Exploring DRESSing UP!

Exploring DRESSing UP!

When I first started getting close with and learning about my SO, he was very upfront with me about liking lingerie. When we began dating, I made a purchase for him from XD and was pleasantly surprised at seeing him in it. The blue satin panties had enough room to fit everything perfectly and as a woman, I found they had a naughty sex appeal and his confidence and comfort in them, soared.

As a fan of RuPaul, men wearing women’s clothing was not a stretch for me and I actually found many of the gurls to be incredibly sexy, confident and beautiful.  I asked my SO if he would ever consider dressing up for me, either at home or for out on the town.  At first, he thought it might be fun to try once, so we went shopping and found a pretty, thigh length shift dress with a tiny black and white circle design on it.  That evening he allowed me to put makeup on him, he chose bold red under garments and put on his new dress.  His salt and pepper hair matched the color of the dress he wore, which added to the sex appeal.  Being the amazing chef he is, he spent the evening prepping the most delicious lamb chop meal paired with the perfect wine.  The rest of the evening was spent with wine, music and wonderful conversation followed by the admiration of a beautiful pink satin nighty he wore.

To my chagrin, that dress was returned the following week, and though my enjoyment of the evening was brought up on occasion, my SO pulled back from the idea of dressing up like this for me again.  I would bring it up on a bimonthly basis and was always met with a little bit of pushback.  I eventually took this to mean he was not interested in trying this again.  Months passed and I put the idea out of my mind, respecting his choice and enjoying the satin and lace undies he wore daily.

As October rolled around, we started discussing Halloween and possible costumes or outfits we could wear as a couple.  The idea of going out to supper dressed as ‘girlfriends’ came up.  This was the first time in a long while the subject had resurfaced, and I was interested to know if he was entertaining the idea for me or for himself.   Through discussion, I discovered it was for me and I truly did not want that – I wanted it to be for both of us if it were to happen.  Halloween came and went, and we decided to just enjoy an evening of conversation and connection.

The following week, we began texting (we live a couple of hours apart) and he asked me what I thought of the lavender French Maids outfit on the XD site.  Knowing he has a black and white one, I suggested he wear it for his house cleaning that morning.  He put on his hot pink cheeky satin and lace bra and panties from XD and his black and white French Maids outfit, along with some lipstick.  As I received some photos of how pretty he looked, I asked him what I would call him if he were female.  His response was not immediate, though it didn’t take long for him to tell me what it would be.  After our discussion, he spent the morning having coffee and cleaning the house with this pretty look.  He told me he has never felt so free!  

We had a long discussion about how difficult it has been for him to share these two special pieces of himself – wanting to wear women’s overwear and coming up with a female name.  I feel privileged and blessed to be the one he shared this with.  Though it has only been a few weeks since this occurred, it has definitely helped our relationship to grow stronger.  I’m looking forward to enjoying this together!

Is there something more you could be sharing with your significant other?  Feeling free is an amazing blessing you should afford for yourself!

Lots of Satiny Hugs!


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I love this site, such beautiful dainties. I’m a closet fairie sissie, and I love dressing. But I could never pass. I just love the feeling of being a sissie. My biggest disappointment as I look at all of this beautiful lingerie is that there is nothing here in my size! Alas! I would have to have an XXXL. I’m not beautiful on the outside, but I love feeling beautiful on the inside when I get an opportunity to wear some lovely, satiny, girlie-girl attire. Aaaaahhhhh me!


I have a very accepting SO who is aware that I dress. However he has never seen me dressed when we are together and we are not meeting atm due to Tier Restrictions. I would love to totally dress for him one day but not sure of his reaction although he does not judge me for dressing. I have dropped hints about dressing whilst with him and he hasn’t said no but he hasn’t said yes either


Stevie, What would happen if you either dressed up in a dress, heels, and make-up snd surprised her, or just gently opened up the conversation, you may be surprised at her response. Does it feel better to keep it a secret, or open up and have the freedom to be yourself?


This new exploration and opening up has been such a blessing for his freedom of self and for our relationship. We’re loving every moment while ensuring each other is ok each step of the way ❤️!


Yes there is! I love dressing up! I do it to relax to feel sexy and for arousal! While she knows i wear panties and have bras she doesn’t know i d love to wear a dress and heels and some light make up! She knows i do my toes! We’ve even had pedis together But its still an uphill climb Glad TA your re progressing. It brings u closer Wear something pretty today i am Stevie


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