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You giggled, didn’t you? It’s okay, I did too. After all, “masculine lingerie” makes as much sense to our society as “normal weirdo” or “intelligent dumbfuckery.” It’s a thing reserved for internet memes and half-whispered jokes in the locker rooms, or one of those strange things you see on Wish adverts. Or is it?
If I say “men in panties” I’d bet the first thing you think of is a sissy or a crossdresser. As a society, we have been conditioned to automatically assume anyone that has a Y chromosome wearing lingerie must be “gay” or a sissy. I’ll even go so far as to say I admit that was my assumption until recently. (Yes, your favorite Mistress can occasionally be mistaken; but never wrong). I recently had a call with someone who works in the trades as a foreman for a “mid-sized company.” And he turned what I knew on its ear.

Where It Starts

When we first started our call, as always, I asked a few pointed questions to get a feel for him and what he likes. At two minutes and forty-three seconds into our call, he announced as casually as I might say I’m going for a coffee, “I put on the wrong stockings under my jeans this morning, and I need a little relief to get through the rest of the day.”
“I’m sorry. The ‘wrong’ stockings?”
“Usually I wear control top pantyhose under my jeans because I like the feeling without having to worry about my dick moving around too much. This morning, I was running late, and I put on a pair of sheer-to-waist as I ran out the door. Now my junk is bouncing around in my stockings, and I’m hiding out on the top floor of a building that is being constructed around me.”
Keep in mind, he was half-laughing as he said this, but he was quite serious. He was in a tool closet while his team was on lunch, and he’d stripped his jeans down to his ankles (Ma’am, these boots are a bitch to get off and on even in my own house, and I have about one-eighth of the space in this closet that I have in my bedroom).

Pantyhose for Dudes

Needless to say, it didn’t take very long for him to reach a climax considering he’d spent the better part of six hours being cockteased by stockings. Normally, that would be the end of our conversation, but he took the time to thank me for not being “weirded out” by his wearing stockings. I assured him I speak to many men who love to wear lingerie, and that’s where he took me on a sidetrack. I asked him about how he got started wearing stockings, expecting to hear a story of a childhood curiosity or a cruel ex-girlfriend. Instead, I found myself talking about a black-tie event.
“A few years ago, my company won a fairly large contract, and we were celebrating its completion with a formal party. Complete with the penguin suits, free champagne toast, and an open bar. Shocking as it may be,” he began, chuckling a little under his breath, “I don’t actually own a tuxedo. But seeing as I’m one of the bosses, I figured I’d do it up. So I went to a Men’s Warehouse in the mall and asked about buying one. The guy in the store helped me pick something out that I liked the look off, and he was taking measurements and gettin’ real personal with my ins and outs. But he was cool and had me laughing the whole time. Anyway, so we finally finish measuring, I head out, and he tells me when to come back for the suit.
“When I went back, I tried the suit on and it was good. At least, he said it was good, and one of the other people in the store commented. I was happy. I’m going to take it off, and he starts asking me about shoes and what I’m wearing with the suit. Ten minutes later, he’s got me sitting in a chair, and I’m holding a pair of nylon socks. The first thing out of my mouth is something about how they feel like my girlfriend’s pantyhose, and he starts laughing at me. Tells me they are “pantyhose for dudes,” and I need to wear them with my new dress shoes.”

Read up on Saturday for the rest of this story …