Monday, November 3, 2014

Perfectly Flawed - A Guest Post By Samantha Prescott

I have been extremely busy lately and haven't posted much lately. I apologize for that. I do have Awesome friends who are willing to help me out. This post is by Samantha and she's going to let you in on a bit of her life. I hope you enjoy and post your feelings about it here or you can chat about it in our Facebook Group or Page.

Take it away Sami.

Before I go back to the beginning and recant any recollection of when this all stared for me I will start with who I am at this exact moment.

    My name is Samantha "Sami" Prescott and I am a soon to be 50 year old happily married heterosexual crossdresser. I revealed the innermost me to my wife very early on in our relationship. We were becoming very involved quickly and I knew I could not wait another second. I was born into something that I didn't have a choice or say in and my own life experience that who I am was never going to change or just go away, I knew that she needed to have a choice to stay or walk away. I needed to be free of the secrecy and shame that my life has been accustomed, and I owed it to both of us to be honest and upfront to insure that would be a foundation on which our relationship would be built. As a result, one of the hardest decisions I ever carried out in my life, and one of the biggest risks I decided to take, I am very blessed and fortunate to have a supportive and accepting wife who has encouraged me to not be ashamed of who I am. Without understanding she stayed and she has been the one and only reason that I have found acceptance and peace within myself.  Without her support I might not have ventured out from the safety and confines of my home.

    I have been getting out and about for a little over 2 years now and have been working on my head to toe transformation and presentation for about 9 years, but 'I' have been a lifetime in the making. I am non-transitioning and very part time. I am closeted to everyone except my wife and I am not looking to make any drastic changes in my life nor seeking to come out and be full time. I do have a desire to get out a bit more often and know that I want to be able to be active in the community, provide help and support for other like myself, and also make a positive impact on those I interact with along the way.  Going a bit further in my self realization I also consider myself to be transgendered.  I know there is more to all of this than the clothes, I have no conflict with my gender, my identity, or my sexual preference. I do realize there is a duality that exists in me, a feminine aura, and a certain comfort and wholeness that comes with my drive and desire to nurture and outwardly express this part of me that I have hidden and denied for the largest part of my life.

    Going all the way back I could make this very short and say the day I was born I fell right into a pair of panties and took off running. That could very well be but my earliest recollection was when I was probably around 4 or 5 years old. I was in one of my mother's satin nightgowns. It extended way past my feet so there was no chance of running to hide when she was half way up the stairs and quickly approaching. As she is calling I lifted the lid of the hamper and tumbled in to hide. The lid opened right after but the hiding lasted for the majority of years afterward. It was my attraction to silky and satiny clothing and everything that was hidden under what a woman wore underneath the top layer that everyone would see excited me. The feeling against my skin was then and is still now incredible. I don't know why back then at such a young age I was so conflicted that something that felt so good to me was something that made me feel as if I was doing something so wrong. It was also those thoughts way back then that had me keeping all those things to myself.

    Within the next 2 or 3 years I was already into my mother's stockings, bras, panties, girdle's, pretty much everything and anything I could get my hands on. I was already hands on in self exploration before most boys or girls even had a clue as to what the real difference was between the sexes were. I can remember watching "Bewitched" through much different eyes than most children did, unless of course they were like me!

    Elizabeth Montgomery, who played Samantha and who is the inspiration in my name, was just a witch who was a mom and a homemaker on the television show. She was so much more than that to me. She was the essence of woman-ity and femininity, she was everything that I adored about a woman and the thought of what she was wearing under her dress had me thinking way past my mother's lingerie drawers.

    Then there was Jeannie, Ginger, and Mary Anne, the sitcom starlets who I wanted to emulate and larger than life when it came to how I was inspired by them. They were a vision of desire that I saw back then and very instrumental on how I present today.

