The Duke's Dilemma: Regency Romance Menage Short Stories

by Lacoste, G. G.

  When Cynthia had first seen the Duke and Duchess together they were like a magical combination. They looked perfect together. As she looked at them she thought to herself, this is what she would want in the future. Of course, she didn’t know that she would be invited into their bedroom at a later time either. Her outlook changed quite a bit that first time, and all for the better. She would become friends with them at that point, but also more.

  It would be her looks that drew the attention of both the Duke and Duchess, and the fact that whenever she would go to their room, Cynthia was always very pleasant. She smiled as she thought back to that day when she walked in on them. She had been quite shocked at finding the Duke and Duchess both naked, and entwined in their love making ritual.

  Cynthia had looked down and tried to leave immediately, but the Duke had told her to stop. He had said it with so much authority, that she hadn’t dared move. They had stopped what they were doing, and had brought her into their fold. The Duchess Priscilla had shown her how to suck the Duke’s cock. It was huge, Cynthia thought for sure there would be no way she could ever fit it all into her mouth. However, by the end of that day, she had mastered the task, and from his moans she had been doing a great job!

  That first time she had learned a lot about sex, and how good it had felt. From the Duke placing his mouth on her pussy and taking her out of this world to sitting on top of the Duke’s huge monster dick and having it deep inside of her. That experience was one that was simply amazing. She could remember it clearly, because at that time she had been so very nervous.

  The fact of the matter was though that the Duke and Duchess had her so worked up, she was more excited than nervous. However, when the Duke had ordered her to sit on it, she had hesitated, looked at the prick that stood like the tallest tree she had ever seen in the woods. No it hadn’t fit in her mouth well, what about her pussy? How could this work? But the Duchess had helped her as well as the Duke and soon she had his full member inside of her. The feeling was exquisite, she had been so full, his cock had jumped inside of her and the pleasure she felt had been shocking and terrific.

  While she moved up and down slowly on him, he had grabbed her waist and moved her more quickly. It had been thrilling, her body kicked into overdrive, her pleasure sensors fired at double time. She screamed as an orgasm had rocked her body, it would be only the second one in her life she had ever experienced an orgasm.

  The first had come earlier at the tongue of the Duke. She smiled at the memory of how his tongue felt. He had moved it expertly, tantalizing her more with each and every stroke of. His tongue was a magical tool to her mind and body. She remembered he had sucked in on her nub, and stars of pure pleasure had exploded inside of her head. That was just the beginning of the pleasure though.

  He had continued to suck on her nub and lick on her slit for several minutes. Switching back and forth, changing the type of pleasures her body felt. Then he had settled down on her nub a bit more and when her body was rocking up to match his sucking, he had placed a couple of fingers inside of her snatch. She felt a strange yet pleasurably sensation sweep across her body. She moaned loudly, then that turned to a scream as he continued to play with her pussy lips and push in fingers deeply into her. At that time she hadn’t known that it was an orgasm, but whatever it was she wanted to experience it as often as she was able!

  They had been in that room for hours that day, and she had loved every second of it. So when it came time to experiencing licking her first pussy, the Duchess’s, she had been ready. Cynthia was worried she wouldn’t know what to do, or how to do it. But with a bit of instruction, the Duchess soon had been moaning from the use of Cynthia’s tongue. It had been just as thrilling as everything else she had experienced that day.

  After she moved out of her parent’s house they would often times stop by her house. The Duke and Duchess were thankfully very kind and caring people who her helped with the house. It was much easier to meet with them when she didn’t live with her parents. Because simply put, there were days when she didn’t need to work, but she could use some fun sex.

  Besides, the Duke and Duchess Cynthia had other sexual partners as well. Two of her favorite’s where the Twins who worked the stable. They were handsome, and well hung. To her it was a great combination and one that made their sexual sessions so much more enjoyable.

