Comments on: Hey there sailor, how you doin'?

Question: Hey there sailor, how you doin'?

Anonymous — Fri, 08 Feb 2008 14:11:09 -0800

My lady friend has a request for me to be a sailor – for a night. Help me fulfill her wish.

So, if you were setting this role play up, what would you do? I have a little white sailor hat and sailor shorts. This is my first time (and hers) doing anything of the sort and would appreciate any guidance. I've seen some of the other "situation" idea's out there. But I am unsure of how to follow through with this and would like to keep it a surprise.

If you would rather not post your advice publicly, please send correspondence to thetenthstory@gmail.com. I just didn't want this post linked with my account.

By: Electrius

Electrius — Fri, 08 Feb 2008 14:14:27 -0800

Keep in mind that roleplay is about fantasy, so behaving how a sailor actually acts is likely to disappoint her. You must determine what it is she likes about her conception of sailors and play that up.

By: dersins

dersins — Fri, 08 Feb 2008 14:14:36 -0800

Well, all sailors know how to tie knots pretty well....

By: jouke

jouke — Fri, 08 Feb 2008 14:22:22 -0800

Yeah, you should get more information on what she likes. Otherwise you run the risk of dressing up as a sailor and for instance unwittingly giving of a gay vibe that she might not like.

dersins bondage suggestion is interesting but also depends on how she feels about that.

By: mausburger

mausburger — Fri, 08 Feb 2008 14:22:35 -0800

What about a navy uniform in white?

By: Ironmouth

Ironmouth — Fri, 08 Feb 2008 14:29:03 -0800

You've been on a ship at sea for months. You can't control yourself. She can be a librarian.

By: whoda

whoda — Fri, 08 Feb 2008 14:32:13 -0800

There was a Sex and The City episode about the 'girls' and their antics during Fleet Week in New York. Maybe watch that and see if you get any ideas.

By: Greg Nog

Greg Nog — Fri, 08 Feb 2008 14:44:53 -0800

I think you should have sex with her while wearing the costume.

By: yohko

yohko — Fri, 08 Feb 2008 14:52:58 -0800

little white sailor hat and sailor shorts

If you are a man, she is more likely to want you to wear something like a sailor/navy uniform than cute little sailor shorts. Obviously, ignore this if she gave you these items as part of requesting the fantasy.

So, if you were setting this role play up, what would you do?

Well, the answer to this is almost always to find out what your partner would like. Sometimes the answer is to figure out what you would like. Since you want it to be a surprise, contrive a way to observe how she reacts to various stereotypes of sailors, maybe by watching an old classic movie. She is asking you to act out a role, but there are a lot of different types of sailors -- pirates that might kidnap her, navy men on shore leave, etc. You need to act out her idea of what a sailor is, and we of metafilter will have many ideas, but unless you are going to invite us all over we won't be able to tell you what it is that she likes about the idea of sailors.

By: 517

517 — Fri, 08 Feb 2008 14:55:57 -0800

"I have a little white sailor hat and sailor shorts."

Are you sure that's what she is looking for? Because there is a masculine way to dress like a sailor and it doesn't involve shorts. Go to a military surplus place and you can probably look a lot like a real sailor for less than $100.

By: scrump

scrump — Fri, 08 Feb 2008 15:19:57 -0800

This is one of those times when it might be somewhat useful to know your gender beforehand.

By: sourwookie

sourwookie — Fri, 08 Feb 2008 15:35:41 -0800

Treat her like a hooker for added realism.

By: Brandon Blatcher

Brandon Blatcher — Fri, 08 Feb 2008 15:49:40 -0800

So, if you were setting this role play up, what would you do?

I'd ask her what she was looking for from this fantasy i.e. a certain tone of voice, language, action etc, then proceed to do exactly that (and a little more).

It's nice that you want to surprise her, but if *I* don't know her like you do, so asking me about what to do with her has a bigger risk of falling flat than if you asked her yourself, see?

By: jessamyn

jessamyn — Fri, 08 Feb 2008 15:56:04 -0800

If you are a dude, I think you could really rock some of those button-front pants. They're totally made to highlight the assets of aroused sailors. Otherwise I'd say knots, a stripey shirt, and rum lots of rum. Try to make a decent double entendre about SEXtants.

By: bondcliff

bondcliff — Fri, 08 Feb 2008 16:05:42 -0800

No matter what, make sure you eat some spinach.

By: megatherium

megatherium — Fri, 08 Feb 2008 16:07:28 -0800

Don't forget the barrel. Sailors love barrels.