    Somewhere in that time frame my mother asked me what I wanted to be for Halloween, before that point I was never asked, she just slapped a costume on me and off I went. Well, given a choice the obvious answer was "A Girl" so she borrowed a bunch of things from one of her girlfriends daughter's. Little did I know that I would be in my glory and I certainly did not show it, there I was wearing a cute blue dress with a strawberry pattern on it, a pair of white tights, and a pair black patent Buster Brown Mary Jane flats. I was all anxious to run out the door to go Trick or Treating and my mother stopped me and said, "You're not ready yet".  She pulled a wig down on my head and smeared some rouge blush on my cheeks and said, "Now the girl is ready".  I can remember one  of the ladies that answered the door saying, "Aren't you just the prettiest little girl".  Halloween wasn't the only time I slipped back into that dress. I can say that memory still brings a smile to my face today because I was somewhat embarrassed by it at that time.

    Two of the biggest disappointments after that was the day my mother returned the clothes to her girlfriend and years later when the day came that my feet would no longer fit into my mother's heels. So it wasn't long after that I had to muster up the courage to go and buy my first pair of heels. I also bought a bra, panties, and a matching garter-belt set and stockings which all became part of my first and only purge when I was married for the 1st time at 23 years old.

    I thought that was going to be the end to my secret to never surface again. Not so, it was not long before I was back to dabbling and I decided to come clean shortly before the birth of my 1st child. It did not go over well and was something that was not accepted or supported. Over more than 10 years and the birth of several more children I lived my life secretly, hiding my dressing. I was made to feel as if I were a freak and deviant by my former wife. My dressing was always something that was a sore point and always used by her as a weapon to make me feel ashamed of myself or to belittle me.

    Once that marriage ended and time passed I knew that I could never live that way again and also knew that if another relationship was to develop that I could not keep this part of me a secret. I have always lived my life and existed somewhere between blessed and cursed.

Back to where this story all started. Considering that I and my current wife never asked for any of these things to be a part of our lives, the only thing that I could ever hope for has become a reality for me. I have a wife who loves me for who I am as a person and someone I don't have to feel ashamed to be myself around. Cursed is no longer a part of the equation and as of now I am the closest to blessed that I could have ever hoped for, and a realization that although nothing in life will ever be perfect. I can accept and live with the fact that I am and will always be perfectly flawed.

Thursday, August 28, 2014

Sorry I haven't updated in a while.

I'm still around. I've been soooooo very busy lately. I feel bad that I haven't posted much at all. Not even on FB much but i'm there. If you haven't already Please join our Facebook group. Straight Crossdressers & Friends Facebook Group. I do screen the group to make sure there are no bots are spammers. I will send you a message, so make sure you use a profile that is able to receive messages otherwise you won't be added to the group. I'll ask you a question from my personal profile & You will need to respond back. If you respond back in a spambot-ish way...well...i'll keep talking a bit with you and as long as I know you're human and you agree to the rules ( if posting pics they must be appropriate for kids to see cause a lot of my group members have kids, myself included and we don't want our kids looking over our shoulders & seeing porn on our screens...i mean...there are other groups where that is acceptable but Not in our group).

I Love you all & think you are ALL wonderful people!

Here is a Pic of Me, Pirate Pebbs, from my recent trip to Otakon! (Anime convention where I often dress as Me, Pirate Pebbs)

Love Always,
Pirate Pebbs

Sunday, July 6, 2014

Raven couple months ago...

