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 :devil:

[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 :heehee:

[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 :heehee:

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?:heehee::)

[~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. ;)

[Foxglove]

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..

I could envision a cisguy making a joke or two and not really meaning it. But since you say he's said "a few things in the past", I'd agree with everyone else that he's into it. I don't know that daring him to do it is the right approach, though. You might scare him off. He may really want to do it, but if you take that approach, he may not understand what you're on about and might back off. If you're really into it, you might try something like, "You know those things you've said about crossdressing. I don't know if you were serious or not, but if you were, I really don't mind. . ." and take it from there.

As others have pointed out, though, you may get more than you bargained for. He may not be into just the clothes. He might want the hair and make-up as well. So you have a decision to make. I wish you well, though, because it could be a lot of fun for both of you.

Annabelle

[Missy]

I work with some guys that joke about being gay lovers while at work. They both have girl friends. some may just joke about things like being crossdressing to being gay just to have fun with how others react. if you have any concerns either ask him up front about it or see how he reacts to you want him to wear pantie in any bedroom games you may come up with.

[carhill2mn]

My guess would be that he says that he is "joking" but would really like to but is not confident enough to actually initiate anything. Perhaps, you could respond positively (also in a "joking" manner) and see how he reacts. Many men would like to crossdress (at least a little) but, for many reasons, are hesitant to do so.

[DebbieL]

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..

He's giving you signals. Don't even wait for him to create another opening. Find something cute and sexy and tell him you want to see him in it. If he's a CD, he'll love you forever. If he's just a guy who thinks transgender issues are a joke, he'll be a sport and then let you know it's not his thing.

If he knows that you are accepting, and he's not sure, he might be more willing to share with you exactly how he feels. The reality is that most men don't joke about that with the woman they love unless they have some pretty strong feelings in that direction. At the same time, he's terrified that you will reject him. If he is transgendered, and he lets you know about how he really feels about his feminine side, about you, and about dressing, and you reject him, it could be something that has torn him apart inside before. Joking about it is his way of keeping it "Safe".

If he is CD and you know, you will also know what to give him at your "Private Christmas Party" - and every gift given to his feminine will be a gift directly from your heart that goes directly to his heart in the deepest and most wonderful way. Every time a wife or lover gave Debbie a present, it made the love so intense that I couldn't even think about giving up this wonderful woman.

If it would really turn you on for him to dress up, and he has zero interest in the idea, you might want to consider carefully whether you could be content with someone who only wanted to share his masculine side. I don't think this is an issue. If you have had bisexual desires, then having a wonderful man who can provide the best aspects of being a man, with the best aspects of being a woman - could be your dream come true.

If you really want his feelings, give him a pair of "your" panties (in his size), something very sexy and silky - and tell him to wear it the next time you get together. If you reach into his pants and he's wearing your silkies - you hit it on the nail. If he's wearing his jockey's then you will have to accept that he's just a masculine guy who thinks cross-dressing is a joke, and decide whether you want that kind of man in your life, and for how long.

Consider what else he jokes about. Does he joke that you're bossy and he likes it? He might want you to force him to dress, be dominant. Does he joke that he wants to spank you, or he needs a spanking? These are dimensions that could be added to the dressing. When men joke about sexuality, it's their way of sounding you out. If you had gone "ewww, gross" he would have dropped you like a hot potato within a week.

If he's joking with you like that, it also means that he's probably very serious about you. Most men know within 30 minutes if there is a big issue that isn't going to work, and he doesn't call you back. At this stage, he's trying to find out whether you can accept him by making suggestive statements as jokes, to see if it is safe to tell you more. If you are neutral, he will keep it a secret and it will be a struggle for him, but if you are positive in your response, and let him know that you like the idea, he's going to stop joking and get really honest with you.

I predict a very merry holiday season for both of you - together.

[deebra]

Jorga had a great idea, buy him a nice sexy pair of bikinni black panties, wrap them and ask him if he would wear them for you, it would really turn you on to see him in them. If he likes it and once he gets comfortable with you seeing him wear them buy him a bra, girl jeans and androgenist top and see if he will go a little further. I'll bet your sex life will go thru the roof. You suggesting him wearing something girly to bed will also make his day/night. You have to go at the right speed so not to scare him or embarass him. This trust ans acceptance from you will just make him be so much closer and more in love with you because of your acceptance. Turning you on is another big plus. But don't wait for Christmas, do it now. Bless you for having such a great attitude toward CDing.

