I lost my virginity to a fuckboy frat boy about a month and a half ago. He was surprisingly very sweet in bed (despite being a major dick everywhere else) and really tended to my needs. He ate me out without me even having to ask and cuddled me afterward until I was ready to do more. After orgasming because of the head, I was exhausted and no longer very aroused. However, I was on a mission to lose my virginity that night and I trusted him so I wanted to seize the opportunity while I had it.

A little while later, I went down on him briefly and then it was time for the main event! He slipped on a condom, climbed on top of me (per my request), and put it in and GOD DID THAT SHIT HURT. My pussy was in so much pain from the pressure. I had expected there to be some pain that would eventually subside, but it was nothing like I ever could have imagined. He couldn’t even get it all the way in without hurting me so he stopped and took himself out. I was pretty wet so I wasn’t sure why it wasn’t working, so to speak. We tried a few more positions and some water-based lube, to no avail.

Eventually, he asked if it was okay to try “just going for it” and putting it in and seeing if the pain would eventually go away. We gave it a try, but with every thrust it just hurt more and although I pleaded for him to just keep going until the pain stopped, he saw that I was in a lot of pain and decided it was time to stop altogether. He drove me home whilst I unknowingly soaked my favorite panties with blood.

After the affair, I continued worrying about why I couldn’t just have sex like a normal person. I knew that rupturing the hymen would hurt, but the pain and pressure were unbearable. I considered seeing an OBGYN but due to other life complications I wasn’t able to get in to see one immediately following the encounter.

About a month after “losing my virginity”, I hooked up with the guy I have been in love with for many years in his brother’s tiny bathroom. I was so eager to finally do it with him that I bent myself over the bathroom sink and waited from him to slip in. He ended up getting only part of his dick in before the same incredible pain started up again. Embarrassed (and honestly very drunk), I shifted and suggested that I just sucked him off instead because of the less-than-ideal location of our tryst. He agreed, and it was my first time ever getting a guy off. Yay?

I am really struggling with my sexuality because of all of this. Is there something wrong with me? Why can’t a guy enter me without excruciating pain? Have I not broken the hymen enough? Am I still technically a virgin because I’ve never had complete intercourse?

Please feel free to give input and suggestions! I’m freaking out and I want to have this on lock before I have sex with another man.