Her Side, His Side

Her Side

Preparing to attend the wedding of a friend of my SO,  I, being a hetero female, donned a pretty pink skirt, white top and pink blazer.  I longed for my SO to dress the way that he would, if he was dressing only for me.  I sought out and selected out his hot pink bra and panties and dreamed of him in a skirt and blazer that would match mine.  Unfortunately, this is not something that he is currently (and I am not sure) will ever be comfortable with. Although he does where his Satin Mini Skirt and Satin & Lace Bra around the house.  I appreciate the fact that he embraces his feminine side and is able to share that with me.  

Upon our arrival at the wedding, we visited with a friend and grabbed a quick drink prior to the Bride and Groom arriving.  I did a double take when they walked in.  Previous to this, I had only met the bride.  As they entered the room, I realized the Groom was dressed in a tank top, suspenders, and a long black pleated skirt with the most amazing shining gold shoes I’ve ever seen. I looked at my SO realizing he hadn’t seen this prior to the couple sitting down at their table.  As I listened to the fifteen minutes of speeches, there were comments on how he donned a dress better than the bridesmaids.  My mind wandered to what he may be wearing under the skirt?  I wondered; did he shop at XD like we did?  Did he have two drawers full of pretty panties and bras as my SO Does?  A closet draped with a number of satin chemises and nighties? I continued to wonder what my SO would think and how he would feel about the Groom in his skirt.  Would it help him to understand this is ok?  

After the speeches, we congratulated the Bride and Groom.  It was a wonderful to meet him and to know the bride too embraces the individuality and energy of her SO.  I hope to one day discuss our commonality with them.  That’s my perspective, but I wondered about his?

His Side

The bride had been a client of mine for 15+ years and I was happy to receive an invitation for her wedding. They became a very close friends over all those years, and I was honored to be a part of this very special day. So, as we prepared for this very special occasion, we showered, I shaved, she make-up’d, and as my SO and I always do, we choose each other’s underthings. She chose a hot pink bra and panty set for me to match her skirt and blazer, and I chose the same for her. Wearing matching lingerie makes what we do seem a little more special.

Entering the small and yet, so fitting establishment with approximately 75 guests, it clearly had a unique energy feel to it.  The Bride and Groom were very cool, forward thinking, and had an energy of love and acceptance. I noticed the bride when she came in the room, dressed in white, and the typical wedding dress that most brides dream of.  The groom, white shirt, black suspenders, and what I didn’t know until after the speeches, a long black skirt with gold shoes. What I found out after, is that he dreamt it up, and she brought it into reality. A true relationship. If it was me 10 years ago, I would have been “WTF”? this makes no sense, and how can a “guy” where an elegant skirt to a wedding?  Today, I was so impressed and honored that he could just be himself, and how his new bride could support him, in being him. I was so impressed when I came up to congratulate them, that they were just who they are.  No hiding, no playing the status quo, they were just being who themselves.  That, my friends, is so admirable.  Knowing that I did not wear a skirt, I did wear my feminine lingerie underneath. He did let me know, that it was ok to just be yourself. 

Back to Her:

As I read His Side, I couldn’t help but smile.  I know how he truly feels and am blessed to be the one he shares this with.  I do hope that one day my SO can express him/herself freely for everyone.  As we saw what the bride and groom share with each other, we realized that we do as well.  Do you?? Would love to hear your stories, can’t wait! 

Satiny Hugs,

TA and WB


Rachel, Fantastic. Sounds like progress. My guess, he goes for the garter and stocking and the genie is out of the bottle. Bra’s next? I have to say that I have this new found appreciation for skirts and tops. (but only at home). It’s good to be yourself, and then find someone who loves you, for you! Keep up the great work!

WB November 04, 2023

Hi WB. Since my last post I have bought him a couple more pairs of panties, which he’s been wearing, and most recently I got us both identical garter belts and stockings, although he’s not tried them out yet. One other thing has happened too. I made the suggestion that he should get his nipples pierced (to match mine) and he has now done just that! Interesting times indeed!
Rachel x

Rachel November 02, 2023

Hi Rachel, How’s the progress. Inquiring minds want to know! How is HE doing through this process?

WB October 23, 2023

Rachel, that is fantastic. I hope that it takes your relationship to a whole new level. If he enjoys it, and you find it sexy, why wouldn’t you do it? Next step, a matching bra, garter, and stockings. Keep us in the loop. He is so lucky to have you!!

WB October 09, 2023

Thanks WB. Things have moved forward! I bought him some satin panties and left them wrapped up with a note. That evening when he undressed he was wearing them. I asked him to leave them on and let me see. He was clearly excited and a very passionate evening ensued. We spoke afterwards and, after I told him that I thought he looked really hot in the panties, he admitted that he liked wearing them. I’m planning to get some other lingerie for him to wear as I’m convinced he gets off on this. I want to make him happy and, surprisingly, I actually find the idea of him wearing feminine lingerie to be quite a turn on!
Thanks again, Rachel

Rachel October 09, 2023

Rachel, just interested. Any progress on the journey with your husband?

WB October 07, 2023

Its risky to tell her but what a reward if she accepts! The intimacy and trust is off the chart Nothing ventured nothing gained Dress in my lovelies

Stevie October 04, 2023

Rachel, Good on you. Now as the writer of “his side” on this blog, here’s my perspective. If he was dressing up in your underwear, he was interested. I am sure that you would both have been shocked and embarrassed etc. Makes sense. But yet, here we are. If you haven’t discussed it since, you both will never know how you really feel about it. So, if I may, what about inviting him out to buy matching panties, and see how he feels about it. If he says yes, there’s your answer. Or buy him some sexy panties with a note, as previously suggested. Or, pull up this site when you are on the couch, and say’ let’s shop", what do you like? I still remember when my girlfriend accepted me as me. It was a very liberating day. A ton of stress came off me, it was so good for both of us. Now, we get to play, and enjoy, and have taken our relationship to a completely new level. I say, go for it.

