• This topic has 30 replies, 23 voices, and was last updated 5 years ago by Anonymous.
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    • #120703
      Anonymous

      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

    • #120709
      Anonymous

      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

      • #120712
        Anonymous

        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 🙂

    • #120757

      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

      • #120914
        Anonymous

        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?

    • #120762
      Anonymous

      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.

    • #120763
      Anonymous

      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.

    • #124577

      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.  🙂

    • #125920
      Anonymous

      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!

    • #125929

      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

      • #125930
        Anonymous

        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 😊

        • #160143
          Khloe West
          Duchess

          Best to both of you, River!

          You’re awesome!

          Encouragement, acceptance and all are key elements.

          I got crazy lucky in finding the truth about”this” side of me in my early 50’s 7-8 years ago and have a 3 decade plus marriage that lasted through it and now a wife that buys me cute things!

          😀

    • #125945
      Misti
      Lady

      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

    • #128057

      [quote quote=120703]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

      [/quote]
      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

    • #128644

      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

    • #132087
      Anonymous

      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!).

    • #132142

      Hello river, If only more of us could have an SO like you! I am fortunate enough to be one of them. She’s wonderful, encouraging, honest and playful, we have blast! Its been 1 1/2 years together and yet I still sometimes get nervous about dressing maybe dressing too often, after all she met and fell for a guy. I sometimes struggle with the acceptance, is it real or they just saing it because they want us to be happy…even at the expense of their true feelings? Through conversations, re-assurance, compliments and mutual trust it gets easier. She’ll do simple things, like point out a person when we’re out saying that what they’re wearing would look good on me. Because I’m still trying things and learning there are times I’d rather do it alone. Good luck to you both, Enjoy All of it. He best appreciate your efforts.

    • #132911

      [quote quote=132142] I sometimes struggle with the acceptance, is it real or they just saing it because they want us to be happy…even at the expense of their true feelings?
      [/quote]

      Hell yes, me too

      River, you could always take the lead more on his dressing, depends on how far you want it to go i suppose. He is lucky to have you x

      Lacey

    • #133198

      Would be good to find out if you managed to bring the girl out in him a little more. Can I ask what you like in all this. Is it seeing him more feminine or do you like a more Dom role.

      There would be so many Girls on here wishing they were in his place. Hope it goes well for you both

      Lacey x

    • #134021
      Leah
      Baroness

      most of us would love to have a SO like you. I would suggest to lay out lingerie for him to wear during the day and at night.  Suggest a “girls night in”,  offer to do his nails, or his make up. sad to say, many of us CD’s are extremely sensitive in dressing up with or for our SO’s as well as sensitive to the comments.  Far too often there is too much negative social views and opinions that dressing up is not “normal” or acceptable.

       

      Keep s posted

    • #142077

      The first time my wife asked me to dress up i was nervous but after i realized how it made her feel i was more comfortable each time i did it.  Show him you care and make him feel comfortable with no judgment! And he may just open up and surprise you occasionally!

    • #144807
      skippy1965 Cynthia
      Ambassador

      Just saw your post and I agree with the advice others have given. I would take an opportunity some time when you have an evening alone and let him know that you are comfortable with him dressed ans that he doesn’t need to worry about you reacting negatively. And that he need not wait til you ask him but can dress when the mood strikes him. You might also suggest he “underdress” and that doing so might make him think of you when you’re apart.
      Cyn

    • #144943
      Anonymous

      Scrolling through the forums here…

      For me, my biggest issue dressing in front of my wife is the judgement that she would see me as less of a man, or less of a person really. Nothing wrong with being more of a woman I should say, though I am not trans, not to disparage anyone else, that’s just me, but for some reason that’s how I felt.

      Funny enough I knew she didn’t see me as anything less, but that’s what really stopped me from even opening up or talking to her about it.

      I don’t know anything about your situation, that’s just what helped me out in terms of dressing with my wife.