  Thinking back she could remember the first time she had approached the twins. It was a bit after her first time with the Duke and Duchess. She had felt like she had been missing out on so much fun, and she reacted like a cat in heat.

  She had walked into the stable, and had spotted only one of the twins at that time. She had already disposed of her undergarments, so it was quick for her to undress. Cynthia had pulled her dress up over her head to show the twin what she was offering to him.

  Of course, she hadn’t expected the other twin, who she had spotted, to sneak up behind her. Her experience had been one of pure pleasure that day. The twins had worked her body over well, and in fact another person had come into the stable as they were in the middle of sex, and had joined them as well.

  The twins, Gary and Barry, they had some big dicks. Hell, she had thought the Duke had been huge, so you could imagine her shock when on that day in the stable she had seen two cocks that were larger. The fact that she was a bit nervous would never have been obvious to anyone but her on that day.

  Cynthia had taken it like a trooper. First she had sucked Gary’s cock, or so she thought. At that time she hadn’t really known which twin was where and who was doing what, they were, after all, identical.

  The fat cock had fit in her mouth part way. While the other twin had licked her pussy, just like the Duke had, and soon she had reached an orgasm. Her scream came out around the dick in her mouth, and shortly after she had pushed her mouth down on his dick once again, and it had exploded, spilling the juice inside of her mouth and shooting towards her throat. It had tasted delicious, and she was looking forward to more of his sperm in the future.

  By the time she had finished off Gary’s cock, the other brother had flipped her on her knees, and began to push his massive prick deep into her. It had been a fabulous experience. He was so big and with the position he had placed her in, she felt like he was going to skewer her.

  Cynthia had screamed in the throes of passion as he pounded into her snatch. Rocking her back and forth as she rode his member as best as she could. He was in complete control though, and Cynthia had loved it.

  After a bit he came, and it was around that time she had felt the extra dick. Barry had placed his penis into her mouth, and the other twin had placed his into her warm and wet hole. At that point she had felt something trying to penetrate her ass.

  The fact was she was so excited and the pleasure she had already experienced from the twins had her mind mushy. The third man had pushed into her anus slowly, but once he was inside her, he pummeled her. The two dicks inside of her had pushed her over the edge and she had screamed as a massive mind blowing orgasm had shot through her body.

  Cynthia smiled as she sat in her living room thinking back to the past. The twins still came over once in a while, and had become quick friends. Better yet they were almost constant lovers in one way or another.

  If both of them came over she knew she had double the fun. Once in a while though if there were work to be done, only one of the twins would show up. The funny thing was she didn’t really know them apart, until they dropped their pants. Not that one was much larger than the other but Gary had a little mole beside his penis, and it was the only way she could tell them apart.

  There was a knock on her door, taking her out of the past and into the present. She went to answer it and speak of the devil one of the twins was at her door.

  “Come on in.” She smiled largely, knowing exactly what he was there for.

  The twin, whichever one it was, leaned over and kissed Cynthia, she gladly and passionately kissed him back. “Hope you don’t mind a visitor,” he
smiled.

  “Of course not.” Cynthia knew better than to ask which twin he was. It was like their joke to make people wait to figure out who was who. She had tried it once in the past, only to find out that the name she had been given was wrong, only after he had his dick in her face!

  She stepped aside to let him into the house. He strode in and she enjoyed the look of him from behind. He got inside and turned to her and kissed her again deeply. Probing her mouth with his tongue, she wrestled back and they both moaned in pleasure.

  “I don’t have long, I’m sorry. I was hoping to have all afternoon, that way I could do everything to you I’ve thought about all day!” He stated.

  “Anytime is nice!” Cynthia commented.

  He pulled her dressed up over her head, and quickly disposed of her undergarments. This was one of the few days she had actually put anything on under her clothes. Normally she would simply just throw on a dress, and be completely naked underneath.

