The Bored Secretary free porn video

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The Bored Secretary Belladonna Jerome Gustafsson tapped the butt of his pen against the desktop as he stared at the clock of his computer screen. Another minute clicked by while he awaited the arrival of Lily Ghosn into his home office. It was one of the few places Lily had never been in his home before. She was his wife's best friend for decades. She had been the Maid of Honor at their wedding. He cared for the girl, even though he detested her forced intrusion into his business life. It had been more than a decade since Jerome had turned away from the world. He stopped going to his office and began to work strictly from home. Some of his former associates believed that he was a germaphobe, while others thought that he was sick and did not want them to see what was ravaging his body. His explanation to his wife, however, was that he simply had tired of social niceties and rules that had constrained him. Jerome's wealth saw to it that he never had to work again. He could be as reclusive as he wanted to be without any issue. Still, he maintained the reigns of his company from the comfort of his home without ever having to visit with those that carried out his orders. The home office he had built comprised a separate wing of the home. It allowed him even greater privacy than the rest of the house, which his wife frequently brought friends and family into to force Jerome to have social contact with someone other than her. While Jerome was a recluse, his wife remained a social butterfly. Gloria sat on a number of charitable foundation boards and served as his only contact with former associates from the business world that he, now, paid others to deal with. A recent trip and fall had ended his seclusion during his work hours, however. While he did nothing more than sprain his knee, Gloria threatened him with divorce if he did not agree to hire an assistant to be on hand in case anything went physically wrong with him during the day. He felt it was wholly unnecessary. He simply could not explain the real reason for his fall. He was sure that Gloria would never get the image of him tripping in high heels over her white poodle out of her head if he put it there. In Gloria's eyes, Lily was the perfect choice to make sure that he was not left dead at his desk for hours. Jerome tried to fight the choice, but his wife would not let him say no since her friend needed the money that they had to spare. Jerome's efforts were met with dismissive words from his wife before she invoked her part ownership of the company. It was something that was rarely mentioned. She had always been the silent partner since the company was started with a loan from her father. Jerome was not used to her taking the lead on something, but she was set on her decision and was not leaving him with any option. The sound of a knock on the door was followed by the sound of the door creeping open. He heard high-heeled footsteps on the wood flooring before Lily called out, "Jerome? Are you here?" "No," Jerome answered. "Very funny," Lily replied, following the sound of his voice through the wing of the home. Lily gazed around the cherry wood paneled walls of the office. Her eyes were drawn to the crown molding along the edges of the cathedral ceilings throughout the central room that was furnished with an area rug, fireplace, table and leather chair. She shook her head at the original paintings that hung on the walls, figuring that only Jerome and his wife's eyes had glanced at their beauty since they were hung. In the back of the room there was a half wall that concealed a copier with another room beyond it. An office had been carved out next to the central corridor. She saw the only natural light in the home office shinning into the room she approached, catching a glimpse of the out of place desk that had been situated outside the door in the process of readying the office for her arrival. The secretary's desk was the only thing that struck her as not having been the product of careful planning and needless expense. Lily stopped in the doorway and said, "Good morning, Jerome." "Lily," Jerome replied before he turned and saw her outfit. Pangs of jealousy stirred in him while he looked at the girl who was dressed so similarly to the way he would be if she was not due in that morning. "How are you?" Lily asked. "Good," Jerome replied, feeling that he would be better if he was standing in her beige, almond toe pumps and matching beige, pleated, a- line skirt. "Is there anything I can do for you?" Lily asked, slightly miffed that Jerome did not ask how she was given their long-standing personal relationship. Jerome shook his head in reply. "Really nothing," Lily responded, her smiling leaving her face as she did so with a shake of her head. Jerome shrugged before he said, "You can get me a cup of coffee from the kitchen, if you want." "I'm on it," Lily replied with a grin before inquiring how he took his coffee. Jerome gave her his order before he turned his attention to his work. Jerome shook his head while he heard Lily's heels clicking as she made her way out the door into the main part of the home. Jerome seethed, knowing that it was his heels that should be clicking on the floor, even though it was his shoe fetish that got him into his troubles. Jerome stared blankly at the screen as he resolved to carry out his plan. He planned to give Lily no work. He was going to make her sit quietly at her desk. He was sure that she would quit from boredom and give him back his feminized solitude in short order. Lily walked back into his office and gave him a cup of coffee before she asked for her next task. Jerome shook his head in response and said he was not busy and had nothing for her. Despite her attempts to press him for more, Jerome did not waiver. Giving up, Lily walked out of his office and into the central room. She stared around the room until she went into the home and came back with cleaning materials. Jerome heard her scurrying about as she dusted and polished the items in his office, opening the wood blinds that had not been opened in years in the process. Jerome scowled while he cursed her efforts to be productive. He wanted to tell her to stop, but he knew he risked his wife's rebuke if he did so. Jerome worked through it until lunch. Deciding to take advantage of a person willing to travel outside, Jerome had Lily order his lunch and go pick it up. With her out of the office, Jerome slipped his black, sheer pantyhose covered feet out of his oxfords and into a pair of grey, patent leather heels with a three inch spiked heel that he kept locked in his desk. Jerome felt more at ease as he worked with his feet in their normal, perched working position. For a moment, everything felt right to Jerome. He hiked up the cuffs of his pants to glance at his heels and tights covered ankles. His untucked manhood swelled, pressing against the waistband of his control top pantyhose as he kept stealing glances of his feet while he worked in her absence. Around the time he figured Lily would return, Jerome slipped off his heels and locked them away again. With a grimace, Jerome placed on his oxfords. He shook his head at them, hating their utilitarian appearance that fit with the rest of the drab outfit he was forced to wear in Lily's presence. After she dropped of the meal in his office, Jerome ate at his desk in silence. Lily ate her lunch and took to cleaning the floors of the home office. Jerome shook his head at her continued labors. He was sure that it would only preoccupy her for a day at most, however, so he was confident that she would quit from boredom soon enough. As she cleaned the area around the copier, Lily stared at the closed door behind it. She approached it and noticed the keypad on the door. She tried to push the door lever down, but found it was locked. Intrigued, Lily put down her cleaning supplies and headed for Jerome's office. A knock on the door brought Jerome's gaze to the doorway. "What's going on?" Jerome inquired. "I was cleaning behind the copier, and I noticed a door on the back wall." "Okay." "The door's locked. I want to clean in there." "The door's locked for a reason," Jerome countered. "Oh." "That room is where I keep my most sensitive information." "So keep out?" Lily asked with a smile. "Keep out and keep away," Jerome replied, turning his attention back to his work that struck him as duller than ever without the familiar feelings of feminine finery hugging his body. Lily nodded before she returned to cleaning and finished working for the day. When she returned the next day, Jerome persisted in giving her nothing more to do than fetch him two cups of coffee and pickup his lunch. Three weeks passed with the same routine of Lily doing little or nothing, broken up only by her occasional cleaning of the office. Jerome was perplexed why the girl refused to quit. He felt that his boredom was enough to make him want to retire, and he was the one doing some actual work. Jerome's urge to recapture what he lost grew with each day he was forced to wear men's clothing in his home office. The lost release he got daily was weighing on him as he sat at his desk ruing the fact that he could no longer play the role of a woman as he did when his wife was away and he was left to work from home alone for years on end. Jerome was growing desperate when he called Lily into his office at the start of the workday. Lily grinned as she said, "Let me guess, you need a coffee, right?" Jerome shook his head as he said, "Lily, I'm getting a little restless here." Lily gave Jerome a curious glance as she said, "Okay, what do you want to do about it?" "I want to know if you're up for a little game." "Jerome Gustafsson plays games?" Lily replied with mock surprise that concealed a genuine layer of intrigue. "Yes, I do." "I didn't know that. You were always so serious." "There's two sides to every coin," Jerome countered before he added, "So, I was wondering..." "What?" Lily asked as Jerome pondered whether he should continue. Deciding he must, Jerome said, "Would you like to switch jobs with me today?" "Come again?" Lily inquired, confused by the request. "I was thinking you could be me for a while, and I'll be you," Jerome replied, paraphrasing the lyrics from one of his favorite songs from his young adulthood. Lily raised an eyebrow at Jerome's words before she