Chapter 21
Twenty-One
Rook
Somehow, I manage to wait three days before I go to my girl. Well, that’s not entirely true. I go to her room every night to leave instructions and lay out her clothes. I just don’t wake her.
I’m surprised she doesn’t defy me and stay awake all night at some point. I half expect her to be sitting at her desk without the mask on, waiting, watching, hoping to catch me.
But I know she doesn’t because I’m watching her every move. She goes to bed like a good girl when I tell her to, and I always wait until she’s sound asleep before I step into her room.
What I hate is that I’ve never been able to watch her clean out her bottom.
I know she does it because she keeps the douche kit in the bottom of the desk drawer and takes it out every night.
She also spends more time in the bathroom before bed than she used to.
It makes my cock hard, knowing what she’s doing. I want to fucking watch, though.
Tonight is the perfect night to go to her because her roommates are all out again. I feel far less nervous about someone hearing us when they aren’t home. It also helps that I can monitor their whereabouts on my GPS tracker, so I’ll know if any of them return early.
It’s late when I enter. My girl is sound asleep, her breathing deep and even, assuring me of the fact.
This is the fourth night in a row that she’s obediently gone to bed draped over her pillows with her bottom in the air.
I know she’s naked under the covers. It’s impressive that she manages to sleep like this every night.
She won’t have to do it again. Tonight, I will put her out of her misery.
For long minutes, I simply stare at her. I’ve turned the bathroom light on, so I can see her well from the glow. She’s so stunning. She takes my breath away every time I see her.
I keep thinking, one of these days, I will flush her out of my system, tire of her, no longer walk into her room and find her so intriguing. But it hasn’t happened, and I’m resigned to the fact that it may never.
Tonight, I don’t cover her mouth. If she cries out in surprise, there’s no one home to hear her. I suspect she will not, though. She’s trained to keep her voice very low. I doubt she would make much of a peep even if I dropped an anvil on her leg and broke it.
That’s pretty morbid. I’m not sure where that thought came from.
I would never hurt her. Not like that. I do enjoy inflicting pain on her, but only the kind of pain she needs in order to learn to obey me. I wouldn’t injure her for no reason.
I struck her pretty hard the last time I was here.
I surprised even myself. I wasn’t out of control or anything.
The entire time, I was calm. I’d been prepared for the possibility that she might balk and refuse to let me touch her bottom.
I’d even kind of hoped it would go down that way so I could use the episode as another lesson.
It worked. She’s been punished enough between my belt and my absence.
Before waking Briana, I set my bag at the foot of the bed over the covers between her parted feet. I open it and pull out the supplies I’ll need.
She will submit to me tonight. She won’t like it, but she needs this. She needs to know that no part of her body is off-limits to Daddy. It never will be. I decide every detail of her life. That includes when she needs her bottom penetrated. It’s happening tonight.
I intend to be clinical about it. I won’t go easy on her. It will hurt. She will endure it for me.
Finally, I snap on my gloves. They aren’t entirely necessary, but the last time I put them on, she reacted violently. The gloves will help her feel like she’s being violated by a medical professional instead of her Daddy.
The sound of the rubber popping against my wrist yanks her out of sleep. I’m not touching her, but she’s instantly alert.
She lifts her head. “Daddy?” she whispers.
“Right next to you, princess.”
She smiles. “I missed you.”
“I missed you, too, pretty girl. So much. It disappoints me when you misbehave and force me to punish you.”
Her lips tremble. “I’m sorry, Daddy. I’ll do better.”
“I saw your text, princess. I think you need to apologize to Daddy out loud, though.”
She nods. “I’m so sorry, Daddy. I overreacted. I want to be your good girl.”
“You understand that your body is fragile, right?”
“Yes, Daddy.” She lowers her cheek back to the pillow. I’m sure it’s a strain to hold her head up.
“I never want to injure you, princess.”
“Thank you, Daddy.”
“Sometimes, that will mean that I need to help prepare you for the future. Do you understand?”
“Yes, Daddy.”
“Do you like the rubber cock I bought you to help you learn to take Daddy in your mouth?”
“Yes, Sir,” she whispers. She’s embarrassed.
“Have you been taking it deeper every night and marking it for me?”
“Yes, Daddy.”
“You wouldn’t want Daddy to fuck your pretty mouth without preparing you, would you?”
“No, Sir.”
“The cock will help you grow used to taking my thick dick as far back as possible. When I fuck your mouth, you’ll take me all the way into your throat. That means you need to learn how to open the back of your mouth and then swallow my come like a good girl.”
