Imperial Dillema - Cover

Imperial Dillema

Copyright© 2025 by Ogreface

Chapter 10: On the Job Training

The ducal palace was laid out in a hollow square with the hollow center containing a private garden. The front section of the building housed the dukes as well as the viscount’s offices and also housed the public offices supporting the duke in ruling the system. The two side wings contained the private residences of the duke and the viscount. The rear part contained the servant quarters.

The main entrance of the palace consisted of a huge lobby full of paintings of past dukes and viscounts. Being a favorite tourist destination, the was also half full of tourists during the festival seasons. When ever the palace was open to the public, a marine platoon was doing ceremonial guard duty inside the circular chamber with its lofty ceiling. At the rear of the reception hall, in line with the huge main entrance doorways was an alcove laid out like a fancy reception area. That was the public reception desk for the duke’s formal office, a large and well decorated office used only for formal receptions.

Behind the duke’s formal office and on either side of the center line of the building running from the main entrance through the duke’s formal office, were two identical offices. Both were slightly smaller than the formal office the duke, with one being the private office of the duke and the other being the Viscount’s private office. Both offices had windows facing onto the secluded and private garden.

Sylvia led Jason along the internal corridor past the private reception area of the duke to another private reception area next to it. That reception area was empty. Sam quickly looked around the outer office as Ron entered the inner office. By the time Sylvia led Jason into the inner office, Sam was again in front of them.

The viscount’s office was neat and airy. The huge windows facing the garden was closed but the curtains were all open. The layout was similar to that of the duke’s private office, complete with a comfortable seating area in front of the huge bare desk. As Jason stood in the middle of the office looking at the nature paintings covering the walls, Ron came out of a hidden doorway behind the desk. He nodded to Jason and left, back into the outer office. Sam also glanced into the hidden doorway before she left, after giving Jason a naughty smirk. Sylvia was sitting behind the desk fiddling with the drawers so Jason wandered over to see what was behind the hidden doorway.

Jason was surprised to find a small suite attached to the office. The suite had a full bathroom and what might have been labeled as a dressing room. There were shelves and racks for hanging clothes but also a large bed. The shelves and racks in the room were bare but there were clean towels in the bathroom.

“Believe it or not but this place is specifically built so the Viscount can get to know any of his visitors more intimately” Sylvia said as she walked into the suite behind Jason. “The duke’s office has a similar suite. Richard used to keep a few spare sets of formal and casual suits here, not that he ever invited a lady friend, or even a secretary in here.”

“How would you know?” Jason asked as he gave her a smirk.

“In my young days I was good friends with his secretary.” Sylvia said. “Over time we started sharing a lot of secrets, including if any females were invited into the main office by the viscount. He never did. His secretary was also responsible for keeping the bathroom stocked. There is a list of required items, like feminine hygiene supplies and such. She never found any evidence that Richard even bothered to use the bed.”

“What happened to the secretary?” Jason asked.

“She decided to retire when Richard had his accident” Sylvia said. “I suspect she had a secret crush on him for decades except he never touched her.”

“Would she have told you if he did?” Jason asked. Sylvia gave him a smirk.

“Oh yes” she said. “We always compared notes, not that there was much to compare. I always ended up listening to her telling me about the marine officers she ended up seducing in here when the viscount was out of town.”

Something about how Lady Sylvia was moving and looking at Jason was causing him some mild discomfort. In the past, before he ran off, he seldom saw her and when he did, she was usually dressed fairly formally. He could distinctly remember always seeing her in high heels and wearing stockings and long sleeve tops. Since he never had breakfast in the informal breakfast lounge in the past, he had no idea what she wore during breakfast in the past. Now she was wearing a light sleeveless summer dress which ended halfway between her knees and her hips, much shorter than anything he saw her in before. She was also not wearing stockings and was wearing flat open sandals. She also kept moving in circles around him while eyeing him as if she was a tigress and he was a tasty morsel.

“I have never cheated on Richard” she said in a low voice as she ended up standing right in front of Jason with her hands flat on his chest. “I was a virgin when he married me. I can count on my fingers the number of times we have been intimate, only three of which resulted in me getting pregnant.” Then she removed her hands from his chest and slowly unbuttoned the top button of her dress. Jason glanced down between them and noticed the buttons went all the way to the bottom of the dress. He suddenly wondered if she would scream or just move away if he was to go down on his knees and start unbuttoning her dress from the bottom upwards.

