I’m Alexander Cheves, a writer, author, and sex educator. My nickname is Beastly. I give adult advice on this blog — no question is off-limits. To ask me something, email AskBeastly@gmail.com or send a message via the Ask Beastly contact form.
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I met this guy in April through a mutual friend and we immediately hit it off. We began chatting, hanging out, then we began exclusively courting until finally a few months ago we decided we would be a couple.
You could say that opposites attract, he is very liberal- open to group sex, threesomes, voyeurism, and swinging. However I am considerably less liberal in a relationship though, because if I were single I would be open to be the third in a threesome, the third for a couple, and watching others have sex etc. This of course identifies an issue because this seems like a dream relationship for some. But the truth is I am insecure and fear that if I open up our relationship to others as he has indicated he is open to that he may enjoy himself with someone else more than he would with me and leave me.
To his credit he does not push the fact he wishes to open the relationship because he knows I am hesitant. He merely mentioned being open to it.
This is something that I am coming to terms with- the insecurity and fears- and trying to grow from and work through. However, that isn’t even the main issue I am writing about. The problem is that we are both well endowed. I am almost 9 inches and he is over 8. This presents a major issue with me because I am not used to bottoming as I have gone years between bottoming. And neither is he used to it.
I have played the bottom role in bed the few times we are actually able to have sex because he was forced upon by someone and it left him extremely scarred emotionally. He fears it and given that I am so large, it really doesn’t make the idea of him bottoming easier even though he says that someday he still would like to try.
Our sex life is almost non-existent and it’s a wonder we are both still together. Sometimes I wish to entertain the idea of him having sex with someone so he can have his release but my fears and insecurity get in the way. Yet, I too wish to release via topping someone or bottoming for a smaller dick.
He says that for him topping someone else would be just about sex, because it would not be the same and that he would still wish it was me. It would only be a release. I should find some solace in this.
I want to be able to enjoy all aspects of our relationship and I want for him to be happy. But each time we try it hurts. Whether it’s the tip he’s getting in or when he actually gets it in and it hurts inside.
I wonder whether its air being pushed around that’s causing this pain, or if because of the nature of his length and the slight curvature to the right of his penis that it’s rubbing against something. I don’t know.
We were successful once while in missionary, but attempts to recreate that moment has failed miserably. We were successful a second time a few weeks ago in doggy style and he came quickly because “it had been so long”. Attempts to recreate that as well have failed. Sometimes he doesn’t even initiate sex because he doesn’t want to hurt me. And if I initiate, he may lose erection again because he does not want to hurt me.
It’s frustrating for both of us. I have said we can try other things like oral and masturbation but I believe he would really prefer to be inside me and acquire gratification that way.
I’m a gym rat which means I eat for fuel and that might mean full meals each day especially on leg days where I need more fuel. If I go hungry, or eat considerably less I’ll get a migraine. So eating light, or not at all to facilitate bottoming is out of the question.
When I douche therefore, sometimes I wonder whether I am pushing air in there that then makes it painful to bottom. I am at my wits end. I’ve tried on my back- it hurts to get it in initially. If I try doggy style, same thing because each time he tried to go deeper, it hurts. He has been hurt while someone was on top of him and so he fears that and loses erections if I try this position because I could control depth. Also it doesn’t help that I’m 180 lbs of muscle while he’s around 165 lbs of lean swimmers build.
I’ve thought about purchasing dildos, butt plugs etc to practice with and get comfortable again with the feeling of a penis back there as well as poppers to relax but poppers are illegal in my country and purchasing sex toys can be challenging as well. Efforts to find someone traveling back home and who wouldn’t mind bringing them in for me is also a challenge.
I know the fear of being hurt makes me tense and it can be difficult to relax to allow penetrative sex, so that doesn’t help our cause, and of course to then take such a large penis is not helping either. Then to finally get it in the pain when he goes deep only reinforces my anxiety, fear and tension.
But what can I do? I can feel our relationship slipping away and I can feel our bond weaken. This is the first time I’ve been in a relationship since 2010 when I was at **** [location removed for privacy].
Sex was a bit easier back then. I lost my virginity and really began a new life where I bottomed and I topped to success. I didn’t even need to douche. I could just go and get on with it after nothing but a good shower and the requisite mutual attraction. Now I feel like I’ve regressed. It takes so much to prepare and then, success isn’t even guaranteed (in the case of bottoming).
I want to be able to build a strong relationship and a healthy and enjoyable sex life for us both. Maybe after that I would consider opening our relationship up. Or maybe (hopefully) we won’t need to.
But that starts with me being able to bottom without being in pain. But how? Why is it that so many others can do this so easily? Be double penetrated, take humongous dicks like nothing, entire fists, making this seem so easy, and then there is me, an utter and complete struggle!
Hi dream top,
This is all very hot to read, but I have to remind readers to please keep questions under 200 words — roughly one long paragraph. This question was sent to me before I implemented that recent rule.
There’s a lot going on here that’s wrong. People only enjoy the sex they want to have, not the sex they feel they must have to keep a relationship going. If you wanted to bottom — and it doesn’t sound like you do — then you’d figure it out the same way every gay man who wants to bottom learns how to bottom: through devoted time, effort, failure, defeat, and occasional moments of great pleasure.
Bottoming has a hard learning curve, and in the beginning it’s rarely very enjoyable, but we stick with it because we enjoy it, because we crave the submission and power and concept of getting fucked, and we bear the work that goes into it. If you’re trying to bottom because you think it’s what you have to do to keep him around, you won’t be successful.
