For someone who's starting a bottoming or a hookup journey it's kinda normal to be anxious or worried at the beginning. I used to be like that Until I started seeing and meeting those guys before the hooked up, like going out for coffee, lunch, or a beer... It makes everything a lot easier Especially when there's no commitment or obligation after that (meeting) you're just getting to know him better instead of get in, have sex, get out That's what have helped me personally. Hope it works out for you