Unwittingly fulfilling a MILF’s fantasy on holiday [FM]

I’ve been living vicariously through you guys for a while so I thought I’d chip in with a tale or two of my own. Had this throwaway for a while and as I’ve got a day off I’ll try to write this up … first time so excuse any mistakes. This happened a couple of years ago, and for those looking for a marathon shagging session I apologise in advance .. this is 95% build up.

I’m male, Scottish, mid to late forties and divorced. I have a school aged boy with split custody … a few days midweek and every other weekend, but the ex-wife had recently been away so I was owed a week to myself. It was getting into the dark, cold autumn nights and mornings and I fancied a few days in the sun before winter properly kicked in. Sand between my toes, sun on my shoulders, cold beers and no commute to worry about in the morning.

I mentioned this at a meeting with my managers on a Friday afternoon and they started reeling off dates I couldn’t go away as I was needed for this project and that event, so asked,

“Well what about next week?”

They paused, looked at schedules and said.

“Well as long as XX is done and you have cover for ZZ that should be fine.”

Rush back to my desk, finish XX, arrange cover for ZZ, hit up the cheap flight and hotel sites and two days later on the Monday (was too late to arrange weekend cover for the boy so he spend two days kicking my ass on the PS4) found myself stepping out a taxi at the entrance to a self catering complex under the gorgeous early evening sun on the island of Lanzarote.

The layout of where I was staying is important to the story. The place had maybe twenty apartments, all bungalows, laid out on two sides of a triangle with a communal pool in the middle, and on the third side the pub and offices. Well, I say pub, it was three walls, a roof and a shuttered front with tables and a pool table that were moved outside in the mornings. Each apartment was set back from the next and had a private patio with walls on both sides to give some privacy from next door. Each patio opened out onto the pool area which had some palm trees and shrubbery to give a bit of shade. It was a nice place where you could laze around in relative isolation or join others by the pool.

I arrived early evening, got checked in, examined my apartment, and checked out the local pubs along the beach front, stumbling back later with some mystery meat in bread at an undetermined hour.

Got up the next morning craving water and coffee, so threw on last nights shirt over my swim shorts and stepped out in the blinding light. When my eyes adjusted there she was.

Her name was Fi (well it wasn’t, she was Irish and the way her name is spelled and the way her name is pronounced are two very different beasts, so we settled on Fi … pronounced fee) and the only word I could use to describe her was petite. Five foot nothing, long black hair tied up in a ponytail with an almost-but-not-quite skinny body and tiny tits in a small back bikini under a black see through cover up, open at the front. A touch of the Romany, so although she had pale skin there was a touch of Eastern European to her look… dark eyes and high cheek bones. She was mid-thirties with one or two miles on the clock but still smoking hot, with a beautiful oirish accent, quick smile, and as it turns out a bit clumsy in really a cute way.

She was laying a towel on a sun lounger and setting out a few things like water and sunscreen before she noticed me, and here’s the thing, she was on my patio. At the edge, but still very much on my patio.

“Oh shit! Sorry! There was no-one here yesterday. I’ll move.”

“Don’t be daft …It’s fine, best place for the sun just now. Besides I’m here on my own, be nice to have company.”

“No really, I’ll shift.”

“Up to you but I really don’t mind. Anyway I’m off to the shop for some stuff do you want anything?”

“Eh, no, I’m okay”

But at that, in her flustered state, she kicked over her bottle of water, spilling it’s contents.

“So, you’ll be needing more water, be back in a bit.”

I jumped up on a small wall to get past her as she laughed and I headed off.

I get back about twenty minutes later and she’s gone, but some of her stuff is still there, so I leave the bottle of water on her sun lounger and head inside for a shower and breakfast pastries.

I should describe myself, and the most apt word is average. Average height (for Scotland at 5’8), a bit of a dad bod, average cock about 6 and half to 7 inches … depending on how far I can press the ruler into my groin! … and okay looks. I do however always have a bit of scuff, long hair (at the time), blue eyes and a cheeky smile with a dash of confidence, so I do okay despite being a wee hairy guy.

I appear ten minutes later wrapped in a towel to have my coffee in the sun and she’s back, and looks, I don’t know, shinier than she did earlier. Hair is now down, there’s maybe a touch of make-up and she’s a bit more … together.

“Thanks.” She says with a laugh, holding up the water.

“No worries, got to stay hydrated in this heat.”

“So what brings you here …”

And so starts a lovely, long, slow conversation that lasted for the next few hours. It was roasting under that sun and too hot to be an animated chat, but between dips in the pool, pages of our books and at lunchtime a break for a toastie from the pub, we laughed about the fact that even in our 30s and 40s we must be the youngest people there by quite a few decades … and in the course of the next few hours covered my divorce, her separation, jobs, hobbies, kids, and as the after lunch beers kicked in, kinks, dating stories and other flirty stuff. We even talked about tests and birth control.

