Thursday, September 10, 2015

Happy 4 Year Anniversary!

This Blog has been going for 4 Years!!! I can't believe it. I know there have been many gaps in my posting but, Its still here. I'm still here. You are still here. We have a thriving Facebook Group. Thank You ALL for reading and for all of your support and stories. You are ALL wonderful people and I'm glad to be a part of your lives and I'm super happy that I have you in my life! Keep sending me your thoughts and stories and I will try my best to post and do what I can to support you!

I Love you All!

Pirate Pebbs

Tuesday, September 1, 2015

Interview with a Straight Crossdresser Dating Update!

Hello Friends! We have a dating update from my 3rd Straight Crossdresser Interview! (Linked Here)
So here it is, without further ado, Take it away Sienna!

 February of this year I met a woman. At first we talked as friends and because I thought we would only be friends I told her upfront about my crossdressing. She thought it was cool and asked the usual questions, "are you gay, bi, or straight?", "why do you do it?", "can I see a picture?". After the usual interrogation the topic rarely came up and we got to know each other. I asked her out on a date and we hit it off really well. A couple weeks later we were dating.
Everything was going smoothly until I sent her a pic of me dressed up one day. She asked me to not to show her that side of me because she didn't think she could handle seeing me that way. Initially, I was devastated. I have no problem with a woman not wanting to date me because I'm a crossdresser but it would hurt me if I was upfront about my crossdressing and still broken up with because of it.
We decided that we would give it time after that. We both had struggles when it came to dealing with the situation. She thought that maybe one day I would come out as Trans and my feelings for her would go away. My girlfriend is pansexual so it's safe to say she would date me if that ever were the case, however she was worried about my feelings changing.
I, on the other hand, was worried that she wasn't attracted to me anymore. I was worried she had seen me as a girl and was now ashamed of me. I contemplated not dressing up anymore and purging so that she could have a normal man for a boyfriend. For a short while I felt like how it was when I started crossdressing and was hiding it.
After telling her about it she told me how she felt. I reassured her that my feelings would never change even if I wanted to change my gender. She told me she would never want me to change just for her. She wanted to love all sides of me and that meant me as a girl too. She had made it clear that she wanted to see me dressed up.
I was still nervous for a bit afterwards. I thought her reaction to me dressed up would either make or break our relationship. Eventually that day came and I dressed up for her. Since it was the first time I opted against makeup and just wore a wig and dress. I was extremely shy because of what was at stake. To my surprise, she loved it. The first time she couldn't keep her hands off of me.
Months later and things are even better. I dress up occasionally. She even does my makeup from time. We have cosplay ideas set up for us where we both dress as female characters. She calls me princess so long as she gets to be the queen. My crossdressing initially threatened our relationship but in the end it strengthened it. Now we're stronger than ever.

Thank You Sienna for sharing this part of your life with us!

I LOVE that Sienna shared with us a fresh faced picture without makeup. You are beautiful as you are. You don't need to hide your face. If you like how you look without makeup, you can wear Your face! If you want to add a bit of color you can do so as well. Either way you will always pass as...Human! That's what we all are. No matter what changes we make to our bodies, genetic testing will say that we are undoubtedly human no matter what.
If you would like to be featured on the blog with your story you can contact me at
Until next time, always remember...
Pirate Pebbs Loves You!