I planned a special out of town weekend for my SO last weekend for Mother’s Day. It was supposed to be all about her and her special weekend, and it was. In her own words it was an incredible weekend for her, and it ended up being for me too.
A little background, my SO is not my wife or gf, she is my ex-gf and baby mama. I see other people and she sees other people. We broke up two years ago and were in a bitter custody battle for over a year. Since we settled our case we have worked on our relationship in the best interests of our small child. I consider her an SO because we are still intimate when we do get together.
I told her about my cd’ing years ago and she has seen me dressed. She was disgusted. That’s not however what caused us to break up. She came along as I went to visit family the weekend before and indicated she wanted to get intimate when we got back to my house. As soon as we got there she went in to my bathroom and pulled out all the makeup out of what she considers her drawer, only there was a lot of makeup that wasn’t hers (she has a sixth sense for when something is mine and when it's another girls). She looked stunning with the liquid eyeliner she put on of mine that night which had been in the back of my mind all week. As I picked her up for the Mother’s Day trip she was wearing the same eyeliner. It’s all I could think about the entire 3 hour drive. I told her how great she looked and we both played blissfully ignorant whose makeup it was.
The moment came later on that evening. We spent the day at the pool and the evening walking around before going back to the hotel. There was so much I wanted to do around my old college town, but she wanted to relax. It was her weekend so she was going to have it her way. She thought we were having a disagreement about what to do for dinner, using the art of feminine persuasion and rubbing against me being sweet. All I could think about was how great she looked with my eyeliner on. After about half an hour of holding back I told her again how great she looked. She said thank you and sensing my anxiety asked what I was thinking about. I looked at her with a blank stare, then I stroked her face and told her I wanted her to do that to me. Considering how we left this subject two years ago I felt as vulnerable as the smallest person in the world.
I had no idea what to expect next. She smiled sincerely and said okay. That was comforting, but that was also her initial reaction the first time I told her about my desire to dress up. Doubling down on my vulnerability was that she told everyone as we were going through our custody.
I don’t remember exactly how we left things that night, but I knew it went better than the last time. The next thing I remember we are headed out shopping the next morning. There was a thrift store with a huge Mother’s Day sale. I had a good idea she was going to pick out some garments for me, but it was Mother’s Day and in no way was I going to ask and steal her spotlight.
I’ve bought my own makeup and nail polish at the grocery store – where I can self checkout without anyone really knowing. The thrift store was loaded with people for the 50% of sale. As she started picking through the racks, she held up garments asking me what I thought. I wasn’t sure how to respond, so she nodded and said out loud, “for you.” She was shopping for both of us, but with every outfit she pulled out it felt like she was only shopping for me and everyone knew it. This is a pattern that would play out through the weekend. We would go to a store with new people and she would hold out items and ask me what I thought as if I were her best girlfriend. After initially being shy and embarrassed at each place I got slightly more bold digging through the racks, though I tried to at least look as disinterested as possible. I got comfortable enough at one place that I tried on a pair of shoes as quickly as possible that I thought I had to have.
I certainly did not intend to push this thing this weekend, but based on her actions I knew I was going to get a dress up session that night. However that didn’t come with one last inquiry and hesitation. She brought it up at dinner, then retracted and said we’ll talk about it when we get to the hotel. On the ride home she said she just needed to know if I was gay or wanted to be with a man. I explained again it is simply a fetish and I find the soft fabric, makeup, and looking pretty to be intoxicating. We aren’t together as a couple, and I told her if I wanted to be with a man I would be with a man. I reminded her that for me it was a way of letting go and surrendering control to someone you can trust. She said okay, that was all she needed to hear.
I was still hesitant back at the hotel and felt she was having second thoughts. I asked if there was anything else she wanted to talk about. She said no, and then I responded. She laughed and said encouragingly, “No, go ahead. Get dressed.” She helped with makeup and gave advice, some of which I didn't know about. She explained the importance of moisturizer and foundation, and the order in which each item of makeup goes on. After I started dressing she looked at each outfit up and down, telling me which ones looked cute. She took my camera and photographed the outfits she liked and having me pose. She told me how great my legs looked and when I looked at her pics she had taken several from just the waist down, and some of the shoes I picked out. She put some silicone inserts in the shopping cart to fill out the bras she picked out. As she was taking pictures I was adjusting the inserts and she told me to stop playing with “my” boobs.
The next morning I woke up still in a pink fog next to her. Everything was still cool and the world hadn’t stopped. She giggled so many times throughout the weekend. As we got in the truck I asked her how to get the cups flattened out in your bra when they get out of place and folded. She laughed and told me how hard it is to be a woman. She said exciting things on the way home like “we can have a slumber party and paint each others nails” and “you’re like my girlfriend.” I played in to that role by looking online for the most girly, pink panties with lace and satin, and asking her for her opinion.
We also talked about normal things on the ride home, like music and friends. That is important because I don’t want her to think any less or different about me when we aren’t doing what she is calling “my thing.” I think she realizes that she has a thing too, and this is just my thing. We aren’t together and it might be really hard to believe, but neither of us wants to get back together. But we still get intimate more often than not when together and I don’t want her thinking of me any less a man. With all we went through the past year she said she now understands where some of my anger came from (I’m not an angry person) and she trusts me now more than ever. We both love our child enormously. I’ve been through enough with her, and read so many stories on this board, that I know that things can change in an instant so it’s hard to carry any expectations going forward.
