How to get your boyfriend to Crossdress?

[Bumblebeeurgurl]

Okay. So I guess some advice or insight would be great. I'm a 23 year old female who has a bit of a crossdress fetish....but my boyfriend.... We have been dating for only a few months and I really am crazy about him. He is aware that I am into many different kinks and fetishes. The hard part is that, he has told me all his other past girlfriends have been prude and snobby girls. He tells me all the time he appreciates me because I'm Not like that, but still has some sexual boundaries for me. (Like no butt stuff on him or dressing up). He does have a pleasing personality and I think maybe one day I could ease him into it, but at the same time, I don't want to freak him out or push him away, but I really miss having no sexual limitations and boundaries. I clearly have many more sexual experiences under my belt and a bit more of an open mind. Is it possible to break that mentality of his and maybe get him to remove these boundaries or is getting a man to crossdress when he doesnt want to, a mentality that cannot really be pushed? I asked once and he told me it would feel like he handed over his "man card" which I don't agree with but don't want to fight him on things that he feels, especially if it makes him feel uncomfortable. Since then, he often asks how he can please me more and I don't bring up the subject anymore since he told me his limits....but I want more from him without making him uncomfortable or freaked out. What should I do? Thanks for the help. :daydreaming:

[Angie G]

I can't see why anyone wouldn't jump at the chance to dress for his girl. WTF if it would make her happy. Sorry Bumblebee I don't know what to tell you hun.Hugs.
Angie

[Tracii G]

Welcome first off.
You know you shouldn't force something on a person you are in a relationship with right?
You should know you can't change a person as well I hope, as much as you want to its not fair to that person.
Maybe in time he may loosen up with his sexuality and be ready to try different things.
The main thing is don't push too hard this early in the relationship if you really like the guy.
Most guys think a guy that crossdresses is gay or perverted or just not right in the head so keep that in mind.
If the guy is not fulfilling your needs then search for one that will.
Good luck.

[Heidi Stevens]

Hey BB, I'm going to pass on the same advice we give single guys here looking for a girlfriend that will allow and even help with their crossdressing: Keep looking until you find one that is agreeable to your requests. If your current boyfriend is not into crossdressing, it's going to be tough to keep him going even if you do get him to try it. Either you like it or you don't, there are very few men trying CD after their teens if you've never had some previous thoughts of doing it.
I'd say if your really wanting to get a guy to share CDing with you, time to cut your losses and rebait your hook for a willing guy. Be sure to ask the new guy early in the relationship you want him to CD. It's what we advise our members to do with potential girlfriends and wives.
They are out there, just keep looking and asking. When you do find a willing boyfriend, he'll gladly join you in having fun.
Good luck!

[Bumblebeeurgurl]

Sorry but leaving him is just out of the question. I care about him way too much. And you're right I don't want to change his mentality or make him uncomfortable. Just wondering if him trying it or being into it might be a possibility? If he can't deliver that, that's okay. But frankly, this is only a small speed bumps when it comes to the relationship. Being single for 3 years after an awful heartbreak, I definitely did some sexual exploring when it came to myself. But I couldn't break up with him over something like that. The sex is still fantastic and I've never had a guy that was as crazy about me, as I am with him! He is a rarity I thought I'd given up on finding. Just really wanting to know if its possible a partner might open to things like that if his partner is into it or if it's something a man decides and does on his own? Either way no matter what, I'll still be here. I wouldn't let a great guy go just because I'm a little more kinky in the bedroom because of more experiences.

[Nikki.]

op, you may be legit but color me skeptical....you posted just about every single (not in a monogamous relationship)hetero cd's fantasy on the homeroom whiteboard...

[Teresa]

Bumble,
If he's not wired that way it may not mean anything to him, I'm sure it won't put him off you but maybe you'll have to find something else that turns him on.

As CDers most of us would jump at the chance!
If you still insist, start with suggesting how he might look in your panties, assuming you're about the same size . If he's aroused by this then you'll know he'll be OK , I suggest you don't force him into a bra but he may go for a suspender belt and stockings, they usually turn most men on ! If he starts to back off let him think about it , he may just come back after a while and try it again.

