Never Have I Ever: Joined the Mile High Club

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Joined: Nov 2022

Here’s What It’s Really Like to Get It On in an Airplane, Told by Someone Who Did It

Never Have I Ever: Joined the Mile High Club

Here’s What It’s Really Like to Get It On in an Airplane, Told by Someone Who Did It

Have you ever played “Never Have I Ever” before? Here are the rules: Everyone puts up ten fingers, and you go around in a circle and one by one share something sexy or scandalous that you’ve never done before. When someone else shares something you have done, you have to put one finger down — and of course, drink. The first person to put all 10 fingers down loses (or wins, depending on how you look at it).

Well, AskMen is still playing Never Have I Ever, and the rules are simple: In each edition of this column, we speak to someone about doing something new in bed, whether it’s a long-time fantasy, something that just happened, or even something they regret. They tell us everything so you get an inside look at what some sexual experiences are actually like.

Joining the mile-high club feels like the stuff of legends. How does anyone possibly pull it off in a post-9/11 world, where air travel is as much security restrictions as it is actual flying?

Well, the answer is — it takes a goddess like Aviva Diamond, a New York City-based dominatrix.

According to, and as Aviva will tell you, red-eye and international overnight flights are particularly adored by those aiming to join the mile-high club because of the dim cabin lights, not to mention the availability of genital (and feet) covering pillows and blankets, and the fact that most of your fellow passengers are likely asleep.

Despite their popularity for such rendezvous, airline bathrooms are notoriously unclean and cramped, often providing just 9 square feet of space, so, as Aviva learned, under-the-blanket foreplay (and flexibility) is a must.

But, while she’ll give you some expert tips, know that if you’re curious about joining the mile-high club, lavatory doors can be opened from the outside. And, even if they’re kind enough to let it slide, flight attendants often can tell when passengers decide to fool around.

Plus, the risks are real, with potential legal repercussions. Having sex in your seat or being caught getting it on in the bathroom could lead to charges of indecent exposure, arrest, and even felony charges.

But as Aviva tells us, she was able to get away with it, have an incredible orgasm, and feel like an absolute baller upon landing. Here’s how it all went down:

Before your experience, had you seen depictions of the mile-high club in films and TV? What were your expectations?

I had seen a few references to the “mile-high club” in movies and shows, and being a sexually curious and explorative person, I was excited about the idea of being on a long flight with a lover where I could possibly join the club. Thinking of having sex so many miles up in the air and having to be discreet with the possibility of getting caught was totally hot to me.

So, tell me about your experience.

It all went down on a 14-hour-long flight from LA to Sydney with a submissive boy toy. He was based in Australia, but we had met in NYC when he came for a trip and decided to book a session with me as a Dominatrix.

We had an instant, electrifying chemistry in the session, and he came back to see me a couple of days later. After that second session, the spark was too much for both of us to resist, and I decided to transition our dynamic from professional to personal, turning him into my own sex toy.

He was a typical golden boy: handsome, with a successful career in sales, and an “alpha” exterior that fooled most people. But with me, he was a weak, foot-obsessed bitch that started flying me around the country when he would have work trips so he could worship me on my knees.

Eventually, he flew me out to Australia with him so I could have a warm winter vacation, which is how we were both on this very long flight with a row all to ourselves. I already had it in my head that I was going to fuck him on that flight.

And you did? How did it happen?

There was a moment during the journey when the cabin was dark, and most people were sleeping, and I knew I had to act fast before they started the breakfast service.

Naturally, I used his strong foot fetish to turn him on and have my way. I was seated with my back to the window and placed my feet under his blanket while he was on the aisle seat. Under the cover of the blanket, I started rubbing my soles against his cock in his pants, feeling him get harder and harder.

I was getting more turned on as I felt his erection with my feet. He was a little hesitant when I told him we should go to the bathroom to fuck, but my foot teasing was enough to make him too horny to care.

We decided to head to the nearby bathroom, one shortly after the other. I’m not sure if anyone saw us both go in, but we somehow managed to maneuver in the tiny stall so I could lift a knee up onto the counter, facing the mirror.

He crouched down to lick my pussy from behind, making sure I was wet, then stood up to thrust his hard cock in me, fervently fucking me. We didn’t have much room, but I was so turned on I was having a hard time not making sounds as I quickly came.

I remember he was worried the flight attendants would hear, so he kept trying to shush me. Honestly, I don’t remember if he came or not. I think I was very focused on my own pleasure, and the whole thing wasn’t very much time.

How did you get away with it? Were you worried about getting caught?

We had the same method of leaving as coming, so he left first, and after a couple of minutes, I left, too, and made my way back to our seats.

I didn’t really worry or care if we were going to get caught; I had been fantasizing about it for so long that I knew I had to make it happen. And thankfully, no one said anything to us, so we got away with it.

Soon after, we sat back down. They started breakfast, and we then landed in Sydney. I remember looking out the window at the gorgeous landscape as we started our descent and feeling very pleased with myself.

What is your advice for anyone looking to also join the mile-high club?

If anyone is thinking of joining the mile-high club, I would recommend working on your flexibility and doing as much foreplay as possible in your seats. It helps to be on a flight where most people are sleeping, too. And don’t make as much noise as I did cumming!

I have no regrets and love that I have this story to tell, but at this point, if I was going to fuck on a flight again, it would have to be on a private jet where I would have more room and could really let loose.

AskMen does not condone illegal activity. Make sure to research whether it’s OK to engage in sexual activities in a given situation before you do, as getting caught in some of these situations could lead to financial or legal repercussions.

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Source: AskMen


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