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Okay girls, here it goes…
A quick background on me: I came out as a gay male during high school (early 2000s) and have come to truly love the CD community for its accepting and supportive environment.
For the past 3 months, I have been in a relationship with another man who I finally discussed my dressing habits with. After a very long discussion, to my surprise he asked to take me out on a date as my female self “Rochelle”.
Of course I said yes and we set the date for the following Friday night.
Throughout the next week, I was terrified and at several moments considered backing out. I have been a crossdresser for years now, but never have I gone as far as going on a date dressed as a woman while with a man!
Eventually after receiving much support from fellow crossdressers, I carefully picked out my outfit, gathered up the courage, and decided to just “try it out”.
Friday finally arrived and I couldn’t feel more scared. I wanted to be “Rochelle” for my boyfriend so badly, but wasn’t sure if I was ready. The outfit that I wore that day consisted of a flowing, red floral-print dress that went down to just above my knees, black nylon stockings with a garter belt, and 4 inch stilettos. I also wore my prettiest brunette wig, red lipstick, and shaved every inch of bodily hair. By the time I was finished getting ready, my boyfriend had texted that he was on his way to pick me up.
At exactly 6:30 my boyfriend arrived at my door with a beautiful bouquet of flowers. The first thing he told me after carefully examining me from head to toe was, “good god you are stunning as a woman!” … let’s just say I blushed for the first time in my life. Never had I felt such an exhilaration feeling of being treated as a Lady by a gentleman.
As we walked down the apartment staircase, he playfully teased at my struggles to walk down in my heels. Once we got to the bottom, it hit me… I had forgotten my purse. After all, I normally carried a wallet, so a purse was not a natural thing for me. My boyfriend being the gentleman he is, kindly ran back up and fetched it for me while I waited in his car.
On our way to the restaurant, I couldn’t help but notice the curiosity that my boyfriend seemed to have in seeing his male partner dressed in women’s clothing. I happily explained what my outfit consisted of, and we even ended up laughing at how clueless he was on the concept of my garter belt holding up my stockings. This is where I my knowledge on vintage women’s fashion came in handy.
When we finally arrived at the restaurant, my boyfriend rushed to open my door for me and held my hand as I stepped out in an attempt to be ladylike. Of course being the clumsy gal that I am, I snagged one of my stockings on the door panel and instantly became embarrassed. Somehow I knew this would happen but nonetheless did not feel the best… Luckily, after receiving advice from other crossdressing gals to bring extra hosiery, I easily replaced my ruined stocking with another in the ladies room.
Dinner was magical. I know for a FACT that I did not look 100% passable. But I also know that between the treatment from my amazing boyfriend, the beautiful waitresses and restaurant staff, I FELT like a woman.
After dinner we held hands and went for a stroll around the city. We’d get several stares from strangers but we did not care. We were ultimately very happy.
While I must admit that I left out certain details of the story, this date night was one that I truly will cherish for the rest of my life.
Thanks for reading ladies!
-Rochelle
@rochelle13 Congratulations Rochelle. I know you looked beautiful and had a magical time and it appears this is just the beginning for Rochelle.
Melissa 👠
@jincrocker Right?! It’s definitely different being in the woman’s perspective of relationships when you’ve always been used to playing the man’s part!
@rochelle13 Sounds like it was a wonderful experience for you Rochelle! It also sounds like you have a wonderful boyfriend. I hope for you it only gets better from here.
@ellyd22 Aww thank you Ellie! I’m an amateur story teller at best but I’m grateful you took the time to read about my experience! ❤️
Thanks for sharing this.
What a lovely night you had. Hopefully the first of many !
Lucy
@lucyb112 Thanks for reading my story Lucy! And yes I look forward to more experiences in the future.
That sounds like a really magical evening, Rochelle.
I hope that you have many more.
Aurora Lynnette
Sounds like a beautiful night out Rochelle. You’re a lucky lady and your boyfriends a keeper. I bet you can’t wait for next date night.
Cassie
😘💕
@cassiej Yes it was a beautiful night for sure Cassie. I’m definitely excited to see where the relationship goes and hope you can experience similar joys at some point too!
Rochelle -
What a lovely experience for you, I hope you have many more in your future.
XOXO
Suzanne
I’m glad you were able to experience that first date night as a woman. I gather this was your first night out in public, but perhaps I assume too much. If so, its normal to feel nervousness and the sense that people are watching you. Mostly they aren’t. As you spend more time out, you’ll become more practiced with your feminine presentation.
As they say, it gets better!
@kdahlenbergen Kim! Luckily this was not my first time out in public as “Rochelle”. Otherwise it would have been far more terrifying. But yes, I agree 100% that the more you practice and get comfortable, the more amazing the experience of being female is! Much love ❤️
Girl, we want to see pictures of that night!
What a lovely evening, thank you for sharing.
You had me at “try it out”, which has been my mantra for most of my life. Why not just try something new and different? If it doesn't go well, at least you tried and now have a new experience to bank. As you seemed to have noticed, trying it out can turn out quite well, as your date did. We need to push ourselves at times and not just stay in our own comfortable situation. Challenges such as going out on a date en femme allow us to grow and develop as individuals.
I have concluded that being passable is not a necessity, far from it. While I try to be as passable as reasonably possible, I know up close I don't, and I no longer care. We live in a time where most people don't care, and the ones that do don't matter. I use common sense when out en femme and avoid situations where I could get into trouble...i.e. avoid the wrong side of town, dark alleys, places where large numbers of teens congregate, etcetera. Most people do not care. Few bother to even look close enough to notice, even though those who do notice seem supportive by their kind eyes, smiles, friendly hellos, or little comments/compliments.
I hope you have many more dates, and your BF enjoys exploring the fun things women lingerie can lead to.
@jjandme Hi JJ! Thank you for reading my story! And it’s definitely nerve racking at times when I know that the outside world still sees the male version of me even when dressed up. But I’m quickly learning to feel comfortable with myself and hope to only progress from here!
Much love!
Tho I have never been taken out to dinner by a gentleman and dont think I ever will, I have dined out in the company of a female a few times. eg. My wonderful make up artist Michelle R. There's a story in my articles on this subject here on CDH.
As one of the "more mature" members on this wonderful site, I wore 2" block heels, so no hosiery disasters...
But I justw anted to back up your comments on how wonderful and happy I felt that night, sitting in a busy public place, enjoying the meal and wine and "being me" ie Catherine Louise Ryan.
Michelle even said as much.
Happy dressing (and "going public")
Caty.
PS this was "the night of the day" after I'd had my second personal bra fitting. Now that's something EVERYONE should do.
