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Thread: My First Date as a Woman, with a Man (Long Post!)

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    Dana Matthews danam's Avatar
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    My First Date as a Woman, with a Man (Long Post!)

    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!

    CD01.jpg

    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.

    CD03.jpg

    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!

    CD04.jpg

    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.

    CD05.jpg

    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.
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    Been around for a while, been away for a while. On the verge of coming back...Help me!

  2. #2
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    Glad it wentfairly well! Is a second date with Jim in theoffing?
    "Normal is just an illusion, what is normal for the spider is chaos for the fly" - Morticia Addams

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    New Member marie123's Avatar
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    Aww...you look so happy! Glad it went well.

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    Amazing! I don't think I could handle so many major hurdles in one outing!

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    Hi Dana, How could anyone mistake you for anything other than a very lovely young lady.

    Your video is incredible .
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

    If at first you don't succeed, Then Skydiving isn't for you.

    Be careful what you wish for, Once you ring a bell , you just can't Un-Ring it !! !!

  6. #6
    Rachel Rachelakld's Avatar
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    You look stunning (okay we have the same smile lines, and I thought I was looking in a mirror).
    The outfit and glasses is really top shelf stuff, heck wish I could date you as well except we would be mistaken for sisters.

    So now we are all wondering, any plans to take this Jim thing to a more intimate level? He does seem very nice chap.

    OMG, just saw the video, he's so cute, I like him, hope you two hit it off.
    Last edited by Rachelakld; 09-19-2015 at 09:00 PM.
    See all my photos, read many stories of my outings and my early days at
    http://rachelsauckland.blogspot.co.nz

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    That is an awesome story and you look so pretty too.
    Jim sounds like an absolute peach!

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    Junior Member laurenp245's Avatar
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    Aww.. That's so sweet! What an amazing time you had, evident by that ear to ear grin in that one picture... you look so happy! Smiles like that only come out when a person truly feels in harmony with themselves. You look fantastic, I absolutely adore your dress! You two most definitely make an adorable couple and I wish you two nothing but the best!

    <3 Lauren
    Last edited by laurenp245; 09-19-2015 at 09:28 PM.

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    The Girl Next Door windycissy's Avatar
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    You go girl, Jim sounds like a prince and you look like a princess! Next time you two can just relax a bit and enjoy each other...be safe and enjoy every moment

  10. #10
    Dana Matthews danam's Avatar
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    Did I mention I was freakin' hot! In the temperature way lol. I will NEVER wear another outfit that shows sweat Best to go out in the winter so I can go outside and chill! Oh, and I will absolutely make sure I have shoes that fit properly. So many things that you learn when you go out for real. What an experience!!!!
    Been around for a while, been away for a while. On the verge of coming back...Help me!

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    I am me! TrishaTX's Avatar
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    you look great and had fun....and Jim seems like a nice guy. Good for you....
    No regrets except I should have got dressed & stepped out sooner.

  12. #12
    Silver Member prene's Avatar
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    Sounds like you both had a good time.
    great

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    Aspiring Member LaurenS's Avatar
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    Quote Originally Posted by KrisB View Post
    Amazing! I don't think I could handle so many major hurdles in one outing!
    Me either! Way to go, Dana!

  14. #14
    Dana Matthews danam's Avatar
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    Here is a picture I meant to upload, but I hit the maximum number of pictures in my first post. It is me, after the date, FINALLY relaxing. It is one of my favorite moments of the experience. I'm still processing everything in my head!

    CD06.jpg
    Been around for a while, been away for a while. On the verge of coming back...Help me!

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    you look great love your dress Jim sound like a nice guy

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    Martini Girl Katey888's Avatar
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    So Jim is the perfect gentleman he appeared to be on the video...? I'm so pleased for you both...

    You've done awesomely well going in at the deep end Dana, you look great and your contentment is clear in that smile..

    Hats off to Jim too, Sounds like he handled any hiccups with complete aplomb - not an easy thing to do on any first date, but especially...

    Pleased for you Dana - just make sure you test drive any new shoes next time around...

    Katey x
    "Put some lipstick on - Perfume your neck and slip your high heels on
    Rinse and curl your hair - Loosen your hips, and get a dress to wear"
    Stefani Germanotta

  17. #17
    Gone to live my life
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    Hi Dana,

    Congrats on a great night out. I remember watching the vid when you first posted it and thought Jim seemed like a great guy. I am glad you both had a good time . . . rain aside.

    Cheers

    Isha

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    Gold Member bridget thronton's Avatar
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    You look very good and thanks for sharing

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    I glad your date went well. You're very attractive. Let us know how things progress with your friend. Yes, on the shoes, it is best to give them a workout before wearing for an extended time. You may want to stuff some tissue paper into the toes of the shoes. I've found adding some tissue may push the foot more toward the heel of the shoe.

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    Aspiring Member Sarah Beth's Avatar
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    You are so lucky and I am so glad you had a good time. He sounds like a dream come true for you and I hope there is a next time for you and you are more comfortable then so you can have an even better time.
    "It takes all kinds of kinds" Miranda Lambert
    Now some point a finger and let ignorance linger
    If they'd look in the mirror they'd find.
    That ever since the beginning to keep the world spinning
    It takes all kinds of kinds.

  21. #21
    Aspiring Member Sarah-RT's Avatar
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    Dana this reminds me so much of the first time I went out, while I wasn't on a date some of the other experiences are the same. The fear and panic thinking everyone is staring or what they might be saying, the worry your clothes don't look right, your make up is done poorly or 100's of other things, but once the calmness arrives and you can relax it is a truly wonderful feeling existing outdoors.
    I cant stand to fly, I'm not that naive. I'm just out to find the better part of me. I'm more than a bird, I'm more than a plane, I'm more than some pretty face beside a train. Its not easy to be me.

  22. #22
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    d:

    Glad you had a nice time! I suspect it can only get better. However, I do have one word for you:

    Jewelry.

    The necklace is nice, but that shouldn't be the only piece. Perhaps a bracelet and watch or a ring. Anyway, a bit more glitz is needed.

    My issue with shoes is a bit different. One foot is slightly shorter and wider than the other. I adjust with heel pads as needed, but tissue doesn't work for me. As it gets moist from sweat, it just becomes a lump. I use the Moleskin that is offered in the foot care areas of drug and grocery stores. It is soft padding and has adhesive on one side. I cut it to fit and place it under the vamp. It prevents the foot from moving forward. Depending upon how thick the Moleskin is and how much you need to take up, you may need more than one layer. It comes in only 1 color: tan. Sometimes it shows so I need to use a Sharpie to paint the edges dark.

    By the way, you didn't say what Jim does, but he does seem to have that Walter Chronkite trustworthy vibe...

    DeeAnn

  23. #23
    Cereal Killer Ashley in Virginia's Avatar
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    I sweat when I get nervous as well... When I dress, I crank the air conditioner down to the mid 60's... Then after a few minutes, I'm freezing... Lol

    Yesterday I bought a pair of sandals from Nordstrom rack, and I could feel my internal temp skyrocketing... Once I got back in the car I started to come down.

  24. #24
    Aspiring Member irene9999's Avatar
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    With the wig and shapers it can get very hot going out en femme! Looks like you had a great time though

  25. #25
    Neanderthal in nylons Julie Denier's Avatar
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    Oh lord, don't I know it about the sweating! Even when you have the AC going full blast in a hotel room, it rarely cools the bathroom, where you spend most of your time applying makeup under hot lights ...

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