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Crossdressing during sex encounters
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Just wondering if others on here have had crossdressing experiences prior to their transition? And any thoughts on crossdressing during sexual encounters and its relation to transition. I live as an effeminate male.

I have been crossdressing since 2017 during sexual encounters only. Often times in the past I would fully crossdress to include wigs, makeup, outfit. After a while I would find that people I engaged with in these sexual encounters were interested in the identity I had created crossdressing. After developing ongoing sexual relationships with people through crossdressing it often leaves me confused about what my true identity is. I also have resented crossdressing because I felt it was a false portrayal of my reality as a cisgender male. But still to this day, I do often crossdress during sexual encounters - if not fully, partially with an outfit.

I have started to discuss and tackle this with my therapist but this is an ongoing conversation I am having with her. I know in terms of gender identity I am somewhere on the spectrum. Currently I do normally wear makeup, mostly minimal to cover imperfections and enhance features. But I am more inclined now to delve into more androgynous clothing options and even grow my hair.

I know I should freely express myself however I want, but it has been a challenge and have a fear of judgment by others.

Any help and tips are appreciated. This is more of a rant on my part. Thanks in advanced for any help and hopefully this post is not offensive to anyone. That is not my intention. Thanks!

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10 months ago