Read this before continuing on.
I haven’t spoken with the pilot for a couple months now, not since January 11th specifically. I would have written more about him sooner, but I was waiting to see what my decision on him was going to be and where things were going to go, and then I got annoyed with him and backed away and we just stopped talking. Let me take you through the last year with him.
He lives in Toronto and usually only flies into Regina every couple of months or so, sometimes more, but it’s not always an overnight trip. So after the first time he came over, I didn’t see him again until sometime in the late summer. We texted several times a week, he liked talking on the phone too, but I hate it. So every once in awhile I’d answer when he called, but most of the time I’d ignore it. Despite me telling him how I don’t want to talk on the phone, he would still try it. We talked about everything, including other men and women in our lives. It was nothing serious, although he would often wonder if I would date him if he lived in Regina or I lived in Toronto. My answer was always “maybe”. I would have considered it in the beginning, but we wouldn’t have been right for each other in the long run. He’s into some rather specific sexual fetishes, and I think he’s confused about his own sexuality. He experiences a lot of guilt regarding his desires. We had a lot of conversations about them, and I told him many many times that he is allowed to explore and want what he wants, as long as it’s not illegal and doesn’t hurt anyone.
I’ve told you about his fetish for women’s underwear and clothing. He liked knowing what I was wearing, but sometimes it was more so he could fantasize about wearing my dress, rather than imagining me in it. Or out of it. Prior to his visit in the summer, he would send me pictures of lingerie he was looking at online. It was usually Vanity Fair, either white, blue, or pink. He liked panties, bras, and slips. He kept saying how hot it would be to go shopping together and he’d buy me some to wear. And of course he talked about wearing them himself. I asked why he didn’t just buy himself some, or shop where he was. I’m sure there’s a much better selection of what he likes in Toronto. He could shop online, or go into a store and say he was shopping for his girlfriend. Hell, with the type of lingerie he likes, he could say he was shopping for his grandmother in the nursing home! But he was too embarrassed to do that. He did order a few things online, but as far as bringing anything with him, he would never do that. I told him to just put them in a gift bag and anyone checking his bag would assume he brought a gift for a woman. What’s the problem? Still too embarrassed. So, when he came through in the summer, I met him at his hotel and stopped at Sears on my way over. I bought us both a pair of pink satin panties, and stopped in the lobby ladies room to put mine on.
When he opened the door to his room, he was just as cute as I remembered. I could see why flight attendants of both sexes would flirt with him. He was a lot of fun to make out with. I liked kissing him, and I liked his hairy chest. Truth be told though, he could have used a bit of manscaping. Men, I cannot stress enough the importance of grooming around your penis. If the dentist congratulates me on the health of my teeth and I don’t even own dental floss, your hair is too long.
He loved the panties I was wearing. Literally could not stop touching them. He was very interested in the toys I have and asked that I bring one or two along with me. I brought a couple of my favourites and let him choose. Of course he chose the one that looked most like an actual dick. He kissed me up and down my body, trailing his hands along with his tongue. He had good hands that worked me inside and out. And then he wanted to use the toy. Before I got to have fun with it, he gave it a mini blowjob. (He liked to talk about his one fantasy where I could wear a strap on and make him give me a blowjob.) Then he fucked me with it. I don’t often orgasm when I’m with a man, but I did that day. I asked him if he wanted to wear the panties I’d bought for him. He said no, that was ok. I couldn’t believe it! I told him to get fucked and put on the goddamn ladies underwear I’d just bought for him! So he did. And I swear, he almost came just by putting them on. We started making out again, and let me tell you, it’s a little weird running your hands down a man’s body and feeling satin. It wasn’t bad though. Actually kind of nice. I mean, it’s soft, I like touching myself when I’m wearing nice lingerie, so it’s kind of the same thing. It didn’t turn me on, but it didn’t turn me off. It was just a new experience. He loved it though. When I finally pulled his dick out of his panties (I never thought that was something I’d be saying) and put my mouth on him, he was done in about a minute. I’d like to take credit for that, but granny panties did most of the heavy lifting there.
We did not have sex.
