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A Length of a Good Time

Summary:

Lilly is a girl who has been in her line of work for a good couple years now. She served a special company for quite some time now and she wouldn't have it any other way. Follow the lilly as she is exposed to more of her life in "upper management".

Notes:

The reader is androgenously female. Any perspective shifts are merely keep an eye on the action. There will not be any specification of Lilly's genetalia so imagine what your heart desires! In other words if you don't like Anal, this is your final warning. But if you do like anal, you're in for a treat. Enjoy! ;)

Chapter 1: The Morning Shift

Summary:

Lilly has just arrived late on one of her days off work. She she enters she tries to have a little fun before the weekly appointment.

Notes:

c.w. anal(duh!), anal gaping, piss-play, piss-drinking

(See the end of the chapter for more notes.)

Chapter Text

"Ms. Fall" The secretary in front of me said into her desk phone. "Your assistant is here."

"Please send her into my office." A reply came through transceiver.

"Right away ma'am." She said nodding her head towards me before returning to her work.

I opened the great doors to my bosses office, closing them a gently as I could.

"Good morning Ms. Fall, I'm apologize for my being late." I said, hurriedly setting down my briefcase by the door.

I stood around 5 feet and 9 inches tall, with my skin composing of a light pale creme. I had a white blouse paired with a black skirt on along with my hair being up in french braids coming down my back.

"Please stand there." She said pointing to the center floor in front of her desk.

After I had finished setting my stuff down, I walked over to the indicated position and stood facing her.

Ms. Fall was a proper name for who say in front of me. She wore a Burgendy Grey suit with a dusty grey tie to match. She had fair skin with her neatly pulled back hair being a deep almond color. She also had Burgendy glasses and earrings to match. All in all what you'd expect from a proper business woman.

"I was wanting to follow up with yesterday's matter. Hopefully everything is going well for you?" She said looking down at her desk, indulged in the work she had currently laid out before her.

"It's not bothering you is it?" A quick gesture of eyeing and then moving at my torso elicited the desire for response.

I paused momentarily, shifting my legs slightly "It's a bit difficult to walk around with it, but I've been able to manage."

"That's good to hear. You are going to have to get used to it so that when the real thing comes, it won't cause any issues."

"Of course ma'am..." I paused momentarily seeing that her focus has returned to her work. My eyes trailed downwards towards the intricate patterns spiraling the floors as if to make the question any easier to bear. "Speaking of which. I was hoping we could practice with that a bit today before the appointment ma'am..." My last words being barely audible "uh, p-please..."

A brief silence, after only her writing being audible, was met with an end as to give pause for a moment of thought. After which she continued what she was working on.

"Well Lilly, I don't think it's entirely out of the question... But first, I still think you had best perform your morning duties. Then I might consider it, yes?"

"Yes ma'am. Thank you ma'am. I'll get right to it!" I said, before walking over to the small counter space by my office door populated with a black tea set, an assortment of teabags and a kettle for heating water.

"Did you want your usual today ma'am?" I asked as I turned the electric kettle on, already having been refilled with fresh water from the night before.

"The Grey Ichor would be nice yes." She said.

Her favorite cup of tea. I've poured it many times for her before. My hands deftly worked the instruments of tea leaf containers and scoops. Blending together a bitter yet refined blend for my mistress.

Once the kettle clicked off I then picked it up and delicately poured it into the teapot, filling it, before putting the kettle back down on it's stand.

With the set prepped, I gently picked up the tray and put it on an ornate cart, after which waking it over to beside her desk. I move the cart gently making sure to not move to fast, lest I accidently start the showing too early. Let alone spilling any tea.

(Damn...) I thought to myself. (I've been holding it all since last night and need to let it out now!)

I gaze down at the chinese as I begin to pour the hot water out of the teapot into one of the teacups. Im careful to keep myself steady as I pour, knowing full well she doesn't like it when I look antsy.

After I finished filling it I proceeded to pull up my skirt , and tug my panties aside as I brought my nether close to the teacup. A rush of relief begins to wash over me as I aptly release a paced trickle of gold from my bladder, and let it fall into the tea.

I'm careful to release only a little, contracting my muscles once finished, to conserve more for next time. The sparkling stream coming out of me died down to a drip. I winced at the stress of the action omitting my full relief.

I gently press my opening against the lip of the teacup, catching any remaining drops as to not make a mess.

I fixed my panties and let my skirt down and then picked up the cup.

"You're tea ma'am." I said setting the fancy dish down Infront of her.

