First time sex with a transexual

We are in his room. And… I am in his room. I have butterflies like I never had on stage. I have a fair amount of alcohol on-board, not out of control, enough to take the edge off the fear. He looks gently expectant. We both stand awkwardly for a minute, then he reaches tentatively, with an inquiring look, undoes the top button of my blouse.
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Seventeen: Sex and the Trans Girl

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A Straight Guy's Guide to Sex With a Transgender Woman

My First Time is a column and podcast series exploring sexuality, gender, and kink with the wide-eyed curiosity of a virgin. We all know your "first time" is about a lot more than just popping your cherry. From experimenting with kink to just trying something new and wild, everyone experiences thousands of first times in the bedroom—that's how sex stays fun, right? This episode, we're speaking to Nail Transphobia campaigner and author Charlie Craggs about having sex after coming out as transgender—and her shock at how badly straight men treat women. After a while, he suggested meeting up.
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My Second First Time: What It's Like to Have Sex After Transitioning

She had slipped in unannounced between the magazine's other, more typical spreads. His stroke quickened, sticking with sweat in his Brooklyn bedroom while a worrying thought knocked in his skull : Did it mean he was gay? I met Matt in his home, thirty years after that fateful day in his teenage bedroom. His name has been changed to maintain anonymity. We sat on opposite ends of an ultra suede sofa, he in a pair of basketball shorts and a white t-shirt.
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For most cisgender straight people, the first time they have sex makes a relative degree of sense to them. They identify with the gender they were assigned, so sex feels mostly natural and comfortable. For transgender or genderqueer people, however, this comfort is often lacking in their first sexual experiences. Thankfully, having sex after they begin their transition can be a completely different experience. It's almost like losing your virginity for a second time.
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