Nina's Nightmare Holiday
This story is in the public domain.
Chapter 35
Sex Story: Chapter 35 - Nina is a gorgeous, powerful businesswoman. Her self-confidence gets her into trouble when a young boy she meets on vacation in a luxury hotel starts blackmailing her. Can she outwit him and regain her dignity or will he be her master for life? CAUTION: extremely sadistic, only for those who enjoy this type of fantasy.
Caution: This Sex Story contains strong sexual content, including Ma/Fa mt/ft Ma/ft mt/Fa Fa/Fa Fa/ft Blackmail Coercion Drunk/Drugged NonConsensual Rape Slavery Lesbian BiSexual Heterosexual Fiction Celebrity Incest Mother Son Brother Sister Father Daughter BDSM DomSub MaleDom Humiliation Rough Sadistic Spanking Torture Gang Bang Group Sex Harem Anal Sex Bestiality Cream Pie First Fisting Oral Sex Pregnancy Spitting Tit-Fucking Water Sports Body Modification Needles Caution ENF Violence
Nina, Jenny and Chrissy were all staring at Jeremy. He grinned.
“Let’s start by establishing the rules by which you will live here. Breaking any of these will result in harsh punishments. Do you understand?”
They nodded.
“You will not wear clothes inside this apartment unless told to. It doesn’t matter if other people come to visit. When you enter this apartment, you will always strip naked and then stay that way unless told otherwise. There are no exceptions. Got it?”
They nodded.
“The only thing you will wear here is these shoes. Put them on now.”
He placed three pairs of elegant black stilettos on the table. Each of them took one pair. Nina struggled to get off the chair without the dildo inside her causing more pain. She put the shoes on, then slowly led the dildo slide back into her. She couldn’t stop herself from noticing how slutty Jenny and Chrissy looked, naked and wearing only those shoes.
“You will wear these shoes at all times unless you’re in bed or taking a shower. Understood?”
They nodded.
“When you leave the house, you will only wear clothing I’ve previously approved. You are not allowed to wear any underwear except with specific permission. On most days I will allow you to wear a thong, if you’ve been good. You will not be allowed to wear a bra unless it has either cum or thumbtacks in it or unless you’ve been very good.”
Nina shuddered at the thought of either option. Jeremy placed three more objects on the table.
“You will wear these buttplugs at all times. You can take them off to go to the toilet, but they always have to go back in. They are connected to an app on your phones that will let me monitor them. Put them in now.”
Nina had to painfully lift herself off the chair dildo again. The buttplug was silver and mercifully small but it was still humiliating to have to go around in public with it inside her. She pressed it into herself with a wince. Then she slowly took the dildo back into her until it was pressing on her half-open cervix.
Jeremy tapped something on his phone. Suddenly Nina felt an intensely unpleasant vibration in her asshole. She and Jenny and Chrissy yelped at the same time.
“They’re also remote controlled.”
He turned them off again.
“Now let’s talk about your daily routines. Every morning when you wake up, you will each spend fifteen minutes riding the bedpost.”
“Every morning?” Nina gasped.
“Yes and you’ll take it deep. When you’re done with it, you’ll lick it clean. Then you’ll proceed to the bathroom, where you’ll find a glass with the label SLUTS. You will fill this with your piss. Then you’ll drink it.”
Chrissy made a disgusted face.
“Then you’re allowed to take a shower and brush your teeth. Before you leave the bathroom, you must take one nude selfie and send it to someone you know. Me, my dad, Nina’s dad, Big Al ... not the same person every day.”
Nina’s stomach lurched when she remembered her father.
“After that each of you will go on to the day’s tasks. Chrissy, you will attend dance academy in the morning and private lessons in the evening. There is a space for that on the floor above.”
“Private lessons?”
“We’ll get to that soon. Chrissy, if you want to attend lessons without weights on your nipples, you’re going to have to take photos. I want to see your class mates in the changing room.”
“But ... how...”
“You’ll figure out a way. Girls are sluts, after all. Regular photos will let you attend lessons in peace. Except for the buttplug and whatever I shove up your pussy when I feel like it.”
Chrissy looked scared.
“Every evening you will attend private lessons with Ms. Annie Dubose.”
Chrissy’s face went from scared to shocked.
“What? She’s literally one of the most famous dance teachers in New York! How is that possible?”
“Money, sis. Money. Ms. Dubose went through a very expensive divorce after her old school closed. She’s in so much debt it could destroy her life. Ms. Dubose, will you enter the room, please?”
A door opened somewhere and a woman came walking into the room. Nina felt so shocked at the thought of being seen like this that she immediately tried to hide her breasts. Chrissy did the same. Only Jenny remained as she was. She gestured to Nina.
“He’ll punish you,” she whispered.
Nina let her breasts show.
The woman who had walked in was strikingly beautiful and graceful. She was older, maybe in her late 50s or early 60s, but her body was tight and athletic. Her hair was gray but her thin face was gentle and very attractive. She was wearing a thin black dress that clung to her skin.
“Hello,” she said gently.
She looked at them with a strange expression, confused but empathetic. Chrissy had turned red with embarrassment.
“H-hi Ms. D-Dubose,” she stuttered.
“Hello, Chrissy,” the teacher said. “It’s nice to meet you, despite the ... circumstances.”
“Time to start living by the rules, Annie,” Jeremy said.
Ms. Dubose looked a little sad for a moment. Then she pulled her dress over her head, revealing her naked body underneath. Her breasts were small but firm for her age, with small nipples. Her pussy was trimmed to a thin gray-black landing strip. She looked beautiful but Nina felt ashamed to be looking at her.
Annie looked around a little uncomfortably.
“Sit down,” Jeremy instructed. He pulled up a chair with a long dildo on it.
“Oh my,” she said nervously.
“Yes, that’ll hurt. Unless Chrissy wants to help with lubrication?”
Chrissy stared at her brother, then at the beautiful woman she had admired for years.
“I’ll do it,” she whispered.
Chrissy lifted herself off the dildo on her own chair and bent over Annie’s chair to take the other dildo into her throat. But Jeremy stopped her.
“No, sis. Stick your tongue in her pussy.”
Chrissy looked at Annie helplessly. Nina could see that she didn’t want her first interaction with someone she admired so much to be this.