Career Shift

by Marty S

 

Receptions are not my favourite things in the world to attend. I don’t mingle and ‘rub elbows’ like agents and sales people do. I usually end up at the bar drinking alone, looking at all the phoney people. I am a writer, a sports column writer more specifically. The magazine that I write for is one of the biggest national publications with a huge male readership. They were promoting the new issue, which featured a calendar and had the entire hotel convention facilities booked. I was obliged to attend.

I had no reason to complain about my job. It paid great, I worked very little, and I had the prestige of bragging that I write for one of the top five magazines in the country. My column is usually three to five pages per month, which includes up to a page and a half of photographs. I had been writing box scores and rehashing press releases when this magazine started up and was building its staff. I was in the right place at the right time and for the first few months worked for nothing. Now after three years, my monthly expense account is more than my first two years salary as a writer.

Like I said, I am obliged to attend these functions. I do however make the best of them. You see, once and a while I get this urge to do something very out of character. A while back after a party, a female guest had left behind her bra in my bathroom. For whatever reason, she never claimed it back. I kept it for a long time and one day I got this notion to try it on. It was a sexy leopard print design with black lace trim. I loved the way it felt and found myself posing in front of a mirror. Things progressed after that when I bought a pair of panties and a garter belt to match. I then got my hands on a hot black dress with leopard print trim around the collar, and sheer black sleeves. I kept going and bought a pair of 4" black patent pumps and black stockings. I put on my entire outfit and posed in front of the mirror. I remember thinking that with my slim, athletic figure that I could almost pass for a woman. I decided to complete the package by purchasing a curly, red haired wig and makeup. After several practice sessions at home, I felt that I could pass as a woman in public. I had the urge to try it but wasn’t ready to just walk out my apartment door like that. I had to keep it a secret. This hotel was an excellent opportunity.

I brought my outfit with me from home and checked into my room early. The reception was at seven, and I was in by three. I showered and shaved in the room and then did my makeup. My green eyes were framed in an abundance of mascara and my lips, bright cherry red. I put on my wig, my leopard undergarments, my dress, stockings and high heels. After a dash of perfume, I set out from my room and rode the elevator to the lobby. One guy stepped on and was checking me out, which was my first test. I passed and sighed a great relief. I was wearing a pair of sunglasses that disguised me a bit more but left my big false eyelashes in full view. I confidently strutted threw the hotel lobby catching a few stares along the way, but I figured out of admiration more than suspicion. A couple wolf whistles confirmed this. I was as high as a kite with the adrenaline rush from this adventure. I even walked into a few of the fashion shops in the area and the women in the stores seemed none the wiser. There is a real sense of power that comes from a dress. The feeling that all eyes are on you and want you is a thrill. I had done bungee jumping, rock climbing, even skydiving and this was right up there.

I hadn’t noticed how much time had past and started back to my room. It was getting late so I got out of my female cloths and quickly washed off my makeup. I hurried into my male attire, grey jacket and pants with blue shirt and silver tie, and headed for the convention room for the reception. My heart was still pounding from the excitement I had experienced. I did my required greetings with the chief editor and a few of the other writers then made my way to the bar. The social aspect of these events was almost plastic. I would spend the rest of the evening waiting for my queue to leave while drinking as much as possible. I would however have the recent memory of my walk in feminine attire to relish privately for the rest of the night.

After my second or third drink, a stunning creature shattered my solitude. She sat in the seat right next to me even though there were many empty ones all along the bar. I had never seen her before. She was probably late thirties, blue eyes, and sassy brown hair in tight curls, incredibly beautiful with an hourglass figure wrapped in a tight black cocktail dress. I noticed her charcoal stockings had seems up the back that were very sexy. She wore 5" stilettos that put her at my height. She smiled at me, charmed by my staring. I gave my head a shake and introduced myself and offered the pretty lady a drink. She took a cosmopolitan and I had another dry martini. She kept her bright blue eyes locked tightly onto mine and she never stopped smiling. I don’t usually pick up women easily. I am not ugly or anything like that, just kind of plain looking and shy. This was a pleasant surprise. She introduced herself as Audrey Kline. Bells went off in my head immediately. I recognized her name as the owner of Go Girl magazine. She must know some of the top brass at my magazine. I was thrilled to meet her in person and would never have guessed her to be so good looking.

