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My maid instructs me on masturbation and regular spankings.
From her perspective at least!
She'd actually managed to take around eight inches, not at all a bad effort. I knew she had some significant experience with cocks in her mouth! I was confident that given the chance, we could get the whole thing down her gullet. I was certainly looking forward to practicing.
I bent down and gently turned her head to the side. I planted a gentle kiss on her cheek.
"That was a very good effort baby. Maybe next time you'll get it all, but for now, I guess I have to put it somewhere else that's warm!" I said softly, but with a very evil overtone.
"NO! OH GOD, NO! PLEASE SCOTT! You'll tear me apart, you know you will!" she shrieked.
In my most soothing voice I said, "Not if you cooperate. I'm going to do this, but if you behave, you'll be able to stand it. Oh, it will hurt like Hell, but you'll get through it if you do what I tell you!"
Evidently resigned she said, "Okay, what do I do?"
"Just listen and do what I tell you!" I said firmly.
Since I hadn't, and wasn't going to, give her a safe word, I'd have to be careful. After all, I enjoy feeling the fear and pain of the woman. I'm definitely sadistic at times, but I'm not an animal, or worse a rapist!
She'd have a safe word, without knowing it. It would be up to me to tell if she'd used it.
"First" I said unkindly, "I'm going to help you by giving you something to distract you from the pain"
And with that I went to the table and retrieved the nipple clamps I'd left there. They weren't particularly nasty, but they would be quite effective, especially when she moved, once I'd attached the weights on springs. I attached the clamps and then quickly hung the weights.
"FUCK! Oh GOD those hurt!" she roared.
"Shh! You'll get use to them soon. And they will help, believe me. Now remember! LISTEN and do what I tell you!" I commanded.
There was NO WAY this wouldn't hurt like Hell, especially given that it was her first time. I hoped that the fear would do what it was intended to do. I also hoped that the eroticism would come through for her too! It was time to find out.
I moved behind her for real this time, and began to play with her pussy. I worked a couple of fingers in and out being sure to apply pressure to her clit as well. I found her G spot again and kept rubbing right over it. She was starting to squirm and moan with delight.
I kept it up until she was flooding my hand with her cunt juice. Without stopping, I grasped the base of the plug with the other.
"Take a deep breath. Let it out, and relax as much as you can!" I instructed.
She did exactly as I'd told her. That was a good sign. I smoothly and quickly extracted the plug.
"Oh shit!" she moaned.
I reached over and poured a large amount of lube on the fingers of my right hand and started to work two into her asshole before it had completely tighten up after the removal of the plug. My left hand went back to her cunt.
I was getting her thoroughly worked up as well as assuring her ass was well lubricated. If this was going to have any chance of working I couldn't under do the amount of lube in her ass.
It was time. I poured lube on my cock until it was dripping off onto the floor then placed the head against her opening. I felt her tense again.
"Now, RELAX! We can do this baby. I promise I'll go real slow, as long as you do what I tell you. Take deep breaths. Pant if it gets real hard, but not for too long or you'll get light headed" I said, wanting her to get through this.
She groaned again but said nothing. She nodded yes and I began to push. There was no point in going too slow until I at least had the entire head inside her. I kept up the pressure and watched the rather erotic sight of her asshole stretching around my cock head. It took a while but soon the thickest part of the head reached her anus and the skin enveloped the whole thing.
"Ow, oh OW!" she cried and started to pant like I'd told her.
I stopped and stroked her ass gently.
"You're doing real good sweetheart, just stay relaxed," I said softly.
She stopped panting af