[PaulaQ]

@OP - you are unlikely to do this unless he's already a CD or he is exceedingly submissive. And even then, probably only if he's a CD. Good luck though.

[giuseppina]

You might make suggestions about what this does for you, BB. ;)

[Brynna M]

Bumble

Just like a can't make a crossdresser completely turn off that aspect of themselves you can't push it into someones personality either. That said the only thing i can think is that if he is open to it at all he will need to feel very safe with you before he goes there. For reasons we as a society may never understand a man in womens clothes(for whatever purpose) is more taboo than most sexual fetishes I can think of. (Male "bottom" sex being another)
If (and that is IF) he has an openness to dressing all you can do is show him (not just tell him), a lot, that you never think less of men who aren't traditionally manly and that you would never betray any secret (his or anyone else's)

[Robin414]

Welcome to the forum Bumble B Girl!

Being gender fluid and a raging CD I'll start by saying...WHAAAAT!! 😀😀

Stepping over the 'blue line' (ya, hockey reference) though, I think when you're in a relationship BOTH parties should step up and indulge the others fantasies and fetishes, I can only see that making a much stronger relationship!

I'm speaking as a full on guy right now: asking a dude to 'dress en femme' to 'set the bedroom on fire', I think most 20 something yr old guys dating an open minded young lady would wear whatever you want them to, you do realize at this point in time you're holding all the cards right 😀

That said though, if he's not TG (and I use the term on its loosest meaning), I'm pretty sure you won't be able to convert him, anymore than making a gay guy heterosexual. Of THAT'S your goal (which is totally cool), expectations might need some adjustment (which is totally cool as well).

[IamWren]

Hi Bumble B... welcome to the forum.

I'll add a bit more to what Paula Q said. What you're asking is the equivalent of asking "how can I turn my friend lesbian so I can hook up with her?"

Unless your friend had been repressing her true sexual preference no amount of suggesting is going to have her be a lesbian.

Same thing with a CDer. Unless he's already got a proclivity toward it, I think the chances are quite slim.

[emma-louise]

I smell a troll

[Mayo]

The 'man card' / 'no butt stuff' suggests to me he has some pretty rigid ideas about masculinity, in which case he's not going to be interested at all in anything that calls that into question - which crossdressing definitely does. We all know that CDing 'doesn't make you gay' but I doubt he'll see it that way.

[Mollyanne]

I should have met you first!!!!!!

Molly

[Ressie]

The thing to do is to get him to tell you what his fantasies are. This isn't one of them.

[Alyssa Lane]

I would say talking out in the open about any sexual fantasies that he has and possibly doing that for him, even if you are not peticular about doing it either. Then you could bring up what you like to do, and explain what you like that might be kinky, etc. Its a 2 way street, maybe he likes the normal stuff, schoolgirl, etc. It might take time for him to trust in you that he will stay macho like society has most guys. Once that trust comes around, which takes time, could be a year or more. Then you will know. Right now it still sounds early.

[phili]

I'll add that he is already pretty clear and communicative and honest, if he says he doesn't want to hand over his man card! I would shift the conversation to address the twin goals of being able to explore gender roles more freely WITHOUT losing the safety of the man card. The whole gender enforcement thing works on kids by threatening their safety if they don't conform to the gender role given them, and then this unfortunately turns into deep fear of the unknown- what will happen to me if I let down my guard and cross the line? He may have picked you because he wants to be free, but he doesn't want to be unsafe. He can't feel that you own him the way many men tend to feel they own their women, parents own their children, etc. He can feel excited to be free and explore- if he can get back to safe territory. He also will want to understand exactly what you want from the experience- and wonder if you are actually a lesbian but haven't figured it out. So my suggestion is to give him a lot more info about you, and keep the requests very small and clear- like "I love it when you look at me in my underwear, and I love the privilege of wearing such frankly sexy underthings." Wait for a response. "I don't think it's fair that only women get to do this. I don't think it detracts from men's sexiness to have sensual clothes." Wait a week. "I've been thinking, le's break the mold, safely. " Wait.

