Training my Subjects Part 2

by Mistress Lucy H. Cunningham

Well it been 9 months since I started training Benny in earnest, and as you can imagine, it’s been quite at trip! I knew he’s a bit of a character, but now he’s really blown me away on several levels. More on that in a few. But to be perfectly honest, certain aspects of his training were very easy. After all, Benny has been a BDSM player since college - a very long time. True, my chastity program is not “playing” per se, as in contracting for a 90 minute session, for example; it is very much true-grit reality – he gave me his cock, for crissake, how much more ‘real’ can we make it!. Ohhh, there’s nothing quite like reality – it can be the ultimate mindfuck when manipulated correctly. And manipulate it I do…often, totally and with great gusto.

We started the process slowly. Benny finally found a design he could live with, not to mention the spare several thousand bucks to buy it. With my approval he settled on a surgical steel tube custom made by a firm in Montreal. The tube has an appendage that wraps around his ball sack and also has three holes: two which allow a bar to pass through the tube horizontally (and also pass through his frenum piercing) and also a larger hole to accommodate a future Prince Albert piercing. Right now the device is locked in place with the frenum bar which works fine. I can’t wait until we get that PA; Benny thinks that the frenum will continue to be his locking mechanism, but I have other plans. I want a big, thick PA to be holding him down. Mmmm. One thing that I had not bargained for is how sexy the key itself is. Who knew how revered a fucking key could become? Benny stares at it like it’s the Hope Diamond and I just adore attaching it to a necklace and letting it fall cavalierly into my cleavage. I can’t quite describe the feeling of power it gives me. Not that locking up his fucking dick is any big whoop, I mean it’s really of no use to me. Still, the feeling of power is undeniable, and I’m all about feeling powerful.

As we began, Benny was locked for two days at a time. During each lock-down period I made him write his impressions in a diary, which, to my surprise, he found rewarding. As good a writer as Benny is, he never got into keeping a diary, finding it to be a self-conscious but of tedium. (“I went to the park today and saw a beautiful red-breasted robin. As I probed it’s preternatural sense of self…” Oh, fuck, gag me; I totally understand his aversion to such drivel. In this instance, however, Benny related all the delicious details of the mental torment he is experiencing and that I am causing. I just love reading about it, knowing that I am responsible for these feelings and indeed his entire mental frame of mind. All he wants to do is serve me. That was always the case, but locked down. the feeling is multiplied. I’m a little iffy on him getting too involved at this point so I provisionally settled on writing assignments as his job. He wants to be my cook/artisan/footstool, but that will just have to wait, if it comes at all. Interestingly, all the so-called “experts” on chastity training recommended beginning a regimen by locking up the property one day at a time, but I wasn’t having any of that. I’m too busy for such nonsense, though. of course. I am always available in a true emergency. Two days just struck me as a good compromise – two days in chastity and then two days of freedom. Good way to start! Freedom is relative, of course. In our case, “Freedom” means he can cum when I call or text him that he should. He is instructed to be on his knees and cum into his dog bowl. I’m always interested in knowing how long after my initial order before he is happily lapping up his spooge. Benny adores tantric sex, so left to his own devices it would take four hours of self-torture (nipple clamps) and lots of visits to the nexus of frustration and relief before finally releasing. Well, fine, but I wanted to cut down that timeframe in order to shape Benny for his new reality: only having brief periods of time in which to self-arouse, climax and tongue-clean. I decided that three minutes is ample time to do the deed. If I am feeling particularly generous and wanting to indulge Benny’s romantic streak, I may allow more time, while softly encouraging him with words, caresses, laughing and pinches. Other times, I might allow only a minute and a half while sadistically torturing him. My favorite thing (and his too, I suspect) is to go from bright and sweet to cold and cruel in a millisecond. After letting this new mood sink in, I matter of factly explain to Benny what the consequences will be for non-compliance within the allotted time (will it be a fisting, a severe caning, a week in lock up, oh, so many choices). Finally, with an expressionless face, I keep time while doing everything in my power to distract him. My dream is to put him in a humbler and have him attempt to jerk off while in an awkward position…with me dragon-tailing his balls, of course. Yummy. Gotta get that humbler.