asked, "How would that even work?" "I've got little to do at my desk, so why don't you take a seat and I'll handle your job." "What do I do?" Lily inquired, making sure to point out that she did not feel that she had a role to swap. "Why don't you show me?" A grin came to Lily's face as she said, "Okay, I accept." "You do?" "Maybe it'll be a little less boring for me today," Lily replied, hoping that the days events would stir Jerome to giving her more responsibilities. "I think you're right. Everyone needs a change of pace every once in a while." Lily nodded as she approached Jerome and said, "Get up." Jerome complied before Lily scooted by him and took a seat in his chair. "This is nice," Lily remarked while she wiggled her pencil skirt clad rear against the seat of Jerome's chair. "I paid for extra padding." "My ass thanks you," Lily joked in reply. Jerome laughed before he replied, "Now, is there anything you need, Ms. Ghosn?" "Oh, so formal, Jerome. Ms. Ghosn? I like the sound of that. Take care to make sure that you keep calling me that," Lily chided with a grin. "Will do, Ms. Ghosn," Jerome replied as his member stirred at her faux stern tone. Lily leaned back in her chair as she said, "Well, I think I should start the day off the way you would if you were the boss. Jerome, please get me a cup of coffee?" "How would you like it?" "With milk and a little sugar." "I'm on it," Jerome replied. "I'm on it, what?" Lily teased. "I'm on it, Ms. Ghosn," Jerome answered with a grin and a burgeoning erection. "That's better," Lily said before she gave him a dismissive wave and looked at the computer screen in front of her. She focused on the simple spreadsheet Jerome left up in front of her while Jerome scurried out of the home office and towards the home's kitchen. Jerome felt the pull of the garters on the nude stockings covering most of his legs with each step. Jerome grinned at the feeling, loving the uniquely feminine sensation. Still, it was only the feeling of the stockings, panties, garters and garter belt he was wearing that gave him any taste of the feminine clothing he wished he was clad with at that moment. Jerome went to the individual coffee brewer that his wife had recently bought to replace their old one. He clasped a cup and placed it in the machine. As he let the machine brew Lily's cup, Jerome's mind drifted. He fantasized of being ordered about by her in a skirt and heels, but he knew it could never be. Any hint of it would make his way to his wife, who he was certain would divorce him on the spot if she got wind of it. Gloria was already unhappy about his reclusive nature. She was a social person. She lived a social life despite him. She wanted him to come along with her to her events. She teased him about the men she said hit on her because no one believed she was still married since Jerome would never show his face with her. Despite her efforts, Jerome was inflexible on the issue. Once the machine stopped brewing, Jerome took hold of the cup and retrieved the milk. He added a little milk to the cup before putting in a little sugar. A smile came to his face as he carried the cup back towards the home office. He felt like he really was a secretary as he pushed the door to the home office open. Jerome walked towards his office door and paused, waiting for Lily to acknowledge him. Lily turned away from the spreadsheet. She smiled at Jerome before he entered and placed the cup down in front of her. Lily thanked Jerome before she took a sip and grimaced. Jerome gave her a curious look as she inquired, "What's wrong?" "This coffee is too dark. Add some more milk." "Okay," Jerome replied, confused by her undisguised order. "Please state that properly," Lily added. "Huh?" "Tell me you'll fix your mistake," Lily answered. "Oh, I'm sorry, Miss Ghosn. I'll fix my mistake," Jerome replied, feeling more excitement than he had since he fell in the office. Lily nodded before Jerome took hold of her cup. He was aroused by the chiding he received. He felt more like a secretary than he ever imagined he would when he sometimes played the part for an imaginary boss. His heart raced while he went back to the kitchen to add more milk to Lily's cup. After retrieving the milk from the refrigerator, Jerome added the milk to the cup. He put it back away and walked back through the home office. Jerome stood in the doorway of his office once more, trying to hide his excitement. He approached Lily once she acknowledged his presence again. Lily took the cup from him and took another sip. Another grimace came upon her face. "What's wrong, now?" "This is like milk with coffee in it, now." "Oh, I'm sorry," Jerome replied, taken aback by her continued criticism of his inability to make her a satisfactory cup of coffee. Lily grinned, enjoying acting like a demanding boss before she teased, "Okay, here's the deal. You made one with too much milk, one with too little, so, why don't you make the next one just right." Jerome blushed at her childish reprimand while he took the cup and said, "I'll make you another cup, Ms. Ghosn." "You'll make it just right?" Lily inquired. "I'll make it just right, Ms. Ghosn," Jerome answered. Lily dismissed him to make the cup. She saw the grin coming upon his face while he exited the room. Leaning back in her executive's chair, she laughed to herself as she thought, 'He may actually be enjoying this more than I am.' Jerome's manhood was at its firmest as it pressed against his soft satin panties while he scurried through the home. He poured her first cup of coffee down the drain before he brewed Lily a new cup. He made sure to put in less milk than he did the second time before he stirred in the sugar. He wondered if it was enough, but he did not want to put in too much. With the cup made, Jerome walked back to the home office with hesitant steps. He was certain she was going to find fault in his work again. While it was frustrating, he was also aroused by it and almost hoped that she would make him do it yet again. It was not to be, however, as Lily took a sip and said, "You got this one right." "Thank you, Miss Ghosn," Jerome replied. Lily nodded before she told Jerome to explain the spreadsheet he had left open on his machine. Jerome shook his head as he said, "You don't have to worry about that." "No. I want to know. I'm the boss for the day. I need to know these things." Jerome shrugged before he explained the spreadsheet to her. Lily made mental notes about what he said. Once he finished, Lily asked him go through what he normally did. "Why do you want to know?" Jerome inquired. "You want me to do your job, but you never shared enough to let me know exactly what it is that you do." Jerome nodded before he stood beside her desk telling her what he did while he answered her questions. It had been a long time since he had such a long, detailed conversation with a person other than his wife. They broke only for lunch, which Lily picked up, knowing that Jerome would not leave the grounds of his home despite their game. With her out of the home, Jerome scurried back into his office. He retrieved the pair of heels he kept locked in his desk and stepped into them. He moved about the home office in them until the time he conservatively estimated her return. After locking his heels back up, Jerome waited another 30 minutes for Lily to return. Each ten minutes that passed without her presence made Jerome rue his decision to take off his heels too early. Lily walked into the home office with the lunch. Jerome took the bags from her and put his on her desk and hers on his desk. Lily smiled as she sat behind his desk and told him to close the door behind him. Jerome nodded as he closed the door and heard her get on the phone with someone while he took a seat at his secretary's desk and began to eat by himself. The room was quiet, other than the sound of Lily's muffled voice through the door and walls. Jerome grew bored as he ate his meal in silence at the desk. He ate quickly, threw out the containers and cleaned the desktop before he knocked upon the door to his office. After Lily told him he could enter, Jerome walked into the room and asked, "Is there anything I can do for you this afternoon, Miss Ghosn?" "No," Lily answered with a grin. "Really, nothing?" Jerome replied, realizing that she was happy about the shoe being on the other foot as he was going to be forced into the state of boredom she found herself in everyday due to his refusal to give her any work to do. "Just do what the old secretary did. Freestyle, make something up to do," Lily rejoined. "Yes, Miss Ghosn," Jerome replied while he stepped out of his office. Jerome looked around the general office area. He walked over to the fireplace and began to clean away the ash at the bottom of the fireplace. He refilled the fireplace with new wood before he stepped back. A grin came to his face, as he felt his stockings pull on his legs while he did so. Jerome nodded as he decided to finally replace the wood burning fireplace with a gas conversion. Jerome walked out of the home office and made a few calls to find a contractor before a man agreed to come and provide an estimate. As Jerome returned into the home office, Lily inquired about where he had been. Jerome explained his decision and actions. Lily nodded as she said, "I think it would be nice to have a fire going in here to look at." Jerome nodded before Lily returned to her office. Lily went back to doing the work that Jerome described to her, while he went and reorganized the supplies he kept by the copier for the remainder of the day. "Well, that was fun," Lily loudly declared while she got up at the end of the workday. Jerome responded with an unseen nod before she walked out of his office and said, "Maybe we could do it again sometime." "I'd love that," Jerome said. "Good," Lily replied, knowing that he was telling her the truth. She said goodbye to him before she headed out the door of the home office. She exited his house and dialed Gloria as soon as she got into her car. "Hello." "Hi, Gloria." "Lily, how are you?" "Great, you." "Terrific. What's going on?" "I just wanted to let you know that I'm leaving your house..." "On a workday, shocking," Gloria teased. "It was an unusual workday." "Did my husband finally give you something to do?" "Yes, it was something!" "What?" Gloria asked, intrigued by Lily's unusual tone. "He made me do his work." "Strange, but alright. So what'd