 

~••• Perspective shift to Ms. Fall •••~

I brought the teacup to lips and took a sip. The taste I was met with was a subtle sweet and salty taste that was finished with bitter taste in the back of my tongue. The aftertaste of Bergamot permeated the back of my throat making me breath a relaxing sigh. Nothing was like having your tea expertly mixed by a girl who's nectar was tailored just to your liking.

"Ah the benefits of being chairmen." My eyes closed soaking in the taste before opening them and seeing my assistance waiting silently.

"I suppose you've earned yourself some release. Present yourself Lilly"

I watched her as she turned around so that her back was to me whilst hiking up her skirt. Looking at the light pink panties she was wearing, I could see that the fabric had noticable bulge created from something that was planted at her rear.

She proceeded to bend over resting her hands on the stool in front of her, the one that I keep in the center of the room for this specific reason, holding the position.

I got up from my seat and walked around my desk over to my obedient assistant. "Have I ever told you how beautiful of an ass you have Lilly?" I say as I grab her ass cheeks roughly.

She yelps from the sudden sensation. "Ah!.. Uh... Uhuh."

"Uh-huh what? Use your words!" I say sternly as I let go of her right cheek and smack it again eliciting another cry from her.

"Ah!! Yes Ma'am! You've told me how much of a beautiful ass I have."

"That's a good girl. Honesty is very healthy for you to be honest about your talent." I say with a lighter tone as I caress her ass gently smacking one of her cheeks again. "Speaking of honesty," I let go of her, "How about you tell me what you want."

She hesitates for a moment before speaking. "Please Ma'am... My ass ..."

"What would you like me to do with your ass?

"Please train it more today so we can both enjoy ourselves more in the future an~!Ah!"

I smacked her soft butt once more watching it jiggle. "That sounds like a wonderful idea to me!" After which I hooked my right finger under the back cleft of her panties slowly drawing my finger downwards, parting the fabric from her crack. Then pulling it to the side to reveal a fairly sizable silicone plug that sat there spreading her out.

I crouched down beside her to allow a better view as I gripped the plug with a few of my fingers and began to softly pull on it. The sound of slick snaping and cracking filled the air as the lube was futally trying to keep the plug stuck to the skin.

I was rewarded with a gasp as her well trained hole began to give way to the big toy built to keep her ass stretched and prepped.

Before long the toy had reached its peak, coated in juices from the hungry hole that had initially swallowed it. And then "POP!" The plug sporadically popped out, a result of her asshole quickly contracting from the toy. Or perhaps lack there of now.

Though as per the usual now aday, it took a little bit of time to close up as her anus gaped open from the familiar object it had been sucking on for the past 12 hours. I caught a quick glimpse inside, seeing the soft slick pink insides of her ass contacting from the phantom object that it was supposedly gripping on.

Before long her ass managed to close back up almost all the way creating a soft vertical slit from its extensive training, as if it was its very own pussy.

"Alright, it's time to show me how much you've been practicing." I say bringing my arm up to feel her belly that was discreetly bulged out beneath her gown.

I could feel as she tensed up putting focus into using her muscles to push.

 

~••• Perspective shift back to Lilly •••~

After a moment of silence I felt my anus began to part as the light skin toned object, I had buried inside of me from a day ago, slowly emerged. Slickly, it slid out, dangling down the further it went.

"That's the first foot!" I could hear her say as I trained my body on pushing. She was counting the black markings on the specially crafted toy.

Two feet... Three feet... Before... "Shhhhhllllllck!" The weight suddenly beat out any purchase that my insides had on it causing the toy to fully flop out with a loud wet snaking noise. "ooOOHHhhh!~ I gasp a moan of relief from pushing out the toy, my lungs desperate for air.

An aftermath, which I barely heard over my painting, sounded like a rope falling as the length of silicone presumably piled onto the ground just behind my feet.

"Oh wow! Four feet! I think that was a new record for you if I'm not mistaken." Ms. Fall, said to me as I caught my breath. I could never get tired of that feeling.

"Alright dear." She said with me hearing the mischievous smile on her face. "Now are you ready to be trained some more?"

"Ms. Fall, your 10 O'clock is here." Suddenly came from the transceiver.

I could barely wait!

Notes:

Thank you for reaching the end of the story. I may or may not post more chapters depending on where I feel like this story can go. (And maybe flip it to 2nd person to make the rearder more insertable)

I have idea for more action with Lilly, but it's not solidified. Feel free to add any kink ideas in the comments.

Though please remember, no promises x)