By: kalimac

kalimac — Fri, 08 Feb 2008 16:19:02 -0800

knots, ropes, lots of double entendres involving splicing the mainbrace and nailing your colors to the mast. Be aware that half of everything on a ship is named after a part of female anatomy* -- presumably after being at sea for awhile one got a little sex-starved :)

But, also, what others said -- find out what she thinks a sailor is.

*My favorite is the valley between strands in a rope, named the contline. Say it real fast, and squint and you'll see what it looked like to a lonely sailor...

By: Forktine

Forktine — Fri, 08 Feb 2008 16:25:26 -0800

there is a masculine way to dress like a sailor and it doesn't involve shorts

This bears repeating.

But there are too many unknowns here -- are you male or female? Would her world be rocked by you showing up in the gayest, YMCA-singing, tight-short-wearing, Tom of Finland-approved sailor costume because she thinks gender-queer sex is hawt hawt hawt? Or is she really imagining Johnny Depp carrying her off on his pirate ship? Does she want to be the cabin boy, or the girl-in-every-port, or the secret stowaway discovered mid-voyage? Cat-o'-nine-tails and knotted ropes, or South Pacific hijinks?

If I were you (and keeping all these unknowables in mind), I would go do some shopping at both military surplus stores and some marine equipment supply places. Some combination of the clothes and some snazzy sailor gear might do the trick. If you have the cash, renting a houseboat or a cabin cruiser for the night could set the scene in a big way. And I think you need to find the right music -- my first thought is that "Rum Sodomy and the Lash" album, but there is probably much more nautical music available. And films: Master and Commander (the title alone might do the trick); The Perfect Storm; The Hunt for Red October; etc.

By: Blue Buddha

Blue Buddha — Fri, 08 Feb 2008 16:35:19 -0800

Eye patch and parrot on your shoulder. Arrrr!

By: iamkimiam

iamkimiam — Fri, 08 Feb 2008 16:46:12 -0800

Don't forget to get sloshed too!

By: tomboko

tomboko — Fri, 08 Feb 2008 17:07:15 -0800

I think it's what ironmouth said. The point is not costume, it's voraciousness. You've been at sea for a long time. You're horny. So horny. Run with that.

By: driley

driley — Fri, 08 Feb 2008 17:09:01 -0800

I think it is important to note that whatever your lady friend may have said, she doesn't want you to be a sailor for a night. She has a fantasy about a sailor she would like to play out with you.

Talk to her about this. Express your appreciation for her openness and tell her how much excites you to have this opportunity to play. Ask her what she imagines happening. Ask her what about sailors is sexy. As her who she wants to be when you play sailor.

Pay close attention.

Tiny details are often powerful in long term fantasies.

By: lampoil

lampoil — Fri, 08 Feb 2008 18:58:45 -0800

Here's what I'd do. Keep the shorts if you think she'll like them, but put them on under a more realistic sailor suit (if they'll fit--one of the great things about sailor pants is they are TIGHT). Go to Times Square. My first thought was to go during actual Fleet Week, but it may not be such a good idea to be around so many real sailors in a pretend or partly real naval uniform. I don't know. Anyway, go when it's crowded, go separately, and...pick each other up.

Then go somewhere and do it.

By: mamaraks

mamaraks — Fri, 08 Feb 2008 19:03:38 -0800

Beforeheand make sure to cook her supper. It would have to be lobster or crab. Something from the sea. I don't know about anything else. Don't bathe for a couple days so you are stinky like a sweaty hardworking sailor?

By: mamaraks

mamaraks — Fri, 08 Feb 2008 19:04:10 -0800

Beforehand, that was supposed to be.

By: melissam

melissam — Fri, 08 Feb 2008 19:32:24 -0800

Eeew, not Popeye/Gilligan sailor. Rent Master & Commander or Horatio Hornblower (the miniseries). Those are key movies for women with things for sailors.

By: AccordionGuy

AccordionGuy — Fri, 08 Feb 2008 20:43:34 -0800

Do not use any nautical term as your safe word.

By: bendy

bendy — Fri, 08 Feb 2008 23:33:41 -0800

Also, swear like a sailor. (?)

By: kidsleepy

kidsleepy — Sun, 10 Feb 2008 19:39:34 -0800

!! the shorts were perfect !!

By: iamkimiam

iamkimiam — Mon, 11 Feb 2008 00:18:22 -0800

I love happy endings!

By: thetenthstory

thetenthstory — Mon, 11 Feb 2008 16:05:57 -0800

As the OP, yes she loved the shorts. I came out in my little white salior hat and shorts and got right to it. She laughed at first (with enjoyment) but still loved it. It was a pretty hottt time. I'm glad she doesn't live near any ports.

She wanted to wear the hat.

Thanks for all of the comments. I think maybe next time I'll take it to the next level with the knots and full white suit.