My dilemma, or question to you, do you have advice on how to have that conversation with a woman I’m interested in. I have not been in a serious committed relationship in sometime. I have accepted my kink, but how do I ask a woman to accept my kink? Do I mention this on date 1? How do I approach it? Do you have any advice?
Since you referred to wearing panties as a kink, let's talk about kinks.
First off, you cannot expect anyone to accept your kink. Not everyone you are in a relationship with, or intimate with, will accept your kink. They are under no obligation to. But I feel if someone has a kink, they should probably disclose this to their partner.
So, let's talk about the word "probably".
Many of us have kinks, fetishes, turn-ons, whatever, that we enjoy in the bedroom (or the living room or the garage, I am not one to judge). Some of these interests are enjoyed either alone or with someone else. A kink can be a powerful thing. Meaning that we may not always be able to, well, control it (but we are all adults and we are all responsible for our actions and decisions). For some people, they can suppress their fantasy and live their entire life without indulging it. Some people cannot be intimate unless their kink is incorporated (that sounds so formal lol) into sexy time.
If you honestly feel you can live the rest of your life without wearing panties, either in intimate moments or otherwise, then you PROBABLY don't HAVE to disclose this side of you. But I don't feel that it's realistic to suppress this side of yourself for very long.
Here's the thing. During our impressionable years, crossdressing (or anytime a boy wears girl clothes) is portrayed as comedic or embarrassing. A male cartoon character wearing a dress is supposed to be hilarious. As we grow and our entertainment matures, a man wearing panties is supposed to be kinky. Therefore, we probably assume that this side of us is ONLY a kink. And to be fair, it might be.
But I feel that many of us assume that wearing panties is only a kink. Yes, you may be aroused, but I also think that wearing panties (or whatever else we wear) makes us, well, happy. I wear panties all the time. Picking out my panties for the day is not an erotic experience (even if the panties are very sexy lol). If wearing panties makes you happy, either during intimate moments or otherwise, and you can't imagine living the rest of your life without them, then I feel you should disclose this.
I don't think any of this is a phase. This is who we are.
So ask yourself. IS this ONLY a kink? OR do panties make you happy? Think about this. Be honest with yourself. If you wear panties ONLY during intimate moments, it MIGHT be ONLY a kink. BUT if you wear panties almost every day, it MIGHT be because panties make you happy.
I do not feel that the first date is the ideal time to disclose the kind of underwear you have on. I mean, it might be, if the conversation drifts that way. You may want to... um, feel things out over the first couple of dates. If the two of you move to the physical stage of dating, it's normal to talk about what you both enjoy during sexy time. If panties are indeed ONLY a kink, this is probably the right time to discuss this.
If you do not want to stop wearing panties (whether or not wearing panties is a kink or something else) then I feel that having this conversation before any commitment is made is the right and respectful thing to do. Crossdressing is sometimes a deal breaking for some people. And that's okay. People are allowed to decide who they want to be in a relationship with, and there can be a lot of factors in that decision.
But consider this for yourself as well. Do you want to be with someone who will not tolerate your crossdressing? Do you want to be with someone who would be angry if they found out you had panties hidden from them? If this is a kink, do you honestly feel you could live the rest of your life not indulging in your kink? If this is more than a kink, and panties make you happy, do you realistically think you can spend every day and every night for the rest of your life only wearing boring boy underwear?
Love, Hannah
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I agree with everything Hannah has said whole heartedly. Although the looming question for every guy in this position is: How do I go about it? When I was younger it was even more frowned upon than it is now, but I am a masculine guy, I have never been concerned with lingerie making me look weak and more than anything I have always loved wearing it (I actually think it make me look more muscular). The way I let more than just a few women know about my love (it has never been a kink in my eyes) is by waiting till the first opportune moment when she was in her bra and panties to tell her how much I love matching bras and panties, then I reveal how much I truly love real lingerie – and vintage lingerie. I made sure I made her aware of it multiple times in the future, this is also a great time to compliment how beautiful she looks in whatever she is wearing. I also used intimate time to tell her how beautiful I believed she would look in stockings and garters. I also made sure to buy her a set of matching bra and panties as a gift. Back then thongs were just becoming popular but my love has always been French cut panties. After a short period (different with every woman) when I was comfortable with the relationship, I would buy us a pair of matching panties for the bedroom. I never had a. woman who was revolted by it, it was always worth the small investment. More than one reciprocated by purchasing another matching pair and wanting us both to wear them somewhere special. The odd part was 3 women I dated wanted us to wear them to dinner at their parent’s house. . . I have more questions about that one though LOL.
To anyone reading this, don’t be in a hurry. Lots of conversation and praise for her beauty is important to her praising yours. Compliments, acceptance, and unconditional pleasure all goes both ways.
Live, Love, laugh and look good doing it with the one you love.