“Yes, Daddy.” Her voice is wobbly. I’m being so crude. And she’s fucking squirming.
“Have you been cleaning out your bottom every night before bed, princess?”
Her breath hitches before she whispers, “Yes, Daddy.”
“Good girl. It’s not a lot to ask, is it?”
“No, Sir,” she murmurs.
“Keeping your asshole clean will avoid you panicking when Daddy wants to finger, lick, or fuck your tight bottom”
She whimpers adorably, squirming.
I finally set one rubber-gloved finger on her throat and stroke the tender skin. “Good girls take their Daddies in their mouths, their cunts, and their tight assholes.”
She swallows hard and murmurs, “Yes, Sir.”
“I’m going to check your dildo and see how much progress you’ve made with your mouth.
I’ll make a mark to show you how much farther you need to reach.
I expect you to practice every day. If you need more than ten minutes, let me know.
I can also have you put me on a video call so I can instruct you if you’re having trouble.
You must learn to breathe through your nose and not gag when my dick is in your mouth.
You’ll need to be able to do so for long periods of time. ”
“Okay, Daddy. I can do it.”
“I know you can, princess. It just takes practice.”
I move my hand and pull the covers down, loving the way she squirms when I expose her. There’s an innocence about her that might never go away, and I’m okay with that. It’s precious.
“Tonight is not about your mouth, though, is it, Briana?”
“No, Sir.”
“What do you need from Daddy tonight, pretty girl?”
She shudders before she answers me. “I need you to train my tight hole.”
“That’s right. Do you understand now how important that is?”
“Yes, Daddy.”
“I suspect you’ve done some research, haven’t you?”
“Yes, Sir.”
“You wondered if people really have anal sex, didn’t you?” I’m so glad I have remote access to her computer. I can see everything she Googles.
“Yes, Daddy.”
“Does it matter who else gets their tight ass regularly fucked, though, princess?”
“No, Sir,” she whimpers.
“Because the only people who matter in our relationship are you and me. All that matters is that I’m going to fuck your pretty rosebud often, and I don’t want to tear your tender skin when I do so.”
“Yes, Daddy. Thank you, Daddy.”
“I’m not saying it won’t hurt. Training your bottom will be uncomfortable.
Sometimes, it might even be painful. Taking your ass with my cock might also cause you to wince from time to time, but the best way to avoid that is to consistently train your tight hole so you’re always prepared to take my thick length. ”
“Yes, Daddy.” She’s being so brave. I know she’s panicking, but she’s not running. She’s talked herself into this.
I’ve convinced her it’s necessary and very kind of me.
To be honest, it would be better if everyone prepared their partner before fucking them in the ass, but what’s different about my relationship with Briana is that I’m not giving her a choice.
She will open her ass for me because I demand it.
And she will learn to enjoy it because I intend to make that her reality.
Eventually, the nerve endings in her bottom will clench and her pussy will pulse simply at the suggestion that I’m going to fuck her ass.
I may be a sadist, and I’m going to fuck with her head every step of the way, but in the end, she will experience a new kind of euphoria when my dick is buried balls deep inside her ass.
Hell, even if for some reason she never enjoys anal penetration, she will still get off on pleasing me. If it hurts or if it’s embarrassing, she will still derive satisfaction from her obedience.
I’m drawing this out, making her tremble. She’s doubting her decision, as though she had a choice in this at any point.
“Spread your knees wider, princess.” I help her by folding a pillow and tucking it between her thighs, forcing them to remain open. I want her pussy to drip while I work on her ass. I’m going to make sure of it. My cock is already all kinds of hard at the idea.
I set my hands on her hips. “Bring your ass back a bit farther, pretty girl. I want your bottom higher. Keep your breasts pressed to the mattress.”
The whimper she emits makes me so happy. The position she’s in is so demeaning, yet she’s obeying me.
“Good girl. Now reach back and pull your cheeks apart. I want you to hold yourself open for me while I train your asshole.”
She’s shaking so hard as she does what she’s told that it’s a wonder she’s even capable.
I grab the lamp I brought and unfold the long arm of it, angling it toward her bottom before turning it on. The sound of the switch echoes loudly in the room. “It’s just a lamp, princess. Daddy wants a bright light shining on your rosebud while I stretch your tight fuckhole.”
I squirt some lube on my fingers before rubbing it onto her puckered hole.
It’s time to breach my girl.