Possible questions to ask my CD guy

[Gabriella111]

So I just started dating a CD. We met at a party he was hosting. By the way he was dressed, which was very effeminate, I suspected, but amid our flirting and drinking, he told me flat out. It didn't faze me. He since told me and showed me a bit. He completely shaves everything (legs, arms, pits, and naughty bits) and he told me about a couple taboo fetishes he has. I find it all intriguing and very hot. He does crossfit, and I have a thing for thighs, so him in a pair of yoga pants... on a scale of one to even, I literally can't, haha. And he finds it utterly refreshing to be with someone who lets him be completely himself without judgment.

He doesn't CD in public because he said he hasn't had the support he needs. So I told him we should go on a date with him dressed up, so we're excited for that later this week. In the meantime, he's coming over tonight and I have questions but am not sure which to ask or how to ask some. I don't want to ask any that may offend him, so any feedback is helpful, just to know if these are okay to ask early on.

I know that he's completely straight. He's told me that he doesn't find men attractive and he very much loves women. He just also feels like he is one. So a lesbian in a very cute boy's body, is basically how we decided that was best explained. In that regard, I want to ask about his gender identity and if he has a female name that he's given himself. I feel like those are safe questions to ask.

I'm also curious about the origin of it. He's very much into youthful clothing, as is part of his fetishes. Frilly socks, cotton panties with bows, lace camis, pigtails, etc. For both him and it's what he finds sexy on a partner. He was explicit about not having any interest in doing anything with young girls, but fantasies and role playing, it's that genre. And I'm down with that, but I am curious is this is rooted in something from his childhood. This seems like maybe not a good question for early. Or maybe ever? I will say, though, that we have been very open in talking about both the good and bad in our lives, so I know for sure he is both open to sharing deep things about himself and feels safe doing so with me, and vise versa.

I guess that's the only questions I have at the moment. I'm really excited to get to know more about him and cross dressing and to be part of this experience with him. It seems others haven't been as open or accepting, so it's really great for us both.

[Pat]

Cool. By all means ask him if he has a fem name that he prefers to use when dressed and ask about the pronouns he prefers as well and if it's only when he's presenting female or all the time. It would be good to ask, if he knows the answer, if he perceives himself as transsexual (wants to transition to being a woman full-time) or non-binary (a mix of male and female) or something else. Origin stories are often fun if somewhat confusing and have to be recognized as part of a person's coming to terms with themselves, so they might not have a solid, factual basis as much as they are a statement of current understanding which may change/evolve over time.

The most important thing to remember, I think, is that a person who is transgender is transgender 24/7 every day of their lives. You've never experienced it and you'll never understand it from an experiential point of view, but you can come to understand it well enough if you use empathy and believe what he says is correct. TG folks get tired of having people who aren't TG trying to tell them what being TG is all about.

Have fun. Good luck to both of you.

[Fiona123]

Well said Jennie. Gabriella you sound like a treasure. Your CD friend is very lucky. 🌺

[Exris]

Im a little worried over this.

@The OP GG. If you like this person... please dont heap pressure on him/her (however that 'person' wishes to be addressed).

It will all come out to you when trust is gained. He sounds a little like a younger me. ALL my reactions have been negative. And noones even ever seen me dressed. My gay friend that knows I would rather be a woman... negative. And he's the godfather to my only child FFS. Still negative and Im in some kind of gaydome denial according to him.

The flatmate that caught a sideways glance at me in dress... very negative. Very very. But Iv fixed that one .. lol. That will NEVER be mentioned again Im very sure...

But anyways... go out with your new BF and have a good time. Dont press the issues. Dont inquire. Everything will unfold in a nice way if he's a good lad and you like each other. Let it be what it is.

[Teresa]

Gabriella,
A GG friend who helps in a bridal shop suggested we may revert to an adolescent girl , looking back I can relate to that, it's a stage many of us pass through.

I now feel having a femme name is no big deal, I hadn't thought about it until I needed one for the forum now I prefer to have one to go with my female side , it just feels right.

I was corrected for using the term male lesbian, it goes back to how my CDing started when my male and female became entwined with my sexual needs , I have no interest in men at all, I now use the term bi-gender, yes I do have GD it's something I've come to accept and learned to live with.

