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Chapter 408
by
JohnFlow
What's next?
The final addition
"Now come here so I can give you the final addition." You instruct.
Sofia does as you say, walking around your desk to you. You reach into one of your desk drawers and pull out a small silver buttplug. Sofia's eyes shoot open wide whens he sees it. Even though she would have read about it in your contract, she seems to have forgotten about it up until now.
"Don't worry, we'll be starting you with a small one and working your way up. Tell me, have you ever tried anal before?" You ask.
"My husband and I tried it once but it was too uncomfortable so we never did it again." She says, not taking her eyes off the plug for even a second.
"I see, definitely best we start small then and work our way up." You add.
"That's a small one?" Sofia asks nervously.
"Oh yeah, we should see the one I've got in Diane, that thing's huge. If you see her today you should ask to take a look, I'm sure she'd be happy to show you. Anyway, this week you'll slowly work your way up with the plugs and then by the end of the week I'll try out your asshole myself. Turn around and let me get this thing inside you." You say.
Sofia anxiously does as you say, turning around and hiking up her skirt to reveal her big round ass.
"Why don't you lube it up a little first." You say, stepping around to her front and inserting the plug into her mouth.
Sofia sucks it as she would a cock, trying her best to get it as wet as possible to help herself out. Once you're satisfied you take it out of her mouth and step around back once again. Once there, you push the plug into her hole. Sofia quickly tenses up, causing her sphincter to tighten and preventing the plug from penetrating her back door.
"Relax, it won't feel uncomfortable once you get used to it." You say.
Sofia does her best to relax, allowing you to get the plug inside. With a satisfying *pop*, the whole thing is inside, with the only part showing being a circular jewel sitting pretty right between her pink, spanked ass cheeks. It's a snug fit, but mostly due to the fact she's pretty much an anal virgin and how tense she is. Once she learns to relax and loosen up she should be able to work her way up in sizes.

"Good job, it's in." You say.
Sofia takes a deep breath out and you can immediately see her asshole relax. You also notice how wet her pussy has gotten, with some of it even dripping down her thigh a little. You rub your finger along her slit causing her to shudder a little and then step around to her front.
"My my, look how wet you've gotten. Seems someone enjoys a good spanking." You say, showing her your finger covered in her juices.
"I... That's not..." She stutters, embarrassed.
"It's ok, you don't have to be ashamed of it. We're very accepting here in this company. Now clean this up for me will you." You say, sticking your finger in her mouth for her to suck her own juices off of.
She begrudgingly does as you intend and sucks your finger clean. You then step back around behind her.
"Let me just add one thing, trust me, it's for your own good." You say.
You grab a black sharpie and use it to write on her lower back, just above her ass. In big block letters, you write 'ASSHOLE - COMING SOON'.
"There you go, that way none of the guys will try using your back door before you're ready. Just make sure to wash that off before you head home to your husband I suppose." You say.
Sofia awkwardly twists around to try and see what exactly you've written on her back but to no avail.
"You're good to go then." You say, giving Sofia a smack on the ass, causing her to jump due to her sensitive cheeks thanks to her earlier punishment.
"Thank you sir." She says, begrudgingly.
"Not a problem, Meg will escort you and get you set up in your new office." You say.
"My new office?" She asks.
"Of course, new position, new office." You say.
With that Sofia exits your office, skimpy outfit on and plug in her ass.
What's next?
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Slut Girlfriend
Discovering your girlfriend's kink for being controlled and taking lots of dick
A story in which your submissive nymphomaniac girlfriend gives you control of her holes, to fuck yourself and lend out to whomever you please. One thing's for sure, she's going to be getting pounded
Updated on Jun 16, 2026
by JohnFlow
Created on Sep 14, 2021
by JohnFlow
You can customize this story. Simply enter the following details about the main characters.
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