My girlfriend (30f) of about 5 years can’t seem to cum and I (30m) don’t know what to do. /u/ProblemMan Sex

So long story short, I’ve been with my girlfriend about 5 years. We actually also dated in high school and took each others’ virginity and were most of each others’ firsts for everything.

In the five years of our adult relationship I may have never made her cum. I say may have because she seems very confused on the matter usually saying she’s “not sure” if she’s had an orgasm, which for me is a pretty clear sign that she hasn’t.

She says in her last relationship of about 8 years that the sex wasn’t good but she maybe came once near the breakup. If she’s ever had one, it might have been years ago when we spent a night together in high school when at the time we really thought we did it with my fingers. I can say that my interpretation at the time was that she definitely came but these days she tends to say she isn’t 100% sure that’s what happened.

She does masturbate occasionally typically with a vibrator and while she does enjoy it, she hasn’t managed to have an orgasm. We’ve got a few different types including a vibrating dildo, a smaller one, and a sonic / clit sucking type. She has never achieved an orgasm on her own, she’s sure of that.

When we’re intimate I often will rub her until my arm is ready to fall off and my finger is completely wrinkly from moisture. I honestly love eating her out and will do it basically indefinitely if it’s working, but usually she says it’s nice but isn’t building towards an orgasm. Typically after a while she’ll want me inside of her and I’ll keep touching her clit or we’ll use a vibrator.

Sometimes the vibrator seems really effective and it gets to the point that her vagina is squeezing my dick so hard I’m slightly worried it’ll be damaged but she never quite seems to get over the edge and orgasm.

We’ve tried all sorts of things, I’ve spent hours reading online, I’ve also tried not trying and just not focusing on it so much during sex. Nothing seems effective, I’m not sure we’ve made barely any progress.

What else can we learn or try to break through this block and enjoy many and easy orgasms together?

I’ve had a couple of random hookups but she’s really the only woman I’ve ever had an ongoing sexual relationship with so I’ve never made someone I was with have an orgasm. I love her but I’m starting to feel really sad because cumming with someone is something I really really want to experience and it feels like I’ll never get to as long as I’m with my current partner.

So long story short, I’ve been with my girlfriend about 5 years. We actually also dated in high school and took each others’ virginity and were most of each others’ firsts for everything.

In the five years of our adult relationship I may have never made her cum. I say may have because she seems very confused on the matter usually saying she’s “not sure” if she’s had an orgasm, which for me is a pretty clear sign that she hasn’t.

She says in her last relationship of about 8 years that the sex wasn’t good but she maybe came once near the breakup. If she’s ever had one, it might have been years ago when we spent a night together in high school when at the time we really thought we did it with my fingers. I can say that my interpretation at the time was that she definitely came but these days she tends to say she isn’t 100% sure that’s what happened.

She does masturbate occasionally typically with a vibrator and while she does enjoy it, she hasn’t managed to have an orgasm. We’ve got a few different types including a vibrating dildo, a smaller one, and a sonic / clit sucking type. She has never achieved an orgasm on her own, she’s sure of that.

When we’re intimate I often will rub her until my arm is ready to fall off and my finger is completely wrinkly from moisture. I honestly love eating her out and will do it basically indefinitely if it’s working, but usually she says it’s nice but isn’t building towards an orgasm. Typically after a while she’ll want me inside of her and I’ll keep touching her clit or we’ll use a vibrator.

Sometimes the vibrator seems really effective and it gets to the point that her vagina is squeezing my dick so hard I’m slightly worried it’ll be damaged but she never quite seems to get over the edge and orgasm.

We’ve tried all sorts of things, I’ve spent hours reading online, I’ve also tried not trying and just not focusing on it so much during sex. Nothing seems effective, I’m not sure we’ve made barely any progress.

What else can we learn or try to break through this block and enjoy many and easy orgasms together?

I’ve had a couple of random hookups but she’s really the only woman I’ve ever had an ongoing sexual relationship with so I’ve never made someone I was with have an orgasm. I love her but I’m starting to feel really sad because cumming with someone is something I really really want to experience and it feels like I’ll never get to as long as I’m with my current partner.