We made some small talk about the party, and then she started asking about me. She was very familiar with my work and claimed to admire my writing style. I knew that she wasn’t full of it either as she quoted a few of my articles. I was totally enchanted by her. The next thing she did was a complete surprise too. Audrey told me that my style was ideal for her readers and that she would like to see me writing at her magazine. I was a bit shocked by the job offer. It was a women’s magazine after all. I told Audrey, "That’s very flattering but I write for a men’s magazine and don’t know if my work would be right for yours."

"Nonsense, modern women are big on extreme sports and I know that you love writing about that stuff. We are progressive and don’t want to be another puff fashion magazine. I think that you should meet with or chief editor and talk about it," Audrey argued. She did have a point. My magazine was huge but I didn’t have the creative freedom that I wanted. I love women’s tennis but the only way I could write about it in my current job was if it had something to do with Anna Kornakova’s hemline. Audrey handed me a card with the name of her chief editor, Tom Hadden and told me I could call him as early as Monday morning to set something up. At that point she finished her drink, gave me peck on the cheek and made her exit. I was stunned and disappointed. Had all that been a head hunting exercise? I really wanted to take her to my room. It all seemed too weird.

All weekend I contemplated the offer. It would be foolish in a way to leave a magazine as successful as The Max, but I had been feeling stagnant and unappreciated lately. Monday morning came and I gave Tom Hadden’s office a call. The receptionist had a dreamy, bedroom voice. I remember how hot she sounded and tried to picture her in my head. Tom Hadden was expecting my call and eagerly set up an interview for the next day.

I fretted all morning wondering what to wear. I opted for a stylish olive and kaki suit that I figured would be more female friendly than a masculine power suit. The head office for Go Girl magazine was on the 29^th floor of a big office building downtown. The parade of hot looking career women going in and out of the building was endless. If nothing else I should take the job just for the scenery. I rode the elevator up to floor twenty-nine and entered the offices of Go Girl. It was very posh with low lighting and a large assortment of plants. It made sense, considering the magazine ran a monthly interior-decorating column. The receptionist was a sweet young blond with long curly hair and green eyes. She was better looking than I pictured in my head. Her face was flawless and when she stood up to greet me I was taken by her incredible figure. Her sexy black skirt didn’t hurt either, which flattered her round ass and shapely legs. She wore black seemed stockings like Audrey’s and her shoes had to be five inches high. The young lady introduced herself as Janey and led me too Mr. Hadden’s office. The corridors were quiet and dim, but I was enchanted by the wiggle of Janey in front of me. I had passed what looked like a research room and noticed two more very hot looking, and well-dressed young women inside. We finally arrived at Mr. Hadden’s office and were met by his private secretary. The tall brunette greeted us and informed me that Mr. Hadden was expecting me. She then gave Janey a glance with her brown eyes they shared a smile and a wink. Janey returned to her desk.

The tall, slim secretary was nothing short of drop-dead gorgeous. Her hair fell to her shoulders in a pageboy style and she wore glasses that seemed to accent her sexy eyes. She wore a charcoal grey skirt sit with a maroon blouse. She also had legs that could stop traffic covered in seemed stockings. I was beginning to see a trend. Her shoes were black paten leather stilettos with a wide ankle strap. She was a walking wet dream. She escorted me into the office and I met Mr. Hadden. He was a short man with a brush cut but looked fit and youthful and was dressed in a two-piece silver suit. He got up to shake my hand and turned to his secretary who was patiently standing by. "Natalie can you bring us coffee please," he politely asked. She turned and left and I could not help myself watch her glide away.

"Natalie is pretty hot, isn’t she?" Tom asked, knowing that I was checking her out. He winked at me as if to say that we could be non politically correct.

