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.
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.”
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.
It was a small but clean bathroom. I stood in front of her and she pressed herself against the wall. I turned on the light and she winced for a second.
I looked at her expectantly. I was expecting her usual petulant nervousness, but although she was squirming in place she wore a smirk.
She was wearing a longish gray pleated skirt and knee high socks. As I watched, she took a deep breath and pulled her skirt up to her chest.
She looked up at me, holding her skirt almost to her chin.
“Ready for inspection.”
I knelt down, one knee on the hard tile. My face was level with a pair of somewhat plain pink silky panties. Her thighs were thick. It was the most intimate I’d ever been with her.
I reached up and took her panties by the sides and pulled them down to her knees. As I did, she opened her legs a little more.
My gaze went up her black knee high socks, to her smooth legs, to a perfect chubby triangle of pale skin between her thighs with a neat slit.
Her breath was loud, echoing in the little room. She was breathing hard.
I took my time, looking her over. I touched her thigh and she jumped a little.
“Open your legs a little more,” I said softly.
She did immediately.
With one hand on each of her thighs I moved closer. There was a softness to the skin between her legs, like baby fat. She did a good job shaving. I didn’t see any bumps or marks. I knew she was very into lotions and skincare, so I imagined she had a way of shaving that protected her skin.
My hands moved up her thighs and she stopped breathing for a second.
“I’m going to touch now, to see how smooth you got it,” I whispered.
Silence, no breathing.
My hands moved up her thighs slowly and her breath caught again. My thumbs slipped across the very bottom of her lips. I spread the pale skin to expose soft pink inner lips.
There was something remarkable about seeing a new pussy for the first time, especially a friend’s pussy, someone I had known for a year or two and had never even kissed.
It was so pretty I had to remind myself of what I was there for. I lightly slipped my fingers over her mons, down each of her lips, slowly down.
Her voice caught and her knees closed a little bit she steadied herself. As my fingers moved further down I understood why she was getting more self conscious. She was soaking wet.
I let out a little chuckle and she whined in embarrassment.
I traced where her lips parted, my finger just brushing her clit, and her knees almost buckled. I moved them back down and nearly slipped the tip of my finger into her wetness.
“Oh,” I said with concern.
She looked down at me with worry.
“I-I’m sorry. I know I’m all wet,” she whispered sadly.
I laughed again.
“Oh no, that’s delightful. You are dripping wet just from a little touching? Marvelous. No, it’s just that right here,” I said, my finger once again almost slipping into her, “there is just the tiniest stubble.”
I rubbed it again, feeling the little bristle of a few rogue hairs.
She whined again and poured and squirmed. It took everything I had not to slip my finger into the heat that was so close or moved a few inches forward and kiss the softness in front of me.
“Does that mean I don’t pass?” She said, sounding heartbroken.
I continued to rub that little spot. She was pushing her hips forward a little, trying to get more contact with my fingers.
“I don’t know. It’s very good. Very smooth and almost perfect. Do you think you should pass?”
She was breathing faster, her chubby pussy pushing out farther, her butt no longer against the wall. She didn’t answer.
She shook her head and opened her eyes.
“Sorry, What was the question?” She said dreamily.
“It isn’t perfect. Do you think you should pass?”
She sighed deeply, leaning back against the wall.
“No, sir,” she said dejectedly.
“Sir?” I repeated.
Her already bright red cheeks seemed to darken even more.
“Oh. Sorry. Is that okay. It felt like what I should call you right now,” she mumbled.
I rubbed a little more, my hand covering the whole of her bare mound. I stood up, keeping my hand there.
“Hm. Maybe. We’ll have to see. There might be extra rules if you want to call me that.”
She closed her eyes again and bucked her hips, causing my finger to slip between her smooth lips and feel the silky wetness again.
“I like your rules so far, sir.”
With that, I removed my hand from her body and looking in her eyes slipped one of my fingers into my mouth.
“I think your pussy is pretty enough to deserve to be perfect. This will be your first strike. I hope you will do better next time. Since it will be an extra thorough examination.”
She leaned down and pulled up herself panties and straighten herself out.
“I understand, I’ll do better next time,” she said, more determined than disappointed.
“I’ll do better next time, sir,” I corrected.
Her face lit up.
“I’ll be perfect next time, sir.”
As we snuck out of the bathroom I wondered which of us was going to be squirming more thinking about the next examination.If you liked this story you can send me a tip via paypal.me/writingdirty