I feel like I’m totally broken sexually. I’m deeply in love with a woman who deeply loves me, too, but I can’t orgasm at all when I’m with her.

I’m a guy who just turned 60. I enjoy excellent health, I have high testosterone, and look and feel a lot younger. She’s 44, every straight guy’s fantasy, and guys by the score, young, old and in between, are hot for her. Every aspect of her personality and body excites my emotions and turns me on. She’s gorgeous and the perkiest ass and boobs you can imagine. She’s deeply loving, as sweet and sincere as can be, and totally sexy. She quickly makes me hard, and there’s nothing that I love more than fucking her just the way she loves to be fucked. She wants badly for me to come inside her, in her mouth, on her face and boobs, and on her back. But I can’t come inside her or on her. I can’t come when she blows me or jerks me off, either. And I can’t come with her while jerking myself off.

We started seeing each other two years ago. Then, and for a few months after, my not being able to come was bad, but it wasn’t this bad. She would volunteer to jerk me off and eventually I’d come, even if it took 30 minutes to an hour, and it would be the most amazing orgasm I’d ever had. Then, just as I felt I was healing and it was taking take me less time, she got triggered over the whole thing and broke up with me. She still visited me and had sex with me once in a while, but I never again orgasmed with her. After eight months, we got back together again, and again she got triggered over my dysfunction and broke up with me. This has happened a few times. Love keeps bringing us back together, and yet I can never come when with her, and it keeps causing so much heartache, depression, and distress between us.

How I got to this point feels like the worst sexual misfortune a guy could suffer. Due to general sexual repression aided by my own personal sexual repression, I was a virgin until I was 30. My deflowering sucked big time. After that, I went through decades of very little sex and no lasting romantic relationships. Even though I’m a tall, handsome guy, my naivety, inexperience, and eagerness waved a red flag to all women of interest to me. On top of that, despite lots of effort on my part, online and off, and despite various infatuations, I never met any woman who I could relate to and love like I do this woman.

All this lack of sex, starting from my teens, led me to first Playboy, then Penthouse, then pussy mags, then hardcore porn of all stripes as the Internet evolved, to grant myself at least some visual exposure to what my life kept denying me — always leaving me disgusted with myself and porn.

I had this problem before with other women, but with most eventually I’d come. I went through a period of going to sex workers and bodyworkers, and I would eventually come from their touch. But it was always a huge challenge. At last, five months before I met my girlfriend, I completely stopped watching porn and stopped jerking off, too. Three months into this discipline, I went to a sex worker who wasn’t even very attractive to me, and I came almost immediately when she sucked and jerked me. I went to another sex worker and was able to come with her, too. I thought I was at last healed. That last encounter happened only a few weeks before I met my girlfriend.

Life had taken her on a totally opposite path. She was highly sexual before met and was also, sadly, sexually abused over many years as a child. Suffice it to say that she suffers greatly to this day, even though she is working on her trauma with a therapist I found for her.

A lot of the reason I have for not being able to relax and come when with her is my not feeling as secure as I could in our relationship. From time to time she still breaks up with me very dramatically, for no reason other than that the love freaks her out — we never argue or have conflicts. She just panics and gets nauseous, as if I’m going to entrap her. Also, she still maintains connections with a few people in the poly community that she had turned to when she had broken up with me. And that has me fearing she’ll act out with other guys, like she did in that period.

But my issue is due more to me having watched so much porn while jerking off in my past decades of loneliness, my brain has changed to where nothing in person excites me enough to take me over the top. Ironically, my girlfriend did a few porn non-hardcore porn videos long ago with a man who made her come using his hands. She told me about them and I managed to find them on the Internet and now I can’t look at any other porn now without feeling sick. She still looks pretty much the same. And it’s not like I don’t get her excited or can't make her come. She is multi-orgasmic with me. I’ve never seen any woman get so deeply absorbed in the sexual experience and to orgasm so intensely as she does in these videos. I have wondered what that’s all about, and I can jerk off to one of those videos in particular multiple times a day and come intensely, knowing her as well as I do and imagining what she was experiencing. I did that in the period when I wasn’t seeing her and she was seeing another guy and I was hurting terribly.

I don’t do that now, and I try not to masturbate at all between times when I see her, but I realize a few things about that. First, what gets me off is her getting off, but obviously even though she comes when I’m fucking her (she’s not faking it), vaginal intercourse is never enough stimulation for me. She’s only let me do her in the ass a couple times very briefly, because, even though it’s hot for her, she has a fear of feces. And I don’t really know if the extra stimulation would even help and I sincerely doubt it.