I went from wondering if we were going to fuck to wondering when we were going to fuck.

She was here with her pal who was off in the main resort town trying to hook up with a guy they had met last night, so Fi had thought fuck it and wanted a day of peace and quiet … and she’d picked the right place. It was peaceful.

There was the sound of a music channel drifting over from the empty pub, the occasional snatch of conversation from another far away patio, and a bit of whistling from an older man sauntering around with a hose watering the greenery. Other than that just was the noise of a gentle breeze in the palm tree tops and the lap of the water in the pool. Peaceful.

We got onto tattoos and piercings and turns out she had one of her nipples done, as had I. The difference was that I’d taken mine out after bashing it against too many door edges or catching it in clothing. She’d kept hers in and said she didn’t mind the odd surprise bash or pull as it “gets me throbbing.”

This was my cue for a dip in the pool. This was fast becoming a running joke, anytime we got just too flirty or getting hot and bothered, one or other of us would go and jump in the water. I got out after the nipple chat and saw she was applying sun cream to the pierced side, hand inside her bikini top and looking me in the eye. My jaw dropped and I turned and jumped back in, hearing her giggle in the back ground.

Now, if the day had ended there, I would’ve been happy. We’d spent a lovely day together chatting, flirting, playing with things like ice cubes on backs, splashing water, drinking beer and generally really enjoying each others company, but it was about to shift up a gear …

On climbing back out the second time, I said,

“You know I could put that on for you?”

“Oh yes please.” Holding out the bottle of cream for me.

“Now do you want it rubbed on, or do you want it (stupid drawling voice) rubbbed awnnn.”

“Oh the second one.”

“OK, lie down.”

She lay on the sun lounger on her stomach, arms under her face and I squirted a big line of it down her back and across her shoulders. She reached back and undid the string strap of her bikini and lay back.

“Wouldn’t want to get it all oily”

So the first time I touched Fi was to lay my hands on her shoulders and start to slowly … sensuously rub cream into her. I moved her hair to the side and gently caressed it into the back of her neck, working down her back and sides. Taking my time as I was enjoying her little sighs and moans.

As I got to her sides she had a furtive look around and propped herself up onto her elbows whilst clearing her throat. I took my cue and slid my hands round to massage those beautiful tiny tits and hard nipples, making sure to give a little tug on the one with the bar which got a little gasp. This was on.

The guy with the hose was wandering back our way, and even though we were protected by the walls either side, anyone could see what we were up to from the front, so she lay back down as I got to her lower back and ass. I massaged her ass cheeks slowly but was forming a plan … I squirted a big line of cream along the backs of her legs, and starting with her right leg, massaged the cream into her skin from her foot up. I went slowly up her calf and over her knee, then started on her thigh. My right hand was doing all the work, massaging and rubbing while my left hand was doing nothing but inching up the inside of her leg, getting closer and closer to her pussy. Her moans and gasps were more audible now and I had to discreetly shush her as my fingers got closer and closer. My right hand was on her ass, massaging, rubbing, pulling her open and was sure I could hear how wet she was getting. My fingers were so close to the edge of her bikini bottoms. Inching nearer and nearer … and just as they were about to touch …

“Right, other leg.”

She shot me a look and mouthed ‘oh for fucks sake’ but with a naughty annoyed smile.

I spend time on her left calf, over the knee, then oh so slowly up her thigh. Left hand massaging, right hand trailing up her inner leg. Inching slowly towards her pussy again as her legs opened wider. Getting higher and higher. My left hand on her ass cheek, the fingers of my right had almost reaching the material of her bikini. She raised her ass slightly for better access. I was getting closer and closer and closer. I could really hear her wetness now, smell her arousal on the air. I could feel the heat from her cunt.

I had a look around. Still so peaceful. The pub had switched the music channel for a football (sorry, soccer) game and the occasional muted roar of the croud or snatch of Spanish commentary could be heard on the breeze. There was the odd voice from here and there and the guy with the hose was whistling away at the far end of the complex. Rustling of palm leaves, gentle lap of the pool. If it wasn’t for my brick hard cock and her heavy breathing I would have called it relaxing, As it was we were in our own discreet little frenzy.

Now here’s how I thought this would go down. I would make a sort of finger gun shape with my thumb on her asshole and my finger tracing the length of her pussy, fingertip caressing her clit. I may have done that for a few moments before discreetly pulling her bottoms aside and sliding a finger or two inside, and when we couldn’t take any more we’d gather our things and disappear into my apartment for some fun.

Nope.

In a surprise to everyone involved, the second I made contact, she came. Hard.

The OOOOOOOoooooo was so loud it fucking echoed.

