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Super Secretary By Jena Corso Edited By Angela Myers Part 3 Alan woke up as his alarm went off and got ready for work. He knew that Pam was pissed and she wouldn't be coming this morning and he had no choice but to put his training to work. After a quick shower, he blew his hair dry and took his time with his makeup. He fixed it a few times and figured it looked decent enough before taking the next outfit from his closet and getting dressed. It was weird trying to match things, but luckily the skirt and jacket were together and he selected a blouse. When he finished , he inspected himself in the mirror and was satisfied with the result. He had selected a classic herring bone black and white suit, with a lovely three button collarless jacket and matching skirt. He had remembered a girl in the office wearing something like this before and just as she had done. he paired it with a red silk collarless blouse and was surprised at how it livened the outfit up by adding a touch of color. He wasn't sure about the shoes he should put on or if he had on the right hose, but after thinking about it and recalling the girl from the office, he made his decision. He stuck with the sheer black hose he had on figuring they worked with the black in the suit, and he slipped on the red pumps, which matched the blouse. The jacket had brass buttons so he selected a gold bracelet, necklace, and matching small gold hoop earrings and put them on before grabbing his jacket and he was off to work. He was immediately inspected by Claire as he walked to his desk as she smiled, happy that he was early. "Not bad for your first time on your own," said Claire, touching his shoulder. "There's a few little things we'll need to fix. I'll be right back." "Ok," said Alan, getting to work as Claire went to her office. "Here, your hair was a little frizzy, so pull it back on top. I put one of my clips in the bag, and spray it," said Claire handing him a small bag. "Also, your makeup is fine, but the pink lips clash with that blouse. I gave you a soft red rose lipstick so it'll pick up the blouse but not look like you're on a date. Now go to the ladies room and do this quickly, because it's a busy day for you." Alan took the bag and ran into the handicap stall, having some space to work with. He pulled off his shoes and unzipped his skirt, changing to the sheer hose. He wiped off the pink lipstick before rubbing on the light red and looked at how it picked up the color in his blouse without seeming unnatural. He brushed his hair straight back from temple to temple and fussed with it a few times before pinning it in place, snapping the gold ornamental clip with a huge onyx type stone that Claire gave him. He stepped back, understanding what she meant now as tightly pulled back straight hairstyles, natural reddish lips, and sheer legs were things he saw on other girls at work. He took the hair spray from the bag, setting his style and closed the bag, and headed back to work. He could see Claire giving him a private nod of approval as he passed her office while she spoke on the phone, and returned to his desk, getting back to his job. "Damn, what a crazy day," said Chrissie, dropping stacks of forms on his desk, waking him from his typing trance. "Ok, make two hundred copies of everything, and then you have to sort and bind them." "What is all this?" asked Alan. "All the hand out material for tonight!" said Chrissie. "You didn't forget, right? We're working at the event. I'm sure you've seen how all the secretaries run around catering to everyone?" "Great," Alan complained, getting up and heading to the copy machine. He felt so lowly, copying and sorting documents as person after person interrupted him, sneaking in a single copy here and there. He fingers were getting sore and he was getting tired of the tedious work until finally he was interrupted by Claire. "You almost done, Alicia?" Claire startled him. "Ouuch," screamed Alan, looking down at his index finger. "Damn, that really hurt!" "Sorry, I'll ask them to fix that when you get your hair done," said Claire chuckling. "It's no fun breaking a nail, is it?" "No, I can't believe how much that hurt," Alan looked at his hand. "So Alicia, here is tonight's itinerary, and your duties for this evening," said Claire. "Finish up and you'll be leaving soon for the salon. They'll get you ready and have you there early to help set up, and also expect to be there late helping to break everything down. See you tonight." He couldn't believe how demanding this position was as he finished up the documentation for the evening. He headed downstairs, getting his ride to the salon and didn't even complain as he sat down while Hannah began working on him. It was actually relaxing as she scrubbed his face and redid his foundation as he lay back in the large cushioned leather chair until Natalie came over, ready to begin on his hair. "Big night out Alicia," said Natalie. "Time to glam you up girl!" "Ok," Alan sighed, not even opening his eyes. "Whatever, I'm wiped. Don't mind me and do your thing." "Oh, you'll get that second wind when you see your dress!" Teased Natalie. "It's gorgeous!" "Ouch!" whined Alan as she began brushing through his hair. "Or I'll wake up now, since that hurts!" "Sorry it's all the hairspray hon, but I can't wash it as it's better doing styles like this when it's a little tacky," said Natalie. "Just bare with me a little honey and I'll get it where I want it, and then give you back to Hannah later!" Natalie brushed through his entire head, inserting clip after clip, sectioning as she worked. It felt ever so strange as she began stretching and spraying in some thick setting solution before he felt the first plastic roller being twisted onto the back of his head. She worked at sectioning and rolling and before he knew it, his entire back of his head was covered in green rollers. She now turned her attention to the top and next to his ears, as she combed a long section in front of his face and tilted his head forward. She took thick sections between her fingers now and grabbed very large blue plastic rollers, twisting them away from his face. She did this a few times on top and then a few on each side before finally working on the last thick section in front of his eyes. It took only two large rollers as this time she twisted it under towards his forehead, before sliding on the last few pins and then covered him in a thin mesh hairnet. It was so strange seeing his reflection in the mirror when he got up, as Natalie led him over to a red chair near the wall before the bonnet was lowered over his head. It was incredibly relaxing though, feeling the heat surround his head as the nail tech came over, fixing his fractured nail as he was almost dozing off. He wasn't baking that long as the hot air switched off and Natalie came over, lifting the bonnet and checking on him. "Sorry sweetie to break that trance, but come on," said Natalie, tapping his thigh. "Maybe next time I'll do a wet set and you can relax a little longer. Semi-dry sets like this take pretty fast, and we've got plenty to do girl!" He gazed at himself , his hair all rolled up, amazed at the weird sight of his face surrounded by curlers as he moseyed back to Natalie's chair before Hannah again blocked his vision, working on his eyes. He watched her measure and cut thick false lashes, gluing them on each side and then he felt the sensation of a heated lash curler bending the false lashes, and his own, upward in unison. She worked like an artist, ,from a pallet lining his lids with a small brush and then blending his shadows across the creases. She coated them in mascara three or four times and brushed at his brows as she was careful accentuating his eyes. She brushed his cheeks and then dotted and