Unplanned, unexpected, [m]y [f]irst older woman.

I have to give a shout-out to u/helenintheuk_secret who is partly responsible for two things. Firstly, her recent posts have piqued the interest of my partner, Helen (I’m pretty sure they’re not the same person) and, full disclosure, resulted in some very pleasant sex for me. So thank you for the excellent writing and the inspiration, u/helenintheuk_secret – please keep writing! Secondly, it’s nudged my partner to nudge me and say “Why aren’t more of our exploits on Reddit?”

My answer to this was the wrong answer, and so I’m writing a couple of things up but, following a conversation about potential content, this is what Helen wanted me to write first.

Backstory: I was with a girl, and we were starting to get serious. In our first year together, she missed my birthday because she had a pre-existing thing to go do. I understood, and gave her a year’s notice that I wanted her around for the next one. She told me she’d do that.

11 months later I’m organising a night out with a few close friends to mark another year of not being dead and she announces that she’s going to go see some friends, like she’d done the year before. I object, pointing out that she’d had a year’s notice to not make those plans, and I got told “sorry, dude, but you know how it is: bros before hoes”. Not literally, but that’s the gist of what she said.

So that was the end of that relationship.

I cancelled my plans and intended to do something entirely self centred instead, but was stuck for an idea. Then one of my online chums came up with an idea – I should visit her and we’d do some geeky history stuff in her locale instead. Getting away from home, and meeting an online friend seemed like a good idea, but dear reader I know your spidey sense is already tingling. Well, here’s why mine wasn’t: the lady in question, who I knew as Jane, was married, twice my age and a member of a forum for folks interested in all things historical and archeological. We were chums, shared jokes but never flirted and I assumed I would be entirely safe in her hands.

I took a train to her town, with the intention of meeting her at the station. I remember being slightly nervous, because it occurred to me only belatedly that I had disappeared to a strange town to meet someone I didn’t know and hadn’t told anyone where I was going. I had no idea what the woman might be like, and no idea whether this was a good idea, and equally no idea what I might do if she turned out to be a maniac or vastly different from her pictures. We’d exchanged pictures, so we knew who to look for at the station, but this is back in the day and hers was a scanned photograph, whereas mine had at least been taken with a digital camera. Our phones were as dumb as I was.

Why didn’t it occur to me that something might go wrong? In all honesty, a healthy dose of male privilege and a sort of physical confidence. I was – still am – 6’2″ tall, broad at the shoulder and at the time quite physically imposing. I was also habitually dressed in a black leather jacket, jeans, boots and had long hair. People very rarely confronted me about anything. I was scary lookin’.

I left the railway station and spotted her pretty much immediately. She had shoulder length ask blonde hair and was wearing what I can only describe as a silk trouser suit in a camoflauge pattern designed by an interior decorator who’d had his morning latte spiked with acid. Various alarms went off in my head, because the word “hippy” was marching towards my day with ill concealed haste. I walked over to her and was struck by two things. First, she didn’t look her age. Before you’re 25, you think of 30 as past-it and 50 as old age. She looked like she was in her late 30s. It might have been the light on her skin, the smile that appeared when she saw me or the confusing disruptive pattern of her clothing, but she seemed like a much younger woman. Then she hugged me, and I did the one thing that I wasn’t expecting to do: I kissed her.

I hadn’t started off intending to. But I did. It was a proper kiss, too. I devoted all of my attention to it. You hear people talk about being “in the moment”, and I heartily recommend it when you’re kissing someone you’ve only just met. After what seemed like a very long time, she broke away and I could see she seemed a little taken aback, but there was definite delight in her eyes. We grabbed a cab, making small talk in the back as it drove out to the suburbs, and she never once let go of my hand.

The front door shut behind us, we went up the stairs still hand in hand and walked into a bedroom. Without saying a word, we stripped and, naked, kissed again. She almost threw herself at me. She went from quiet and slightly demure to hungry and demanding.

I learned several things in the space of a couple of minutes. The first, and most surprising, was that age doesn’t happen equally. She carried most of her age in her hands, but from wrist to neck she had the body of a very much younger woman. Her skin was porcelain and flawless, her small and beautifully formed breasts perky and crowned with deliciously hard nipples. I entirely forgot there was any sort of age difference, because I was paying a great deal of attention to the fact that a naked woman was looking at my body with outright, unashamed desire.

I’ve never got used to that happening.

Her hands were everywhere, from my neck downwards, exploring and caressing as if I were something special. Like she’d never had her hands on a man before, and wanted to etch the experience into her memory. For my part, I was content to touch and stroke whatever part of her I could reach without getting in her way. I hadn’t been expecting this, and now it was happening I most certainly didn’t want to spoil events with my relative lack of experience or over-eager fumbling. So I did what I thought was right, matched her pace and passion without getting impatient or trying to push things on towards penetration (which was what I wanted, because honestly I was a little nervous she might come to her senses).

