Summer Surprise Pt. 14

William Thornhill brings Matt, Dianne, Rosilyn and Chloe to New York. Brianna Worth is there to assist Bill in training Chloe along with her slaves, Monique and Adele. Rosilyn chooses Brianna as her new Mistress. Adventures are had by all. This chapter contains oral, anal, lesbian and multiple partner sex. It contains Dominant/submissive behavior and training involving punishment including spankings. COVID-19 and STD's don't exist in this fantasy world. Thanks to JohnnyGalt for making everything better.

Summer Surprise, Pt 14 - New York 1

Over the next few days, the pattern remained the same. Matt went to job interviews during the day while the others enjoyed each other and Chloe exhibited the depth of the control she exerted over Dianne and Rosilyn. The others were amazed at how freely either of the slaves would open the door, despite being naked. Dianne opened the door for a UPS delivery and Rosilyn for a Chinese food delivery. They had tailed plugs in their asses except when someone chose to fuck that particular orifice. The non-slaves frequently remained naked because it was convenient if they had nowhere to go, even Ethel and Georgina, despite the presence of Ethel's chef, René. René frequently partook of Rosilyn and occasionally Sophia. On Tuesday night, Sophia spent the night with him as she'd said she would.

In the afternoons and at night, the pattern changed slightly. Matt would return from his job interviews and usually have sex with Chloe or Dianne. Georgina and Elaine had to work in the evenings. Elaine's hours increased during the summer months when she was off from college, working five nights a week instead of two. When Georgina left, Ethel refrained from having sex with anyone, reserving that for when she was with Georgina. While the others were at work, they had a couple movie nights, with Chloe explaining why certain scenes of movies were so effective in drawing in the audience. Usually the two slaves were in use somehow. Sometimes, it was no more than sitting in someone's lap while they were teased and caressed, other times, they provided sexual services which were provided in front of everyone else.

Each of the slaves was whipped four times a day, so they were constantly covered with a fine web of red lines which slowly dissipated over the next couple hours. Sometimes Chloe doing the whipping, sometimes Sophia, sometimes both. Frequently, they were whipped for cumming without permission, other times just to maintain the stripes. Tuesday night, Dianne spent the night with Ethel and Georgina, and on Wednesday night with Beth and a friend.

Beth invited her platonic lesbian friend for a sleepover Wednesday night. Not being a lesbian herself, Beth never did more than kiss one of the others after they entertained her, and since she wouldn't have sex with her friend, Dianne was provided to her as a special treat. Elaine accepted sexual favors from Rosilyn and Sophia, but never returned them. She nearly always returned those of Dianne and Chloe after Monday night.

Denise inquired about them on Wednesday, but didn't make a return visit. She told Elaine and Georgina that after going home, she was fucked three times by Donald, two times more than he'd performed any time in the last couple years. He'd also fucked her twice Tuesday night.

On Thursday morning, Beth went with her friend to the mall after they got up. Ethel and Georgina were sleeping in, unused to the crazy hours and rampant sex. René, Sophia and Rosilyn were trying out several FFM positions on the patio. Both Sophia and Rosilyn had enemas before they started so either of them could suck René's cock after he'd fucked the ass of the other.

Chloe took Dianne to Elaine's room where Dianne woke her up by licking her awake. Chloe then joined Dianne in giving Elaine a number of strong orgasms, by simultaneously licking both of her nether holes.

They were lying in a loose bundle of limbs on Elaine's bed, panting.

"You two are some nasty fucking bitches," Elaine said. "That was incredible. Thank you."

"Speaking of nasty fucking bitches," Dianne said. "Do you know what I'd really like to do now?"

"I haven't got a clue."

"I'd like Matt to fuck me while you lick my clit. Mistress, Matt and I do something similar all the time; sixty-nine while he fucks either a cunt or ass."

Elaine was stunned. "Jesus! Do you know how close to incest that would be?"

"I do. The perverseness of the idea adds to the thrill for me. But it wouldn't be, if we did it right."

"His dick would be right next to what I'm licking."

"Not if he was fucking Pet's ass instead of her cunt," Chloe said, thoughtfully. "There'd be sufficient separation from your mouth to Matt's cock, but you couldn't sixty-nine or he'd be teabagging you. That would be too damn close to incest. Maybe if he were sitting in a chair and Pet rode him. I could lick you so you got something out of it."