He left the next day and we continued our regular contact. I began to grow tired of our conversations. In matters of life, he would give me advice/lectures like my dad. If we talked about sex, it was always about his fantasies, and I was rarely the star. They got more intense as the weeks went on. I’ve had some great sexting with men in the past. Really great. Screenshot this for later kind of great. The pilot was not great at it. For starters, it was always about my ass. He’d fantasize about the big white panties I’d be wearing, pulling them down, and burying his tongue in my ass. I admit, it doesn’t sound that bad, but my kitty got awfully lonely in these fantasies. After awhile, my ass wasn’t even the understudy. It was all about his ass. He wanted me to order a strap-on for the next time he was in town and use it on him (He would pay for it). I had already told him several times I didn’t know if that was for me. And every time I engaged in conversation about it for curiosities sake, he took that to mean that I was starting to get turned on by the idea. Almost everything he liked, I really didn’t care one way or the other about. I wasn’t opposed to most of it, but it also wasn’t anything that got me revved up. I’ve licked and fingered an asshole or two in my day, and it’s not something I work into my own fantasies, BUT, in the moment, it can be pretty hot. Anything that you’re doing that gives another person so much pleasure is a turn-on. What really turned me off about doing it with the pilot was how much he talked about it, and tried to push it on me. It was the same with the lingerie. He would send me pictures of things he liked and ask which I liked better. I do not give a fuck what kind of panties you want to wear. I can’t imagine him finding any panties that I would think were sexy with a dick bulge.
Oh, I should mention the strap-on wasn’t anything that was new to him. He had been sleeping with a woman who loved using one on him. She was quite dominant. They probably could have had a very nice relationship with both their needs being fulfilled, but she was already married. And the things she wanted sexually, she had to step outside her marriage to find. The pilot worried he would never be able to find anyone who he would be able to share all his needs and wants with. He would go to these hottub parties and get fondled and blown by gay men. Sometimes there would be a woman thrown into the mix, but it was mostly men at these parties. And he would wonder what it was like to have a dick in his mouth and to perform oral sex on another man. He had a fantasy of having a threesome with me and another man. He wanted us to give the other man a blow job together and then watch me have sex with the other man. But he wasn’t gay or bisexual. *eyeroll* Ok man, whatever. Don’t label it, but don’t be afraid of it either. If you want to suck a dick, suck a dick. And finally, he did. But all these things he did, all these thoughts and fantasies he had, he felt so guilty about them. He started going to see a therapist about his “urges” and to try and fix them. Of course I told him that if the therapist agreed that he has a problem, he should find another one. But if they were actually helping him with acceptance, then great.
It was getting to the point that if he brought up sex, I just didn’t even want to continue the conversation. In November, right before my birthday, he offered to buy me a dress I wanted. It was gorgeous and expensive, and not at all in my budget. And he wanted to buy it for me. I said no. He tried to convince me to let him and I just couldn’t. It was not something that made me comfortable at all. At one point, he told me if we dated, I could have all his money. Everytime I went out, he would tell me how he wished he could be with me to watch me get dressed and be waiting for me when I got home. More than once he said he wanted to be my girlfriend. THAT turned me off. I like a sexually dominant male. I don’t want a girlfriend. And he knew that. He knew that’s why it would never work out between us in the long run. We might be able to have some fun here and there, but that would be it. And the fun in this whole situation was getting to be less and less. He was going to be in Regina after new year’s and we had plans to get together. But the closer we got, the more he kept asking about things. Like, was I going to bring the panties, was I going to get a strap-on, etc. Constantly. I got really annoyed, and he knew it. I was starting to make excuses for why I might not be able to meet up with him. I finally told him he was putting way too much pressure on me. Cross-country sex should be fun and exciting and freeing, not stressful. His flight got delayed in Winnipeg anyways, so it turned out to be a moot point. We didn’t talk much the week after that, and then nothing at all.
Yesterday was St Patrick’s Day and it reminded me of last year when I had first met him. I decided to send him a quick hello, see how he was doing. Right before we stopped talking, he had begun seeing a flight attendant with another airline. Maybe I should have left well-enough alone, but I hoped it would be a quick hello, how’s life, you doing ok, cool, ttyl. To start with, when I sent my message, his response was, “who is this?” Ouch. I didn’t respond. About a half hour later though, he sent another message saying, “Amy? Happy St Paddy’s to you too”. I said “Yep”. We had a brief conversation and I ended it with, “Well, I just wanted to say hi because I was thinking about you. I have to go meet a friend. Take care and have a great night”. He said the same and I breathed a sigh of relief. Until an hour later when he messaged me again. Asking about my night, why we stopped talking, etc. I said I hadn’t thought about it, and I was on my way to the pub, so, again, have a good night. He texted me again today. I should not have texted him yesterday. I should have let it die. But now, now I’m going to have to stick my dick in his ass. Sigh.