he do?" "My work," Lily said in a loud voice after a deliberate pause. Gloria started to laugh before she asked for an explanation. Lily smiled as she replied, "He said he wanted to be me for the day. He was as bored as I am or so he claims." "That's just a strange request. Why would it even cross his mind?" "I don't know. I can't be sure." "What are you not telling me?" Gloria pressed her friend. "He kind of seemed to enjoy it. He said he wants to do it again. I think he means it." "Like when, tomorrow?" "He didn't say." Gloria shook her head finding her husband's actions curious before she said, "Maybe, he's just having fun." "He was definitely having fun." "Well, he deserves it. Maybe he'll be in a better mood." "He's still been moody?" "Ever since the fall." "Yes, he's not as nice as he usually is. I don't know if he's still hurt, but he's moving around like normal," Lily noted. "Well, hopefully this gets him back on the right track," Gloria replied before they shared the details of the rest of their lives since they had last spoken a few days earlier. Lily's words preoccupied Gloria's mind while she finished her work at a charitable event. She went home and smelt the dinner that Jerome had made for himself, knowing that she was going to be out for the evening. Gloria walked through the home and found him on the den couch. She exchanged pleasantries with her husband before she inquired about what Lily told her. Jerome's eyes widened as he asked, "Why would she tell you that?" "She's my friend. She has to," Gloria replied to her blushing husband. Jerome shook his head and said, "It was nothing. I was just a little bored. I figured it would be a fun changeup." "Okay," Gloria replied to Jerome's relief, as she seemed to accept his answer before she went up to their bedroom to change into her at home attire. ----------------------------------------------------------------------- Lily and Jerome returned to work the next day. Jerome decided not to talk about what had happened and let it go. A few weeks passed without issue before the urge in Jerome became too hard to deny again. As a quiet Friday came, Jerome decided it was the perfect time to suggest a swap again. Lily agreed without hesitation before she settled in behind his desk again and ordered him to get her a cup of coffee. "Yes, Miss Ghosn," Jerome replied with a grin that accompanied the growing erection in his nylon pantyhose. Jerome made the cup of coffee in line with his prior experiences. Lily was satisfied with the cup he returned to her before she said, "I haven't cleaned the office this week, Jerome, why don't you get too it." "Yes, Miss Ghosn," Jerome replied. Jerome walked out of the office and retrieved the cleaning supplies. He returned to the office and began to dust the tabletops, lamps, ledges and paintings. Lily walked out of her office to witness the wealthiest man she ever knew cleaning at her behest. A bemused grin came upon her face while she watched Jerome lean up to dust the painting hung over the fireplace mantle. Her eyes darted down to his legs as she saw his pants legs pulling up his legs. Her mouth dropped once she noticed that what she had assumed were thin socks were certainly not what she assumed. "Holy shit," she muttered to herself, realizing that Jerome was wearing patterned pantyhose. Lily struggled to keep from snickering as she scurried into her office for the day and closed the large wood door that was decorated with an intricate pattern. She reached for her pocketbook and removed her cell phone to call Gloria. Surprised to see her friend call her in the middle of the day, Gloria answered the phone and inquired why her friend was calling. Lily had difficulty telling Gloria what she had seen before she forced the words out, "Jerome's wearing pantyhose." The three words stunned Gloria. She shook her head and asked, "Are you sure?" "One hundred percent. He's wearing diamond patterned, black, sheer pantyhose. I saw the exact same pair on a mannequin leg at Macy's last weekend." Gloria was silent before Lily asked if she was okay. Gloria shook her head before she responded, "What am I going to do?" "That's why I was calling? What do you want me to do?" "I have no idea." "What's his shoe size?" Lily inquired. Gloria was taken aback by the request. After a pause, she replied, "He's a size 8. Why do you want to know?" "I'm going to pick something up for him." Gloria shook her head before she asked, "Why?" "I need to see how far this goes." Gloria nodded to herself while she replied, "Do it and let me know." Lily agreed before she hung up the phone and stood back up. She opened the office door and called out, "Jerome." "Yes, Miss Ghosn," Jerome answered with eager docility. "I'm ordering from Mulino's. Is there anything you'd like?" Jerome grinned at the name of his favorite restaurant to order in from. He quickly gave Lily the order before she placed it and told him that she was going to pick it up. Jerome gave her the company credit card. Lily took it and told him to keep cleaning until he got back. Jerome accepted his order with a smile and watched as Lily left the office. She picked up speed as she moved through the home. After stepping out the front door, Lily made her way to her car. She began to laugh as she started down the long driveway of the estate that Jerome had purchased due to its remoteness from the neighboring homes. Lily pulled out of the driveway and steered towards the restaurant. As she drove down the main road to the restaurant, she veered off the road and into a small strip center. Lily then parked her car and walked into the shoe store. A salesgirl approached Lily while she looked up the conversion of men's to women's shoe sizes on her phone. Lily told the girl what she was looking before she walked towards the shoes that were displayed above boxes containing them in all different sizes. She went through the various designs of heels and wedges before she came upon a pair she felt would go well with his pantyhose. She took the four and half inch spiked heeled, black velvet pumps in her hands and looked over the colorful flowery embroidery from all angles. "This should fluster the queen," she said to herself with a laugh while she ran her finger over the flower over the vamp. Satisfied with it, she bent down and looked through the boxes before she pulled out one in the size she estimated for Jerome. Gloria opened the shoebox and looked over the shoe to make sure that there were no defects before she started towards the register. The cashier smiled at the design of the shoes and complimented Lily's taste as she rang her up. Lily thanked the girl before she said, "I hope you'll be happy with them." "I'm sure I will be," Lily replied with a grin. After paying for her boss's new shoes with the company credit card, she stopped at the restaurant and picked up their meals. She then hurried back to the office, eager to confront Jerome with the shoes. With the shoebox concealed in an oversized pocketbook from her trunk, Lily walked into the home office and gave Jerome a smile. She handed him the plastic bags containing their food and said, "Go set this up." "Yes, Miss Ghosn," Jerome replied, sounding almost out of breath. He took the bag from her and scurried towards the office where he had barely locked away his shoes in time after Lily pulled up in front of his home. With her food and drink on the desktop, Jerome brought his food over to the secretary's desk he had adopted for the day. "Why don't you join me in my office for lunch," Lily said as she walked over to him. "I don't want to intrude," Jerome replied, not drawing any attention to Lily's description of his office as her own. "You're not. That was an order. I was just trying to be polite about it," Lily retorted with a smirk. Jerome nodded before he took his food into the office. Jerome walked towards the one guest chair that his wife insisted he keep in his office for her. Jerome sat upon it and stared at Lily as she sat behind the desk and pulled herself under it. Jerome's desk had no overhang for a guest by his choice, since he wanted to discourage his wife from intruding into the time he wanted to spend en femme. The decision was forcing him to sit on the edge of the chair while he leaned over the desktop to eat. Lily noticed his evident discomfort, but she paid it no mind. As they ate and chat, Lily decided to breach the subject of Jerome's cross-dressing head on. She cleared her throat and asked, "So, Jerome, how long have you been wearing pantyhose?" Jerome dropped his plastic fork into his bowl of food and stared at Lily with a stunned expression. His cheeks quickly turned red as he lied, "I don't wear pantyhose." "Really?" "No." Lily gave Jerome a disbelieving look before he added, "I never worn them." "So, you're not wearing them right now?" "I don't know what you're talking about," Jerome lied again. "So, you're not wearing black pantyhose with a diamond pattern, right now?" Lily asked with a grin as she motioned with her eyes down to his legs. Jerome blushed again, humiliated at the fact that she had caught a glimpse of his pantyhose. Deciding to keep lying, Jerome said, "Oh, that. They're just long socks." "Really, why don't you roll up your pants and prove it." "I don't have to take this," Jerome said, remembering that he was the boss. "So, you want Gloria to know?" "Like she'll believe you..." Jerome countered. "She believed me when I told her you wanted to switch jobs with me...And without any hesitation, I might add." Lily's words stunned him. Jerome knew they were true before he said, "But this is different..." "Is it? Or will she think that a man who wants to play secretary, wants to look the part too?" Lily teased. Jerome's manhood swelled as he realized that he was caught, even as his stomach wrenched. He had long fantasized about this moment, however, it was far more embarrassing than the erotic discovery that he had hoped it would be. Lily grinned at his reddened face as she reached for her bag and pulled out a cream-colored shoebox. Jerome stared in silence at it before she pushed it across the desktop to him. "What's this?" "Those are the shoes I expect you to wear with your pantyhose." "Shoes?" Jerome said with growing discomfort while he clasped the box. "Oxfords do not go with pantyhose," Lily chided with a wag of her finger. 