  Cynthia noticed the short of work he made of the clothes though, and as soon as her clothes were off, his were dispelled with too. She looked down to see no mole, so it was Barry. He was the bigger of the two brothers in the endowment area, but not by a lot. Still just a little could make the experience all that more pleasurable.

  Cynthia pushed him down on the couch, and positioned her pussy to his face, where he gladly lapped at it. His tongue pleasured her love hole, and he sucked on her clit as well. She squirmed from the feeling of his licking. Cynthia wanted to give him pleasure too, so she lowered her mouth to his prick, and pulled it into her mouth.

  As he played with her pussy lips with his tongue and fingered her clit, she moaned loudly. He switched and plied her nub with his mouth and stuck a finger into her snatch. She screamed around his cock as he drove her over the edge and into an orgasm.

  He moved her around so that she could sit on top of him. She lowered her wet hole down onto his hardness and moaned. It felt so good to be on top, she loved this position. This had to be one of her favorite ways to have sex with anyone!

  “I’m sorry Cynthia. I know you would love to screw all afternoon, but I really don’t have long. Hopefully later on tonight I can visit again!” He stated as he moved his body up to meet her downward thrusts.

  “That’s fine Barry, this is good.” Cynthia smiled largely as she got closer to another orgasm.

  He grabbed her waist and man handled her by moving her up and down at a speed that she would never be able to maintain. It was all she had needed and she was in heaven as he pummeled into her harder and harder. She felt him tighten up and fill her up with his sperm, he moaned loudly as did he.

  “I’m really sorry I had to rush it. Maybe I’ll tell Gary to come over when I get back, if he’s done with what he was doing.” Barry apologized for the short session.

  Cynthia kissed him deeply. “It really is okay, but if you want to send him over I’m good with that!” She laughed.

  “That’s my Cynthia. Always looking for more dick.” He laughed, as he got dressed.

  Cynthia waved goodbye to him. That had been one of the shortest times for them. Usually, if he were rushed, he would still be able to stay for a bit longer. They must be swamped at the stable. If Gary could make it over she would be very happy, if not, she knew later on she could always go and see the Duke and Duchess!

  She dressed and went to make a bit of lunch. Cynthia hadn’t noticed just how famished she was, not until she had a few orgasms!

  Getting out the bread and meat, she made up a small meal for herself. She thought back to another time with the Duke and Duchess. They were always so giving when they had sex with anyone. It had been a time when they had stopped over for a visit. Of course almost all visits from them would end up with the three of them having sex. Sometimes Cynthia would invite other people over too, that way there would be more action.

  The time she thought back to was one afternoon when she had invited the twins to come over along with another worker from the castle. The twins had pleasured the Duchess, while the other girl and Cynthia had done many wonderful things to the Duke. He gave back just as much to them. It had been a great afternoon.

  Cynthia smiled thinking of how it had been sitting on the couch, with the Duke licking her pussy so expertly. She had squirmed a lot. He did this special thing with his tongue that just drove crazy every woman he ate out.

  She had looked over at the Duchess and the twins part of the way through one of her many orgasms. The Duchess had screamed so loud it was almost frightening. Once Cynthia looked she knew why. The twins had her up on the table. The Duchess had been sitting on one of the cocks, which was firmly inserted into her ass, and the other had been ramming her pussy hard.

  Cynthia loved this position with the twins. Though the first time it had hurt a bit. After all, those boys were big! They had been very gentle with her and had made it very pleasurable indeed. There was something about their two huge dicks, one in each hole, that made Cynthia so wet when she thought back to the times she had experienced it.

  That day she had smiled, knowing exactly what the Duchess was feeling. The Duke had fucked her well that day, but after the Duchess and Duke had left, the twins had given her more. She requested that they do the same thing they had done to the Duchess earlier in the day. Cynthia felt her pussy moisten at the thought of that experience.

  She sat and ate her lunch as she relived the experience in her mind. The feel of the dicks in her pussy and ass, it had made her feel like she was filled to and beyond capacity. They had stretched out both holes that day, but she had many amazing orgasms along the way!