Also if it's any help to you I had two GFs before I married who were OK with my CDing, the last encouraged me because she knew how much it turned me on so she got the benefit , yes we did share clothes especially the nighties I'd bought for her !

Jennie,
That is a good point, my CDing needs are 24/7 and agree it goes with being TG.

[Jenniferathome]

Rather than some list, you should any and every question you feel you need answered in order to get involved with him. Nothing should be off limits, except for the time you ask, as you two have just started dating, I would think there are boundaries that are out of scope.

Would think the when, where, why are fair game and also how his cross dressing works into a relationship. Does he want to dress every day at home? Is that ok with you? You won't get all the answers in a day or week. Just keep talking.

[Ressie]

Rather than asking if the little girl thing is rooted in his childhood, just ask him how old he was when he first wore something of the opposite sex. Or ask how and/or why he started crossdressing. I think any of those questions will get him telling the whole story, or at least a good portion of it.

Most of us seem to love talking about how it started in childhood (except those late bloomers).

[Gabriella111]

Thank you all so much for responding. I will take all of this advice to heart.

He's had a mix of positive and negative responses. He was married and his wife was not supportive, so I'm excited for him to have met someone who embraces him for who he is. I'm the first person he's been with who immediately accepted him without reservations, and he has so far felt comfortable sharing more intimate details, and he said he's shared these things with me far sooner than he's ever shared them with anyone else before, so we're definitely on the road to building a strong trust. He's also dressed me up in what turns him on, which has been great fun. My own fantasies mesh well with his.

I don't mind if he cross dresses every day. He wears it well. I think he's hot when he dresses masculine, because he's a very handsome man. But there's a joy that he only exudes when he's dressed feminine, and that's beautiful to see. And he's also incredibly hot dressed as a woman, which is not something I knew turned me on. So that's exciting for me. He's also just a really wonderful person. I've just met him, but he's the best friend and roommate of one of my friends, and I've heard so many wonderful stories about him for nearly a year now. I just wish I'd met him sooner!

My reason for wanting to know more about the origins for the adolescent fantasy piece is that I have a teenage daughter. So I feel it prudent as a parent to ensure all is well in this situation as far as that goes. As I said, he assured me that he has no interest in actually being with young girls, but I obviously need to be sure.

And my apologies if my mention of "male lesbian" was untoward. I certainly meant no offense!

Thank you all again for the kind words and advice!

[Vickie_CDTV]

If you are wondering if he is a pedophile or something... probably not. There are some dressers who like to dress like young girls, and are not pedophiles.

Of course, you should always take precautions, especially when it comes to non-blood relatives (you are not married to) around your teenage girl. Your diligence is a good thing, in this day and age you just can't be too careful.

[donnalee]

The "Why do you do this?" question is one reason a great many of us are on this forum in the first place, so don't be surprised if he can't answer that one; he likely doesn't know himself.

[bridget thronton]

Welcome to the forum - your CD is very lucky to have found you ask anything you are curious about - but perhaps not all at once (and be patient your friend may not know how to answer some or your questions)

[S. Lisa Smith]

Welcome to the forum. I hope you stay an active member!! I can't add to the answers already given since they match what I would have said. I wish you great luck in this relationship and I hope yo both get what you are looking for!!

[Teresa]

Gabriella,
Please don't feel you need to apologise for using the wrong term, I was told by another member about a F/M TS who was labelled by her medical team as a male lesbian, sometimes the terms feel they make sense maybe we should stick to them.

I'm glad you are comfortable with the role play, it may not last but if it does no harm between the two of you why worry. The GF I mentioned was also OK with me in male mode but something kicked off in her when I was dressed, the outcome of the first time she saw me in a nightie was very special !

[Gabriella111]

Thank you all again. It all went really well. He was excited for me to ask him questions! And I am getting a better understanding for sure.

He identifies as male because that's how he presents to the world, for the most part. He has a masculine facial structure and doesn't feel like it's a reasonable expectation that he can make himself "cute" by society's standards. He said it may be something he puts greater effort into in the future, but he's okay with where he's at right now -- mostly just dressing at home or when he's going to spend time with friends at their place, etc. He sometimes will go to the grocery store or a fast food place if he's on his way to friends and needs to make a stop, but he's never trying to pass.