Hi everyone...Looks like I'm still having difficulty posting every week. Anyway,  I went to Raven #20 last weekend and it was über fun (as usual) I got to see some old friends and meet some new ones. I'll link to pics when I can. Started off Friday night. Went to the Bar at the Ramada Inn where they had the meet & greet. The Meet & Greet started out as a small welcome to the 'girls' who came in from out of town so that they could meet some new friends and won't feel out of place for the main party on Saturday night. Fast forward to now and its day 1 of a 3 day event. Day 1: Meet & Greet where from 8-ish PM till 11-ish PM Meeting and greeting happens. I often say Hi the everyone i know & meet people i don't know. I am quite talkative and wind up talking to some people or a person for a very long time before meeting more people and talking for even more time. I usually have a friend or 2 drive up with me on Friday nights but this time I was solo. I kinda liked it because I didn't have to leave early unless I wanted to etc. It was nice. Only thing was I didn't have a designated driver so I had my 2 drinks around 9PM and no more.

then Dancing at 'The Raven' (actual name of the place where the Raven Parties are held) I'm pretty sure Friday nights are 70's or 80's music nights. They have video's that play for most of the songs. Some of the video's I've never seen before.

Okay so this post was from a couple months ago but never finished. Posting it now because.... well its been a few months and if I don't post it now it'll probably never get posted and I need to get it out so I can move on to the next one. Raven 21 was this past weekend so...I'll write a bit about that one next.

Friday, May 23, 2014

Major Fail on my part

I had planned on posting once a week....I failed miserably this year. Thing is I have a new-ish Job and I didn't realize i'd be so drained after working. Not just that, my 10 yo daughter needs a lot of my time & my Sweetie is also time consuming. Tuesday next week is the 2 yr anniversary of my first date with my crossdressing sweetie. He is elated that i've been with him so long and hopes we'll stay together...well...forever.

Anywho I will leave you with this:

Yes...Eddie Izzard!!! That's just the clip w/me. I'll post the full video as well a lil later.

I love you ALL and have not forgotten about you. I have friended a few of you on facebook and many of you have liked our Facebook page and more & more of you are joining our Facebook group! Keep joining, make posts, make friends, and also remember....all ages page, no NSFW pics PLEASE. There are PLENTY of other groups that are all about the NSFW type pics. Thanks!

Pirate Pebbs

Wednesday, March 19, 2014

Convo with a CD friend #1 of Many

I was talking to one of my Crossdressing friends the other day. We were talking about clothes, dressing, relationships and such. At some point she says,
*”You are very out there, why can't I be someone like that, loyal and honest and don't care [about what others think about you]?’

My Response: It takes a bit of...well...getting over yourself. I got over myself. Embarrassing things are gonna happen, people are gonna not like some things you do. People are gonna try to put you down, question do you feel about you? Do you like what you do? Do you like who you are?
People come and go, you will be with you all of your life. You should take care of the inner you. The inner you wants to be happy. The inner you likes to dress a certain way and act a certain way. The inner you may want to look different every day. The inner you may wanna dress the same way for a week then totally change up. If you're with someone who can't deal with you being you...well...I don't see how making your inner self sad to make someone else happy will keep you happy for too long.

That was spewed out in the middle of the night when my friend was sleep. Later she responded:

“Wow Pebbles, You just broke it down, But you are right.  I see what you are saying, WE are some [of the] good men out there. Just because we want to dress like a woman doesn't mean we want to be with one or be gay or bi or anything like that.”

Me: Nearly all if not all of the CD dudes I chat with are really nice people & really 'good' guys. If a GG wants to be treated 'right' I highly recommend a CD. If the GG can get over themselves maybe they can find happiness in the arms of someone who just Might look better than them occasionally, lol. A lot of people don't get over themselves till they are way old. You don't see (some)old ladies not doing stuff or saying stuff just cause it might be embarrassing... life is too short to dwell on dumb stuff!

Later, We were discussing relationships again and the GG my CD friend is dating.

Me: I wanna say something which may come off pretty... 'guy-ish' and I'm not talkin’ nice guy... Here it goes. If you think she is your One, you should find a way to tell her you like to dress. If she's not...well...are you ready to drop her in a minute if you do find your 'one' who is fine with who you are?
I totally understand companionship. I didn't like being alone [when I was single].

Their response: ‘Well she’s somewhat one, but what is the one?... I'm 35 years old I don't know what to believe in that aspect. I would think the one would have come by now.

