Meet My Lady Boss

Amateur

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 sincan escort 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.

It felt sensational, I moaned and looked down to see and feel her hand squeezing my shaft through the material.

“You’re a kinky one Dave and that cock feels lovely and hard, I hope it’s going to stay that way for me.” Jill purred as I thrust slowly beneath her hand as sincan escort bayan she pressed and squeezed.

I moved my free hand round to her knickers and started to rub her mound through the material, drawing gasps from Jill. The sensations I was feeling through my cock were almost too much to bear and I pulled out of her stocking before I made a mess of us both.

Pinning her to the wall briefly I dropped to my knees, lifted her left leg to wrap over my shoulder as she stood, and buried my face between her legs.

Licking and mouthing her pussy through the lace of her knickers, her hands in my hair, pressing me firmly against her. She could feel my firm tongue probing and pressing, and the hot breath from my mouth on her pussy but it was a real tease for her, and I knew it wouldn’t last for long.

I was right as she reached down to yank her knickers to one side before gripping the back of my head, firmly pressing my face into her pussy. My tongue flicked and probed the folds of her sex, spreading, finding her clit and flicking it fast and hard for a couple of moments. Her knees buckling slightly she sighed “Fuck mmmmm that’s the spot” as I pulled away gently to suck her puffy pink lips into my mouth one at a time.

More sighs then the command “Lick my fucking clit more, that’s what I want!”

I went to it with vigour and passion, my tongue circling then beating against her swollen nub. Inhaling deeply, the smell of her sex intoxicating to me. Jill gasped and sank her nails into my scalp “Fuck yes, yes you dirty bastard, suck my clit” She growled. I knew she was enjoying the tonguing I was delivering to her clit, but there was something else, she was turned on by how much I was enjoying eating her out so passionately.

I couldn’t stop now and kept up the sucking and licking of her most sensitive spot, my hands gripping her ample buttocks, squeezing them hard as I sucked and munched on my boss’s snatch. She loved controlling the situation, having her subordinate kneeling before her sucking and licking her the way she wanted.

The feel of my firm, hot, tongue flickering and probing was so intense and pushed her over the edge soon after, the hot ball of tension between her legs exploding in spectacular style as she fucked her cunt against my willing mouth, cumming hard, her legs shaking almost giving way but being held up by my efforts as her juices flowed into my mouth. “Mmmmmmmmm God almighty that was good Dave, fuck yes mmmmmm, I haven’t been licked for at least 2 years.” She sighed as I pulled away looking up at her.

“Really? He doesn’t do this for you?” I couldn’t believe it as I enjoyed oral myself so much.

“No, the beanpole doesn’t like the taste so he says, but never mind him, it’s time you gave me the fucking I told you about.”

“Yes boss lead the way.” I laughed giving her a mock salute.

We got rid of our clothes, Jill taking pleasure in wrapping her soaked knickers around my straining member to wank me with. I lay back as she did this with my eyes closed loving the feeling of the lace on my veiny shaft.

Jill tossed the knickers in the corner and kept hold of my cock, precum running down from the head over her fingers as she slowly rubbed up and down varying the pressure in the most wonderful way.

She straddled me now, rubbing the head of my manhood on her slippery pussy lips as I sucked and licked her breasts, each nipple a hard pebble aching and throbbing for attention from my hot mouth. I obliged of course, closing my eyes and losing myself in the pleasure of the moment.

“Lie still now Dave, I want to feel every inch of you in me now.”

Saying this she lowered her sweet sex onto my rigid cock, she could feel the hardness stretching her neglected hole deliciously, slowly but surely filling her until she ground her clit firmly against the base of my hardness. Her clit throbbed and tingled as she drew herself back up halfway before sinking back down “Now that’s what I’ve been wanting all day long mmmmmmmmm.” She sighed.

Her pace stayed steady for a few minutes as my hands explored her curvy arse cheeks, stroking and squeezing them, sending tingles and shivers across her skin, while my mouth busily sucked her beautiful big tits. Jill shuddered and moaned as I started to thrust up into her, meeting her downward thrusts with upward motions of my own. “Good lad, just like that, don’t you fucking stop.” She gasped.

The grip her pussy had on my cock was amazing, her muscles felt so strong, squeezing hard against my member with each deep thrust. I was finding it hard to control myself and my breathing grew more rapid, gasping and thrusting faster now.

Jill recognised the signs and eased me out gently. “No way you’re cumming yet Dave, I’m enjoying myself too much and I want another orgasm before its your turn.”