That said, he reiterated how excited he is to dress for our date. I offered to take him shopping and buy him a pretty top, because he noted he has a few nice skirts but hasn't really put any money into tops he could wear out, since that's not something he really does. So he's got mostly comfy girl clothes and said he isn't ready to get all dolled up to go out for the reasons mentioned above. So we're just going to both dress comfy rather than dress up for our date, so probably skinny jeans and a cute casual top and cute shoes, which is totally fine by me.

He does have a girl name for himself, though. A play on his middle name that he's always really liked. And he lit up when he told me about that! Super adorable.

I decided not to ask the origin question yet. I definitely will, and I think he'll be totally fine talking about it, even if he's not totally sure. He's a very open person and values communication and sharing. But his answers to my other questions were incredibly detailed, holding nothing back. So I got to hear a lot more about his past. It didn't go to his preadolescence but back to his teens. So there was some important information that helps me understand him better from that. Still, it all seemed like enough heaviness for one night, so I'm holding that question for later.

The other thing that came up... he told me the first night we were together that he ended his most recent relationship with an amazing woman primarily because he wants kids and she doesn't. And I was very honest in my response that I've BT;DT and don't want more. I was also very up front about being in a relationship with another guy currently (non-exclusive). So we agreed at the start that this could be a fun stepping stone for him, and I guess just a meaningful experience for me. Already, even though it's just been a few days, there are all the feels. And so now ... fears.

He's bargaining about his desire to have kids, which concerns me. This is huge for him and he's already like, "Well, maybe I'll change my mind. Maybe I can't even have kids! I've never had my count tested, so it could all be moot anyway." I immediately suggested getting that test. I in no way want to try to convince him he should abandon the idea. I don't think either of us had processed enough to continue that part of the conversation, so that's the number one thing for me right now.

We've had the benefit of being able to see each other every day and every night since we met, but that's about to slow down now that the holiday weekend is ending, and it's probably a good thing! It will allow some time for things to sink in and settle down. So I just told him, "Worst case scenario, we end up best friends, and I will always be here for you and go out with you." I think it was nice to hear, but I don't think it changed where he's at with it in his head, if that makes sense.


Apologies for being so verbose! I'm sort of processing "out loud" by sharing this all, which I find really helpful. Just writing it all down even, you know? And this is a lot for me, too. My guy goes out of town for the holidays, and just days later he's about to return and I've managed to find someone who I think is utterly amazing and have already developed feelings for... like, what? This has never happened to me, so I don't know where to even begin in handling this. We're not committed, so I'm not obligated to tell him, but... I don't know, it just feels weird, like keeping a secret I don't want to keep. I guess I'll just play it by ear!

[CONSUELO]

One thing you could think of doing is to conduct your own research into cross dressing and fetishism. There are many old threads here that would be useful and a large number of books are also available. Just search the online book stores under the headings of cross dressing, transvestism and fetishism and you will find a lot of resources. The better informed you are the better your ability to understand all that might be involved as this relationship matures.

[greeneyes]

Gabriella, It is so nice to read a post from another GG that seems to be like me. I am a newlywed and just found out about my husbands CD. I feel the same way as you. I am deeply attracted to him as a man but the energy he exudes when being able to dress as a woman is palpable. It can certainly make things hot. I think this just adds another intimate layer to the relationship that we would not have had otherwise. I get a great husband and girlfriend all rolled into one!!! I just wanted to say Hi and welcome to the forum. As far as good questions...I agree most of it will just roll out, just don't forget to be open and ask questions. Most of the time I think they have been dying to talk about this side of their personality, so they love being asked. Be open about your concerns when they come up, don't hold things back. Communication is key.

[Gabriella111]

Thank you both! Consuelo, I'm definitely reading up on it. I don't really have any concerns as far as the CDing goes. I'm mildly concerned about the age play, which is why the origin is important.

Greeneyes, that's awesome! I look forward to reading your posts!

He and I already have tons of plans. I've barely heard from my other guy as he travels for the holiday, so... I don't know. I think if he missed me and was excited to see me, that would have been communicated to me. So at the moment, I'm thinking I may just be focusing all my energy into this new relationship, which is more my style. We'll see how the next day plays out!

[Becky Blue]

Hi there and welcome Gabriella, you should tell him to come on here and see how lucky he is to have found you, you are a gem!!

[Tracy Irving]

Gabriella,

It is always exciting to meet someone new and even better when you like what you learn about them.