powdered from his forehead to his chin as she studied him. On his lips went a dark red pencil outlining them ever so slowly, and the sticky sensations were soon apparent as she brushed his lips multiple times with lipstick and gloss. "Ok, she's all yours Nat," said Hannah. "I'll freshen up his lips, and then make some final touches once Olga dresses him." "So you have to be really still right now because I have to get the height and the back just right so all the edges of the extensions stay hidden. We did Malaysian links knowing this day would come, but I still have to make sure this comes out perfect, so hopefully you held a set well," said Natalie, twisting him away from the mirror and pulling off the hair net. "Lean forward a little, and I'll be working in the back first." As he felt the first roller being unwound from the back of his head, Natalie seemed to stretch it with her fingers, softly placing the unrolled curl on his shoulder. He felt her delicately place the next one as she unrolled the entire back of his head. She separated some of the curls with her fingers and seemed to hold up them up, spraying a section at a time. "Ok, you can sit up straight again now while I do the top," said Natalie as he sat up. "It's teasin' time." She now unrolled the first large curler and stretched the first section as she hovered over him, backcombing and teasing as she saturated the section in hair spray. He was almost choking as she worked over and over, doing each distinct section one at a time as he could feel the tension as she worked. He looked over seeing her take this odd half-moon shaped beige plastic device and then felt scratching on his scalp as she dug it in. It felt really odd as he felt her pulling back on his hair and looked over at her on his left with a mouth full of pins, removing one and sliding it into his hair. When she finally came back in front of him, she removed the last two large rollers from the front of his hair and then brushed through it. She took a small flat iron, sliding through it on an angle towards his left eye, sizzling the section over and over four times until she had it just the way she wanted. Finally, she covered his eyes saturating the front and the rest of his hair one final time with a heavy finishing spray. She patted it softly with her palms and smiled, pulling the cape from his neck. "Come on, Olga is waiting," said Natalie, pulling him from her chair as she led him into the back room. "Nice suit, blondie," said Olga, unbuttoning his blouse. "Now let's strip all this off and get you ready for tonight's event." She helped him off with his clothes as he stepped out of his pumps and then dropped his skirt. Quickly she had his bra off and pulled off his stocking and panties. He stood motionless, taking a large gulp of air as Olga grabbed his limp member, wrapped it in a few sheets of toilet paper and then circled the paper in clear tape. She took a cotton swab, rubbing something between his butt cheeks and then knelt, spreading them just a touch. "Breath in, Alicia," said Olga, kneeling next to him as she pulled the long strip of tape through his legs. "This will make sure it doesn't come loose." She grabbed the end of the tape with her other hand behind his rear as she as she pushed his testicles into his body cavity and pressed the tape between his cheeks. She ripped a few more strands of tape, making sure nothing could drop as he looked down, unable to see anything as she had taped him back as tightly as she could. "Will I be able to pee?" whined Alan. "Carefully, sweetie," said Olga. "With this dress, I rather you didn't remove it but pull it up if you have to. It's an unforgiving style so it shows everything, meaning I can't give you any panty lines. Underneath it honey, you've got no support. It's all you, so don't rip this tape or you'll have a lot of explaining to do, looking all glamorous with a bump in the crotch of your dress." "I don't think I'm going to be comfortable like that." "Not my problem, honey," said Olga as he held her shoulder. "I'm just here to dress you." He was beginning to tremble, watching her fasten the straps of the highest heels he had ever been in. In just a short moment, he was now in the second shoe, as he seemed to have grown five or six inches. She took a bronze tube, squeezing a cream into her palm and massaged each of his legs, coating them as he looked down, watching. The second she rose, he gave a strange look as he now saw her taking the long dress from the hanger. She knelt and held the dress open as he lifted his first foot inside it and she ever so carefully guided his shoes through the delicate material one at a time. When he was steady footed with both heels on the floor, she guided the dress up his body and before he could blink, was lifting the curls on his back and fastening it behind his neck. "Oh la la sweetie!" said Olga, standing up and stepping back. "Very elegant, dear." "I love the color on him Olga," said Hannah, coming in now and taking out her lip brush. "Is there a blazer or something?" asked Alan as she painted his lips. "I'm like half naked in this." "Oh stop. It's gorgeous," said Olga, adjusting the breast area. "I bet you never said that if your girlfriend was in something like this." "Well, I guess not," said Alan as he got a whiff of the strong perfume as Hannah touched his neck and wrists. "Then shush and enjoy being sexy," said Olga, adjusting the other side of the dress now. "I just used some double sided tape on your boobs, so be careful if you're dancing that you don't pop out of this. But I think you'll be fine as this stuff holds so well." "I'll be working and even if I wasn't, I won't be dancing dressed like this," Alan said, looking down at himself. "I'll barely be walking in these shoes." For the first time, Alan was out of his now customary business attire and was dramatically dressed in evening wear. He spun ever so slowly toward the three way mirror behind him in the dressing area, getting the full view of himself from every angle in the stunning long gown, feeling more like he was headed for the red carpet rather than the evenings corporate social. His dress was an elegant long chiffon, form fitting evening gown in a peachy orange spring like color, which featured a floor length A-line slightly flowing skirt with a sexy side slit, and a small, fly away train. He was distracted as he touched it, feeling how incredibly soft and thin it seemed as it instantly invoked goose bumps across all of his exposed flesh. He knew immediately why they had taped his breasts, as in front a long thin keyhole slit ranged from his semi-sheer silk collar to the breast bone, exposing a long strip of skin between his breasts ,giving him an incredibly sexy look as the soft chiffon halter design covered only his breasts above the waist. Heavily jeweled rhinestones decorated the collar as it wrapped around his neck and also coated the attached, four thin straps across his shoulder blades as his entire back and spine were on display down to his waist. The floor length skirt gathered like a center drape beneath a jeweled waist, finishing off the ultra-chic gown's look as his bronzed, bare right leg slid out almost all the way to his hip as he took a small step. He couldn't believe he was in these shoes, which were much higher than the conservative office pumps he had worn, as he wiggled his painted toes, staring at the gold platform stiletto sandals with a thin six inch heel, which now overly arched his feet. His makeup was no longer centered around pinks and pale colors, as his lips were now a bold glossy orange highlighting his face, and his lids were done in glittery bronze. His false lashes looked tremendous next to his old natural ones, and his face had never shined like this, reflecting light as his makeup had been set in a