The Nanny Ch. 05

His blush confirmed that he did indeed.

"Still, it might need a little lubrication" – and I reached down to my pussy, rubbing the ball of the anal plug up and down my slit, before plunging it in and out of my hole a few times.

"What a coincidence! Your cock appears to be ready now." I handed the well-lubricated toy to him, and watched as he worked the ring over his erection. When the ring was seated firmly at the base of his cock, he paused.

"What are you waiting for, slave? What have I told you about hesitation?"

"Sorry, Mistress, I-I was unsure how to insert it."

Another theatrical sigh, from me, as I unclipped my riding crop. "Do I have to teach you everthing?"

"Yes, please, Nanny."

I suspected I'd seen the beginning of a smirk as he answered, but he wiped it off his face before I could be sure. I stepped behind him, and gave him a good smack across both buttocks, anyway.

"Kneel! Spread your legs! Now, reach behind you and take hold of the plug. Insert."

He grimaced as the plug spread his virgin asshole, then gasped as it popped into place.

I spanked him again: "What do you say?"

"Thank you for instructing me, Nanny."

"That's better. Now, put your hands behind your head, again. Whenever I tell you to kneel, this is the position you will take. Now, recite your catechism."

"Christie is my mistress,

"I will obey my mistress in all things, without hesitation,

"I will at all times be respectful,

"I will come only when, and where my mistress permits,

"My mistress will teach me my duties, and discipline my transgressions.

"My mistress will protect me, as I will serve her."

"Almost. You 'will come only when...'?"

"...when, where and with whom, my mistress permits!"

"Better. Now repeat it."

This time he got it right.

"Very good." I pulled one more item from my pack, and fastened the collar snugly round his neck, then clipped his wrist cuffs to the back of the collar.

I walked around to place myself in front of him again, placed my hand on his head. "I claim you to my service. Kiss me!" I guided his face down to my pussy and, getting the hint, he spread my nether lips with his tongue, then sucked my clit gently between his lips.

"Good boy. Hold that pose, I'll be right back."

I took my time, going upstairs to lower the ends of the tie-down again, then using the bathroom. Coming down the stairs, again, I noticed he was already learning to use the cock ring. He would twitch slightly, applying tension to the leash between the ring and the butt-plug, and when he relaxed again, his cock was a little stiffer. God! He was getting himself off, even without touching himself!

When I returned, I ordered him to stand – and when his leg cramped and he stumbled I gave him another stroke for "hesitation". I ordered him to stand in front of the kitchen counter, where I released his wrists from his collar, and clipped them to the tie-down. Then I pulled the free end tight, stretching his arms both out and up, and making him rise slightly on his toes to relieve the pressure on his shoulders.

"Thank you, Nanny."

"You're welcome, pet. We have to deal with a few issues with your training, don't we."

"Yes, Mistress."

"Why don't you tell me what those are?" From behind, I stroked the riding crop down his cheek, then down his back to the cleft of his butt, finally stroking his balls with the tip.

"I was late arriving to our ap-p-pointment, Nanny ... I-I was not in the position you ordered... And ...", he blushed, and whispered "and my cock was not hard, Nanny."

"Three violations, pet? Is that all?"

"I did not have my catechism memorized, Nanny."

"Anything else?"

"No, Nanny!"

"What were you doing when I was upstairs?"

"Waiting for you, Nanny!"

"I saw you." Thwack! "You were using the plug to jerk yourself off!" Thwack!

"No, Nanny!"

"Never lie to me, pet." I gave him another stroke across both buns.

"Yes, Nanny! I was."

"That's better, boy. But I will still have to punish you."

"Thank you, Nanny."

"I think though, that you might be perhaps a little loud, so we have one more toy for you." I went back to my pack and brought out the ball gag. I made sure he got a good look at it.

"Open wide, pet." He obeyed immediately, and I fit the gag in his mouth and fastened it behind his head. "Now, I think ten strokes would be appropriate, don't you?" He nodded enthusiastically – knowing that if he disagreed, I'd pretend he wanted more.

I had to be careful, now. I was brand new to this and didn't know how much he could take. I'd already given him more strokes than yesterday, and I was proposing ten more. Nothing to do but get on with the job. I lashed him across his stretched shoulders.

"One." I hadn't even raised a welt – he could certainly take more than this.

"Two." This one lower, and harder. He stretched onto his toes. That worked better. A faint red line showed.

"Three... Four... Five." He was groaning, now.

"Six... Seven... Eight." More groaning. With a start, I realized it was me, now.

His back was a criss-crossing of red lines, but nothing looked too deep, and I hadn't drawn blood. I couldn't wait. I gave him one more half-hearted stroke on each butt-cheek, then reached up to release the ratchet holding him in place. I was shaking so hard that it took me three tries, but as it released, he collapsed to his knees. I struggled to get him unclipped, then helped him to his feet.

"Come on! I need you now!" I grabbed him by his cock and pulled him towards the stairs. He staggered but followed willingly. In the bedroom, I turned to kiss him, and realized he was still wearing the ball gag.

"Oops!" I fumbled at the strap and finally got it off. "Now, fuck me – and you know I want it hard!"

He spun me round, pushed me face first onto the bed, and plunged his cock straight into my cunt.

