Mile high MILF — Byron’s story

Byron meets a very horny MILF en route to Singapore

Andy Word
MILF Magic
7 min readOct 27, 2021

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In the taxi on the way to the airport I kept pinching myself. How lucky was I? I’d only been with the company, a Forex provider, and here I was on my way to Singapore. The only drawback was that my cheapskate boss had only booked me in cattle class.

My colleagues had given me some advice on how to get an upgrade so I made sure I was smartly dressed and checked in as late as possible. And it worked! Seems there had been a last minute cancellation and I was the lucky beneficiary.

It’s great when you board a plane and turn left! However when I got to my seat there was a lady already in it.

I think you’re in my seat.

I said as politely as possible. She turned and looked up at me.

Oh I’m so sorry, I must have cancelled the wrong seat. My colleague couldn’t make it, some last minute problem. Here let me move.

She had the most gorgeous smile and I just melted.

No don’t worry, this one’s just fine.

She introduced herself as Caroline. She worked for an investment bank and was a regular travelor on this route, she didn’t tell me her age but I guessed she was a good ten years older than me — so mid-thirties I reckoned. When I explained that it was my first time she said that it was pretty uneventful usually and once it got late everyone seemed to turn their lights out and go to sleep.

I got my bags sorted and strapped myself in beside her. The seats were really generous and the armrest between us was wide enough for both of us to rest our arms on. The cabin crew went through their normal drill and I felt the plane start to move back from the gate. Caroline was talking about her job but I noticed a slight change in the pitch of her voice. Instead of a lovely rich, almost velvety tone, it seemed to get a bit more edgy.

Are you ok?

She looked slightly nervous and her hand brushed against mine.

Actually I am a nervous wreck until we’ve taken off. I don’t know why I’m done it many times.

I gripped her hand in mine, it was a bit sweaty.

Don’t worry, I’ll try and help you take your mind of it.

She gripped my hand tightly and I just started talking about, I don’t know what, anything that came into my head — my school, my hobbies, holidays I’d been on, how I was excited about going to Singapore, and before we realised it we’d taken off and the plane’s engine cut back to normal and the rate of climb slowed.

I felt her relax, she fanned herself with her hand and stroked my arm, thanking me profusely. The touch of her hand on my arm sent a tingle through me. I looked over at her. She was wearing a long pale cream sleeveless dress, made of some soft material that didn’t appear to crease . It seemed to hug her figure to perfection. The neckline was low enough to offer an inviting glimpse of an impressive cleavage and the colour of the dress against her coffee coloured skin was amazing. I could feel my cock stirring so quickly make my excuses in need of a comfort break.

When I returned I was greeted by her beaming smile and as I sat down my eyes were drawn to the front of her dress. Where those her nipples I could see proudly pushing the material up? Was I having some kind of sexual effect on her, as she was on me? Forcing my eyes up front her breasts I was about to speak when the flight attendant stopped and asked us what we wanted to drink. Caroline asked me if I liked red wine, which I did, so she ordered a bottle for our evening meals and she ordered a gin and tonic for now, I had a beer.

Despite the age gap it seemed we had a lot in common, we both seemed to like a broad cross section of music, the films of Quentin Tarrantino and a love of Thais food. We talked and talked, right though our evening meals and well into a second bottle of wine. We were talking and laughing and laughing and yes, flirting. I was conscious that as the time went on she was touching me more and more and for longer each time, she was definitely checking me out. On several occasions I had to surrepticiously readjust myself to keep comfortable.

Eventually the stewardess said that the lights were going to be turned out so people could sleep. Caroline sighed, I was fairly sure that she was a little tipsy, indeed I could feel the buzz of the alcohol.

I wish we could talk all night.

She said wistfully.

But I appreciate that we both have jobs to do tomorrow so we really should be sensible about this.

Yeah, you’re right.

I was a little disappointed but I understood, she was a seasoned traveller, she knew what worked and what didn’t. She said that she was going to the bathroom first, so I got and let her out. It really was a marvellous sight as I watched her walking away from me. What a fantastic figure, what a gorgeous ass.