glimmering powder. His professional type blonde hairdo had been pumped up for evening as well, as he touched up top it felt like concrete from all the heavy spray. In front, it was still swept to one side yet no longer from a side part. Instead it hung like a very long side bang, twisting under beneath his chin on the left. From the middle of his head from ear to ea, his hair had been pulled back and teased up into a poofy style, creating a perfect bump towards the back of his head as he now realized what the plastic was for. From one side to the other now protruding from under the bump, streamed layers of loose curls, which cascaded across his shoulders as it was strange to feel their stickiness on his bare shoulder blades as he moved, and his large gold chandelier earrings swayed with them. "It's time sweetie!" "Can't I put my suit back on!" said Alan as nervous as ever as Hannah twisted two large gold bangles over his left wrist. "I'm like half naked, and with all this make up and big hair." "Not a chance, Alicia," said Hannah, handing him a little gold clutch and slipping a few gold rings on him. "Girls would kill to look this good in that dress and to have your looks." "You have no idea how gorgeous you look, honey," said Olga. "You're in a chiffon Versace dress with Jimmy Choo shoes and a Chanel clutch . It doesn't get much better than that, my dear." "But I didn't want this," said Alan. "I just want to do my job and get this over with." "Well your boss said part of the job is being glamorous tonight, and looking fantastic for you clients, honey," said Natalie, holding up a head shot of Carrie Underwood. "That meant an outrageous outfit with amazing hair and makeup. I did your hair like Carrie's, as you have the same cut and multi-dimensional blonde color. She always looks great with some curls, a sweep, and a bump and honestly so do you. Your makeup is more dolled up, but that's by design, to go with that fabulous dress. Now your car is here so go knock 'em head Alicia." "Lift the dress when you get outside," said Olga as Alan felt much better, warming up as Olga dropped a long white shawl over his shoulders. He cautiously walked in his skyscraper heels, lifting the end of the dress as he walked outside. It was weird seeing his leg poke all the way out as he sat in the cab and pulled himself under as much as he could. Soon he arrived at his destination. He got out, holding the dress again and took very short small strides up the granite steps and into the event. "OMG," said Chrissie, seeing him as the girls all rushed over, hugging him. "You look unbelievable." "What a dress, and the hair!" said Shiela. "Fabulous, honey." "Not bad for a rookie, Alicia," said Claire as Alan's jaw dropped when he saw her in a red strapless gown. "Now enough of the niceties, ladies. Everyone looks beautiful. Let's all get to work please." Alan did his best, smiling and handing out documents as people wandered in. He stood there doing his job, catering to everyone before he almost jumped out of his skin, feeling a finger slide down his bare spine. "Holy crap ," Alan screamed, almost falling over as his friend Kenny caught him, laughing at him. "That's not funny." "You got some body there, buddy," said Kenny, as he lifted Alan back to his feet. "He's like a Barbie," said his other friend Larry, as Alan straightened himself, balancing in his heels. "Who knew he could look this hot." "Fuck you," said Alan. "You're such idiots." "Alicia, may I remind you that you're in mixed company this evening, so please mind that tongue," said Claire walking over. "Alicia!" Claire gave him a look to kill. "Now gentlemen, you look very handsome this evening, but I'll also remind you to keep your hands off my girls, and you know our policy about flirting with the ladies at events like this, regardless of how attractive they may appear. Now run along Alicia, and get these fine young sales executives some champagne." Alan was fuming after being scolded and felt belittled as he headed towards the champagne fountain, taking a few glasses. He could see them smiling as he looked down to avoid eye contact as he felt like they were mocking him from across the room as he headed back towards them. He was already uncomfortable and incredibly self-conscious, hearing every click of his stilettos on the polished marble, and well aware of how his leg was fully exposed through the slide slit as the small train dragged across the floor when he moved. "Thank you. You certainly make a wonderful hostess!" said Larry, as he reluctantly served his buddies. "How about a light. I know there are souvenir matches near the front desk." "You wouldn't mind running over and getting them, would you Barbie?" teased Kenny. Alan rolled his eyes without saying word as he turned, heading for the matches. As he returned, he saw a huge group of sales people awaiting him, holding cigars. He held out his hand with the matches as Kenny stuck his cigar in his mouth and stepped right in front of him. "You wouldn't mind lighting it for us, would you Alicia," teased Kenny. "Of course not, sir," replied Alan, just about ready to explode, lighting cigar after cigar until finally he was finished. "That will be all for now , toots!" said Larry, sending a large puff of smoke in his face as Alan turned, walking away. "Just a minute please," said a voice from behind him as he felt an entire open hand on his lower back as he had taken five or six steps. "Hello sir," said Alan, surprised by his boss. "That's some dress," said his boss, looking him up and down as he stepped in front of him. "I'm certainly glad you've gone all in on this and not embarrassed yourself, or caused any issue in my company. I'm quite impressed actually, and Claire tells me you've been working hard." "Thank you sir," said Alan. "I love the company, and I'm a man of my word sir." "You mean woman, right," said a voice from behind Alan. "I believe that's what she meant," said Mr. Cappa, sharing a chuckle. "Alicia, this is my son, Robert." "Of course sir," said Alan slightly embarrassed, extending his hand. "Nice to meet you, Robert." "The pleasure is all mine." Robert kissed Alan's hand. "So, Robert will be a good person for you to get to know, Alicia, as he'll be opening our west coast office next month," said Mr. Cappa. "Starting next week, you'll be getting to know him better as all the girls will be working on it a lot to get it ready. It's a very exciting time." "Certainly seems to be, sir," said Alan, dying to wipe Robert's saliva from his hand. "Alicia, let me introduce you to my management team, and maybe we can chat a little about your skill set," said Robert, holding out his arm. "Dad, I'll catch up with you later." "Of course, son," said Mr. Cappa, giving his son a strange look as Alan stood there, not knowing what to do. "Ready Alicia," asked Robert, cracking a soft smile as Alan took Robert's arm. He wanted to crawl under a rock as he could see his co-workers staring at him curiously as he was led across the room on Robert's arm. Robert pulled a chair out for him as he sat at a small table as they chatted and sipped champagne for about thirty minutes, until Claire walked over. "Robert, I'm sorry to interrupt, and I hope you don't mind, but I'll need Alicia soon," said Claire. "She has some things she must handle before your father speaks." "By all means! Don't let me put a monkey wrench in any of my father's plans," said Robert. "We'll speak again soon Alicia." Alan got back to work catering to guests, handing out documents, and serving people as Claire wasn't shy about piling on the work. Finally the night was almost over, as he was mentally and physically exhausted as he and the other girls had to usher all the guests out and make sure everything was in order. He was packing up the last few boxes when Claire came