Silence ensued as they considered the possibility. "I can't believe I'm even thinking about this," Elaine said.

"I'm not the only one who thinks this is intriguing, right?" Dianne asked. "Just thinking of it has me ready to cum."

"We don't have to make any decisions about this," Chloe said. "Let it percolate. When Matt gets back, Pet can ride him on a chair facing forward. If you're ready to do so, start licking her pussy and clit. If you're not, I'll do it to start. If you want to join in or take over after I start, feel free to do so. Pet, take enemas right before lunch so I can clean Matt's cock afterward."

"Yes, Mistress."

Which is how when Matt got back from his last interview, Dianne sucked him hard after he'd eaten, lubed him and her ass, and slowly sank over his prick, feeling him fill her ass. Chloe came over and started licking her cunt and clit, stirring enough in itself to cause Dianne to orgasm frequently, but when Elaine came closer to watch, then tentatively began licking her with Chloe, with Chloe finally backing away and leaving it all to Elaine, Dianne went off.

The thought of Matt's sister licking her pussy while Matt fucked her ass struck such a deviant chord within Dianne, the orgasms started piling one atop another, soon melding into one incredibly powerful orgasm. When Matt shot his cum deep in her bum, it caused Dianne to squirt all over Elaine's face, shocking Elaine enough she fell backward to the floor.

Chloe helped her off the floor. "Pet does that sometime when she gets super excited. I got a face full too when I fist fucked her. Give me a minute to clean up my lovers and I'll help you shower. Pet, you have to mop the floor."

"Yes, Mistress."

Chloe sucked Matt's cock clean, then licked the cum seeping from Dianne's ass. Chloe stood up when she was finished, and taking Elaine's hand, went to Elaine's room to shower. Dianne mopped the kitchen floor.

Ethel and Georgina had been cleaning up the kitchen when all of these events went down. At first, Georgina had thought to intervene, but she saw how carefully and assiduously Elaine had stayed away from her brother, close as he might have been..

Matt left to get a shower of his own and after Dianne finished mopping, Georgina confronted her.

"What was all that about, Dianne?"

"Elaine satisfied a fantasy of mine, Georgina. I had the idea that Elaine licking me while Matt had sex with me would be wildly exciting. It was. You saw how I squirted. It would probably be even more twisted and exciting for you to lick me in the same circumstance. So close to being totally deviant, but remaining legal. Being a submissive is releasing a lot of sexual fantasies for me. I never imagined so many wicked ideas would keep popping into my head, but there they are, bubbling up."

"Does Chloe normally go ass to mouth?" Ethel asked.

"No, ma'am, only if we've cleansed ourself with enemas beforehand to ensure we're clean. Generally, we use a mild soap and water mixture several times, followed by a plain water rinse. It used to take several before the water was clear enough we felt clean, but we've done it frequently enough, we can usually quit after two as there's no build up anymore. Honestly, it's no different than cleaning him after he's been in our pussy. I was nervous about it at first, but now I'm perfectly comfortable doing the same thing. So's Matt, Sophia and Rosilyn. We all do it. Chloe said the thought of me doing something so subservient as licking Matt's cum out of her bottom made me feel more submissive and her more Dominant, but she doesn't expect me to do anything which she herself refuses to do, so we all do it, except as a submissive, I do it more. We all like anal sex. Even Matt gets pegged on occasion."

"Make sure nothing you do crosses that line, Dianne," Georgina said.

"Yes, ma'am. I know how devastating it would be to people if that line was crossed. I guess I'm thinking of it in terms of the doctor's oath, 'Do no Harm'. Just as gays want to be accepted and allowed to love who they love as long as they don't do harm to another, that's what I'm thinking of in terms of what I'm willing to do. Denise was encouraged to speak to her husband and talk to him about what she was going to do. She didn't cheat on him. I wouldn't have sex with a married person unless they were both good with the idea, like you two. It's why René was chosen instead of a married person, because he's single. I would never be on board with forced sex or underage sex or sex with mentally incapacitated or drugged people who can't make a choice. That's doing harm. Anything which doesn't, might be something I'm willing to try except for certain things I know I won't do. It's also why I have a safe word. I don't have a problem with Mistress whipping me, but she needs to be careful, and if it were under circumstances where the pain is too much or it's something harmful to someone, I can stop it."

