Dear Diary: Can You Do My Makeup?

After almost a full year of admitting to myself and my wife that I enjoy crossdressing and want to continue exploring this side of me, she still has not seen me crossdressed. We have been taking it all very slowly in order to not overwhelm anyone or cause any issues. There does come a point, though, where I feel we got stuck in the period where she knows that I crossdress when she isn’t home, but we never share any of it together.

She had been cautious about bringing up the topic, and I was the same way out of fear that she would feel awkward about the topic I brought up. I am a people pleaser, so I don’t want to make anyone upset or awkward.

This all suddenly changed last month. We went out to dinner, had a few drinks and once we got home, the topic of crossdressing came up and that is just the beginning of it!

The Big Moment: “Go Put Something On”

We got home from dinner, we both had a few drinks and my wife gets much more courageous when she drinks a little. The topic of pegging came up and she wanted to buy a strap-on. I told her that I would be interested in it and also potentially while crossdressed. I told her though that I felt like that was taking a big step because she hadn’t even seen me crossdressed yet. She responded to that by telling me “Go put something on.”

I was kind of shocked by how direct she was about it. She hadn’t even seen a picture of me dressed as Catie, but now I was about to walk out in front of her in a dress and a wig for the first time. I didn’t push back at all so I just grabbed my stuff and went into the other room to put something on for her to see.

I put on a thong, covered up by a little black dress that she gave me a while ago. I put on my red wig and thought about putting on heels but decided against it.

I was ready to walk in. I didn’t know what to expect. I thought this could possibly be the most awkward moment of my life. I took a deep breath and walked in.

The Reaction: A Tease and a Compliment

As I walked into the room, I felt her eyes on me. I stood in the doorway dressed as Catie. She looked me up and down before saying “You have a deodorant stain on that dress.” To many people, that would not be the reaction they were looking for. They would want to hear “OMG, you look so good!” or “I love that dress on you!” For me though, it felt right. My wife and I joke around with each other all the time so it felt familiar to me in a not so familiar situation.

She made me do a full turn so she could see all the angles. While turning, she said, “Your butt is looking a little flat,” to which I told her that she needed to give me some workout plan to build my butt. Just typical relationship conversations, right?

I put on the heels just to show her that I could walk in them. She doubted that I could. I showed her that I knew what I was doing and she gave me my first compliment saying that my calves looked really nice when wearing the heels.

And just like that I got undressed and got back into bed with her before asking the next question, “Can you do my makeup?” I posed it like I wanted to see if I even look good wearing makeup, and to my surprise she went right into the bathroom to grab her makeup bag.

Makeup Time: The Moment She Took Control

She had me sit down on a chair in the bathroom, and she took out a bunch of different things. Eyeliner, eyeshadow, lipstick, blush. She asked me what I wanted to try and I wasn’t sure, but I told her that I could never get eyeliner to work on my eyes so I’d like to see if she could get that to work for me.

I have hooded eyes and the eyeliner always smudges and looks bad on me. She tried her best to get it to work on me but to no avail. We then moved on to just finding out what would work best. She did a pinkish eyeshadow with some mascara, then she did some blush on my cheeks before putting on some lipstick. She told me to look in the mirror and ask if I liked how it turned out.

In all honesty, it wasn’t the greatest, because it was more about it looking more bold than the natural looks that I typically enjoy. She then told me that I should put something on that matched the makeup to see the full look.

The Full Look: Dressing Up and Feeling Like Me

I went and put on my flowery full length dress that made me feel like spring. I put on the wig as well and she told me that it looked like I was going to church. Again, another teasing moment that made me feel comfortable while in makeup and a dress in front of my wife.

I ended up taking a few pictures of myself, documenting the moment. I felt very happy about it all and honestly was just very relieved that it all went well. I got undressed after my little photo session and took a shower, took off all of my makeup and my wife called into the bathroom and told me to make sure that I cleaned my butt well because she had something for me when I got back into the room. So, I obviously did as I was told.

The Aftermath: New Boundaries, New Adventures

When I got back into the room after my shower, my wife was in the bed and on the nightstand was her dildo and some lube. I didn’t even have a chance to put any clothes back on before she told me that I should bend over the bed so that she could use her dildo on me. I was not as nervous as I thought I would be. I have used a dildo on myself before, but never having someone else use one on me. It was definitely a difference in control level for me.

I did as I was told, I bent over the bend as she came up behind me. She caressed my ass as she lubed up the dildo; I told her to take it easy on me and be gentle. She was gentle as she slid the dildo into me; I took some deep breaths as she slid it in and out. It felt very good with her in control of the pace of it. I had gotten aroused as well which I think she enjoyed seeing.

She then told me to get on my back and put my legs in the air. This position was an intense feeling as she held the dildo near her pelvis and thrust into me as if she were wearing it as a strap on. She looked very happy to be in control, but I couldn’t stay in this position for long. So I asked her to switch over to me on all fours with her behind me.

In this position, I was able to reach down and stroke myself as she continued to thrust the dildo in and out of my ass. It felt amazing as this was happening and it didn’t take long for me to reach orgasm and it was such a strong one.

I got cleaned up and then made my way in between her legs and pleasured her orally before both of us fell asleep, happy and content.

The Morning After: Reflecting on Our New Normal

The next morning we woke up and I wanted to make sure that we talked about what all went down so that I could make sure that with no alcohol in her system, how she felt about what we did. I was not surprised, but she said that she enjoyed it and that she would want to do it again. She also said that we should buy a real strap-on that she could use on me. We picked out one that had a vibration setting and a small dildo for her as well.

I also asked her about planning a shopping trip together so that she could help me pick out some outfits that she thought might look good on me since a lot of her comments were about the outfits being too “conservative” or “not matching.” So we will have that to look forward to!

With all that being said, the strap-on arrived this week with a pair of crotchless panties that I plan to wear when she uses the strap-on. Stay tuned for my next “Dear Diary” post that updates you all on my journey!