She likes to play with my cock and knows just how to get me totally hard before we have sex, but jerking me off from the get-go, even though she initiates it, is a duty to her, which triggers her after not short time. (It reminds her of one of her abusers.) She’s also never confident about what’s she’s doing, despite my showing her what works for me when I jerk myself off. After all the hot fucking, an endless hand job quickly becomes tedious and I even start getting soft. Her rubbing my circumcised cock head, where it’s the most sensitive, feels amazing but also makes my dick retract and soften. So that activity just adds to my performance anxiety while leaving her feeling ineffectual.

I’ve tried to get her to 69 with me, which is a big turn on for me, but she says it distracts her. I’ve asked her several times to get between my legs while I’m on my back and blow and jerk me, which would also be a big turn on, but she refuses. It seems she just want me to eat her and fuck her and come and make her come, or for me to come easy from being sucked a little, and be done with it.

Second, when on my own, I seem to have had the most intense orgasms when I was emotionally hurt and rejected, jerking off to her videos (or in the past, other porn). Third, the idea of her being stimulated by other guys and watched turns me on. She has told me that being watched turns her on and that, once, when I was fucking her, she was fantasizing about us being watched. She has had such experiences before and I have fantasized about that and it turns me on. It also turns me on to think about her being with me and another guy.

In reality, though, neither of us want to go there in our relationship, at least not for a long while. I’m not at all poly, I doubt I could share her, and having known a lot of people in the poly world for decades, I am totally turned off by the whole culture and wouldn’t want to open that door. More to the point, watching a video of her turned on is what immediately gets me aroused and coming hard, from a distance and alone, and not while being watched myself, so I'm not sure I would actually enjoy realizing these fantasies.

When she is jerking me I try to visualize things that do turn me on but it’s impossible. On top of that, there seems to be this horrible karma of tons of distractions popping up, no matter how much I try to set the scene so that there won’t be, and despite there being no distractions when I’m pleasuring her to orgasm.

Even when I’m alone and jerking off, it can take me a long time, now that that I don’t turn to the visual stimulation of porn or even just nude pictures I have taken of her. Not masturbating at all when I’m not with her, so that she is my sole source of stimulation, seems to decrease my libido, and she’s so unpredictable with her freak-outs I never know when I’m going to see her next, so that I can’t let myself submit to the anticipation.

So it’s been over a year now since she’s seen me come. The last time that we were together after she jerked me and I didn’t come, she curled into a ball and punched the bed.

The most important thing I have learned from being with her is that I need to totally love a woman and feel loved by her to get excited enough to even get hard and fuck. When I fuck her I’m telling her how not only how hot she is, but how much I love her, and that gets her off like crazy. And what was so amazing about coming from her touch was feeling so much love for her, and becoming totally vulnerable to her. I ache for that again so much that it is perhaps the biggest obstacle to me not coming now when I start getting close.

The one thing we haven’t tried, even though we’ve talked about it, is me just jerking off with her next to me and relaxing, and she takes over when I’m at the point of no return, so that I can stop being so come-shy around her. Or me watching her video while she’s jerking me so that I can start associating her touch with the turn on I felt watching her. But she’s never seen her videos and has asked me to not watch them anymore.

I’ve tried twice going to sex therapy with her, the last time at her initiation, but that triggered her and she declined to go back after the first two sessions (we have been in couples therapy several times otherwise). I’ve gone to a lot of therapy on my own and am at the point where it’s useless without my partner being part of it. I have also looked into getting a P-Shot. That's typically for guys with Erectile Dysfunction (ED), not Delayed Ejaculation (DE). It would reportedly not only make my cock a bit bigger, which she’d like, but also make it more sensitive, which could help me get over the top. But it’s expensive and I worry she might get triggered by this for some reason and the money spent would go to waste.

Yeah, I know — she’s a mess, and her being a mess has pulled me down and caused me to not take good enough care of myself. My sticking with her looks to others, and myself at times, like an act of low self-esteem and desperation. I’ve read books for survivors of abuse and partners of survivors, and lately I have had to pull away from her emotionally and tend to my own mental health. But my not coming remains regardless of who I’d be with. The two women I dated before her were also triggered by me not coming inside them, jerking me off for a long time and me still not coming, and that contributed to them dumping me.

Although I don’t have a testosterone deficiency, and my health is super excellent, and I am genetically young for my age, which is one reason why I was such a late bloomer, I can’t help but wonder if age is playing a role, and I’ve simply missed the boat.

No one can imagine how fucked up and hopeless I feel over this. After a long life of almost no sex and now finally having a beautiful hot woman who loves me, am I really cursed to never being able to come with and for her, or any woman?

Man Just Wants To Come

Holy shit.

I did that dumb thing where I challenge myself to respond to the first letter in my "Savage Love" inbox. Yours was first, MJWTC, so here we go. (There my Monday goes.) And like I told BOA, a reader who sent me an epic letter last week, there's a lot going on here, MJWTC, so you'll have to forgive me if my response is a bit scattered.

