Cougar Co-Worker [MF]

She was 51, I was 27. It’s sometimes hard to believe that nearly six years has passed. I started my first job in “education” fresh out of college. At the time, I found myself lucky to be back at my high school. However, you find out quickly that nothing ever changes. The secretary who provided hundreds of boys with fantasies during my formative years was still working there and this time, freshly divorced. There she was, all five feet of her Italian-American olive-skinned curves. Brunette waves gently touching her shoulders and breasts that were balanced out well by her thick ass.

We developed a friendship easily and the office flirtation grew over time. Her sex appeal was evident as was her naivety. She confessed to me that she had never been with a man other than her ex-husband whom she had married at 19. I was in a serious relationship and didn’t want to fuck anything up, so I never stepped into my fantasies. Until I became unhappy – and she noticed. It only took about four and a half years, but we tiptoed into it.

My office was in the basement of the school and I was alone at the end of an August day. Our flirting was growing to a point where the only reasonable ending would be to part ways or collide. With her guidance, we eased into a collision. She called down at the end of the day, knowing we were the only two people left in the building. She entered my office and sat across the desk.

“You’re nervous,” she said.

She was right, I was sweating, nearly trembling, knowing what I wanted and yet trying to remain faithful to my partner. I fumbled around. Hesitant. All those teenage rejections playing in my mind.

“What about just a kiss?” she asked.

We stood up from my desk. I watched her ass sway in her tight jeans as she sauntered toward the door. Her silk magenta blouse exposed just enough neckline to get my blood rushing. She backed into a set of lockers, inviting me to press against her. We kissed. I was instantly hard and she couldn’t resist rubbing me through my thin black pants. We went back into the office and now I was anticipating her bent over my desk. I was pulling on her waistband enough to see the top of her Calvin Klein panties. I was ready to dip my fingers inside of her when she stopped.

“If we don’t stop, I’ll have to fuck you right now,” she said.

I didn’t see a problem with it, but she was concerned that the maintenance crew might still be milling about in the building. We parted ways. I replayed it over on my way home and her voice came through my car’s speaker phone.

“I was so wet, I had to take a shower when I got home,” she giggled.

She had a date that night. It turned into a relationship, but that wasn’t stopping either of us.

A few weeks later, we locked eyes at work again and retreated to a classroom closet. She backed into me and rubbed her ass on my hard cock through my khakis. This time, she wore a blue thong. I saw it as I pulled her pants down a bit and fingered her while she kept her tongue in my mouth. She was dripping wet, but she pulled away again. The nervous energy took over with the fear of being caught a very real one.

Save for a few kisses here and there, nothing happened for the rest of August. Then, September came around. I was working in her office as was common practice for most of us. She walked in wearing a navy jumper and matching blazer. She removed her blazer to expose her arms. She and despite my experience from our previous encounters, she shared with me that she rarely wore underwear. Her office phone rang. She kept her eyes locked with mine and stepped between me and the desk. She answered the phone and straddled me. Other offices were bustling. Class was in session. She didn’t break her gaze. I was bold. I let my fingers disappear under her jumper and slide into her wet pussy. She loved it, but she continued her conversation without skipping a beat. She hung up the phone and I removed my fingers. She giggled and we didn’t talk about it.

There was another pause in our escapades. Then, a holiday break was on the way. We started making out in an office before the end of the day and then we entered the back seat of my truck. She got on all fours, working her hands quickly to unbuckle my pants. I reached around to squeeze her ass and finger her. Soon, her mouth was working my pulsating cock. I can’t accurately tell you how long it was going on, but I know it was quick. I came in her mouth and she happily swallowed. We parted ways and I felt like I had disappointed her. It was almost as if it never happened.

We pulled back yet again, this time for quite awhile. My relationship was falling apart and she was entering a new one. I was drinking a lot and she knew it. Then, my relationship crumbled. She shared being unhappy and unsatisfied. When I told I was a single man, she was ready to operate stress-free. She called me at 11 o’clock on the night that I told her my relationship was over. I found myself taking the short ride to her home and she greeted me at the door.

The silk remained. When we kissed in the doorway, I could feel her smooth skin through her pajamas. In an instant, we were making out on her couch. Her pants were off and my face was buried between her thighs. She was smooth with the right amount cellulite on her inner thighs. I had to reach up and keep my fingers in her mouth. She couldn’t scream because she took care of her elderly parents. She confessed that men her age don’t like to go down on women. Soon, I had her bent over the couch. I was deep inside of her. Watching her ass shake turned me on. She turned around and I was now on top of her, plowing her without a condom. I took off her shirt and watched her magnificent tits bounce. I was making up for the quick cum in the back of my truck. She was cumming, multiple times, praising me that I had a “nice cock” and suppressing her moans. I could see it in her eyes that she wanted to scream. I sat back and she got on top. Her riding while her massive breasts swung in my face will never leave my mind. She called out my name. She dismounted and started licking my cock, rubbing her tits against it.

“Do you want to cum in my mouth or on my tits?”

I took my favorite choice and exploded in her mouth. She washed my cum down with a can of Ginger Ale. We spoke for a bit after, laughing how we were both born in the wrong era. Now, we had unleashed a force.

A few nights later, we left a school function and made out in her car in the back of an alley. Her red blouse was open and I sucked on her nipples while sliding my fingers in and out of her wet pussy. The make out was sloppy and soon, I was grabbing the back of her hair while she devoured my cock. I came and we parted ways. My drinking continued and the early summer was starting to blur. I brought her back to my house in the middle of the afternoon.

“Open me up,” she was moaning. We went to dinner and then she rode my dick again in the backseat of my truck.

In my office, at the end of a long day, she hiked up her denim skirt and I pressed her against the wall from behind. She laughed at the cum dripping down her leg. One night, while I was working late, she walked in with a black sundress flowing. She blew me to completion and left.

Our last encounter happened at her house on the Jersey shore. I stopped there on my way to Atlantic City. She asked if I could help paint a small portion of her backyard fence and I obliged. Post-yard work, we moved to the bedroom. When we were completely naked, she dropped to her knees and slid her mouth over my cock. I noticed that she left her faux-pearls around her neck and that always stuck with me. I held out as long as I could and was sure to stop before embarrassing myself too soon. I threw her on the bed and ravaged her pussy with my tongue. Then, I turned her around and bent her over her dresser and rammed her from behind until she came. Now, she was finally free to moan as much as she wanted. She was admittedly afraid of waking the neighbors. After taking the pounding, she wanted to get on top. She laid me down on the bed and I noticed the full length mirrors of her closet across from us. My dick was hard to the point where it pointing toward my belly button. She got on top. I pulled her in and after moments of hot, dripping sex, I came.

That was our last official encounter. We tried a few months later, but we knew this would never be a relationship. We knew we had to move on and experience love elsewhere. She told me that if she continued this as a new affair, I could go home and forget about as if it were fun, but she’d still want more.

Source: reddit.com/r/gonewildstories/comments/b9u055/cougar_coworker_mf