Anal Training – The Approach

I was asked to revisit this by a few specifically to share any additional nuances I have for the approaches I employ for training a sub in the art (and more importantly, the enjoyment) of Anal Training.

In this post I will be sharing the framework for Anal Training, from the tightest and most frightened of virgin anuses to the most decadent and masochistic lovers of anal abuse.

I will admit that this particular post has been in draft form for many months and has had many revisions and it is just now that it is nearing completion. It is being completed this evening as, previous recorded in this blog, Wicked Daddy is a HUGE proponent of the “Change Up” – building a pattern between a Dom and Sub and then changing so unexpectedly for the increased results. The change up tonight was feedback from a participant in the early rounds of the HeavyWeight Challenge (The FULL CORE set of Anal Plugs I will be unleashing to the masses). It was around the Heaviest of plugs – and around this subs focus being always slanted towards “Over-Eagerness” towards a shade of color and emotion when finally graduated to the largest 1 lb plug and having it deployed for greater than 12 hours.

Well well well – Wicked Daddy takes on change up as much as he gives – so presently – WD is in the 14th hour of wearing his own personal 1 lb. plug. It is only fair to do so in order to give an accurate reply. Let’s start with that before the Schedule/Planning details.

Recap if you haven’t been following every aspect of this blog – Wicked Daddy himself started off at a fairly young age as a fully dedicated submissive to an amazing teacher and dom. I owe this amazing person so terribly much for the joys brought into my life in the understandings of these amazing dynamics as well as being centered and in love with myself first and foremost. 

I am far past any hesitation or even basic titillation at the insertion of anything inside of me (A few thousand of these experiences in a lifetime unfortunately does that to someone). I do however still recognize the immense value for a sub around the mystique, ritual, and formality of that particular experience. For today I properly lubed my device and the insertion point (Organic Coconut oil – a staple to be certain) and still tried to employ something less direct as simply plugging it in. I instead placed it on a surface and kneeled over it, and, as had been instructed to me 30 years before, showed my willingness to the device and instruction as to lower my bum on top of it and perform the indelicate act of bouncing on it until I was able to achieve full penetration and insertion to it’s hilt. (I do challenge all readers to try this. It IS a skill I assure you – both to not topple the device as well as to force the bouncing and lowering to a point where you can force the full insertion). I did so – and remembered the hours in my life previously spent to learn such a “demonstration” to my Dom/Master. (Like riding a bike without a seat cushion I thought – and chuckled).

The day progressed as normal – a few errands (Post Office, Grocery Store, Hardware Store <Why ALWAYS the Hardware store? lol>). And here are my observances.

While wearing such a heavy plug – I definitively slinked more – and yes – sexually as a Dom would expect of this sub (especially female). When you wear a lightweight plug you can 30% fake it – and the discomfort can be pushed through. Wear a 1 lb. plug with girth? no – you are rotating your hips like a runway model most of the time. (I did notice a relatively attractive and athletic ebony skinned gentleman glaring at me with a smile more than 3 times, lol).

The added – and likely more pronounced recognition – was acknowledgement of the lack of tightening of my anus – despite the pull. This was a phenomenal reminder of the purpose of such a tool, especially the heavy full core set.  I, albeit heavily trained previously, immediately recognized the struggle between the reflex to tighten and the desired and inevitable result of being relaxed. For myself – this was the constant “twang” that resonated most. I personally know you cannot fight the pull of it – it isn’t until you are trained to relax and accept that pulling does it feel, well, blissful. Prolonged wearing of this will do that to a sub – relaxing those muscles to accept – well you know, and whenever it is called upon. I am going to appease my legal team right now and say “I make ZERO MEDICAL CLAIMS REGARDING THE USE OF ANY ANAL PLUGS. DO SO AT YOUR OWN RISK, and MY OPINIONS EXPRESSED HERE ARE MINE AND MINE ALONE AND IN NO WAY ADVOCATE ANYONE ANYWHERE EVER USING AN ANAL PLUG MUCH LESS EVER OBTAINING ANY JOY FROM DOING SO. STAY IN SCHOOL, DRUGS ARE BAD.”.  Oh I am so going to enjoy my call with the lawyers on Monday after that one lol.  But for my own personal reality – I was relaxed – I felt the pull – it was constant – and like the feedback from the HeavyWeight Challenge participant – it did – it felt like a colored lens on the word (For me a happy colored lens) and yes – I could recognize – the eagerness of having my anus used. Okay, not just “used” but “USED“, the type of used where you naturally add an “AB” in front of it as assumed.

Side Note: I want ten more 2 or 2+ loving Dom/Sub partnerships to join the HeavyWeight Challenge. I will greatly discount a set of the HeavyWeight plugs (plus throw in some gifts). Requirements to be considered? You must already have used or employ anal plugs in your dynamic regularly (I want to know you will experience the difference with these) and that you are willing to write to me about your experiences and allow me to publish parts or all of your feedback. Email WickedDaddy@WickedDaddyAcademy.com with the subject like of “HeavyWeight Challenge” for consideration – and tell me why you want to try this.

Onto techniques…

I’ve expressed it a few times before – every sub is different. I will add, every anus is different as well. In my personal opinion, every anus will be more constricted by the life experiences and personal perceptions of the sub and “the part where poop comes out” than the physical limitations or capabilities of such. Butt (Two “T”s, see what I did there?) that is also a bit of the fun of it too.

Here are the first and more important nuances of the logistics of first encounter anal training.

Position. It is critical to have no muscles that can contract. On all fours, spread the knees as far as possible. You MUST achieve less than half a foot from the anus to the floor. Only in that position can all the contracting and opposing muscles be in a position where the insertion has least resistance. If your sub is physically incapable, then on their side they must be, knee pressing the floor bent and up as close to their chin as possible, other leg held high by your hand, preferably by the ankle (with knee also at least slightly bent).