If you like him for who he is outside the bedroom, then make sure that gets 95% of your attention and keep the special requests incidental. The right moment will appear for "Would you indulge a fantasy for me?" Wait. Then choose one which lets him feel he is doing you a favor, as a man would. He may very well wish to try sensual sexy underthings but it is just too unsafe to admit it to consciousness in any way except an incidental,casual, goofy experience done in playtime with you. If you can make it a humorous and clowning goofy time together with no hint of seriousness, that will help break the ice.

It has to happen incrementally and feel manly. It could take months to feel safe acknowledging 'OMG I just enjoyed wearing stockings and garter belt' and not be drowned out by the social fears and years of gender enforcement messages.

Sounds like a lot of work, but that's what long term relationships require!

[sherri]

First, you need to realize, if you don't already, how ingrained in our male culture is the abhorrence of anything that could even remotely be perceived as being a "sissy". Even if a guy secretly had such an inclination, his fear of perception by his peers would trigger powerful suppression. Second, odds are high your bf just isn't wired that way. I know I have to remind myself occasionally, because femininity comes so naturally to me, that I'm not "typical", that I am in fact a member of a small minority. I've heard it argued that we all have the potential for gender fluidity in us, but I don't particularly buy that, and even if it were true, the majority are content with the normal gender dichotomy and feel no particular need to question or experiment with the biological scheme of things. In other words, your bf's attitude is prolly if it ain't broke, don't fix it.

That said, I'd love to hear more about what it is about CDs that you find appealing, and how you would like to see it play out.

[Jane G]

From my experience the vast majority of cd's are born this way. Takes some a while to find out. Leave it in the back ground. Love your partner for who they are. If they love you as much then over time there are adjustments even compromises. Pushing one sides ajenda too far is only possible for a short time. Leave a trail for him to follow if and when.
, But don't try to change who he is. That only ever goes one way.

[Jenniferathome]

If he's not a cross dresser, he won't want to do it at all. You're not asking him to get kinky with you, you're asking him to be uncomfortable. It's just not going to work.

[Alexa CD]

What Sherri said was quite good, and even if it is only between you and him he still may suppress the idea. You know not to put pressure on him or reconsider your relationship and I think you understand the dynamics of the relationship and what is possible far beyond what you could explain here for us to give any kind of worthy advise. Just don't take him out of his comfort zone or change what you already have, don't make it weird you know. I get that you want to play around and experiment or whatever though so work on it and figure him out, who knows maybe you can bring him around to the idea you're just going to have to be patient and come up with a strategy or something to get him into it. If it's something you want and he knows that you could win him over eventually. Good luck I guess!

[Stephanie47]

Wait for Halloween. Then suggest you and your boyfriend should go out as 'switch dates.' Get him all excited, then take him home and have your way with him.

[docrobbysherry]

This is a communication issue. U r both too young to appreciate how important this is in successful relationships.

Instead of asking someone to do something, u need to openy and calmly discuss both your feelings, wants, desires, and bedroom kinks. During such an intimate discussion u should feel free to mention your fantasy of making love with a man in a bra and panties. Or, with nylons and a garter belt. Or, whatever your fantasy is that turns u on! Men like turning on a woman. So, eventually he may feel comfortable, or drunk, enuff to want to try it with u!:D

Then, if he enjoys it, too? Your on your way!:o

[stormy_skyxx]

that would be my dream, having a partner who supports or even help me into crossdressing.....
that said, i fully agree with docrobbysherry.
Things should be discussed calmly, and since it appears you love each other a lot, when love is around , that can solve many things.
wish you both best of luck, happiness...and more than everything , true and genuine love

[Alaina R]

Pretty unusual request but I know there are some few women who get off on male CDing so I'll assume you are one of them. Some people consider themselves born crossdressers, others come to it from life experiences or to fill some psycho-sexual need. I know for me part of the turn on is that my dressing is pleasing and/or exciting to my wife/partner. I guess you can try doing it a little bit with him while involved in other sex play and see where it goes. If he gets a really good reaction from you when he wears a piece of lingerie for example, and that reaction from you allows him to have extra fun, he may go with it to some extent. Young guys like sex and he wants to please you so I suspect over time he will try more stuff for you. Still, he may never be into it as much as you.