"I don’t know how you could ever get any work done," I added, making Tom laugh knowingly.

We proceeded to talk endlessly about my career, the magazine, and a bounty of other topics for over an hour. We did pause for a while to admire Natalie again when she returned with our coffees. I had to fight the urge to drool when I watched her seductive hips sway as she walked and her bright, beaming, brown eyes.

Finally, Tom asked me straight out if I would come over and join the Go Girl magazine team. He couldn’t guarantee the same money, but insisted that the perks of the job would make it worth my while. I was honest with him that I loved the idea but still did not think that I would fit in at a women’s magazine. He giggled a bit and asked Natalie to come into the office using the intercom. Once again the statuesque brunette glided into the office and waited for instructions. She stood facing me, with her legs together, and her hands behind her back.

"Natalie, our guest is not sure about joining us, do you think you could help me persuade him?" Tom provoked.

Natalie’s eyes brightened up and a big grin came across her face. "My pleasure ma….sir," she stuttered. Natalie took a step over to the couch where I was sitting and sat across my lap and planted a big wet kiss on my lips. I melted into her lips. Her tongue was soft and gentle. Her firm body pressed into me. Soon her passionate kiss stopped and she reached for my pants and began loosening them. Tom Hadden sat patiently and grinned. Natalie had a devilish gleam in her eye as my very pronounced hard-on was exposed. Her head dropped and soon she had engulfed its entire length into her perfect mouth. She easily deep-throated all seven inches without trouble and gave me the most incredible blowjob of my life. She seemed to know exactly what to do, how to use her tongue, when to add pressure and when to ease off, all the time keeping it very wet. Throughout the entire blowjob she never took her eyes off mine either. I was ready to cum in record time and announced to her that I was about to. She took me deep and didn’t bat an eyelash as she swallowed the contents of my balls. Pure heaven!

Natalie gave me a small kiss on the cheek and left the room. I was in a state of shock. "Like I said, you can’t beat the perks in this job," Tom said interrupting my trance. I straightened up my pants. "You will have your own private secretary of course, and as you can see, we are pretty loose about office relationships here. We have never had a sexual harassment suit, just lots of requests for more," he went on. The offer was too good to pass up, despite my reservations, I decided that it was a dream job and told Tom that I was in.

"Good! You have made the right decision, you will be a perfect addition here," Tom exclaimed as he shook my hand. "As you can see, as well as having liberal office attitudes, we also have a very high standard to maintain," he continued. "For example, you may have noticed that we have a strict dress policy that all employees are expected to maintain." He was right, I had noticed that all the women were dressed to the same high level, with the short but elegant skirts, the seemed stockings, high heels, designer tops, perfectly coifed hair. I had not seen any male employees at that point, just Tom.

"I did notice the females all dressed similar but I haven’t seen any other males so I’m wondering if how I’m dressed now is okay?" I inquired. Tom snickered and paused before speaking.

"That is not appropriate attire for the office, the standard is the same for all," Tom insisted. I was puzzled. Did he mean that his suit was the standard? What did he mean by "same for all"?

"So you mean silver suits?" I asked naively. Again, Tom snickered at my question. I was beginning to get frustrated. "What is the standard uniform for men in the office then?" I asked bluntly.

"The same applies for everyone," he stated again.

"But I haven’t seen any male employees yet," I continued.

"Yes you have, Janey and Natalie for example," Tom replied. Now I was really confused. Why did he say that Janey and Natalie were male, that was impossible. I puzzled some more, looking very confused.

