Before diving into today's story, I want to give a huge shout-out to Phil Anderer, the unsung hero behind the scenes. Phil's keen eye and editing wizardry have been instrumental in polishing my stories and banishing those pesky typos and spelling errors. Thanks to his expertise, I can share my thoughts with you all in a much clearer and more refined way. Big thanks to Phil for making sure each post shines.
I remembered when they hired Jane. She was brought in to be an administrative assistant and she was good at it. For months she made sure our calendars were up-to-date and the phone got answered.
She was always nice and wished everyone who passed her, a good morning or good afternoon. Beyond that she didn't say much at all. She would answer questions when asked, but generally kept to herself.
Jane was chubby, not fat, just overweight. She couldn't have been over too far over 20, and maybe 30 of 40 lbs away from a beach body. Her style of dress could be best called 'minister's wife'. It was layer upon layer of long skirts, loose fitting blouses and cardigans. I even caught a tissue pushed up her sleeve one morning.
Despite all this there was something about her. She smiled when I said "Hello", when I looked in her direction she was always looking back. I liked being around her. She also called me 'Mr. Wilson' instead of Dan or Danny. I couldn't have been any more than 7 or 8 years older than her.
About six months after she was hired, the company decided the IT department needed their own admin assistant. From now on she would be responsible for buying what we needed for repairs, updating our logs, and generally keeping a bunch of techs in order.
To accommodate this, they moved her desk outside an office I shared with Frank. I couldn't enter or leave my office without walking by her. She would almost jump out of her chair every time I walked by.
To start, I would ask her about her day. Then I got into the habit of sharing a joke with her every morning. Stupid stuff at first, but they got progressively naughty as we went along.
"What does the sign on an out-of-business brothel say?" I asked her one morning. "Beat it. We're closed!"
To make sure the joke landed, I mimed jacking off.
She giggled and covered her mouth. I watched as her face turned red.
It was a bit of a Human Resource nightmare, but I was sure Jane wouldn't report me.
"What's the difference between hungry and horny?" I asked her a few days later. "Where you stick the cucumber."
Same giggle, but this time Jane pointed to her crotch to show she got the joke.
There was something about this gesture, it's juxtaposition with who she was, that stopped me for a minute. I smiled back at her. I had to admit having this woman, who wouldn't swear unless tortured, pointing to her own crotch, was hot.
Because of this my jokes got more and more sexual.
"My girlfriend gave me a hand job the other day using Vaseline. I came three times trying to wash that shit off," I said one morning.
"Really Mr. Wilson?" she asked me, her eyes bright.
"No, it was just a joke," I told her. "I don't have a girlfriend."
"Huh?" She looked at me, head tilted. "That surprises me."
I just smiled and went into my office.
It wasn't lost on me that Jane might have a bit of a crush. Don't get me wrong, I liked the attention. However, there were two issues; Jane wasn't really my type and there were workplace rules about dating.
Jane started to offer to get me coffee in the morning.
"You look busy Mr. Wilson," she would say. "I don't mind grabbing a cup for you."
When she brought it in, she would hang out by my desk for a short while, leaving only when Frank came in or it seemed to have been there a little too long.
One day, I was reorganizing the equipment room, moving desktops around and storing them on shelves. Jane was taking down the inventory numbers with me and we were joking and laughing together.
One of the desktops was on the top shelf and I was having a hard time bringing it down safely.
I looked around for a ladder or step stool, however, once again it had been borrowed and not returned.
"Jane," I asked, "can I lift you up to grab that computer?"
"Of course, Mr. Wilson," she replied, jumping up and coming over.
I sized up the difference in height to the top of the shelf and grabbed Jane around the legs just below her bum. The result of which was, when I lifted her up, her bum was right in my face as I hugged her legs.
"Oh," she cried out, "I hope I don't fart."
Coming from anyone else it would have been normal or a joke between friends. Coming from Jane, it caught me completely off-guard. The laughing made me shake and Jane almost dropped the computer on my head. I slid her gently back to the ground by loosening my grip, but not loose enough to prevent her dress from riding up to her waist. For a brief moment, I noticed that Jane was in stockings, not panty hose like I would have suspected. She also wore what could best be described as silk lingerie of some sort.
"Mr. Wilson," she said, startled, "I am so sorry, that was completely by accident."
"Oh god," I replied, "my fault entirely. I am sorry, I should have done something different. Didn't mean for your dress to come up like that."
At this point I had verbal diarrhea.
"Well, that's your Christmas present taken care of," Jane joked, trying to ease the tension.
Without thinking I sputtered out, "Not fair, I didn't get a good look."
Jane looked at me for a minute and felt all the air leave the room. Had I just said that? I was going to be in front of HR before the end of the day.
While my head spun, and I tried to think of something to say, Jane placed her hands on the front of her skirt and started to bunch it into her hands. In a moment I was looking at the top of her stockings and then her silk panties. They were not see-through in any way, but light enough I could make out everything underneath. Individual pubic hairs were visible against the material.
I stood there in shock, my mouth hanging open. She was smiling at me and pivoting back and forth with one leg bent looking like a 1940s pin up model.
"Like what you see Mr. Wilson?" she shyly asked me. Her face was flushed, and I could tell this was new to her. She had taken a chance and was now hoping she wouldn't be humiliated by it.
"I do Jane," I stammered, "very sexy indeed."
I was quickly getting hard, and this didn't go unnoticed. Jane looked at the impression growing in my pants proudly. She was delighted her display had been received this way.
By this time my brain has switched tracks. HR was no longer my first concern.
"Are those silk?" I asked, finally thinking of something to say.
"They are," Jane replied, "feel them."
I moved closer to and touched the panel of material above her mound. An audible sigh escaped her lips. The material was super soft and I started to rub it a bit. I was now standing less than an inch apart from Jane with her forehead inline with my chin. This close, I could tell she was shaking a little, almost vibrating.
She looked up at me with her eyes partly closed. She was looking for a kiss. I was happy to oblige and tilted my head down. There was an eagerness about her kiss, like she was trying to latch on to me. At the same time, my movement lowered my hand a little more and I was now rubbing the top of her slit.
The moment I touched her sensitive pearl, I could feel her stiffen and her eyes shot open. Her arms were now around me and her fingers seemed to be trying to dig in, to hold on.
I kept gently rubbing her and she started to pant. I slid my finger into the side of her panties and continued with skin-to-skin contact. She was wet, so very wet. It didn't take that long until she was shaking in my arms.
As she calmed down, she relaxed.
"Oh wow," she said, "that was so much better than..."
She cut herself off. It was a funny comment, so I had to ask.