There was more kissing, and then we were on the bed and I was on my back as she kissed lower and lower, her hair tickling my skin and forming a blonde curtain as her lips arrived on my abdomen.

Then she touched my cock, which twitched, and she giggled. That was a bad moment. All the “am I big enough?” inescurities rear their ugly heads, and just for a moment I could imagine things ending right there with laughter and diplomatic attempts at letting me down gently. Instead, the next thing I felt was my foreskin being pulled back slowly and gently, and a soft kiss right on the head of my lots harder penis. If I hadn’t been distracted by angst, I think I might have cum on the spot. It wasn’t the prelude to being sucked, it was an actual tender kiss.

A moment later, we were face to face with her hand wrapped around my cock stroking it slowly. She was grinning from ear to ear.
“Oh it’s beautiful!” she said.
A day of surprises continued, because I’d heard women say all sorts of things about my cock before but it had never been called “beautiful” (and hasn’t since, although has been called a “goldilocks cock”, which derailed the sex we were having until it was explained – and you can work it out for yourselves). I said something about being glad she liked it and she kissed me very deeply and, when she was certain I was thoroughly kissed, solemnly informed me that she was going to take my cock in her mouth – a thing she hadn’t done for anyone in a long time – because she wanted to experience it everywhere.

What followed was something I’d hesitate to call a blowjob. I think the best way to describe what happened was that Jane made out with my cock. There was much stroking and kissing, licking, sucking, touching and teasing. It was a lovely experience, but got me no closer to cumming than when she started. About half way through I realised that her goal wasn’t to get me off, she was having fun. And I wasn’t being requested or required to do anything but exist and be made a fuss of.

In another context, or on another occasion, that wouldn’t have felt right. At the time, I felt like the most important person in a very small world, so I let her play and explore until she was content. She made her way back up my body until we were face to face and she kissed me again, then asked me if I could taste my cock on her lips. I couldn’t – because, frankly, hygiene – but there was a decidely impish look in her eye, so I told her I could and she went slightly mad with the kisses and also started stroking my cock with new determination. Then she, with no warning and with surprising speed, mounted me and – there’s no nice way to put this – fucked me. She came pretty quickly, and I was under no illusion that I had anything to do with her orgasm other than being there. When she stopped shaking, she informed me in a very matter of fact way that she hadn’t had sex in quite a long time and was incredibly happy to feel something inside her again. I asked whether there was anything she needed from me, and she nodded, grinned, and started moving again.

This time, I was allowed to make more of a contribution. In fact, I was positively encouraged to match her movements and her passion. We both got very vocal, she had another orgasm and then I realised I was about to cum too. I told her this and she said “good!”, wrapped herself around me, gripped me with hands, thighs and a bunch of internal muscles and then kissed me as my own orgasm arrived.

Afterwards, having visited the bathroom, we lay side by side in the bed holding hands.
“I really didn’t think that through,” she said “I really should have been more sensible. But it was so lovely I didn’t want to stop.”
Uh-oh.
Here’s the thing. I hadn’t planned on sex, so I wasn’t prepared. I think there might have been a condom in my bag somewhere. Had I thought I might get laid, I’d have stocked up on my way over. And from this admission, I’m pretty sure she hadn’t planned on sex either. We looked at each other. She giggled, which in all honesty I didn’t think was an entirely appropriate reaction. Plus, I was trying to find a way to ask her whether she was pre or post menopausal without sounding like a total arsehole. I gave up, because it’s not possible.
“Oh well,” she said, “que sera sera. We’re probably fine, but just in case you’ll have to cum in my mouth for the rest of the weekend.” She thought for a moment. “Or in my arse” she conceded.
I shrugged.
“Where ever you want” I said, which met with approval, but what else was I going to say?

We spent the weekend in bed. We tried not to, but that only resulted in us fucking on the kitchen floor and the sofa. No one had really appreciated her body in a long time, so she wasn’t going to pass up the opportunity to have as much sex as possible, and I was an entirely willing participant in this venture, still in a little shock that an attractive woman twice my age would find me worth fucking.

We parted at the station.
“Make sure you buy condoms,” she said, kissing me again.
“Of course,” I said, “when for?”
She gave me a look.
“Next weekend. I think there’d better be a next weekend, don’t you?”
“Yes,” I said, “absolutely!”
“Good,” she said, “I’ll be better prepared for next weekend. Really put you through your paces.” She winked, and waved me goodbye.

Dear reader, a week has never passed so slowly.

Source: reddit.com/r/gonewildstories/comments/8on4m4/unplanned_unexpected_my_first_older_woman