'Tell me about it,' Jerome thought as he removed the lid of the shoebox and stared at the flower-embroidered shoes with wide eyes. He loved the way they looked and wanted to see if they would be a good fit for him. It had been so long since he got a new pair. He could only have them delivered when Gloria went on vacation without him, which she had not found the time to do since her mother passed two years prior. Lily gave him an expectant look before she said, "What are you waiting for? Put them on." Jerome froze, prompting a yell from Lily, "Jerome, now!" Jerome's hands hurried to remove his shoes. He fiddled with the laces, feeling knots in his stomach as he undid each knot of the shoes. He was in disbelief that he was following through with her orders, showing her his pantyhose covered feet in the process. "I'm sure they won't fit," Jerome said in a low tone that conveyed his weakness. His heart skipped a beat as he slipped his feet into the patent leather trimmed pumps and found that they fit him. "Now, that looks right," Lily said as she stood up and peered down at the shoes. "How did you know my size?" Jerome asked, stunned by the development. "Educated guess," Lily answered to Jerome's satisfaction. "How long am I going to have to wear these?" Jerome asked. "Just for the rest of the day," Lily replied, making Jerome's manhood swell to its fullest as his toes pressed firmly into the padded insole of his shoes. Lily turned her attention away from Jerome for a moment before she took another bite of her food and said, "Eat up, your food is getting cold." "Yes, of course. Thank you," Jerome muttered with blushing cheeks before he started eating again. As the room became silent, Jerome could do nothing but sneak glances of the shoes on his feet. He loved the way they looked and wished that he could embrace wearing them the way he did when he was alone. "Now, you didn't answer my question, Jerome. When did you start wearing pantyhose?" Lily asked, puncturing the silence in the room. "I don't remember," Jerome replied, unsure of how to respond. "I find that hard to believe. I mean, little boys don't get dressed in pantyhose by their mothers. You had to do it on your own." "That seems right, I guess..." "Seems right or is right?" Lily asked, intrigued by Jerome's response. "It's right," Jerome admitted. "So, when did you do it?" "I stole a pair of my mother's when I was about 12 or 13." "Your mother's?" Lily replied, turning her nose to his claim. "I know. I didn't have a sister," Jerome replied with resignation and embarrassment of wearing the same intimates as his mother had. "I bet she wouldn't have been happy about sharing her panty drawer with you either." "My mother didn't know." "She didn't?" "Well, she didn't acknowledge it, but I think she did," Jerome admitted. "So, she passed you off to another woman without saying a word." "Are you talking about Gloria?" "Of course. You mother didn't let her know she was marrying a gay guy?" "I'm not gay," Jerome countered. "Look at your feet, Jerome." "That doesn't mean I'm gay. I'm only attracted to girls," Jerome grumbled. "But you want to look like one?" Jerome responded with a sullen nod to her question. "So, you're a lesbian?" Lily asked with a laugh. "I'm not a girl. I don't want to be a girl. I like being a guy. I just want to be able to dress like a girl." "Come on..." "No. You asked. That's it. That's my truth. I want to be a guy in a dress, not a girl in a dress." "Then, why aren't you wearing one?" "I don't think Gloria would like that," Jerome replied. "You're probably right," Lily responded between bites as she finished her meal. With their meals finished, Lily dismissed Jerome from the room and said, "That's enough chitchat. Get back to work, Missy." Jerome was momentarily taken aback by her words before he said, "Yes, Miss Ghosn." Lily grinned while Jerome got to his feet and walked out of the room and went back to cleaning. Jerome's manhood swelled as he heard his heels clicking on the floor just as they did when he was alone. Lily's presence added a new dimension that made him uneasy, but his arousal soon consumed him while he returned to cleaning the home office. His intent focus on his laborers made him miss the few photographs that Lily was covertly snapping of him while he tidied his home office in heels. After taking the last picture, Lily crept back behind the desk and forwarded the images to Jerome's wife. Gloria stared at the pictures in shock as they came upon her phone. While she believed her friend, the confirmation was disconcerting. There were was no denying that she was looking at pictures of her husband cleaning his home office with pantyhose covered ankles and high heels on his feet. Gloria thanked Lily for the images even as she struggled with how to process what she had seen. She took the long way home that night to think over how to respond. Once she got home, Jerome could sense that Gloria was more distant than usual. He suspected that Lily had shared yet another secret with this wife, but he did not want to admit what they had done for fear that there was another reason that Gloria was troubled. ----------------------------------------------------------------------- As the next afternoon came, Lily drove to a restaurant to meet Gloria for lunch. They greeted each other with kisses and hugs as they did every time they saw each other They walked into the restaurant and were seated. After giving their orders, Lily asked, "So, how are you handling things?" "I don't know. It shouldn't bother me." "Why?" "Did he look happy?" "He looked nervous," Lily replied with a smile. "Even after he got to working?" "Well, he certainly got more comfortable." "I know he was unhappy." "He was," Lily seconded. "I want him to be happy." "Well, he's happy being a secretary," Lily replied with a laugh. Gloria was struck by her words. She processed Lily's words before she asked, "Did he say that?" "Oh, he won't admit it," Lily replied as their salads were placed in front of them. "Well, what if we force him?" Gloria responded. "He won't let us," Lily replied. "There's got to be a way." "Let's tell him that I caught him forging documents," Lily joked. "Did you?" "Of course not!" "He's not going to believe that." "He won't know that. I might be able to convince him that he did it inadvertently. I could have snuck something into his papers the last few weeks." "That sounds like blackmail," Gloria replied with a growing smile. "Blackmail is such an ugly word. I much prefer Pink Mail. It sounds much prettier," Lily rejoined, knowing that they had reached an unspoken accord. ----------------------------------------------------------------------- As Lily walked into Jerome's home on Monday morning, she felt nervous. Gloria had helped her forge documents that made it appear that Jerome had signed his name to fraudulent documents that violated various Securities and Exchange Commission rules that his publicly traded company was required to comply with each year. Lily and Gloria knew that Jerome had disdain for the rules that constrained him despite the controlling share that he and his wife shared of the company he had founded. It was his wife that pushed him to take the company public. It grew the company larger than it ever could have been otherwise and made them even wealthier. The press from the initial public offering had done more than anything else to prompt his retreat from the world. He loved his privacy and the success of the public offering had ended any expectation of privacy he had as trade and financial papers stalked him at his office for quotes and interviews. Lily walked into the home office and put her bag down. She removed the documents from her bag and knocked on Jerome's door. "Good morning, Lily," Jerome said. "Don't give me that," Lily replied. "What?" "I know what you did!" "Did what?" "I saw it on Friday. I had to sleep on it before I got the guts to tell you what you had done." "Is this about the pantyhose?" Jerome inquired, feeling knots returning to his stomach. "If only that was the issue," Lily retorted with a shake of her head. "What's wrong?" "THIS," Lily said as she threw the documents down on his desktop. "What is this?" "Documents you prepared." "It looks like I signed them, but..." "And gave them to the SEC." "So, what?" "They're fraudulent." "How so?" Jerome's eyes widened as she pointed out the errors that she had no way of knowing were errors. He, however, knew that they were. He was sure that one of his underlings had deliberately defrauded the numbers and information reported to the SEC and sent it for his signature. He could not understand why he signed them. They were the type of things he was certain he would catch, but he did not. His increasing fears that his frustration about not being able to cross-dress had made the quality of his work decline were confirmed in an instant. "I can't believe you did this, Jerome!" "I didn't mean to," Jerome replied. "I'm taking this to the authorities." "No. Please don't," Jerome replied, knowing that he could never last in a prison cell, even though he was certain that his sentence would be short in a minimum security, white-collar prison. "What are you willing to give me?" "Whatever you want. I've got money," Jerome answered. His desperate tone made Lily struggle not to laugh before she said, "I don't want to do anything suspicious." "I can get it to you out of the country," Jerome added. "No. I like being right here, where I can watch you. Gloria was right. You need someone here with you." Jerome gave Lily a confused look before she said, "Gloria's my best friend. I can't hurt her. If I hurt you, I hurt her." "So, you'll..." "SILENCE! I can't let you hurt her either. I can't let you keep committing crimes. If you go to jail, all of her society and business friends will turn her away. Her life will be ruined just so you could make a couple of extra bucks. HOW COULD YOU DO THAT TO HER? I CAN'T BELIEVE IT. I really can't. I have to do this for her. I have to make sure you won't hurt her." "I won't. I didn't...at least, I didn't mean to..." "STOP! I'll keep my lips shut just as long you report everything you do to me." Jerome was stunned by her words as she continued, "From now on, the swap is permanent. I'm the boss, you're my secretary. Got it?" Jerome stared at her vacantly before she added, "Got it?" With tearing eyes and a racing heart, Jerome gave her a silent nod. "Now, your boss wants to know what you've got hidden behind that door." "I can't show you that," Jerome