      • #152418
        Stephanie Flowers
        Ambassador

        Lilly , I feel much the same way. Being with her for so many years and just opening  up to my thoughts to dressing makes me very insecure about her feelings. She’s assures me that she’s perfectly fine with it,  supportive and only ask that when she needs her husband that I will be there. But reading stories and articles about significant others and their thoughts and feelings about their dressing I’ve found though statistics that for all of wives, gfs and significant others that a high percentage that show support only do it to tolerate it and really wish it wasn’t happening. I hate statistics but this particular one does bother me and for that I’m insecure embarrassed whatever they feel towards my wife can actually see me dressed I do dress but not often in front of her she doesn’t mention it nor I asked. I’m blessed to have her but it’s me and my insecurities , something I need to overcome.

        Stephanie 🌹

        • #152430
          skippy1965 Cynthia
          Ambassador

          Totally understand where you’re coming from Steph. My ex was not at all accepting or even tolerant and eventually left(several issues but the dressing was a big part-probably the MAIN part). I have not been in a relationship since then in large part due to worry about what a potential partner would think about it. I know now (unlike before I got married when I was certain the need/desire would go away once I got married) that Cyn is a big part-perhaps the main part of who I am and why I am the person I am. I honestly still don’t know where my final destination lies-whether social or medical transitioning will ever happen-or whether I’ll ever be 24/7 Cyn mode or all the time outside of work or where I am today where I dress full mode at home most times but “stealth mode” most others. I do know that Cyn is NOT gonna be locked in a closet again or even confined to the house. I did that for far too many years and it was crushing to the soul.

          I recommend doing what you’re doing now-gently exploring yourself with the loving support of your wife. Be there as her husband when she needs you; be willing to share Steph with her a bit at a time as you are both comfortable with doing so; but most importantly-always ALWAYS let her know that you are still the PERSON she fell in love with and that your love for her is infinite and never-ending (and not changed by however you appear on the surface bitbonly deepened by her love and acceptance of you for all of who you are)! I hope and pray that one day I will find someone who can love me that way, and that God will allow me to recognize them before they slip away!
          Cyn

    • #147262
      Anonymous

      Why not mention to him that you wolud like to see him do somehousework, seeing he enjoys dressing like a woman he should also enjoy being a good little housewife. In a light moment mention it to him but insist he must be enfemme while being a housewife.

      Tell him how girlie he looks and that you can tell how much he appreciates his feminine side. Suggest he be a housewife more often. Watch himblossomm.

    • #152392
      Craig Johnson
      Baroness

      My story is that I am Bisexual male in a committed relationship with a Bisexual male who is a CD. I would like to try crossdressing and my girlfriend like the idea, but has said she really prefers me as a man. So we have agreed that I will start slow. Go news is I am about her size so I can wear some of things. I guess my issues is this: My girlfriend is so stunning and I think I would like kinda silly with her.

    • #152419
      Stephanie Flowers
      Ambassador

      River, it’s not you, We’re  the ones that are insecure . Worried about how you gals really, truly feel about our dressing. Trying to express ourselves to ourselves is difficult in itself  but what you significant others feels worries us and for me likely always will. Talk ,talk and more talk , that’s the way to make things happen.

      Stephanie 🌹

    • #152435
      Anonymous

      I think I’m arriving a little late to this party.  Very curious to know if things developed with the  boyfriend?  Given the level of silence . . . I’m thinking this poster has moved on . . . sigh.

    • #162478

      It takes a while to be comfortable around others, as we usually kept this secret from everyone, let him do it on his own time, show your interest buy buying little things like a bracelet, or whatever. have him go shopping with you. He will hopefully have a blast. Both of you will. He’ll open up more often. He does trusts you. Most crossdressers keep it secret forever. Good luck. Have fun.

    • #162479
      Anonymous

      I’m so sorry guys, Captcha made this difficult for me to post before, so I have to tell you now. Me and my boyfriend broke up on Monday for non-crossdressing reasons, so I’ll be unsubscribing from this post. I’ll keep it up in case it’s beneficial for others, though.

      River

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