One thing I had not really thought through is that there is a lot of cumming going on, which is sort of counterintuitive. I mean, chastity equals not cumming, right? Well come to find out (sorry!) chastity also means cumming as a way to delineate the end of a chastised period. Initially, in the 2 days locked / 2 days free scenario, it really did not matter; I could easily unlock him and simply send him on his way. But I started taking a perverse interest in his first orgasm after lock-up, and directing how he comes became an unexpected point of intrigue for me. Shit, if you’re going to own someone, might as well control the whole show, right? *Sigh* That leads me to my boy Xavier.

Xavier finally “got” the Mistress Lucy/Benny thing: Benny is my acolyte, my chastity slave and above all my pet. None of these things threatens the office Xavier inhabits, nor should it. After all, Xavier frequently spouts off that he would like to live in a poly-amorous BDSM family, and here he can’t even accept the fucking pet! Jeeesh. Actually, Xavier is young but not hopeless. I think he really does get it now. And, you know, if he can wrap his head around the concept, Benny could probably teach him a thing or three. Interestingly, Benny informed me that Xavier has been perusing his profile on CM. Hmm, interesting. But the improved karma is all very recent. For months all I got was attitude from Xavier when it was time for Benny to come over. Early on I decided that Benny’s visits would require “corner time” for Xavier. At least that way there would be no tantrums. Meanwhile as time went on I started thinking that this was a lost opportunity. After all, I have these two obedient sluts together, there just HAS to be some potential for mischief! In time, I started thinking about concrete ways I could have them interact in service to me. I know Benny would love to spank Xavier, but I need to be certain that there is no bitterness or resentment behind it. I’m a firm believer that discipline needs to come from a place of love.

And poor Benny, what an ass! He’s really painted himself into a corner. See, I am the only person he has played with for some three years now, and even though I have told him repeatedly that I am OK with him playing with someone else (particularly if it’s one of my buds such as Mistress Park, Mistress Betty or Mistress Sage) he says he just wants to reserve this part of himself for me. Frankly, I appreciate the loyalty, and now that I own his pecker, it seems even more appropriate. So as far as I’m concerned, it’s all good. Still, there are a few issues. Benny has trouble going to events now, for instance. I’m reluctant to invite him to go with us because I know it will put Xavier in a snit. Meanwhile, Benny’s good friend Mistress Helen won’t go with him, telling Benny that since he won’t play with her, why the hell should she? How’s that for friendship!? His buddy Mistress Summer would do it except she hates events, always telling Benny to forget that shit and come to JohnnyFrank’s bar for a few pops instead. Ditto Mistress Carter who hates gatherings of any sort. Well, in conversation a while ago, Benny told me he feel like a fucking loser showing up at events by himself, hoping someone like Mistress Betty will be there to talk to him. Failing that, he feels like il est arrivé comme le cheveu dan la soupe. Ha! Such a great expression…have to hand it to the French. But that’s his fucking problem - it’s all in his head, anyway; he’s advertised himself as not needy, so prove it, pal. Just fucking show up and I’ll be glad to share 2-3 minutes of my time with you. Hahahaha!

