Granny Boss Strokes My Cock at Work

I had just started my new job as a caretaker of an inner-city apartment complex. It was a very 'cruisy' job and made me feel like Jack Nicholson from The Shining; I had plenty of spare time to focus on the gym and writing.

My employer Cathy was a mature woman who looked as if she was in her mid to late 60s possibly even early 70s. She had dyed ginger/light brown hair and wore inner-city sophisticated female suit-type clothing. Cathy had piercing blue eyes and soft features; although slightly weathered she was by no means 'ugly,' and I found her pleasant enough to look at.

Cathy's husband had passed away about 5 years ago and I figured she may have been a little lonely and using the apartment complex as a distraction. It seemed she enjoyed having a fit, young guy in his early 30s with exceptional manners and very polite at her service.

I stayed in an apartment on-site and Cathy would come in every couple of times a week to train me in the office. It wasn't long before we were chatting about our personal lives whilst she sat to my right and every time I made a remark or wisecrack; Cathy would pat my thigh as if to say: "Oh you." After several thigh taps throughout the morning I became extremely horny. I was single; in my early 30s and hadn't had a girlfriend in over a year or so. I considered myself an attractive guy and a total freak with a very high sex drive. My imagination often ran wild and I had a very kinky side that sought to push the boundaries and spice up my life any way I could.

Later that evening I thought about Cathy tapping my thigh -- was she flirting with me? -- seeing that she was in the twilight of her life; I concluded that she was probably feeling just like me; bored, alone, horny and seeking some excitement.

I thought about Cathy rubbing my thigh and jacking me off at work. Maybe she'd even pay me a little more I pondered, perhaps even leave the business to me in her will? I had nothing to lose and enjoyed the idea of a reasonably attractive older women stroking my cock whilst at work with no strings attached.

During our training session; I decided to wear no underwear beneath my dark grey suit slacks that complicated my fresh white shirt with three buttons undone displaying my chest with a touch of fresh aftershave to boot. The reason I wore no underwear is because I wanted my hard-on to be prominent and on display through my slacks so Cathy would take notice.

As she walked into the office on the morning of our meeting and sat beside me; she greeted me with a nice strong cappuccino; before long we were sitting down and like clockwork -- the thigh tapping continued. As we discussed our personal lives; I mentioned to Catchy a few family problems which I won't get into but needless to say she placed her hand on my thigh as if to comfort me and momentarily held it there. I felt my cock jolt slightly and placed my hand on top of hers' which was resting on my thigh and said "Thanks, I appreciate that," as we looked at one another and gave a wry smile before releasing my hand and arching my back, running both of my hands down my thighs and letting out a sexually frustrated sigh.

This time -- I started to move my foot closer to Cathy's under the table. Beneath her light green, below-the-knee skirt she wore black pantyhose and one-inch black slides. Cathy reciprocated in casually brushing our feet against one another [playing footsies] as my hard-on became quite visible and I noticed her stealing glances from the corner of her eye.

The sexual tension was beginning to build and by the time the next thigh tap came around it turned into a thigh rub as we both stared into the computer screen and she moved her hand closer to my cock. Cathy then looked down and began tracing her index finger up my shaft and in between the crevasses of my thighs as I remarked "It looks like I found the right job after all,"

"I'm glad to hear," replied Cathy; keeping things as casual and professional as possible -- contrary to the event unfolding. I leaned back into my chair and undone two buttons on my fly. I never liked a zip; they made me cringe at the thought of catching some skin and I much preferred a button-up fly. Cathy continued to squeeze my cock through my pants and it wasn't long before it sprang free, much to my relief as the room began to fill with the sensual musky smell of dick. Cathy ushered her chair closer and placed her left arm around around my waist as her right hand slid up and down my shaft. There was a box of tissues on the desk and I knew these were going to come in handy! Cathy edged me to climax a couple of times; occasionally pausing and smelling her dick-scented hand which turned me on to extremes.

I felt myself about to blow and stated "You might want to get those tissues," as Cathy tore one after another from the box and wrapped them in her hand I groaned and my dick began pulsating and blowing my load into the tissues through my fly - it felt like I came for an eternity! Cathy looked seriously impressed as if she were taking sperm samples from a horse, and just like that, she scrunched the tissues up and placed them into the bin below before grabbing a few more and wiping my cock clean whilst looking at the tissues and smiling before binning those as well and doing both my buttons up on my fly. She tapped my thigh twice suggesting she was proud of me; signifying 'good job,' In what would normally be quite awkward afterwards, Cathy and I got straight back to business, looking at the check-ins for the day as we mutually remained oblivious to what had just taken place and I much preferred this! I didn't want my newfound pleasure to come with any headfucks and I soon found out my routine like handjobs meant no more than refilling a stapler - it was nothing more than workplace procedure!

As the weeks went by; Cathy mentioned we were going through an awful lot of tissues and she had a better alternative that was much more cleaner and efficient.

"Is that so," I responded as she removed the cushion from her chair and sat down beneath the desk. I smiled and began undoing my two-button fly. Cathy opened wide and placed her mouth around my cock with her false teeth and began softly scraping them down my shaft and gently biting on my pole. She looked good for her age and I didn't care about false teeth; if anything, it just turned me on more being the total freak that I was and forever searching for a new kink. I always thought how amazing it would feel having some gums wrapped around my dick - the ultimate suction! Cathy retracted her top row of false teeth with her tongue and held them out of her mouth at an angle resting against my shaft. It looked like a horror movie; grotesque but stirred my inner freak and was evidence to me that despite her age; Cathy too, was equally the freak. I took both rows of dentures in my hand and placed them either on the underside or front of my shaft. The friction felt nice and Cathy began to give me the most amazing blowjob. She sucked my dick like a fucking vacuum as I began groaning and squeezing the dentures around my dick as she sucked down hard like a baby lamb; I groaned louder and with slight exaggeration as I intended to let her know she was seriously pleasing me.

The dentures chattered as i rapidly squeezed them together. It was completely sadistic and freaky; holding this mature women's teeth in my hand and making them talk around the base of my dick whilst she was sucking me off. I placed the dentures back on the desk and held both of my hands on either side of her face and behind her neck as I forced her head down deeper on my shaft; showing zero consideration for her senior age and pumping the back of her throat full of my hot load as she gulped it down with enthusiasm -- a look of astonishment came across her face and she caught her breath. Cathy immediately looked about 10 years younger and rejuvenated. I felt incredibly relaxed as now I had her eating out of the palm of my hand or should I say smelling my cock from the palm of her hand! I no longer felt stressed around my employer. I started to reap the fringe benefits and came and went as I pleased whilst taking on many cash sales and under-the-table deals. Cathy never cared anyway, she was getting towards the end of her life and I was just her plaything and using her to feed my kink and my wallet!