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Tried Crossdressing with SO

29 Posts
26 Users
132 Reactions
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Posts: 11
Lady
Topic starter
(@canadianeagle97)
Trusted Member     North Carolina, United States of America
Joined: 10 months ago

So I came out to my wife a couple months ago. She’s had her ups and downs on how she feels about it but recently has been very okay about me crossdressing. I very nervously asked her one night how she’d feel about getting me some clothes to wear and she said definitely, and actually offered for me to try on any of her clothes at some point. 
You can imagine my excitement, but I still just can’t shake the feeling of shame of my wife seeing me like this. I hate feeling this way but I hate keeping secrets from her more, and she’s even expressed she doesn’t want me to keep this hidden from her. 
Tonight I asked to try some things on and she even helped me pick out the first thing. I felt extremely supported by her doing this for me. I started putting it on and totally froze up. 

“do you not want me to watch you put it on?” She asked. 

I slipped into the bathroom to get into this soft black dress she had picked out for me. I still felt mortified once it was on to walk back into our bedroom and let her see me. But I eventually did. She could tell I was very nervous. She asked me how it felt and offered for me to try on something else from her closet. 

I still can’t help but feel shame, guilt, and really maybe embarrassment. I’m not sure what to do. Has anyone else felt this way? Does it ever go away? I’m terrified to push too much on my wife but at the same time just trying on a dress is scratching the surface of what I really want to do in terms of crossdressing. 

- Bella

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28 Replies
15 Replies
 Lacy
Duchess
(@rholtman96)
Joined: 2 years ago

Reputable Member     Lincoln city, Oregon, United States of America
Posts: 198

@canadianeagle97 I remember the first time I dressed for my wife, I was terrified and it took me at least six months to be able to dress in front of her. I still feel slightly embarrassed to dress in front of her. It gets better easier as time goes b y. Good Luck and enjoy your time together.

Lacy

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Duchess
(@alison-anderson)
Joined: 6 years ago

Noble Member     Middlesex county, New Jersey, United States of America
Posts: 1742

@canadianeagle97 I'd say everybody felt this way the first few times they told someone, the first few times they were seen by someone, the first few times they went out in public, and probably more occasions.

This comes from years of conditioning telling you it is wrong. It takes a long time until we fully accept ourselves, that this is a part of our life. The fact that she is supportive of you, that she is willing to see you, and to let you try on some of her clothes is a sign of her acceptance of you. When you learn to accept yourselves, these feelings will go away.

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Managing Ambassador
(@lizk)
Joined: 5 years ago

Illustrious Member     North County San Diego, California, United States of America
Posts: 3847

@canadianeagle97 

It goes away Bella.  It gets better too.  Learning to accept ourselves takes time.  You have to work at it.  A therapist might help.  The important things to remember are your wife loves and accepts you, and keep communicating with her.

/LK

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 Lea
Lady
(@lea-jhene)
Joined: 9 years ago

Noble Member     California, United States of America
Posts: 1098

@canadianeagle97 I have felt something similar, but for a different reason because I was trying to dress for my wife and start the conversation before she knew I was a CD.

I dressed a few times for my wife to show her this hidden part of me. Each time, I would get dressed, then it would take me minutes, even a half hour, to work up the courage to walk out, step by step, and show her. I was always nervous, and even changed back to guy clothes on numerous occasions instead of letting her see me. It was exhilarating, scary, nerve racking, and empowering all at once.

I should have talked to her in advance though.

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Ambassador
(@jacquelinelarkspur)
Joined: 1 year ago

Famed Member     Gateshead, Tyne and Wear, United Kingdom
Posts: 1497

@canadianeagle97 

All the feelings you describe are perfectly understandable. Your wife has handed you a golden opportunity here. She's clearly curious to explore your crossdressing with you, and has been active in her support by picking out things from her own wardrobe. That alone speaks volumes. She also obviously wants you to feel comfortable dressing in front of her, and that question she asked about whether you wanted her to watch you put on her dress shows a lot of kindness and consideration. 

I think there are many here who wish they were in the same situation, myself included.

