Karen and I had worked together for about five years. While not extremely close, we were friendly and had a certain chemistry between us. We didn't interact on a regular basis, but we had fun kidding each other, and over time our normal office relationship evolved slowly into some mild flirtations and eventually to more overt sexual innuendo.
Karen had been divorced about three years; she was a single mom with one child. Not a 'looker' by any means, she was actually rather plain. Shoulder-length brown hair, green eyes, on the heavy side and a conservative dresser. But her personality was sparkling and she always had this mischievous glint in her eye and her laugh always made me wonder, for some reason, if there was more to her than met the eye.
I, on the other hand, am a middle-aged married man (45) with a few kids of my own, and a lackluster sex life. I have become a daily masturbator over the years, and my catalog of fantasies has grown during that time. As Karen and I continued to 'play and tease' during office hours, my fantasies began to include her.
One Friday I decided to ask Karen to lunch. We had been out on occasion for lunch before (maybe two or three times) so it wasn't unusual. We grabbed a bite at a local chain restaurant and our conversation was light and, as usual, packed with sexual innuendos. As we got in the car to go back to the office, Karen suggested we ride over to a nearby park as it was a beautiful spring day and we still had 30 minutes before we had to get back to work (we are allowed 90 minutes for lunch on Fridays. Nice perk, huh?).
I pulled into the nearby County Park and wound my way through some of the car paths until I found a parking lot with no other cars in it. This is a large, very beautiful park spread over about 500 acres and there are many walking paths and dirt parking lots-a lot of seclusion if you desire it! As I parked we continued our banter, both of us laughing and having fun being with each other. I turned off the car and we continued to talk, and the conversation shifted to the last time each of us had 'gotten some.' Karen confessed she hadn't gotten any since she was divorced, but managed to 'take care of business' on her own; as she told me this she visibly blushed and laughed some more, but maintained eye contact with me. I told her I knew how that was and that it had been almost two months for me but I also 'take matters into my own hands.'
Karen wondered when I had done so last, and I told her just the night before, shortly before bed, as I do most nights. I then asked her when she had 'had fun' and she told me it was a few nights earlier, after her son was asleep and in bed, and that she had gone downstairs to their finished basement so as not to wake him in case she got too noisy. More laughter from both of us, and I told her it would be so erotic to be a fly on the wall and watch her. She got that glimmer in her eye and told me how much fun it would be to have me watch her.
I was rock hard at this point, her sitting in the passenger seat and me in the driver's. No one was in sight, no cars in the parking lot, and the atmosphere in the car was definitely heating up. Karen was wearing a pretty floral skirt that reached her ankles and a white short sleeve blouse. I reached over and put my hand on her leg and slowly began inching her skirt up to reveal more and more leg. As I did so I looked at her and asked if she had toys that she played with, or if she was more of a 'hands on' lady. She told me she did in fact have toys, and it depended on her mood as to whether she used her Pocket Rocket or just used her fingers. As she was telling me this, I had exposed her legs up to mid-thigh (they were milky white, not very firm but VERY sexy to me; she had on no pantyhose) and she had shifted in such a way to make it easy for me to bring her skirt up. I began rubbing her left thigh and she sighed. I asked her which 'method' she had used a few nights before, and she told me it was just her hand. I wanted to know if she had taken off all of her clothes to masturbate (that was the first time I used the word with her...) and she told me no, she had just lifted up her nightshirt and rubbed herself through her panties.
I boldly lifted her skirt further, revealing her underwear. They were tan briefs made of nylon. I shifted to my side and reached over between her legs with my left hand and began to rub up and down her crotch. 'Like this?' I asked. She sighed and her head rolled back and she told me yes, JUST like that. I continued to slide my middle finger up and down between her legs, over her panties, and I could feel the moisture building up in the material. Her legs spread further and further apart, and as I glanced down I could see she was incredibly aroused; not only were her panties becoming wet she was flushed and her nipples had visibly hardened to the point I could see them poking against her bra and blouse.
I removed my hand from between her legs and she sat up, lowering her skirt and frowning slightly. I looked at her and told her it was one of my favorite fantasies to see a woman masturbate and asked her if she would do it for me. She laughed that devious laugh, pulled her skirt back up and continued what I had begun, rubbing herself through her panties. It was then that she invited me to join her, and asked me to 'take it out' so she could see. I didn't think twice and lowered the zipper to my dress slacks and pulled out my erect penis. She gasped quietly then giggled and said it was 'lovely.' The pace of her hand in her crotch increased and I began to slowly stroke my hard on. I told Karen to put her hand inside her panties, and she obeyed. This obviously took her to the next level and she was now moaning in pleasure. As I stroked my cock with my right hand I reached over and began to squeeze her breasts and tweak her nipples right through her blouse. Not more than a minute later Karen began to come with a series of low moans and groans, and she locked her legs together against her hand as she shook with pleasure. Eventually she leaned back and let out a 'whew' and told me how great it had felt. All the while, I continued to casually stroke away.
She looked down and saw me in action, and told me she wanted to help. It was a complete surprise to me as she reached under her skirt, lifted her hips and slipped off her panties, then smoothing out her skirt and blouse (I never did see her vagina during this encounter). She leaned over and nudged my hand away, and took her panties and began to ever so sensuously slide them up and down my cock. The sensation was immense, from the smoothness of the nylon to the moisture from her crotch. She began whispering dirty little things in my ear ('mmmm, what a nice big cock you have', and 'I want to see you come all over'). It didn't take me long, and I warned her I was about to shoot. We were both thinking ahead as at the same time we reached to pull my dress shirt up and out of the way, which caused us to laugh. She resumed stroking and before I knew it I was coming like there was no tomorrow-several long, healthy ropes of cum leapt onto my belly followed my 4-5 'minor eruptions' all over Karen's panties and hand. As I was recovering, she lingered on my cock and took her index finger and played with the semen on my belly before she wiped it all up with her panties (which she ended up stuffing in her purse).
We made a beeline back to work and only returned five minutes late from lunch. That was the first of several masturbatory lunchtime encounters with Karen, but we never had intercourse or oral sex. She began dating a man a few months back, and she is very happy, but since then she had told me that our lunchtime fun had to end. I'm disappointed, but I still jerk off to the memories of the times we had together.