over, dumping a series of extra documents on his table. "Pack these up as well, Alicia. Not bad for a rookie at an event like this," said Clair, grinning as she paid him a mild compliment. "Is that a compliment from Claire I just heard?" Alan was surprised. "I think it was a good night for you. You spent six hours in those shoes, your hair held up nicely and you made it through the night without a fake boob popping out of your Versace. I'd call that success, Alicia," said Claire, before walking off. "Plus, I think you might have even enjoyed being waltzed around on the bosses son's arm like some little prom queen. I know most of the girls from the office and a few of your sales buddies found that quite interesting. Be in early, as it'll be a busy day tomorrow." Finally Alan finished and headed home. He was asleep in no time, being wiped out and felt like a zombie as his alarm went off in the morning. He was actually happy to be back in more comfortable shoes and his business suit as he headed for work the next morning, as it was business as usual for everyone "You seem to have made a good impression on the bosses son," said Claire, coming over. "Please Claire, I'm loaded with work," Alan said. "Tease me later, when I catch up a little." "No, I'm not joking, Alicia. You made a very good impression on his son," said Claire. "Finish these memos and then you'll begin working with him on some of the work to prepare for the west coast office. He requested you." "Really?" said Alan, surprised. "Doesn't he know I'm new at all this, and I'm not really one of the girls." "Maybe? Maybe not?" said Claire. "I really don't know, or even give a shit. Now stop asking questions, and do your job. He expects you in his office in thirty minutes." Alan put his head back down and did his work. He went to Robert's office on time and it was all business as he was given tons of extra tasks. He worked most of the weekend with some of the other staff, and for the next few weeks as they were juggling their regular jobs and helping prepare everything for the west coast unveiling, as he was nearing the end of his time as a secretary. "Alicia, may I see you in my office?" said Claire, interrupting him from his work as he came in. "So we both know tomorrow's your last day of obligation for our bet, so let's just be on the same page and end it professionally, without issue." "That's my intention, Claire," said Alan with a huge smile on his face. "I think I did my part." "I just want you to know that I'll set up a meeting towards the end of the day with personnel, and then I'll call Pam to make arrangements to have your male wardrobe returned," said Claire stopping and looking up at him. "But before I do ... Well I just want to make sure that is what you want, correct?" "Are you kidding me?" said Alan, almost jumping at her. "Yes, of course!" "I had to ask Alicia," said Claire. "You seem to have adapted well, and if anyone didn't know you well, then they certainly don't realize that you're really a man. Half the guys in this company would ask you out." "Ok, on that note I'll be getting back to work, please," said Alan, grossed out. "Ok, but don't forget that Robert set up a dinner tonight at Tavern on the Green," said Claire handing him a note. "He requested you there, so it'll be your last after hours business function as part of my group." " Oh great?" whined Alan, taking the note. "Olga will have your dress, and you've got a hair appointment at 5:30," said Claire. "Enjoy your last night out as Alicia." Alan worked as he normally did the rest of the day and headed into his car to the salon. He was used to all the drills there as they did his face and hair, and then Olga dressed him appropriately as he headed to the restaurant. He was in a classic velvet little black dress this time, which was strapless across his shoulders and held in place with a small slice of velvet strapping just above each bicep. In front, the v-neck design showed just a hint of pushed up cleavage below his falsies, which were held firmly in the strapless, firm underwire bra, and the dress was form fitting all the way down as it ended mid-thigh. On his legs he wore sheer black stockings and on his feet were 5 inch sling back pumps with a matching velvet pointy toe and a thin rhinestone strap around his ankles. His hair had been all swept to one side and arranged in two distinct waves in front, before the rest of the long layers were twisted into a perfect chignon behind his left ear. From each ear hung an oversized large crystal teardrop earring, and across his right wrist was an elegant tennis bracelet. His big lashes were back, fronting his perfectly melded rose lids and cheeks but the highlight of his face was obvious, with not to be missed cherry red lustrous lip stain. He knew he was dressed for evening as he arrived as his car dropped him at Tavern on The Green. He wished he had a coat as he exited the car, feeling the slight chill in the air, but with his hair mostly secured in the chignon and his dress very form fitting ,the wind could do little damage. He walked in ready to work one last time at an after hour social, looking around for his event. "I can't seem to find our corporate event?" said Alan to a receptionist until he felt a hand on his shoulder. "I'm not aware of any corporate events this evening miss?" said the receptionist. "No need to look, she's with me," said Robert ,startling him. "Can we be seated now?" Alan gave Robert a strange look as he held out his forearm like he had weeks before. Alan had little choice, taking his arm as they walked into another room, as suddenly he realized they were about to be seated at a center table overlooking the gardens. As they stopped at the table, Robert tipped the hostess and then pulled out Alan's chair as they sat down. He snapped his fingers as a waiter came over and smiled, looking at Alan. "Your finest champagne, please," said Robert. "This is a thank you for all your hard work, and if you don't mind me saying, you look absolutely stunning tonight." "Oh, thanks," Alan replied as the waiter poured the champagne. "To the west coast, and a new start," said Robert, raising his glass. "Yes, cheers. I wish you the best of luck," said Alan. "Thank you Alicia," said Robert as they sipped. "This tastes as beautiful as you look, Alicia." "Wow, uummmm thanks again," said Alan, downing his drink and having no idea what to stay, worrying now that Robert might have the wrong idea and knowing he was certainly not at a business event. "So Alicia, I thought you'd enjoy celebrating with me because working with you has been my pleasure," said Robert. "I know you may not be expecting this, but I was hoping we could take our relationship further than just business." " Robert, sir?" Alan stuttered. "This will be really awkward, but I thought you knew my situation. I'm sorry I made a bad assumption, as obviously your dad knows everything, so please don't feel bad about what I'm about to say Robert. Well I'm really not Alicia, and in fact tomorrow is Alicia's last day. My name is Alan, and I'm actually a man." Robert was now laughing as Alan felt relieved, getting it off his chest. "Oh, you took that well," said Alan, sharing a laugh now. "Thank goodness you're not mad, and I'm not fired right?" "Of course not," said Robert, still chuckling. "Good, because I thought for a moment you were pursuing me," Alan chuckled. "You know with all the nice comments. I thought you wanted a date." "I didn't want one," said Robert, as Alan felt him rubbing his leg under the table. "This is one." "I'm sorry?" said Alan, confused. "I know I'm blonde, but it's not natural, sir. What did you say?" "I said this is a date," said Robert. "Relax, its fine. No one knows but us. Claire thinks you are handling a small business function that I set up, and I sent them the