"What?" was the only stupid sounding reply that I could come up with. Tom called Natalie into his office again. Once again she promptly glided into the office with a grin on her face as if she was in on a giant secret. She again assumed the subservient position in front of her boss. Tom got up from his seat and took Natalie by her hand and he sat on the couch next to me. He pulled Natalie to his lap and began stroking her long, perfect thighs. I watched as his hand eased her skirt up passed her stocking tops to her crotch. He was kissing her breasts through her blouse and she was kissing the top of his head. Soon her black lace panties were visible and Tom’s hand was busy rubbing them on the outside. Natalie threw her head back in delight. She was enjoying the attention. It was an erotic sight but I still didn’t understand. I was busy watching Natalie’s reaction and glanced down again to see that Tom had pulled aside Natalie’s panties and had hold of her thick ten-inch cock. Her cock and balls were shaved perfectly smooth. Tom stroked it with his hand and then dropped down to it. He began wrapping his mouth around the head and taking long sucks on it. I was shocked but also very aroused. I was getting another hard-on already. Tom took some deep, long sucks on her getting it very wet. He then looked up at me as I was staring intently.

"Want some?" he offered. All I could do was nod my head. He held Natalie’s cock out for me. I leaned down and began kissing it and licking it all over. I had never had a cock in my mouth before and never thought I would like it but watching Natalie moan in ecstasy as I administered a blowjob made it wonderful. I was soon pumping my mouth up and down on her stiff shaft as Tom moved lower to lick her balls and put a finger into her bum. While enjoying the oral service we were giving, she reached over and squeezed my erection through my pants. Natalie unzipped me again and pulled out my rejuvenated member. We adjusted ourselves on the couch, with me on the bottom and Natalie over me in a sixty-nine position. She took my cock into her sweet mouth again as I did the same to her. The sight of her stocking top thighs on either side of my head and her pretty pantied bottom were sexier than hell. Tom stepped up from behind Natalie and moved her panties aside further, exposing her smooth ass crack. Then he began licking her asshole, only inches from my face. He really probed her deep with his tongue. I had never done that before but it sure looked good. She began thrusting herself into my mouth, as my throat took more and more of her length with each stroke.

Tom stood up and had his thick hard-on in his hand. I watched as he positioned the head of it against Natalie’s little puckered hole. It was so close to my face. I had the best seat in the house. Tom slowly slid it into her tight rectum until his balls were touching hers. Natalie barely flinched and only replied with a moan around my cock. This was extremely intense and I felt that I wouldn’t last long getting sucked by this beauty and watching her get fucked inches from my eyes while sucking her huge cock. Tom was really fucking her ass hard too. He took long, hard strokes into her behind making her thrust harder into my mouth. Just as I thought that I couldn’t hold it any longer, I felt a rush of hot cum flooding my mouth. Natalie was coming and coming hard. Her cum was hot and salty, and I tried to swallow as best that I could. It was then that I released my load too, which Natalie ate up without hesitation. After we each had drank up each other’s orgasms she pulled herself from my mouth and released my member from hers. I swallowed the overflowing contents in a big gulp. Tom removed himself from Natalie’s caboose with a trail of cum fallowing his cock. Natalie immediately parked her bum onto my face and I licked up the cum from her asshole. It was all like a dream and I was helpless to control it. Once Natalie was content that her bottom was clean she stood up and adjusted her panties and skirt. She smoothed them out and left the room.

I lay there, with my used cock hanging out and a glaze on my face. Tom zipped himself up and returned to his desk. "So you see now, the dress code applies to everyone equally," Tom restated. So even the men dressed as women. I would never in a million years have guessed that Natalie or Janey for that matter was not a real woman. Then the next thought entered my mind; did this mean that I was expected to dress feminine too?

"I know what you about to ask next, so don’t worry, I have answers for you," Tom informed me. "Our image consultant, Mai Wong, is a makeover expert and will help you change into the proper woman. You’ll be set up with an initial wardrobe allowance of two thousand dollars to get you going." That answered that question.

"So how many of the girls here are actually….you know?" I asked.

"All of them," Tom replied quickly. "Funny, how the nation’s fasting growing modern women’s magazine doesn’t have one genetic woman in its head office," he went on. It was extremely ironic. There had to be twenty or more ‘women’ in the office, and every one of them was a crossdresser. What a shocker.