At any rate last Thursday we all experienced a breakthrough of sorts. Phew, so unexpected! Benny came over at my command to be unlocked after his two-day confinement. I was thinking as he was on his way over that it was time to change to a 4/2 set up: four days in chastity and 2 days of freedom, but kind of forgot about it when Benny arrived. I had a date that evening with my friend Mistress Park, and uncharacteristically Xavier was there on a Thursday to clean my apartment. I wanted to get this over with quickly. But after unlocking Benny, something got into me. Was the moon full? Instead of his usual 3-minute climax, I spontaneously started strangling him. I tied him into a most uncomfortable position and whipped him lustily. I spat on him, attached forceps to his nipples, walked on him and caned him with the rawhide cane he gave me a while ago. Must have been something in the air! I tethered the forceps handles to a stationary object so that the slightest upper body movement would be excruciating. Deep red, double-lined welts appeared on his ass, which only spurred me on to whip harder, with more focus, with more desire and with sadistic intent. Benny was unable to use his safe word, inasmuch as I have taken away his right to a safe word when he is in my residence. The only limits under my roof are my own. As it should be. Benny was now way over his limit and was softly sobbing as he took my punishment. Crying is a tricky thing with him, so I was really happy to get there. Meanwhile, kneeling Xavier took in the whole scene with an awestruck look on his face, and his trademark clincher around the waist (this time with a feather-duster and other cleaning implements attached, as he was there to clean) . Recently I had decided that his improved behavior warranted being allowed to watch these scenes, instead of being exiled into a corner with a morose expression. He seemed a bit lost on this particular evening, to be honest, but I’m certain that this single reality did not escape his attention: Benny was receiving the sort of sadistic treatment that Xavier could never tolerate, something which I’m sure gave Xavier pause. After all, where it not for Benny, it could have been him on the receiving end of all this.

Well, I’m in such a kinky mood by now that I’m thinking ‘money shot’. Why not have Benny cum in Xavier’s face? Oh, hell, I knew that it was something we had not previously discussed, but so fucking what? It was a spontaneous idea and I am a creative Mistress! Wow, what a rush - I felt like a porn producer with all the pieces at my disposal. I had Xavier kneel in position while I tortured Benny and compelled him to jerk off. Xavier was a foot away…money shot!! But then all my best laid plans began to unravel. Benny inched closer and seemed ready. He was softly sobbing. Just as I was about to order a pop shot, Benny reached out and sweetly caressed Xavier’s shoulder. Then he cradled the back of Xavier’s head, gently and lovingly pulled it toward him, firmly but slowly. He stopped stroking and softly pressing the crown of his dick into Xavier’s mouth (just up to his frenum), carefully directing it in. He gently cupped his enormous hands around Xavier’s jaw line and gently caressed his cheeks. Then, he sweetly ejaculated in Xavier’s mouth.

Well hell, I had no fucking idea what to do, the whole thing having been such a shock. I was stunned. In the aftermath, Benny immediately fell to his knees and started doing his worship thing. OK, fine. With what must have been a slack-jawed expression of disbelief, I hugged Xavier, mostly because I didn’t know what else to do, and he looked like he needed a hug. I was also momentarily disappointed; that wasn’t exactly the pop shot I had in mind, and it seemed like I had lost ultimate control of the scene. But I had to admit, it was very hot! There was absolutely no denying it…

Training my subjects

I do love him so. Well, in a way.

Let me introduce myself, I am Lucy Cunningham, lifestyle Domme, writer and lesbian...sort of. The truth is that I have “sex” with women and play BDSM games with boys. Pansexual, you might call it. To me the BDSM games are highly sexual, certainly in the mental sphere, so in that sense I am bi, but it seems the world at large does not consider BDSM to be sex. Whatever.

Let me tell you about my friend Benny. Benny is straight, but in fact lost interest in straight sex long ago. He expresses himself as a masochist who revels in having beautiful women hurt him. He is not a submissive per se, but he does submit to me – completely, and without reservation. His obeisance to me is all-encompassing; he will do absolutely anything for me. His gift of subservience is truly special to me. I do not avail myself of his services often, but it gratifies me to know they are always available. You see, I am a sadist. I need people like Benny to feed my fire. My job is to take him and his ilk on a guided tour. A tour of their pain, their limits and their suffering. Benny is such a dear. Truly the only thing he has ever asked for is to suffer for me. Such a good pet.

