I'm using the term "MILF" loosely here, but the last story inspired me.
>Some years ago
>Start trying to find people to hang out with on a social networking site, finding myself gravitating towards older women a bit
>Find a woman in her late 40s who's already a grandmother, a bit rough around the edges lookswise, but that's alright, I still find her pretty personally
>Also a bigger lady, but I'm into that
>Happens to be one of the sweetest ladies I've ever talked with
>Over time, our conversations start to turn flirtatious
>It turns out she has a very sexual side to her
>Eventually end up shifting to emails that I have saved to this day
>By this point in time, we're basically flirting with each other outright
>She decides to send me some naughty pictures, one of her in lingerie, another of her nude, but covering herself with a teddy bear
>She eventually decides to get rid of the teddy bear
>My eyes pretty much can't get off her naked body
>She gets an eyeful of me as well
>She thinks I'm super sexy
>We continue sending each other naughty pics
>As it turns out, she wasn't far away from where I was at the time
>Try to make a meetup work, but things don't fall into place
>Fast forward a year or so, things finally end up lining up
>Get mildly lost on the way to her since I wasn't using a GPS at the time, but eventually find my way to her address
>Said address brings me to a broken-down shed, start to get nervous
>Ask her if she was actually there
>She said she was
>I apparently didn't notice the house next to it, which only had a back door
>See her standing right outside it
>Feel a sense of relief relief wash over me
>She was in a normal dress, I was in T-shirt and shorts
>We go inside her house, and make our way to her bedroom
>Her room is actually well-organized, which is a huge plus for me
>Move to her bed
>She asks if I want to watch anything
>Turn it down and just get to cuddling with each other
>Caress each other's bodies, my shirt ends up not lasting long
>Hers ends up going off as well, followed by her bra
>Move my hands all over her exposed skin, enjoying the softness that big girls have in abundance, while gazing into each other's eyes
>Her hands are exploring my body as well
>Eventually end up with me in just underwear and her in just panties
>Start grinding against each other, she's very clearly enjoying my hardness rubbing up against her
>She starts to get very worked up
>Grind against her ass
>She starts massaging my dick with her ass cheeks
>Ok, this woman knows what she's doing
>Almost end up nibbling her neck, but before I can, I prematurely ejaculate a bit
>Excuse myself and get a tissue
>Takes off my underwear, revealing my full manhood to her
>Cum inside of the tissue, watching her closely as I do so
>There was that part of me that felt like she really wanted me deep inside her at that moment, but I wasn't ready to go quite that far
>Go into the bathroom really quickly to pee out any remaining jizz backed up in me
>Come back, snuggle a bit more
>She admits to me that if I ended up nibbling her neck, she would have fucked me, no questions asked
>Put clothes back on and go our separate ways, as she had more plans to visit relatives that day
>Continue flirting for a good year and a half, even though we'd end up quite a distance from each other some time after that day
>She gets weight loss surgery, last I checked that whole process was going well for her
>Ends up finding a guy, our conversations unsurprisingly end up tapering
>End up messaging her over a year later to see how she's doing, apparently the relationship ended up working to a point where she was going to get married a few months after the conversation
>Haven't heard anything from her since
Sucks that we only got to see each other once, but I'm glad things ended up working out for her.