I saw this essay some years ago and managed to find it. Its one of the best things I've read on the psychology of the Domme/sub relationship, through orgasm denial and the inrtoduction of the slow drain.
Anal Enslavement, or Why Anal Sex Is Different When Done To Males
This piece combines & revises several different source materials from various places, seeking to achieve a more compact presentation of the relevant details.
Its author’s name is a pseudonym…
-by Greta Cantoleva.
It has always been clear that one partner will always seek to "give it up" ... the mystery, apparently, is in why this is so.
When the one who yields is male, the secret is in his inner anatomy, not in his outer endowment -- many Domme-centric ladies use this knowledge to maintain optimum pleasure for themselves, while others continue on the altogether more problematic path of adopting stern demeanors of such startling contempt for the male that he is rendered not only quiescent
in his responsiveness, but also intimidated to such a degree he is unable to profoundly dedicate himself to the deep pleasuring of Her! By the employment of direct and skillful deep rectal stimulation, however, a Domme not only accesses his true submissive willingness, she re-orients his most basic instincts radically. He becomes both grateful and relieved to the point of the most able devotional sexuality imaginable, eager to be
used for her pleasure rather than simply resigned to his own abject humiliation. The difference is qualitative to the most extraordinary degree. And once he is thoroughly indoctrinated by such pleasure principles, the very notion of selfish, self-absorbed phallo-centric crudity rapidly vanishes. He learns who he really is, what his true purpose is, and how innately & vastly superior her demands always are and always will be. He gives it up, wholeheartedly indeed, without reservation or resistance.
What is male milking, you ask? Some think it is the repeated forced masturbation of the male slave to the point of his finally not being able to ejaculate ... some think it is the teasing and stimulation right up to the point of ejaculation, but with no actual release – taking him to the edge over and over, driving him batty with the denial of ultimate release. While such methods do insure a certain modicum of control, the most effective
technique goes much deeper into his being.
True milking actually denies the slave the one thing he truly loves to do the most: to explode his essence in a wild and utterly incapacitating explosive release. And this denial is achieved through the skillful violation up into his most vulnerable orifice. True milking is the controlled stimulation of the male sub’s prostate gland, causing the non-eruptive discharge of his semen ... “discharge” and “leakage” instead of spurted ejaculation, because discharge is not orgasmic like an ejaculation, but more of a constant maddening oozing and draining of his essence. She prevents him from his release, holding him at a point where her purposes are the only ones that matter. He is well stimulated, to be sure, but the intensity is so well controlled by her that he becomes his Lady’s total slave. This is denial, but with a critical difference: his deepest inner sexuality is manipulated to the point that enslavement to her wishes is his only release, is what binds him enduringly and without reservation to thorough and endlessly wholehearted pleasuring of his Lady.
The prostate is a small gland in men, felt approximately three inches up inside the rectum, surrounding the neck of the bladder and urethra. Its primary function is to contribute to seminal fluid. Milking is the deep and continual massaging of the prostate and surrounding area. Continual massaging of his prostate forces the slow release of his semen down through his urethra to his penis. This deep rectal forcing of his fluids is so spellbinding to him that it eventually and irrevocably makes him her sexual slave.
The massaging can be by fingers, or an object like a dildo. Fingers are the best for stimulation but a dildo will also work quite well and aids greatly in the humbling loss of control. Lengthy practice will assure the acquiring of the best technique for optimum dildo control and consequent anal enslavement of the male. Regular size vibrating dildos of about 6-8 inches in length are best. A ribbed dildo is particularly effective.
As stated earlier, unlike masturbation, which results in an explosive release (ejaculation), massaging of the prostate to the point of milking is neither explosive nor as acutely ecstatic for him. Again, massaging the prostate and milking the slave is a slow process that results in the draining of his essence as well as the draining away of his will to resist his Lady. It is hypnotically pleasurable but nowhere near the acute pleasure of cumming by jerking-off, or by being jerked off.