And, well, Benny is not my only guy friend; in fact he is not even my favorite. My favorite is Xavier. Ah, just a young lad: when I was his current age, he was just a tot of eight years. When I first met him he seemed a just bit sappy, replete with a moist, limp handshake and a halting, painfully shy way of being. Well, underneath this almost pathetic patina is a rapier-like wit and wisdom beyond his years. Indeed I am a specialist in looking beyond the envelopes of people and truly understanding and appreciating their true essence, like looking through the ice of a clear blue frozen New England lake and not seeing the pock marks on the surface, but seeing the fish and fauna below. I love that. I love the complexity of the creative mind. Xavier has truly progressed under my tutelage. Let’s face it, a lad in his early twenties has not had enough time to really have a string of accomplishments, but within the narrow context of these still formative years (what bullshit, by the way, all years are formative) he has grown exponentially and according to the strict specifications I have laid out for him. It is such a privilege to be here at this point in time and able to provide expert guidance to this youngster. See, after my own two marriages…well fuck that…that’s none of your fucking business.

But maybe that’s where Benny comes in. He’s older than me and has had two marriages of his own, with mega-alimony and all the other accompanying issues. He also fashions himself as a writer. Not at my lofty level, mind you, but his chatty style does amuse me. My goal for this year is to wean him from his childish addiction to points of suspension. Jesus, that annoys me! He thinks it helps him replicate the rhythm and pacing of actual conversations, but to me it shows the inherent limitation of his prose. And, well, he’s not exactly George Cluny, though as I always tell my friends, I have my preferences and I have my priorities. Benny’s ability to perform many technical feats somewhat offsets his limited envelope. Meanwhile, I am deeply attracted to Xavier’s slim waist, full head of hair and pale skin. A contrast between these two sluts, indeed.

Anyway, is my plate ever full these days. Training Xavier full time is a job all to itself, but Benny has applied to be my chastity slave and I accepted. Sometimes I wonder if that was the right decision, because I know once we have all the Indians lined up, this is going to take some of my precious time, but Benny really does amuse me and the thought of exploring this with him just sounded too delicious. One practical problem, which I have still not worked out, is how Xavier and Benny will interact with one another. The only way I can do justice to Benny’s training is to occasionally work them together. Benny has told me that training with other men is not an issue; he has had his ball sack tied to the ball sack of another slave, for example. For Benny, it is all about the focus on me – as long as I mentally control him, the physicality can go in a number of directions. Xavier, meanwhile, is not exactly brimming with confidence (something I am working on) and Benny can really be a pain in the ass, which frightens Xavier. One of the features I liked about Benny, aside from his total devotion to me, was his seeming lack of neediness. But recently there was an episode at a club that disturbed me. I went with the two boys and was proud of both of them – they really behaved well. But since I had spent some time early in the evening playing with Benny, I felt I had to give Xavier my undivided attention toward the end of the night. This meant ignoring Benny for the last 2 hours. Well, I didn’t exactly ignore him…I had him watch my bag for most of that time. I really wasn’t thinking straight: if I had forced Benny to his knees, tethered him in place, and congratulated him with a pat on the head (and maybe allowing a kiss on the toes) he would have been the happiest man in the room. But I was so focused on Xavier’s needs, and frankly my own desires at that moment, that I kind of spaced on Benny. Besides, the room was filled with his friends (though he told me later all of the ones he really likes had left early) so I never gave it a second thought until the rat-bastard skulked out like a confused dog, without saying goodbye. He was apologetic enough the day after, and *yawn* he seems to want to discuss it with me now, but it really fucking irritated me. And now that I really reflect on it, there was a general nervousness that pervaded the entire evening that really gives me pause.

