Jake

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Well Master, I quite enjoyed the spanking, but the crop was a little much. Maybe if there are things between spankings and the riding crop, I could stay there. I enjoyed sucking and licking on His Lordship's whore's tit, but I thought I was going to hurt her when I was biting her because of my inexperience. No one has tied me up ever, but if His Lordship would be so generous, he could demonstrate on me some novice ways to be tied up so I know what it feels like, and what I am comfortable with, then a few ways to push my boundaries. I don't want to be trussed up like a turkey and wind up having a panic attack. I want my first time to be enjoyable, even if I don't do very much tonight, or there may not be a second time."

"Very well said, both of you. I think I have a solution. Both of you will spend the night in a different area than the orgy with a personal trainer. I will have a close friend bring her novice kit with her. At the end of the night, she will know your body, and you can sign up at some sites to get your stuff. Both of you need testing for STD's and Beth, you need to get a birth control implant; they last three-years and are over 99 percent effective. You need a medical STD testing every six months. It is a requirement for anyone attending my orgies; we like to make sure everyone is clean."

"Jake, you need to know Beth's body better than she knows it. You will need to act on the slightest change in her actions. Beth is a newborn to this lifestyle, and both of you need to navigate how you want your relationship to work. Beth is in a unique situation, she wants to be your submissive, and at the same time, she has obligations to many, to have her in charge."

"Master, my staff, and clients will know Master comes first, business comes second, of course, I may have to leave to put some fires out. When we go to leave, what time do you want wheels up? We will go over menu choices tomorrow. I suggest mid-morning so we are there before sunset."

"OK 10:00 AM."

Beth took out her phone, "Charlie, hi it is Beth, wheels up 10:00 AM Tuesday. I want you, Dave, Gretchen, and Tina. See you then."

"Chuck, it is a go for Tuesday, a car will pick you up at 9:00 AM."

"Daisy, how would you and the girls like to go house hunting for my Master? I will send a car for 8:00 AM Tuesday morning."

Jake noted, "What was that about?"

"Preparations for our flight Master, except for the food, may I remind you, you order what I eat. I have an extensive menu at home, but he is a gourmet chef, so you can order anything you want as long as we give him some heads-up."

"Thanks for reminding me, I keep forgetting all those little things. You will be relieved to know, you don't have to tell me about going to the bathroom. I have friends that go five times a night, while others sleep right through the night. That changes when you get sick also. Why the hour difference with your roommates?"

"You don't think the girls would do the sensible thing and pack the night before do you? So, I gave them an extra hour. When I am in boss mode, I do not feel I need to repeat myself; it is a waste of time and energy. All three of you have passports, correct?

"I do, I think it will take a while to get used to this, it took you five minutes on those calls."

His Lordship groaned when he heard the lame jest Jake just made. Everyone was excited about the trip. His Lordship's whore and Beth's roommates never flew in an airplane before. At 07:30 AM Beth's roommates were always looking out the front door for their ride; seven suitcases and a garment bag were lined up near the entrance. Daisy knew Beth had her Go bag at her office, but she packed some clothes for Beth and brought her purse.

At precisely 08:00 AM the stretch limo appeared, the driver came in and put all the bags in the trunk while the girls piled into the back. When the driver pulled away from the curb he said, "I came early because Miss Beth said you would not be ready. There is a bag of breakfast sandwiches there for you, each with your names. Also, there are bagels in the other bag."

The girls squealed, "Are we that predictable? She normally would have been right, but who could sleep. We didn't even have time to eat yet. I hope I won't be too cramped in my seat during the flight, I have long legs you know." The driver just smiled.

The realtor just finished arranging some possible places to buy; if Mr. Jake didn't like what he saw, he was going to stay in North America. Beth didn't like sites that were too hot, and she avoided the hurricane and tornado-prone areas. Her gem was in the Canadian Rockies, but the US will be first.

The group of four were was eating breakfast at Jake's house. Beth insisted on packing everything for her Master, in accordance with what His Lordship's whore had done for her Master. Beth will learn a lot from her in the next two weeks.

