I guess this post warrants a trigger warning, as I get a touch explicit. I've been seeing this girl for a number of dates and they have progressed really nicely. I met her through CMB, and we've had great, fluid, candid conversations every time we've met. On our fourth date, a week ago, we went to a park, and laid down on a blanket and shared some kisses. It was really nice. For this date (this past Friday) I invited her over to my house to make a meal together. We were alone, so we had the privacy that we hadn't had before. The food came out great. Great, fluid conversation as usual. For all of my dates with her, there was no nervousness beforehand, just pure excitement to see her. I like her. At the end of the meal, we're drinking mead, and the conversation winds down. We both know where this is going, so she asks, "are you going to show me your room now?" I say, "yes". In my room we talk some more and then we start kissing. There's the best part, the excitement for what's about to happen. We're on our bed. I take off my shirt, and she giggles. We're caressing each other. This continues for a few minutes. She's not initiating taking off her clothes or anything like that so I ask consent (PS EVERY MALE SHOULD ALWAYS FUCKING ASK FOR CONSENT). I simply stop kissing her, make eye contact, and lightly say, "Hey are you comfortable with this?" I was expecting her to say yes, and continue kissing, but she didn't respond. I pulled back and asked again, "Hey are you comfortable with this? I'm all about consent, I'm not going to do anything you don't want to do." And she got a bit shy, looked away, and then said, "let's just not have sex." I'm a bit disappointed, but I'm kind of just really happy to hold her, that I let it pass. We escalate a few times, a little bit of dry humping, nothing more, and just end up conversing while cuddling for a majority of the night. While talking, she shares with me that she doesn't really get pleasure from sex. And she often finds herself just wanting the guy to just cum already. In my ego, I have the thought, "oh that will change. I'm going to give a ton of oral, and it'll be great." But we don't have sex. We talked for 3-4 hours, and then we went to sleep. We woke up 4 hours later and continued the same thing. A few hours later, she somewhat surprisingly (out-of-the-blue) says, "Ok, you want to have sex?" I calmly respond, "yes." lol We escalate, take off clothes. She won't let me give her oral b/c she was self-conscious (not that I would have cared....). Now in my past experiences, the first few thrusts are a bit dry, but then the vagina lubricates itself and then that's when a good rhythm is established. In this case, her vagina never lubricated. We even used lube (but probably not excessively enough). We never got into a rhythm. I could tell she wasn't enjoying it, with the exception of a few brief seconds. So, remembering what she said, I tried to cum as quickly as possible. Now I feel like I'm using her and I'm too performance oriented, which I didn't like. She could sense my stress to cum and my uncomfortabless. She kept trying to convince me that she liked it by saying, "I like the intimacy" and I felt like she was just saying that to make me comfortable. I felt that was her way of saying, "I don't really like it." In hindsight, I think she was just saying the truth. Just a side: this has nothing to do with PIED. I've never had that. So, I didn't cum, and we had a really tense moment where we didn't know what to make of it. I was thinking, fuck that was somewhat disappointing, and she's thinking, "oh no, he didn't like it." The sex just ruined this great thing we had. Her eyes watered in sadness and I didn't know what to do. I didn't want her to be sad, but I didn't want to lie. She even asked if I wanted her to leave, and I say, "what? no way!" But it still feels awkward. I try to get her to feel more comfortable by telling her I really like her. It helps a bit, but still. Eventually she compares sex for her to be like me giving oral. I enjoy giving oral, but it doesn't give me any physical pleasure, just mental. Sex for her is the same. She doesn't derive much pleasure from it, but she enjoys the intimacy. With this mindset, she asked if I wanted to try again. Not having cum yet, I said, sure. I enjoyed it more. I wasn't trying to cum. But after a short while, she asked to stop, because she wasn't enjoying it. Still never cummed =/ And that was that. We stayed in bed until 11. I made her breakfast, and then she left. And when she left, I felt this profound sadness. Hit me like a train. Boom. Super lonely. Sad. Don't know what to do with myself. And it took a while (essentially until today) to process what happened. Why was I sad? I think what happened is I made an assumption: I assumed the sex would always be disappointing. That's totally not true. There's a bunch of things I can do. We can try lube more liberally. Also, I generally try to masturbate the day before or morning of, when I know I'm going to have sex. In this case, I can try going several days without. As a Fapstraunaut, this should not be an issue at all (I'm not refraining from MO these days, but I've had a 150 day hard mode streak before). I had been masturbating about 5-6 times a week, looking to cut down to 1-3 times. Now I have a reason to! Also, we were together in bed for 13 hours and we only slept 4 of those hours. That's an absurd amount of time to be with someone. I was aware of it in the moment, but I figured, "This is our first time" we can be reckless with the time. But going forward, I think I will avoid that. It was too much and it fucked with my emotions. I felt such a loss when she left and that was a consequence from being with her intimately (cuddling) for such a long continuous time. We've been texting a lot since, we have a date this Friday, and I'm stoked about it. I'm going to ask to make our relationship official. And it should be great! Just wanted to share that story with my fellow fapstraunauts to help me process. In writing it, I think I did process it. TLDR; I have sex on the 5th date, it's somewhat disappointing. But instead of assuming it will always be like that, I remember why I like her and I'm looking forward to seeing her this Friday.