“You will have to teach me what the duties of a guardian is” Jason said softly as he watched his hands move on their own to land on her hips. He realized he could end up in deep trouble if he was reading her attempt at seduction all wrong. He was actually planning on making as if he was pushing her away if he noticed any negative indication on her face from him touching her.

“Teaching you to be a proper guardian to me will be my pleasure” she whispered as she untied the next button. The view of her milky-white skin that got exposed suddenly helped Jason in getting very stiff.

“Those buttons, they go all the way to the bottom of your dress” Jason said as he looked Sylvia in the eyes. She had a slight smile on her face as she looked back into his eyes.

“Yes, so?” she whispered.

“Maybe you need some help with them” Jason said as he stood slightly back and then went down on one knee in front of her, his face now level with her hips. She dropped her hands to her sides as she looked down at Jason, that teasing smirk still on her face as she moved her one foot slightly to the side. Jason reached for the bottom button and slowly untied it. Sylvia’s only reaction was to move the other foot a few inched to the outside as well.

It was like unwrapping a long-awaited gift. As Jason unbuttoned more buttons he got to see more of her thighs. They were smooth and slender. She stayed standing in one spot but kept moving her legs wider apart, which gave him a better view of her inner thighs as they tapered up towards her groin. She seemed to be breathing harder with each button he undid as she looked down at him with huge eyes.

Jason was not sure what to expect when he untied the button in front of his face. He was shaking from excitement and anticipation. He has seen Roxy in the nude a few times when both of them were preteens and he saw both Roxy and Chloe nude in the shower that morning. As far as female underwear was concerned, his experience was nearly non-existent. Even during his time living and working close to Carmen and Sherry he never saw any of them in regular female underwear. He did see them in marine underwear, which basically consisted of the same boxer underpants and T-shirts the men wore.

At first nothing more was visible but then he moved on to the next button and suddenly Sylvia’s dress opened further, exposing her panties. They were tight-fitting white bikini panties; the sexiest sight Jason had ever seen. He totally forgot to continue untying buttons as he stared at the view in front of him.

“You can take them off if you want” Sylvia said softly as she suddenly started untying more buttons from the top again. Jason was definitely planning on removing those panties but first he wanted to admire the entire package. He stood and continued with the buttons, causing Sylvia to stop what she was doing.

When the final button was undone, Jason just stood there looking at her. She was wearing a bra as well. He had seen those in the laundry room of Sand Harbor when he was a kid as well as the laundry room of the marine base when he ended up doing his laundry along with Carmen and Sherry but this bra was different. It was nearly see-through and frilly. Sylvia’s breasts were relatively small and very sexy. Her nipples were tight little buttons making little bumps in the material of the bra.

Slowly Jason removed the dress from Sylvia’s shoulders, letting it drop on the thick carpet. Then he slid his hands from her shoulders down her bare arms until he got level with her breasts when he slipped his hands between her arms and her torso, reaching for where he suspected the clasp was. Sylvia leaned slightly forward as she placed her arms on Jason’s chest as he hunted for the bra clasp. After a bit of fumbling, Sylvia giggled as she reached behind her and quickly untied the clasp. Suddenly the bra dropped away leaving her breasts bare. Their shape fascinated Jason so much that he started exploring them, gently stroking over them. Sylvia inhaled sharply as his palms stroked over her pebble-sized nipples.

Jason was in heaven but he knew there was much more to explore so he moved down to her hips, hooking his fingers into the elastic of her panties. During all this time Sylvia never took her eyes off Jason’s face. As he slowly pushed her panties down her legs, she just stood there looking at him.

Jason again went down on his knees as he pushed Sylvia’s panties down to the carpet. She stepped out of them as she steadied herself with her hands on his shoulders. Suddenly he could smell her. She stood so close to him that he only needed to lean forward slightly to be able to kiss her stomach. He could not see much of her sex through the dense brown patch of hair covering her groin. He knew his real objective lie there, behind that patch of hair but the idea of kissing her stomach intrigued him so he did just that as his hands found their own way behind Sylvia and onto her butt. Sylvia groaned softly as she pushed her hips against Jason’s chest as her hands curled around his head pulling him tighter against her. Her skin felt like silk against his lips.

“You are still stiff!” Sylvia exclaimed as her hand wrapped around Jason’s slimy erection. She had just rolled off of him and was cuddling up against him after having her third orgasm.

