My first time dressing as a Sissy ~


These two pics were taken the first time I fully crossdressed and went out in public, I was 18-19 at the time. I had met with a girl online who was genderfluid herself after I posted an ad on craigslist asking for a girl to help me be more connected with femininity as I had never done it before. Surprisingly she replied and we talked for a bit before meeting up. She was extremely helpful and sweet, brining make up and talking to me and answering any questions I had. We went back to her house and she did my make up, dressed me in the clothes I wanted to try, which was goth lolita and we then went out ~ 

As we walked around we past some boys and she embarrassingly told me they were checking me out which made me blush and told me many times at how the boys we walked by were looking at me and liking me. She must have thought I was gay and I didn't deny at the time, I only blushed.
There was zero romantic or sexual attraction between us, I was just a girl-friend or a gay bestie to her.

Little did I realize how after this my addiction to dressing up and exposing myself would grow, how my masculinity startled to dwindle and fall, how my eagerness to out myself in public and feminize my body and mind would continue and turn into a never ending saga of me destroying whatever dignity or defences I had. I was a little sissy gayboi and I knew it. And soon everyone else would know it too...



This was one of two times I had met her. I'll post the next time in a future post ~




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