  There was a knock at the door, stopping her mind, and bringing her back to the present. She smiled broadly hoping it was the other twin, Gary. Cynthia walked to the door and opened it; it wasn’t the twin at all, but one of the younger soldiers in the brigade.

  He looked down at his feet when she answered the door.

  “Yes, can I help you?” She asked.

  When he looked up his face was red as an apple. “I’m sorry ma’am to bother you.” He stuttered. “But some of the guys were saying that, well. I’m not really sure how to say this.” He stopped and looked down at his feet again.

  “Come in.” She pulled him inside. “Now what are you trying to tell me?”

  The kid looked barely eighteen years of age. He was young and his face still had the baby fat that normally falls off your face shortly after you become a man. Heck, she looked closely at him and noticed that he still had only peach fuzz on his face, not even the whiskers like a man would grow.

  “Well ma’am, they said you would help me become a man.” He stuttered, his face brighter than ever.

  “How old are you?” Cynthia asked.

  “I just turned 18 ma’am.” He said smiling brightly.

  “And just how did they tell you I would turn you into a man?” Cynthia asked. She knew, but the fact was if she was going to have sex with this man-child, she wanted him to at least say what he came to do.

  He blushed again, with the redness creeping from his head to possibly his toes. “They said you would let me have sex with you.” He said cautiously.

  Cynthia looked at him again closely. She had done it in the past, the guards knew that she loved sex, and they had sent many new men to her. Barry had left her still a bit horny, so it wasn’t that, not at all. However, there was a bit of training you had to do with a person who never had sex before. She would have to tell him how to do things, and did she have the patience for this right now?

  “Well, first tell me your name.”

  “My name is Andrew ma’am.” He smiled brightly, sure that he was going to get his first piece of ass!

  “Please you must stop calling me ma’am. You know I’m not that much older than you right?” Cynthia stated.

  “I’m so sorry ma’am. Oh no I’m sorry. What do I call you?”

  “Just Cynthia is fine.”

  “Yes Cynthia. Well were they just messing with me, or is i
t true?”

  “Today is your lucky day Andrew. The fact is I’m still pretty horny and you just might be the cure for this itch I have.” Cynthia laughed.

  Andrew just looked at her, unsure of what she was talking about. But he smiled widely, knowing he was indeed going to no longer be a virgin after he was done here.

  “I’m ready ma… sorry Cynthia.”

  Cynthia shook her head, wondering if this was the best thing to do. “Take off your clothes. If we have a next time I’ll show you how to undress a woman the right way.”

  “Is there a right way?”

  “Yes you can do it sensually and make her even more excited, or you can do it wrong and then she may not be near as excited as she could be.”

  “Oh, okay.”

  She watched him undress. Poor little Andrew was already excited and rock hard and his dick sprang out of his underwear. Cynthia appraised the cock in front of her, not bad, not huge like the twins, or even the Duke, but respectable. He was much wider around maybe 4 and one half inches, and about 7 inches long. She could work with this!

  Cynthia took off her dress to reveal her naked body underneath. She saw a spark light in Andrew’s eyes and it was pure lust. “Alright, You may not last very long your first time. Don’t be embarrassed. Just remember that you are young, and it will take you barely anytime at all to get hard again. Your stamina will make up for your staying power for quite some time.”

  “Okay. But I think I will be good.” Andrew spoke the talk of young men everywhere who thought they would be able to last a long time, no matter what happened.

  She thought about the best way to do it for his first time. Cynthia knew it would be a long afternoon, if he were like most 18 year old men. Finally she decided to lie back on the couch. “Alright, first in most cases you’ll need to get the woman ready and that means foreplay. Have you ever done anything sexual before at all?”

  “I’ve masturbated.” He blushed.

  Cynthia laughed. “What young boy hasn’t? Well you are going to learn how to lick pussy right now.”