I was 50, Samantha was 38. We are both married but it never went further than what I will describe. She has since moved on and is no longer working for the same company, I do miss her.
Ok, I will share an experience I had which I often think back on when masturbating.
I will admit it's not as hot as many of the stories I have read here, but here goes....
I have a bad habit of caressing myself through my pants. It's something I've been doing for years and just need to remind myself not to do this while with company.
The caressing I do is not to get myself turned on necessarily, just that it feels good and relaxing. This is often done on drives in my car; if there is a major backup on the freeway, then yah...I will slowly tease my cock this way until it hardens, allow it to soften and repeat the process. Great way of killing time while on a slow freeway.
A co-worker, I will call her Samantha, had her car in the shop, she lives near me so I offered to drive her home and pick her up the next day. Samantha is a lovely person, kind of quiet and to herself but she does a great job at the office and is dependable. She's tall, always shows a great smile and her red hair meets her shoulders.
Samantha is not a picture perfect ten, but an eight is not too bad either.
When we finished work, we went to the garage and into the car. Driving away I remembered about my habit and therefore kept both hands on the wheel. We talked about the boss, the workload and just normal mundane things that we do at the office. She had a quiet laugh which added to her beautiful smile.
I dropped her off at the house and told her that we need to be a little bit earlier at work tomorrow because of a project we were involved with and the deadline is right around the corner. She agreed to be ready at 6:30AM. This would give us plenty of time, and we waved as I drove off.
Next morning I drove up, she was already waiting for me by the driveway. She looked ravishing; she had on a greyish business suit with light white, thin pinstripes, her jacket unbuttoned showing off a pink blouse and the blouse showed off a wonderfully freckled cleavage.
She got into the car and we drove off. We chatted and I got into the old habit of mine, rubbing my penis through my slacks. I wasn't even aware I was doing this until I saw she glanced down at me a few times. I stopped and apologized telling her it's just a bad habit of mine since childhood. She flashed that terrific smile and said not to worry, 'if it feels good, do it!' Samantha said coyly.
So I put my fingers where they were and began the slow rub once again. We talked about the project wondering if we will get it done before the deadline. As we talked business, she would steal glances at my crotch, it didn't take long for the erection to begin.
Not only was it feeling good, but to have this sexy co-worker watch my 'habit' was very exciting. I wanted to change the topic, to talk about sex, how often she and hubby do it, her favorite positions, to find out if she masturbates, but I didn't have the courage.
After a bit, I was very pleasantly surprised to see her slightly freckled hand place itself against her pants suit the palm rubbing her 'area', through it. We didn't talk about anything at this point, just glanced at each others slow moving but busy hands. I was hard as a rock and it showed through my trousers, we entered the parking garage and Samantha asked me to park far away from the elevator. When I heard this request, I knew something more was going to happen and felt a little bit of precum ooze out of me.
I parked the car in a very secluded part of the garage. No other cars nearby, only a small yellowish light bulb shining its light into my car. Samantha pleaded 'Show it to me', her hand and fingers still rubbing against her pants. I unzipped, reached into my shorts and took out the veined erection for her to see.
'So big and shiny' were her words. It was shiny from the precum that was covering the dick head and shaft. She then moved her hands to the front of her pants, undid the belt, unfastening, her hands now went to the elastic band around her waist and pushed the pants along with her panties down her legs which she had parted. I almost shot my load right there when I saw her reddish bush.
Removing my hand off my rod I also undid my slacks and pushed them down with my shorts. Samantha licked two fingers and looking at my cock inserted them inside and sloshed her fingers in the wetness of her pussy as she watched me move my hand up and down the cock.
What a turn on, sitting in the car masturbating with my co-worker with just the yellowish bulb casting an eerie light on us. I looked down at her, I could see her fingers glistening with her juices. She breathed heavily as we watched each other. Nothing was being said, we just watched each other.
My hand moving rapidly up and down the hardness of my cock, more precum oozed out allowing me to lube it more, soon it was time for me to cum, I looked at Samantha again, legs spread open, her pants down below her knees, still in her open jacket and pink blouse slightly pushed up, getting a bit wrinkled as she wiggled in her seat, I saw her cute belly button, pussy humping wildly on her fingers, ohhhh that sloshing sound was such a turn on. I could not hold back any longer, I quickly reached between the seats where I keep a box of tissues and wrapped it around my hard cock as it shot load after load into it. Samantha saw the shots happening outlined in the tissue.
I was sweating from this experience and wadded it up to throw it away, she stopped me and asked me to hold it by her nose, 'I want to smell you' she whispered. I did as she asked, and watched her hips gyrate as her fingers slid in and out of that sexy red haired pussy, smelling the tissues of cum that I held for her, she then turned her head and moaned as she cummed on her fingers.
The next morning she already had her car from the repair shop. I drove to work and was about to park in my spot then thought about checking out the secluded area of the garage. I drove there, and to my pleasant surprise, there was Samantha's car, she was in it, waiting for me.