Notifications
Clear all

Welcome to Crossdresser Heaven, a safe and welcoming place for everyone in the crossdresser community.

Join Crossdresser Heaven today to participate in the forums.

How do I encourage my SO to crossdress more, if he wants to?

31 Posts
23 Users
0 Reactions
344 Views
Posts: 13
Guest
Topic starter
(@Anonymous 36241)
Active Member
Joined: 6 years ago

Hi, I'm new to the forum. Sorry if this ends up being a double post because my internet's being weird.

My partner is a MtF crossdresser, and I am a cis woman. As we both still live with our parents (I'm 19 and he's turning 19 next month) I haven't seen him crossdressed all that much. I enjoy seeing him in pretty clothes but I'm not sure how to encourage him without making it weird. We don't talk about it very much, but he told me about it quite early on in the relationship. I discovered that I was also into it at this time and bought him some lingerie that, without too much detail, he's worn to bed in the past.

However, he only really does this if I ask him, and I feel awkward about asking. I don't want to make him uncomfortable, but sometimes I wonder if he wants to do it but is shy about asking for it. A couple of weekends ago while at his house it was just me and him, so it was a great opportunity - but it was sadly missed. What should I do if another opportunity comes up, and how do I create an opportunity?

Thanks,

River

Reply
30 Replies
Posts: 13
Guest
(@Anonymous 36241)
Active Member
Joined: 6 years ago

I am sure River he is far more nervous and anxious about bringing it up than you are. I am sure he would be excited if you told him how pretty he is and find it acceptable. I know alot of girls like myself that started dressing young and would be so happy to hear that from a cis like you.  Dont hold back becuase there is a 90 percent chance he would be delighted. Good luck girl

Reply
Posts: 13
Guest
Topic starter
(@Anonymous 36241)
Active Member
Joined: 6 years ago

Thank you for your advice. I know he's probably more nervous than me about it, logically, but it seems I'm having a hard time convincing my social anxiety that...most guys would laugh if I asked them to wear pretty clothes, even though I know my SO obviously wouldn't do that. I'll try to be the one to break the ice though because his anxiety is probably worse. Thanks again 🙂

Reply
Posts: 445
Lady
(@andreauk)
Honorable Member     CAMBRIDGE, Cambridgeshire, United Kingdom
Joined: 7 years ago

Hi River, It sounds to me he is very nervous about dressing in front of you, as he has admitted to you he is a crossdresser, he clearly has the desire to dress, and if my experience is anything to go by, that desire will not go away, if anything it will get stronger.  It is often very difficult to start to dress in  front of someone else, very often dressing is a solitary affair in earlier years and it can be difficult to open up about it and actually be dressed in front of someone else. So I think you need to try and talk to him, reassure and support him. You are doing a lovely thing, many crossdressers never get any support from those around them, he is in fact in a very lucky position. Just support him, he'll eventually thank you for it.

Andrea

Reply
Posts: 13
Guest
(@Anonymous 36241)
Active Member
Joined: 6 years ago

Hi River,  It is lovely to hear that you want to be so encouraging.

Denise and Andrea have already given great advice.   Just going from my own feelings it may be that he could be nervous about being the centre of attention, even if it is just the two of you.  Perhaps if you share the moment by also dressing up in parallel: putting on your prettiest underwear, a lovely dress and then show him some make up tips.  Make it a joint adventure to look pretty!

Have fun,

Jasmine.

Reply
Posts: 13
Guest
(@Anonymous 36241)
Active Member
Joined: 6 years ago

Hi River,  your partner is very lucky to have someone so understanding. You used the weird word: we on here don’t find it so! You are both young so will be able to explore modern styles. I was and am equally lucky. I am a straight CD who enjoys the sensations of female attire with no wish to transition but have support for those who do. Appearing as ones alternative self for a partner in early days can be nerve wracking: the male self transformed into a female form with breasts and wearing a dress, nylons and lingerie ... well, it’s a leap! Try helping him into one of your favourite elegant dresses or skirts maybe to show your support.

