Not able to cum

I consider myself straight. I was with a transgender woman for almost 15 years and I wasn’t able to cum the first couple of times with her. Our relationship was heteronormative in every sense. Sex involved me inserting into her. She did not have sexual re-assignment surgery so you can pretty much put two and two together as to where I was inserting into her. I left her and filed for divorce due to a drug problem she developed. The last 3 years of our marriage there was no relationship and the sex was more of a business transaction but I was able to cum. The sex stopped a year ago.

I developed feelings for a cisgender (biological) woman at my job a few months before leaving my wife and moving out. I found a different job elsewhere and we started seeing each other after I left that job a couple of months ago. She knows about the divorce and even met my ex-wife once but didn’t know at that time she was transgender. I wasn’t able to cum with her when we had sex for the first time a month ago and I explained that I’m never able to the first time with someone. She found out a few days ago my ex is transgender and I was truthful about everything. She doesn’t really understand transgender and asked me if I’m gay. She also expressed concerns that maybe I couldn’t cum with her because she isn’t transgender. It really hurt having to sort of defend my orientation. I explained to her that this was my past, I moved on a while ago, she’s not a rebound or a trial. It’s been years since I’ve been with a woman that has a vagina and I feel almost like I have to prove myself, which adds more pressure.

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From her point of view you had sex with a biological man. Her concerns are warranted. How did the woman you’re seeing find out your ex is transgender? If you lied to her/actively hid it, your shame is your issue to address and should not be put on the woman you’re seeing. If you’re confident in your sexuality, why are you so offended? Having to explain sexual history is a normal part of any relationship. If she is bothered by your being bisexual, the that’s her issue to deal with.

Probably you got used to your penis having contact with an anus and now that it’s having contact with a vagina is a strange and like you said adds pressure that you have to perform to please your wife. Maybe seeing a penis besides yours got you in the mood to have sex or stimulated you and now that that is missing you don’t get as turned on as you used to. You shouldn’t have any guilt or get offended, cancel all that out from your head and keep it honest and respectable with your wife and keep trying different things.