little black dress. You see ,you're my type. I've always had a thing for she males, and you're a rare find. Honestly you're exquisite, Alicia. I know the whole story about the bet and that tomorrow's your last day as a girl, but I don't want it to be. I'm here to offer you a job with me in the new west coast office as Alicia, with the opportunity to spend more time together. The timing couldn't be better for us to discover each other. I think you'll be amazed how exciting our relationship could be as you continue to develop as a woman." "You mean as a full time woman?" said Alan, stunned. "Yes, and as my girlfriend and with any job you want. Be the office manager or my secretary or go back in sales if you want. With your looks, you be an amazing saleswoman. Work whatever schedule you want or don't work at all and just stay home, looking gorgeous," said Robert, reaching his hand under the table and up Alan's skirt between his thighs. "I'm rich Alicia, so it doesn't matter. You'll have everything you've ever wanted and I'll have you. I leave tonight on my private jet and I want you with me." "Robert, please!" whined Alan. "What you're asking is crazy. This was all temporary. It was a bet." "I know it's happening so fast," said Robert squeezing gently. "I know you didn't expect it." "I gotta go," said Alan, getting up. "Wait, you're making a mistake," said Robert, grabbing his wrist. "You're not thinking clearly. This chance won't come again Alicia." "Alicia's got one day left," said Alan as he turned to leave. "I'm out of here." "Alicia, wait," Robert grabbed him. Alan wasn't expecting it as Robert pulled him in, dipping him back and pressed his lips on his as he wobbled to keep his balance on the edge of his heels as Robert held him. He was dominating the kiss as Alan was fighting him off as he felt Robert try to slip his tongue into his mouth as he was finally able to turn his cheek away. Alan was stunned as Robert lifted him back to his feet and removed his arms from around him as Alan gathered himself. Instantly, he felt like he was going to puke, seeing his lipstick all over Robert's face as Robert was smiling, looking into his eyes. "Are you insane!" screamed Alan, pushing him back and causing a scene as people turned, looking at them now. Robert stood there embarrassed, not expecting the scene as Alan turned away. He was practically running in heels as best he could and jumped into the first cab he saw. He couldn't believe what happened as he hurried home, immediately running into the bathroom and brushing his teeth. He felt better taking a shower and was in bed in no time. He had a hard time sleeping after the incident, but was up early excited about his last day as a secretary. It was an incredible feeling as he opened his closet, seeing the last new blouse he had never worn, taking it from the hanger. He was pretty good at getting ready now and had it down to a science as he got himself ready and headed to work. "Well, last day Alicia," said Claire. "I've arranged a meeting with human resources at 4pm to process all your forms so I'll expect you'll work through lunch, and then go to that meeting." She was tough, down to his last moment, never letting him rest for a moment. The other secretaries were sad to see him leave the pool, all hugging him until he headed to his meeting. As he got there, the receptionist ushered him in and he was surprised to see Mr. Cappa sitting there and not the human resource manager. "Sir, I didn't expect you here," said Alan. "Sit down, Alicia," said Mr. Cappa, tossing a series of documents on the desk. "I realize that. I need you to look at these documents and do some explaining, please." "What is all this?" said Alan, scrolling through all the statements and receipts. "I guess the receipts are for dresses and jewellery, but the rest are bank statements. They're mine, but they're not right sir. No way did I deposit all this money, and I didn't realize what all this cost." "You didn't?" said Mr. Cappa. "You wear an Armani suit and that's the receipt for it. You used my corporate account and bought eight grand in clothing. You also bought four thousand in jewellery, and I paid for your nails!" "I'm sorry. I didn't know," said Alan. "I'll pay for it. I thought those were my cards. I'll be taking everything back immediately." "And what about the eighty grand missing from my west coast operating account that now seems to be in yours," said Mr. Cappa. "Can you explain that?" "Sir, wait that is crazy," said Alan. "I wouldn't steal." "But apparently Alicia would," said Mr. Cappa, picking up the phone. "Gentlemen, come in please." Alan was stunned as two officers came in and he soon found himself in handcuffs. "Sir, please, I didn't do this!" whined Alan as his boss ignored him. "Take her out the back door," said Mr. Cappa. "I don't want my company shamed!" Alan was tearing up as he found himself cuffed in the back of a car. He was brought to a local jail and disgraced as he was strip searched before redressing and being thrown in a cell with a series of scuzzy men. "Oh yeah. Aren't you a sweetie?" said one of the cellmates as Alan tried finding a corner. "Thanks for the gift." "You must be an expensive type butch?" said another cellmate. "But I guess you'll be free tonight won't you?" They tried numerous times touching and feeling him as he shoved them away and tried keeping to himself. His calls to the officers on duty were ignored until finally he was brought to the office as an attorney entered and hit a button on the speaker phone. "Are you ok, Alicia?" said the voice. "Robert?" said Alan. "Honey, let me make this all go away," said Robert. "I sent my attorney there and he can help find you a good lawyer if you want, but hopefully that won't be necessary. We can settle this easily if you'll cooperate." "Did you do this to me?" screamed Alan. "You son of a bitch!" "Honey, calm down," said Robert. "Actually you did it to yourself. All those receipts and deposits are your signature honey. You should have paid better attention and been less blonde, my dear. Everything that happened you actually did!" The attorney laid out everything on the table as Alan rummaged through it all. He saw his signature on deposits and tons of credit card slips. "You know I didn't do this," whined Alan. "I trusted you, and this was all because I was exhausted. You and Claire worked me to the bone!" "But not anymore, and all Claire did was her job. Our relationship has nothing to do with her and neither are our feelings for each other," said Robert as his attorney dropped a series of forms in front of him. "Sign and you'll be out of there. I'm in love with you, and I'll take care of you the way someone special like you should be taken care of. Read it. It's a one year deal. After one year if you're not happy, then you can leave me and you'll be rich. Sign it and you'll be out of there in thirty minutes and all you have to give me is one year." "You're really crazy!" said Alan. "A year as a woman! And if I didn't?" "Then I'm sorry but you're on your own, my dear," said Robert. "Either way you won't be a virgin much longer my lovely Alicia, but wouldn't you rather it be in a loving situation?" "Fuck you Robert!" screamed Alan, slamming down the phone, cutting him off. "Here's my card in case you change your mind," said his attorney as he left. "You've got one call." The attorney left and an officer came in, dropping an orange jumpsuit on the table. "Put this on and put your clothes in the bag," said the officer. "Keep on your underwear and shoes." "But all I have are heels," said Alan. "Not my problem," said the officer, walking out. "Everything in the bag but underwear please, and it will be placed with your purse and possessions." Alan changed and was brought back to his cell. It was now later in the evening and