The girls were confused when the car passed all the commercial departure gates. Once the entire group assembled in a spartan-looking room, Gretchen and Tina introduced themselves to the group and said they would be serving them during our two-week trip. The captain was doing final checks on the plane. As everyone was on the shuttle to the jet, His Lordship said, "I am a bit of an aviation geek." Whore frowned at her Lord. "OK whore, I am a huge aviation geek. That is a Gulfstream 650 over there. I think I died and went to heaven."

Beth said, "I know the Captain personally, perhaps I can persuade him for you to peek inside some time."

"No way, that's awesome!"

Daisy said, "Your Lordship, can you let the rest of us into your conversation now?"

"Don't you get it? The Gulfstream 650 is the gold standard in private jets."

Daisy said, "I get it, guess which jet we are going to fly on." The whole shuttle was silent and dumbstruck; Beth couldn't help but beam.

Once in the cabin, Tina explained, "Your chairs recline into beds, your smartphone controls the movies, lights, and shades on the plane. Around noon eastern Eastern time, we will have lunch. Just let us know if, you need anything; girls it looks like you might want a blanket and pillow to get some sleep."

"Are you nuts, sleep during an experience like this?"

Once the plane reached cruising altitude, everyone broke into their areas. His Lordship's whore, went up front to get some sleep. They were traveling at 41,000 feet, so there was not much to see.

"Miss Tina, do you think when the Captain is free, he could talk to me about the plane? It is a golden opportunity of a lifetime." Later, His Lordship was having a walking tour of the plane, including the cockpit. He was like a kid at Christmas time, and got the best gift ever.

Chuck, the realtor, was with Jake and Beth, sat around the table reviewing the properties. "... and that is about all of them Sir. Personally, Beth took her gem off the table because it is not in the US or you can't work twelve months a year there."

"Wait for a second. Are are saying there is even a better place than all these other fantastic places? Where is this place?"

"Yes Sir, I hope I have not overstepped my bounds. It is in the Canadian Rockies. Sir, you may not be able to work all year."

"Set it up for the end of our trip; the best for last. If I am going to move my whole team and my team's families, I want to know all my options. You, of course, will be at that meeting to explain the pros and cons for of everything."

Tina approached Beth, "Miss Beth, could Gretchen and I watch a movie with the girls? Miss Whore is fast asleep, His Lordship is with the Captain, and you are here; they are the only others on the plane to serve."

"Permission granted, as long as you serve any who need help."

Tina came back to the multimedia area and said, "Miss Beth gave us permission Gretchen." Soon all had sodas and popcorn and were engrossed in a first first-run chick flick.

"Well, let's include that in your expected demographics. Healthcare, materials, exchange rate, are all beneficial."

"I am sorry Master; I did not think of those other things. It would make a big difference in take-home pay." The next surprise, a helicopter trip to the first mansion.

Dinner was served on the plane an hour before landing; everyone was tired when they deplaned the helicopter. The entire staff, all lined up outside the manor house welcomed the entourage.

"Master, we try to hire as many locals as possible to help the economy. A management team handles HR and Admin; locals hiring and firing other locals can get messy."

"I take your point. What do these people do when no one is here?"

"Master, that is hardly ever the case. Usually, most places have twenty to thirty people here year-round, depending on the business, contracts, and time of year. Sometimes up to one hundred may stay at a mansion. Right now, this is a slow time for this mansion; it is why we are here first."

"We are very proud of our town's school system; we have a one hundred percent graduation rate. Last year, the boy's baseball team was in the playoffs. We encourage a high profile with the manor people and the town; they go to school recitals, fairs, ball games, whatever they like. The village adopts them. Almost all of them are on a first first-name basis. I think we should turn in for the night; it has been a long day."

An hour later, Master barged into Bitch's room. Master put a black suede choker on her neck with a heart on it. "This is your office collar Bitch. It is inscribed with a "B." Most people will think it stands for Beth, but we both know it stands for Bitch, don't we?"

Bitch nodded her head.

Master grabbed her wrists and pulled them behind her back and attached straps with loops on them. He secured both her wrists and ankles so far apart. "You have forty inches of slack Bitch, but I am going to move your legs so widespread you will strain your arms."

"Bitch, you will love this sleep mask." The mask had Bluetooth earbuds. Master went to his laptop and selected white noise and elevated the volume. The sound permeated Bitch's skull, and she could hardly think.

