Ask Beastly: My Husband’s Dick Is Huge—How Do I Train My Hole?
Tips for training your ass between sessions.
Hi Beastly, I've tried to find good answers for this question online but have failed, so I'm turning to you. I (cis, gay male) bottom about once a week for my well-endowed, girthy husband. Sometimes it's pain-free and an out-of-body physical experience, and other times it just hurts, and I really want it to be over. There's plenty of advice out there on how to prepare to bottom (on the day of), but I am wondering if you have techniques or suggestions of things I could do during the week to keep things more "receptive", so to speak. Sometimes I wonder if we should just do it more often, or if I should be wearing a butt plug more regularly. Any tips are appreciated.
Hey cowboy,
I made a personal vow not to answer any more questions about douching because I have beaten this subject dead, on this site and elsewhere. Browse my archives for several posts on the subject here.
I’ll be happy to address the rest—the tightness and pain. (I’ve also written about this quite a bit on this site: read this and this. There are more posts in my archives on the subject, but I recommend starting with those two.)
It will take years of bottoming for you to take big dicks painlessly. You need a lot of experience; in time, it will become easier.
Of course, good bottoming requires more than just experience, because it is, ultimately, a mental journey, not a physical one. Good bottoming requires an intimate curiosity and understanding of your pain and pleasure thresholds—and, making it so much harder, it requires you to stop worrying about poop long enough to fully relax. You must find your mental tricks that help you connect with your hole and let it open. You have to learn the many different sensations of being fucked. It does hurt sometimes, but that’s part of the fun of it.
But pain can also signal injury, so it’s crucial to discern the difference between “injury pain” and “pleasure pain.” To make this easier, I find it helpful to categorise sensations: Pleasure, Pressure, and Pain. In the moment, ask yourself, “Which one am I feeling?” and try to place the feeling in one of these categories. Knowing the category of the feeling tells you how to respond to it. Pleasure = keep going. Pressure = slow down, take deep breaths, or maybe take a little break. Pain = stop. (Discerning the difference between these gets even more critical in heavier play, like fisting.)
The sensation of getting penetrated deeply is different from being stretched and is a separate mental journey. Most bottoms are better at one or the other. Every butt is either a “width” butt or a “depth” butt. So asses naturally go wide and stretch easily, like mine, but struggle with depth. For others, it’s the opposite: they have holes you can plunge into and go deep, but they don’t stretch so well.
This has much to do with anatomy and what naturally feels good. Most bottoms are better at one and struggle at the other, at least initially. If you don’t know which one you are better at—if the sensation of his dick is just “oww!”—try to focus on what exactly is causing discomfort the next time you bottom. It’s helpful to know if the stretch or the length is what you’re struggling with; that will guide your ass training.
Plugs can help. Wearing one for extended periods might be fun, but it likely won’t impact your bottoming life; that’s just a fun fetish practice on its own (lots of guys like being plugged in public). But playing with plugs during your actual sex sessions can be a great warmup exercise before fucking—this is what I did before my (well-endowed) ex-boyfriend and I had vigorous sex, and it made a big difference.
How to do that: Slide a plug in and out (or, better yet, have him do it) until you can go quite fast and are comfortable with the gape and stretch. This is essentially the same advice I give another reader in greater detail here, and this is a tried-and-true method of learning to enjoy big things in your butt.
Congrats on having such a hung fella.
Love, Beastly