Jason could not imagine anything feeling more exciting and fantastic than making love to a woman. Granted, Sylvia was old enough to be his mother, was actually the same age as Lady Olivia, and she was the first woman he had ever touched. At one point, Jason was getting a bit concerned, when Sylvia started crying the second time that she went into what looked like mild convulsions. She had assured him that she was having her second orgasm at the time and could not believe how nice it felt.

Her first orgasm was a total surprise to both of them. Jason was on his knees in front of her and decided to explore the treasure behind that bunch of hair. It was not particularly exciting to have to work his way through the hair but when he finally got to his real objective he didn’t think, he just dove in with his mouth onto that enticing slit, which was already quite wet. Sylvia collapsed half on top of Jason a few seconds after he licked her vagina. After that she quickly relocated both of them onto the bed where she helped him to get naked and on top of her. Her second orgasm occurred just as he erupted deep inside her, seconds after penetrating her fort. That was when she started crying softly. It didn’t take long before she pushed him onto his back and got on top of him, impaling herself on him. This time both of them took a bit longer, her vagina was so wet and full of his stuff that it didn’t feel as nice and exciting as the first time. That didn’t stop her from having her third orgasm before he was near to his. Watching her having her third orgasm while riding him excited him so much that he came as well, after which she collapsed on top of him.

“Let’s go clean up a bit before we make a total mess of this bed” Sylvia said as she jumped up. She giggled like a young girl as she ran for the bathroom with her hand covering her groin. Jason slowly rolled out of bed and followed his erection, which in turn was following Sylvia into the bathroom.

“What made you kiss me there?” Sylvia asked as Jason gently stroked over her pubic patch with a soapy hand. His other hand was exploring her cute bubble-butt. Sylvia was holding onto, and playing with, his erection as she leaned against Jason.

“I really don’t know” He responded. “It just seemed the right thing to do. I must say the hair is a bit off-putting but otherwise it was great. I assume you didn’t mind me doing it.”

“You can do that to me anytime you want” Sylvia said. “I will trim that jungle a bit so you don’t have to bush-whack your way to the target.” she added with a cute giggle.

“You seemed a bit surprised when I licked you” Jason commented.

“Duh, it was the first time in my life I experienced something like that” Sylvia said. “That orgasm was just as big a surprise”

“Why?” Jason asked in surprise.

“Because it was the first time that I ever felt anything like that” she said shyly.

“Really?” Jason was totally surprised. He might have been innocent and mostly ignorant but he was not totally ignorant as far as the dynamics of sex and masturbating went. He has been doing it soon after he and his mother moved into the duke’s castle and assumed girls did something similar. “You never gave yourself an orgasm?”

“Girls are taught, well, I was taught not to do anything that could damage my virginity, so no, I never did that.” she said. “I was a virgin when I was given to Richard and he never seemed to do anything to me that could result in what you did to me. I would have been happy, no, maybe content, with my life since I had no idea what pleasure sex could have been, until now. I sort of knew about orgasms and the joys of sex from talking to Richard’s secretary. She is a bit of a slut from the way she seduced the marines. She definitely liked what they did to her. I have always been curious and I even tried to nudge Richard into trying some of the stuff but he was a total stuck in the mud. I was not even allowed to wear sexy clothes.”

“Is that why I always saw you dressed as if you were about to attend a formal reception?” Jason asked.

“The way I dressed today would have had Richard freak out” Sylvia said. “I have been slowly relaxing the strictness of how I usually dress. I guess I should have asked you first before I get too used to dressing like today”

“Why ask me?” Jason asked in surprise.

“You are my guardian, our guardian” she said, “on the duke’s orders as well. You get to run our lives just like Richard used to.” Jason thought about what she said for a while. “You might have to do something about that girl body protector of yours” Sylvia suddenly said.

“Why?” Jason asked.

“She is showing a lot of symptoms of jealousy” Sylvia said as she pushed her nude body tighter against Jason. “She also has a crush on you. Just so you know, she peeked in here twice while we were busy. I guess it’s her job to make sure nothing happens to you. I guess we have been busy for quite a while. We should get dressed and join the rest of the world.”

They ended up taking another quick shower but without fooling around this time. Jason was already back in his pants by the time Sylvia was done drying her hair. He watched as she gathered her clothes that ended up scattered all over the floor. He was closest to her bra and picked it up but instead of handing it to her he folded it up and put it in his pocket.

“Souvenir?” she asked him with a grin.