You seem to have good instincts so just follow your heart and do what feels right

Good luck to both of you

[Dana44]

Gabriella, Welcome to the site. He is a lucky guy to find you as you are a real gem to him., take it a bit slow on the questions but have a good talk with him as I am sure you aright have. But finding about about someone does take time. My SO and I go out to dinners and movies and sometimes shopping. It is good to have accepting SO's and fun time out, But I have to present male also. It all comes with the balance of who we are

[AnnieMac]

Hello Gabriella, I guess my take on it is I wouldn't be too concerned about the age play so much. I don't think there is anything perverted going on there. Many CD, for ones that I know, and ones on this forum, sometimes pick various ages of "female-ness" to embody and present as, and enjoy at a certain times. I read that this is because since when we were growing up as males, we didn't get to experience those various stages of girl-hood and only were permitted to view that from afar. So we go through those stages in our CD; little girls, teens, younger women, etc., to experience what that was like. I know in my dressing habits, I generally am fairly not fetish about it and just try to look and experience as much as I can as a normal woman would, and thats extremely fun for me, especially the make-up and hair. I don't have sex dressed, and I'm not sure I would want to, but then again I am deep in my closet. But I have to admit I have thought about trying the very frilly little girly-girl, or Lolita thing out, but more like playing "dress-up", since I was envious of girls getting to be all pretty when I was a little a boy rather than anything provocative about it. When I was young if a young boy did anything even remotely "girly" there was something drastically wrong with you. Shoot, I even got made fun of for taking piano lessons, and knowing how to ice and roller skate (before hockey, roller blading and skate boarding became popular in the US). Girls did those things, and as I recall only girls played jump rope, no boys allowed to do that.

When I read your posts, I was thinking what might cause you more trouble, is the fact that you are generally now in this non-exclusive relationship with your main SO, and what will happen when he finds out that your other male interest likes to wear women clothes when he is with you. - My two cents, and much CD love back-atcha! - Annie

[Gabriella111]

I really appreciate the responses everyone!

So true, Tracy! I think you're probably right!

Very sweet of you to say, Becky! I may invite him here after I've had some time to process. I sort of need a safe space for that, and it wouldn't feel the same if I knew he were reading it while I'm still working through it all.

Thanks, Dana. I definitely know it takes time and I should pace myself, but we have both acknowledged that we're sort of overwhelmed by the situation in a sort of amazing way. Like... we can't seem to get enough of each other, in all respects. Which is exciting and also sort of terrifying. But mostly exciting!

Hi AnnieMac. Thank you for sharing your experience with me. You may be right about the age play, but his is fetishized, so... I don't know. I'm definitely conflicted about my other guy (so that's a fair observation), but I don't think I'm concerned about what he will think about me dating a CD. He is himself a bit effeminate, to the point that he comes off as being gay to some people. And he knows I think that's cute about him. But he's almost home after a day of driving in heavy traffic. We've exchanged some messages tonight, but... I don't feel the same. My CD clearly values me and what I have to offer, and that's a feeling I've not had with previous partners, who seem always to take me for granted. I think my CD may have raised the bar higher than my other guy can reach.

[AnnieMac]

Well Gabbie, like it has often been said about CD guys, you get to have a girlfriend and boyfriend at the same time.

Might end up kind of funny if you found out your main SO, dresses also, but secretly and has told no one.

[Gabriella111]

Well Gabbie, like it has often been said about CD guys, you get to have a girlfriend and boyfriend at the same time.

Might end up kind of funny if you found out your main SO, dresses also, but secretly and has told no one.

That's what I told my CD -- that he's the best of both worlds (girlfriend + boyfriend). He's a gentleman but also super in touch with his emotions and understanding in a way women tend to be rather than men. And he's hella cute in yoga pants and cute panties. Great lover. Just... what a beautiful human.

If my other guy turned out to be a CD... I would giggle til I cried. They're the first really effeminate men I've ever dated, so that I met them within a month or so of one another... life is weird. [Go home, 2016, you're drunk.]

[AnnieMac]

hahaha- good line about 2016! See Gabriella "SISSIES RULE" You kind of just made my day with that last comment, us CDs are not always so bad!

Also I think it wont be too long before the tunic and yoga pants or leggings thing becomes more mainstream on guys, they are just too comfortable not to.