TL;DR: I’m 25F, the guy 27M I’m seeing is a virgin and we’re planning to have his first PIV in about 3 weeks. He hopes for condomless PIV (I’ll be on the pill) for his first time, but I’m more worried about pressure, expectations, and the fact that my past virgin partners sometimes struggled to finish, especially if they had specific masturbation habits. Looking for advice on how to make his first time comfortable and low-pressure, and how to handle it if he can’t orgasm from PIV.
I’m 25F, the guy 27M I’m seeing is virgin and has never had any sexual experience with a partner before. I’m not a virgin and have had a few relationships, but this is my first time date a guy older than me. We’ve been dating for about two months, get along really well emotionally, so I plan to live with him for a short period of time, maybe about a week, after I finish dealing with recent personal things.
He has mentioned that he really hopes his first time can be condomless PIV. I’m not completely against that if we do it safely, so my current plan is to start taking birth control pills with my next period. By the time we actually have sex it’ll be around 20 days from now, and I’ll likely have another period in between. I know I should follow the usual guidelines about taking the pill correctly, so I’m looking for advice here, more like: is this timing and idea reasonable, and what kind of conversations / boundaries should we set around “no condom for the first time” (of course with STI testing etc.)?
Another thing I’m slightly worried about is his ability to finish with PIV. My personal experience with other virgin male partners has actually been the opposite stereotype: they sometimes struggled to finish during their first PIV encounters, instead of “finishing too fast”. He’s also the oldest guy I’ve dated so far, and from our conversations it sounds like he masturbates quite regularly. I’ve had one ex who had a lot of trouble finishing during PIV because of long-term “rough” or very specific masturbation habits. I’m a little worried this might happen again, not in a judgmental way, more like I want to be prepared and supportive, and not make him feel like he’s “failing” if he can’t orgasm from penetration.
So I’d love to hear from people who have either been the virgin guy in this situation or the more experienced partner with a virgin man:
What helped make the first time feel good and not overly pressured for him?
How can I talk about expectations (like “it’s okay if you don’t finish” or “we can stop anytime”) without making it awkward?
If he does have trouble orgasming during PIV,, is there anything I should not say or do that might make him feel worse? And what’s a healthy way to approach this early in the sexual relationship?
I'm currently in the throes of new love and seem to be losing my head a bit.
I've already refused condomless sex, I've told him I'll let him know if I change my mind ( though I'm still planning to start taking birth control pills).
Getting so invested in a relationship can easily make you forget your boundaries.🥺
Although it sounds very dramatic, I don't know why, but the guys I've dated seem to have a higher chance of not finishing during their first PIV. Their first time often lasts over 20 minutes. I don't know if it's my problem or some strange coincidence.
I think it might be related to their poor masturbation habits. I've read some information that suggests excessive masturbation, gripping the hand too tightly, or frequent edging-style masturbation can cause delayed ejaculation or even an inability to ejaculate.
One of my exes had delayed ejaculation due to taking SSRI antidepressants. Although our sexual experience with him was good, I did experience minor abrasions a few times, seemingly due to the prolonged sex. (I didn't feel any pain during intercourse; I only noticed the abrasions when washing afterwards, not because I was enduring it during sex.)
Another former sexual partner of mine had an orgasmic disorder, which I believe was caused by poor masturbation habits. Now, two years later, he describes being able to ejaculate during intercourse only without a condom in specific positions, and it seems he has given up on intercourse.
I also had an ex with severe ADHD who would sometimes get distracted during sex, then end the act or return to the sex phase but start all over again, so the entire sex session would last about 30 minutes.
These dramatic coincidences, coupled with the fact that several of my exes said my vagina didn't seem tight enough to give them enough stimulation, made me very worried about partner ejaculation problems.
To be honest, I'm not worried about premature ejaculation because the second time usually doesn't end so quickly.
But ejaculatory dysfunction is a much more troublesome issue, sence it could cause problems like abrasions, and the frustration of being unable to ejaculate seems even harder to soothe.