Boyfriend wearing womens clothes?

[Faris]

He's a lumberjack, isn't he? He's okay, don't worry about it.

[blackmage_nuke]

Just earlier I was wondering if there was a way to reduce bots in this forum but no I realise we'd be missing out on gems like this

[escobert]

My boyfriend has come to me with a rather unique request. He tells me that his number one fantasy is to dress up in women's clothes and he wants me to surprise him with something to wear. He says that he would prefer something along the lines of a dress or a french maid's uniform. He also says that he wants to wear a pair of panties or other women's underwear that will be extremely uncomfortable and painful to his testicles.

I have come here looking for advice. I am going to honor his request, but could members of this forum please help me out by recommending certain clothes items that I should force my boyfriend to wear? Please link to any such items on Amazon and I will look through your suggestions, and purchase from them. I really appreciate the help, thank you so much!

Right. So naturally the first place that comes to mind to get advice for this is a freakin' Final Fantasy message board.

Sic transit gloria mundi.

Aren't we all here because our lovers like to wear the opposite sex's clothing?

[DMKA]

He's a lumberjack, isn't he? He's okay, don't worry about it.

But...does he also like to press wildflowers and hang out in bars?

[The Man]

Dear Sir,


I wish to complain in the strongest possible terms about the previous entry in this thread about the lumberjack who wears women's clothes. Some of my best friends are lumberjacks, and only a few of them are transvestites.


Yours faithfully,
Brigadier Sir Charles Arthur Strong (Mrs.)


P.S.: I have never kissed the editor of the Radio Times.

[Madame Adequate]

Well Britt, speaking from experience there are really two things to consider here. One is discomfort and the other is humiliation. Now to some extent you're liable to get a bit of both in any forced crossdressing play, but it's better to confirm beforehand what sort of experience he's looking for. You'll also need to decide, based on that and on what sort of situation you want to see him in, what angle you're going for. Is this something he'll wear for a little while in the bedroom? Are you going to make him wear an outfit all day long? Is this something you're going to do regularly or rarely or just the once or what? Are you just going to stick him in some clothes, or are you actually going to try and make him look feminine and do his hair and makeup and stuff?

Now, you've got a whole raft of options on what to make him wear based on what you decide with the above. It sounds like he wants plenty of discomfort which is good, because that gives us more options. You could start with light stuff like making him wear regular everyday clothes, jeans and a t-shirt, in women's sizes. You could substitute that for a skirt and blouse, much more obviously womanly but still fairly tame. Then we get into things like dresses and the like, which can really start off very simple and get to being very elaborate and expensive, depending on your taste and means. The other angle, as you suggest in the OP, is to go for things that are pretty much always fetishized and sexualized when worn. A french maid's outfit is an excellent example. You can look at other outfits like of a schoolgirl or secretary, pretty much any stereotypically female role works, especially one seen as subservient or submissive.

The last part of the equation is to sell the scenario and the role. If you dress him up as a chick and then you guys go about your day as normal, that may not be what he's looking for. You've got to dress him up in a certain way, then treat him appropriate to that outfit and as a girl. Dress him as a french maid and make him clean the house. Put him in a cute, frilly dress, feminize his name (e.g. "Paul" into "Paula", "Dan" into "Danielle", "Steve" into "Steph" and so on) and make him act like a stereotypical housewife, making your dinner, getting you something to drink, that sort of thing. Or just dress him like a schoolgirl, get a big black strapon, and take his butt virginity.

You can also spice things up with toys and the like! Consider things like buttplugs, gags, ankle and wrist cuffs, and so on. If she's naughty and doesn't do as you ask, throw her over your knee and give her some stern discipline with a riding crop or a paddle. If she continues to misbehave lock her in a chastity belt and tell her she's not getting out until you're satisfied with her behavior. It's kind of hard to get underwear that would give much testicular discomfort for long because anything too tight like that will just ride down a bit until it's a better fit. Still, lady's underwear is sexy and pleasant to wear so get him into some right away! Make him wear a sheer thong under his regular clothes.

I hope this helps give you some ideas and that you and your boyfriend can have lots of hot, sexy sissified times together

[Mirage]

Skirts are just really comfortable to walk around in.

Just FYI.

[Psychotic]

He also says that he wants to wear a pair of panties or other women's underwear that will be extremely uncomfortable and painful to his testicles.

Ohhhhh, now I know who your boyfriend is.

[Shorty]

Is it Juliebird?

[Iceglow]

I'm sure View Profile: Iceglow - Eyes on Final Fantasy Forums <----this guy can help you.

Crass, unimaginative and plain wrong. When it comes to this subject I think it's definitely got to be covered by Hux he has the most experience in this, one of these days you might learn.

(e.g. "Paul" into "Paula", "Dan" into "Danielle", "Steve" into "Steph" and so on)

Well played sir, Well played.

[Psychotic]

Is it Juliebird?

It's this guy.

http://home.eyesonff.com/eyes-each-o...other-day.html
http://home.eyesonff.com/eyes-each-o...ice-girls.html
http://home.eyesonff.com/girly-forum...s-allowed.html

No word of a lie folks, it is actually him.

[Clo]

This another opportunity for Clo to go, "Strap ons?"

Maybe he'd like a new perspective there too~

[Aulayna]

Is it Juliebird?

It's this guy.

http://home.eyesonff.com/eyes-each-o...other-day.html
http://home.eyesonff.com/eyes-each-o...ice-girls.html
http://home.eyesonff.com/girly-forum...s-allowed.html

No word of a lie folks, it is actually him.

Wow that guy trolls here too... I remember him from FFR.

(Actually considering Aaron was both here and there it makes sense )

[Tigmafuzz]

He's a lumberjack, isn't he? He's okay, don't worry about it.

But...does he also like to press wildflowers and hang out in bars?

He probably wishes he were a girlie, just like his dear papa.

This thread. This thread is EoFF in a nutshell.

A bunch of crossdressers? Whatever floats your boat I suppose.

What's wrong with crossdressers?

[Mirage]

Yeah, what's?