The Air Canada Pilot

St. Patrick’s Day, 2014. I was at one of the local pubs enjoying myself, forgetting about the funeral I went to earlier that day. I was on fire that evening. My milkshake was bringing ALL the boys to the yard! One of these boys (I guess I should call him a man. He’s in his early 40s) was a pilot for Air Canada, just in town for the night. Shorter than I, but very handsome. He struck up a conversation with me and I gave him my number. The friend I was with pulled me away to meet some other men, but the pilot had texted me almost immediately after. He also found me before he left to say goodbye. I was tempted to leave with him, but there were just too many other men left to flirt with. We spent the next week or so texting and I learned a lot about him. My conclusion has moved from my previous assessment of all pilots loving having their balls licked to all pilots are a little kinky. I shall explain.

This pilot enjoys lots of anal play, male and female. A previous girlfriend of his enjoyed fucking him with a strap-on. He also enjoys women’s underwear, specifically big, white granny panties. And while he likes seeing them on women, he really would like to wear a pair himself. He’s been too afraid to go and buy some of his own. I don’t really understand that. I mean, he lives in Toronto, he could go anywhere for them, no one would know him, and even if someone asked, he could say he was buying them for his girlfriend. He asked me a few times if i would go shopping for him. I refused. Not because it turned me off (I don’t particularly care either way about this fetish), but because I was not willing to go out and spend money on underwear for someone I hadn’t even slept with yet! And at one point during our texting, I had to tell him to stop talking about underwear, and if he expected to get anywhere with me, he’d better start making the conversation and sexy talk more about me, and less about what his fetishes are. Men these days!

When he flew back into town, we made plans to get together. His flight got in late so I invited him over for a drink at my house. I should also mention that before he got in, I made it clear to him that I would not be promising him anything and he had better not have any expectations of how our time would be spent. And if we did have sex, it would be very vanilla to start. In other words, although I do sell strap-ons, I would still not be able to review one after he left. He was ok with that. Unfortunately, I didn’t really get to take him for a spin. I had some yeast infection symptoms and started treatments that afternoon. TMI? Whatever, you knew what this was when you started reading me! We had a drink and he made his move. Because of our height difference, it felt like I was a mountain he had to climb. A mountain he was quite eager to reach the summit of. He kissed me, long and deep, and he smelled soo good! It was getting hot, and then, suddenly, what’s that? Is that…3 tongues in my mouth?!? Fuck, Walter, get out of here! Me, the kinky pilot, and my dog is not my ideal threesome. I bribed him with a treat to go away and we got back to business. The dog, I mean. I bribed the dog. I asked the pilot if he wanted a pair of my satin panties to play with. Obviously he said yes. So for awhile I watched him stroke himself with my pink satin and lace panties, fascinated. I’m pretty open-minded about whatever turns other people on. I blew him while he fingered my panties. But he wouldn’t cum in my mouth. He said it wasn’t fair because he couldn’t make me cum. Apparently he’s a kinky gentleman. Not enough of a gentleman to turn down the blow job in the first place, but hey, you can’t fault a dog for being a dog.

He hasn’t been back in town since, but his schedule does have him back through in May, so maybe I’ll take him for a full spin at that time. If it ever gets to a strap-on point, I’ll be sure to let you know 😉

PS. I’m currently talking to a pilot for Sky West. Purely for research purposes into what else pilots are into.


4 thoughts on “The Air Canada Pilot

  1. Pingback: AC Pilot, Part 2 | thehungrycinderella

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