How to get your boyfriend to Crossdress?

[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.

[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.