I caught my breath escort sincan grateful for the respite, Jill climbed off me and lay on her back spreading her legs wide which I knelt between. “It’s been a long time for you hasn’t it?” I said quietly as she took hold of my straining manhood, guiding it into her velvety smooth pussy once more.

It felt exquisite, so wet and hot, so out of bounds fucking my married boss like this, my own wife at home unaware of my betrayal. So many thoughts but strangely no guilt, why no guilt?

“He hasn’t fucked me in ten months, not that I’m counting, now less talk and more action or I’ll send you back to your room.” She replied closing her eyes as I thrust in balls deep.

“Of course you will.” I teased whispering in her ear as I drew back and thrust deep again.

“Mmmmm yes fucking do me Dave, fuck me HARD.” She hissed urgently.

I needed no second telling and ploughed my cock into her with force and passion. Pushing her legs higher so I could go deeper I watched her pulling at her nipples. “Fuck Dave is that all you’ve fucking got?!!” She complained, spurring me on to greater effort, faster, deeper, harder as sweat began to bead on my forehead and the small of my back.

“Mmmmm better, fuck yes keep going fuck me ragged you horny bastard!” She urged.

I smiled into her neck, nuzzling and kissing as my balls slapped wetly against her arse cheeks with each rapid thrust. I loved a bit of dirty talk, and Jill seemed to enjoy blurting out whatever she was feeling at the time.

I was in a wonderful place now, the place where I’d gone past the point of feeling like I was going to cum too fast, to the point where I knew that I could last, and within reason, cum when I was ready to.

Jill’s moans were louder now, her finger nails digging into the cheeks of my arse in a painfully pleasurable way. The talking had stopped now and Jill had her hand between us rubbing hard at her clit, the other hand squeezing her breasts, pulling hard on each nipple in turn as her chest and neck turned a rosy shade of pink.

I managed to increase the pace of my thrusts one final time, and watched as her hips bucked up against me, her eyes at once tightly shut, then wide open as her orgasm arrived. Longer and deeper than her first, it washed through her in wave after wave. Her hand pressed hard onto her pussy as she shook and shuddered. “Ohhhhhhhhhh fucking hell thats good.” She murmured as I eased myself out of her now well fucked pussy.

She moaned again and reached down to rub my swollen cock, slick with pussy juice she wanked me firmly.

“Now you’re going to cum for me Dave.” She looked me straight in the eyes as she said this and I relaxed feeling my own orgasm starting to build. Her hand gripped my shaft tightly as she wanked me faster and harder. “Fuck Jill yessssss mmmmmmm.” I moaned in appreciation.

“Cum for me Dave, cum all over me.” She urged me on, and was rewarded with hot cum spurting out of my manhood in long sticky ropes, bright white on the skin of her belly and breasts. “Agggghhhhhhhhh fuuuuuuuckkkk” I cried at the ferocity of my orgasm.

Collapsing onto the bed beside her, sweaty and spent, I caught my breath.

“Don’t lie there for too long, get your arse back in your own room.” Jill ordered.

I propped myself up on one elbow, “Really? Just like that?” I replied.

“Yes just like that, this is no grand affair or love story Dave you know!” She almost shouted.

“I never said that it was Jill, I just wanted to talk with you for a while.” I replied evenly.

“No talk, just leave, I needed a fuck and you delivered, end of story.” She said this forcefully and I took no time in pulling on my clothes, I was pretty sure that there was an element of guilt driving her cold behaviour.

I knew we weren’t going to run off into the sunset together, but I wanted a bit more respect or appreciation than this.

As I opened the door she called out. “This never happens again, do you understand???” This last statement delivered with her voice shaking with anger or upset, I couldn’t quite tell which one.

I said nothing, closed the door quietly and headed into my own room. I thought about what had just happened and reasoned that after the fun, the guilt had hit her really hard. I couldn’t blame her for acting the way she did.

There was something else though; I didn’t feel guilty at all. This worried me as I was starting to think that yes indeed, the feminists were right all along. All men are bastards, and I was the latest to realise my own nature.

The next morning, we had breakfast together as colleagues, with no hint towards what had happened the previous night. Meetings were attended, and we said our goodbyes before heading home.

As I drove my phone flashed up a text message:

“Sorry about last night, I won’t speak to you again like that, you didn’t deserve it, have a good week.”

I didn’t reply, just kept on driving, thoughts in my head buzzing around like demented bees.

All men are bastards and women? Well, women are women aren’t they guys? And we will never figure them out.

To be continued…

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