Reply
Posts: 13
Guest
Topic starter
(@Anonymous 36241)
Active Member
Joined: 6 years ago

Thank you everyone for your responses, it means a lot. I was thinking about buying some lingerie for myself anyway, so I really like Jasmine's suggestion and will definitely try to implement it. He's not very confident and displays signs of depression, so it makes sense that he wouldn't like being the centre of attention.

I also haven't given him any dresses yet, so that'll be a fun thing to try. I have given him pajamas, panties, lingerie and a few tops, but not dresses. He says he doesn't want to overdo wearing makeup because (in his words) he "doesn't want to look like a drag queen." However, I think he'll be happy with the eyeliner and mascara I'm getting him for his birthday. Maybe that'll be a good chance to do something?

Reply
Posts: 271
(@charchar1959)
Reputable Member     Buffalo, New York, United States of America
Joined: 6 years ago

He is very lucky to have you in his life.  It takes a special woman to accept and appreciate a man with a burning desire to express his feminine side through dressing.  If he truly trusts you, and you stay patient with him, he will come around.  As Jasmine mentioned, a shared intimate experience could be the perfect opportunity for him to break free of any reservations he has about dressing in your company.  In fact, it could move him to happy tears, which I can attest is a very important emotion for a crossdresser.  🙂

Reply
Posts: 13
Guest
(@Anonymous 36241)
Active Member
Joined: 6 years ago

I know from experience how hard it is to appear dressed in front of another for the first, indeed a lot of times. Make up is fine but ‘neck down lady’ is good too!

Reply
Posts: 2144
(@cyberian2)
Noble Member     Elliot Lake, Ontario, Canada
Joined: 8 years ago

Hi River!  You 2 are on the crux of being a very loving and happy couple. Don't push it. No doubt your man has the interest....all men do....however, he was raised to be a man and play a man's role. I am certain that this is bothering him because men don't wear female garb, so society says. Give him time to sort it out. I hesitate to tell you not to buy him female clothes as he might think you are pushing him into something he is afraid to do. As for make up....tell him more and more males are wearing make-up. Actors, media people and aging males...so much so...that there is more make-up sold to males than females now...same goes for lingerie. Let you love take it at his own pace, tell him you love him no matter what he does or wears and you support him in his decisions. He does not have to wear dresses.....slacks and tops are fine. Look at the females in your territory and see how they dress. Dresses are quite rare now. Blend in with the crowd....no-one will notice him.  Best of luck to you both. Feel free to contact me anytime with q's or you man can too, to discuss his feelings and thoughts with me. I am here for you.

Dame Veronica

Reply
Posts: 13
Guest
Topic starter
(@Anonymous 36241)
Active Member
Joined: 6 years ago

He did tell me he prefers a more simplistic style of makeup, and his goal is to look more androgynous. I’m not very sure how to create that style. Maybe I’m more tempted to wear dresses than most women because I wear Lolita? 😅 He has actually asked for some of my stuff in the past, so if he asks, would it be okay to give him stuff then? He just doesn’t wear anything in front of me unless I ask.

I had a chat with him last week about what we would like to do more in the bedroom. I mentioned about the crossdressing thing, and he told me he’d love to do it more. I guess he’s just shy about asking. Thank you everyone for your advice, I’m really grateful for it 😊

Reply
Posts: 31
Lady
(@mistified)
Eminent Member     ny
Joined: 9 years ago

River,

Many of us have struggled keeping this to ourselves whether it be weve done it for 1 day or 30 yrs. telling someone is very uncomfortable, but that is out of the way. I know from experience that when I show my wife my outfits she is somewhat laughing and disapproving. Im never 100 percent comfortable dressed in front of her. I never done it from start to finish in front of her. But it gets better each time I do it. I struggle with the thought when I dress each time but, struggle less each dressing, purchase or make up application. its a baby step process. I always wanted to do a date nite out, to break the ice. Good thing is you are approving and positive  and encourage.

M

Reply
Posts: 124
(@confused11)
Estimable Member     HARRISONVILLE, Missouri, United States of America
Joined: 6 years ago

Hi, I’m new to the forum. Sorry if this ends up being a double post because my internet’s being weird.