WB October 01, 2023

Rachel good for you and him
Several ideas
Buy him something and leave it with a note
I d love to c u in this
Hey hon have u ever seen this website; guys in lingerie is hott

I hope u ask him in some way
Hes lucky

Stevie September 29, 2023

My girlfriend is totally supportive of my cross-dressing. We have even gone together for pedicures and no one at the salon seems to notice or care. Last night we went out and I wore an outfit she picked out for me – tight jeans and a 3/4 sleeve knit shirt/blouse with a slightly scooped neck, along with block-heel sandals. She wore a sexy mini dress with heels, and while we did get a few side glances, most people didn’t bat an eye. The restaurant staff was equally accepting. I’m a little more toward the androgenous side at work, but I still wear light make up daily, and again people don’t seem to care one way or the other, which is just how I like it.
I’m fortunate that my SO allows me to be myself and is so encouraging and supportive.

Stefi September 29, 2023

I’d like to share my ‘her side’ story, and maybe get the thoughts of some of you here. I’ve been married to my lovely and loving husband for three years. A while back I came home early from work and found him in the bedroom dressed up in some of my underwear. Of course, I was utterly taken aback by my discovery and he was overwhelmed with embarrassment. He tried to explain that he was just experimenting after reading something about it spicing up a relationship. I wasn’t wholly convinced by his explanation and am of the opinion that there’s more to it. Since then I’ve been researching the subject on the Internet, including the blogs here on xdress. Whilst I can’t say that I would actively choose to have a man who wears women’s underwear, in fact it’s not something I’d even thought about until now, but I do also find the pictures of men wearing lingerie on xdress and elsewhere quite hot. We haven’t talked about this subject any further than that one time after I’d found him wearing my underwear. I’m not sure how to raise the subject again or to let him know that I’d be open to the idea of him wearing some lingerie. I’m wondering if I should introduce him to this website and maybe suggest that he should buy a few items. Most of you here seem to be quite experienced in this subject, so your opinions or comments would be greatly welcome.

Rachel September 28, 2023

Thanks for this story. I’ve been ‘out’ as genderqueer for a few years now but only wore a skirt in public for the first time a couple weeks ago. I went to a conference at the University of Connecticut where there were going to be a lot of people I have known a long time and who I know care about me and will support me. Well, the first day I was there, dressed more androgynously, I found out there were two other genderqueer people there, assigned male at birth like me, and one of them was wearing a dress! Well, that made it really easy to put on my skirt the next day. It felt great finally to do it, and great to be myself.

A couple weeks later, I wore the same skirt to work, the first day of classes, in front of a class of more than 100 students. Brown University, where I work, is very supportive of queer people like me, and I’ve had no problems at all. Still, it was another step. While I’m very comfortable on campus, I am aware that on the walk from my car to campus, I could come in for some grief. But so far, I’ve had no problems. If I’m wearing more feminine clothes and stop at our local grocery store on the way home, I will occasionally get a double-take, but that’s about as bad as it’s gotten.

One more thing you might find amusing. I always thought I was being really stealth wearing lingerie. Well, a former student told me a while ago that they’d seen my bra more than once through the sleeves of a short-sleeve shirt I’d been wearing! So much for stealth.

Riki September 27, 2023

His Side:
Job, Thank you for responding. We have been waiting, and hopefully more people jump in on this conversation.
Glad you feel less weird, I used to feel really weird. Now I feel normal, and me. Today we went out shopping to buy a couple of blouses to match the new skirts I bought. I loved the experience, and the look on the cashier’s face. (I think she figured it out, as my GF is not a 2XL – clearly)
So, my question to you, is it crossdressing, or is it you dressing? As I write this in my skirt and new blouse and x-dress underthings, I feel so much more like me, not a crossdressing other. So happy that your wife is onboard, it’s a game changer for sure. Plus something that a few of us get to experience, we are the lucky ones. Thanks X-Dress!!
Her Side:
I’m thankful my SO is able to share this with me. Being able to truly be himself has allowed our relationship to grow in ways it never would have otherwise.
I enjoy seeing how it allows him the freedom to be more creative, expressive and joyful.


WB September 25, 2023

Very good article and happy to see your friends being so comfortable to dress! I enjoy it as well and wear panties under my clothes. No it passable in my opinion, but would like to try sometime! My SO is supportive, it is only my lack of confidence that keeps me from dressing outside. Inside, I love skirts and bras and dresses!

Scott September 25, 2023

As u can see the number of people or couples who live a lifestyle as above are far and few between. Stigma and shame and embarrassment fuel reluctance to share the proclivity. I’m glad for the ones that can share this. The intimacy is incredible once shared accepted not just tolerated. I do understand the female perspective and have no animosity towards the women who can’t accept that their man wants to wear lingerie. So I don’t expect a lot of responses to this one. I was fortunate to find a friend who accepted my proclivity! Now I trust her and our intimacy is thru the roof Dress on my lovelies Stevie

Stevie September 24, 2023

I love reading stories like this, makes me fell less weird being a crossdresser. I am happy my wife is ok with my desire to crossdress but hope to someday be comfortable with going out in public. Thank you for sharing.

Job September 24, 2023

I enjoy being dressed en-fem but in my case it always has to be maid or cleaners uniforms and I am lucky enough to have worked as a housemaid for a strict mistress many times and always performing proper house or parlour maid duties

Angela Brown September 24, 2023

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