Sorry in advance the post is a mess.
23M just had first hookup with some chick I met at the bar. I don’t think I’m ready to post the whole entire story but it kinda cracks me up just thinking about how it all started. Details are just too specific and I wouldn’t want this post blowing up or ending up on tiktok. Anyways she invited me over to her house a couple days after we met. We started making out and losing our clothes. I felt like it was very obvious that I wasn’t very experienced, but I couldn’t tell if she was either because I don’t know how these things usually go. I don’t know why but I literally could not get it in. The positions we were in weren’t super optimal for me to see and no space for me to help my unit in. She obviously knew I was struggling to get it in (I just straight up told her) and so she tried to guide me in herself. She couldn’t get it either. So she just continued to grind on my dick. Which I didn’t mind. We went at it on and off for 3 hours. We did more kissing than anything. At one point I began to finger her under the covers, it was here that I realized just how tight and sensitive she was. My finger barely fit in and I would only get it halfway in before it sounded like it might’ve been hurting her. I tried to be as gentle as I could from there on and just sorta let her take the lead. I really didn’t want to hurt her or do anything she wasn’t comfortable with. She switched between grinding on my dick to making out to sucking my dick. I didn’t cum once the entire night. I got close a few times but every time she would stop and begin something else. Despite not cumming I honestly had great time, she apologized but didn’t say what for(I assume because I didn’t cum.) It didn’t really matter to me though, I really like this girl and I think she likes me. I just don’t know what I’m doing. I also don’t know if she knows what she is doing. She wants to see me again which is a good sign I think.
I really don’t know what I am hoping to find by posting this. I will post updates if this post gets a lot of attention maybe I will post the whole story in the future because it’s pretty funny and awkward from my pov (think Michael Cera awkward.) Any advice or questions are welcome.