Pillow Talk w/ Hannah: First Dates & Kinks – Do They Mix?

Pillow Talk w/ Hannah: First Dates & Kinks – Do They Mix?

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



The views and opinions expressed are those of the authors and do not necessarily reflect the official policy or position of XDress

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6 comments

Hanna, thank you so much for addressing this topic. It caused much angst for me in my dating years. The clear information on whether one’s underwear choice is a kink, will hopefully, be helpful to others. For me, although I often enjoyed wearing women’s underwear in a fairly masculine environment, it was not something I had shared in prior relationships. After the end of a relationship where she and I had done a little gender and role play, I became somewhat more comfortable accepting this part of myself. My new girlfriend and I went on several dates before I was confident that our blossoming relationship was more than just a fling. It became obvious to me that we were becoming more than friends. I definitely wanted to share my preference for feminine underwear vs masculine underwear before we got too intimate. Much to my surprise, she was not only accepting but, also very supportive. We are now married and continue to have a lot of fun picking out not only underwear but also other feminine clothing for each other, dressing up, and supporting each other with feedback and positive input. Whether wearing underwear day to day for all activities or wearing especially pretty stuff around the house or in the bedroom, I am very lucky to be partnered with someone so wonderful! I am so grateful for her and taking that early step to be open, honest, and vulnerable with her before we moved forward in our relationship. Please keep up your writing, it resonates with many! Thank you XDress for creating a space for this community!

Jamie

Very good blog HAnnah. I started as a kink but grew into an everyday experience. The kink started many years ago when I was young. I thought it was “weird” that I liked panties but could not stray from trying them on whenever the moment presented itself. I was on a business trip once and my SO put a pair of her panties in my suitcase. When I got to my hotel and found them, I called her and said I found them. She asked if I would put them on and send her a pic, which I did. I am not sure she knew about my kink then but it opened the door to me wearing almost daily after she “accepted” the panties on me. It was always awkward before then but now it is great! I openly wear panties and we have a few matching sets in bras and panties. Very liberating and our relationship only grew from there. I agree that sharing your kink is important and this site offers a few blogs on how to address the situation. Hope your SO’s are as open as mine was. BTW, the pair she threw in were satin and white with frilly lace on the openings. And a pretty bow on the front in pink. Very feminine! Very sexy and I have to say, the bow on all XDress items makes them fantastic!

Scott

Great article, great point is wearing ‘panties’ a kink or just wearing that something that looks great vs. just basic mens underwear…….To me wearing panties is pretty low on the kink totem pole………when to tell a new partner is a great question, to me there is no real answer that fits every relationship, other than sooner is better than later, and to be embarrassed by it, you are how you are, if someone isn’t willing to accept/like it at that point it is time to revaluate the relationship…….there are so many ways to expose this side you to another, from surprise the first time getting naked with someone to finding a way to ‘jokingly’ finding a way to ‘try’ on her panties…..hiding this side of yourself is only going to end in heartache for everyone….

Mr David

That was a really great response ! I really feel that everything you said makes sense and will help many people in making the right. choices, for me I am married with a wife who fully understands and indulges with my feminine side, and I am not a feminine looking guy, but I wear panties and body suits nearly every day and sleep in a night dress every night, I have drawers full of panties, bras, stocking etc and after wearing just put them in the laundry, my wife is very happy to do my laundry fold my clothes and underwear and lingerie if I haven’t already done them lol, but seriously I am not sure if its a Kink, more of a way of life that I love and because my wife accepts that it makes us stronger. I am so glad that I can now freely wear nice underwear and clothes that if I want to make love in stockings, panties and a bra or wear a dress etc that I can I feel comfortable stronger and happier with the situation but also maintain a very healthy active male life , Xdress is amazing and I am glad to see other company’s joining the train in providing nice underwear and lingerie for men, I hope that we continue to open minds about clothing and lifestyle choices and not allow politicians to set us back in the progress we have made, and on a final note it seems to me that some of the toughest times in history men were allowed to wear nice clothing without concern for example the Romans etc Thank you Hannah and Xdress for all you do to make life happier, healthier and a better place to be

smewie

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.

Rob

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