exclaimed out of desperation. "I'm the boss. You answer to me now," Lily countered. "Please," Jerome pleaded. "What else are you hiding? Is there stolen artwork, gems, what?" "It's nothing like that." "It's time to prove it," Lily replied as she pointed him towards the door. Jerome put his head down as he walked towards the door and pressed the numbers that Lily forced him to recite aloud. Lily's eyes widened as Jerome opened the door, stepped inside and turned the light on the closet containing his feminine wardrobe. Dumbstruck for a moment, Lily walked into the room and began to peruse what he had hanging up. She started to laugh as she said, "Well, you've certainly done a lot more than wear pantyhose." Jerome blushed before Lily reached for a skirt suit. She pulled it off the closet rod and handed it to Jerome. "What do you want me to do with this?" "I expect my secretary to wear skirts," Lily answered in a firm tone that turned Jerome on. Despite his increasing arousal, Jerome was terrified. While he had long fantasized about being forced to dress en femme, the reality of it was beyond unnerving. He took the clothing from her while she left him in the closet, closing the door behind her as she exited. Jerome hurried to disrobe before he stepped into a pair of black, cotton panties. Jerome's then hands reached for a matching bra. After slipping his arms through the straps, Jim clasped the front closures and stuffed the cups with his breast forms. As he straightened out his bra, Jerome turned back towards the dresser. He reached into it to retrieve a pair of nude pantyhose. Jerome then pulled himself on top of the dresser he had placed in the large storage closet. Jerome rolled the pantyhose down and placed his toes to the seams. Jim slowly worked them up his legs, enjoying the soft feeling on his legs. After pushing himself off the dresser, he brought the tights up to his waist before he reached for a top. Jerome slipped his arms through the sleeves of the red linen, collared blouse. Once he finished buttoning up the blouse, Jerome reached for a white skirt. He stepped into the above the knee, pencil skirt and brought it to his waist. After pulling up the side zipper of the skirt, Jerome placed on the matching, fitted jacket of the knit skirt suit. Jerome then reached for a pair of three inch heeled, white patent leather pumps with a crystal embellishment on the vamp. Once he situated his feet in the pointed toe shoes, he started out of the closet. Lily grinned as she Jerome emerged from the closet. She shook her head as she focused on his head. "Don't you have any makeup?" "It's hard to hide that," Jerome admitted. "Fine," Lily said as she walked towards him, grabbing her purse in the process. She took out a lipstick container. Jerome's eyes widened as the lipstick emerged from the container before Lily spread it across his lips. She smiled as she ordered, "Smack them." Jerome followed her command, feeling his member surge as he complied. She grinned at the effect of the bright red color on his lips before she said, "Now, do you have anything for your hair?" "I've got a wig, but..." "Put it on," Lily ordered, cutting Jerome's reply off. Jerome nodded as he walked back into the closet and retrieved the long, wavy haired blonde wig. He blushed as he pulled it over his head and straightened it out. Lily grinned at the effect the wig had on his overall appearance. She smiled as she said, "That's better, girl. I never would have taken for the blonde bimbo type, though." Jerome only nodded in reply. Lily smirked at his submissive inability to meet her gaze while he continued to nod. She stared intently at him as she ordered, "Go get me a cup of coffee." "Yes, Miss Ghosn," Jerome replied, feeling as if he was truly beneath her for the first time. He blushed as his heels clicked on the floor. His manhood swelled while he quickened his pace, unable to keep himself from becoming aroused. He cursed his arousal at his subjugation while he made Lily a cup of coffee. He then clasped the cup and carried it back into the home office. Lily grinned as she took the cup from the man before her who was clad in professional female attire. She took a sip and ordered him to stand beside her desk. Jerome complied as he answered question after question while she worked at his former desk. Jerome answered truthfully, afraid that a wrong answer would lead to Lily turning on him and imprisoning him. His knees wobbled at times. He was not used to standing in heels in one spot for long. He adjusted his legs as lingering fears made him uneasy with every glare Lily shot him. Lily's phone buzzed. Jerome's eyes and Lily's darted towards her phone that rested on her desktop. Lily reached for her phone and read the text. She grinned as she said, "Jerome, I need you to shred some documents." Jerome took the papers from her and started towards the shredder that was next to the copier. He walked towards it and began to feed the documents into the machine. "Hello, hello," a voice called out over the sound of the shredder, causing Jerome to freeze. He stared on the brink of tears while his wife walked into the room. She came to a stop as she fixed her eyes on his feminized state in person for the first time. Gloria was silent as she moved towards him in slow steps. She was amazed by how feminine Jerome looked in the skirt suit with a makeup and wig adorned head. While she expected to see him in a dress, she never expected him to look convincing. Remembering the role she was supposed to be playing, Gloria shook her head and asked, "Jerome, why are you dressed like that?" "I can explain." "I'd like to hear it!" "I was...I have a little problem...No..." "He's a con man," Lily interjected, walking out of her office. "What do you mean?" Gloria inquired before Lily produced the documents they had forged together. Gloria glared at her husband and confronted his fraudulent actions. Jerome denied knowingly doing it. She shook her head, noting her disbelief before she said, "This still doesn?t explain why you're dressed like this." "He's been dressing like this for years," Lily replied for Jerome, giving him no out. "How do you know that?" "Follow me," Lily said as she led Gloria to the closet. She punched in the code that Jerome had read loud. Gloria's jaw drop as she saw the closet full of woman's clothing that Jerome had long told her was for company secrets only. She was angered by his lying far more than the female clothing. "Who knew, we could have been sharing a wardrobe," Gloria spat at her noticeably taller and heavier husband. Jerome blushed at her words before Lily replied, "At least he won't be lying anymore." "No. He won't, but this still doesn't explain why he's dressed like this now." "He's dressed like this because he's my secretary," Lily answered. "What?" Gloria replied with feigned shock. "He agreed to permanently swap roles. He's still the titular boss, but I'm the one doing that work and he's my assistant." "Why would you do that?" Gloria inquired. "I'm doing it to protect you. Do you know how much this could damage the company if it gets out?" Gloria paused before she nodded and glared at her husband. She turned her gaze back at her best friend and thanked her to Jerome's horror. Gloria then added, "I've got an event this afternoon, but starting tomorrow, I'm coming to work with you, Jerome. I'm going to make sure that you're doing the right thing." Jerome nodded, feeling ready to cry and explode with anger at the underling that set him up. ----------------------------------------------------------------------- As the evening came, Jerome sat in his den in silence. His hands were clutched in front of his stomach. He felt nauseas while he rocked back and forth, waiting for the inevitable. Thoughts about his day being ordered about by Lily en femme crept into his mind as he felt the aches in his feet, ankle and back from his day in heels. Despite the painful reminders, he could not focus on the memories for long, since his wife's response was his sole concern. Gloria pulled up in front of the home. She stared at the front door she had passed through thousands of times. She had never been nervous entering it before. Gloria's hands trembled as she got out of the car. She took hold of a bag from her trunk and started for the door. Jerome's head perked up at the sound of the front door opening. He got to his feet to approach his wife. Despite his determination to do so, Jerome did not move an inch. He felt a disconnect between what his mind told him he must do and what he was willing to do. Gloria called out his name. After a pause, Jerome replied, "I'm in the den." The sound of Gloria's heels clicking on the floor grew closer as Jerome's heart raced. He took a few deep breaths, fearful of what awaited him. Gloria entered the room and came to a stop as she saw him. She shook her head and inquired, "Why did you change?" "I didn't think you'd want to see me like that," Jerome replied with his eyes squarely trained at the socks on his feet. Gloria shook her head as she said, "Oh, no. I can't see you like this." Jerome's eyes rose up to her, unsure of what she meant. Fearing that she was throwing him out, Jerome said, "Gloria, I'm so sorry, I..." "Save it, little girl." Jerome turned his head and blushed before Gloria continued, "If you want to be a girl, you're going to be my girl." Jerome's eyes rose to meet Gloria's. Gloria smirked at his confused response. She then added, "If you're going to be Lily's secretary, you're going to be my wife." "How can I be that?" "Well, lesbians can marry now." "But you're not a lesbian." "Maybe I'm a lesbian for you," Gloria retorted before adding, "But there's only one way to find out." "How?" "Follow me," Gloria ordered. Jerome followed behind Gloria into the kitchen. His eyes focused on the brown paper bag on the countertop. Gloria was silent as she removed the hair dye box that contained matching highlights. Jerome's gave the box a confused look before Gloria said, "I'm not having an old mare for a wife." Jerome was aghast as his hands reached for his short, salt and pepper hair. Jerome stammered, "I think it makes me look distinguished." "If you were a man, yes, but, clearly, you're not. Are you?" Jerome blushed, feeling none of his usual confidence or aggressiveness. He hung his head while Gloria removed a pair of glasses. "What are those for?" "They're yours." "I've got contacts. I don't need