[Eryn]

There are two people to whom he might be afraid to admit his true desires. Obviously you are one of these people. The other person is likely to be him!

CDers may be "born that way" but we often need quite a bit of coaxing before we will override society's supposed objection and admit to ourselves what we want to do. It took me over 50 years to take that step.

You can do your boyfriend a tremendous service by helping him to explore this part of himself. As others have suggested incorporating a bit of CDing into bedroom play might be a good way to broach the isse, but realize that for many of us CDing is not really a sexual thing. We dress as a form of self-expression.

In any case, your boyfriend is lucky to have a sensitive girlfriend who thinks of his welfare!

[DebbieL]

There are two people to whom he might be afraid to admit his true desires. Obviously you are one of these people. The other person is likely to be him!

If your boyfriend is Transgendered (CD, TV, or TS):

He may know, and he may have the secret desire, but even he doesn't know what he really wants. He sees you in a sexy outfit and he doesn't know whether he wants to make love to you, or to BE you. He wants your love, support, and acceptance more than you can imagine, yet he's terrified of his own desires, he has fought for years to keep it i


CDers may be "born that way" but we often need quite a bit of coaxing before we will override society's supposed objection and admit to ourselves what we want to do. It took me over 50 years to take that step.

Actually, the younger we were when we became aware of these issues, the more vulnerable we are. Imagine being 4-5 years old, having a bunch of friends you really liked, and suddenly, because you were a girl, you had to give up all of your friends and were never allowed to play with them again? Suppose that you then tried to make new friends and they ended up hitting you, throwing rocks at you, calling you names, kicking you, and hitting you with sticks or baseball bats. Imagine telling your dad you wanted to wear pants and he hit you, spanked you so hard you had blisters the next morning?

Imagine that when you got older and started dating, you told your boyfriend that you wanted to wear pants, and he not only called you a pervert but told all of his friends what a sicko you were, and his friends told all of their girl-friends and the other girls started holding you down and painting a mustache and beard on your face, with no time or place for you to wash it off. Imagine that the girls started cutting your hair really really short, again holding you down and making you look terrible.

Many of us have experienced very real violence, rejection, physical and emotional pain, and some have even been sexually assaulted - because we let the wrong person know we liked women's clothes.

For me, high school and even college, was like being a spy behind enemy lines. Knowing that if I was caught, I would be tortured, raped, and maybe even killed. The only solution was "trust no one".

When others joked like "whip me, beat me, make me wear a dress", I would laugh, and I would notice who else laughed, especially those who responded by flirting back. Those were the people I wanted as friends, the women I wanted to date. The women who reacted with responses like "how disgusting" immediately made my "avoid like the plague" list. With them, I could never let down my guard.

Even with those who seemed accepting, there was always the risk that if they found out, I would find myself the topic of the school gossip, and suddenly find that I would lose all my friends, couldn't get a date, and even my women friends would avoid me.


You can do your boyfriend a tremendous service by helping him to explore this part of himself. As others have suggested incorporating a bit of CDing into bedroom play might be a good way to broach the issue, but realize that for many of us CDing is not really a sexual thing. We dress as a form of self-expression.

This is important. Most of us will feel sexy and enjoy the sensations of the fabric, and can become very sexually aroused at the idea of being dressed up sexy and having a partner who sees us as sexy and beautiful, and many of us enjoy some of our first sexual experiences, including erections and first orgasms - while dressed, so sex will be exciting, and may get him to open up.

