MEET TODAY’S GUEST
RachelTV38
Rachel's crossdressing journey began at ten in a cheerleader uniform, her sister's idea, three layers of tights, and a Halloween night that left a lasting impression. Elegant, sexy, and stylish are her three words and she lives up to all of them. At over 6 feet tall in heels she doesn't always choose to wear, Rachel has spent years perfecting an authentic feminine presentation that turns heads without trying to. Part-time crossdresser, FetLife favourite, and someone who has been taken to a private lake club by a very well-known gentleman. She holds tightly to her principles, knows exactly who Rachel is, and is already thinking about when it might be time to say goodbye. Until then, she's making it count.
Before we begin, a word of gratitude.
To Rachel: thank you for your honesty and your self-awareness. In a world where crossdressing content can sometimes be all fantasy and no reflection, you bring something rare. A grounded, principled perspective that reminds us all to know our why. That matters more than you know.
To our readers: eight interviews in. You've shown up for every single one, from the very first issue all the way here. That's not nothing. This newsletter is still finding its feet and the fact that you keep opening, keep reading, keep coming back means more than I can say in a subject line. You're not just subscribers. You're the reason this keeps going.
Now, you're about to meet someone who has been wined and dined at a private club, navigated the attention that comes with being genuinely stunning, and still held onto her values throughout. This one is equal parts aspirational and real.
This is just the beginning, and I'm grateful you're here for it.
THE INTERVIEW
What was your first time dressed like? Do you remember the outfit and the feelings?
The first time I dressed was age 10 and it was actually my sister's idea. She dressed me in her cheerleader uniform for Halloween, did my makeup and hair and I remember wearing 3 layers of tights because it was cold out. I was shy, but nobody could tell it was me. I got all kinds of attention and it was pretty awkward but it made an impression of desire on me that I later started to become more curious about. I didn't dress again until after high school when I was out on my own in an apartment.
Describe your signature style in three words.
Elegant, sexy, and stylish are good ways to describe me.
Who or what inspires your look?
I love to pay attention to the little feminine details and get things just right to create an authentic, not over the top feminine look.
Walk us through your getting-ready ritual. Where do you start?
I guess I start by putting on my bra, panties and nylons and then proceed with my makeup. The prep and makeup takes about 90 minutes and sometimes doesn't cooperate like I'd like it to, but oh well…then I'll finish with a dress or skirt and top, add the jewelry and finally fix my hair and nails. It takes me about 2 hours start to sexy…
What's the one makeup product or technique that changed everything for you?
Learning eye makeup and contouring takes a lot of trial and error to find out what works for your face and its overall balance.
What's the most challenging aspect of presenting feminine? What comes most naturally?
My most challenging aspect is my height. At over 6 feet, I have to choose appropriate clothing and style for the occasion because i try to present authenticity, not flashy extravagance. Heels are a favorite, but not for every occasion.
How do you identify? (Crossdresser, gender-fluid, trans, other?)
I'm a part time crossdresser.
When you're dressed, do you feel like a different person or more authentically yourself?
I don't feel much different or sense that I'm more authentic. I just love to escape to a totally opposite persona than my every day existence.
What has been the most supportive response you've received?
Well I have many admirers on Fetlife and I'm grateful for my following. I'm continually amazed at how many find my presentation attractive.
How has the online crossdressing/trans community impacted your journey.
I really don't think it has had a lot of impact because I'm not out there doing the public stuff others are. I don't feel the need to be the attention grabber that some others are very good at.
How does crossdressing intersect with your sexuality? Are they connected or separate?
I don't know if it does. I seem to be attracted to the opposite sex of how I'm presenting at any time.
What's your most memorable experience dressed - whether romantic, social, or personal?
I would have to say being asked out and going out with a very famous and well known gentleman. Being treated to a dinner at a super expensive private lake club where he has a beautiful vacation home. And just being made to feel sexy and feminine was so nice!
Have you experienced attraction or attention while dressed? How does that feel?
Yes. I think a lot of people find me attractive and I generate quite a bit of attention. It's definitely more difficult to manage all of it without sacrificing bedrock principals and morals that define me as a person. I think it's easy to get caught up in the euphoria of it and the attention can become your primary pursuit where maybe it didn't start out to be. That can lead to bad decisions. I've certainly been changed by becoming Rachel, but I've always held tightly to my core principals and not sacrificed them for momentary notoriety.
I've certainly been changed by becoming Rachel, but I've always held tightly to my core principals.
Is there a dominant or submissive element to how you feel when dressed?
I definitely take on a submissive role when dressed.
Does crossdressing connect to any kinks or fetishes for you?
I do enjoy being restrained and controlled…
If you could live out any fantasy while dressed, what would it be?
I think doing a full wedding type makeover would be super fun. If love to see what I look like after a real makeup professional did their magic on me! Then of course…a wedding dress!
What's one product, hack, or piece of advice every crossdresser should know?
Makeup takes time and effort to learn. Practice with cheap stuff, but understand you get what you pay for in product. On line tutorials give the basics, then you need to do it, screw it up, learn, and do it again until things make sense.
Where do you shop? Any favorite brands or hidden gems?
It's hard for me to find sexy size 18 clothes! I'm always trolling second hand for everything. And sexy size 13 shoes are rare too!
What's something you spent too much money on that was totally worth it?
Good makeup! You get what you pay for!
Do you go out dressed? If so, where? If not, what would it take?
I do go out a lot. Most of the time it's just running errands around town, but I also like to go on dates when I can.
If you could be dressed full-time with zero consequences, would you?
I think it sounds fun, but I do enjoy my vanilla life. I don't believe i was meant to be a woman, but it is fun to be one on occasion.
Where do you see your crossdressing journey in 5 years?
Good question! I may actually retire Rachel by then, I'm not sure. I know that there will be a time when I don't meet the standards I have for myself and I'll know when it's time to say goodbye to Rachel. I'll anyways have the pics and memories though.
I know that there will be a time when I don't meet the standards I have for myself and I'll know when it's time to say goodbye to Rachel.
What advice would you give to someone who just bought their first dress and is terrified?
Figure out your WHY. Don't let others define it for you. I hear from a lot of beginners that want to look like me. The first question I usually ask is why…
There's negatives to every positive you see on the outside. So figure out what it is you're after.
Figure out your WHY. Don't let others define it for you.
Rapid Fire Questions
Coffee or wine?
Wine, but water is better.
Daytime glam or evening seduction?
Evening seduction!
Heels or flats?
Flats all day, heels all night!
Bold lips or subtle gloss?
Subtle gloss.
Lipstick shade you're wearing right now (or wish you were)?
Sephora, Sugar Dose
If you could leave readers with one image, feeling, or thought about crossdressing, what would it be?
Crossdressing will accentuate situations and feelings in your life. Like turning up the contrast on a television. It won't cure problems, solve conflicts, or mend relationships.
It can be a fun escape, but so can gambling! Like anything else, it can become enjoyable or lead to depression and anxiety.
Understand you're motivation and purpose. Have principals and stick to them.
Be respectful of others around you that don't share your views and have fun!
Who should I interview next? Drop a name in the comments.
Who should I interview next?
Drop a name in the comments.
Thank you!
This is just a glimpse!
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