BEST GIRLFRIEND EVER
from Sissy Stephie

Dear Auntie Helga,

I have been going out with a lovely girl for the past eight months now, and only two nights ago did I finally show her my true self.

Some backstory is necessary here. I met Jessica when I started a new job, and she was preparing to transfer to a different location after a promotion. We both work in the library, and I sat down to talk to her when I saw her reading a Sailor Moon manga. I talked with her for a bit before asking for her number and we have been together since.

Things had been somewhat rocky, as I was not entirely keen on revealing what I am really like to her and she was able to easily pick up on it. I was hesitant to let anyone know, let alone a potential girlfriend, and most of the things we did involved spending time over at her place. While we did spend time at my house sometimes, I outright refused to show her my room as I knew if she looked in any number of locations where I hid my dresses, dollies, or diapers, the jig would be up.

Jess knew I had a secret, and would continue pressing me about it to the point where I had severe anxiety at work and at home. Even when I wasn't with her, I felt terrible about hiding this part of myself for fear of refusal to accept me for who I am, disgust over the things I love, or even worse, revealing to my work that I was a sissy. I was at odds with myself to the point where for a month I broke off and stopped talking to her for fear I would do or say something which could prematurely end the relationship.

She continued to reach out to me during this time. I, like the imbecile I am, thought I was doing the both of us a favor by seemingly sabotaging the relationship in an attempt to spare everyone's feelings. Luckily she was extremely forgiving of my faults, for when I asked if she would join me on a date again three weeks past the last time we'd spoken she was willing to give me an opportunity to explain myself.

I had placed horrible stress on her, making her think she had done something wrong and scared me off. She explained things were not going well at home for her, and things with her mother had become tenuous at best. I realized the best shot I had at remedying my errors here would be to tell her the truth about everything. When she finally asked again, I explained to her that I was a sissy, and that I enjoyed dressing in women's clothes. She didn't seem to understand that I had not meant dressing as a grown woman, and I felt the need to show rather than tell as telling didn't seem to be working.

I brought my powder blue set, consisting of a bonnet, rhumba panties with three rows of lace, and a short nightie with sewn-on pinafore. I also had a purple diaper with The Little Mermaid motif. I wasn't entirely sure about the diaper for her first time seeing me as a sissy except for her seeming to not understand what "being a sissy" really meant, or at least what it really meant to me. I also took along my dolly, Jenny, as Jess has a lot of stuffed animals herself and I thought she'd like to meet her.

I was sweating bullets throughout the whole lead-up to revealing everything to her. My backpack containing all my clothes and Jenny was left in my car, as I wasn't even certain I was going to show her after I'd already decided on it. As I mentioned before, I am very anxious about letting other people see this side of me, even if they mean as much as Jess means to me. After we'd spent some time in her room, she thanked me once again for telling her my secret. I took this opportunity to excuse me for a moment and retrieve my bag and waited for her to use the bathroom before changing into everything but my bonnet. I hid the ensemble under the covers, lying on the bed with only my head exposed when she returned.

I proceeded to ask her if she was serious about being okay with learning what my secret was, and she said once again that I was fine. She told me I had nothing to worry about, and I thanked her. Telling her I had something else to show her, I asked her to close and lock her door before coming over to the side of the bed. When she did, I threw back the covers and revealed myself to her.

She didn't laugh. She didn't scream. She wasn't fazed at all. Any number of terrible things I thought might happen, never did. She simply smiled, asked "So this is what you like," and I nodded. I let her onto the bed and went back to my bag, pulling out my bonnet which earned a laugh from her. I tied it on and took Jenny out of her hiding spot, then introduced her to Jess. After I returned to the bed, we laid next to each other and cuddled.

We spent some time doing that, and as I'd always wanted to have a girl's night in, I asked if she would like to do my makeup. She smiled and brought out several containers, one of which was a Hello Kitty makeup kit. This was the first time she had ever seen me like this, and we spent an hour working on what makeup would suit me best. She picked something cute for my eyeshadow, which is unfortunately barely visible. I have naturally long eyelashes so they were able to plump out wider than they've ever been. She helped me with a light blush and a glittery, cherry red lipstick.

That was Friday night, which turned into Saturday morning. After the picture was taken, we spent hours cuddling together and trading passionate kisses before falling asleep. I woke up to blissfully realize what happened the night before was not a dream, I was still dressed in my sissy outfit, my girlfriend still loved me, and I loved her more than life itself.

Since then, the past two days have seen a marked change in my personality. I was terrified to let anyone in, to do much of anything at all, and completely prepared to live the rest of my life alone. Now I have a beautiful woman who accepts me for who I am, and is the most important person in my life. I never could have imagined being lucky enough to find not only the perfect person for me, but someone who sees me as being the perfect person for themselves as well. I feel truly lucky and will do everything I can not to mess this up.

I hope to write again soon, and look forward to spending many, many years with Jess.

Pleasant dreams,
Sissy Stephie

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Thank you for your letter Sissy Stephie. Isn't amazing when you have an honest conversation how other people, especially those that care about you, understand, sympathize and accept you for who you really are. I hope this will serve as a lesson for those readers still hiding in the shadow of fear.

Auntie Helga

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