Tom made a quick call to Mai Wong. "Alright, we can get started today, Mai will help get you dolled up for a photo shot, this month goes to press on Friday and I want to run a promo ad with your picture. It will read, ‘Mary Callahan on sports starting next month in Go Girl.’ I hope you like the name. We can’t use your male name obviously," Tom insisted. "It will be great having a redhead on the staff too," he added. Now I was confused again. I wasn’t a natural redhead so how could he know about my red wig?

"Wait a minute!" I insisted. "How could you know that I would be interested in doing the job as a woman?" I asked.

"The Max party of course," Tom started. "Your parade around the hotel in the red wig and black dress was a great show," he added. Before I could ask more questions, Mai Wong arrived. She was a slim Asian woman about my age but very beautiful and refined. She had shoulder length black hair and wore the company standard seemed stockings and short skirt with 4" high heels with ankle straps. Her skirt was charcoal and her jacket was royal blue. Mai was also a man in women’s clothing. I would carefully screen everyone I met to discover that it was true; all of these gorgeous women were all men in drag.

Mai guided me to a make-up room and began working. She was far more talented at make-up application than I was and gave me some pointers as she worked. She then brought me a red wig, which was slightly longer than my shoulders in a Jennifer Aniston style. She continued with cloths by picking out a navy skirt suit, black seemed stockings and 4" velvet high heels with ankle straps. The transformation was brilliant. After two hours I was a new woman. We made our way to the photo studio where my pictures would be taken but stopped by Tom Hadden’s office on the way. Natalie was pleasantly surprised at my new look. She led us into the office with a big smile.

Once inside, it all seemed to make sense. We were not greeted by Tom, but by Audrey Kline instead. She was looking as stunning as I remembered from the party. That’s when I realized that they were one in the same person. I can’t believe that I never put the two together. I was wondering how Tom got away with being the only male in the office. "Some times, we need a male representative for things as well as making trips to the printing and distribution centre out in the burbs. That’s when Tom steps in. Otherwise, Audrey runs the magazine, I like it better that way," Audrey explained. "As for spotting you at the hotel, I figured that hot redhead was a cross dresser but wasn’t sure who it was for sure until I spotted you at the bar. You looked like a candidate and when I looked at your eyes, I knew that it was you. You still had a smudge of mascara on your eyelash," she added. So that was it.

After the photo shoot, I went home still dressed as a woman. I gave my old job two weeks notice, which they didn’t even try to fight. Male sports writers were dying to get in there. I did get a healthy severance from them, which didn’t hurt. I told them that I was going away for a while and getting out of the business. I wonder how many of them would link the arrival of the new Go Girl sports writer with my sudden departure.

The first official day on the job arrived and I was a bundle of nerves. I arrived dressed in official company code. I wore a grey pinstripe skirt suit with white blouse. The hem was of course short and my stockings were black with seems. I wore 4" black heels with ankle straps as required. The receptionist, who was not Janey, greeted me. The new girl introduced herself as Paula and politely welcomed me. She directed me to my new office and I made my own way. Many girls approached me along the way with pleasant smiles and warm greetings. I arrived at my destination to find Janey waiting for me. She was dressed in a very smart black skirt suit. She was full of energy and seemed genuinely excited at my arrival. "Hello Ma’am, I’m Janey and I’ll be your personal assistant. Let me show you your new office," she stated with a rehearsed polish. " Can I just say how happy I am to be working for you? When I first heard that you were joining the magazine, I wrote up my memo immediately to be your secretary. I was promoted the next day. I have been getting everything ready for you since then," Janey explained. She was right, everything was prepared for me, office set up, stationary, computer, security pass, everything.

"Well honey, I had set aside the entire morning to get set up, but you have taken care of all of that already. What will I do with all my extra time?" I joked.

Janey grinned, "Well, we could spend it getting to know each other better."

"Great idea hon, come on in and lock the door the behind you," I replied. I was going to love this job.

Next time, I’ll tell you about the party they threw for me after work on my first day.

Mary Callahan,

Sports writer

Go Girl magazine

 

 

 

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© 2002 by Marty S. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.