She needed my hand to allow her to get back into her seat, so yes, definitely a bit squiffy. I let her get settled first and then went off to the bathroom myself. When I returned she was already wrapped in a blanket, her seat reclined with her eyes shut and her faced turned towards me. I carefully sat down beside her, reclined my own seat, and pulled my own blanket around me. I’d be lying if I didn’t own up to having a massive erection as I lay there thinking about the amazing, beautiful, woman beside me. Eventually it subsided and I drifted off to sleep.

I was dreaming about being on a white sand beach, somewhere in the south Pacific, I’d been swimming in the azure sea and now the sun was beating down and drying the salt water from my body. I could feel the warmth radiating across my body, weirdly it was coming from one point on my body, not from the sky. It was coming from my groin, a wonderful soft sensation, stroking me, stroking my erection. Yes that was it. I stirred and I heard a voice in my ear say.

Byron, I think you should wake up now. But be quiet.

The voice kept repeating this mantra and I could feel the stroking increasing in strength. I woke up with a start. Caroline was very close to me and what I could feel was her hand on my cock.

Ah, that’s better, you’re awake now. I’m sorry I just couldn’t stop myself. After all I knew you’d been checking me out so I thought it was only fair. And my am I glad I did. You really have been hiding your light under a bushel!

She leaned even closer and her lips dragged across my face and found my own. Her tongue pushed it’s way into my open mouth. She tasted amazing, and now she was so close she smelled amazing. Her hand continued to massage my cock and balls, she’d already opened my trousers and pulled my briefs down.

I didn’t say a word, I just pulled her closer to me and she quickly stradled my legs. I reached up and slipped the straps of her dress down over her shoulders. As I hoped and expected she wasn’t wearing a bra and her glorious breasts sprang free, the large dark brown nipples were already hard and when I sucked on one Caroline moaned gently. My hands went to her hips and I grasped the soft material of her dress and began to pull it up. She helped me and soon it was around her waist like a large cummerband. I could feel the heat from her sex on my cock and balls, she wasn’t wearing any knickers either.

Sit back and relax and let me take control.

I nodded enthusiastically and focussed on tweaking her nipples, enjoying her expression of pleasure in the half-light. She rubbed herself against me, I could tell she was wet, she grasped my cock and rubbed it against her slot, using it to repeatedly bang against her clit. Each time she moaned a little more. I was desperate for more and she seemed to sense this and positioned the head of my cock against her and slowly, and oh so wonderfully slid down my manhood, all the way down, taking me deep inside her so my balls were touching her.

The movement of her hips was astonishing. It was very slow, I could feel the muscles of her pussy walls grasping hold of my shaft. I moaned and she put a finger on my lips.

Quiet, you don’t want to wake anyone!

OK

I stammered breathlessly. I placed my hands on her hips and helped to life her up so she could crash back down again. Oh my god it was wonderful. Her breathing started to get shorter and faster, the pressure from her pussy muscles was growing in intensity and when I felt I could take no more — the pressure in my balls was incredible — she raised herself one one last time and slumped down on me her whole body shivering and shaking. Her pussy had clamped rigid around my cock and that tipped me over the top. I could feel my cock swelling and forcing her pussy wider and then the rush of juices along the length of my swollen shaft which then erupted into her, flooding her, and bringing a huge smile to her face.

Wow, that was fantastic.

I gasped in a stage whisper.

You’re an amazing woman, so fucking sexy, so hot.

She kissed me repeatedly and ground her hips against me, extracting the very last drop of cum from my collapsing cock.

You’re not too bad yourself. Thank you for making me one very happy horny lady.

She rolled off me and quickly pulled her dress down and up and disappeared to the bathroom. When she came back she was still beaming from ear to ear.

You realise that there’s still another 4 hours to go, don’t you?

I smiled back at her, I opened my blanket to reveal my freshly hardening cock.

Well I’m up for it if you are!

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Andy Word
MILF Magic

I write about other people's sex lives. Well maybe some of my sexual fantasies creep in now and again, but I never kiss and tell, a gentleman just shouldn't!