I posted this to the sex over 30 sub but they suggested I post here.

I’d love to get opinions on this as I’m not the most confident and tend to be a pushover when it comes to dating/sex. I also haven’t had many sexual partners so I’m also inexperienced in that regard.
I’ve been dating a 42/M for two months, things have been going well. Yesterday we had a date that was somewhat of a disaster.

First time we had sex a few weeks ago was mostly great, aside from me having to ask him to put a condom on twice. He suggested pulling out, I insisted on a condom. I can’t orgasm from PIV sex and he knew this… he didn’t attempt to get me off. He orgasmed and that was that. Some convo after the deed resulting in me suggesting he could do me first next time, and he replied “oh now you tell me!” He also didn’t think I could orgasm from sex. Explained to him I can easily with some manual help. Chalked up this experience to a new sexual partner misunderstanding, no big deal.

Which brings us to last night. Tiny bit of foreplay and he’s already unbuckling his pants for me to give him a BJ. I oblige for a bit, assuming he’d do me after. We go to the bedroom. He fingers me for a whole 30 seconds and goes down on me for about 15 seconds. Positions himself for PIV. I have to tell him to get a condom, again. He asks if he can pull out again. I tell him no.

At this point I’m already feeling like this is going to be a somewhat shitty experience for me, and I was right. We have PIV for a bit and it’s fun enough for me, but he can’t orgasm and blames it on the condom. We eventually get dressed and call it a night.

The entire thing was just really awkward. I told him I felt badly he couldn’t cum, he claimed it wasn’t my fault- blamed it on the condom, and that he had been drinking. I left shortly after that.

I’ve been replaying this whole thing in my head all day and I don’t know how I feel about it. I’m actually kind of shocked he didn’t even try to get me off- and all the condom weirdness makes me a bit uncomfortable too. He knows I’m not on birth control (he’s my first sexual partner in 5 years.) We haven’t had the STD talk/tests.

Ironically, he has a 14 year old son who was the result of a surprise pregnancy… he married the mother not because he wanted to, but because he felt like he had to because she was pregnant. They had an awful marriage and were divorced after 10 years. I kind of felt like saying… dude have you learned nothing from that experience?

We haven’t spoken since and I’m really wondering whether I want to continue things. I’m definitely not opposed to getting on birth control if we ever became exclusive, and we should both also get tested for me to feel comfortable forgoing condoms.

I just don’t know. Is this something communication can fix? Am I making too big a deal out of nothing?

He hasn’t had many sexual partners after his ex wife, so all I can summize is he got so used to fucking one person for so long that he doesn’t know wtf to do with someone new.

TIA for any insight.

25 comments
  1. Why would you think repeating what you already told him will matter when he didn’t “know” (care) enough to ensure you’re enjoying it as much as he? Selfish lover is just the beginning. I would not have even given him chance #2, much less 3. We’re old enough to know that other people matter

  2. Wow. Yeah. No disrespect but I know dudes who treat legit sex workers with more care and concern than your bf is doing for you.

    He’s 42, and likely set in his ways. He’s likely not going to change. If this isnt a dealbreaker for you go for it, but with this level of casual disrespect be ready for it to bleed into other aspects of your relationship once the honeymoon phase dies.

  3. I didn’t even read half of this but this is a NOPE. NOPE him out of your life forever. Please.

  4. I would dump this guy, he only cares about himself. Also, you don’t negotiate the condom. He’s going to keep pressing the issue and you will still be unsatisfied. He doesn’t care about you.

  5. I don’t think any amount of communication is going to turn him in to a person that enjoys making his partner feel good.

    If he really hasn’t been with someone besides his ex in so long, I would expect he’d be dying to explore a new woman’s body!

    Instead he’s blaming you for “not telling him” that he should care about your pleasure.

    Even if he was amazing in bed, the fact that he keeps pressuring you for no condom is an instant deal breaker.

    He doesn’t care about your pleasure and he thinks it’s OK to nag someone for something (totally reasonable) that they’re not OK with.

    He’s an ass.

  6. >Ironically, he has a 14 year old son who was the result of a surprise pregnancy… he married the mother not because he wanted to, but because he felt like he had to because she was pregnant. They had an awful marriage and were divorced after 10 years. I kind of felt like saying… dude have you learned nothing from that experience?

