Parts one and two are here:
I turned her back over, her ass high up in the air. As predicted, the red imprints of my hand were now visible all over it. Beautiful. As she writhed face down on the desk, desperate for my touch, I opened a drawer in my desk and pulled out a bottle of lube and the butt plug that I was going to use to train her ass.
The plug was tapered, a couple of inches thick at its widest point and around 5 inches long. It was going to be a lot wider than the span of my two fingers and, whilst I enjoyed her discomfort, I wanted to ease her into this, so to speak.
I coated my fingers with a generous amount of the lube and first smeared it around her asshole, where it combined with the spit that still glistened there. She pushed her ass up to meet my fingers, grinding against them, craving the contact. I enjoyed watching this for a minute or so, then pushed my fingers back deep inside her. She cried out at the sudden force, but then started pushing her ass against my fingers, writhing and moaning as she did so.
She turned her pretty face back to watch me and I nodded my approval, “Good girl, Carrie, you’re being such a good girl.” She smiled shyly, then closed her eyes, concentrating on the sensations in her newly-penetrated ass.
I squirted more lube from the bottle onto my fingers as they thrust in and out, the squelching sounds making my already straining cock even harder. Watching her delectable ass gyrate under my touch was an incredible sight. Perfectly framed by her garter belt and stockings, I allowed myself a moment to imagine how my cock was going to feel busting her anal cherry. Perfection!
I removed my fingers, squeezed more lube all over the plug and, with one hand on the small of Carrie’s back, pushed the head of the plug into her puckered, eager hole. She reared up when she felt it go in. “Sir! It’s too big Sir!”. My hand at her back prevented her from escaping and I kept pushing the plug in as she struggled against me.
“It’s a lot smaller than my cock, babydoll. This is to get you ready for me so that I can take your ass soon. You want my cock in your ass, don’t you?”
She submitted to me and stopped trying to resist. With fast little breaths she said “Yes Sir. Yes please, I want you to take my ass please Sir.”
“Good girl.” I moved the hand from the small of her back to slowly caress her smooth, reddened butt cheek, trailing down and stroking her hard little clit as her soaking pussy ground against the palm of my hand. “So you’re going to need to take this plug for me and then I’m going to make you cum with my mouth. Do you understand, Carrie?”
“Yes Sir.’
“Ask me for the plug, Carrie. Beg me to push it inside you.”
She took a deep breath, then - a little shakily - said, “Please Sir, please stretch me out with the plug. I want my tight little hole ready for your cock Sir, so you can claim my ass.”
What a girl! What an ass!
I wiggled the plug up and into her, still rubbing lightly against her clit with each push. She resumed pushing back onto me, her enthusiasm helping the plug to finally find its target all the way inside her. The last two inches of the neck were much thinner and slid right in, almost sucked in by her grinding little motions. Now only the flat narrow base was visible; it would anchor the plug inside her until I permitted her to remove it later today. It would then be replaced with a larger one overnight. This ass was going to be mine tomorrow; I couldn’t stand to wait any longer.
There was still a whole lot of her to enjoy today, however. With a quick glance at my watch, I realised I had another twenty minutes before my first meeting of the day. No time to waste…
I gave her ass a little slap. She yelped, tightening up and then cried out in surprise at the sensation of the plug against her sphincter as her muscles clenched around it. “You like that, Carrie?”
“Yes Sir. It feels so strange. But in a good way.”
Sitting down and wheeling my chair back into position, I said, “Flip over for me and spread those legs back out on the arms of the chair. I’m going to make you cum all over my tongue, then I’ll fuck you until you scream and then I’m going to dump every drop of cum in my balls so fucking deep inside you whilst you beg me never to stop. You good with that?”
“Oh yes Sir. Oh please, yes.”
I laughed out loud again at how quickly she rearranged herself, following my instructions with her usual efficiency, balancing her heels on the edges of the chair’s armrests.
Grabbing her ass cheeks, I used the leverage to wheel myself all the way to her spread pussy. It really was the most perfect pink little cunt I’d ever seen, and so fucking wet for me.
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