Me: So many of my CD/TG friends are with people who don't like a very real part of them...the emotional turmoil they go through because of it is really heartbreaking!
I had a friend show his girlfriend a picture of him en femme to come out to her. She thought he was really cute. They continued to date for a while, eventually they broke up, but not because of his dressing.

I wish I could talk to all the 'girlfriends that don't know' and ease them into the thought of it. CD guys (in my opinion) are just sooooo much easier to deal with than 'regular' guys. You Know what their major quirk is, that secret is gone! If you can deal with that, everything else will be a breeze to get through! And if you tell her & it doesn't work [or she thinks she can’t deal with it], well, you didn't invest TOO much time in a relationship that wouldn't work out in the end anyway

Why is a CD guys so much easier?

Me: More in touch with their feminine side...for example. [Some] Ladies sometimes (or all the times) wanna get their hair/nails etc done, right?

Yes they do.

Me: My ex hubby didn't understand that and to him it was kinda wasted money...his mom had to talk to him about that.

Oh yes we wouldn't mind getting ours done too.

Me: Exactly! No fight no fuss. That's something you can do together! Spa day, hello!

Later we went on to talk about how women may not like to participate in their significant other’s crossdressing. It’s like any other…we’ll say ‘hobby’ for this example. If I dislike something that someone likes to do, that doesn't mean I won't support the person who wants to do it. I may or may not join in on what they like to do. I may or may not be there every time they’re doing whatever it is they’re doing but I’m supportive. If someone I’m with likes table top gaming but I’m not into it. I wouldn’t put them down for it. I might try to play to see if maybe I could get to like it but if I just don’t like to do it myself…it’s just something I don’t like to do. They can continue with it. I might even make snacks to serve to the gamers or hang out and watch/listen to what’s going on.

I hope other people can be like that. If your significant other likes to dress in a way contrary to their gender type, would you be able to support them even if you’re not in to it? Can you help them with their hair and make-up so they can hang with their friends who also like to dress? Will you go to an event with them even though it’s not an event you want to go to all the time just to support them? It’s my hope that sometime soon this will no longer be considered a taboo…maybe even be considered a some-what normal occurrence.

That’s all I have to say for now. I hope you all have a GREAT DAY!!!

I will again be making an appearance at The Original GLBT Expo in NYC this weekend! I will be interviewed in the Video Lounge on Sunday. I’ll Have pictures and my experience from there to share with you soon!


Pirate Pebbs

*Bold Print (for the most part) is my CD friend’s words.
CD= Crossdresser, GG= Genetic Girl=Cis-Gendered Female=Female who was born female and identifies as female.

Monday, March 3, 2014

Our Frock Magazine 2014 Cover Girl Contest Entrants

Three Straight Crossdressers I know are competing in this contest. I would LOVE it if one of our lovelies would win! You can vote for all three of them by clicking their links and clicking vote.

One of them was interviewed last year in our 'Interview with a Straight Crossdresser'
Here is Gia!

Click Here to Vote for Gia

Next is the winner of our 500 Likes on Facebook Poster Contest.
Here's Tabbitha!

Click Here to Vote for Tabbitha

Last but not least is a more recent Facebook friend and aspiring Model.
Here's Paige!

Click Here to Vote for Paige

Good Luck to You All!!! I wish you ALL could win but if not all of you at least one of you!

~Pirate Pebbs

Wednesday, February 26, 2014

Support Matters - Guest Post by Chardonnay Merlot

It was a Saturday night out on the dance floor. Me with a big smile on my face. You can never get too much of the feeling of a fun night out, surrounded by friends, all while working the perfect outfit.

The added bonus? For me, it was at the place where my journey truly began.

On that night two years before,-- IChardonnay Merlot, stepped out into the world for the first time.

I was alone, nervous, scared. I wasn't sure I was gonna go through with it.