"Oh, YES!!!!!!!!!"

"Oh, Nanny, you're so hot and tight!" We were both way beyond subtlety now, and I could feel his balls slap my clit on every stroke, each one harder than the last.

"Nanny, I can't hold on much longer, I'm going to come."

"Do it, pet, come in me noooooowwww!" An explosion rocked my cunt, rolling up my entire body.

"Aaaahhhhhhh!!!!" John came with me, and as I felt his cum filling me, I came again, almost as strongly as before. John kept pumping until his cock was empty, then pulled out of me, rolled me over, and promptly dropped to his knees at the side of the bed, placing his mouth over my pussy lips, and licking and sucking me clean.

"Thank you – John." It was the first time I'd used his name since he arrived.

"Thank you, Nanny!"

I rolled off the bed and looked at him. The cock ring had kept him stiff.

"Oh, that's beautiful. Now, I owe you a reward. Would you like to fuck my ass?"

"Nanny! May I, really?"

"Yes, pet. Be careful, though, I've never had a cock there." It didn't seem necessary to mention that I had been using a vibrator there for months, fantasizing that it was his tool.

Again, he bent me over the side of the bed, and reached between my legs to moisten his fingers with my juices, then began to massage my ass, working my own cum into the crack of my ass, and then gently into my asshole. As he worked, he frequently reached forward to lube his fingers from my pussy, which was working overtime to provide him what he needed. He slipped one finger into my ass, worked it, then a second. As he stretched my hole, I relaxed, and felt him probing deeper. He leaned over and murmured into my ear.

"Ready, Nanny."

"Yes, pet. Do it, now, please."

He stuffed his rod up my pussy, just once, then pulled out, positioning himself at my darker gate. I felt a momentary pressure on my bud, then the head had slipped inside.

"Oh!"

"Is it alright, Nanny?" he asked, with obvious concern.

"It's fine, pet – I was expecting it to be more painful. You're very talented – gentle when I need you to be, and .... ooooohhhhhhhhhhhhh!" His shaft was slowly, inexorably, ploughing my (technically) virgin ass, and it felt wonderful. An inch at a time, he eased his shaft deeper into my bowels, filling me in a way I'd never been filled before.

"Ohmigod, that feels good.

"More...!"

John's cock isn't huge, but it is certainly bigger than my vibrator, and I can't work the vibrator in my own ass the way he can work his cock. His cock finally bottomed out, and I felt his pubes against my buns. Then he started to stroke, pulling out slowly until I felt his glans once again pulling on my anal ring, then pumping back in."

"Faster...!"

He really didn't need to be told – every stroke was just a little faster than the last.

"HARDER!"

This was the fourth time he'd fucked me, and by now I guess he knew the routine – mouth, cunt or ass, when I told him to fuck me, I wanted it hard, and after the abuse I'd given him, he was more than prepared to return the favor. By this point, every time he bottomed out, MY bottom was lifted off the bed, and my thighs were being bruised where they rested against the bed frame. As I started to come, he reached his right hand around, thrust it in the cup of my bustier, and squeezed my tit hard. The pain sent me over the top, and I had my first screaming orgasm.

"Aaaaaaaaaahhhhhh! You BAAASSSTAAARD!"

He released the tit, only to concentrate more force on the nipple itself. Twisting it hard made me come again.

"Aaaiiiiiiieeeeeeeeee!" I screamed.

That was enough for John, and I felt him start to pump his jazz into my ass. It seemed to go on forever, and when I felt the cum leaking around his cock, and down my slit, I came once more.

"Oooooooohhhhhhhhhh ... God...," I sighed and collapsed as a series of smaller tremors continued to shake me.

As his iron rod turned into a limp noodle, he gently withdrew, with a slight 'pop', then knelt, spreading my ass-cheeks with his hands to lick my asshole clean. When my butt and thighs were clean of his cum, he rolled me over to clean my pussy again.

"Good boy. Now go into the bathroom and remove the plug and cock-ring – it's not safe to wear a ring too long. Clean it off and find somewhere to keep it – you'll be needing it again tomorrow. When you're done, we'll talk about your homework."

When he returned, I told him what I wanted from him.

"First, tomorrow I expect to see you here at the same time. You will be wearing your collar, cuffs and cock-ring, and kneeling in the same place. I have one more toy downstairs – a blindfold. You'll be wearing that, too. We're going to deal with the issue of your marital infidelity. I think we'll have a lot of fun, pet.

"Now, for tonight's homework. I don't know when you expect Cathy to get home, but make sure you're home before her. As soon as she gets in the house, you will get her into your bedroom – do whatever it takes – and you will fuck her. I don't care if she resists – I don't care if she absolutely refuses. Do whatever it takes!"

"B-b-but N-nanny! She's my wife!"

"Are you going to disobey me, boy?"

He hung his head, obviously in agony, but muttered: "No, Nanny... I will obey."

"Good boy. If you do as you're told, you can come to my room again, tonight, after she's asleep.

"Now, unlace me – it was a bitch trying to get this bustier on, and I'll be damned if I'm going to unfasten it by myself when I've got help. I'm going to change, and go home. You shower and clean up in here, and I'll see you later."