Surprise entry in The day to day

Sigh. Dating is so hard. Why is it so hard? I met someone this past weekend and we spent it having sex, snuggling and just being together. He was great at making sure I got off everytime. He actually has a broken foot so he couldn’t do a lot of positions. This was our first time being together physically so I had never seen his penis. It was average which is not a problem by any means. But it never seemed to get as hard as any other penis I’ve ever seen before. It wasn’t that hard in my mouth or hand. And then when he tried to stick it in me. I couldn’t feel it. Like at all. I never said anything during the course of the weekend.

But he was just messaging me and mentioning being ready to see me again the next weekend I’m free. He discussed how nice and snug his penis was inside me. He said he loved when I tightened down on it and it made him pound me harder. I couldn’t even respond for the longest. We had previously discussed how sex is an important part of a relationship as well as communication.

I had to tell him all the things that I loved that he did to me this weekend, but then break the news that I just couldn’t feel him inside me. I also told him that it seemed to take a lot to get him off so I wasn’t sure I was satisfying him. He didn’t catch on at first to the not feeling him thing. I basically had to say it plainer and then he felt embarrassed. He said that I had felt him in my mouth and hands so I had to know he was hard. But that’s the thing. He wasn’t that hard. At least I’ve never had a soft hard cock before.

I’m not sure where to go from here. He’s very sweet and very in to me. He asked if I was turned off by him now. I told him no. In every other way he satisfied me. However, if I never get to feel him inside me then I don’t know that I would ever fully be satisfied.

For now we are going to continue to see each other. And maybe when his movement is not as limited it will be better.

Last updated December 06, 2023