My partner is a MtF crossdresser, and I am a cis woman. As we both still live with our parents (I’m 19 and he’s turning 19 next month) I haven’t seen him crossdressed all that much. I enjoy seeing him in pretty clothes but I’m not sure how to encourage him without making it weird. We don’t talk about it very much, but he told me about it quite early on in the relationship. I discovered that I was also into it at this time and bought him some lingerie that, without too much detail, he’s worn to bed in the past.

However, he only really does this if I ask him, and I feel awkward about asking. I don’t want to make him uncomfortable, but sometimes I wonder if he wants to do it but is shy about asking for it. A couple of weekends ago while at his house it was just me and him, so it was a great opportunity – but it was sadly missed. What should I do if another opportunity comes up, and how do I create an opportunity?

Thanks,

River

Hi River,

I will reply from my own experience. Over time I expressed my sexual desires and crossdressing interest to my wife. She came to accept my bisexuality and allowed me to me with men. On the crossdressing finally not too long ago my wife had me try on some women's clothing. I was so excited and took it and ran with the freedom.

My point in the short story is to be honest with your boyfriend. He may think it is only a sexual fantasy or he may fear where it going. He could feel pressured from family and social norms to hold back. Therefore, I think you should tell him how you love him dressed as a woman specially if you see he enjoys wearing women's clothing. Being honest and open I would think will help him feel more comfortable. I would say to be sure to explain as a normal thing and avoid any sexual desires in this at this point. If he already wears woman clothes in front of you this should not offend him but help him feel more comfortable being a woman with you.

I tell you this because that is what I would want you to do with me if I was your boyfriend. If my wife had opened the opportunity years ago I would be much further in expressing myself now than I am. I had to be a man for so long it now upsets me I have so much to over come to be my true self.

Wish all the best to you both,

🤗😘

Jessica

Reply
Posts: 149
(@skyler1090)
Estimable Member     Chicago, Illinois, United States of America
Joined: 6 years ago

Hi River, I’ve been meaning to comment on this for a while now and just never remembered lol. For me, I was definitely pressured by a conservative family and social norms to be a guy at all times. So I hid my feminine face behind a half assed attempt at a beard, cut my hair short, etc etc etc. it got to a point a couple months where the pressure and holding it in became too much to handle and I broke down on my fiancé’s shoulder telling her everything. She said she had a feeling I felt this way for a long time but she never wanted to pressure me. Definitely don’t pressure him, but do encourage him If the situation arises. When she saw me depressed or really low in the beginning she would ask if I needed some Skyler time.  That was so comforting to me to know she understood. Now she has grown to accept Skyler as who I am and who I want to be if we’re not with my family. It’s brought us a lot closer in the process too. We’re not only best friends and future husband and wife but we’re best girlfriends too. We do our shopping together, pick things out for each other and just understand each other so much more. Last night she joked that our cycles seem to have aligned lmao

Reply
Posts: 13
Guest
(@Anonymous 36241)
Active Member
Joined: 6 years ago

Oh wow, River - I feel a bit envious of your SO.

Remebering back to when I was 19, I would have been both ecstatic at having such an encouraging SO - and yes, for me, the suggestions and requests would have had to come from her - I would have been terrified to ask or push it on her and scare her off, despite assurances.

I would have loved situations that "forced" me to dress; As an example, I had a German language lesson in which we had to narrate a set of pictures which told a story.

Mine was particularly challenging as it hit a nerve directly - a boy was larking about at a picnic by the river with his mother, and two other mothers and 5 girls. The boy fell into the river, the girls helped him out, and his mother dried him.

Oh dear! The only available dry clothing was a short pink dress and white knickers, which his mother forced him to wear. He sat there glowering as the girls laughed.

I choked back the feeling that this was my dream scenario!

Maybe that type of fantasy would work?

As a variant, maybe take him to buy a nice dress, pretending it's for you, then go for a coffee and spill a drink all over him. The replacement clothes are in the bag!

Just an idea, based on my own likings (and a true story!).

Reply
Page 1 / 3

©[current-year] Crossdresser Heaven | Privacy Terms of Use | Link to usContact Vanessa | Advertise with Crossdresser Heaven

 
[kleo_social_icons]
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!