So in my story, one of the main characters (who is a man) uses a disguise to get out of jail and avoid getting caught by police. The disguise? Woman. And even though it's set far into the future, what would this really be like? For starters. The man is in his early 20's, 6'0", long hair, very effeminate, skinny, and always try to stay healthy. I could add "If he wanted to look like a real woman, all he had to do was put on women's clothes, wear a scarf, and some make up." But how long would it take to make a real disguise? Would his height raise some suspicion? Because the thing is, I don't know shit about crossdressing. I'm a male, and I'm perfectly happy being male, I have no desire to crossdress, and frankly I would look terrible. Unless I did it as a joke haha.
Hello, friend. Do some research about cross-dressing, watch videos about that subject especially men and see if some of their situations apply to your character. Plus, I will suggest adding in your character some feminine features, in his face, for example, so his disguise can be appealing, and who knows? That could be a conflict already to his story? I hope this helps. Keep on good work and have fun with that project. Sounds already a good premise.
He's in jail so he'll need to get hold of the clothing, somehow. I'd say that's your first hurdle. Where does he get it from? And how does he actually 'escape' a locked jail cell? And if it's far in the future, wouldn't there be things like face recognition technology, etc? Body scanning, etc. I'd say you've got a lot of story problems to sort through, before you start thinking about how to fool the police if he's too tall or not feminine enough. Even in today's world, it's not easy to say, 'Oh, officer, can you let me out of this cell, please? I'm not really the person you thought was locked up here. I'm a woman, and this is all a big mistake.'
Depends on the prison. Most have canteen, in which you use outside money to buy conveniences not normally supplied by the institution, like snacks, hair conditioner, etc. Some prisons will provide some cosmetics to 'male' inmates; some won't. Though having him get them directly may cause some unwanted attention. Trading favours from another inmate to get them may be smarter. Also, applying said makeup could be a problem. People that have been doing it for years can do it in probably a half hour, but if it's his first time, it could take hours just to get it somewhat convincing. If there's a female side to your prison, it'd be a lot easier. Have him work laundry, where the clothing of all incoming inmates is washed before being stored, and he might be able to smuggle some out. Also, prison razors suck, and usually aren't available 24/7, so there may be beard timing issues.
You might find this story interesting: https://www.theworldorbust.com/i-escaped-prison-in-mexico-dressed-as-a-woman-a-special-interview-with-dwight-worker/ The true story of Dwight Worker who escaped a Mexican prison dressed as a woman. NC
Good things to think about. It also might be worth noting that all women don't wear makeup! In fact, makeup plastered on a man's face might call more attention than he might want to attract.
also the walk can be a give away, men and women don't walk the same, and its very difficult for a man to fake a feminine walk or vice versa
Let's see... Something that looks like tall & skinny woman in her twenties in male jail... I'm sure that would raise something. Several somethings. I'm not sure if it would be suspicions. I suppose guards would not be the biggest problem.
I know it would be suicide to crossdress in a male prison, but what about the outside world after they escape the actual prison itself?
Unless this is an almost-all-female society, I think that disguising himself as a woman is more likely to attract attention than just drastically changing his male appearance. Hair dye, haircut, maybe tanning booth, extremely different but still bland clothes, including something bulky (more difficult in summer, admittedly) to hide his skinny build, and so on.
Few hours ago the reason was to get out of prison. Now it is... something? I don't get the point any more. It looks like a floating point to me. If someone wants to escape prison there must be a reason. Why he's is escaping? There must be a plan. How he tries to escape. There must be obstacles. Plan can't take everything to account. (And it is often not suicide to crossdress in jail. Sometimes it is a way to survive. I have personally met a person who crossdresses in prison but not when he is outside.)
Gets a visit from wife/sister/lover - she smuggles some clothes and make-up to him, he has a good shave and leaves with the other visitors the following day. That's exactly what happened in the true story I posted above, I don't think its needs to be overly elaborate or complex - sometimes the simplest solution is the best.
I remember that! They interviewed someone about it, the wife maybe, on NPR 5-6 years ago. What a weird story. They spent months planning it, memorizing the guard changes and routes and so on. And I think he still had to ask someone to unlock a door? I guess in Mexico they have interesting customs about this. It isn’t a crime for the wife to help the husband escape because it is expected of her, and if you get out, you are free to go so long as you don’t injure anyone or break anything (no digging).
I think it was an episode of 'Banged up Abroad' (Locked up Abroad in the US), really was a fascinating story!
I think a big issue is where did he disguise himself as a herself? If it was in his cell, then how did he get out? If it was elsewhere in the prison, how were no flags raised that a civillian woman was in the inmate (probably male) section of the prison? How did homeboy get these female clothes? How did he deal with, oh, I dunno... facial hair, short male haircut, body hair in general (How many women do you know that have hairy limbs? I know zero. Every guy I know is a candidate for Bigfoot, myself included.) His voice is probably deeper, so how does he communicate?
A lot of that has to do with personal grooming there are a lot of hairy girls out there, and a lot of not so hairy guys out there.
Big hands, Adam's apples and low voices are often the main giveaways for CDs/trans girls so you could add in some details about trying to conceal those things.
I hope you don't think that comes natural. It takes a lot time and effort to keep those limbs hairless! As a dark haired lady I could compete with the men within a few months if I decided not to shave my legs. Just... putting that there. Sure - I'm not suggesting the character could shave entire body in prison - but the way I've seen men react to hairy legs on a woman before... I just had to comment.
Or do like every girl I've ever been in a long-term relationship with and only shave the bits that show in public.
OFF TOPIC Genitalia does not lick... (Well, wait a sec...) Genitalia does not whine if... (No, not that.) Genitalia does not have fake gems in it's... (Maybe not that either.) Genitalia is a pussy. Fifi is a do... (or is it?) You can't walk genitalia in a park in a collar and... (Oh shit. They do it all the time.) Genitalia does not accept anyone who smells bacon. (Well, there are many kinds of kinky...) Genitalia does not eat you sausage. (Not that. Too easy to misunderstand.) Oh... Now I know! Dapper, Moon, Troll , Ian or someone else will answer that question!
I see you Fins don't have the same nicknames for your genitalia as your neighbors. Before Snippa became all the rage people called it Fifi (after fitta). I'm sure your Swedish is good enough to know that word
