Plugging, Pegging, Fisting, Anal Play!

Submissive men can enjoy anal play. Dominant men can enjoy anal play. Bisexual / heteroflexible men can enjoy anal play. Completely straight men can enjoy anal play. Why? Because they all have a prostate! So whether it is a wet tongue on the outside (or a little bit in), or it’s one slim finger pressing on that little button inside (point towards the front) or it’s a silicone, glass or metal plug (some vibrate!), or it’s a strap attached to my harness (all sizes), or it’s my hand and arm buried in halfway up to the elbow, there are few things I love more than stretching a boy out…..and causing pleasure. Sometimes a bit of pain too, but it’s mainly pleasure I am after.

A big part of this is the power play. Being entered, penetrated, is a vulnerable thing, as women well know. Most men do not get to experience being penetrated, as they are the ones doing the entering in vanilla sex. The “natural” power dynamics, the much more common ones, are male dominance (giving) and female submission (receiving) as a result. So for many men, outside of the actual pleasure that can be derived from penetration and stretching, there is a delicious submissive element of being taken, entered, used. Some men, I find, are only pleasure oriented, and will only take the size that feels the best for them (of course this can grow bigger over time via anal “training”), and some are goal oriented, and want to keep pushing themselves to take more, to see how much the body can handle. And some men are humiliation oriented, so the plug or strap represents a way of being degraded (I have some plugs with a furry tail attached that are especially fun to tease with for this purpose). There are even those who don’t feel much pleasure, only pain, and still want that pain as a punishment or a way of being put into sub space. Finally, being entered sometimes has an element of feminization, sissification — which is why the anus is sometimes referred to in those cases as a boi pussy or bussy, and a prostate orgasm as a sissygasm. In this case, adding a pair of lacy panties over the plug, or a thong pulled to the side to make room for the strap, can be especially effective. So there are many different reasons to pursue anal play for a man, all of them perfectly valid.

From a domme’s perspective, it is no less a power play. To put a grown man, often one much bigger than you, on all fours, with his ass in the air (I will often say, “face on the floor, ass up, arch your back like a good slut for me”), while you stand over him and insert something into him…..well, it’s empowering. Or if he’s on his back, arms bound over his head, his legs pushed up high over his body, exposed and vulnerable while you kneel above him…..same, empowering. The cock, unless caged, is also exposed for teasing or torture. I like to milk a cock with my hands when a man is on all fours…..like a puppy, I tell him, or a farm animal. And if a man is on his back, the cock is even more accessible….whether you want to tease or punish, or, if it’s a beautiful one, you want to taste or ride….

As much as I enjoy inserting a finger, a plug, a fist, I have to admit that my favorite thing to do is to put on my harness, which I have owned for nearly 20 years, and which fits me like a glove, and attach a strap. Looking down, holding my girl-cock in one hand, my other hand on the man I’m about to enter from above or behind, is an incredibly empowering feeling. To have a big thick piece between my legs that I can use to open up a willing (sometimes very tight) hole…..that is an exciting moment. I tend to be gentle, not vicious. I use lube, I warm the person up with my fingers, I stroke the cock and balls, I speak in a soothing way. But I love sliding my way in and then fucking…..slow and smooth, then faster and harder, as much as he can take. There is physical pleasure in it for me. My harness rubs my clit quite nicely, especially if my clit is already sensitive and swollen from just having been licked to orgasm, which it almost always is….as I generally do not proceed to pegging until I’ve gotten my oral orgasm first. Sometimes the rubbing is enough to make me orgasm again. And even if it isn’t, it’s a very pleasurable sensation. At the same time, thrusting is a power motion. If you’ve ever seen the famous TED Talk on power posing for women (and men) in business, to create confidence, you’d better believe that thrusting while putting your hand on the back, or holding the hips, or handling the dick are all the ultimate in power posing. So many times I have gone from a pegging “lunch” to an afternoon business meeting just radiating that extra confidence. I think that many, many women could benefit from the same!

But as much as anal play is about the dominance of the giver, I think that properly done, it should always be about the pleasure of the receiver. I always talk about the extent to which domination is a responsibility. Someone offers you control over their body….and I believe there is less power in taking selfishly than there is in manipulating and controlling it generously, to give pleasure. Most people know how satisfying it is to please a partner, to make someone cum…..in that moment, when they are cumming for you, they belong to you entirely, you are giving them that moment of ecstasy, and they are reliant on you. So, as someone who wants to give memorable pleasure, I love the quest for the prostate orgasm, which can be elusive for some. And on the journey to that prostate orgasm, the prostate-assisted orgasm (centered on the cock but with prostate stimulation as an added layer) can still be great fun.

Many men have their most intense regular orgasm when also fingered or licked for the first time, and that sets them on the journey towards more anal play — with prostate massagers and vibrators, plugs, and ultimately dildos. Often, this journey is accompanied by no small measure of shame and guilt. Society often makes men believe that anal play is homosexual or submissive by definition, so more dominant or heterosexual men struggle with this the most. Many men also have trouble finding a woman who is willing to entertain such play, who will engage in it and enjoy it and not think less of him for it. This is because society conditions women too, to see a man’s desire for this sort of play as definitionally more homosexual or submissive, and many vanilla women want to see their male partner as “strong” and dominant. This is unfortunate, because while anal play can of course be about homosexuality or bisexuality or about submission, it need not be. At the end of the day, a physical act doesn’t need to have meaning or implication beyond pleasure itself. I find it a bit sad when I hear about women refusing to accommodate a male partner this way when he asks for it because it makes him feel good. Imagine if the shoe were on the other foot and the female partner asked for something she enjoys — cunnilingus let’s say — and her male partner turned her down instead of wanting to please her. We’d judge him more harshly, I think. To me, it’s all the same — being a good, giving lover is about making your partner feel pleasure, especially in the way that they are brave enough to ask for. So I encourage women reading this, even if not dommes, to think about it that way….as a form of play that a partner who has a prostate can really benefit from in most cases….and consider exploring it! And this goes double for women looking to explore a domme identity because, as I have already described, it is a particularly empowering kink for the giver.

There are a lot of mechanics and logistics involved that I won’t go into, but that can be easily researched on Google. Cleanliness is important (part of my play can involve enemas in preparation) as is tolerance/acceptance (the body is the body, poop does happen….), and patience, and lube. Chasing the prostate orgasm is about the sizes of the toys, the positioning, the speed, depth and firmness of the thrust….everyone needs something different. So exploration and patience is needed here too. Then there’s the question of where to cum…..one particular kind of domination I love most is a boy upside down, legs over my shoulders as I sit on the edge of a bed, his head on the ground, his cock pointing down at his face as I enter him from above, and if you position him just so, he can cum onto his own face or even into his own mouth…..incredibly hot. Lots of fantastic variation with this kink makes it easily one of my favorites!