You're wise to not push the just-opened envelope too far too quickly. As others have said, take things one step at a time. I think that you and your wife would benefit more from a conversation about limits and boundaries, then base your practical experimentation on what you both agree on. Your wife will let you know what's too much for her. If she is as supportive as the signs suggest, then yes, your shame and embarrassment will subside. 

Good luck to you both.

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Ambassador
(@lucyb112)
Joined: 2 years ago

Noble Member     Staffordshire, United Kingdom
Posts: 1005

@jacquelinelarkspur @canadianeagle97 

I was going to add my reply to this topic, but to be honest, and not for the first time, Jacqueline has written pretty much word for word my thoughts on the subject.

You do indeed seem to have a very considerate and understanding wife 

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Duchess
(@michellemybell)
Joined: 3 years ago

Noble Member     Clearwater, Florida, United States of America
Posts: 614

@canadianeagle97 Dressing in front of my wife is difficult for me since I know she really hates it and even when she is trying to be supportive it is hard on her so bottom line is I don't do it except occasionally a nightgown in bed or a cute apron when making dinner.  Even if it didn't bother her so much I know I am afraid it would change her opinion of me as her man and all the guilt and shame that goes with that.  

Your wife sounds amazing and someone you can communicate with to find a good balance for both of you.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 3998

@canadianeagle97 There is good advice from experience here, Bella.

Since everything is out in the open, good communication will be key. And since both of you need time to get used to your dressing, maybe you can schedule regular times to be together when you can practice and experiment with your styles. Weekdays, weekends, after work, after the kids are asleep. Whatever works for both of you.

A lot of CDs would wish to be in your situation, that's for sure.

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Lady
(@hobby)
Joined: 7 years ago

Estimable Member     Northwest wi, Wisconsin, United States of America
Posts: 83

@canadianeagle97 Good day!  Absolutely!  While I don't feel shame, I get very nervous and concerned about her feelings.  Many years ago my wife said she liked a man that could show his feminine side.  I will never forget that statement.  Like i said that was probably oh, 16 years ago.  Mikki has not dressed in front of her since.  I know, it's probably my own fear of whether or not she still accepts it.  She did have concerns that I might want to do it fulltime.  I guaranteed to her that "this is a hobby for me".  That was my go ahead!  While that hobby is different than crafts or antique cars, its a hobby.  I really do like being her man and always will.  BUT I also love being a woman.  Mikki

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Baroness
(@river)
Joined: 1 year ago

Noble Member     New Hampshire, United States of America
Posts: 827

@hobby So familiar !! Cheers RC

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Duchess
(@loneleycd)
Joined: 5 years ago

Famed Member     Roland, Iowa, United States of America
Posts: 2150

@canadianeagle97 

So happy for you, Bella. Having a SO that is accepting is great. I do suggest caution. Keep your lines of communication open. For us when we see our wives accepting our feminine side we tend to get excited and wanting to push ourselves. It is so easy to go to far to fast. With each step be sure she is OK with it. Maybe let her know that if you are going beyond her comfort zone to tell you. 

Best of luck to the both of you. 

Cassie 

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Baroness
(@annaredhead)
Joined: 11 months ago

Famed Member     Cornwall, United Kingdom
Posts: 1806

@canadianeagle97 I generally dress in front of my wife, she has commented on my makeup process. She's been along to makeup lessons and photoshoots with me. I don't feel ashamed as my wife is very supportive and we go clothes shopping together. We avoid buying matching items though we've had to flip a coin a couple of times or debate who spotted what first.

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(@christineth)
Joined: 2 years ago

Noble Member     Brussels, Brabant, Belgium
Posts: 747

@canadianeagle97 Bella, I remember the first time I dressed in front of my wife.  I was nervous as a long tailed cat in a room full of rocking chairs, but it was exciting.  I was worried what she would say, if she would mock me or run out/leave me.  But she was supportive if a bit tentative at first.  With time, she got easier about my dressing and I felt more and more comfortable around her, even asking her to help straighten my bra straps, zip up my dresses and so on.  It is now just a normal part of our living together.  I only dress at home…more or less or the time, but when we go out I am always underdressed and it is reassuring that my wife first checks is my bra is visible, or my panties show above my trouser waist when I bend over and so on. 

So I am sure that your nerves will ease up over time and the enjoyment of dressing and being your true self in front of your most precious loved one will become a feeling of deep seated contentment.