During milking, the cum oozes out in slow drips and there is no explosive ejaculation. To aid in the milking, grasp the base of the penis and squeeze the juices out while massaging the prostate. These expressed juices can be simultaneously smeared around his lips and nose while he is being probed with dildo or strap-on, to aid greatly in the re-conditioning process.
When being used anally via dildo, to get the best stimulation to his prostate he must also assist her by working the dildo against his prostate, arching and bending into its pressures. He will be more than eager to do this, grinding his hips. With practice he will become most uninhibited in his gyrations. So his Lady not only fucks him, but he fucks himself for her. He becomes her dancing erotic puppet at the end of her control.
Another thing about milking is that the slow drippings of his cum always leave him only partially satisfied, and constantly sexually frustrated ... he has a constant feeling of being on the verge of cumming so he keeps grinding and massaging, or wanting his prostate to be massaged, in the hopes of actually cumming. Blinded by the spell of her manipulatory invasions, he turns and moans and is helpless. This is really great for her, because right after a typical slave cums, he loses a lot of his submissiveness, and with a reduced feeling of submissiveness, the Lady also loses some of her control. Not so with milking: the slave is never fully sexually satisfied so he remains sexually frustrated, submissive, obedient and attentive. He will beg and weep and beseech his Lady to keep fucking him so he can get closer and closer to his release. Yet it keeps him on the edge of his ejaculation, without that critical orgasmic release.
His experience is a lot like what his Lady sometimes feels during clitoral stimulation from hand massaging, or from oral service, or from fucking, but incompletely so - if such stimulation continues and is done properly, his Lady can climax in a very strong manner, similar to when a male ejaculates. Not so with milking, since he remains on the edge throughout the milking, however long she may wish to prolong it. This makes him crave more and more stimulation, hoping he will be allowed a strong and final orgasm. The cruel and delightful truth is that it never comes, not for him. She can keep him willingly maddened indefinitely, subject to whatever erotic whims she demands.
What happens is the male becomes more and more eager to please her and to feel the extremes of her manipulation. Instead of the orgasmic release of cum, only those drips of cum ooze out... with ease she gets him to lick his own forced dribbles from her hand, addicting him to the juice she forces out of him – since he is constantly draining and constantly kept from a full-blown ejaculation, he comes to crave this taste of himself and this state of affairs and becomes conditioned to these subtle but extraordinary sensations, knowing it’s the only way to please her.
So his Lady, thru teasing, orgasm denial, and milking, conditions him endlessly, and she gets him to love being fucked up the ass (and to finding his penis relatively useless, except for peeing and dripping cum ... it’s entirely up to Her!). She can get him to desire being bound and restrained, to love being flogged and love drinking his own essences, and, through her dildo fucking him constantly, love to be taken anally over and over for long periods of time. She can settle over his face with her own hips as she continues to grind her dildo against his inner organ, forcing him to pleasure both her cunt and asshole with his nose and lips and tongue as long as she wishes, rubbing herself over his upturned head exhaustingly, thru the repeated multiple orgasms she will be able to give herself. Not exactly face-sitting, this is more like face fucking! An ideal posture of worship for the male and for the female alike. And if the Lady is one who particularly enjoys having her the rim of her anal sphincter tongue-fucked, she will be able to indulge herself in this pleasure indefinitely. He will beg her not to stop fucking him, burying his tongue repeatedly.
He becomes her lap dog forever, if that’s what she wants . . . he will deny her nothing. Beatings and humiliations of any and all variations are hers on demand, his upturned cheeks hers for the taking, whenever and however and for as long as she needs. Her only limit will be her own ongoing imagination and physical stamina. She paces herself by alternating deep rectal churning with other activities, gradually reshaping the contours of his libidinous nature to her own lust. She eventually gets his conditioning to the point of making him bow to her wishes with no actual stimulation of his penis at all, simply through touching the vibrating head of her dildo to his pucker, or even just by saying it -- a whispered promise that she’s going to fuck him will have him on his knees instantly, his happy, eager face upturned. Or anything else upturned. Lady’s Choice!
Because the male's truest submissive nature is most clearly revealed while he is in a state of sexual frustration, it’s best to persist with this particular method of domination at all times.