• "Then, just as I felt I was healing and it was taking take me less time, she got triggered over the whole thing and broke up with me." Yeah, being dumped for not being able to come on cue would put the zap on anyone's head, MJWTC, and it's particularly zappy for dick-having people with erectile dysfunction and/or delayed ejaculation. While it's nice that "love keeps bringing [you two] back together," your girlfriend's attitude toward you and your dick isn't helping matters. If the genders were reversed here — if you were a woman who had difficulty coming and your male partner was pitching fits about it — most people would tell you to dump that motherfucker and get a vibrator instead. And most people would be right.

• "How I got to this point feels like the worst sexual misfortune a guy could suffer." There are worse sexual misfortunes a guy could suffer.

• "All this lack of sex, starting from my teens, led me to first Playboy, then Penthouse, then pussy mags, then hardcore porn of all stripes... always leaving me disgusted with myself and porn." Sounds like porn worked for you. Later in your letter we learn it still kinda does. So maybe porn isn't your problem or at the root of your problem. Maybe the same "general sexual repression" that made you feel bad about sex also made you feel bad about porn. Maybe if you'd had a better relationship to sexuality generally and your own sexuality personally growing up, MJWTC, you wouldn't be pinning the blame on porn. Maybe porn was framed.

• "At last, five months before I met my girlfriend, I completely stopped watching porn and stopped jerking off, too. Three months into this discipline, I went to a sex worker who wasn’t even very attractive to me, and I came almost immediately when she sucked and jerked me." A guy can watch too much porn, of course, just like a guy can watch too much pro-sports or too much Marvelous Mrs. Maisel. A guy can also become habituated to his own right hand. Taking a break from porn and/or masturbating less can help some guys. It helped you. That still doesn't mean porn was to blame for your issue — or your unhealthy relationship to it. Again, I'd point you the same forces of sexual repression that screwed up your sex life. Masturbation, aka "solo sex," aided by porn or not, is a huge aspect of person's sex life. If your upbringing messed up your relationship to partnered sex, it stands to reason that it messed up your relationship to solo sex too.

• "She was highly sexual before met and was also, sadly, sexually abused over many years as a child." I'm very sorry to hear that. I'm also sorry to hear that she didn't get professional help to address her trauma and her triggers until you came along and recommended a therapist to her. And while her freak outs and those dramatic breakups may be related to her trauma, it sounds like being dumped and taken back and dumped again is traumatizing you. We're allowed to leave people who make our lives hell even if their prior victimization at someone else's hands is the reason they're making our lives hell.

• "But my issue is due more to me having watched so much porn while jerking off in my past decades of loneliness, my brain has changed to where nothing in person excites me enough to take me over the top." Porn does not have the porn rewire your brain.

• "I’ve never seen any woman get so deeply absorbed in the sexual experience and to orgasm so intensely as she does in these videos." She was acting — like almost all women who appear in porn, she may have been playing up how absorbed, entranced, turned-on, etc., she was. For effect. Or maybe she was that turned on and you two should recreate those scenarios together, MJWTC, if working on them is a pleasant memory for her. Regardless, MJWTC, if watching those old videos makes you feel inadequate, stop watching them.

• "I try not to masturbate at all between times when I see her."
You should start masturbating between the times you see her. You have a bad and worsening case of performance anxiety, dude, and not jacking off between encounters with a woman who may get angry at you for failing to come on schedule and/or dump you again at any moment for the same reason ups the stakes for each and every meeting. And ramping up the stakes always makes performance anxiety worse. You don't have to jack off as much as your used to, and you don't have to start watching porn again. But rub one out now and then, dude, for the sake of your own sanity.

• "She has a fear of feces." Don't we all? (Actually, we don't all.)

• "It reminds her of one of her abusers." If being jacked off is the more reliable way to make you come and your girlfriend is really invested in making you come herself but jacking guys off reminds your girlfriend of one of her abusers... maybe you guys just aren't meant to be together.

• "I’ve tried to get her to 69 with me, which is a big turn on for me, but she says it distracts her." So you can get her off during vaginal but it's hard for you to come that way, anal is out, sixty-nine distracts her, she doesn't want to get between your legs and blow/jerk you (could be a personal hygiene issue — you should ask), and jacking you off takes forever and isn't always successful, which makes her sad or angry or both. And not coming and being shamed for not coming and being dumped for not coming is making you miserable. Maybe she's not the right partner for you, perky ass and boobs or no perky ass and boobs. And jumping back to something you mentioned earlier in your letter...

• "Three months into [not jerking off to porn anymore], I went to a sex worker who wasn’t even very attractive to me, and I came almost immediately when she sucked and jerked me. I went to another sex worker and was able to come with her, too. I thought I was at last healed. That last encounter happened only a few weeks before I met my girlfriend." So things were improving until you met your girlfriend and it's all been downhill since. Maybe you'd be happier with sex workers? Or with some other woman?