Her legs that had been languorously lying open snapped shut trapping my finger and thumb so I had to pull hard to get then out … in doing so I blundered backwards into a few of the empty beer bottles we’d accumulated, sending them in all directions, and almost fell. It was lucky I managed to control my decent into sitting on a small wall and I think I said something like,

“Yeah, I told you that was cold.”

The place was silent. Hose man was looking our way, the TV in the bar was off or muted, and all conversation had stopped. The only noise was someone coming down from a big orgasm in a very vocal way. There had been little yelps earlier as we played with ice cubes, but none of those had ended up with her in the fetal position, saying fuck a lot in between loud giggles, her hands closing into fists and opening wide. Then a head popped up from the patio next door! Don’t know how long he’d been there or if the old fucker had been listening but he said,

“Everything okay?”

“Yes, just too much sun and maybe putting a cold bottle on her back wasn’t the best idea. I’ll get her inside.” I helped her up, wrapped a towel round her and led her shaky legs to the apartment.

The apartments were all laid out the same inside, living room with futon, TV and open plan kitchen leading to bedroom and bathroom at the back. We got inside and I started to lead her to the bedroom, and here’s where it took a bit of a weird turn and we get to the unwitting fantasy fulfilment. She pushed me away as I went in for a kiss and said,

“Couch. Naked”

“… but …”

“COUCH, NAKED … fuck I think I’m still cumming.” she steadied herself on the TV stand and bent her leg at the knee.

I stripped off my shirt, pulled off my damp swimming shorts, and sat down, erect cock standing proud.

“Schooch your arse forward a bit and lean back”

I did what I was told as she pulled the string on her bikini bottoms and let them fall revealing a beautiful pussy with just the hint of a landing strip. She walked over and stood with her legs either side of me, leaned forward and put her hand on my shoulder, pushing me back against the couch. She knelt up on the couch, hovering her pussy over my cock and whispered almost to herself,

“Oh fuck it’s happening”

With her free hand she guided me inside her and slowly lowered herself onto my cock, then took her other hand and pinned my other shoulder. Oh she was tight and wet and hot, and making this moment last. Sliding down and up slowly, each time taking more of me and looking me in the eye.

“Pinch my tits.”

I grabbed those tiny tits with small hard nipples and pulled, as she gasped harder and sunk lower, then up until I was almost out then back down hard, and again, and again, until she had me all inside and her clit was rubbing against me. She relaxed her grip on my shoulders and looked as if she was coming in for a kiss at last when she stopped, looked me in the eye and said,

“Oh fuck I’m going to cum ag…OOOOOOOOooooooooo”

Again her legs clamped shut, but this time I was deep in her cunt, so felt it clamp down on me and start milking. This was too much and I felt my own orgasm building.

“So am I!”

“Oh YES, cum in me, cum in me, please cum in me.” She said as she started riding me through her orgasm.

I growled as I started to shoot inside as she leaned forward, grabbed my face and kissed me at long last … long and hard. We moaned into each others mouths as we came, and even though the actual sex had only lasted a minute or two, it was one of the best orgasms I’ve ever had. She said the same.

Now here’s the deal. She told me this while still in that position, head buried in my neck, cock and pussy sharing little twitches as we came down.

In her formative years as a teen she’d read a lot of erotica … lesbian stuff, swinger stuff, fantasy stuff, but there was one line that caught her fancy and had been bouncing round her wank bank for years. It was in some sex club story and a paraphrase of the line was, “I’d known him for years, we’d go to these things together, in fact I think the first time I kissed him he was inside me”

”The first time I kissed him he was inside me.” … for whatever reason that really floated her boat and excited her inner slut, but she never thought the opportunity would come up. Until that day.

She apparently tried it with a guy years before but had told him beforehand about it … it didn’t really work, so this was a real first. And my over excitement had upped the ante, “the first time I kissed him he was inside me” had become, “the first time I kissed him he was cumming inside me.”

She climbed off but we stayed wrapped up in each other for a bit, kissing and chatting and cuddling and remarking that at some point we’d need to show our faces outside again. Best stay here until it gets dark.

Source: reddit.com/r/gonewildstories/comments/9uh1rg/unwittingly_fulfilling_a_milfs_fantasy_on_holiday

11 comments on “Unwittingly fulfilling a MILF’s fantasy on holiday [FM]

  1. An awesome read. I like your style of writing.

    I’m sure that wasn’t the only encounter you had with her. :P

  2. That was a damn good story. Pretty awesome when you can upgrade someone’s fantasy, too. Good job!

  3. Wow! Superb writing😍 I hope to see more of this kinda writing around here~ Keep up the good work man!

  4. I really enjoyed reading that. The buildup was nice, unlike some other stories that just go on about the tiniest of details, like the pen was red or the taxi cab was yellow. But great read, I truly enjoyed myself.

Comments are closed.