I know I am a nicer person when dressed, and my wife often comments on that.  Plus I do much more house work than previously, so that is another benefit that my wife expresses appreciation of.

I am pleased for you that your wife is so supportive.  It is only natural to be nervous at the beginning…but the honesty is rewarding in the end.

Hugs

Christine

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Lady
(@cdgabrielle)
Joined: 2 years ago

Estimable Member     Wesson, Mississippi, United States of America
Posts: 102

@canadianeagle97 it takes getting dressed in front of someone a few times before you get over the nerves of wondering what they are thinking. I was definitely ashamed and self conscious dressing infront of my wife. But over the years we both have developed a comfort level with my dressing. It's still exciting to be seen but not as scary as it used to be.

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Baroness
(@river)
Joined: 1 year ago

Noble Member     New Hampshire, United States of America
Posts: 827

@canadianeagle97 You nailed it !!!.  Alone im fine its all good .. when it comes to my wife Im terrified,  and embarrassed. I  Need to stop all the guilt and shame and just come out and say Honey do you want to play dressup with me? Maybe i should get a few cocktails in her first lol..  Cheers RC

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Posts: 114
(@shelly-lynn)
Estimable Member     Grand Rapids, Michigan, United States of America
Joined: 7 years ago

It certainly takes time to get passed the shame, guilt, and embarrassment. Society dictates how we are programmed and it is a hard cycle to break. Over the years I have accepted who I am and dressing with my wife is much more normal for both of us. Life is so much better when you can break away from the way from how we were raised and be your true self.

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Posts: 2100
Hostess
(@cdsue)
Famed Member     Delaware, United States of America
Joined: 5 years ago

I would agree with what everyone has said.

After I came out to my wife we went online and ordered a couple bras and dresses for me. When they arrived she had me try them on to make sure they fit. I asked if she was okay with it and she said she was and that if I was going to dress I may as well look pretty. I dressed in front of her and she was positive in her comments. There were other times she gave me some of her clothes that either she didn't wear anymore or didn't fit her. She helped me buy make up and showed me how to use it, we go for mani-pedi's every couple months and she told me it was okay to get color on my toes, helped me buy my wigs and helps style them, took me to a shoe store to buy heels once and the list goes on. The most important part is communication. I usually let her bring up the subject but there are times I will ask her something and she is okay with it. At her suggestion I started therapy shortly after coming out to her and that has been very helpful. 

Your wife sounds wonderful, be thankful that she is accepting and willing to help.

XOXO

Suzanne

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Posts: 935
Guest
(@Anonymous 47410)
Prominent Member
Joined: 6 years ago

Bella,

First off, you are blessed to have a supportive spouse. 

As long as the two of you keep communicating and go at it easy, things will improve for you and the both of you. 

I had been cross dressing since around five years of age, yet when I met the girl I was going to marry at 29 I told her about my cross dressing when I knew things were getting serious.  It was at that point I too experienced some guilt feelings.  Even though she was accepting and supportive, it was difficult for me to shake the guilt feelings for quite some time. With her support and time though, we both did eventually overcome my guilt feelings and move on. 

She was the one who first suggested we go out together as two girls.  I had done this earlier in life with GFs but not with my wife.  We both found this experience to be very helpful, especially in relieving the guilt feelings. 

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Posts: 712
Lady
(@jincrocker)
Prominent Member     Oregon, United States of America
Joined: 5 years ago

Keep dressing in front of her, you will soon be accustomed to her help. Ask her for help with makeup, hair styles, and such as an ice breaker.

blush when she tells you how pretty you are.

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Posts: 2172
 J J
Lady
(@jjandme)
Famed Member     California, United States of America
Joined: 5 years ago

Yes, we all feel a range of emotions unique to each of us. I got over the guilt of dressing along time ago, but I still feel a lttle embrassed dressing in front of my wife. My wife is stunningly beautiful, IMHO, so I can never look anywhere near as good as her. I know lingerie and dresses just do not fit me the way they do a GG, so I can never look as good as I would like. I have mostly accepted this and she sees me dressed often, but I know I look like a guy in a dress. Still, that said I do enjoy it so much and she is very suppprotive. I have jokingly blame her for my dressing since she is so supportive and we have a great time in bed...dressed or not.