Still, all this got me to thinking. I’m the kind of woman who is always looking to turn negatives into positives, especially when the negatives are the weaknesses of my boys. Benny confided to me a while ago that his devotion to me is now so strong that he will be willing to do anything (his emphasis) for me. Hmmm. I asked about his limits and his safeword. He surprised me by saying that at the end of the day his only hard limits are FT and submitting to male Doms. Well, that and drinking while lying down, which could cause him to choke to death because of his apnea, but that’s a health issue. All his other limits, says he, are soft and can be broken down given the right methodology. As long as the exercise is designed to please me, and he is allowed to focus mentally on me while it is happening, then he is down with it. Benny’s not a “microwave” kind of guy, he needs to be maneuvered into the right position over time, in an atmosphere of love and confidence. He’s constantly referencing bullshit like “ the right vibe” which sounds so annoyingly new-agey to me, but in truth, I do know what he means. The interesting thing about these two subjects is that Xavier is a sissy slut and poseur, whereas Benny is a pain and service slut. Wow, I thought, these two subjects really do compliment each other…you know, ying and yang, and all that horseshit.

So my project for the summer and fall is to see where I can take these sluts. Both give fabulous dildo blow jobs and Xavier especially can take it up the ass like a champ. Benny, as usual, has his own issues. The initial penetration is difficult, but once achieved, he can be fucked like a $50 hooker. Benny told me a long time ago that torturing other men in a non-sexual atmosphere was one of his fantasies, but that sort of thing is not what I want for Xavier. Still, the potential of bringing these two to another plane is too delicious to not think about…

Crate Trained

“Oh, the poor dear has been in there for 4 hours! I almost forgot!”

I could hear Mistress Anna’s cackling words, dripping with sarcasm, from the other end of the apartment. Indeed I had been in her crate for some 4 hours, but I was strangely content. Mistress Anna began crate training me almost six months ago, and in that time our friendship and my mental frame of mind in general has undergone a vital transformation.

It all began rather innocently enough, with me offering my cock up (pun intended) for chastity play. We began the process very slowly, first with me getting a piercing (a frenum) intended to secure the chastity device. Then, after patiently waiting for the piercing to heal, I selected a device that I felt I could wear long term. I always joke that I’m built like a fire hydrant, and there is more than a little truth in that statement. My cock follows along with the rest of my body, and while not remarkably long (especially when flaccid; I’m a grower, not a shower, as the old line goes) my cock is v-e-r-y wide by any measure. In fact, the diameter of my cock is at least 1 ¾ inches, actually, let’s call it 2 inches to be safe, really, whereas the default inner width of most commercially available chastity tubes is 1 ⅜ inches. Not a chance. Even flaccid I cannot cram my member into one of these contraptions. So finding the right piece was crucial; I’m not going to wear something that chafes me, cuts off my circulation or is an all-round pain in the dick…literally and figuratively. Unfortunately, frequently good things come with a price, and for a while there dumping upwards of $2,000 on a chastity tube was not in the cards, as I was involved in intense business negotiations that were temporarily tying up my assets. Don’t get me started on that nightmare. Jeeesh! Suffice it to say that when the negotiations were over and I had finally won my freedom, it felt as though a 1,000 pound weight had been removed from my shoulders; but I digress. We were talking about chastity devices. I finally settled on a polished stainless steel tube made by a group in Montreal. Their general design had to be modified, as the prototype is typically secured by a Prince Albert. Indeed, I want to use a PA eventually, but not as a locking device. I love the look of a PA but I want to have the freedom to take it out whenever I need to, while at the same time the tube remains locked down. So the frenum lock with a more or less decorative PA really works for me. I was careful to have the tube was designed with this future feature in mind, and my favorite piercer is geared up to make it a reality.

Once all the practical issues were finally resolved, Mistress Anna and I worked out a training schedule. I was very concerned going into this but not because I was worried about not being able to rub one out whenever I felt like it. On the contrary, veterans of this sort of play have all told me that the problem is they spend every waking moment thinking of ways they could serve their Key Holder. In many cases this is no problem, as the Key Holder is a live-in partner or at least is someone who is seen regularly. My relationship with Mistress Anna was very different. She is very busy with a vanilla career, at least two subs who are higher up on the food chain than me, studies at a local college and an active social life. On the one hand, we have bonded on a myriad of subjects and on many levels have gotten to know each other quite well. On the other hand, sometimes weeks and in a couple of cases even months would go by without me seeing her. These periods were sometimes nicely filled in by electronic communications, but other times they would pass like wisps of air; with no mention or remorse. Well, chastity training calls for something else entirely. The first few times one is locked up are almost controlled experiments, with the Key Holder not too far away, offering mental reassurance and the ability to unlock the device in case of emergency. It was hard for me to see exactly how this project was going to get of the ground; the tremendous mental connection Mistress Anna and I had forged was really not in play here. Certainly in the middle and later stages of chastity training it is all about the mental aspect, but at the beginning, there is simply no substitute for physical presence. Not to mention that I already think constantly about ways I could be of use to Mistress Anna; if I did it any more, and without being able to act out on these thoughts, I would surely go insane.

