After 9 years of dressing in private, posting pictures, and making YouTube videos, I FINALLY went out as a woman. And not just "out", I went on a date with a man! OMG!!! I had been dreaming of such an experience forever. And it finally happened. I knew the experience would be different than my imagination--I'm wise enough to know that daydreams almost never match up with reality. And it was different than I expected. I'm sharing this experience for those who dream of taking crossdressing to another level, by going on a date with a man.
I met Jim online four months ago. He reached out to me after reading my profile on another CD site (is it okay to mention the competition here? lol). I am always interested in talking to male admirers, and we really hit it off! Our interests (and fantasies!) are closely related. Jim asked me out and even made this funny video:
https://youtu.be/bpk0b_GdFk8
We had to plan it months in advance, due to travel and other life issues. And the day finally came. Jim drove in from out of town and got a hotel room. We agreed (or he told me lol) that I should dress in the safety of the room instead of somewhere else. (I can't really dress at home because I'm keeping my CD-ing separate from my otherwise conservative suburban life.) I told Jim that under no circumstances should he see me in DRAB, guy-mode. He agreed to keep his eyes shut when he opened the door, allow me to enter, and then he'd leave me in private to dress. A little risky, given that I'd never seen Jim before, but he earned my trust over the course of our online conversations.
I pretended to leave home at 8AM to go to work and instead drove to the hotel. I live in an uptight, stuck-up neighborhood and I imagine that this type of illicit rendevous is quite common LOL. So I didn't get too paranoid about my car being spotted in the hotel lot. Anyway, I arrived at 8:20 and felt sick. I didn't want to do it. It was raining and stormy and I thought, crap. This is too much. I brought an anti-anxiety-attack med just in case, but I decided that anxiety wasn't the problem. It was fear mixed with some dread. I decided not to take the med. I chilled in the car until 8:30AM and then called Jim.
The phone rang several times without answer. I felt a wave of relief. He was bailing on me! I wouldn't have to go on the date. But, then, he answered. Oh. Okay. I guess I'm going to do this.
I felt a pit in my gut as I walked through the hotel and up to Jim's room. But I was committed and wouldn't give up. This date has been a life dream. I'm doing it. I knock on the door and Jim opens it wearing a paper bag over his head. I try to laugh but didn't have it in me. We exchange pleasantries, I'm using my girl voice while in DRAB, and he leaves me alone to dress. I tell him I need an hour to get ready. I'm still not feeling all that good.
I place my suitcase on the bag and pull out my girly things. Then, suddenly, I remember. I remember the feelings I get when I dress, how exciting and wonderful it is to be a woman. I see my dress, bra, heels, etc., and it all starts to make sense again. I start to get dressed.
Stressful!!!! Despite meticulous pre-planning, many things go wrong. My shoes (purchased online) are a size too big (I didn't realize it until then), my hair/wig is a mess and required a lot of brushing, and it was HOT! Too damn HOT! I turned down the air to the lowest setting but I was still sweating like a...well, not like a woman. This sucks!!!
After an hour, I still wasn't quite ready, but I thought, screw it. Forget about a dramatic first meeting with Jim. I'm just going to call him and meet me in the room, and I'll finish getting ready while he's here. I set up my video camera (I filmed as much as I could, videos are coming!!). He arrived.
I wasn't nervous--I was too distracted from minor failures of wig, makeup, heels, etc., until I started opening the door. OMG I'm dressed as a woman, and he's going to see me!! I peek around the door, close it slightly, take a breath, then open the door. Jim is smiles and calm and we greet each other. I'm more at ease. A little disappointed that this moment was not Disney perfect, but no complaints.
He gives me a rose. I always thought I'd be floored with excitement at such a gesture, but I was so overwhelmed with everything that I couldn't register much emotion. Did I mention I was REALLY HOT!! Sweating!!! Sweating in dress sucks!! I'm stressed and awkward but Jim is very patient. I do my nails (POORLY!!) while he watches. Then we decide to leave, finally!
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The date was all planned out. We were going to Sephora and I would get a makeover--another life dream. But first, leave the hotel and walk to the car. In a dress. Next to a man. But, yes, I needed to walk through the hotel dressed as a woman, in public. OMG!!! That's when I discover that my shoes are WAY TOO BIG. Walking is a nightmare!!! We have to go very slow. So I couldn't really enjoy the feeling of being a woman with a man because I was so focused on walking normally. I held on tight to Jim, without thinking. I'm sure he liked that.
As we walk through the lobby I keep my eyes down and otherwise don't look at anyone. Is that a giveaway? Lack of confidence? Hmmm...I wonder. We make it to his car without any issues. He opens the door like a gentleman--again, another experience I thought I would LOVE but I'm just too overhwhelmed to feel the moment. We drive to the mall.
We parked by the food court, which I didn't think much about, until we walked to the entrance. PEOPLE IN THERE!!! I see a few youngish guys hanging around and think, I DO NOT want any interactions with them. And my shoes don't freakin fit. I can't go in. NO WAY!! But I'm with Jim and I go in anyway.
Walking through the mall was awful, horrible, the worst. My shoes fall off with every step. I'm cursing over and over under my breath. I hate this. I can't walk. I'm immensely paranoid. I don't pass as a woman. I say the F-word many times. Jim is very calm, relaxed. He is my rock in this situation. I hold his hand without thinking or caring. After a few minutes of this hell, we find Sephora. Like a beackon of light, my safe place. We walk in.