To keep him in a state of total need and uninhibited willingness
to please her is the goal. And, as explained above, milking is what accomplishes this, beyond any other technique at her disposal.
What follows is testimony from an experienced male submissive, telling of the complex joy of his being enslaved by his Mistress thru orgasm denial, milking, and deep rectal manipulation:
“As far as the milking, I am not only getting used to this, but I actually crave it more than any other thing. It used to take longer but now I find that once the massaging starts, my penis starts to drip and ooze right away. I love the slow oozing, I love the taste, I love being kept open beneath her.
As mentioned earlier, when milking is done using a dildo, to get the best stimulation to the prostate I must also help by riding the dildo deeply back and forth along my prostate. So when Mistress Ramona fucks me, I will twist and grind my ass and hips like the slut I am to drive the dildo deeper, right onto my prostate. My ass has become my cunt and my prostate has become my clit and Mistress Ramona's dildos have become my best friends. I am also finding my penis to be of less and less
use to me. At times it is almost a nuisance. It is hers completely now, solely for whatever use she makes of it. To tie it or clamp it or drip wax upon it or to put extreme stress to it in any way is her right, by all means. I have no say. I want no say.
She also would use teasing whenever She could. She would have me kneel in front of Her to massage Her feet. While I lovingly caressed Her feet, Mistress Ramona slowly spread Her legs. She would then have me remove Her panties with my teeth. Mistress would spread Her legs to expose Her beautiful Pussy. She would then slowly place Her finger into Her pussy and begin to pleasure Herself. She would say how She wished She had a nice cock in Her right now. She would look down at my penis, laugh and tell me to fetch one of her vibrators. I would then continue to massage Her feet while She pleasured Herself. She praises me and tells me how good of a slave I am. She rubs my ass and balls and lets me lick Her feet and hips. If I have been able to cum with a full load, She has even poured my cum on Her beautiful feet and lets me lick them clean. Whenever I am milked, Mistress Ramona likes to collect my cum as it comes out of my penis into a cup or bowl. Mistress Ramona also likes to rub it on Her strap-on dido and have me suck it clean.
I now find that when my Mistress talks about fucking me or of Her wearing Her strap-on dildo, I immediately become excited.
I also find that when She fucks me, I want so much to please Her, to give Her enjoyment and receive Her approval. I now enjoy all fucking positions. I do find that some are better for stimulation of my prostate and that some are better when I get closer to cumming. Oh I love when She fucks me from behind with me on all fours and I can feel Her soft thighs and belly against my ass. Mistress likes this position, too, because She can see my cum as it drips from my unused penis. She wets her hand with my cum and rubs it over my face while she fucks me.
Mistress likes to ask me how does it feel to have my ass turned into a pussy for her pleasure - oh how She loves to fuck my male pussy, getting me all wet and slippery with her lubricants, like a cunt would be! I also love when She lays me on my belly with my legs spread and tied to the post of Her bed, exposing my open backdoor for Her use. I find this position also gives me good prostate stimulation. Finally, I love when Mistress lays on Her back and She has me lower myself onto her strap-on and has me fuck myself, sometimes facing her, other times with my cheeks toward her. In this position, Mistress likes to watch me pump my hips down and around, thrusting the dildo into myself harder and harder, trying to reach the orgasm that never quite happens. It is one of her favorite postures for me.
Whatever way She fucks me, I love it when the head of her dildo first enters me and She begins to take long stokes in and out, but She particularly loves to tease the thick head of her dildo right at the mouth of my anal ring, slipping in just past the first sphincter, then pulling it right back out, over and over. This goosing makes me almost lose my mind, but not my load . . . she says she gets a kick out of watching how my pucker reacts to the in and out motion, like lips . . . and the moaning I do is a real treat for her as well, and when she combines this kind of play with twisting my nipples or flogging, she can make me very verbal!
She knows that Her conditioning is working because, through milking, my sexual desires and needs are being met, and that in this way any male aggression I might be feeling is channeled for her own needs exclusively. I am completely open and willing to her whims and wishes, eager to serve her every command. We each have the best of all possible worlds!”