Anal training with Stacy

“Now we need to talk about your virgin asshole don’t we, that just wont do here." Mr Donovan pinches my hard nipples as he says that, making me shiver. “Go find Stacy from accounts, she can teach you all about training your asshole.” He smiles widely. “Then come back and show me your progress.”

As I turn to go he adds, “Oh and during Stacy back with you!”

I walk out, only wearing a skirt and my heels now, top completely abandonded. I look around the office, before I find accounting, and a sandy haired girl sitting at her desk. "Stacy? Hi, I'm the new assistant Ashley, Mr Donovan said you could do some anal training with me?"

As I say Mr Donovan's name Stacy winces. Was that pain…no did-did she just cum?!

Pretending like nothing happened, she smiles up at me. “You must be new, have you ever tried anything like this before?” She asks with a caring tone as she turns and fiddles with the lock on the cabinet behind her.

"I havent, I dont do anal with my partners. But if it's for my job, I'm happy to learn!"

As she unlocks the cabinet, I see a small trickle of liquid run down her thigh and realise something did indeed make her cum.

She pulls open the cabinet doors and in front of me is a collection of all kinds of sex toys. There's buttplugs, dildos in all shapes and colours, one must be at least 14 inches!

“Now we probably want to start you off with something small to get you started…did he say any particular training?”

"He specified anal, have you got anything for that?"

Stacy pulls out a drawer, then turns and hands me a small butt plug, a bottle of lube, a slightly larger butt plug, and then picks up a plug so large it makes me nervous.

“Oh don’t worry princess this isn’t for you” she giggles.

“We can use the meeting room if you’d like a little privacy away from all these prying eyes.”

She loops my arm and walks to the meeting room, closing the door behind us.

We enter the meeting room, its glass darkened. I turn on the light, and see Stacy already bent over, pulling down her panties. I watch in amazement as I see the shimmering object in her ass, and she pulls a full 7 inch dildo out! She moans as each bit comes out, then gasps when it all comes out with a *pop*. She turns to me, a satisfied look on her face, and then puts the dildo in my mouth! I swallow the dildo, licking her juices off it with gusto. She smiles at my eagerness.

She giggles “Oh you'll do amazing here! But don’t get too carried away with it, we’ve got lessons to learn. Now skirt up and bend over the desk, there’s a good girl.”

Stacy gets some lube and pours it onto the smallest plug, getting it slick.

“Now you can use spit or your pussy juices, but for the first time we will use lube…spread your asscheeks babe.”

I feel her kneel down behind me and squirt some of the lube into my asshole. “You’ve got a cute pussy! Has he used it yet?”

"Thanks! He hasnt used my pussy yet no." I jump a little at the sensation of lube in my ass, and then jerk as Stacy slowly inserts the buttplug. "There you go sweetheart, just squeeze on it, just like that." I moan at the sensation, shaking at the new pleasure. I could never have imagined it would feel like this, like a tight pain, mixed with so much pleasure! It makes my knees buckle as it is slowly pushed deeper and deeper. Finally its all the way in, and Stacy stands back to admire her work. "A perfect fit, it's like your asshole was designed for this!" She gives my ass a smack, and I squeal. I turn back around to her, legs shaking slightly, trying to keep a professional composure. "Thank you very much Stacy, I'm sure Mr Donovan will be very pleased!"

“Urghf-fuuuck!” You see Stacy's knees shake as she clutches at her crotch as I say Mr Donovans name, she’s cumming again, juices dripping down her thighs.