So I (20 MTF) use toys and I don’t have a problem with those. They just go right in. I had sex with a guy in the past and it felt like a hard pinch at first but then it felt really good during the rest. I am currently in a relationship and my partner (18 M) and I tried penetrative sex for the first time, but it didn’t go exactly the way as I planned it. We used plenty of lube and I fingered myself a bit before he entered. But when he got it in, it felt incredibly painful. I don’t know why this time it would be painful unlike my other experiences. I was dumbfounded. I was on all fours and I’ve heard that is not the best position for anal. However, the foreplay we have is incredibly hot. Why would I all of a sudden experience pain during anal when I haven’t before in the past?

2 comments
  1. There are several possibilities. But, importantly, where is the pain? Immediately around your anus? Deep inside while he’s in?

    Does the pain intermittently leave and come back? Is he longer or more girthy than anything you’ve had before? Have you had anything this large inside you in that position before?

    In order to diagnose the issue we need to analyze as many variables as we can.

    Most likely you’ll be able to make a small adjustment and enjoy the experience, but first we need to isolate and address the issue…

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