Is there a way to get more sensitive (and for the first penetrative sex to not hurt)?

[Merv]

Hi!

A few months ago I came here to ask about masturbation. Now, I still haven't had my first orgasm yet, but it finally feels achievable with my new sex partner. However, I wonder if there's a way to make it easier.

For some context - I'm a 21-year-old woman who purposefully tried masturbation for the first time at 19 and had her first sexual experiences with someone else at 20. However, both of us were unexperienced and didn't really do much in the end - kissing, groping, massaging, using hands, stuff like that. I have never achieved an orgasm, the best I could get out of myself was heavy breathing, even though I was touching myself in different ways for quite a lot of time (which would later lead me to stressing out about it and feeling bad about myself, so obviously at that point it would go nowhere).

With my new sex partner, I've had oral sex for the first time and realized that it's more effective for me than fingering. For the first time in my life I actually started making noises and shivering/making uncontrollable movements. However, my partner got eventually tired (it was pretty obvious to me that he tried to do it as long as he could) and after he stopped I started fingering myself while he was talking to me, but, unfortunately, the orgasm got away. He admitted that that was probably the longest he has ever given oral without breaks (it was like 15-20 minutes). And this leads to my question: is there a way in which I can highten my sensitivity to make it easier to come?

For some additional context, I've never had penetrative sex. It always hurts when I try to put a partner's penis inside, and I know that the whole thing with "the first time always hurts" is a myth, and I'd really prefer to not go down the "it hurts as hell for one or two times and then it doesn't!" route. Thank you very much, I'd prefer to find a way for it to not hurt from the beginning. Fortunately, both my ex-boyfriend and my current sexual partner have never pushed me too hard and comforted me when I was getting stressed out while trying to put it in, saying I don't have to apologize, but I'm frustrated with it almost as much as with not reaching orgasm lol.

So yeah, I'm pretty comfortable with my current partner, but want to find a way for me to finally come (and I guess not needing so much stimulation to feel something more would help) and to have a penetrative sex that doesn't hurt. My partner suggested to try next time during my time of the cycle when the vulva self-lubricates more + with some bought lube.

[Sofi]

Hi Merv! I'm glad your current partner is respectful of your boundaries, it sounds like he cares about you and that's important. I hear you want to orgasm and it's causing some stress, for lack of a better word. As you mentioned, when we're overthinking things it's harder to orgasm or even enjoy masturbation. The first advice is always try to relax and just go into it for your pleasure and intimacy/bonding with your partner, rather than with the goal of orgasm. That adds pressure to the situation and ends up making it harder to get there, so usually when we remove that expectation it can be easier.

Another thing you could try is toys like a vibrator, as you mentioned wanting to increase clitoral sensitivity. Many couples incorporate toys into sex because realistically humans cannot do the exact same thing a vibrating machine can, so it's an addition that makes the experience more enjoyable for a lot of folks. I'd suggest trying it on your own first, so you don't have any pressure at all regarding taking too long or anything like that. Once you figure out what you like, you can tell your partner and you can try it together. How does that sound?