crowed with criminals and derelicts, and it wasn't long before they couldn't keep their hands off him. "I'm digging butch in the jumpsuit and pumps," said a cellmate. "I'm first homies!" Suddenly, Alan found himself fending them off as the officers ignored them, laughing as Alan cried as they tried having their way with him. "Please, I can't," whined Alan as some sperm squirted into his right eye. "I need my phone call. I need it now!" The officers were laughing and let him suffer a little longer as the only thing that saved him being raped was his orange jumpsuit. It was torn now as they almost had it off him as he had two black eyes and was beaten up pretty well before the officers finally opening the cell and pulled him out as he made his phone call. He sat back battered and bruised, and before he knew it he was on a gurney signing some forms as they took him in an ambulance and finally he passed out from medication. "Wake up Alicia," said a voice. "You ok?" "Pam?" said Alan. "Hey honey," said Pam squeezing his hand. "What are you doing here?" said Alan. "I thought you left me!" "You sent for me honey," said Pam. "I'm honored you did ,truthfully, and I wouldn't miss this, but I'm sure you know what you're doing. I'll get Olga and Hannah for you as it's almost time." "Rise and shine Alicia," said Claire, coming over. "It's an exciting day, isn't it?" "Exciting?" said Alan, lifting his arm from under a sheet that covered him in his chair, and rubbing his eyes. "Yes, it's the big day of course," said Claire. "You've been recuperating for two weeks now, but you look amazing. Don't you remember anything?" "A lot of bad dreams I think," said Alan. "Well they'll be turning to sweet dreams in a few minutes," said Claire, taking his hand. "Trust me, half the girls from the office are jealous, and relax, you look beautiful. I hope I look half as good as you do on my wedding day!" "Wedding day? Holy shit!" screamed Alan, standing up as the sheet fell off. "And holy shit. Are these real now!" "Well, real is relative, right?" said Claire as Alan grabbed his breasts. "Real compared to the glued on ones you had before, yes! And look at it this way, they're as real as most of the other enhanced blonde beauties have out here on the west coast. In fact, I'm sure yours are better than most." Alan was stunned, feeling the some sensations through his body as he touched his new boobs. He looked down, seeing them firmly held in the white strapless bustier that circled his midsection and then glanced down even further, seeing the garter straps and sheer white stockings. He stretched his neck and reached down, grabbing his limp manhood as Claire rubbed his back, comforting him. "Relax, it's all still there," said Claire. "You make a beautiful she- male." "Claire, get me out of here," whined Alan. "Please help me. I'll do anything." "Yeah right, and risk my career for you?" Claire chuckled, and pointing over to the closed circuit cameras. "You chose all this and there are cops everywhere. Robert always gets what he wants, and luckily for you he wants you! Now here come the girls, so let's get you dressed." "Claire, please," whined Alan as she covered his lips with her finger. "I'd shut my mouth if I was you," said Claire, whispering in his ear. "They are listening. This room is bugged." Alan looked down, seeing all the cops guarding doors and exits on the monitors, as Pam re-entered with Olga and Hannah now. They were all in matching long red bridesmaid dresses, as he began shaking as they approached. Hannah took her brushes, sliding them across his cheeks and then took some powder to his face. Olga now knelt in front of him, opening a box as he looked down, seeing his feet being inserted into 4 inch white satin pumps as he could feel a huge knot in his stomach. He looked over staring at the monitors until he was distracted by the sound of a zipper as Claire and Pam each took an arm as Olga knelt in front of him lifting his right leg. "Don't peek. The reveal will be worth it," said Claire, lifting his chin as he felt the other leg lifted. He was quivering beyond control now as he felt the dress slide up his body and the zipper creep up his back. Olga walked behind him now as he felt some itching across his shoulders and then some scratching on each side of his scalp. Within a moment, she was looking directly into his eyes, taking beige pin after pin from between her clenched teeth and inserting them onto his head until finally she let out a huge smile and stepped back. "We'll give you a minute, dear," said Olga. "Vera Wang always knows how to take your breath away and you're no different. You look amazing!" "See you out there Alicia," said Claire, releasing his chin. Alan was completely stunned as he turned as the girls scurried from the room. He looked down, seeing his huge cleavage framed in the strapless cups of the white dress. He was visibly thinner than he had ever been, and he couldn't believe it was him he was staring at, as he looked over his shoulder seeing the floor length mirror as he turned, getting the full reveal. His dress was a strapless ivory taffeta Vera Wang wedding gown with an asymmetrically draped bodice, scooped neckline and a full ball gown tulle skirt. The huge poofy skirt hid any bulge he had, as did the tight white satin and lace panties he was wearing. His makeup looked flawless, with huge perfect lashes, simple creamy natural shadows, and his lips were a glasslike glossed candy apple red. In his ears were elegant teardrop pearl earrings, and he had on no other jewelry beyond the large diamond engagement ring on his left ring finger. His blonde hair had been gelled back and arranged in a rather basic high rounded, yet oversized pumped up bun with not a hair out of place. The base of the bun was surrounded in white pearls and baby's breath flowers, before being engulfed in a long sheer veil which streamed all the way down his back and swept a few feet behind him on the floor. "I'd stare at myself too if I was that beautiful," said a voice, startling Alan. "Mr. Cappa." Alan twisted to see him. "It's time Alicia," said Mr. Cappa, coming over and taking both of Alan's hands, looking into his eyes. "I'll be giving you away to my son. You made the right decision, dear." "Sir I--". said Alan as Mr. Cappa shushed him with his finger and then pulled down his veil. "You can start calling me dad when we're not at work, my dear," said Mr. Cappa, taking Alan's hand and placing it on his forearm as he began pulling him from the room. Alan looked up now, trembling as he watched the procession of bridesmaids walking down the aisle as he found himself being dragged by Mr. Cappa. He looked around, knowing most of the faces of people from work, as he knew all eyes were on him. He could see his former friends from sales chuckling as he almost pulled away to run before seeing the guards at the exits. He finally looked up and ahead, realizing he was now at the altar, seeing Robert grinning from ear to ear as they stopped walking. "Don't be nervous, he'll take good care of you monetarily, and in the bedroom. Trust me, I'm happy it worked out for you two," said Mr. Cappa, whispering in his ear. "It'll be much more economical than paying for all his she-male hookers every week, and you'll make a fine wife. I'll expect you to make my son very happy Alicia, so we don't need to revisit any of your prior sins." "Dearly beloved....." said the minister as Alan looked over at Robert, who was smiling. He clutched his bouquet tightly and took a few deep breaths. Before he knew it, he was mumbling when Robert squeezed his hand and a ring was sliding over his finger. He was frozen as his veil was being lifted, clearing his vision and he knew there was no turning back as he watched Robert's lips move in, feeling his first kiss as Mrs. Robert Cappa.