She kissed both of them and showered herself, then it was time to get ready to go to New York. They bid adieu to Sophia who was going home. Ethel drove them to the airport to catch a ride on Bill's private jet. Both Dianne and Rosilyn were wearing tails again.

On boarding the plane, they found there were three other passengers, two of them naked. Seeing nudity wasn't an issue for others on the flight, Chloe had both Dianne and Rosilyn strip. The beautiful, clothed woman called Dianne over when she was naked. Chloe told her she could go and Dianne stood in front of her in her Display position, assuming she was a Dominant as the other two were collared slaves.

"This jewelry looks like one of my pieces. Adele, could you confirm that for me?"

"Yes, Mistress," one of the slaves answered and she knelt down and inspected Dianne's pussy jewelry, making Dianne moist up.

"It is one of ours, Mistress. A very recent piece. Her Mistress is Chloe by the jewelry."

"Then you must be Chloe Hamilton. Bill has told me a lot about you. My name is Brianna Worth. These are two of my slaves, Adele, and Monique, also my wife."

Chloe shook her hand. "The Brianna of Brianna's Baubles. I've heard a little about you, but not a lot. This is my slave, Dianne Rogers, or Pet, the one with the jewelry, her boyfriend and my lover, Matt Sanders, and my other slave, Rosilyn Bechtold, or Slut."

They all shook hands with each other.

Brianna smiled. "Why doesn't the other one have slave jewelry? Haven't had time to do it yet? We do piercings as well. Monique is quite professional. It's a service we frequently do for our more expensive, exclusive pieces as yours was."

"I haven't tattooed and pierced Rosilyn because I don't intend to keep her past the end of July. I've graduated, along with Matt, and I'll be leaving La Crosse. I'm essentially poor and can't drag my slaves all over the country, plus, taking Pet would be a disservice to her boyfriend who hopes to remain close after he gets a job. I feel I may be able to Dominate one remotely and do well by her, but not two. I'm hoping she'll find a Master or Mistress to accept her submission after I leave and I won't change her body for such a brief time. I'm keeping Dianne because her submission saved my life."

"That sounds like an interesting story," Brianna said.

"We'll have the whole flight to tell it. Why are you going to New York? Business with Bill?" Chloe asked.

"I believe Bill invited us to help train a young Mistress whom I suspect is you. A couple of Broadway shows and a full day of intense training on Sunday and Monday morning, followed by a return trip home."

"He said he'd have someone to help, but not who it was. You said Adele and Monique were two of your slaves. How many do you have?"

"More than two dozen. My business is essentially mostly slave labor in a sense. Instead of receiving wages, my slaves have money deposited into investment accounts for their benefit. I take care of all their expenses including room and board. They work as models, metallurgists, gemologists, sales people, etc. Adele is in charge of all my manufacturing, although most of it is contracted out, but the custom work is all hers. Monique manages my household. If anyone leaves my service, they receive the money from their investment account which in Adele's and Monique's cases, is in the millions, because they don't have to touch it."

"Interesting concept, Mistress Brianna," Dianne said. "How do you manage the taxes and social security?"

"It's paid on the equivalent of their anticipated salary benefit, although the salary goes into the accounts. Aren't you a polite little girl? So quick to catch on, or already well trained."

The flight attendant came back to ask them to fasten their seat belts. They were cleared to take off.

"Thanks, Ann," Chloe said, noting her name tag. "I'd like you and all the flight crew to know that Pet here, with the pussy tattoo and gold jewelry, is available to pleasure any women on the crew. Slut, without the tattoo or jewelry, may pleasure anyone, man or woman. If you have time, feel free to indulge. Please tell the flight crew. Obviously, this applies to you and your slaves, Brianna."

"Thank you, I'lll let them know," Ann said, preparing to buckle her own belt.

Everyone fastened their seat belts.

"Are they any good?" Brianna asked.

"Pet is a little bit better because she openly embraced sex with me. Slut was a gay and lesbian hater when I first met her, but she's changed her tune since then. She's improved rapidly."

"Monique is widely considered the best cunt licker on my estate. Feel free to partake of their services."

"Anyone do cocks," Chloe asked.

"We all have the capability of doing cocks. We've all had children in the old fashioned way, but very seldom does anyone do it and only select males I have confidence in. I have a couple bisexual slaves, but most of us are pretty much full blown lesbians."