    This guy can’t even learn from cause and effect in his own damn life. It’s no surprise he hasn’t learned from your previous attempt to communicate with him.

    >He hasn’t had many sexual partners after his ex wife, so all I can summize is he got so used to fucking one person for so long that he doesn’t know wtf to do with someone new.

    I’ve been with guys with limited sexual histories who were wonderfully responsive and attentive lovers. I think this guy is just a dud.

  7. I think you’re being too generous in saying he “doesn’t know what to do with someone new,” like you specifically told him that you like manual stimulation. He just doesn’t care about pleasing you. It’s also alarming to me that he is pushing back about condoms, if he cared about your health (and his own!) he would insist on using them and you wouldn’t even have to ask. He is acting this way because he doesn’t care, not because he doesn’t know any better.

  8. You already lost me at –

    > me having to ask him to put a condom on twice. He suggested pulling out

    Throw the entire man in the trash. We are too old for this shit.

  9. Did we date the same guy??? I’m joking, of course, but I had a similar experience with a guy a bit over a year ago.
     

    He honestly sounds like a dick and you’re not ever going to have your (sexual) needs met by this guy. You told him what you would like him to do and he did the bare minimum.
     

    Dump him. You can do so much better.

  10. The condom reluctance the first time alone would be enough for me to call it. He prioritizes his pleasure over yours or his own well-being. Bad judgment and bad character

  11. Rules #2 : take control of your sex life…. Don’t bend the knee for him until he goes down there to salute on you

  12. They’re not going to change, no. He’s 10 years older than you and still doesn’t understand how good sex with a woman works and doesn’t revolve around himself

    Find someone who is more worthwhile. They’re selfishness in the bedroom will likely show up in other places

  13. Girl run. He doesn’t respect your boundaries for a fricken condom? He’s going to take the first chance he can to have sex with you without it, like if y’all are drunk. Makes me think he probably does this often. When was he last tested? my guess is not recently. That alone would be enough to make me end it with someone like this.

  14. The fact that the issue with the condom came up a second time is enough for me to think he’s selfish and doesn’t respect boundaries. He won’t change.

  15. 1. Condom use should be nonnegotiable. Obviously.
    2. You apologized for not making him cum when he failed to make you cum TWICE?!

    This man sounds like a trainwreck. Also, OP, consider getting birth control. If you’re against hormonal birth control there are copper IUDs or diaphragms. (Yes, it feels 1950sish, but they do still exist).

    All it takes is one guy to stealth and you’re looking at consequences, not to mention breaking/slipping off (happened to me with a smaller partner).

    Hope you find a great partner sometime soon!

  16. Girl just run and don’t look back. And If I were you I’d tell him the truth that I’m ending things because you and him are not sexually compatible. That both sexual experiences with him felt so selfish from his part and you didn’t enjoy it.

  17. It’s amazing to me how many men think that their penis is more than enough to get a woman to orgasm when so many of them don’t even know how to use it. Or that 15 seconds of foreplay is enough to get us off or even turned on to the point of actually being wet wnough to accommodate sex at all. I wouldn’t say I’ve had a lot of lovers but I’ve been with my fair share and of these only 2 actually managed to bring me to orgasm during foreplay before they got off and only one before intercourse at all. Even if you do explain and instruct it’s as if it falls on deaf ears and they are only interested in their pleasure. The selfish liver thing in a man is unfortunately quite common. The condom thing however is a level of disrespect that I would not tolerate. It shows he doesn’t care about you in the sense that he may have a std nor does he care if he gets you pregnant. That to me screams disrespect and if he’s willing to disregard you in this way he will do so in many many others. Ditch him girl. Do yourself a huge favor and avoid the future of misery with this selfish ass

  18. I made up a rule for awhile that I wouldn’t blow a guy until he gave me head first. Do you know HOW MANY fucking men will ask for BJs and then just NOT return the favor? Like WTF, man! I really chalk this up to the fact that so much of sex is based around the man cumming. How many times you have sex with a man in one night, is based off how many times HE cums. The END of sex, is when HE cums. The quality of sex is big time based off if HE cums. I’m so fucking sick of the bullshit. You can give me head or you can GTFO.

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