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My Wife Found Me A New Secretary

I’ve always had a great fondness for women.  I’ve always had a roving eye most of my adult life.  My wife and I married right out of college.  She saw a good thing and wanted to get married right away.  I wanted to wait a little while.  However, she talked me into getting married.  We’ve been married for twenty years.  We never had children, which I believe put a strain on our marriage.  My wife found out early, she couldn’t conceive.  She didn’t want to adopt.  Don’t get me wrong, I love my...

Cheating
3 years ago
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Dons New Secretary

Don's New Secretary By Kathi J Don was awakened by his alarm on this hot July morning. He had gotten to bed late last night and was a little groggy. He hopped straight out of bed and started his daily routine: shit, shower and shave. He gave himself the extra time to soak in the hot shower before exiting and getting ready for work. Once showered, he headed into the bedroom. He donned his conservative gray business suit, tie, black socks, black dress shoes and gathered his...

1 year ago
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Business partner to pretty sissy secretary

It was embarrassing. As all the men stared at my now smooth pale girlish body. "My girlish body?!" How could this happen? I wanted to run away. But my male psyche couldn't control my own body anymore, I felt consumed by my female psyche. As I uncontrollably danced for what I thought was my "business partners." They fooled me slowly, asking to do small tasks that we're meant for secretary type instead of a business partner. It was small things at 1st, getting coffee or...

2 years ago
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The New Secretary

The New Secretary Part 1 I sat reviewing the application in front of me. "This is the last candidate; Ms Tiffany Monroe. Let's get her in and then we can think about which one we want." Denise, the HR Manager, nodded and left the room. I sat, waiting and wondering what this Tiffany Monroe was going to be like; in the end I gave up as, more often than not, the name and details on the application bore no resemblance whatever to the person who sat before you. With Tiffany it was...

1 year ago
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New Secretary

About 2 years ago, my personal secretary Sunita got married & migrated to Australia with her husband, who was working as a software engineer in Melborne, I was so used to her looking after my appointments & other office chores, that with her leaving, I was in total chaos after her exit, I needed a new secretary, so I decided to spread the word in my business & friend circles, so that I get, just the candidate I was looking for. After 4 days at about 11.00 am, my receptionist called me on the...

4 years ago
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Banging The Secretary

Debra West was a secretary at Bold Industries, which was a construction firm.  She was not the sharpest tool in the shed, but she had a great body, and her boss liked looking at her.  She made mistakes most days but yesterday made the biggest mistake of all.  Her boss Mr. Johnson had her doing personal tasks for him.  She was to order flowers for his wife and his girlfriend but sent the wrong flowers to his wife.It was his wedding anniversary, and the anniversary flowers went to his girlfriend,...

Office Sex
4 years ago
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Sex With the New Secretary

Last week was a week full of celebratory events. Agatha Smith finally retired. She gave thirty years of service at Anthony Roma’s company. He made sure that she got a nice pension and his company gave her a retirement party. She was the best administrative secretary he ever had. The best part of her retirement was interviewing dumb blondes to take her place. There were many that were perfectly qualified. Mr. Roma wasn’t really looking for somebody who would be able to get her work done...

2 years ago
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Part 18 Sex with lactating secretary

Sajitha was a departmental secretary in our company. Upon my transfer or deputation to Mumbai as one might want to call it, she was assigned to me for some time in addition to her usual roles. While she did not belong to my department, half her time was to be with me. I was on an important mission to this office and I had clear directives as to what was expected of me. To work better I had requested for a helping hand to take care of the mundane matters like getting tea/coffee, taking meeting...

1 year ago
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Wizards Day Off The Secretary

The wizard sat on the park bench reading his paper. He was very much enjoying his day off. A man sat down next to him on the bench and forcefully dialed a number on his cell phone. He did not look happy but the wizard continued reading the paper, this was his day off after all. The wizard heard a squeaky voice on the other end answer and the man cut her off. "Britney, I am almost finished with my lunch break. Have you completed my report for corporate yet?" "What do you mean you are...

1 year ago
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Sissy Secretary

I guided them down the back staircase into the media room with its plush movie theater seats and a wall sized digital screen. My pride and joy, "And that," I said with a grand sweeping gesture and deep bow worthy of a carnival ringmaster, "is the tour of my humble abode." "Yes 'humble'," Maria Sanchez said elbowing her husband playfully in the ribs, "we should be able to afford so 'humble'. And here we thought living right off the golf course was nice." Her husband Ben defensively...

1 year ago
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application for secretary

Heather showed up at Margaret's office at nine sharp the next morning for her interview. I was in Margaret's office sipping at a cup of french vanilla cappuccino and Margaret was having a cup of coffee. Heather came in and introduced herself to us. She was wearing a very curly blonde wig that fell to the middle of her back, and she also had on a loose fitting white blouse, a knee length black skirt, white stockings and black five inch heels. Margaret directed Heather to sit in the chair by...

