[Helen](https://www.reddit.com/r/gonewildstories/comments/6r8o55/alls_well_that_ends_well_mf_mff_update/) was pleased with the response [the last story](https://www.reddit.com/r/gonewildstories/comments/8on4m4/unplanned_unexpected_my_first_older_woman/?utm_content=title&utm_medium=user&utm_source=reddit&utm_name=frontpage) got, but disappointed with the story.
“Show, don’t tell!” she said “You left out most of an entire weekend!”. I was going to explain the importance of leaving the audience wanting more, but something happened that I want to write about later.
After that – I know…but I tease because I care – Helen sat thinking.
“If you’re not going to give people a blow by blow account you should tell them what happened the weekend after.”
“It was fucking,” I said. “More of the same, I’m afraid.”
“Gonewild Stories is full of that already and people don’t seem to be bored,” said Helen, “but is there anything you’d prefer to write about? And don’t put this bit in. It’s too meta.”
A couple of weekends after the first one, Jane and I were sitting up in bed and chatting. I was idly wondering where the day had gone, and Jane prodded me in the chest.
“That reminds me,” she said “my husband is home next weekend. Can I come to your place?”
At the time, I was sharing a house with three other people and it was one of those houses that people rent just after they leave University and live in while they take extreme measures to retain the student lifestyle they love while actual adulthood creeps in around the edges. In other words, it was a dump and – as the only one in the house with a non-minimum wage job – I was not proud to live there.
“Can we wait until I have a place of my own?”
She blinked at me.
“How long is that going to take?”
The answer was “more than a week”, so we kicked around the idea of meeting at a hotel half way between our respective home towns. Then I had a bright idea.
The Dirty Weekend comes from a time when there was stigma attached to sharing a bed with someone you weren’t married to. The idea was you’d go to a town where you weren’t known, sign into a hotel with your lover under an assumed name (because this is pre-card payments and you could get away with cash and “Mr. and Mrs. Smith”), fuck like bunnies all weekend and no one would be any the wiser. Of course everyone knew what was going on.
“A dirty weekend?” she giggled. “I’ve never been on one of those! Where shall we go?”
We spent the rest of the afternoon looking for a seaside town to stay in. Naked. With rewards for finding the most awful hotel (she won, I went down on her), the most rundown seaside town (she won again, and I massaged her shoulders) and the least possible beach (I won, and chose to keep my prize for later).
The following weekend, I met Jane at the railway station in her town, and we took a train to the coast. It was more or less the first time we’d been out in public together. I was all aglow with the pleasure of being with a beautiful woman, she was equally lit up at being with a guy she was into and we paid no attention whatsoever to some of the odd looks we were getting. It started to register with me on the journey as a couple of less civil people decided to pass comment where they could be heard. I was puzzled as to why anyone would have a problem with me holding hands with my girl, and slowly I realised that I’d stopped seeing her as being older than me. As far as I was concerned, age wasn’t something I thought about and it certainly didn’t slow her down. It came to a head when one particularly opinionated chap decided to ask
“Is she the best you can do, then?”
‘She’ was dozing at that point and either didn’t hear or pretended not to. I made sure I made eye contact with the guy – who was a couple of years younger than me – and smiled.
“At least I’m getting laid,” I said, and wanted to follow up with a stinging comment about his all male friendship group. But I couldn’t think of one that wasn’t going to piss off all four of them, so I didn’t say anything else.
I’d like to say that silenced him. It nearly did. He called me a couple of very rude names and gave me evil looks for the remainder of the journey. Luckily, we left the train before he did.
Strangers to the town, we got a cab from the station to the hotel. As I paid, the cabbie remarked that it was nice of me to take my mum on holiday. Uh-huh.
There was a giggly moment at the reception desk, introducing ourselves as Mr. and Mrs. Smith, but the receptionist just looked bored and we made it to the room without any further incident.
Once there, I kicked off my shoes and sat on the bed. Jane looked at me.
“We’re not spending the entire weekend in bed!” she said. I remember grabbing her hand and very gently pulling her towards me, nodding.
“Yes we are.”
She laughed, and gave me a look that was part amusement and part lust.
“But we came all this way! We’ve got to get out and see the sights some time!”
“No we don’t.”
She dropped to her knees, ostensibly to look me in the eye. As she did so, her hand brushed over my groin. She paused, explored more deliberately. She unzipped me, and smiled.
“Well,” she said, “not right away.”
I don’t know if I’ve said this already, but my experience with blowjobs was limited to a couple of experiences that were, in retrospect, grim. But you know what they say about oral sex – even when it’s bad, it’s still good. To be fair, I was comparing these to my first ever…ah, but that’s a story for another time. Anyway, Jane put them all in the shade.
Jane loved my cock. I sat on the edge of the bed while she kissed and stroked it, licked it, nuzzled it, engulfed it in her warm mouth and generally made a real fuss of it. She liked to stroke it with just the head between her lips so she could alternate between kissing the head and swirling her tongue around it. She would do this while I tried to strike that balance between enjoying the experience and not cumming almost immediately so there was an experience to enjoy. She seemed determined to make me cum, and had me right on the edge of exploding in her mouth…and then she stopped. I think I may have said something witty and manly like “uhhhwhyjastopthen?”, which was definitely not said in a sort of desperate falsetto, and while I was recovering my scrambled wits, she stripped.