My Heartbeat keeping time with the click-clack of heels on a parking lot.

Earlier that day, I was in a dressing room at a small shop maybe an hour away.

Looking in a mirror at me.

It was overload seeing myself in a way I'd always wanted to but never felt safe in doing.

And then I was told, "You really should consider going out tonight. There's nothing gained by hiding who you are."

I ended up going to a club that night. Nervous to the point of nausea.

"Don't be nervous honey, be out and be proud."

I met others like me that night.

A couple of weeks later, I was late to my first meeting with my support group and the group leader gave me the 'Don Rickles' treatment for being quite late, and then embraced me... as did the whole community.

The common denominator: Someone reached out.

I'm grateful for so many who have, mainly in a lot of small ways, from besties who call and Facebook me just to ask "how ya doin?" to those who have shared their experience and wisdom with me from the beginning.

Those first steps were tentative and nervous. Looking back I wonder how ever got the heart to take them.

It was because somebody took one second to tell me, "Live it. Learn it. Own it."

Because somebody took one second to show me how to use a foundation brush more efficiently.

Because someone spent an evening sharing their journey, their story, and was patient with me.

Because a group of people invited me in with open arms.

Because a group of people saw a shy scared person trying to find answers and they took me in.

Thanks to that, I've found a new peace, a new strength and have expanded my circle because of it. The journey feels a little less arduous and a lot less lonely, because from the beginning so many, in big ways and small, sent the most important message: "You are not alone."

 Support Matters

-Chardonnay Merlot

Sunday, February 23, 2014

Links & filler

I have had an uninspired week. Nothing really to talk about from my life with CDs but I DID read an article that was AWESOME couple. A transvestite & his Wife. A sweet beautiful loving couple in california. They had a write-up in LA Weekly! Below is a link to the article.

I'm pretty sure I read this on another blog about crossdressing. Here are a few links to other pages i frequent (some are crossdresser themed, some are art themed). I'm sure none of the CD blog owners even know this page exists...i'll reach out...eventually...maybe...

I have at least one interview on the back burner that hopefully I will get to this week. Also a friend & reader of this blog has written an article which will be posted soon as well.

Love Always,

Pirate Pebbs

P.S. I'll be at the GLBT Expo in NYC Next month in the Video Lounge with Appolonia Cruz! Check me out there if you'll be there as well :)

Monday, February 17, 2014

Happy Valentines Day 2014

Happy (belated) Valentines Day!

I had a really special Valentines Day. Its been about a year since I've been dating my sweetie exclusively. I told him I wanted him to write me a 'love letter'...just cause I wanted one... Then, he told me he wanted one in return... total backfire on me cause it hadn't crossed my mind that he'd want one back. Not that he didn't deserve one back, just cause when I mentioned it it was something that had come to mind seconds before I said it. Anyway, I'd been thinking of what to put for days & telling my bestfriend what I planned to put in the letter. Come letter writin' time...I just had randomness. Then I had to do a bit of driving, took the best friend with me to finalize the letter on my cellphone. We got everything hashed out beautifully! ...Then...while I was cookin' Bacon Roses for my sweetie, my greasy hands was making the phone glitchy. I attempted to save the letter... long story short, it got erased. *sigh* I did tell him in advance of his arrival what happened & he was fine with it. I did wind up telling him what i'd written way less eloquently than it had been written. Any who, he did write me a letter and it is pictured below. I share this with you as a beacon of hope. Have a read. I have more to say below the letter.