Here’s a wild concept that people tend to forget: sex doesn’t care about your relationship. It’s a separate thing that obeys its own rules. Your sexual impulses don’t care that another part of you is trying to make a committed relationship work. Harmony happens when you satisfy two separate parts of yourself, the sexual side and the romantic side. Your relationship currently sounds disharmonious, and not because you both like to top and have big dicks, but because you’re only satisfying one half of yourselves and not the other. As I told someone in a similar situation: to make things better, you might have to accept the fact that you may not satisfy both sides of yourselves with each other. You have the relationship stuff down. Why not celebrate that and get your sexual needs met elsewhere?
I’ve written many pieces on how to bottom, as you can see from scanning my posts. And if you Google my name — Alexander Cheves — you can find more articles in mainstream publications on bottoming. These can help you with the mechanics of getting fucked, but none of them will give you the will and desire to enjoy bottoming. Bottoming is work. These guys you speak of, the ones who make it look easy? They’re dedicated, and they’ve been training for this for years. They’ve put in countless hours perfecting a douching regimen. They’ve had countless failures. They’re sexual athletes. Bottoming without pain is a difficult skill to learn, and painless bottoming without making a mess is even harder. They put in this work because they love getting fucked. You don’t love getting fucked, so you’re not going to put in this work. Find another solution.
The best solution, to me, is your boyfriend’s proposal. Open up the relationship. If you’d be willing to open it a bit, you two would be a dream come true for some skilled, lucky bottom. Getting shared by two hung tops who are committed to each other and don’t want anything more than sex? That sounds like a fever dream for me and for countless men out there.
When people struggle to have sex with each other and are in monogamous relationships, they don’t have many options. You can either a) change your definition of sex to one that doesn’t include traditional penetration and be happy with that, or b) open up your relationship to include outside playmates, who you may enjoy individually or together, or c) break up. Those are your choices.
You need sex. He needs sex. If you didn’t need sex, you wouldn’t be in this predicament. And if the sex you both need is strictly anal sex, you must both either enjoy bottoming or you should find someone who does. You’ve been trying the first option and it’s failed repeatedly. I suggest trying the latter.
Let’s return for a moment to this line: But the truth is I am insecure and fear that if I open up our relationship to others as he has indicated he is open to that he may enjoy himself with someone else more than he would with me and leave me. If you really believe he would leave you for someone else because they offer him better sex, you should dump him right now. Do you want to date someone who only measures your value in sex? Is he only with you for sex? If your answer is yes, why do you want to preserve this relationship? A relationship is so much more than sex. If people only dated the ones who fuck us well, we would never date, because there’s always a better fuck. My boyfriend is not my best fuck — he’s just my favorite person in the world. My best fuck is probably some stranger in a hotel room I don’t remember and don’t care to.
If you choose to open your relationship to outside partners, you can set a rule that you only play with others together, or you only play with others in certain situations. Non-monogamy lets you set these rules as you feel comfortable and adjust them as you go. The payoff of this work is feeling two sides of yourself — sex and love — being equally free. And that feels really good.
Hi Beastly, love your writing. I’m a 28 years old gay from Buenos Aires, busy city. I’ve been most of my life a top but with years I’m realizing that size might be an important feature in gay world — surprise!(?). I don’t consider to have and small dick, but also nor a big or thick one. In my times as a bottom I myself have enjoyed more with big dicks than with regular or small ones, is because of that own experience that I started to feel insecure on approaching guys. Be on the sharing photos part or the first encounter itself. I live it with so much anxiety that most of the times my perfomance seems affected. I know that it depends of the sexual partner but maybe you’d have experiences with regular dicks and might have a word of wisdom for me 🙂
I included your question with the one above so you can see something important: people struggle in sex regardless of anatomy. Yes, gay culture idealizes big penises, but even guys with monster cocks have troubles in sex and love.
Read my answer to a similar question. Sexual stamina and adventurousness have no correlation whatsoever to anatomy. And that’s a good thing. That means you have the ability to be a randy, adventurous playmate regardless of your body.
You’re currently linking two things that have no relationship with each other: sexual prowess and dick size. Sexual prowess depends on chemistry, charisma, confidence, adventurousness, roughness, gentleness, degrees of dominance and submission, the ability to listen, the willingness to try new things, and an eagerness to please. All these things can be cultivated and nurtured.
You can’t cultivate or nurture a big cock. Cock-pumping seems to work for some people, but it’s not a surefire way to get a big dick, and it’s probably not very healthy. The fact is, you can’t change your anatomy. But you can change all that other stuff, all those features of a person that foster sexual prowess, and those things matter so much more than being hung.
Ask any experienced gay bottom and he’ll tell you a story of a very hung top who was horrible in bed. Every bottom has been with one. We all know how painful and irritating that sex can be. At the same time, most of us also have a story about a guy with an average or below-average dick who gave us wild, nasty sex because he was adventurous, fun, and eager to please. Be that guy.
By asking how to be better, you’re already taking steps to increase your sexual prowess. Go forth and cultivate your knowledge of kinks, positions, sex toys, G-spots and P-spots, lube, pleasure tricks, and so on. Be game to try new things and be expressive and communicative when you fuck. Ask your partners what feels good to them, and tell them what feels good to you. This is how you became an exceptional lover, which is something anyone — with any dick size — can be.