So I’ve been browsing the forum for about a year now but this is my first time posting so apologies if this is too wordy… but I’m a male and have been in a relationship with my girlfriend for coming up to 2 years. We’ve done quite a lot sexually in that time which she’s mostly taken a lead with which is great because I love trying new things but am always too scared to mention it or ask to try it.
The most I’ve done is bought a strap on for valentines day. She was shocked but seemed happy. We’ve not gotten round to using it yet but I’m positive we will soon.
Essentially I’m more than happy to explore different kinks and sexual experiences with her. However there is one kink I have that she has no idea about, and that is Cross Dressing, specifically in lingerie.
I’ve spent hours reading posts on how people have told their partners about this kink but I just can’t bring myself to do it. I know she loves me and would accept it but I think she would see me differently. I mean how could she not?
I’m 5’11, work as a mechanic, have a big bushy beard, enjoy working out and have a muscular bulky build and am just what would typically be classed as a stereotypical man I suppose. I like being that type of man if I’m being honest, but how can that sort of man still be who he is if he wants to put on a satin corset, thong and lace suspenders?
Perhaps I’m overthinking it, but I just dont see a way that I can possibly explain this to her without it changing how she sees me
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Definitely overthinking it, it sounds that she would be ok if you told her. Just explain to her why you like it have a proper conversation about it.
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You are definitely overthinking the situation.
Why should she see you differently? You are who you are and what you are wearing doesn’t affect that.
I’m 73, heavily built, bearded and build and ride motorbikes. I started wearing women’s lingerie around a year ago and my wife didn’t at an eyelid.
She helps me buy the lingerie and buys it for me as birthday and other presents.
Just pick the time and talk to her about it.
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The only thing you will regret is waiting to have the conversation……
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Firstly, you are such a sweetheart, bless you, this is so close to my heart and thank you so much for sharing.
When we first started seeing eachother, I knew my husband was into cross dressing. We used to go to themed events as an excuse to dress in drag together (whether we were good at it or not!) and he used to obsess heavily about making sure he was clean shaven everywhere etc. The dramas of a curious drag queen/king were occasionally explosive!
He’s a gardener and handyman with a big bushy beard (I sometimes call him Captain Silver). He’s quite masculine externally but very effeminate inside, and I confess initially I didn’t like playing in the bedroom when he dressed up, but we satisfied each other’s needs and it made us both happy (especially the pegging, we both loved that so much when we had the energy for it, it’s so empowering for her and satisfies all the urge for him. Now you have the gear and she didn’t react negatively to the idea, I’d totally recommend you have the conversation about trying it (if both comfortable of course)).
He doesn’t feel the need to dress up as much these days as it takes so much prep for him, but honestly if you can have an open conversation about the sort of things you might like to try with your partner I’m sure she’ll understand, and might even delight in a bit of soft/hard domme play, or even just some gentle tactile stuff if you’re game for that 
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@KinkFreak I know its getting harder to talk about the longer I wait but its easier said then done I suppose
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@rockstar How did you approach the situation if you dont mind me asking?
@Wolf_in_White thank you for sharing your experience with me, it definitely gives me hope. For me its purely a sexual thing so drag doesn’t really appeal to me in the same way I suppose. Would definitely like to try pegging as being submissive seems quite fun but again, similar to discussing wearing lingerie, I feel nervous asking for it if that makes sense…
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That does seem to be the only way to go about it, its just a difficult thing to talk about as like I said I worry ehat she might think
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Firstly, hello fellow mechanic!
Secondly, it sounds like you’ve built a really loving and trustworthy relationship, I understand that trying something new in a relationship like yours can be a little nerve wracking. You’ve built up this self image of yourself that fits traditional masculinity and that’s great, just because you enjoy wearing lingerie doesn’t undo any of this!
You can still be the bearded, muscular mechanic who loves working out and enjoy wearing lingerie. One doesn’t cancel out the other. It’s just another layer of who you are!
You said you’re sure she loves you and would accept it, which already tells me you know deep down that this won’t be a dealbreaker- which is a great step.