glasses," Jerome countered in a meek tone. "No. You're wearing them," Gloria retorted, dismissing his argument offhand. "For who?" "Me and Lily, we're the only two who could pick you out of lineup, other than some of our family members." "But..." "Don't try to fight it, Jerome, or I'll tell Lily to go right to the authorities," Gloria replied, cutting him off. Jerome fell silent in the face of the threat. Gloria nodded at his obedient silence before she ordered him to make dinner while she set up. Jerome asked what she wanted. Gloria responded that she wanted something that was quick and easy. With the order in mind, Jerome made a quick meal based on the food that they had in the house. He scurried around the kitchen before he put the meal on the dinning room table for his wife. Gloria sat down at the table and ordered him to serve her. Once he finished, she told Jerome to eat beside her. He paused only to serve her at her request. Other than Gloria's occasional orders, they ate in silence before they returned to the kitchen. Gloria sat Jerome down and ran her fingers through his short hair. She smiled to herself as she said, "Fortunately, this won't take long." Jerome nodded as his wife put on plastic gloves. She wrapped an old, stained towel around his neck and began to apply the dye to his hair. Jerome hated the smells that surrounded him. The scent of the dye was strong. It was the reason that he had banned his wife from dying her hair on her own years earlier. Jerome knew that the ban was certainly gone, as was every other rule he had imposed on his wife. He was displaced from his position as the dominant partner in their relationship the moment she saw him in a skirt and heels. The fact excited him, even as the loss of control for the first time terrified him. Once Lily finished applying the dye, she told him to clean up the kitchen. Jerome nodded as he reached for the plates and pots and began to clean them up as the minutes on the timer ticked off. Jerome filled the dishwasher while Gloria began to mix the highlighting formula until it was smooth and creamy looking. The sound of the timer beeping brought Gloria to her feet. She ordered Jerome over to the sink before she rinsed out his hair with warm water until the water began to run clear. Gloria picked his head up and squeezed out the excess water from his hair before she applied after color-conditioner to his hair. Jerome's member enlarged as he felt his wife's hands working the conditioner through his hair and against his scalp. After letting the conditioner sit on his head for two minutes, she rinsed his hair with cool water. "Can you warm that up?" Jerome asked. "Nope," Gloria replied, careful to spray the water so that it would run down by his mouth to discourage further complaints. Once she finished with him in the sink, she began to apply the highlighting mixture to the strands along the front of Jerome's hairline. She saturated each strand she touched, highlighting it along its entire length from bottom to the top. She applied it the lightest at its roots. She alternated from side to side to ensure that the highlights she applied to his short hair were even. On she finished, Gloria put down the highlighting materials and disposed of them in a bag. She made Jerome take the trash bag containing the supplies out of the home. Jerome followed her order without uttering a complaint. Jerome was happy for the great distance between his home and his neighbors since he was certain that no one could see his damp, colored hair. After returning into the house, Gloria washed his hair thoroughly. His short hair quickly dried beneath the intense heat of her hairdryer. Putting down the hairdryer, Gloria nodded at Jerome before she ordered, "Go get an outfit from your girly closet." "What do you want me to wear?" "Whatever you think is the prettiest outfit you own," Gloria answered. Jerome nodded as he walked into the home office. He went to the back of the room and punched in the key code. After opening the door, he stepped into the room. Jerome walked into the closet and looked over the suits and dresses he had collected over the years. While Jerome wanted to put on something conservative, he knew that his wife had seen his collection. If he picked something subdued, she would likely pick out an outfit for him. Deciding not to risk her wrath, Jerome reached for a dress. Jerome took the silk, v-neck dress in his hands and gazed at it. He had loved the floral print dress from the moment he saw it. "That's a pretty choice," Gloria said from over his shoulder, causing Jerome to jump. She grinned at his surprised reaction to her presence. Jerome nodded in reply to her claim as he thanked her, despite his racing heart. Jerome hung the dress back up before he reached for his underwear drawer to build the rest of the outfit that he was going to pair with the dress. Jerome disrobed and pulled a pair of baby blue, satin panties up to his waist. He situated them snuggly against his waist before he tucked his manhood. Gloria smirked at the smooth front he had created in the process of tucking himself. She walked over to her husband and rubbed where his manhood normally rested. His wife's grin made Jerome uneasy. She did not say a word and he could not find the will to say anything. Once her hand pulled away from the smoothness it was caressing, Jerome reached for a baby blue bra and placed it on as well. The cups were soon after stuffed with his breast forms. Jerome turned beet red as his wife ogled his faux breasts. She was amazed by the details of the forms and their effect on his figure. With his bra and panties on, Jerome took hold of his black opaque tights and went over to a chair with Gloria in tow. Jerome rolled the tights down before he brought them up his body. He pulled them up and snapped the waistband over his panties and tucked member. Jerome then grabbed his a-line silhouetted dress. He pulled it on over his head and placed his arms through the short butterfly sleeves. He brought it down over his body and twisted his legs, causing his knees to brush against the layered ruffle hem. Gloria stepped back and examined him. Jerome smiled at her impressed look and asked, "How do I look?" "Not bad," was all Gloria offered. "There's a mirror on the back of the door." "You're not looking in it," Gloria retorted as she put her back to the open door. Jerome nodded before she said, "Put on your shoes and let's go." Jerome turned to look at the shoes that were resting beneath his clothing. He reached for a pair of 2 and half-inch block heeled, patent leather, almond toe pumps with an ankle strap, prompting Gloria to clear her throat. His head jerking to face her, Jerome saw the shake of his wife's head at his choice. He said he was sorry before he reached for a higher heeled pair of pumps. Gloria told him the shoes were acceptable as he balanced himself against the wall while he put one black, three inch heeled, rounded toe pump with a twisted trim on after the other. Gloria smirked at his obvious practice with putting heels on before she ordered him into the bathroom. The sound of two sets of clicking heels on the floor seemed strange to Gloria and Jerome. It made Jerome's manhood swell, knowing that he was the source of one set of the sounds. Gloria's eyes focused on the feminine sway of Jerome's hips with each high-heeled step. She struggled to keep from laughing at him. Jerome moved through the house and reached for the bathroom door. Gloria ordered him to stop before he stepped inside. She reached up and placed her fingers over his eyes and led him into the room. Gloria sat him down the toilet seat and ordered her husband to stay still. Jerome was motionless while Gloria went to remove his contacts before she put them on the counter. His vision was instantly blurred as he looked around the room. Gloria appeared to be a blur as she reached for her makeup bag. She clasped his head and began to add makeup to his face. Jerome tried to stay calm while his wife applied his makeup before she put some makeup in a purse. Once his makeup was finished, Gloria reached for a bottle of hair gel and squeezed some into her palm. She rubbed it between her hands before he ran it through his hair. Jerome's head jerked as she styled his close-cropped hair with the gel. Once Gloria finished, she washed her hands and said, "I'm going to have you grow your hair out." "How long?" Jerome asked, a bit concerned that she would make him match her shoulder length hair. "Not too long. Just long enough for a cute bob or something. You're one of the older girls whose head is just better suited for short hair," Gloria explained in response. Jerome grimaced as he thought, 'I am?' Drying her hands, Gloria caught her husband's expression. She grinned to herself before she said, "Stand up." Jerome complied as he got to his heeled feet. He snuck a glance at the feminized silhouette he saw in the mirror. The blurry image did not look like him, even though he was certain it was. Gloria reached into the drawer of the vanity and pulled out a package. Jerome's eyes tried to focus on it as he heard the package rip open. "What's that for?" "Added protection to keep your little dick from making an appearance." 'It's not little,' Jerome thought, but decided to keep to himself. His momentary distress over the comment was displaced once he realized what the package contained. "I don?t want to wear that," Jerome complained as his wife held a maxi pad before his eyes. "Well, too bad, girly. You're on your first period until further notice." Jerome's jaw dropped as he felt his wife pulled up the skirt of his dress. He blushed at the loss of control of his own body. His eyes closed at the sensation of Gloria's yanking down on his panties and tights. Jerome blushed as he shoved the maxi pad in place before she pressed up the sticky wings to his body help hold it in place. She soon covered the pad with his panties and tights. "How does that feel?" She asked. "Like I'm wearing a diaper," Jerome whined. "You'll get used to it. All girls do," Gloria replied with a wink that he could barely make out. "Hold on a second," Gloria then said before she left the room. Jerome pulled down the skirt of his dress as he waited for her return. Gloria reentered the room carrying a pair of glasses. She told him to lean down as she placed the glasses upon his head. Jerome felt relieved to be able to see clearly before he caugh

