The time I hooked up with the older co-worker [MF]

When I was 22 I was working as a machine operator at a manufacturing plant. I clocked in at 2pm and got off at 10:30. Us blue collar guys shared a break room with the office workers and that’s how I met Dianne.

She was 44, widowed, had 3 grown daughters and was already a grandmother. Physically Dianne was PERFECT as far as my tastes go. Average height, medium short brown hair, average size tits, but a HUGE ass. She was thick but not exactly chubby. Perfect. As far as her face goes, she looked a lot like a milf version of Mena Suvari.

After we got to know each other, I started flirting. A lot. And she rejected me. A lot!

After several months of me trying and failing, it was just me and her in the break room. She told me that the following day (Saturday) was her birthday. So I wished her an early birthday and asked if she had a hot date set up to celebrate.

My horny ears couldn’t believe what she said next.

“No, why? Do you want to be it?”

I somehow stammered out an enthusiastic “YES!” and we exchanged numbers. The plan was we’d meet up Saturday evening at a restaurant.

The next day I pussed out. I don’t know if it was nerves or what, but I called her and told her a family obligation had come up and I wouldn’t be able to take her out. Stupid, huh?

Thankfully, I got my nerve back a few hours later and called her again. Told her I was free to hang out if she still wanted to. It was already around 9pm so we couldn’t go out to eat, so I offered to bring over a movie for us to watch. She agreed, gave me directions and I was knocking on her door about half an hour later.

And we actually watched the entire movie! I never made a move. I’ve never been the most confident guy around women, and here I was inches away from my literal dream woman, and I was frozen.

She started drinking wine and once the movie was over, we headed to the kitchen to pop open another bottle. At this point we were both being kinda silly and joking a lot and at one point she gave me a slight playful slap on the ass. I think it was that slap that finally gave me the courage to make a move.

We went back to the couch and were just making small talk about gossiping about work when I finally said “I really want to kiss you right now”. She said that I should, so I went for it. What followed was one of the hottest makeout sessions of my life.

We actually made love to each other with our mouths. Slow sensual kissing followed by aggressive moaning kissing. Nibbling on each others lips. Sucking ear lobes.

She eventually straddled me and started grinding me thru my jeans as we kissed. I was finally able to unsnap her bra and pull her shirt up and suck her nipples. This went on for maybe about 15 minutes before she asked if I’d like to go to the bedroom.

Of course I said I would love.

She then told me that I can’t tell anyone at work about this. She swore me to secrecy. Which I also readily agreed to. She then took me by the hand and led me to her room.

Once in her room, the clothes fucking flew off. You know that feeling where ya’ll and kissing and undressing standing up at the same time? That’s exactly what happened.

Once completely naked, I laid her down on the bed. She looked amazing. Full body tan. And a bush between her thick golden thighs. She was actually the first woman I had been with at the time that had a bush. So, of course my face immediately went between her legs and started vigorously licking her already very wet pussy.

My mouth was on her pussy for all of 30 seconds before she pulled me up and told me to “just lay down.” I don’t know if it was my youthful lack of skill that caused this or the fact that she was ready to mount me (after our first time she told me it was the first time she had had sex in 4 years. I don’t know if this was true, but her reaction seemed genuine).

I laid down, she straddled me, and slowly lowered herself down on my ridiculously hard cock. What followed was one of the weirdest/hottest fucks of my entire life.

It was notably slow. There was no fast and furious fucking. She slowly and sensually rode up and down my cock. My hands were both cupping her huge ass until she grabbed them and place them on her tits. I started fondling and playing with her nipples and the first orgasm hit. Only being the stupid kid I was, It seemed to me at the time that she was in pain. I actually stopped and asked her if she was ok! Haha.

I can’t remember, but I think she came twice and finally I couldn’t hold it back any longer and shot my load deep inside of her.

She laid there on top of me for a while and finally got up and went to the restroom to clean up. She returned with a nice warm wet rag and washed me off. That was the first time that had ever happened to me as well. I remember it feeling so good.

Then I said “So this is kind of a dumb question to be asking at this point, but can you still get pregnant?”

She laughed and said no, she had had a hysterectomy a couple of years before.

We ended up fucking once more that night, missionary style, and then I went home.

We hooked up several times after this, but me being young and dumb, I was always trying to hook up with other women as well. I would show up at her place late at night and she would typically meet me at the door wearing nothing but an extremely thin nightie and lead me to her bedroom. Eventually she got more and more nervous that people at work knew and kept accusing me of telling our secret, which I hadn’t, so I eventually stopped going over there.

I still remember the last time we had sex, though. I mentioned earlier that she had a huge ass, and I’m definitely an ass man. We were fucking doggy style and due to my excitement and her wetness my cock slid out of her pussy during a thrust and landed on her ass. The sight of my cock, glistening with her pussy juices, laying between those beautiful ass cheeks was too much for me. I immediately came all over her ass. I remember thinking at the time that that was the hardest I ever came.

I quit a few years later and moved on to another job. Found out thru the grapevine that she got married to another one of our co workers who was her age.

Saw her a couple of years ago and she looks nothing like she did back then. Now she looks like you’re average 59 year old. But I’m not gonna lie…if we were both single I’d definitely bend her over again.

Thank you Dianne for making a young man’s dreams come true.

Source: reddit.com/r/gonewildstories/comments/bqfbor/the_time_i_hooked_up_with_the_older_coworker_mf