This article is for those who are curious about anal play: how to try it…or what to do if it didn’t live up to your fantasies.
I’m a big ol’ anal top and have been taunting, training, and taking butts for almost 15 years now. Little butts, big butts, virgin butts, hungry-hungry-hippo butts. It’s one of my favorite things*. Butt, alass, this is not the case for all.
Sometimes when someone volunteers a little bit about why they dislike it, such as “I didn’t enjoy it because it hurt” or “I tried it once…wasn’t sexy”, I will ask if they don’t mind me inquiring further about their experience (for my own research purposes). What I usually discover is that they either tried it themselves and didn’t know what they were doing or they were introduced to it by a girlfriend or Domme who didn’t know what she was doing. It makes me sad because one bad experience — or even one less-than-hot experience — can sour people to the point of never wanting to try it again.
The reason why this happens is because people don’t bother educating themselves about how it works, what to do, and what not to do. They think it’s as simple as Put Thing In Hole. They don’t consider how their body might react or how it needs to adapt. Then, because they don’t know these things, they make assumptions and end up writing the whole thing off.
There is a common misconception that your first experience will look like what you see in porn. You know, that hot FemDom clip where she’s ramming a huge cock in his ass and he’s moaning in bliss. You swoon, “Ohmygoddess, I would do anything to be fucked like that!” I hate to break it to you, my slut, but that will not be anywhere close to what your first experience will be like. That is what may happen if you spend some quality time training your ass.
The reality is that your first experience putting something past your anus and into your rectum may feel unpleasant. Maybe even a little painful. You may feel like you suddenly have to shit. Which is the opposite of what you were expecting to feel. And is it at this point that some people decide they hate it. Because “this is supposed to feel as good as that FemDom clip looks!” and it doesn’t so horniness turns into bitter disappointment and the dildo goes into the dark drawer, never to be seen again.
Well, I say: give it another try. But let me help you get started on the right path.
If you want to experience what it would be like to be fucked like the gasping, whimpering, writhing-in-ecstasy bottom in the clip, start by exploring your own ass. Look at it in the mirror. Touch it. Touch the area around it. Pay attention to how it feels when you lube up your finger and just slide it around your anus. Be gentle. You want to make friends with your budding cockhole.
Once you’re comfortable you can get ready to slide something in.
If you’re not sure where to look for the right toys there are plenty of guides online. (I may just write one myself.) Without a little help, people may end up getting something that’s not suitable for them. This can be because you feel like a kid in a candy store and you just buy whatever looks like it would feel good in your ass. It also can mean you may unknowingly buy something that shouldn’t actually be touching your private parts. See, the sex toy industry is not regulated and so they’re pretty much free to use all sorts of toxic materials to make the things you are rubbing back and forth against your delicate insides. Some of these compounds can be absorbed by your tissue and some of them are linked to things like endocrine disruption, birth defects, and cancer.
Another issue that can confuse consumers is that you can’t trust that a manufacturer actually knows what the hell they’re making. It’s true. Some of them clearly haven’t ever done the activity they are making products for. (I’m looking at you, Random China Brand Often Found In Places Like Amazon, eBay, or Alibaba.) Take for example this plug:
Notice the way it’s marketed: “Perfect size for intro anal play”.
Hunty, this is in no way an “intro” plug — unless you are an elephant. This plug has a circumference of 6.5″. You know what else has a circumference of 6.5″? My vitamin bottle. No beginner should be trying to put a vitamin bottle in their ass.
Here’s a comparison of the above plug with a plug that is actually more suitable for introductory play:
When you’re ready to try putting something in, start with something small. Like a finger. The actual beginner plug on the left is like a finger. A meaty, manly finger that will probe your wet, hungr–oh, sorry. I got carried away.
If you’re using a toy, and it’s not a body-safe material like silicone, glass, or medical-grade stainless steel, be sure to slide a condom on it. (We don’t want sexy time to later turn into anal cancer time.) If you don’t have a toy, or a meaty, manly finger, use your own finger. If a finger still feels too big, use something with an even smaller diameter. This could be a pen, wood dowel (make sure it’s not a wood that will easily snap in half), or anything else that doesn’t have sharp edges that can hurt you. And, of course, put a condom on it, too.
If you’re concerned about the possibility of getting a little poo on your hand, put a glove on. Or, if you want to be sure that there will definitely not be any poo on your hand — glove or not — you can get one of those cheap enema kits (like Fleet), empty the contents, fill with lukewarm water, and gently rinse yourself out until you’re clear.
Once you’re ready, lube it up.
Lay on your back and slowly slide the toy or finger in. Not very far; just the tip. Just enough to get your anus familiar with the sensation of something going in instead of coming out. Breathe and relax while you’re doing this.
Once that feels okay, you can slide it in a little further. If it doesn’t, either just sit there and wait to see if the discomfort passes or, if it doesn’t, take it out. Wait a few moments and try again. Then breathe and relax. Repeat. Until you have it where you want it.
If it feels uncomfortable, focus on relaxing that area. If it still feels uncomfortable, you can stroke or use a vibe on your cock or clit and see if that helps. If not, you can stop and try again another time.
Keep in mind that it can take several tries to feel any pleasure. And for some it never seems to feel pleasurable. That’s okay. You can do something else. Maybe come back to it next month or next year. Or never. Whatever you want.
For those who do find the right feel and are ready to move on, you can size up, if that is your goal.
Again: always use condoms on unsafe or unknown materials and always with a lot of lube.
Once you get to where you feel like you can take a dildo, start slowly there, too. No matter how eager you are to be your Mistress’s dirty, dirty slut, don’t force anything. You can injure yourself, which can be very painful, and possibly lose some of the progress you’ve made as your body heals.
Now, for those who want to ask a professional Domme for anal play…
*Please be aware that some Dommes don’t openly offer it. The reason is laws can make it a risky endeavor. This is because, depending on your jurisdiction or which judge’s courtroom you may unfortunately end up in, anal penetration within a professional practice could be — and in some cases definitely is — construed as “prostitution”. Therefore, to be safe, some Dommes, like myself, do not advertise it.
You can mention that you find anal play interesting. (Unless she indicates it’s a hard limit.) You can tell her what your experience level is. Just be prepared that the negotiation process may be slightly different than other activities, if she is willing to negotiate it at all — especially if you have no references. Just be patient and follow her lead.
Once you do get to the point of making that dream come true, be sure to rinse that hiney out. Practice beforehand until you’re good at it. Then make sure you do it before you arrive for the session so there aren’t any surprises. Then, relax and enjoy every minute of it!
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