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Bianca sat in bed, absentmindedly scrolling through her social media feeds on her phone, whittling away the hours of the early morning. She didn’t have any plans for today, and tried to find some entertainment in the postings of others. One of her friends, Amy, posted a picture of herself in a skimpy swimsuit, captioned “missing the summer sun.” Her cleavage drew Bianca’s attention and she began to imagine those huge tits exposed to the warm, summer air, glistening with sweat. Her girl cock...

3 years ago
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Naughty Secretary

I walked into the office again. 'Holy shit, is she just putting herself on display? She has that big crack on there, so is she just pretending that I won't notice? Is she plotting for a raise or what?' I thought as I stopped in front of her desk. "Brooke?" "Yes, Mr. Green?" she asked, failing to look at me. I clenched my fists and got closer to her. "Would you mind covering your cleavage? This is a law firm and I want our clients and potential clients to think we are serious and respectful....

Office Sex
3 years ago
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The New Secretary

The New Secretary By Anonymous Writer I had been looking for work in the want ads and noticed there weren't many choices. Most of the jobs were menial labor or fast food types and didn't pay much. But I did find a job opening listed at a local law office. I circled the ad then drove down to apply. I entered the small out of the way building and noticed a stack of papers and books on a couple desks in the main office. After asking if anyone was in I heard a...

2 years ago
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Nelson Enterprises VP of Sales becomes a Secretary

Nelson Enterprises - VP of Sales becomes a Secretary The VP of Sales - Dan Watkins - sexually harassed one of his talented sales ladies - Kelly Weir - to the point she quit and then he used his influence to destroy her career. He will now be inheriting that body and the remains of that career and must learn to interact with his 2 ex- wives from a new perspective - as their maid. Summary to date: Bill: Bill Nelson was a famous billionaire inventor and playboy but now finds...

4 years ago
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My sexy secretary

My name is John Lampert. I've been with someone for like 4 years straight now. From one relationship to the next. You could say I'm dependent on relationships. I don't know why, but I've been that way since I was 26 and I'm 34 now. But at the time I was single. I'm 6 feet tall and have black hair and brown eyes. Since I really didn't have anyone to go home to, I worked late a lot. I worked in an office building as an executive. I have a secretary that I think might have a thing for me named...

Straight Sex
2 years ago
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Mistress Dyvias Secretary

Disclaimer: This story is my intellectual property, and should be treated as such, do not plagiarize, or post without permission. If it is not legal to view writings that are sexually explicit and have themes of bondage, feminization and other deviant sexual experiences: don't read this. Don't read it, if it is not legal to do so where you live. Going any further is of your own free will, and responsibility is solely on yourself. Mistress Dyvia presents: Mistress Dyvia's...

4 years ago
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The Perfect Secretary

The Perfect Secretary By Cherysse St. Claire "Cissy, would you bring in the projected revenues on the l'Audace line, please?" "In a minute, Ms. Fontaine. They're coming off the Laserjet right now." I reached over and withdrew the reports from the output stacker. The stark, white paper was a contrast to my long, slender fingers with their ultra-long, crimson nails. I patted an errant lock of my full, fluffy, golden-blonde mane back in place, checked my make-up in the desk-drawer...

4 years ago
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The secretary

She had spent too long waiting for a long promised fuck but tonight was the night. Even though she was in a relationship, for her the best sex was with others – the lustful dark fucking that she would only dare to do with others. He had been teasing her for the past year and she had finally told him to fuck her or fuck off. She was going to a conference where he would be and they had arranged to accidentally have adjoining rooms. It was the best cover for both of them. The worst part was...

