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My first experience with a transsexual

Illustration by Eleanor Doughty. Matt didn't know it was possible for a girl to have a dick before the model pictured in his Hustler -esque mag drew seven inches. 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.
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What It’s Like to Have Sex for the First Time After Transitioning

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The Straight Men Who Have Sex with Trans Women - VICE

Instead, I want to point out that, contrary to popular belief, trans women do value singlehood just as much as the men attracted to us. Acknowledging that truth within myself has helped me better understand trans-attracted men. One would think this newfound knowledge would make it easier for me to pursue healthy sexual encounters with men. While a solid demographic of men appreciates my alpha nature, those same men have sometimes made things awkward. In these cases, I've resulted to blocking them, signing off and falling into an extended spell of sexual anorexia. So, here are a few tips to help cis-hetero men successfully navigate casual sex with trans women—so that all can benefit from the pleasures in waiting of mutual attraction.
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Just a boy: my first run-in with a transsexual

As we chat, Hammond shifts between these two conflicting narratives of post-bottom surgery sex. No matter how progressive your sexual politics, it can be difficult not to get swept up in the idea that our first experiences of intimacy are still significant. Of course, for transfeminine people, virginity narratives can be a bit more complex. Yet all those cultural ideas about sex as a woman — and first sex itself — still shape those initial forays into feminine sex, for better and for worse, in ways both exciting and awkward. No matter what your transition looks like, presenting as a woman can radically alter the way your partners treat you.
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My mother raised me to live a very vanilla lifestyle. We went to church each Sunday, had dinner at six o'clock, and I wasn't supposed to have sex until I was married. I was happy with that lifestyle because I was sheltered and had no idea that there was a world outside of Jesus.
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Your comments (5)

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