Master sheered all her clothes with a knife; he rested the cold, steel, blade in between her tits. Bitch shivered as her bra snapped. Finally, Master revealed her panties; a large dark spot showed on her gusset. Three flicks of the sharp knife later and both halves of her panties fell onto the floor. The panties were shoved into Bitch's mouth; the smell invaded her nostrils, and every lick made the scent stronger.

Bitch could not see, hear, and for all intents and purposes, she could not smell or move either. Master started using a deer flogger on her; it did not hurt as much as a spanking. Bitch knew the session would last all night. Master put Bitch over his lap and gave her twenty fast swats. It put Bitch on a low simmer, and she swayed her ass to get more. Master changed where and how fast he gave Bitch a swat. To her, the delay seemed like an eternity; the anticipation created a trickle of juices rolling down her thigh.

One time His Lordship came in and had a five-minute conversation with Jake. Bitch had no idea what was going on. The white noise combined with her scent was so intense, Bitch had to crawl into a corner of her mind to get away from reality. The only thing Bitch knew was there was another swat coming.

"That poor girl, there is no way she is going to cum as long as Jake uses that flogger," noted His Lordship as he exited the room.

Jake put several actions in motion that Beth was unaware of before they left on the trip. He called the trainer and received a list of accessories that he would need as they grew into the lifestyle. Charlie gave him all of the mansion addresses; he sent various packages to all the mansions. He tasked His Lordship, his whore and Tina to make a floor plan of all the basements they visited with an eye to making a full playroom as well as adding some pieces to other rooms.

The meeting on the jet was a show for Beth; Jake saw a full video tour of all the mansions including the ones for sale; the lone exception was the mansion in the Canadian Rockies. That was the job of a Master, to know more than a sub thinks you know. The business side will be harder, most likely just a general overview will be needed.

After three hours of torture, Master changed to the small paddle; Bitch was well primed, and fireworks filled her mind as it soared into the air after she came down from the clouds she had wave after wave of climaxes, for thirty minutes, leaving her a limp rag doll. Later, she surmised that is where whore went.

Master exclaimed, "Let's all take a tour of the place on horseback. They have some exquisite creatures in the stables."

Whore commented, "Perhaps I should go to her."

"She gets no pampering; I need to know how badly she wants this training. I think being submissive and a top executive will be a hard transition. The question is "Can she handle this lifestyle?" Your Lordship, would you allow your whore to become a mentor to Bitch? Having been there already, she would have more seniority and could discipline Bitch." Master never used the name Beth anymore. He never used Jake anymore; everyone recognized that Bitch was now a lower class of citizen than she was forty-eight hours ago.

The tour was fantastic, the gardens were immaculate, even some hidden places for picnics or swimming. Whore packed lunch for everyone, and the horses drank at the watering hole and had apples and carrots.

Bitch was able to make it to dinner; she immediately sensed the whole dynamic had changed overnight. Whore's gaze bored through Bitch. She was trying to communicate her commands without saying a word. Bitch looked at the floor. "How may I serve you, Master?"

Bitch served dinner but didn't eat with the others. She waited two hours after dinner before she was allowed to eat and then dinner was a cup of soup. The Chef screamed, "I am only giving this to you because Master commanded it; you do not deserve it. You made me dirty another pot and cup in making the soup for you," with that Chef took a wooden spoon and beat Bitch until she was out of breath.

Each of the castles was on two hundred to five hundred acres and each had the top of the line security. As the group visited each mansion, a pattern formed. His Lordship loved the ones with gardens. Tina loved the ones with stables, as she grew up on a farm. Bitch's friends loved the streams, lakes, and waterfalls to go skinny dipping as well as other naughty activities. Gretchen loved the ones with a gym and infinity swimming pools. Bitch had no vote, and the Master was holding off his opinion until he got all the information.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

Similar Stories

Stress Relief A married couple submits to a group of horny young guys.in Group Sex
How to Receive a Facial Cumshot Learn how to receive a facial—and how to make it extra hot!in How To
Sasha's Business Trip A beautiful, confident whirlwind on her first business trip.in Erotic Couplings
Bimbo Bedroom Ch. 01: Bar Surprise Kieran sits in a bar when a stunning blonde walks in.in Transgender & Crossdressers
Stevie 01 There was a chance of seeing the aurora borealis lights.in Transgender & Crossdressers
More Stories