[Bumblebeeurgurl]

These are all fantastic. I appreciate the insight and help. Lol and no I'm not a troll. Hahaha. I'm pansexual so it's truly about the person. However, to the person that asked. It's something that I fantasized about and then when I tried it, I loved the experience it turned me on so much!;and then I found myself wanting it more and hoping it would happen again. As for the communication, that is a big thing for us and I'm really happy about that. Thank you for all your insight and advice. He told me he is open to try things and explore with one another and that it's hard to answer what he likes since he has not really had the chance to explore that too much. But he says he is open to try things and maybe ease into them so who knows and yes lol he is into the schoolgirl stuff. ;) lol so if I dress up for him maybe he will for me lololol. :D

[binair10]

Hi,If it is getting to you you could always say that when you were out shopping you saw a good looking young Cross Dresser.

You could drop it out in conversation...like have you ever thought about dressing up in female clothes?.

When he asks you how you can please him more...would you like me to dress you up as a girl?.

There are many ways to`drop the hint.

Let us know how you get on.

Julie.xx.`

[Fiona123]

I would jump for joy if my spouse asked me to crossdress. My advice would be just ask, you may be surprised at the answer.🌺

[Thictoria]

Hi bb, I'd just ask him and if he response well buy him some lace girl boxers and get him to wear them out! Go slow and he might get into it but if not at least you tried ��

[ReineD]

Have you thought of joining fetlife.com? It's a great site for kinksters and there are lots of men there who are into dressing for kink. I was a member at one point, trying to learn more about dominatrix practices. They have local meetups and the people I met were very nice, respectful of boundaries. They are very clear, the site is not a meat market like CraigsList or purely meetup sites for sex. There was even a very large kink demo in a city not too far away, with vendors and a food fair, run much like an exhibition with lots of attendees of all persuasions. :)

If your bf isn't into kink, I don't think there's much you can do to persuade him otherwise.

[Lorileah]

When he asks you how you can please him more...would you like me to dress you up as a girl?.




Ummm...how you can please him more? I think something was missed there

[Scarlett Viktoria]

Although I started crossdressing later in life (late 20's) I'm very much a rarity. I wouldn't push the subject but be mindful, since it's a fetish for you, if it's something you can live without. So far it sounds like you can but uears down the line is it going to become an issue if you can't get it? But yeah, asking a guy to crossdress who's not into it is kind of a big a deal and he's not likely to go for it.

[Sometimes Steffi]

I would love it if my wife promised me more or better sex if I would only crossdress. But I was already converted well before I met my wife.

But I do have a couple of ideas. You could crossdress first for him. Ask to borrow his underwear, because you always wanted to know what it felt like. Put on his undershorts, dance around in them, and then just hop into bed with them on. Or something like that.

As for crossdressing him, instead of dressing him like a regular girl, try some coplay and get him a Japanese school girl costume, or wonder woman or X-(wo)man, something that he likes anyhow. And just go for the costume, no panties, and tights only if the costume requires them to be "authentic".

Good luck

[Joyce Swindell]

Of course if he likes to be dominated then he would have no choice....so I agree with who said you should find out what his buttons are and see if it can be worked in for the both of you. I also agree it's a communication thing. Do some internet surfing together and see what makes you both go OOoooooooo!?!?!

[Adelaide]

Sure wish my S.O. would be as open minded are you are. I'd be so happy.

[Jenniferathome]

Wait for Halloween. Then suggest you and your boyfriend should go out as 'switch dates.' Get him all excited, then take him home and have your way with him.

Nope. That won't work for the same reason it doesn't work on wives/gf in reverse. It is seen as a one off, not a trend.