Enter, in the role of angel and wise council, our friend Mistress Summer who happily offered her experience and expertise in these sorts of matters. First, Mistress Summer warned me to not embark on chastity training unless a “contract” has been executed, one that details how the initial stages of training were to be conducted – by both parties. Great advice. As with anything else, communications is the crucial element, and once this matter was fully aired and discussed, everything else fell into place. Mistress Anna at first had to work hard to come up with enough things for me to do for her. This may seem counter-intuitive, after all, I was offering up my services and considerable expertise for free…and I really do know how to do a lot of shit. But opening up her spirit to another human subject in this way was not easy. Eventually, she allowed me to cook for her and stock her refrigerator and pantry with meals she could re-heat. That was a start. Then I was allowed to construct a built-in cabinet for her apartment. All the while Mistress Anna continued to give me writing assignments and other mental chores.

Finally, one fine day, she asked me to build her a crate…the sort of crate pet owners use to train their puppies, only large enough for a human. The crate, she explained, was to fit into a corner of her small apartment, so two of the sides were to be solid, with two sides “open”; that is to say, with bars a couple of inches apart. Mistress Anna grew quite animated as she discussed the plans for her crate. She required a water bottle outfitted with a teat to be sucked on when the confined person needed hydration. Similarly, a hook-up to allow catheterization would be needed for particularly long confinements. The only question, which remained unanswered, is whether the collected fluids would be fed back to the ‘inmate’ via the water bottle. Finally, an electrical hook-up would be needed for laptops, PES units, C-PAPs, and so forth. Left unstated was who the crate was intended for, and I did not ask, assuming that it would be used to detain subjects more worthy than myself. Even at this point, and despite how close we had become intellectually, Mistress Anna was careful to keep me at arm’s length, and insure that her real intentions remained enigmatic. I happily constructed the crate for her, building 6 modules in my workshop, to be assembled on-site. When the cutting and sanding and drilling and staining and sealing were accomplished, I brought the pieces to her apartment for final assembly. I was delighted to see that she had purchased a sort of futon with duvet cover to go inside the crate, and the fit was perfect. Once assembled and secured in to the assigned corner of her bedroom, Mistress Anna marveled at the solid construction and the fierce look of the piece. “Well pet, I have a variety of uses for this fine piece of furniture you built me, but one of the principal uses is to have a place to keep you when you are in my home. When you have been given an assignment to accomplish or when we are playing, of course, I know exactly where you are. But other times, I need to know you are safe and out of danger. For that purpose, having My cock locked up is not enough. I need you to be in total lockdown”.

Well, since that time, my visits to Mistress Anna’s home have become a bit more frequent. Almost every time I spend at least part of my visit in her crate, being trained like a puppy. Many times Mistress Anna will combine the confinement with some intense torture. Her favorite is to have an appliance on the exterior of the crate, such as a mini bar holding two serrated nipple clamps. In this set-up the mini-bar rests outside the bars of the crate, while the clamps reach in to squeeze my nipples. The delicious pain of the clamps is multiplied by the awkward physical position the appliance requires me to maintain. Sometimes she uses her PES unit with sound attachments. Other times she will simply attach the chastity device to one of the bars on the side of the crate. In each case, Mistress Anna will issue instructions, admonishments and goals to be considered while in confinement.


To be continued.