Oh by the way, did I mention, “surprise?!?”

Good day all! I hope today finds everyone in good spirits and good health. I’m sitting at work, and I feel I’ve processed the events of last evening to put my thoughts to text. You see, it started like any other Friday evening…

There I was, at a local hot wing restaurant, meeting Miss Girlfriend and her co-worker Molly for snacks and drinks. You see, Molly has had a rough time of things lately, so Miss Girlfriend and I have taken extra efforts to be there for Molly, and help her get through things. She’s an exceptionally good friend to Miss Girlfriend, and now to me as well. So when Miss Girlfriend messaged and asked if I could meet them for drinks, I was more than happy to. I’ve grown protective of Molly, and I’m able to offer specific advice she needs in her situation.

So I arrived early as I’m prone to doing, and when they arrived, the fun began. The three of us have a great sense of humor, and when we get together, we have a really great group dynamic. So we tend to have great conversations and fun. We just look forward to hanging out with her, and it is always great to have a friend like that.

So recently, Miss Girlfriend and I had gone out with Molly, a friend of hers, and a Douche that is unfortunately in Molly’s life. (Douche is putting it nicely.) Despite the Douche, we all had a really great time, and I even learned a few things about Molly that made me all that much more comfortable around her and with her. Learning these details had also been an impetuous in why I felt comfortable in telling her about me as Caden. While we had been out that night, Molly had indicated she wanted to take a girls weekend in Vegas. Having never been to Vegas and wanting to go, I mentioned to Miss Girlfriend that I’d dress as Caden if it meant I could go to Vegas. We laughed about it, and moved on not thinking much more about it.

So before I go much further, I think you should know that on occasion, when the opportunity arises, I will throw a joke around about crossdressing or dressing up. I think I do it subconsciously, but there are the occasional times where I throw it out there, sort of fishing for what response I will get. When I do it, I’ll exchange a knowing glance with Miss Girlfriend. Usually I get,

“Oh you are so funny!” and the conversation moves on.

Well, last night, Molly brought up the Vegas trip idea again, and when a lull popped up, I excused myself. When I returned, I said,

“To go to Vegas, I’d dress as a chick.” Molly merely smiled, and responded,

“I know.” At that same moment, Miss Girlfriend looked at me and said,

“She knows, I told her.” Being very astute and a brilliant statesperson, I gave her a puzzled German shepherd look and said,

“Knows what?!” Like I said, a brilliant statesperson.

Miss Girlfriend then went on to explain she had talked to Molly about it back around Christmas. Well before I started blogging and well before I had written my short list of friends I was contemplating possibly telling about Caden. Molly seemed very at ease and comfortable about it, and was all smiles. Eventually the conversation moved to other topics.

I decided I’d like to show Molly a photo of me dressed up, so I pulled out my phone, cued up the photo, and put my phone down. Miss Girlfriend is very perceptive. She knew what I wanted to do; so she asked me,

but the conversation wasn’t where it needed to be for me to do that. So I waited for a lull in the conversation. Miss girlfriend picked up on my intention yet again, and asked me what was on my phone. She was simply trying to give me an intro into the conversation. So I decided to give Molly an out; I asked her if she’d like to see a photo of me dressed up, because once she saw it, she couldn’t very well un-see it. She said she’d like to see it. So I showed her one of my favorite pictures.

Her initial response was,

“Oh my God, this is you?!” The smile never left her face, and it was a sincere smile. I felt I was in good hands.

Her next response was,

“I’d do you!” Like I said, we’ve got twisted senses of humor, and I seem to have a knack for getting rare praise. So I took it! We joked for a little bit, and the conversation went in other directions. I didn’t exactly want to dominate the conversation, or push the conversation, so I was oaky with that. I had what I needed, acceptance and understanding; compliments weren’t bad either.

Eventually we hard to part ways; so we said our goodbyes, we hugged Molly, and she headed home, while Miss Girlfriend and I finally had a moment to talk before we drove to my place. She seemed anxious that I would be upset or angry about her confiding in Molly and not telling me. I can only hope I made it clear I was not angry or upset, and that I was still very oaky with her knowing. I had merely felt slightly foolish at not knowing, but that passed as soon as I realized that my world and Miss Girlfriends world had grown just a little bit more. Miss Girlfriend explained she had not wanted to tell me out of fear that I’d start to get comfortable and want to start telling everyone. I’ve never wanted to tell everyone; I’ve always known that wasn’t feasible or practical. This was the primary reason why the list I wrote was so short and specific. Because not everyone in our lives are worthy of knowing about Caden; I’m cognizant not everyone would be able to handle the information well. So I can only hope Miss Girlfriend can see that I always plan to exercise a great deal of discernment and good judgment. I Love her, and I’d do nothing to jeopardize what we have, who we are, or where we are going. Nor would I jeopardize her or my children by letting people know or find out which may cause them to catch some gender grief over who I am.

Ever & Always,

Caden Lane


7 thoughts on “Oh by the way, did I mention, “surprise?!?”

  1. Pingback: Forgotten Dental visit and Cruise vacation woes | A Southern Crossdresser

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