Thinking Out Loud + Crossdressing

[Stoutland395]

As some of you who've read my stories, here and on deviantArt, know I deal exclusively in M/M content. It's odd that I consider myself straight, but my kink revolves around seeing guys tied up. I appreciate and admire a young guy's looks/appearance to a point that I want to see him hogtied on the floor. But while some people go beyond that point, I don't feel that desire (hence why I don't care for the more risque/adult stuff - but more power to you if that's your thing). I think the furthest I'd go is cuddling up to the guy and teasing him as he tries to get untied. My kink pretty much stops at the guy's underwear/boxers.

For the most part, I like the stereotypical guy's sense of "style." Jeans, plain t-shirts, button-downs, etc. A roll-up sleeve for that professional look. My favorite looks are anything Nike attire. When I see a guy wearing black Nike socks and shorts, or black/white Nike shoes - it's almost impossible for me not to look away. And although I'm by no means an athlete or even interested in sports, I do admire the sports attire. Track shorts, basketball tank-tops, baseball raglan shirts, and those black Under Armor compression shirts.

But crossdressing has been a topic I've seen frequently talked about as a supplement to the bondage treatment, and I've always tried to leave a comment so I could follow, but I don't think I've ever encapsulated exactly how I feel about it because it kinda presents a weird and confusing feeling for me. Typically crossdressing - from what I've seen - involves people trying their best to look like the opposite gender, and I've seen some very convincing looks, to which I say "Bravo!" Or it's done for humiliation purposes, which I don't care for (You're getting tied up, and I have my hand over your mouth not letting you talk. You'll be plenty humiliated enough)

On the womens' side of it, there's a lot of looks that tend to earn my immediate respect and admiration. I think it first started when I saw Tilda Swinton in the movie "Constantine" and I saw a younger Swinton, clearly a woman to me, portraying a guy/angel (Gabriel) complete with a suit and everything. Although I was much younger, she attracted my attention and she's an actress I still admire today (even though she is waaayyy older than I am). Another - this one an animated/cartoon character - was Integra Hellsing from both "Hellsing" animes. I don't like smoking, but seeing her dressed in a typically male attire, cigar in one hand and cane in another - she instantly became one of my favorite anime characters ever.

But on the bondage side of things, I don't see them as a part of any of my actual kinks.

Guys on the other hand are a different story. I don't care for the guys who go all the way and pull off very convincing feminine looks because by that point they don't look like a guy anymore. But that hasn't stopped me from imagining someone who is very much a guy - toned arms, abs, all that - wearing women's clothing. It's a hard look to find, honestly (maybe not surprisingly). T-shirts with ruffled sleeves, or short tunic shirts, blouses, anything knit/woven, mid-length capri pants. I'm 50/50 when it comes to dresses, though. I wouldn't mind seeing a young skinny guy (the likes of those vain Instagram stars who are famous specifically for their boyish good looks), with all the masculine features intact, in feminine clothing getting subjected to a night of bondage. Someone who ID's as a guy - with the standard guy's interests and attitude - but also wears capris and a ruffled blouse.


Sorry that this was a long post. Being in between longer-length/multi-chapter stories, I've long thought about including a crossdresser in one of my stories down the line, but I want to make sure I do a character like that justice - beyond the guy who dresses in a 'sexy maid outfit' or just being some dude in a dress.
I had a personal itch to try to straighten some things out in my head, and this was one of the recurring thoughts I had, and writing it all down helped me. And I figured maybe someone might find some interest in it.