I work as a salesman for a sizable company that employs quite a few other sales people. One of the women on my sales team is an older woman who always seemed to be rather friendly towards me. She would often make comments about the female customers I had and how I always seem to spend more time with them. I often felt as though we were flirting in a very subtle way.
She's in her early forties with dyed red hair, nice perky tits and a devilish grin. I would often kill time waiting for sales by checking out her tits and wondering if she was tanned all over or if she had tan lines.
One day I ran into her on the way back to the building after lunch, quite a long walk since we have to park on the far side of the lot so that customers can park near the building. She teased me about a young, blond female customer who I worked with earlier, telling me that she was surprised that I didn't spend more time working with her. I commented back that I would have if she had been a redhead.
'Oh, you like redheads do you?' she asked.
'Oh, yeah. Do you have any single redheaded friends you can hook me up with? Maybe then I won't have to masturbate as much.' I replied.
'No, unfortunately none of my friends are redheads. I wish I could help.'
With that we were interrupted by a fellow sales person and I couldn't continue the conversation, much to my dismay.
Later that day she came over to my office, closed the door and sat down to wait for me to get off the phone. I got excited seeing her sitting there because I was hoping that we could continue our earlier conversation. After seeing the look in her eye I quickly ended the phone call.
'I have a question I want to ask you. Earlier you made a comment about masturbating too much. Well, I have always had a fantasy about watching a guy masturbate and seeing him cum. I want to know if I can watch you masturbate. I can't touch or anything because I'm married, but I can watch.'
I started to get hard just listening to her talk about masturbation. I told her that I would love to have her watch me masturbate since this was already a fantasy of mine. The only condition I had was that she had to encourage me and talk dirty to me while I was masturbating. She said that she would talk as dirty as I wanted.
We finished the conversation by planning to meet at her SUV after work. I couldn't concentrate on anything the rest of the day.
As soon as work was over I walked out my car and waited for most of the other sales people to leave and for her to appear. She arrived and waved to me to come over. We got into her SUV and she began to drive down some of the back roads behind our building. The darkness and her large SUV afforded us some privacy as she started to talk dirty to me.
'Is your cock getting hard? I bet you have a nice big cock that you want to stroke for me.'
I now had a raging hardon that I needed to stroke so I told her to park at the end of one of the streets that they were building houses on. As soon as she parked I pulled my trousers down and my cock popped out.
'Oh, that's a nice cock. I want to see you stroke it for me. My pussy is getting so wet right now thinking about you jerking off all the time.' She said in a low soft voice.
I started stroking my cock as I looked over at her and listened to her dirty talk. Soon I was moaning softly as I listened to her and I could see that she was massaging her boobs through her shirt. Seeing this really got me going and I was getting ready to come. I told her this and she opened the glove box and pulled out some napkins from a local restaurant and placed them on my lap for me to cum onto.
'I want you cum for me, I'm so fucking wet right now I can't stand it.'
I tilted my head back and let out a groan as I began to come, launching several ropes of cum up into the air and onto the napkins.
'Oh god, that is so much cum. Keep jerking your cock I want to see more cum!' She moaned.
She continued to play with her nipples and talk dirty to me as I finished stroking my cock trying to squeeze out every last bit of cum that I could. It stopped there because we saw a car coming down the road towards our dead end street so we hurriedly cleaned up and I pulled my pants up. On the way back to drop me off at my car she continued to tell me how wet she was and how she really wanted to finger herself and couldn't wait to get home to do that. I promised her that I would jerk off for her anytime she wanted and that I really wanted to see her finger herself.
We have since had several more encounters that I will write about later.