I had a lady boss some time ago, she was good to me, never put me under any undue pressure and appreciated my need to work without being micromanaged.
I had a great deal of respect for Jill, because she gave me space to go about my sales role, visiting brokers to sell them our financial services packages for mortgages, but was on hand with support when I needed it. She was older than me by around 5 years, and had been in the game a long time and knew everybody, at that time in my career I was still a bit of a newbie but had been successful in my first couple of years.
Jill had been pleased with my progress, and because of this I'd had a nice pay rise and was pushing for a step up within the next couple of years.
Jill and I were out together in the car to meet an important broker, this wasn't a regular occurrence but I had asked her to come along with me as she had made a big deal with this guy previously when she was in my role.
"How's Tom and the kids?" I asked as I steered the car through rush hour traffic in Glasgow.
"He's still a lanky bookworm, and the kids are driving me up the wall is the honest answer." She replied as she gazed out of the window.
"He must be what? Six foot six, six foot seven?" I said admiration in my voice. I had always wanted to be a strapping six footer but had to settle for the higher numbers after five feet.
"He's six six and I have to crane my neck to kiss the big bugger, I just wish that everything was in proportion." She gave me a knowing look starting to giggle as I looked back at the road.
"Well size isn't everything you know?" I chided her.
"Maybe not to you it's not." She fenced back at me collapsing into fits of laughter.
I was surprised at this; Jill was always one of the boys, most of her team were male, and she had a very rude sense of humour which was good fun, but I had never heard her complain about her husband before, even in jest. I had met him before, and he was a very easy going guy, maybe a little bookish, while Jill was more of an extrovert and could certainly set a fire under somebody if they warranted it. They say opposites attract and in their case this was most certainly true.
"What about you and yours Dave, things going along well?" She asked.
"Yes pretty good, you know what it's like with two small kids." I replied rolling my eyes.
"You can't be getting a lot of sex with all of that going on at home Dave." She said whilst giving me that knowing look again.
"Why do you think that?" I replied warily.
She was right, since our second was born, my wife and sex were two elements of my life which didn't exactly go hand in hand. I still wanted my wife, but all of her focus was on the children, and after nearly two years of sex that happened once a month if I was lucky, I was feeling a little unwanted and under appreciated to say the least.
"I've had my children remember?" She sighed in exasperation. "I know what it's like to go off the boil it's not easy for us women you know?" She trotted this out like some sort of mantra and I thought it best to keep quiet at this point.
I looked over at Jill, shortish dark brown bobbed hair, large expressive brown eyes, a mouth that was just a touch too wide. Not a classic beauty but attractive enough in her own way. Jill was a curvy girl, most likely a Uk size 18, all in proportion, big boobs and a curvy bum topping some really rather good legs on her which she always kept sheathed in what I assumed were tights. Today she was wearing a black dress which buttoned down the front with a thin leather belt across the waist.
It's not part of my job, but after her outburst in the car I thought I would play the gentleman to help soothe her, so I opened her door for her after parking up. "Why thankyou kind sir." She laughed as she swung a leg out of the car. Suddenly a gust of wind blew her dress open from knee to waist as she tried to get out with some modesty.
I got an eyeful of her legs wrapped in beautiful black silk stockings with proper suspenders attached with shiny silver clips. I also noticed she was wearing lacy knickers and quickly covered my eyes in mock alarm.
"Jesus Jill, that's all I need to see before we meet this guy, I won't be able to concentrate now!" I laughed.
"Fucking wind." She growled. "If you're feeling traumatised by what you've just seen, you're welcome to speak with Jennifer in HR and put in a complaint." She said in her most sarcastic tone.
"No complaints here Jill, I feel like I just got my Christmas bonus early that's all!" I laughed.
"Give over, I was right; you must be bloody sex starved if you think that was a bonus."
I kept my thoughts to myself, but had in all honesty been delighted at the quick flash I had been afforded by the wind.
The meeting went very smoothly, my idea to bring Jill was a good one, and after an hour or so we had the deal signed and were headed back to the car.
We attended three more meetings before calling it a day.
We would be staying over tonight as there was another meeting to attend early the next day, and I was looking forward to having a night out in Glasgow, one of my favourite cities.
We had arranged to meet some clients later on but as we drove to the hotel, I received a message to say that they couldn't make it due to illness. It seemed Jill and I were on our own for the evening.
Rash thoughts of making a move on Jill sprang to mind as I listened to her talking on the phone as I drove. The view of her stocking tops, and the smooth white skin above them, the hint of hair behind the lace of her knickers had stuck in my mind and just wouldn't go away.
The lack of sex at home and my needs were fogging my brain.
It was a stupid idea, and a great way to ruin things with a boss that I liked and respected; but I was still thinking about that view as I pulled into the underground carpark at the hotel. I'd have to recall it later when I inevitably took myself in hand, later in my room.
It was around 6pm now and Jill was happy to get a bite to eat and retire for an early night. We chatted as we ate, about the day's events, before I ventured. "Must take you a while to get ready in the morning with all those straps and clips etc Jill?" I grinned.
She returned the smile. "I always wear them, have been for years, they make me feel very special and feminine. I have to have something for me in this testosterone fuelled team of mine." She sighed.
"I guess it's like when I pull on my suit, I always feel good, smart and handsome even." I replied.
"Handsome would be pushing it Dave, but yes I think it's a good comparison" she teased.
We settled the bill and headed into the lift; there was an atmosphere between us as the lift rose, I could feel it but I wasn't going to do anything stupid. Jill broke the silence saying "I was cruel just now Dave, you've always looked handsome in your suits."
"Well I'm very flattered that you think so, and I meant what I said earlier about my Christmas bonus; just so you know." I replied hesitantly, my eyes never leaving the lift doors.
We walked in silence along the corridor, the tense atmosphere still clinging to us like a cloak. Arriving at her door, Jill turned to me and said in level tones. "If you'd like another look at your Christmas bonus you'd better follow me, I won't ask twice." With this she opened her door and went quickly inside. I was stunned; however I didn't say a word or hesitate and followed her, closing the door behind me.
Inside she pushed me hard against the wall kissing me aggressively, I kissed back our tongues fighting as our hands explored each other's bodies.
"I'm still the boss remember." She gasped between our passionate sloppy kisses.
"What???" I moaned feeling her hands squeezing my arse cheeks firmly.
"This goes down my way, you do as you're told, and you fuck me the way I want to be fucked, do you understand?" She hissed this directly into my ear as my hands undid the belt and buttons on the front of her dress.
"Whatever you say boss, I just work here!" I grunted taking a large breast in each hand fondling them through the lacey material.
She laughed throatily "Squeeze them harder Dave mmm yes." Her breasts felt amazing in my hands as I squeezed and rubbed, kneaded and pinched them drawing appreciative gasps from Jill.
My own moans filled the air as I felt her hand massaging my stiff cock through my suit trousers.
She soon had my trousers and boxers down, and unexpectedly she span around rubbing her curvy arse cheeks on my erection. I reacquainted my hands with her beautiful big tits and kissed her neck, nibbling and nuzzling as she reached back to rub my cock against her bum.
"You liked my stockings didn't you Dave?" She breathed.
"Mmm very much." I sighed taking my hands away from her chest and rubbing them down her thighs, feeling the smoothness of the silk, and the warmth of her flesh above the stocking tops.
It was then that Jill turned slightly and pulled my cock down painfully, guiding it between her stocking top and her warm firm thigh. I squatted slightly taking the strain off the base of my member slightly, and placed a hand under her thigh lifting her foot off the floor allowing me easier access as I pushed deeper into the silky embrace of the stocking.