Any other time, I’d have stroked my cock while I watched. Not this time. Besides, it was a very utilitarian strip, with no tease involved. She just wanted to get naked as quickly as possible, and she did. So quickly that I’m not sure I saw what she was wearing under her clothes. If she was wearing anything. What matters is a few seconds later we were both on the bed making out while she avoided touching my cock and I deliberately didn’t avoid touching her anywhere. Her body was still a novelty, I was still finding out what made her feel good and what made her feel great, so I always took the opportunity to touch and taste whereever I thought she might enjoy, and this always included time with my tongue on her clit. She loved it, even though it always reduced her participation to soft cooing noises by way of encouragement. If I did the right things, the cooing would become very earthy moaning and then there’d be an orgasm, and I got to feel smug and proud that I’d got my older, experienced lover off in no uncertain terms.
This time, though, she stopped me just short of that point and got on all fours, wiggling her arse at me. I got behind her, and maneuvered my cock to her pussy. Doggy hadn’t always worked well for us, but we persisted because it was a favourite of hers. I had a lingering ambition to make her cum that way, so any time she was in the mood to try then so was I. This time, I remember sliding into her and feeling that it would be THE time I’d get it right. After a few false starts – which just meant I got to penetrate her (always a highlight for me) a couple of times – we seemed to have found a rhythm and a timing that kept my cock in her and hitting some of the right places. Because I was concerned with doing it right and doing a good job, I sort of forgot about my own level of pleasure – until she started shaking and collapsed on the bed. She turned over with a huge smile on her face and dragged me down for a kiss. No mean feat for a much smaller person. A few moments after that I was back inside her, with her urging me to do whatever I wanted to.
You should know me by now (and if you don’t, well…that’s what post histories are for), so it should be no surprise that I chose to cum inside her, much to her appreciation.
We did stayed in bed – because we both wanted more – for a few hours and eventually stirred ourselves to shower and dress so we could go out to eat. There was no sexy teasing at the restaurant, we were both pretty hungry and in that oxytocin glow where all you want to do is spend time with your partner. Where the world disappears, with the exception of waiters, and everything you say is charming and funny.
The following day – yes, there was a bedtime fuck and yes, I’m skipping it because we were still in the stage where even getting undressed around each other was a cue for something sexual, so although it was a lot of fun there’s more to tell and you want me to get to it – we actually did sightseeing.
There was a beach that we walked on hand in hand, although being in Britain it meant there was a lack of tropical sunshine and palm trees, no sign of a beach bar and the only cocktail to be had was tea, milk and sugar. There was an aquarium, where we earned disapproving looks by sneaking off into a dark corner for a kiss. There was an amusement arcade where Jane kicked my ass at Tekken something or other. We ate lunch, and we went for a walk along a shore path that went from pavement to greenery to a bit of a nature ramble. The weather was good, the view lovely and all seemed right with the world. After ambling on for a good thirty minutes, we found somewhere to pause and take in the view. Which didn’t last long, because hand holding turned to kissing turned to making out. We tried to find a more sheltered spot, but couldn’t and so walked further.
Anticipation gave us a little kick of energy and we eventually found somewhere off the path where we were out of direct view of everyone and everything. Jane was wearing a pale yellow sundress and I fully expected to find nothing underneath it. I was not disappointed. Having established this, and having had her dioscover that I was hard, she straddled me and sank down onto my cock. Outwardly, we appeared fully dressed. With no real reason to go quickly, we made our movements slow and small to start with. We kissed, touched and talked about what we were feeling and how much we were enjoying each other, which made for a very hot afternoon’s sex. Eventually, though, the sensations and the feeling of closeness were all a bit too much and we reverted to type: fucking like bunnies because it felt so good.
That night we had a romantic meal, hung out near the shore as the night drew on, and eventually retired to bed for a protracted session of kissing and touching that ended with the pair of us drifting pleasantly off to sleep in one another’s arms.
The next day – the last of our little holiday – should have been all about getting ourselves together and going home. Instead, it started with a surprising question. Jane stepped out of the shower, where she had been for a considerable time, wrapped herself in a towel and sat on the bed.
“Would you like to try fucking my arse?” she asked, in much the same manner that you might ask someone if they’d like to try a local food delicacy. I didn’t know how to answer.
I was pretty inexperienced in some areas. I’d never been with anyone who wanted or enjoyed anal, at that point, and had no idea how to go about it. I said so, because the idea held a certain attraction. Let’s face it, if your partner makes an offer, you have to assume that they’ve done it before and liked it, or they know you really want to. In this case, I’d never mentioned it. But she had, and now it looked like the moment had arrived.
“Yes, please,” I said. Jane gave me a big smile.
“How about now?” she asked.
What I learned from the 20 minute debacle that followed was: just because your partner is enthusiastic, it doesn’t mean they know anything about what you’re attempting; everything works better with lube and some things do not work at all without it; just because your partner is older than you, it does not follow that they have any more experience than you do and they may not have done this before either; the prospect of a thing can be way more exciting than the reality of that thing.
Suffice it to say that Jane offering me her arse was one of the most erotic things she did for me. But me taking it came a while later after a lot of serious thought and research.
Reality returned on the rail journey home. We parted at the station, aching for just one more fuck but unable to find anywhere to make that happen. We kissed the time away between our arrival and my train home, and that was the last I saw of Jane for a month or so.
(Helen is amused that I’m apparently displaying feelings “like real people have”, and she’s very proud of me. I don’t know whether she’s genuine or is mocking me for being sentimental, which is just one of the things I enjoy about her. There are several other things I enjoy about her, and since I’ve finished this story, I get to go play with some of them.)
Source: reddit.com/r/gonewildstories/comments/8s8zd7/a_weekend_with_my_fantastic_older_woman
Wait, so this chick is ugly?