When you do decide to tell her, you don’t have to drop it all at once. You could start by bringing up the idea of lingerie in a general sense. maybe something like, “I’ve been curious about what it might feel like to wear something like that, just to see what it’s like.” And see what her reaction is from that?
At the end of the day you deserve to be able to be comfortable whilst exploring your kinks, there’s absolutely nothing wrong with that. Be honest with your partner, see how things go from there. Good luck with everything (:
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@WaveyAlien I’ve considered way to casually bring it up, but it just feels a bit intentional. Like she would definitely ask me if thats something I’m in to, which is sort of what I want, but again it’s just nerve-wracking. Thank you for your postive reinforcement and encouragement though
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@user408 No problem! There’s absolutely nothing wrong with admitting it’s a kink you’re into, it can be nerve wracking at first but it’s good to be upfront if you can. Maybe try and make sure you’re completely at terms with your kink before bringing it up, I’m into a few “questionable” things myself and I know how it can feel bringing it up to a partner. Once you’re fully comfortable it might seem a bit less daunting
Once again, it sounds like you and your partner have amazing communication amongst one another. The fact that she was keen on the strap on gives me hope as well. I’m so certain everything will work out for you, it’s just a little nerve wracking actually bringing it up (:
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@WaveyAlien I don’t think theres anything wrong with any kink to be fair including cross dressing, but when its your biggest secret that nobody has ever known it just feels a bit wrong I suppose. Especially when I would consider myself traditionally masculine in my relationship with my gf.
I overthink and worry how her knowing this could change the dynamic of things outside the bedroom…
When you say “completely at terms with your kink” what do you mean by this?
You’ve said that you’re overthinking a bit and find it nerve wracking, which is completely understandable- kinks and fetishes are a very personal thing and sharing that with someone can be frightening! What I mean is that by accepting that your kink is just another part of who you are, it doesn’t necessarily mean that dynamics have to be changed. You can still be stereotypically masculine and enjoy cross dressing. I know it can be scary opening up about an otherwise secret part of ourselves, especially when you’re worrying about other details such as how it might impact dynamic and whatnot, by focusing less on those details it might be easier to bring it up to your partner (:
I know it’s all a lot easier said than done, but as others in the thread have also said the sooner you find yourself able to have a conversation with your partner about it the less it will be able to play on your mind
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Discussing a kink is always going to feel daunting. LH does have some products that might help with exploration, like the Date Night Dice and I’m sure they have a card game or something too, it could be an idea to buy one of those and have a giggle with it. Even if nothing comes of it sexually it could be a great ice breaker for you to ask her about the kinds of things she might be interested in trying in the bedroom and in turn sharing yours, maybe over a glass of wine while you’re both nice and relaxed x
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@WaveyAlien thank you for the advice, I’ll have a think about it all. You never know, I might find the courage to bring it up this weekend
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@user408 Hello and welcome. A nice introduction.
It’s definitely worth bringing up cross dressing with your GF. Otherwise you’ll always be hiding in the shadows. It’s of course not an easy thing to bring up. A few possible options that come to mind are:
Bringing it up in a conversation exactly as you have in the thread above explaining that it’s one of kinks.
Or perhaps a more subtle approach to suggesting you either both swap clothes for fun or if sizes don’t match suggest you both try some cross dressing some evening and then build up from there. By explaining her how much you liked it and would like to build on from there.
Good luck and enjoy. 
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Completely understandable, it can be a difficult subject, it messed up a relationship of mine but I’m going back to the early 90s we were young and attitudes were different, then after that relationship broke down and I started a new relationship, I took time to bring it up and really tell that partner what I like about it, it wasn’t a 10 minute conversation, I didn’t just blurt it out, I took control and decided when and where I was going to talk about.
My advice don’t talk about at the weekend,plan it know what you are going to say be ready for any questions she might have. At the end it’s a kink she might need time to take it on board, if she thinks of you in a different way then maybe that relationship isn’t right for you, but I’m sure by the sound of it everything will be fine.
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@Wolf_in_White thats a good idea, I’ll look into something like that
@teacake thanks for the advice, I won’t actually bring it up this weekend but it would be great if I could and just deal with it. Sorry to hear about your first experience, that is one of the other worries I have. But hopefully it will be fine if I actaully do bring it up one day
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