• "Second, when on my own, I seem to have had the most intense orgasms when I was emotionally hurt and rejected." That's something you might want speak with a shrink about — that and your desire to see your current partner with another man, which is no doubt related. You could work through this to get past it, I suppose (and good luck with that), or you could work toward embracing and perhaps exploring this turn-on. Explore ≠ realize. You could explore this kink through fantasy play. And who knows? Hot and degrading dirty talk about other men might produce a sexier kind of anxiety — an erotic anxiety so powerful it overwhelms your performance anxiety and puts you over the top.

• "I’m not at all poly, I doubt I could share her, and [don't] want to open that door." Having a threesome or letting someone else watch your twosome — which is what you're talking about here — isn't the same thing as being poly. Polyamory means being in or open to concurrent romantic relationships; a woman with more than one boyfriend and/or girlfriend, a man with more than one girlfriend and/or boyfriend, a person with more than one romantic/sexual partner, etc. A threesome requires some sharing, of course, but not to the depth or degree that polyamory requires sharing.

• "On top of that, there seems to be this horrible karma of tons of distractions popping up, no matter how much I try to set the scene so that there won’t be, and despite there being no distractions when I’m pleasuring her to orgasm." Smoke some pot or invest in a home sensory-deprivation tank (pricey!) or a sensory-deprivation hood (affordable!).

• "The one thing we haven’t tried, even though we’ve talked about it, is me just jerking off with her next to me and relaxing, and she takes over when I’m at the point of no return, so that I can stop being so come-shy around her." Jesus Christ. STOP TALKING ABOUT THIS AND DO IT. Do it the next time you see her. Do it each and every time you see her. Fuck the shit out of her, get her off like you do, give her those multis, then pull out and stroke yourself until you reach the point of orgasmic inevitability. She can perform the final few strokes herself or — if she's still wet and turned-on and into it — you can shove your dick back in her pussy and come inside her. Dude!

• "Not masturbating at all when I’m not with her, so that she is my sole source of stimulation, seems to decrease my libido, and she’s so unpredictable with her freak-outs I never know when I’m going to see her next." Dude.

• "The most important thing I have learned from being with her is that I need to totally love a woman and feel loved by her to get excited enough to even get hard and fuck." Not true. See the sex workers you mentioned, attractive and otherwise, six hundred or so paragraphs earlier. I'm not saying you shouldn't be with or want to be with a woman you love. Love is lovely. But you are clearly capable of getting hard with someone you don't love — and getting off with someone you don't love.

• "But she’s never seen her videos and has asked me to not watch them anymore." Stop watching those old videos. Perhaps she'd be up for making a few new ones with you and watching those instead.

• "I’ve tried twice going to sex therapy with her, the last time at her initiation, but that triggered her." DUDE.

• "I have also looked into getting a P-Shot. That's typically for guys with Erectile Dysfunction (ED), not Delayed Ejaculation (DE)." The P-shot involves having the "plasma-enriched growth factors [present] in your blood" harvested and injected "into specific areas of the penis." The P-shot doesn't give you one very expensive erection; the purported effects — increased girth, more reliable erections, an increase in sensitivity — allegedly last up to 12 months. So even if your girlfriend bails on your first sexual encounter post-P-shot, MJWTC, you'll have other opportunities with her or, if she dumps you again, with other women.

• And speaking of DE: "Men with DE may be able to ejaculate with great effort and after prolonged intercourse or are unable to ejaculate in some circumstances," says this DE paper on the website of the National Institutes of Health. "Psychological causes of DE are constituted by fear and anxiety during sex, childhood sexual abuse, sexual trauma, repressive sexual education, religious beliefs, sexual and general anxiety, and relationship difficulties." That sounds like you, MJWTC. Biological factors can include taking anti-depressants, endocrine diseases, prostate surgery, and... aging. So there could be multiple contributing and overlapping causes/factors at play. Not just your upbringing, not just porn, and not just your girlfriend — although it's safe to say the drama with your girlfriend isn't helping.

• "My sticking with her looks to others, and myself at times, like an act of low self-esteem and desperation." Yup.

• "No one can imagine how fucked up and hopeless I feel over this." No one has to imagine, MJWTC, it's all right there in your letter. Once again, if you were a woman and it took you a long time to come and you didn't always come and your male partner was pitching fits and punching mattresses, MJWTC, you would be told — and not just by me — to dump the motherfucker already. Like a lot of shitty boyfriends out there, your girlfriend is making your orgasms — which were always somewhat illusive — all about her. That's an asshole move and it has predictably resulted in your orgasms becoming even more illusive. It's also making you completely miserable.

DTMFA.