I'm 21 and I've never gotten an orgasm from vaginal penetration. Of course, everyone masturbates. I get orgasms from that every time I do the act of 'flicking the bean' but that's about it from what I've experienced so far.
I've only had two sexual partners, counting the current one I'm with and dated three guys in my life.
The first boyfriend I ever had, of course, didn't last long, it was only for three months. During that time, I didn't feel comfortable losing my virginity with him, but that doesn't mean we didn't do sinful things. We did everything but sex.
Moving on to boyfriend #2. It lasted somewhat longer, nine months, and the de-flowering process was great. It wasn't perfect... probably never is, but I was in a comfortable state of mind and I felt secure with the person. When it happened, it hurt... and felt like a literal 'pop'. There was some blood and he was sweet, trying to rub it off the hotel sheets we were just on. At this time in my life, I was 19. So yes, I didn't enjoy the act of sex, but I liked the idea of connecting with someone in such an intimate way.
Continuing our sexual intimacy, every time I had sex with him, it felt like he was just sticking it in and out...which is what you basically do right...? But I'm not sure, it didn't feel comfortable. Keep in mind, every penis comes in different shapes and sizes and the first time he dropped his pants I was legit intimidated by the size and length. I didn't exactly have multiple cobras to compare it to, just one. But to me, I was thinking if it was actually going to fit inside me.
So with time, it didn't feel that great. Maybe he was using it wrong...or not. But I wasn't getting any orgasm at all. He gave me oral and I'd get orgasms clitoral-wise, but never penetrating-wise. Eventually, I wasn't looking forward to sex at all and I really didn't like it. I had to concentrate and relax to get wet, (which I have no problem with) but it wasn't that enjoyable for me. So, he was mentally abusing and I left him for multiple reasons; mainly the abusing part.
So fast forward to 2018, I'm 21, and I get in contact with someone I used to know in high school. We connected and literally out of nowhere, we just kind of got into it and did it. I think the true reason I let myself go with him was the fact that I felt comfortable around him. I felt safe and wanted. I felt accepted and connected. I'm guessing that has a part in the feelings I've experienced with him. At first, the sex felt alright and I became nervous since I didn't enjoy sex from what I experienced in the past. But this person didn't have the same sized serpent, like what I knew. And to me personally, when it hits on your cervix, it makes me want to urinate and I feel completely uncomfortable. So this guy, he's able to get it to hit my cervix in certain positions of course, but he doesn't cause he knows what makes me uncomfortable or what feels like 'too much'. Communication helps a relationship more than you know. I know it's basic instincts to communicate, but sometimes it just doesn't come out.
I've been intimate with him since February 2018, and we're now coming at the end of June 2018. In four months of seeing each other almost every weekend, every time we have sex, and it just gets better. Still, I've never had a penetrating orgasm...or maybe I have but they were tiny faint ones. Not so sure. Yet just...every time we do it, it slightly feels better and better and I kind of get why people like it so much now!
I guess he just knows how to use it? Communication helps too, to understand what the other person likes. I mean now...the only way I can get an orgasm is if my 'bean' is active in it. Like the 'go-to' position for us would be from behind, but I'll be laying down, angle the hips upward and curving my back. So when he is inserting, he could slip it out and rub himself against me which feels great, and when he's inside me, I could also rub myself and I'll eventually get an orgasm that way. But so far...I haven't gotten a penetrating orgasm. Maybe, the more times you have sex, it becomes enjoyable? So with time, I'll eventually be able to get one.
Hopefully, if you're reading this and you haven't had an orgasm penetration-wise... I think it's normal. Your state of mind has to be comfortable. You also need to be completely into it and not get distracted by your surroundings. This is just some things I've heard of. Being attracted to the person helps as well. And I guess just letting go in the moment and feeling what the other person is doing, try to move with them, and foreplay has a huge part in it too.
If anyone has had similar experiences, I'd be curious to know. I like knowing about other people and I'm open-minded so don't hesitate to say something weird.