Right out of college at age 22, about 5 years ago, I started work, not a boring 9-5 desk job, but corporate nonetheless. I was put through a training program to learn how to do the job, and in order to graduate from the program, I had to have once a month check ins with the hiring manager.
Her name was Cindy, she was laid back, professional, very personable, and had the mom next door vibe. She was in her early 40s, had a couple kids at home, and was going through a divorce. She mostly worked from home, so we really only saw her when we had scheduled meetings.
Something about her though caught my eye. Her voice was sultry and kind, she dressed in unassuming work clothing, but you could tell even at 40, she still had it. Her wavy brown hair and bright red lipstick always caught my eye.
Our first couple meetings were straightforward, we would work for a few hours in the morning, go grab some lunch, then go back to review at the office. We got to know each other pretty well at these lunches. Both professionally and personally. I found out all about her divorce and frustrations with that.
We trusted each other, and before you know it, she was inviting me to her corporate events to “help out” but really I knew it was to spend more time with me. We traveled to meetings and ate dinner together.
I could see it in her eyes, hear it in her voice, she wanted me. And no matter how much I tried to hide it, I think she knew I wanted her too.
One day we had to travel to another city for a conference, and she invited me along. This was after I finished my training so no more conflict of interest. Was it time to finally let the tension between us boil over?
She even offered to drive me all the way there and back, booked my hotel room, and took me to dinner every night at this week long conference. I knew what was going to go down.
We spent all day together at the conference, and even though she didn’t really “need” me there, I tried to keep busy and help her out to keep my mind off of her body.
At the end of the conference, it was dark out, it was November so it’s pitch black by dinner time. We hop in her car, and she suggests a place for dinner next to the hotel. I say I’m down and she drives the rental car to the hotel and we park in the lot far away from the front door.
She shuts off the car, it’s pitch black out except for the dim glow of the hotel lights, it’s dead silent, and we just look at each other, barely able to see each other’s eyes. She leans in closer to me and I feel her fingers gently graze my thigh. Blood rushed to my legs, my heart beat furiously and my shaky hands reached around her shoulders.
Her red lipstick covered lips were now gently sucking in my lips. By this point I could feel her hands running down my face to my chest, where she grabbed my hand and placed it on her breasts. They were practically bursting out of her blouse, so I pulled off each button and saw her bright red lingerie bra underneath.
She could see my erection about to bulge through my pants, I had never been so turned on so fast. Her bright red nails fumbled to pull off my belt and unzip my trousers. When she finally got ahold of it, she stopped kissing my face, leaned over towards me, and took my cock into both hands.
I could tell it had been a while since she had done something like this, but her red lipstick was about to cover my cock.
She sucked me in and I moaned and her warm tongue caressed my Dick. It felt amazing, I had never been with an older woman, and even though I could tell she hadn’t sucked someone off in years, the sudden excitement and tension overcame me. I was about to explode, months of tension finally came to a peak. As I could feel her sucking harder and harder I almost started to scream. I didn’t want to finish after just a couple minutes, but this was too hot. Before I could even utter the words “I’m gonna cum”, I was squirming in my seat as I lost control.
My rock hard cock was in her lips’ vice grip as if she was sucking the cum out of me. I had never shot as much in my in my whole life. She could barely keep up with it all coming out, she lifted her head up to swallow, her first time in a while it looked like. Her hand still on my shaft I was still cumming loads all over her hand.
I felt embarrassed to have only lasted that long, but she said not to worry, she was probably proud of making a guy finish like that, she suggested we clean up, and go into the restaurant for dinner, then we can spend some alone time together again later.
Pt 2 coming
Source: reddit.com/r/eroticliterature/comments/p9gon8/my_first_time_with_an_older_woman_at_work_mf
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