This letter was written by my sweetie, a 33 year old crossdresser. A person like many of you who has gone through countless years of loneliness. Not just because he didn't have a girlfriend. When he did have girlfriends they didn't know about his crossdressing. They didn't know all of him. I hope in reading this, whether you are a crossdresser who is currently alone or a GG just learning that straight guys can crossdress and still be just as much of a man as a guy who doesn't, you can see how life changing one person can be to another. No matter who you are, what gender you do or don't assign yourself, that there is someone out there for you. Sometime the wait can feel like forever. Sometimes you have to wait longer than you think is reasonable. You can meet the person your heart yearns for. They may have to be chased. They may not know or even think they are the one for you. You may have to spend a year convincing them to give you a chance. When they finally do, show them how much they mean to you and how special you think they are and continue to do so in case they forget. Some people need to feel needed in order to feel happy in their relationships, remind them why you need them.

...Ok, I feel like i'm rambling. I should probably stop & get some sleep. **(I will edit this and fix all the capitalization issues etc once i've gotten enough sleep)  

I wish you all Love!

If no one else, 

Pirate Pebbs Loves You!

**All edited and fixed :)

Sunday, February 9, 2014

Messages from Readers #1

Since I started posting about my blog in various profiles that i've used for dating over the years, I gotten a few letters from readers…ok…more like comments from readers and I want to share some of them with you. I’m just gonna abbreviate their names or their screen names so as not to expose them w/o permission (if your screen name happens to be one of the abbreviations, it is simply unintentional). I will be posting more in upcoming posts. If you see your comment here and would like me to put your screen name or real name just email me at
These were left as messages in my OKCupid profile.

Pirate Pebbs
4/18/2012- Hey, just a friendly message! As a straight guy who dresses up, I can appreciate your blog! Thanks honey!

5/17/2012- Hello, I read you blog and it's awesome! Immediate add to my reader. It's good to know there are well adjusted women out there who can appreciate people with my certain disposition. It makes me want to branch out and make a real attempt to find someone, but you are right. Nine times out of ten it doesn't go well and now I have resorted to telling new interests up front before the first date but usually it turns out there is no first date! lol. Anyway this is turning into a ramble. Thank you again. 

7/6/2012- are in inspiration! :) 
I am a straight man, and have been crossdressing for quite some time. Actually, I have not worn male underwear for about 5 years. Even at work, underneath my slacks, you will always find a pretty pair of panties. :) 
I just thought about saying hello, and to thank you for being so open minded. I wish more people were like you. 
Now excuse me while I go do my laundry, full of panties, stockings, and bras. :)

2/7/2013- I am a male crossdresser. Thank you for your kind words, and your blog. ITs very big of you to put a voice out there, and realize, most men are straight that do it. Thanks!
9/165/2013- You sound like an amazing person!! It's gets exacerbating with women who automatically assume I'm gay or want a sex reassignment simply because I enjoy wearing makeup, dress and pantyhose! 
So good to know women like you exist!

10/29/2013- Just wanted to say I really dig the blog.


Monday, February 3, 2014

The post that should have been...and will be

Ok, so my plan was to do a post of letters from the readers. I have gotten quite a lot of praise from people who read this blog and support what I'm trying to do. Within the next few days I will get that up and posted but I have been so busy with work, family life & being at a planning meeting for biggest (and best my opinion) anime convention on the East Coast. Also hosting Karaoke...Yeah, i've been kinda busy. So I am posting this now and hopefully I can get my post done soon.

More to come soon,


Pirate Pebbs

Sunday, January 19, 2014

RuPaul's Drag Race Battle of the Seasons at the Troc 2014

This week, on January 16th, Paula & I went to the Trocadero in Philadelphia where Drag Race Contestants from several seasons were to perform. The night was hosted by Michelle Visage and starred Manila LuzonPandora Boxx & Sharon Needles  Ivy Winters, Alaska Thunderfuck, Mimi Imfurst & Phi Phi O'Hara with special guest Jiggly Caliente. 

I missed out on getting VIP tickets this time (those tickets sell out fast) but I at least had tickets for the show. When I go to a drag show I want to look like I at least Tried with my make-up (ok, i couldn't remember where I last had my foundation so that wasn't worn). I think I did well. I looked quite ...noticeable. It was a standing room type of establishment on the floor. We decided to stand a lil bit off from the stage to a slightly higher area where I could see what was going on well. The only con was that I wasn't allowed to bring my dslr camera and had to use a Canon Power Shot. Everything looked further away than what it really was. Ah well, what could you do?