“Not really” he said. “I prefer you as my souvenir. I just decided you don’t need a bra. Your breasts are gorgeous and small as well as firm enough not to use a bra all the time.” Then he reached for her panties and shoved them into his pocket as well. “Sometimes I will require you not to wear any underwear. The rest of today is one of those day” Sylvia giggled merrily as she stepped into her dress and started buttoning it up.

“Your wishes is my command, my lord” she said shyly.

“Uh, my lord?” Sam called softly from the door. “I’m sorry but you don’t have a secretary, and the phone kept ringing. The duke would like to see you in his office.”

“Go” Sylvia said as she threw Jason’s shirt towards him. “Come look for me when you are done” She only had the bottom few buttons tied up and was effectively topless but she didn’t seem to mind if Sam saw her like that.

Ron was standing just inside the office door, wearing a stony face while looking everywhere but at Jason. Jason glanced at Sam to see her keeping her face down. She seemed a bit red in the face as well. He wanted to ask them what was bothering them because it was obvious that both of them were off their normal behavior but that would have to wait until he was done with the duke.

“Had fun?” the emperor asked softly as Jason entered the duke’s office. The duke was sitting behind his desk while the emperor was relaxing on the couch. Suddenly Jason realized what could have happened. The emperor was looking for him and neither Ron nor Sam had the guts to stop the emperor, which was probably a good move on their side. Jason suspected the emperor had seen him and Sylvia together.

“You asked to see me, your grace” Jason said to the duke as he ignored the emperor’s comment.

“We wanted to talk to you about this dinner Lady Mount Grace invited you to” the duke said as he joined the emperor on the couch, and indicated Jason should have a seat.

“We both know it’s some sort of trap, we just don’t know how to counter it or what to do about it” the emperor added.

“What sort of trap?” Jason asked.

“I don’t trust those old barons” the duke said. “Mount Grace is a wuzz, totally under the control of his wife, the viscountess. She in turn has her head in the stars. She would do anything to get you to marry one of her daughters, as in your wife, not a concubine. My bet is that she already sees herself as the grandmother of a future emperor.”

“That is why it is a bad idea to let Mount Grace become the next duke.” The emperor said. “The Imperial Council will not go for her plans. While they are a body of senior and powerful dukes very similar to the Grendel council of barons, they do have a bit more say in how I run the empire. Their main objective is to make sure any future emperor is honest, mentally stable, and not sadistic or greedy. They will keep a close eye on you for a while before they will allow me to formally declare you my heir.”

“How does that play in what Viscountess Mount Grace has planned for me?” Jason asked.

“If the Imperial Council determine that you are being controlled by a woman, they will force me to not declare you my heir.” The emperor said. “The emperor has to be of independent mind and action. It will be the same if any potential heir to the empire is easily swayed by another person, somebody of weak mind.”

“I can see that could be a problem” Jason said.

“Somehow I just don’t see any of those old codgers or even Lady Simone herself forcing Jason into doing anything he doesn’t want.” The duke said. “I have access to his marine training records. He is a natural leader. He will have all of them eating out of his hand once they stop distrusting him. The purpose of this dinner is supposedly to introduce you to some ladies who could become the mother of the next Duke of Grendel, if you have to become the next emperor” The duke explained.

“Is there anything you would want me to be particularly aware of or to avoid?” Jason asked.

“I think as long as you are aware that they would all like to be able to control you then you would be fine.” The emperor said. Then he got a sly sneaky look on his face. “I’m particularly glad about what I noticed earlier. Don’t worry, I was on my own.” Jason glanced at the duke but he doesn’t seem to know what the emperor was talking about and was too polite to ask.

Jason could only assume that the emperor doesn’t see anything wrong in the new and potentially embarrassing relationship he found himself in with Lady Sylvia. He suddenly remembered about his new chief financial officer and the comment about her being abandoned by her husband.

“I have a question” Jason said as he addressed the duke. “I offered the position of Chief Financial Officer for House Taurus to a lady with a master’s degree in economics. From what I heard she did quite well until the company she worked for decided to ignore her recommendations and warnings. When they got into financial trouble because of that they blamed her. Her husband then abandoned her. What is her legal status now and can I actually appoint her as my CFO?”

“Does this have something to do with Sand Harbor’s financial troubles?” the emperor asked.

“Indirectly. He seems to have been a member of the group that got conned into investing and then lost their investment after they ignored this lady’s recommendations.” Jason said.

“Her husband just abandoned her?” The duke asked. “That is a nasty way of getting rid of a concubine. It should never be done to a wife without a judge getting involved. Are there kids involved?”

“Yes, two preteen girls” Jason said.

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