My name is Alexander Cheves, and my nickname is Beastly. I wrote a book.
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I’ve met a guy on Grindr, we have a long-distance relationship, which is a strain, I am 58 & he is 35, we meet up when we can which is about 4 times over the last 8 months. whenever we meet the sex is fantastic, but he gets very frustrated that I don’t cum. He says that I don’t love him unless I cum, when we meet, we see other guys when we are apart and when I am with other guys I usually cum,
I need this guy in my life, we are in love & have discussed the future together, I feel relaxed with him & want to cum but something is wrong with me that I can’t, he is high maintenance, and he suffers from Aspergers & stress. I, on the other hand, am married with a terminally ill wife, which is why we can’t get together full-time.
hope you help & give me some advice, thanks in advance
My love, your relationship is a mess. Here are the major factors working against it:
- long distance, which has a poor success rate even in the best conditions
- him pressuring you to cum, which amounts to a bullying backhanded ultimatum (“cum or I’ll assume you don’t love me and leave”)
- a physical and ethical obligation to prioritise the care of your terminally-ill wife over the “high-maintenance” needs of this young man
It is a red flag to me that he is demanding and “high-maintenance” while (I assume) knowing you have a terminally-ill wife — and is not factoring the pain and stress of caring for a sick partner into your inability to cum.
But let’s examine this “inability”.
Ejaculation is not the same thing as orgasm, and there are many ways to orgasm that do not involve cum (like prostate orgasm, anal orgasm, mental orgasm, emotional orgasm, and much more). If you are struggling to orgasm, remember that orgasm is not a purely physical thing, something the body does automatically in response to stimuli. The mind is also part of the process.
Humans are not robots. You can’t plug in a formula of blowjob + anal sex (just as an example) and get an automatic outcome (a big burst of cum). Orgasm is mental and emotional and depends on feelings of comfort and security as much as on physical sensation. What your boyfriend is telling you about cum is false. Orgasm is not dependent on love (I’m sure you have cum in or on guys you don’t love) nor is it an indicator of love — but it can be an indicator of stress and discomfort if it doesn’t happen. And sex with someone who pressures you to cum — and says you must cum to show them love — sounds stressful.
Orgasm is a strange dance, one you mostly have with yourself. When I get in my head and feel overwhelmed during sex, which happens quite often, I remind myself that I know my body and my pleasure better than anyone — better than whoever is currently playing with me. I imagine sidling up to myself on a dance floor and whispering in my ear, “Ok partner, want to go another round?” My body is a familiar dance partner and we’ve been at this a long time, ever since those first exploratory masturbation sessions, humping a pillow in my bedroom before I even knew what masturbation was. What a journey we have been on. I trust myself more than anyone else to take me there. When I have sex, both sides of me — body and mind — agree to let this third person, this stranger, whoever they are, please us. We let them in.
It helps to check in with yourself, check your breathing, and ask yourself if what is happening is wanted, if it feels good, and if you feel comfortable. I cannot cum if I check in with my mind and discover that things don’t feel right. Both sides of me, body and mind, must be comfortable and in mutual agreement and enjoyment. If my mind is resisting for whatever reason (the reasons are not always clear to me in the moment) then no amount of physical pleasure will take me to orgasm. If my body is tired, my hole irritated, or there is some other physical sign that my body is saying no, then it does not matter how horny I am. My mind can be hungry for more and I know it will not happen. When my body says no, it’s time to stop. (I half-jokingly call my hole a fickle mistress, one who cannot be disobeyed. When she wants it, she wants it, and when she doesn’t, it simply will not happen.)
We are minds living in bodies. Orgasm happens somewhere between both, and both mind and body must feel relaxed and safe in order to experience one. Orgasm can (and should) be a vulnerable and trusting experience, so you need to feel safe with the person you experience one with. Like many other aspects of living in a body, orgasm is something you can never fully wrangle into submission. You have a relationship with your body, and in all relationships there are mysteries. The body will surprise you sometimes, disappoint you other times, and mystify you most of the time. If you stop pressuring the body, setting tough expectations of it, and accept it as it is, you will find that orgasm and pleasure come more easily. And stress, anxiety, pressure, depression, sleeplessness, illness, and any number of other things can inhibit orgasm — along with certain medications and conditions (it’s never a bad idea to get your testosterone checked).
