Monday, January 6, 2014

First 'Interview with a Straight Crossdresser' for 2014

New Year, New interview! This interview is with Sienna, a 19 year old crossdresser from Las Vegas, Nevada.


Pebbles: Ok, Interview time!!!!

Sienna: LOL. Okay I'm ready.

Pebbles: So, how would you like to be addressed?

Sienna: We can use my girl name I guess. It's Sienna.

Pebbles: Ok. About when did you become interested in or start crossdressing?

Sienna: I always had a secret love of fashion but I didn't really think about crossdressing until I was about 15 or 16.

Pebbles: Have you ever been 'caught', if so, by whom? What was the outcome?

Sienna: Surprisingly I've never been caught. I think it's because I've only been doing this for about a year and a half and I'm pretty open about it already so a good chunk of people know.

Pebbles: Awesome. I've noticed it’s (seems) much easier for the younger generation to do it with lil trouble maybe people around 23-ish and younger are way more relaxed about it.
Does your family know you 'dress' ?

Sienna: My brother and two sisters know about it but my mom and dad currently don't.

Pebbles: Ah, cool. How do they feel about it?

Sienna: My siblings are extremely supportive. I've actually borrowed clothes from my sisters before.

Pebbles: When/how did they find out about it?

Sienna: They just found out in early October after a year of hiding it from them. I pretty much put a post on Facebook about it that only they could see. I figured that was the easiest way to do it.

Pebbles: Pretty smart!
Have you ever gone out crossdressed in public? If so, where to?

Sienna: The first time I ever crossdressed was at school. For spirit week we had Gender Bender Day and I was interested in crossdressing already, so I took that opportunity and dressed up.

Pebbles: Cool

Sienna: I've also been out on Halloween dressed up a couple of times.

Pebbles: Did anyone teach you how to apply makeup? Do you apply your own?

Sienna: My friend is currently teaching me how to do it. Right now I don't do my own makeup and go out because I'm absolutely horrible at it, yet somehow I'm decent at face painting.

Pebbles: Similar skills yes, but totally different results usually.
Do/Have you worn fake nails or do you paint your nails?

Sienna: I have not. Since I've started crossdressing I haven't done anything to my nails, not even paint them.

Pebbles: Ah, ok. Are you 'Passing' or is it your goal to be passing? If so would you go out in public crossdressed regularly?

Sienna: Every time I do go out dressed up people think I'm a girl so I guess I'm passing even though I don't think I am. I guess you could say it is a goal though because I want to look as pretty as possible. And yes I would go out regularly. I plan on going out more often.

Pebbles: What makes you want to crossdress? How does it make you feel?

Sienna: Ever since I was little I pretty much straddled the line for the gender norm. I'd play with my sisters and see them using barbies and then I'd go play with my brother and his wrestling action figures. So in a way there was always two sides to me. Crossdressing gives me a way to truly express that other side as well as indulge in my love of heels lol.

Pebbles: Sounds good! Do you tuck &/or Shave when you crossdress? Being that you're pretty young I figure if you shave, it’s not much, eh?

Sienna: Not yet I don't. For the most part when I've dressed up I've worn things that cover that area so tucking isn't really necessary. I haven't shaved either since a lot of the time I'm wearing leggings or something that covers my hair. Only thing that needs shaving is my beard.

Pebbles: Ideally what percentage of your time would you prefer to be 'dressed', 50% of the time more or less?

Sienna: Less than 50%. I'm happy just doing it maybe 2-3 times a month. Maybe a bit more if I'm really feeling like it. I would never want to spend a whole entire week dressing up though.

Pebbles: I hear ya! I girlified myself for a was torture...and I Am a girl. I did a weeks’ worth of posts about it...weird eh?

Sienna: LOL, that sounds like torture. Seems like most girls hate getting dolled up. They just like the end result, haha.

Pebbles: Yeah. Do you have a girlfriend, if so, does she know?

Sienna: Nope. For now I'm single.

Pebbles: Have you had one since you started crossdressing? If so did she know about it?

Sienna: Nothing serious. I've had a couple instances where I almost was in a relationship with some girls and they knew about the crossdressing and were okay with it but they weren't really official.

Pebbles: Ah, I hear ya.
Is there a female celebrity that inspires your look?

Sienna: I try to do my own thing when it comes to my look but I definitely love Kerry Washington's style. She might have a little bit of influence on me.

Pebbles: Cool. Do you have a story you would like to share with the reading audience?

Sienna: Well there's Gender Bender Day in high school. All the girls jumped at the chance to dress as boys but only two boys dressed up as girls and I was one of the two. So I get to class all dressed up, purse on one arm, makeup did and the teacher tells us there's an all boys assembly today. So I end up having to go to the all boys assembly dressed as a girl. The whole senior class died laughing at me. I think student council planned for that to happen. LOL.

Pebbles: LOL, yeah probably.

Pebbles: Is there anything you'd like to say to other young people interested in crossdressing or anything to say to parents of crossdressing kids?

Sienna: For young people who are interested I'd say, “Stop caring about what others think and just do your thing. Your real friends and family will stick by you no matter what you do.” “For parents I'd say just be open minded and accepting. They're still your baby. The only thing that is probably gonna change is the clothes they wear.”

Pebbles: Great Advice!
Thank you Sienna for having the time to be interviewed for my little blog in my tiny section of the internet

Sienna: LOL. No problem. Thank you for interviewing me. I don't get to voice how I feel about crossdressing often.
Also, I think what you're doing is a great thing. It may not be the biggest thing around but it still helps.

Pebbles: Awesome. My one major goal in life is to help people be happy

Sienna: Well I think you're doing a great job so far.

Pebbles: Thank you. I do try cause I want to help more people either with self acceptance, accepting their kids or accepting their significant other.

Sienna: That's good. I've actually considered starting a youtube channel in order to give other young straight crossdressers someone to relate to as well as promote acceptance too.

Pebbles: I think that’s Great!
Is there anything you'd like to add before we finish up here?

Sienna: I When I first started crossdressing I was looking for a straight crossdresser who I can relate to since there didn't seem to be many of them voicing their opinions. However this page ( helped since it let me know there are a lot of people out there like me as well as women who would date them. That helped me not be ashamed of crossdressing and instead accept it.

Pebbles: I’m glad I was able to help you out there. Thank you again for taking the time out to share your story with us.

So ladies, Sienna is single and looking. If you’re in the Vegas area and are interested in conversing with Sienna, you can send an email to with your name age and reply email (a picture wouldn’t hurt as well, I mean, you see Sienna right here) and I will pass the info to Sienna.

Until next time, Have fun & stay safe!

Love Always,
Pirate Pebbs

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