The Show started with Michelle singing a version of 'Science Fiction Double Feature' from Rocky Horror Picture Show. Then went on to performances. I was pleasantly surprised by some of the performances. There were video clips interspersed in the show, before & during performances. Lots of live singing as well as a good deal of lip singing. Carmen Carrera was supposed to be there but couldn't so Jiggly Caliente stood in, which was cool. Ivy Winters did a few performances on stilts as well as juggling knives & eating fire. Pandora Boxx did an awesome comedy routine. Manila did a great...everything! I Love Manila's style & all over zaniness. I recommend anyone who can to see the show. They are performing in a few more cities together. 

While I was at the show I saw someone that I thought i'd met before, turns out it wasn't. But Long story short, I made a new friend. A local CD named Trixie whom i've been chatting with in the days since. Seems like a pretty cool person. You never know who you'll meet when you go to shows. I also saw one of my Karaoke friends at the show.

After the show there was a free after party at club Voyeur (for the people who went to the show) where a lot of the Queens from the show were going to. I went over there and they had their weekly drag show still happening. So I saw a few of philly's local drag queens. Some I'd seen before Like Satine Harlow & Lady Poison, as well as some I'd never seen before. There were maybe 6 performances left that I was able to see. All were enjoyable. During the ending of the show a few of the queens who had been at the Troc were in attendance. I saw (ok ...kinda chased down) Manila and told him how Awesome I thought he was...wish i'd had my camera out...whateva. Anywho, I went home around 2am happy that i'd had a chance to go and see some awesome performances!

The following is a link to the rest of the performances:

Here are a few pics & a link to all the pictures I took with my non-DSLR camera. RDR BOTS Pics

Sunday, January 12, 2014

Interview with a Straight Crossdresser #4

This week we have an interview that I started 6 months ago and through a series of events going on in my life, I.... didn't finish. Now, thanks to their reminder, It has been finished.

This week we interview 18 year old Victoria from Whittier, California.
*Victoria in the white satin top.
Pebbles: About when did you become interested in or start crossdressing?

Victoria: I started around the age of 10 with my moms bras and slips, but then stopped once I got into middle school. After that I didn’t really start doing it again until 2011, my junior year of high school and that's when I started buying my own clothes and creating 'Victoria'.

Pebbles: Where did you go to buy your first items of clothing?

Victoria: eBay, the first item I ever bought was a white satin top. In fact it’s the one I'm wearing in my profile pic*

Pebbles: Very cool!

Pebbles: Have you ever been 'caught' crossdressing? If so, by who? What was the outcome?

Victoria: I have been caught with the items (clothes, wigs and such) in my room by my mom and she's confused by it but she never really confronts me about it. But caught fully crossdressed? No not yet thank goodness

Pebbles: I hear ya!

Pebbles: Does any of your family know you 'dress'?

Victoria: Yes, my cousins Janelle, Marissa and Jessie, whom I'm close with know about it and are very supportive. Janelle and I are especially close and we often exchange christmas gifts. I just came out to her a few months before and she got me an e.l.f makeup kit!

Pebbles: AWESOME!!! I love the family involvement!

Pebbles: Have you ever gone out crossdressed in public?

Victoria: Yes, yes many times. Since going to college I have gone out in public on campus, to the nearby business and around my neighborhood, with some special memories on a few occasions.

Pebbles: Care to share a memory?

Victoria: Oh, there's so many. So I'll share a small sample a few. Going out crossed for the first time outside of campus to the real world; Going to 7/11 and 'Stater Bros' all due to my professor. Halloween: Going to a salon, getting my wig done and going to class startling my classmates who couldn't believe it was me. 
Going to get a pedicure with a friend of mine and being treated like two princesses. 
And sneaking an outfit into a family christmas party and showing my cousins ‘Victoria’. So many precious memories in only 4 months of going out dressed in public!