4 years ago
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The secretary

She had spent too long waiting for a long promised fuck but tonight was the night. Even though she was in a relationship, for her the best sex was with others - the lustful dark fucking that she would only dare to do with others. He had been teasing her for the past year and she had finally told him to fuck her or fuck off. She was going to a conference where he would be and they had arranged to accidentally have adjoining rooms. It was the best cover for both of them. The worst part was...

2 years ago
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Watching my Father fuck his young Secretary

As Deborah bends over at the filing cabinet, John glances up from his desk and admires the view. The coffee-brown, wrap-around dress she’s wearing today highlights her stunning, statuesque figure, her long shapely legs, womanly hips and well-proportioned behind. Its late and there’s no one left in the building and John’s son is not due from the train station for at least another hour… He gets up and wanders over to stand behind his voluptuous secretary. As she rises back up from the filing...

4 years ago
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My New Secretary

One thing I want to do is to have my own business. A few months ago Ifinally decided to get started. It is a small distribution business. Iam mainly the middleman arranging products to be shipped all over thecountry. I don't have much of an overhead. So I don't need aninventory, just an office where I can conduct my business; a place tohang my hat so to speak.At first I worked everything myself spending most of my day on thephone. I needed a client base. As the amount of my customers grows,...

2 years ago
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Fun With Secretary

Hi friends, this is Chaitanya. This is a true story which happened in my office with me. I was looking for another secretary who can take care of my extra work in office after my earlier secretary left for Dubai after her marriage. I was searching for a good replacement for my old secretary who can handle all the work as efficiently as the earlier one. My business has also expanded more and I had to travel to many places to develop more clients. I was in need of a Secretary who does all my...

2 years ago
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Sexy Secretary

Sexy Secretary Intro My penname comes from a character I used to play in LockedInLace.com interactive fiction. One of the stories was based on the enigmatic M&R Corporation and I loved the idea of hapless males being transformed by a faceless corporation. I also loved the idea that the victims of M&R Corporation were forced to choose (or were allocated one by their "sponsor') from one of four feminine roles: schoolgirl, secretary, maid or sex-slave. I plan to write a...

2 years ago
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The New Secretary

The day hasn’t even begun and already I feel exhausted, drained of any energy I had to muster before I came into work. I’ve already made ten phone calls and replied to at least fifteen emails and it’s not even nine o’clock. I wish I could get out of here; start over somewhere new. Then, a year later, return. Because this city will always be my home, no matter what, and despite everything bad that has happened in the last few months. I should be happy that it’s Friday, at least. Yet I find...

Straight Sex
2 years ago
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Lady Boss and Secretary

John T. Larmon is a business executive for a famous exporting company in UK has been working hard for the maximum business potential for his company. Recently while he was on a business trip for a few days he had what was a rather unexpected but delightful experience. John was staying in one of the new suite hotels and was traveling alone planning on spending his time at company meetings and watching TV in his room. He went down to the lobby to get a drink as the hotel offered free cocktails...

3 years ago
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Super Secretary

Super Secretary By Jena Corso Edited By Angela Myers Part 1 "This game is going to be awesome!" Larry told his co-workers as they were grabbing some morning coffee in the office beak room. "Damn, I know," said Kenny. "I wish it was starting now. I'm feeling good about the Giants!" "You guys have no chance," Alan piped up. "Did you forget the Patriots were undefeated this year?" "Dude, the Giants played them well in the last game," said Larry. "They've definitely got a...

3 years ago
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Editing Reailty Book 2 Chapter 8Creating a New Secretary

Book Two: Sultry Fantasies Unleashed Chapter Eight: Creating a New Secretary By mypenname3000 Copyright 2019 Note: Thanks to WRC 264 for beta reading this. Steve Davies I shoved my teaching materials into my satchel while admiring the naked girls in my classroom. Two weeks had passed since I'd edited my classroom to have every girl strip naked. I had a lot of fun. I'd enjoyed all my female students, savoring their delicious snatches quivering about my cock. My students were learning...

3 years ago
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Denise My Hot Secretary

I've always had these wild sexual fantasies about my secretary, Denise. She is quite lovely, a sweet young girl about twenty-four or twenty-five years old, with a cute little girl look that I find so sexy!She is about five foot four inches I guess when in her stocking feet, but since she usually wears heels, she comes up to just below my own six-foot stature. She has a very nice figure too, not too skinny (I hate those skinny-as-a-rail types that look like they are afraid of food!), but not too...

Oral Sex
4 years ago
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Ballsy Secretary

Shemale - cum-eating – dominant – submissive – big cock – secretary – bossA few more good strokes and I'd be like a fire hydrant. My breathing was ragged; my fist pumped up and down the long neck of my cock nearly as fast as my heart beat in my chest. I love this part. That moment where your knees go weak and you finally give in. Your eyes clench shut and the pressure from your balls explodes up your shaft until your tip blasts that first strand of cum and sweet relief finally takes you over.I...

4 years ago
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Male Secretary

Yes that first date is correct, way back then I was day-dreaming in a junior-year business ethics class and this story came to me. I came across it recently and decided to save it by re-keying it and posting it. (It was originally composed on an Apple II+ and printed out on an Epson RX-80 dot matrix printer! High technology!) This story is purely fictional and meant for adult audiences only! If you are not an adult, please stop reading and dispose of this file. You have been...

2 years ago
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Stuarts Secretary

STUART?S SECRETARY STUART?S SECRETARY The way that model has his cock whipped reminds me of the day Uncle Pietro caught me with the Frederick?s of Hollywood catalogue that I?d stolen from the neighbor?s porch?Uncle Piet and Uncle John had condemned me for my pornographic interests..Uncle Piet using his sign language to declaim Mathew Chapter Five-?"You have heard that the law of Moses says, 'Do not commit adultery.' 28 But I say, anyone who even looks at a woman with lust in his eye...

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...

3 years ago
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Banging Anna My Hot Secretary

I married the girl of my dreams.  We met in college and were together for all four years.  I knew the day we met, we’d be together forever.  She was like the female version of myself.  We took our time getting to know one another.  The four years of college went fast and after graduation I proposed to Sara.  I didn’t want to lose her.I went into the family business and Sara found work in her field.  We lived together in a condo that we rented together.  After about a year, we married and...

Office Sex
3 years ago
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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
4 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...

2 years 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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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...

2 years 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...

3 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...

2 years 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...

4 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...

4 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
2 years 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
2 years 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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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...

4 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...

2 years ago
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Antheas baby 1

“What’s wrong? What’s wrong?”Anthea looked up at her mum as she sat down at the dining table. “Nothing is wrong,” Anthea responded watching as her mum hurriedly dried her hands with a tea towel.“Is the baby okay? Are you okay? Is Jack okay?” she asked as her husband came into the room and pulled up a seat at the table.“We’re all fine Mum,” she responded exasperated with her mum’s anxiety. “I have something to tell you.”“Sit down Helen,” her dad snapped. “Give the lass a chance to speak.”Anthea...

3 years ago
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Another wild encounter with my sexy secretary

That morning I had an early appointment to attend. I had left home without even a good breakfast; so I stopped for some coffee. As I was walking out, my sexy secretary Dawn pulled into the parking lot. She parked in a corner and I approached to greet her. She smiled at me and said it was cold outside; so she invited me to get into her car.Once inside Dawn put her hand between my legs and began squeezing my cock. She said she had gone there for a coffee; but she was feeling my cock would be even...

2 years 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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Uther

Uther By Ellie Dauber (c) 2006 Introduction According to the legends of King Arthur, Merlin changed Uther Pendragon into a double for Duke Gorlois, so he could spend the night with Ygraine, the Duke's wife. Ygraine and Gorlois had three daughters: Elaine, Morgause, and Morgan le Faye. During their time together, Ygraine became pregnant with the child who was to become King Arthur. Uther's men killed Gorlois that same night. This is my TG (of course) version of what...

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...

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