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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WB Thank so much for the support! Asking her what she would like will not yield a response of “I d like to see u in a bra” so i m working on talking to her in a fully open honest discussion that says hey I m a crossdresser as u know, are u ok with this ? And if not, are u ok with me dressing at all ? Wear something pretty today I am Stevie


Stevie, Just in response. Instead of asking her what she can handle, maybe ask what she would like, and see if it raises her curiosity. Asking what she can handle is like what limits she is willing to provide you, asking what she would or might like is giving you permission to be yourself. My 2 cents.


Scott – the polka dot outfit is on my list of items to purchase for him but it is currently out of stock in his size – it’s a great idea 😀! Watch for my next blog – I may reveal a name in there😉! When the time is right I’m sure we will go out with him/her fully dressed … it’s in the works 👗👙! I have to say that his previous experiences have not all been overly accepting. I love this community – it’s amazing to have a group of people who understand and are without judgement. Thank you all for this! Lots of Satiny Hugs! TA


Great topic and excellent comments appropriate for our community. I love dressing up when on the weekends and on days off when I am lounging around the house. I am slowly working up the nerve to go out. I tend to wear a lot of black and white along with some pink and lavender. My boyfriend is very accepting and has started dressing also. When we get married—in about 18 months—we are planning two ceremonies. One in male attire and a second private one in wedding dresses. By the way, I Joanne is my femme name. Would love to hear more comments!


well wb thanks for asking. not ready to surprise her. i feel that would not be fair . as for discussing i’m working on it. i have asked her what can u handle but got no response. thank u for engaging stevie


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