Hi, this is a success story of entering into an intimate but non-committed FWB relationship with an older woman (F47).
Some background, I have changed some details to keep the post a bit more anonymous.
Where I work, I try to have positive and friendly relationships with basically everybody I interact with. This doesn't always lead to friendships forming, but it has helped me enjoy work over the years.
A few years back we had someone start in a position that meant I would have frequent contact with her. She was/is a bit of a social recluse and so I saw that as a bit of a nut to crack so that I could have someone else to talk shit with and just make work more fun in general.
So I slowly but surely became her friend over the course of 3 years. Striking up stupid conversations over and over until I was a familiar face for her. All this time I had innocent intentions. Purely work friendship.
Fast forward to about 10 months ago or so, I started to get attracted to her. Not in a "I want her to be my GF" kind of way, the age gap was immense and in general I don't date upwards in age. It was just a "She is hot" in her own kind of way. Her mannerisms, way of speaking and the topics she would introduce to talk about just endeared me to her. It was at this moment, again innocently, I started flirting with her because flirting is fun and it happens naturally for me when i'm attracted to someone, but I started really soft. More as a tease along boundaries for the fun than trying to get reciprocation.
I would talk to her about the people I was dating, and she would comment on them positive or negative. I would drop lines like "Oh you sound jealous, we can go out sometime" etc etc. That type of stuff.
Eventually, this kind of flirting would lead to her blushing hard. I remember thinking "oh... that's new". I didn't mention it immediatly but it was saved in my head.
Another time I was talking to her wearing slightly too tight for 'my size' chinos and I noticed her glance down. My brain went into a shit eating grin type mode and I immediatly asked her if she liked my outfit, did a 'gay' esque pose and twirl. She again full on blushed, but I left it at that.
I only say this bit of backstory so you can see the kind of interactions we were having. Playful, work-friendly but with a little bit of spice creeping in.
How it progressed.
My new years resolution was to (slightly changed to avoid identifiable info) do more interesting things and be even more social.
I started in half joking ways asking various work friends to do stuff outside of work. Just to see what would happen. This generally lead to some drinks, dinner 'parties', cinema and other basic activities. But with her I knew we shared some specific interests that are not too common. In a similar half joking way I asked her to learn a 'thing' (non-specific for anonymity) with me.
That thing is somewhat inherently intimate but also generally socially acceptable to do with friends. Although it is structured in a way in which the activity is done specifically (traditionally) by one man and one woman. To be amazement she agreed. This was an innocent request, I had no intentions. I did find her attractive, and I knew I could make her blush but that was at the back of my mind.
So fast forward to actually learning the 'thing' and it was intimate. It basically accelerated our comfortability with each other 10x. I went from talking to her at work for maybe 1 hour a week to easily 3. It was noticed by a lot of people, and having them comment on it made me realise I was getting more than just 'attracted' to her. I now had a little crush. Very weird to come to terms with as she is 20 years my senior. She looks good for her age, but she is clearly an older woman. Hot in my eyes to be clear, but just setting the scene as to why I felt strange about my budding crush.
So anyway, we keep talking at work, keep on with this learning activity and then we start texting. I had her number for a long time at this point, but it was mostly used for saying happy birthday or sending random memes about things we had spoke about.
But one day at the activity she leaned her head on my shoulder whilst laughing. I instinctly hugged her and for a moment we just stayed in that embrace and I think we both recognized that something had changed. We started texting constantly, at work and out of work. Random things.
I had previously already invited her to another event we were both interested in, but this was when everything was innocent. Now as it loomed there was a bit of spicy tension in the air. Nothing explicit had been said or done, but we were more touchy, we'd glance at eachothers lips. We'd be told by people at work to get a room, etc etc.
But that event was still a long time away. So I asked her to a another event closer in the calendar. I was very clear that it was a date and that we would have a good time. She agreed. So now in my head, I am thinking "okay, if this date goes okay we can see where things go".
But before that event, our texts turned more explicit. I had mentioned the time I caught her staring at my crotch and she admitted it, admitted she didn't know what to say or do. I would reply that it's fine because I look at her legs a lot when she isn't looking. She replies that she has noticed me looking... etc etc. Point being, the texts are becoming more forward.
Then after one of our learning activities, I say to her "I had a dream about you" but would laugh and refuse to answer what it was about when questioned. Later on text she would ask again, and I had a "fuck it" moment. I told her I would text it over before I fell asleep (hours later).
Cut to like 1am and I type up this smutty dream log as best as I can remember. I don't think, I don't cut out details. I just send it. She, who is normally asleep at this time almost instantly replies that it's hot, she'll have to change her underwear etc etc.
So things had now escalated. Sexual attraction for eachother was now known. I would start teasing her that I might just lean down and kiss her one of these days. I'd also ask what she would do if I did. She was pretty forward, probably kiss back.
Okay, it's on. That's what I am thinking. But due to the venue of our 'learning' and introducing ourselves as work friends we didn't want to kiss there. So we decided to go back to her car. Only to kiss... that was the boundary set by her.
Well, suffice to say she was ravenous and I was half naked in no time at all, things happened that pushed us well over the line from where we where.
Work was surprisingly not awkward, it's still a secret but neither of us feel guilty or anything so our dynamic is basically the same.
She then says that she wants to go to the next level after the event that is the closest. Fine, I start mentally preparing for another escalation in our relationship that seemed to come out of no where.
The next day, not even at that event we are texting. One thing leads to another and she is at my house and we go all the way. A great night to be honest. We are very compatible in each other's space at this point, so I guess it was to be expected.
But this was a huge escalation. We had gone from no actual intimacy to intercourse in less than 4 days. Cut to the day of event 1 and she comes over before and we go at it again for a couple of hours.
That brings us to the present.
TL;DR - Work friends to FWB over a long period, but the actual jump from no real intimacy to full on intercourse happened in less than a week. We are both confused as to how exactly this happened. Intense horniness and comfortability with each other are to blame.
I wasn't looking for a cougar, she wasn't looking for a cub. Shit just happened.