... He told me he is open to try things and explore with one another and that it's hard to answer what he likes since he has not really had the chance to explore that too much. ...

Open to try "things" is not the same as open to cross dressing. "Things" tend to be sexual.


...You could drop it out in conversation...like have you ever thought about dressing up in female clothes?...

If he IS a cross dresser he might actually open up. If he is not, he'll be disgusted.


... But yeah, asking a guy to crossdress who's not into it is kind of a big a deal and he's not likely to go for it.

Not "likely" like as in 0%


...But I do hace a couple of ideas. You could crossdress first for him. Ask to borrow his under, because you always wanted to know what it felt like. Put on his undershorts, dance around in them, and then just hope into bed with them on. Or something like that....

Oh yeah, this is an idea... that will never work. He won't make any connection.

BB, you have one option only. Ask him. You have little chance of success given how few men are cross dressers, but there is about a 5% chance.

[nothingclever]

If he crossdressed for your sexual pleasures, that's sweet, but if he's not into it....I think it would be boring. A guy in a dress is a guy in a dress, a guy exploring his femininity is exciting and opens up all kinds of possibilities for both partners. Otherwise, it's just Halloween and might be fun once or twice, but not the same as having someone opening themselves up and sharing a part of their very selves with you....

[Margaux81]

Hi bumblebee im a straight CD and I can tell you how i got into the life. My ex kept bothering me about wearing her thongs .I resisted at first but finally caved it was cool but when she asked me to put on some leggings it blew my mind. it snowballed from there I now have more women's clothing then I do men's. so that's my advice tights ,leggings , silky things that are way different than what he is accustomed to and if that don't work out I'm single and looking for a down girl. just kidding and good luck.

[Sarasometimes]

You mention you have had partners who have met this desire and you seem to have a high priority on having a mate that is willing. If your need is high and his resistance to meeting this need is high, maybe dispite your "love" you may ultimately not be best for each other. I guess time will tell. If it is a "turnoff" or hard limit for him either accept it or move on. Is he aware of your self defined label of pansexual? Sort of an important bit for him to know.

[char GG]

Just be careful of what you wish for. It may not be what you think.

[larry]

Forget him. Just call me. hehehe

[Maxi]

I was the hard core macho redneck for many years. Never a thought of crossdressing. My first wife always slept in a slip, and when I went through my divorce, I bought a half slip. I slept with it like a security blanket. I found comfort in it. When I started dating, they would find it on the bed. There was always a question of who's is this, and I would tell them it's mine. Then one of the gals asked If I could put it on. After reluctantly putting it on, I was hooked on the feel, and slept in one every night. Maybe a fun night in bed, you could offer him a half slip, and ask if he would put it on for you. It worked for me.

[Georgette_USA]

To the OP Bumblebeeurgurl

This is an interesting area for me. Have NO thoughts on how to help you turn your BF. I know other women who are also into having a MtF CD/TG. They don't usually turn, but find ones that already are CD/TG.

I never thought of it as a kink/fetish. Being a MtF Post TS woman, always thought I shouldn't. Since finding other women with those feelings I have decided to pursue that also. I am a Lesbian with BI/Pansexual feelings also.

[Robin414]

...a guy exploring his femininity is exciting and opens up all kinds of possibilities for both partners. Otherwise, it's just Halloween and might be fun once or twice, but not the same as having someone opening themselves up and sharing a part of their very selves with you....

Wow NC, I sincerely hope you and your SO get back together (for their sake! intentional non gender specific 'plural' fau pa there again).

I'm a fan of Carl Jung myself and I believe to be truly masculine one needs to truly accept his feminine side, and vise versa! I kinda think you get it!!

[Maria_mtf]

I agree with Alex some very good points made. I say take it slow, see what he is willingly to do. Maybe explain that no one will know and he's got nothing to lose and he might even enjoy it. Ask him what his fantasy too and try that with him. Above all don't force it, experimenting should be fun for both people involved.

Do keep us updated I know I am curious of the outcome.