Would he joke about cross dressing if he didn't really want to do it?

[liv2802]

My boyfriend has said a few things in the past (mostly in a jokey way but last time a bit more seriously) about wanting to cross dress and I'm wondering if people think this is something a man would joke about if he didn't actually have a desire to do it? It would totally turn me on if he did want to do it (well the clothes at least not neccessarily hair and make up) but I don't want to bring up the topic seriously until I'm sure he's not joking in case he thinks I'm completely mad or gets offended... he is a pretty masculine guy in most ways but is definitely in touch with his feminine side..

[Melissa73]

hello, speaking from experience, as i just came out to my wife....i tried to joke to her about dressing up, hoping she'd catch on and encourage me! MAybe its way of seeing how you feel about it! What i recommend is to be open and sit down and talk w/ him in a calm and rationale way.... no one having the advantage!


melissa

[ClosetED]

Details would help, but my impression is that he is serious. If you are OK with some of it, then use it to run the show and allow only what you want with clear rules. If he does want to do it, he will be in heaven and give no arguments. You could do it as a bet that if he loses, he has to put on some clothes. See how hard he tries to lose! If he really tries to win, you can do very minimal with the clothing.

[Annaliese]

Give him time be positive about Crossdressing when possible and see what happens most of are masculine when in male mode. If he is a CD he is lucky to have someone like you.

Hugs

[Jill]

Oh yeah, I would always joke about it with people to test the waters. Though it's not a guarantee that he does, it's a strong indicator. Next time he jokes about it, throw it back at him and tell him to do it, dare him too and then you'll probably have your answer.

[kimdl93]

Why not coax him into some lingerie as a bedroom game. See what happens.

[Stephanie Miller]

Be carefull what you wish for. Once the "Jennie" is out of the bottle..... you may get the hair and makeup as well- PLUS MORE!

But if your adamant to push the boundaries then I think Jill could be right. Next time he brings it up - tell him he doesn't have what it take to crossdress. Then dare him to dress up for the evening (in private of course) or take you out to a VERY nice place to eat. You win either way

[Jenniferathome]

He's not joking. In all likelihood, he is praying you will suggest it. So go ahead. HOWEVER, you two need to have a serious discussion about what cross dressing is to him and to you. Don't assume. Good luck

[Cheryl T]

I tried the joking routine when I was dating my wife. I made mention of different things depending on the situation trying to get her to suggest that I dress in something and then go from there. It failed miserably as she didn't take my hints.
If you think that's the reason for the jokes you are probably correct....why not just ask him. What's the worst that he can say when you tell him it might turn you on....???

[sandra-leigh]

He might be embarrassed to actually crossdress, and it can be difficult to tell real objections from false protests.

There are some subtle tests than can be made. For example, if he knows the difference between various kinds of bras, he's Thought About It Too Much

[Wildaboutheels]

I'd suggest a back door approach to offer him "opportunity" for discussion and that way the ball is in his court. BUT, as already mentioned, once the barn doors are open, you might not be able to get them shut... These Forums are bulging with such stories. He might not be willing to "settle" for "just the clothes"

Try wearing something obviously male "looking" around him at an odd time or two to open up the subject of clothing choice. One of his clothing items is an obvious choice. Or you could pick up any # of male items at a thrift store for 2 or 3 bucks, maybe something like a flannel shirt.

And NO ONE can read minds. NO ONE knows his true intent for the comments he has recently made except him.

[Kelley]

There is an old saying

Many a truth is said in jest

[Jana]

Sounds like he's trying to drop you a hint. Offer to do his makeup for him, see what he says.

[Lady Catherine]

I used to joke about it all the time. There's some some good advice being offerred to you here. I'd say next time he "jokes" about it, tell him to "just do it already" and see what happens. Good luck.

[goodnhose]

Yes! Yes!!!.... He wants you to ask him to dress. Let us know how it plays out.

[sissystephanie]

Any man who jokes about crossdressing either already is a crossdresser or wants to be!! I told my late wife that I was a crossdresser when I proposed to her. Her response was, "do you go out in public dressed as a woman?" i told her that I did but that i was not very good with makeup and fixing my wig. She told me that she could help with both those things, and that she would enjoy having a husband who would also be her girlfriend!! We had almost 50 happy years together before cancer took her.

You need to have sitdown conversatiobn with him about what he wants to do. As has been said, let us know what happens!

[wilt575]

He might be embarrassed to actually crossdress, and it can be difficult to tell real objections from false protests.

There are some subtle tests than can be made. For example, if he knows the difference between various kinds of bras, he's Thought About It Too Much

I wasn't embarrassed to do it just, embarrassed to admit it and used false protests as a front. She got me into clothing disscussinos when shopping a few times, because we are same size(one size different) and a few comments made. I guess she put 2and2 together, because one day some how a couple of multi-striped bikini panties an polka dot hipster panties showed up in my underwear drawer and lifes been wonderfull ever since.

[docrobbysherry]

Any man who jokes about crossdressing either already is a crossdresser or wants to be!! I told my late wife that I was a crossdresser when I proposed to her. Her response was, "do you go out in public dressed as a woman?" i told her that I did but that i was not very good with makeup and fixing my wig. She told me that she could help with both those things, and that she would enjoy having a husband who would also be her girlfriend!! We had almost 50 happy years together before cancer took her.

You need to have sitdown conversatiobn with him about what he wants to do. As has been said, let us know what happens!

Absolutely what Steph said! Before I began dressing out of the blue at age 50, it never occurred to me to even try on women's things. Much less joke with my dates or SO's about it! He's either TG, or "TG curious"!

[Nikki_C]

Yes, he definitely want to try or is already a CD.

BTW, I am still in the closet...

I told my wife last night (jokingly of course) that her high heel boots that she was wearing is very cute. And i need a pair just like it. And we need to go shopping to get me a pair...

We'll see where that take us in a few weeks...

[Kate Simmons]

I don't take myself that seriously and joke about it all the time. BTW, how many crossdressers does it take to change a light bulb?

[~Joanne~]

Chances are he is most certainly testing the water with you. Geez, there's that pesky "test" again lol . I agree with the other girls, he is probably a closeted dresser now and trying to find way to bring it up to you. I also agree that once the genie is out of the bottle, it can never go back so you have to decide if this really is a part of your life that you want. Lay some stuff on the bed and when he asks tell him they are for him, try it on. He will either do it or he'll move back towards the closet.

BTW, welcome to the forum Your the third GG to join this week....hmmmmm......

[BRANDYJ]

He's hoping you take the hint and either ask him if he wants to wear women's clothes or that you will ask him to put something of yours on, perhaps during a playful love making session.
If a man is always joking about it, he is afraid to just come out and tell you what he likes or wants to do. He's hoping you will take the lead.

He is not going to think you're at all. I would not worry about that. Remember, he's the one that keeps bringing it up in his joking manner. And NO WAY will he be offended. He's going to see you want to please him in a sexy playful way.

Just ask him. What's wrong with being open and honest? And don't be afraid to tell him it would totally turn you on. I promise you, that confession will totally turn him on.

[Beverley Sims]

Get him to sleep over one night and lend him your pajamas.
I have let myself be connived into that situation on more than one occasion.

[TGMarla]

Well, I guess there's no way of really knowing an answer to this, except for you to push the envelope a bit. If you think it would be a turn-on to you, then try enticing him with something lacy. If he likes it, you have your answer.

[Jorja]

Christmas is coming! A cute pair of panties in his size might get things rolling.