It started in such a simple and silly way. A bunch of us were out, in a crowded bar, huddled in small groups so we could hear each other, and the topic of grooming came up.
Kimberly tended to be the quiet one in our group and because of that I always tended to gravitate to her, to try and include her in conversations, to try and pull her out of her shell. Plus she was adorable, with a round cherubic face, large expressive eyes, big cupid bow lips, and the habit of covering her mouth when she laughed.
She was always made up so well, beautiful clothes, hair perfect, makeup on point. I asked how long it took to get ready before going out and she said sometimes hours.
She was always equally complimentary to me, commenting on my suits, my hair, my always finely shaved face. It was flirtatious, but light. She knew how much she was my type, but she was a bit innocent and inexperienced, despite her dirty tumblr and occasionally provocative conversation points.
As our conversation moved from makeup to hair to grooming, the topic of shaving came up and she stuck her leg out and pulled up her dress a bit to show her smooth calf.
She was a thick thighed delight, with strong legs and a huge bottom. Looking her up and down from her exposed leg to her wide hips, to her rather small bosom and angelic face I tried to keep my comments appropriate, but failed.
"Oh, they look wonderfully smooth, but what about everything else?"
She let her dress fall back down to cover her leg and covered a little laugh.
"I like it all gone," she admitted, looking down at her wine.
"Which is well documented as your preference," she laughed.
I shrugged. Guilty. I was known for my preference or perhaps obsession with fully shaved pussies.
"Yeah, well, I guess I've mentioned it a few times. It's just so soft and you can see everything so much better. I don't know. Also it's like there should be hair there, but there isn't. It makes it look extra naked."
She smirked at that.
"Well, I don't know about all of that, but I like the way it looks and love the way it feels but when I'm not dating someone it's just a hard thing to be bothered with," she admitted.
"Well if you like it then maybe it's something worth bothering with," I offered.
She pouted, "I know but it's not like makeup where people see it and compliment it and even expect it, that's just something for me and-"
"So then don't make it something for you. I'll tell you what, from now on once every two weeks you come and find me and I'll inspect you. If you aren't smooth and clean then we can work out some kind of punishment."
She looked away and I wondered if I had gone too far.
"Or not. Just an idea. Thought it would be intriguing."
"What kind of punishment?" She said, looked at me over her thick lashes.
I laughed a little. I reminded myself that she wasn't that experienced. One game at a time.
"Well, for one I'll be very disappointed. This really isn't about punishment, it's about accountability. Maybe we can just say, if you miss or fail three inspections we will consider it a failure for the season."
I watched her wrestle with that. A punishment was something that could be fun or at least something she could figure out how to handle, disappointment was not an option.
"What would an inspection entail?"
I smiled. She squirmed under my gaze.
"What do you think it should entail?" I asked, sipping my whiskey.
Put on the spot, she bit her lip, fidgeted, and shrugged.
"I guess, like, checking me, down there."
She was blushing and stammering a bit.
"How?"
She let out a long breath and a nervous laugh.
"I don't know I guess, like, go somewhere and pull up my skirt and pull down, like, my panties or whatever."
I sighed and looked for the bartender for another drink.
"You think I would be able to see like that? Because I am thinking you will only be thorough if I am thorough. It would have to be in my apartment or somewhere else where we have room. I'll put you on a bed or a table, take off your pants or pull up your dress, take off your panties and really examine you. Get close up, spread your legs wide, so I can see everything," I said, catching the bartender's eye and pointing at my glass and hers.
The bar had a good bartender, she remembered our orders and nodded that she would bring us another round. When I looked back and Kimberly, she was staring at the floor and her cheeks were even redder.
"Oh, that is thorough," she said so low I almost couldn't hear her.
"I'd have to touch too. You can see if it is shaved clean but you need to feel to make sure it is smooth."
She nodded but didn't look at me.
"That's a lot, I don't know if I could make it up to your apartment twice a month. Maybe that could be once in awhile and you could just do a less thorough check sometimes?"
I smiled at her again. Negotiation of the details meant I had already won.
"I'll write you an email with all of the instructions. You let me know if you agree."
She looked up at me then, still biting her lip, still blushing, and nodded as she met my eyes from under her thick lashes.
The next time we were all out to drinks I made a point of not bringing it up. She was more quiet than usual the whole evening, never really engaging with me.
When it got late and I was ready to leave, I watched her gather her courage and come up to me and tug on my sleeve.
"So, um, do you want to do what we talked about?"
I cocked my head.
"What was it again?"
She clenched her jaw and cut her eyes.
"I'm kidding. Yes that would be lovely. Do you want to just find an empty bathroom or should we do something more thorough since this is the first time?"
She played with the hem of her shirt and nervously bit her bottom lip. She shrugged.
"I don't have that much time tonight, let's just do the bathroom. Next time we can be-" she swallowed, "thorough."
I nodded.
She eyed me and walked to the back of the bar. It wasn't that crowded. I gave it a minute and followed her.
She was holding a door open and motioned for me to join her. I rushed over and when I was in she closed and locked it.