Pebbles: WOW!!! Those are some Great moments! Thank you for sharing.  

Pebbles: Did anyone teach you how to apply makeup? Do you have someone do it for you? Are you learning/ have you learned through youtube vids?

Victoria: Nope, self taught. But for me its easy since I really just do eye shadow, foundation and lipstick when go out. I really don't do elaborate makeup like other crossdressers. Only when my cousin Janelle gave me the e.l.f makeup did someone else do my makeup for me.

Pebbles: That's cool. You don't need to go all out make-up crazy. In fact, for the most part, less is more. 

Pebbles:Do/Have you worn fake nails or nail polish?

Victoria: I haven't worn fake nails yet, but I have worn nail polish. I get my nails painted everytime I go for a pedicure.

Pebbles: Awesome!

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

Victoria: I always want to pass because it makes me feel good and empowered. I honestly think I could do a little more to pass better, but I think I pass at a good enough level. Although even if I didn't I would still go out because I love going on adventures.

Pebbles: That’s cool.

Pebbles: Do you tuck & Shave when you crossdress?

Victoria: I shave my face and neck every time before I go out. So much so I actually got an electric razor for christmas. I do tuck but very lazily and not super convincingly.

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

Victoria: Feeling pretty and alive makes me want to crossdress. I love the feeling of lipstick and gloss on my lips, how beautiful I look when I put my wig on and inspecting myself in the mirror. I feel elated and happy when I crossdress, just the feeling of satin and sandals give me a feeling of calm and contentment that nothing else can make me feel.

Pebbles: Ideally what percentage of your time would you prefer to be 'dressed'? Like...if it was a month. 50% dressed, more/less?

Victoria: Haha, that's a good question. I mean I LOVE dressing up and I would be Victoria 100% of the time if I could. But at the same time I like being a guy and not having to act prim and proper. I kind of compare to an experience had at my high school's football games. I would love looking at the cheerleaders because they were so attractive and beautiful, but at the same time I would long to be one of them cheering on the sideline in uniform and makeup waving my pom-poms around in white shoes. So even though Victoria would love to be out all the time, she can get nudged aside pretty quickly.

Pebbles: lol! So, more like 50/50-ish or more like, 'when the mood sets me'?

Victoria: 50/50 I suppose, lol. A long analogy to get to a simple answer, haha

Pebbles: lol, its a good one though

Pebbles: Are you currently dating anyone? If so, does she know?

Victoria: No,  I'm currently single.

Pebbles: Have you had one since you started crossdressing?

Victoria: Thank you and no I haven't dated yet since becoming Victoria.

Pebbles: Well, I'm sure that will change.

Pebbles: Is there anything else you would like the public to know about you? Or do you have an interesting story to share?

Pebbles: By the way, looking at your pictures, You are ADORABLE!!!

Victoria: Thank you so much. Yes, I would just like to thank all of the people who had helped me over the past few months. My English/Speech professor Ms. Maya Staylor actually help me go out in public for the first time (outside campus) and was always welcoming when I came visit as Victoria, I owe her a lot for encouraging me to become Victoria and I enjoy every moment of it. I would also like to thank Lihn, the stylist who does my wigs, she is so welcoming and sweet everytime I go and makes me look so beautiful, I encourage any crossdresser in the Walnut area (in California) to visit her at Newen's Beauty Salon (909)910-623 Tues, Thurs. And finally I'd like to my friends and family for being so encouraging of Victoria and letting me gush over my adventures as her.

Pebbles: AWESOME!!! I'm so glad you have such a GREAT support system! Thank You for interviewing with me!

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

Until next time, Have fun & stay safe!
Victoria's First time out!

Love Always,
Pirate Pebbs

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