The clerks know EXACTLY who I am when I walk in. I'm the crossdresser appointment for 11:00AM. I was a little (no, a lot!!!) disappointed that it was SO OBVIOUS to them. Oh well. They sit me down toward the back (by my request) and we begin the makeover.
The makeover was....nice. I'm frankly just too rattled from the previous two hours of stress and hell getting ready and walking in crappy shoes to relax and enjoy. Plus, the makeup artist was VERY slow. She was very knowledgeable and sweet, no complaints about her professionalism (I still highly recommend Sephora for crossdressers), but she was SO SLOW! For several minutes my mind goes back into guy mode. NOT RECOMMENDED. I ponder the fact that I'm a guy in a dress in the mall, sweating profusely, with crappy shoes. I am NOT AT ALL EXCITED, despite the fact that I'm fulfilling a MASSIVE LIFE FANTASY.
The makeup artist explains tons of stuff to me--which I pretend to listen to but will never retain. Lots of information. Huh. Every time I reach to touch something, I see my crappy nails. It looks like a child did them. Horribly bad. I realize that it is better to NOT do your nails, then to do them poorly.
She finishes the makeover. A switch flips. I see myself and smile. I smile bright! I look wonderful! The sales associates see me smile and they smile, too. I'm happy.
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I'm beaming. Jim slipped out to buy some shoe pad things, and they help a little. We take a few videos of me in the store (videos forthcoming!), and finally decide to leave. I'm a little better at walking, plus I have the confidence of a makeover, and the return journey through the mall isn't so bad.
But it's raining. Jim leaves me at the door to retrieve the car. WHAT? You're leaving me alone? I stand outside the doors, shielded from the rain, but in plain site. Alone. Dressed as a woman. I hide around the corner, make another quick video, and then, as I walk to the front, I see three young men hanging out in the smoking area. CRAP!!!! I'm dressed as a woman!!!! I DO NOT FEEL SAFE!!!! I duck around the corner to hide. People are walking in and out of the mall. I'm dressed as a woman. I'm alone. Jim, where the hell are you?
He's taking a while. I have a paranoid image that he has abandoned me. I brought my ID and credit card, so I could always get a cab or something. But it would also mean a heck of a lot of time alone, in a dress with terrible shoes, in this god-forsaken mall, while I figure things out.
Jim pulls up. Thank you! He the gets out of the car (in the rain) to open the door. The young men look at me and laugh. Have I been 'outed'? Or are they laughing at Jim for opening the door for a lady? I'll never know. I do know that in my elegant dress, I'm noticable. GG or not. I stand out.
At this point I'm totally exhausted. Jim wants to go out to lunch, but I decline. I can't take much more. I want to go back. We have a quiet ride back to the hotel. Jim is uncomfortable with the silence, but to me, right now, quiet time is golden. My metabolism settles down. It is nice. I'm getting comfortable FINALLY!!!
We hang out in front of the hotel. There are a few people around, but they are the type of professional, cell-phone-obsessed people who obviously are not paying attention to others. I am comfortable here. I ask Jim to take some pictures of me. They come out AWESOME!
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I'm starting to enjoy myself. I had a few minutes alone while Jim parked the car. When he comes back I'm much more 'myself'. I start to feel the joy of the experience. While feeling the moment, thanking him for everything, I give him a quick kiss. I wanted to get that overwith!!! The big first kiss is done and over. The world did not end when I did that. Another life first for Dana.
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I really enjoyed those moments in front of the hotel. Instead of ending the date then, as I was tempted to, I tell Jim I want a drink. The hotel bar is empty, so we enter. I'm still paranoid as hell about being outed, but whatever. I want a martini, and Jim tells the waiter "she" would like one. It is the first time I have heard myself referred to as "she". It feels wonderful. We chat. I make another video. I relax with the martini.
Incidentally, I had very few fluids all day. Totally on purpose. Given all my crossdressing fantasies, using the ladies room is NOT one of them. I was succesful in not having to "go" during the entire experience.
As we sit together in the quiet hotel bar, Jim talks to me about his business, and my mind wanders occasionally. I look down at my outfit. I smile. I remember to sit up straight, like a lady. Again my mind wanders. Are my legs positioned appropriately? I smile more. My hands are in my lap. I'm sitting like a woman. I love it. I had a makeover. My makeup is wonderful. I'm a woman in a hotel bar, dressed elegantly, sitting with a man in a suit. This is really, nice.
Jim walks me back to the room. I'm still stressed about being in public, but I'm getting used to it. Jim is a perfect gentleman the entire time. After some intimate talk (just talk!!!!! He really is that sweet) he leaves me alone to return to regular life. The cleanup process is much easier, and I shower and change back to DRAB.
I leave the room, acutely aware of the differences, now that I'm in DRAB, of walking around in public. I get in my car, I start to drive away. Jim is walking in the parking lot. He sees a brief, tiny glimpse of me in guy-mode. I wave quickly and drive off. I'm not freaked out in the least. The date has ended. I'm exhausted and exhilerated. Jim wants to go out again, and so do I, but we have no idea when it will happen.
I get home and make myself a drink. And think about this amazing, stressful, wonderful, eventful day. Going on a date as a woman, with a man, was a life dream. I just achieved it.