I don’t think you have a problem achieving orgasm (ejaculatory or otherwise) as, by your own account, you can do so with other guys. I think this young man is pressuring you, and that pressure is creating performance anxiety that is keeping you from orgasm and cum. He’s creating a sexual headspace in which you do not feel safe, relaxed, or at ease. The more he pressures you to cum, the less likely you are to do so.
Instead of being sympathetic to the stressful conditions of your life and the demands of your primary relationship, he is adding stress with an ultimatum: “If you really love me, you will cum. If you don’t, I will assume you don’t love me, and leave.” There’s an unsubtle threat of abandonment in his false claim that cum = love. That is so incredibly mean, especially considering your circumstances with your wife, that the overall picture of him isn’t good. He sounds like an asshole. He might have Asperger’s or any other form of neurodivergence. That is still no excuse for indecency.
I am thinking of two gay men I know with Asperger’s (though progressive therapists now prefer now to say “neurodivergent” or “neuroatypical”, which avoids slapping a specific condition on someone and instead acknowledges that brain functioning differs among humans and, while a majority of people will fall into a bell curve of normative brain functioning, there are outliers whose minds are not sick or ill, just different). One of these men is a gentle, kind human whose brain just works a little differently: he doesn’t read social cues, does not read sarcasm, and struggles in social spaces predominantly filled with neurotypical people.
The other guy hits his boyfriend. He then apologizes profusely and says he hits him because “he has Asperger’s.” I cannot diagnostically evaluate these two men psychologically. I am not a clinical therapist, so I cannot say the first one is genuinely Aspergic while the second is just an asshole. But I think the second one is just an asshole. I think the second guy is giving a bullshit excuse for his bad behavior, which should offend everyone who (like me) is genuinely neurodivergent and not abusive.
I don’t know all the things you love about him besides the fact that the sex is great (it is telling that no good attributes are listed in your question, only problems). But from this small glimpse, he sounds more like the second guy: someone using a legitimate mental struggle as a cover for simply being mean.
People orgasm when they are relaxed and comfortable, not pressured. He’s pressuring you. You are already pressured by the demands of caring for your sick partner, along with the stress of traveling as often as you can to meet someone who lives far away. It is no surprise to me that you can’t cum. Your question is stressful just to read. I can’t imagine living it.
My honest advice: dump him. Care for your sick wife. Let her pass with dignity, affection, and attention. Keep fucking guys on the side, or even put yourself on the market for another boyfriend — ideally one closer to home and more sympathetic and emotionally mature than this one.
Thanks for all that you do. While I have heard of Lesbian Bed Death, I believe I am a victim of Gay Bed Death. The long (pun intended) and short of it is my husband has no libido anymore. Mine has remained unchanged: 2xweek. Typical story: hot and heavy when we met, now, after 10 years knowing one another, less than once a year. And, this less-than-annual occurrence is less than satisfying for me. I give a blow job, he sometimes strokes my cock. We haven’t had anal in 3 years.
I understand that communication is key, and I have started conversations on the topic several times in neutral settings in neutral ways. One agreement was that we would have sex on Sundays . . . but I was the only one who ever requested. When it does occur, it is, as mentioned earlier, not totally fulfilling for me with as little, if any attention, paid to my pleasure. And, as the sole initiator, I do get the sense that I am begging for sex.
Since pledges for improvement in frequency have not followed-through, what is the next conversation: The discussion to open-up the relationship (not sure how I feel about that yet)? The discussion to end the relationship entirely? Is there another option? I want sex but I am at a loss on how to start the next discussions with someone I love and who loves me. If I am avoiding the obvious, how to start? I am not looking for a roommate.
Sorry, but those are the only two options. Open up or break up.
I have given this exact answer many times, yet people still submit questions like this thinking, perhaps, that their relationship will be the exception — that a new, epiphanic third option will reveal itself this time. My dear, you are in the same situation as many others and have to make the same tough choice.
But it’s not really a tough choice, is it? It’s actually a pretty obvious one. No one can or should be expected to be starved out of sex for ten years. He might love you, but he is not caring for you or putting in the work to make you happy and sexually fulfilled.
You are not happy with the relationship as it is and can very specifically state why. You can clearly define which needs are not being met. You should bluntly and directly tell him that these needs must be met for this relationship to continue. Tell him you either need him to satisfy these needs or you need to go find someone who will. If he can’t stay with you while you go find someone (or several people) to satisfy your sexual needs, you should break up immediately.