3 years ago
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Daddys Little Secretary

I recently was asked to become a partner at my law firm. Now, it’s not a very large firm maybe fifty or so attorney’s each of us have assistants and there’s about fifteen or so paralegals. We’re a pretty well knit family the majority of us have been working together for about a decade. As a matter fact my career started here before passing the bar. Before starting law school I was working as a paralegal for the firm. So, to go from a paralegal to a partner in just a decade is pretty...

3 years ago
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Georges secretary

My sweet girlfriend Laura looked upset during lunch time…I asked what problem she had and Laura leaned on the table, looked at me with her very nice green eyes and hissed:“George is cheating on me with that stupid bimbo secretary…”I insisted, asking her if she was sure or just she suspected the whole matter. But Laura then got even angrier and furious…“The bitch is the new girl in the office; I met her two weeks ago…”“A little slut bimbo in her early twenties; a sensual brunette, some killer...

2 years ago
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Rita my New Secretary

I'll start by telling you that this isn't a true story and began by telling you that I'm a small business owner and my name is Dave and I 'm the owner of a reality business and right in the middle of our busiest time of the year my secretary Lisa comes into my office one morning and tells me she's giving her two weeks notice as she's accepted another job offer that Offers more money and is closer to home!! So the next day I place an add in the classified's section of our local paper advertising...

3 years ago
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Black Politician Breeds Married White Press Secretary

Race relations in the United States have improved markedly since the 1960s, although some blacks and whites still have lingering prejudices, especially in the South. I’ll admit that even being born in Alabama in 1988, and raised in the 1990s and early 2000s, many of my family and neighbors still held resentments from the racial strife in the 1960s. I tried to rise above those influences, but it was difficult.My name is Avery, and after high school I attended a moderately-liberal college in...

Interracial
1 year ago
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Stripper to Special Secretary

I really need a job. It has been two months since I was fired from my last job as a stripper and I am running low on money. I was let go because the place I worked at, Dancing Dames, was not doing well and they needed to let half of their workers go. I have looked at other strip clubs, but I want to try something new. Work though, has been hard to find, considering most of my experience is in taking off my clothes and giving lap dances. So over the weeks I have become more and more desperate...

Office Sex
1 year ago
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Banging My Horny Secretary

Hello ISS readers. This is my third story on ISS and in this story i am going to tell you about the experience about how i got to fuck my extremely hot and mature secretary. We had shifted to Singapore two years ago and after joining the office, i first met her. My boss introduced her and told that she was to be my personal secretary. She was a beautiful woman, about 38 years of age, not so fat. Her assets were beautiful. She had a nice pair of round breasts and a firm tight ass. She was...

2 years ago
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The New Secretary

The New Secretary (inspired by Masked Scribe's The Secretary from the yahoo maskingwriter group) Eric Lindsey got up, struggling to get open his eyes. But when he saw the time-1120am, he got real quick. Oh crap, I am nearly late for my next interview this afternoon. He leapt out of bed and after taking off his sleepwear, he gathered his materials for the interview. Sure, the last job he had was fun and all, but he yearned for more excitement. There existed a thrill to becoming a female...

1 year ago
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Secretary

Secretary1        It was Friday near quitting time when the E-mail showed up from my boss.         Kelly,        I think this would be a good time for you to invest in some job security, come into my office and be prepared to learn all of the tricks to being an exemplary subordinate.         Mr. Blalock had been hinting since he had hired me that I should be doing him in order to keep my job.  Unfortunately, just as with the E-mail I had just received his hints were just vague enough that...

3 years ago
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From Salesman to Secretary

Chapter 1: Reunion "Hey James, you ready to interview this new secretary?" James looked up from his laptop and saw Dave, his boss. "I'm a bit swamped right now, would you be up for doing it solo?" he said to him. He had been working full on all day but was ever so slightly behind. "Sure, thing no problem, you keep doing what you do best!" And off he went. Dave was a tall handsome man that made a good boss. He wasn't too tough and he had a very friendly attitude, it made the...

1 year ago
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My hot Secretary

Miller and sons. The 3rd largest law firm on the west coast. I've worked for the firm the past eighteen years. Started out in the mailroom at seventeen years old. Why might someone get into law you ask? Because my father did it. And so did my grandfather. I was holding court in my living room at age ten. Didn't really have much chance of being anything else. I wanted to be a rock star. But there is the problem of needing musician talent. Which I didn't have. There's always a catch. By...

2 years ago
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Julie the secretary

A fantasy inspired by amateur_julie containing office related frolics...My job sees me travelling around the country on a freelance basis going to various companies fixing IT problems as and when they arise. I'm never in any one place longer than a week. It's not the sort of working life that everyone would take to - hardly ever seeing the same faces, but it suits me as I can choose to work when and where I need to. A few months ago my agency sent me to a company not far outside of London for a...

4 years ago
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Kelly Woods The Young Secretary

Kelly Woods needed this job desperately. Her husband, Todd, becameanother victim of the worst economy since the Great Depression. With onlyher income now, the newly married couple barely made their rent and carpayments. If she lost her job too, eviction from their apartment andrepossession of their car threatened to leave them destitute. Fortunately,John Simpson, the owner of Franks and Simpson Marketing where she worked,was a kindly old gentleman who liked her. Although others...

3 years ago
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Master Johns Sissy Secretary

Master John's Sissy Secretary by Melissa FCD The intercom buzzes and my boss's voice booms out loud and clear. "Melissa I want you in here in ten minutes to take dictation. And bring me some coffee." "Yes sir Mr. Thomas, I'll be in there in ten minutes with your coffee sir" I reply. I get up to make a fresh pot of coffee. As I walk to the coffee maker my suntan colored nylons rub against each other at my thighs making a soft whispering sound. My four inch navy pumps...

1 year ago
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A Special Secretary

I look up as the suave middle-aged man waltzes into the office, suit immaculate and just enough stubble to appear roguish, but not unkempt. "Rogers. Harrison Rogers," he says to me, frowning slightly. He is surprised - they always are. Why on earth would a successful businessman like Gerald Hammersmith have a male secretary, after all? I watch as Rogers's eyes narrow, then he gives the usual slight shake of his head, and then a shrug. They all go through the same thought process: is...

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