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Posts: 1301
(@rebeccabaxter)
    Cornwall, United Kingdom
Joined: 1 year ago

Bella, as you will have seen from [almost] all the replies above, it is a common theme to feel a little ashamed or embarrassed or [fill in your emotion here...]. Trust me, it wears off and soon you will just say something along the lines of ' just going to dress tonight, my dear' and go and get on with it. Perhaps it will be like my wife and she says 'are you not dressing tonight?', that's always a validation, even now.

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1 Reply
Baroness
(@river)
Joined: 1 year ago

Noble Member     New Hampshire, United States of America
Posts: 827

@rebeccabaxter If we ever get to a place where my wife says something like. honey I can tell your stressed why dont we go get River. or I miss River where has she been lately.  OMG  cloud 9 🙂 Cheers RC..

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Posts: 812
 Leah
Baroness
(@leah63)
Noble Member     Minneapolis, Minnesota, United States of America
Joined: 7 years ago

The best way you work through all those things is by doing it ( dressing up) and pushing your comfort zone of dressing while respecting her boundaries.  It all comes down to YOU accepting this part of yourself.  With the support for your wife, thins will make it go faster and easier.

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Posts: 9
 Nina
Lady
(@fairytalescorpio)
Active Member     Ohio, United States of America
Joined: 5 years ago

I'm very blessed with an extremely supportive wife.   We always clothes shop together.  She buys all my clothes, shoes, lingerie,  makeup,  hair etc..  Sometimes we're out shopping at the clearance rack, and other times we shop online.

 

We're not out about what we're up to when in public. I fake like I'm surfing on my phone while I follow her around with a shopping basket and try to look uninterested in her shopping. She knows my sizes and will give me a quick look to ask if I like something or not. We're pretty good at non-verbal communication.

 

In spite of all her support, I'm still self conscious about it.  She does help me get dressed.  She hooks the clasps on my bras and zips my dresses.  She does my makeup for me.  It's exciting but for some reason I'm still very embarrassed about it.  She often says I look great (not at all passable) and encourages me to look in the mirror.  I can't.  I'm not at all impressed by what I see in the mirror.  I think it's societal conditioning and internal shame.  I've been seeing a sex therapist about dealing with that guilt and shame.

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1 Reply
Hostess
(@cdsue)
Joined: 5 years ago

Famed Member     Delaware, United States of America
Posts: 2100

@fairytalescorpio when my wife and I go shopping she will ask me if Suzanne would like something and to anyone who may hear her it doesn't matter as she could be talking about a sister, daughter or friend. I actually peruse the racks looking at clothes which could be interpreted as me helping her look for something, which most of the time it is. I think most people don't care so enjoy yourself when you go.

XOXO
Suzanne 

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Posts: 1784
Baroness Annual
(@d44)
Famed Member     New York, United States of America
Joined: 5 years ago

It's perfectly normal to feel so nervous when first showing Bella to your wife. But you are in a relationship with a woman who is accepting you for who you are so try to relax and let her see the real you. Just go slow and keep communicating often and you should be fine. You are extremely lucky to have such a woman as a partner.

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Posts: 85
Lady
(@amyoxley)
Trusted Member     West Midlands, United Kingdom
Joined: 3 years ago

Bella

I have been married to the most amazing woman for 10 years. I told her about my crossdressing as soon as we met as I wanted to be open with her. To this day she is the only person who knows about Amy.

She has been totally supportive from the start.

But even after all that, I do still feel slightly embarrassed when I'm dressed in front of her, and I'm not even sure why. She tells me how beautiful I look when dressed, but deep down, I know I look like a man in a dress, even after spending time on my make up. 

I sometimes find myself trying to judge her mood before dressing, which I know is stupid, but I can't help it.

Anyway, I know I'm very lucky to have her by my side.

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Posts: 503
Lady
(@kerrismith)
Prominent Member     Belvidere, Illinois, United States of America
Joined: 2 years ago

Bella,

I never crossdressd in front of my wife.  She only found out about me because she was snooping on my iPad one day and saw a photo of me dressed.  Now that we are divorced, I sometimes think about showing up at her door in a skirt and heels. I have no idea what her reaction would be.

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