At the same time, the dressing may be an expression of his innermost self, and something that makes him feel very vulnerable. Some transgender men will feel so vulnerable that they are afraid to admit their feminine desires. For many of us, we struggle to accept until that day when we look in the mirror and see a beautiful girl staring back at us from the mirror. For many transgenders, puberty was like a death sentence, or worse life in prison without a chance of parole. Voices changed, hair grew where we didn't want it to grow, and we grew too large to wear the clothes of other women. The one consolation was sex, but even then, male sexuality seems so focused on "getting off" rather than enjoying the journey, the sensory experiences, and the emotional satisfaction. Many of us learn more about both male and female sexuality and how to please our partners, and we are aware of female orgasms, multiple orgasms, and other aspects, of female sexuality and sensuality. I loved the fantasy of being a woman, dressed in sexy clothes, being seduced by a woman in equally sexy clothes. For me, my favorite was both of us in office attire, wearing power skirt-suits.

However, I struggled for years over whether I was, or even could be, transsexual. From the time I was 4 until I was 12, I wanted more than anything to be a girl. When I went through puberty, I just assumed it wasn't practical, and assumed that there was no hope of change. By the time I was 24 and living with a woman I loved, I assumed, even hoped, that I would just have to be content with just keeping it in the bedroom. It wasn't until 10 years later, after being rejected by my own wife for 8 years, that I even began to consider going out in public, that I told another person, that I actually come out, and that I actually came out. After couple's counseling and therapy, I realized that I was transsexual - but even then there were consequences I couldn't accept. It took another 20 years to reach the point where it was again safe to even consider transition.


In any case, your boyfriend is lucky to have a sensitive girlfriend who thinks of his welfare!

Don't let me scare you. There is every chance that you and you boyfriend will find a wonderful and exciting way to share your mutual interest together, and there will be many opportunities to grow together and experience intense love you could never have shared otherwise.

[UNDERDRESSER]

Here's how i would deal with it in your shoes. Simply ask him, in a calm manner, at a time and place where he can be honest and straightforward, ( if he wants to be )

"So, this crossdressing that you want to try, do you just want to wear panties, do you want to try to pass in public, or something in between?"

Try to get him to be as honest as possible, and reasure him that you're NOT going to "out him " ( you're not, right? )

EDIT Oh! and PLEASE report back!

[Jacqueline Winona]

Most of us here would love to have a SO who thinks like you do :) And most of us would probably make a joke like this in hopes that you caught on. Nut for your specific situation, all I can say is observe some more, maybe make a few nonchalant hints of your own, then see what happens- you just don't have enough info right now to be sure.

[Pixiesmate]

I will admit to having tested the waters with jokes and off-hand comments to gauge my SO's reaction to the idea. She accepted the concept, jokingly at first, but then with a whole-hearted acceptance of the idea when she realized that I was only half joking. Since that time, we have been exploring my dressing and what it all means to both both of us. If you truly think he is trying to get a feel for your acceptance, then ask him what he has in mind, what he thinks he wants to do, and then tell him that you want to help him realize his dreams. He may have an idea, he may not, but either way the journey should be fun for both of you. Communication is the key, talking about each step before it is taken usually takes the pressure off, but doesn't reduce the massive case of the jitters he is going through. Be honest, expect him to be honest with you and go forth and explore this wide and wonderful world.

[MsJanessa]

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

That would be the way I would approach the subject---next time you are engaging in foreplay, ask him if he would like to wear your negligee (assuming it would fit--if not buy one to have on hand that would) or panties, or thigh high stockings---or maybe all three---if he says yes, I think you will be suprised and pleased at what developes between you two. You should tell him that you've always been fascinated by cross dressing males and are turned on by the idea and would really like to try it with him---I'm pretty sure he will be equally enthusiastic

[Lacey New]

The teasing and the joking is exactly how I tried to come out to my wife. I would test the waters and there were several times I put on her panties and asked her playfully "Is this how I have to get into your pants?" While the results of the teasing were good, the reaction to wearing panties was like a voyage on the Titanic. So, my guess is yes, your BF would love to dress.

So, I would recommend that next time you have an opportunity to respond to his joking, offer him some undies. I would bet a bikini that he will take you up on it and that the outcome will be pleasant for both of you. Then when it is all over, have a talk with him about his crossdressing and I'm sure that the two of you will come to a good place. I think the important thing though is if you want him to be honest with you, you need to let him know that he can trust you with his feelings and his (likely) secret.

Thanks for being here on this site. It is great to hear from caring and broad minded GGs who are willing to accept the feminine side of a guy. Your BF is lucky to have you.