Personally, I feel that conversation is pointless pantomime. You have already discussed these needs. You have already had some version of this conversation. Even after discussion, he has not risen to the challenge of satisfying a pretty basic requirement for happiness — sex — which is a dealbreaker in the most obvious way possible. He is clearly not too concerned with your needs, and even if he is, he is unable or unwilling to satisfy them, so I don’t see him responding to this ultimatum with newfound enthusiasm to start initiating sex. I imagine he will see your ultimatum for what it is: the reason this relationship needs to end.
You and the gentleman above in a stressful long-distance relationship would both do well to remember that love can (and often does) exist independently of sex. I believe you love him. I believe he loves you. If you have loved each other for ten years, you will probably go on loving each other even after you separate, in the same way that I still love all my exes. But this doesn’t mean you need to be together.
You won’t separate because of a lack of love. You will separate because the conditions of your relationship are not only un-optimal, they are actually inhibiting. Your relationship is impeding your ability to develop and enjoy your sexual side. It is decreasing, not increasing, the quality of your life. You can love someone deeply and still be in a relationship with them that isn’t making your life better — and that is what you are in.
Time to pack the bags.
When I was younger, 24yo (Im now 31) i had a bottoming experience with an unexperienced top, who was way too eager, and well, I tore. To the point where I was in pain for months and months, and it was excruciating, and despite my best effors had a lot of resets. Even now if I poop too much, Ill feel mild pain for awhile.
Im now married, to a very very understanding husband, who would like the experience of topping me. But Ive put him off due to the trauma of the past experience. Now, after 7 years of being dick shy, Im ready to try again. How do I avoid tears and if they come, what are your go to products/methods to heal?
You should talk to a doctor if you are still having rectal pain from a sex encounter that happened seven years ago. I do not feel comfortable making any sexual advisements until you’ve spoken with a medical professional about this. That is a long time to still be experiencing pain, even from a severe anal fissure or tear. I don’t know if you went to the hospital following that incident, how you were treated, or what exactly happened, which is why it’s hard for me to make any specific recommendations.
Generally speaking, the only way to avoid tears is to start small, go slow, use enough lube (and the right kind of lube), and be gentle. This is the same advice I give to anyone starting any kind of anal play, regardless of their sexual history. There is no fool-proof, 100% reliable method to avoid hurting your butt, but if you go slow, use ample lube, and be gentle to your ass, you will avoid tears most of the time.
Bottoming skill develops over years of practice and for most bottoms, those early years will include an anal fissure or two (or three, or four). I got fissures more frequently when I was a beginner. I have trained over years to relax and open my hole without pain and have advanced from gentle bottoming to pretty extreme ass play. But I started gently, with small toys and small-to-average penises, with a butt that was just as tight as everyone else’s when they are new to this. My journey — and the journey of any skilled bottom — proves that with practice and training you can eventually do quite a bit with your butt. But you have to start on the shallow end of the pool and very, very slowly work your way deeper. Envision this process happening over a decade, not just a few months.
It is a good idea to invest in rectal anti-haemorrhoid ointment to use following every ass play session. This ointment will reduce swelling and inflammation. If I have a small tear (which happens less often now) there is really nothing to do about it but wait, rest, drink plenty of water, consume a high-fibre diet, treat my hole with topical anti-haemorrhoid ointment as necessary, and stop sex for a bit. Just stop fucking and let it heal. Depending on the severity of the fissure (the severity of pain or the presence of blood), you might need to go to the doctor, who will likely do a rectal exam or possibly a scope to see if there is greater damage inside. If there is a lot of blood, go to the Emergency Room right now.
Don’t lose heart or give up. Enjoy being where you are. Beginner bottoming is very fun. It is the novel and wondrous first leg of the bottoming journey, one you will only go through once. I was living in Savannah, Georgia when I first started bottoming. Now, years later, I look back on that place and those years fondly. I knew little about sex and learned so much in a short amount of time. New discoveries rocked my world and seemed to happen every weekend. Sex seemed like a magical land in which anything was possible. Sex still is a magical land and I’m still on the journey — I always will be — but I am more experienced now and the discoveries have changed. I am developing my sexual side now, not discovering it, and while that is fun, it is not the same as being an eager beginner. You might not realise that you are at a fun part of your sex life, but you are.
Be gentle with your butt. Don’t set unrealistic expectations of it. Try to appreciate where it is now. With practice, the pain will diminish, the pleasure will increase, and you will discover what all these bottoms are talking about. It simply takes time, patience, and practice to get there.