hours there before coming home with another man. I don't remember his name, but I do remember his body quite well. He wasn't ripped like my stud from earlier, but he had the sort of homely look and personality that you see in a gay man, who guess is the woman in the relationship. About ten years older, slightly balding and wore glasses. But he was fit and he had a really incredible cock.
The dildo U had at home was only about an inch in girth, but his was clearly twice that as he slid his fat ckock into my ass and taking my virginity. He pounded me for a while before cuming inside me, apologizing for getting carried away. And as for my reach around, I didn't last nearly as long as he did. Within a minute I was blowing my load all over his back. It felt incredible. Compared to the pussy in a can, his ass was tight, it wrapped around my cock, squeezing with every thrust. A few more times, we took turns before calling it a night. He left me with a long and passionate kiss and walked out of my room.
For the next hour I was bleeding out my ass, but after a few shots of whiskey I passed out on the bed and awake the next morning. Everything I had done the night before finally donned on me. Hung over, I cried for a bit, before coming to terms with what I did. I don't regret it at all. I was the time of my life and I did it again the next evening. This time with a fellow tranny like me.
For the next hour I was bleeding out my ass, but after a few shots of whiskey I passed out on the bed and awake the next morning. Everything I had done the night before finally donned on me. Hung over, I cried for a bit, before coming to terms with what I did. I don't regret it at all. It was the time of my life and I did it again the next evening. This time, with a fellow tranny like me.
Her cock wasn't as big as my last john, but her fake tits bounced and jiggled ad she mounted me and shook them in my face. Sucking her nipples, I decided that I too should get a implants. For the next five days I brought along someone almost every night. I'd take my transformation in stride and embrace my homosexuality after that I arrived back to my condo and started to live my life as a woman from then on out. Today I'm happy with my lover and fellow transgendered partner. Together we're prepared for the final surgery. Be both spent most of my money on surgeries and clothes, but finally I'm no longer suffering from anxiety and I have great C cup breasts.