"Dianne would probably be my top cock sucker too, but she can't have sex with any male but Matt. She is a profoundly sexy creature, though."

When they reached cruising altitude with clear skies expected, they were told they could release their seatbelts. Ann was providing them with fluids to counteract the dryness.

Matt, Dianne and Chloe told the others their story, then Chloe told them how she'd turned Rosilyn from a dyke shaming biased bitch to pussy loving slut. After hearing the story, both Adele and Monique made her lick their cunts. Rosilyn was not at all shy in doing so, as if in licking them she was making up for what she'd done. Brianna wished to try Dianne out instead. She'd pulled up her dress and let Dianne tug down her panties.

"How long as Dianne been a rug muncher?" Brianna moaned as Dianne pleasured her.

"A little after mid-April," Chloe replied.

"So good so soon?"

"Yes. If she weren't so closely attached to Matt's dick, I'd have thought she was a closet lesbian, or at least lesbian leaning bi, but she's definitely a dick lover. To a certain extent, I attribute it to her submissiveness. She strives to be pleasing, therefore she is. I didn't imagine the treasure trove of submissiveness I unlocked in her. I never even expected it. She was curious after meeting Evelyn and I arranged a few hours of submission and she came to me four days later and begged to take my collar permanently."

"Why don't you try Monique and if you want, we can ensure they both get some lessons from her before we part ways. Oh, fuck, that's it sweetheart, lick my clit just like that. What a sweet pussy pleaser you are." Brianna stroked Dianne's hair, encouraging her with her praise.

After two orgasms for Brianna, Dianne relieved Matt and Monique licked Chloe. Brianna warned her she'd be punished if she did any less but her absolute best.

"Yes, Mistress," Monique replied before pulling down Chloe's shorts and panties and diving in. Within twenty seconds Chloe was moaning.

"Oh, you're right. Monique is super good."

"I've never met anyone who loves licking pussy as much as she does. I swear she could live off it. I've met some others who are almost as good, including the father of my children, but Monique is still the champ."

Dianne later took care of the flight attendant and Rosilyn was sent up to the cockpit to take care of both pilot and co-pilot, one male, one female. The flight attendant gave the slaves some lemon scented wet naps to wipe their faces later. Until they needed to belt up, the two slaves sat in Matt and Chloe's laps and received their reward for being pleasing, Matt caressing Dianne and Chloe taking care of Rosilyn. All the slaves dressed before departing the plane.

There was a helicopter waiting for them when they landed at a small regional field on Long Island which whisked them to a landing pad atop a gray stone mansion on the upper west side opposite Central Park. They took an elevator down into the building where William and Evelyn greeted them. Evelyn was naked and given that she was, Dianne and Rosilyn immediately stripped again.

Rosilyn was the only one who hadn't met William and Evelyn before, so she was introduced. Rosilyn realized she was standing naked in front of one of the richest men in the world. Even stranger was his wife was doing the same. She suddenly realized who Ethel had to be.

"You're re-related to Et-Ethel, aren't you?" Rosilyn stammered.

Chloe smacked Rosily on her bare ass. "Master William. You will address him properly, slave. If you haven't already figured it out, you'll address Brianna as Mistress."

"I'm sorry, M-Master William."

"Ethel is my elder sister. We grew up in Wisconsin. She chose to return when she graduated from college."

"I never connected the name, Master."

"Might be one of the reasons she moved back. Didn't have to worry about people connecting her to me."

"Is Delphine still here, Master?" Dianne asked.

"She's still here, giving Madeline a bath before supper. She'll be dining with us. Chloe told me that you got the urge to try out submission after our visit, and upon trying it, decided to become a full time submissive."

"Yes, sir."

"Out of curiosity, why did you choose Chloe as a Mistress instead of Matt as your Master?"

"While Matt is a wonderful man and I hope, my future husband, Master, I did not think he could be as Dominant as Chloe is. Matt would be too kind and unwilling to push me as a submissive."

"In what way has she pushed you?"

"When she arranged for my test of submission, she did things Matt couldn't have done, sir, and not only did she get me to do them, she arranged for the participation of other people Matt couldn't have gotten to participate. It was very intense. Since we were in a polyamorous relationship anyway, I decided Chloe should be my Mistress as long as she protected Matt's rights as my boyfriend. I've had sex with your sister and his family, because Mistress pushes me in ways Matt never could."