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The walls of the rectum are thin, which means they tear more easily. Without proper preparation – like foreplay and lube – anal sex can be painful, causing tears that allow bacteria or viruses to more easily enter your bloodstream. There are a variety of butt plug training kits on the market that come with plugs ranging from small to larger sizes.

That FOMO you describe will be with you, regardless of which path you take, until you tackle where the FOMO is coming from itself. The transparency you want to proceed with requires introspection on your end about these subjects. From there, it might take some time (or it might happen on your first date) to find someone who is as open to discussing the details of sex and dating desires as you are. Safer dating guidelines include letting a trusted friend know where you are, who you’re with, and when to expect to hear from you. If you go to their home or a hotel, let your trusted friend know about the change in location and keep track of where your belongings are in case you need to grab your purse and shoes and exit quickly. There are dating sites and apps that attract people who are looking for, or even simply open to, the kind of casual sex you say you’re looking for.

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