Mental Association. Especially for any sub with any qualms or pre-built societal notions of negativity to anal. Stimuli to vagina first. Get a good solid build up before slipping even the pinky into the “tender starfish”

Gradual. Like the tortoise – slow and steady wins the race. Your goal as sub it to move SLOWER than your sub wants. Build the anticipation. Watch for their hips to pulse and swivel craving deeper penetration. Tiny circles around the edges, tip toe insertions, gradual fingering, slow plunging with slow deliberate paces. Watch for the breathing to increase, the pulse to race, and their body to twitch to gain greater penetration.

If the mind is hesitant, so will be the body. Employ patterns (as written of before), employ word association games (as written of before), or find any mechanism where you can force the subs thinking to align with the actions. A new one to add to the list of techniques. Math. (Oh you don’t think math is sexy? Fuck you – and try this). Take your middle finger and dissect it mentally into four parts. 1 is 25%, 4 is 100%. Now ask your sub, “What is 1+0?” – answer “1” – dip finger into anus 25%. “What is 2-1”, answer “1”, dip finger in 25%. “What is 3-2?”, answer “1”, dip finger in 25%. “What is 1+1”, answer “2”, dip finger in 50%. “What is 3-1?” answer “2”, Dip finger in 50%? Do this for multiple combinations of 1-4. Do it 30 times. Now ask your sub “Pick a number between one and four?” – Then comply. Reply with “Again, Pick 1-4.”, comply, then “Again.” and comply. Repeat adnauseum, and enjoy.

Daily Training:

The first few days should always be Dom controlled, especially for the uninitiated or those with bad previous anal experiences (too many of those I say). This is set aside time (20-30 minutes, no more) when anal penetration and practice will be directed by the dom. WD still strongly suggest that these initial days start with vaginal manipulation to build that mental connection or pleasure with “The unholy” lol. Depending on your sub, this is still finger play. Extra extra lubrication for the best experience. Anal beads, sure. Basic toys, okay depending on your sub. Way too many variables to say where your sub falls within a given single post – so you will have to judge based upon them. The goal of each session (in my mind) is – make them Purr, and leave them wanting more.

Transition to next level – depending on your sub – daily anal rituals, usage of daily plugs, or even them taking over and performing anal stimulation for their Doms pleasure of viewing is a typical next step. (Oh boy are Wicked Daddy’s Glass Rods of Training great for all of these stages – shameless product plug <see what I did there? lol>). The key for the second stage is adoption into routine. Continual building of the desire, and if need be continued reinforcement of the pleasure with added vaginal stimulation if the “craving” hasn’t fully been realized. For myself, this is a denial phase. Denial of my subs built up wants of MORE anal to me withholding (as well as likely my own denial to simple take what will be mine). Patience. Definitely Patience.

Third Level – Earning first Penetration. This is  Wicked Daddy thing – it’s not for all. But WD finds a certain perverse pleasure and joy in stage three, especially for the subs who had any pre-conceived hesitation or limits to anal. I, set a bar and make them earn “the privilege” of finally getting penetration from WD. Whether the goal is giving WD ten reasons why they want hard warm cock in their bum to demonstrating X number of hours with WD’s Glass Rod # 3, there is a definitive hurdle to be jumped and a definitive subjectivity to WD accepting that such a hurdle had been met. From 2 full days with the 1lb heavyweight plug to “Look Daddy I can hold a cucumber there for 10 minutes without flinching”, it is an achievement that must be earned.

When final penetration is “Earned” – it is not included in training. Wicked Daddy schedules it hours ahead of time. I set the expectations, I build the formality and the pomp and circumstance of it. I use words of “Final and full delivery of you giving all of your holes for Master/Sir/Daddy”. There is also one other technique I will share now. It is one that surpasses concepts and hits and the core. The core that the sub has FULLY given ALL holes for ownership of their Dom.  This is the first insertion and release from the dom. (Not applicable to the fully anal initiated, but in reality that is the least of you possibly reading this). If you are the sub – do NOT read – and hand this to your dom.

First penetration and anal release from the Dom within the sub for practiced and trained anal should be methodical. You are still checking for tolerances, you are still cognoscente of fears and safe words, their care and joy is still more paramount in your mind than anything else. If they are overly nervous, stay steady and fast and demand they control the depth and pace of penetration through their own body’s movement against your cock. When you feel they want more, you can ask “Do you want Master/Sir/Daddy to lead you?”. I find a hard fist of hair and a slow mid-insertion penetration to be most fulfilling for a sub, with the gradual deeper thrusting to check for the desired results. Now here is a magical tip – one that I have found really binds the sub and dom when good anal prep and training has been done. Post release – do not remove yourself from your sub’s hole. Use that moment to ask the right questions of servitude. Things like “Do you find fulfillment in giving Master/Sir/Dom all of you now?”, “Are you fulfilled knowing you now fully belong to Master/Sir/Dom?”, or “Are you now in full recognition that Master/Sir/Daddy FULLY owns you?”.  Assuming positive answers – and knowing still that your sub has achieved a milestone – one that your were careful with and maybe even gentle with – give that sub one more treat. Go at them again – but this time less gentle. My last time doing this the words from my mouth when I asked her “Do you now feel like you are FULLY owned by Daddy and that he has complete dominance over you?”. Her reply was “Yes Daddy, I am proud of myself for this”. I gave her a “Good Girl, because Daddy isn’t done with you” and gave her a good and much harder riding afterwards. Oh her bliss and moans of joy still bellow in my ears (as well as her blushes and comments of joyful soreness for the next two days).

Of the already anally initiated –

Much different approaches – especially if they already know the joys of anal “orgasms”, and even more so if they are simply masochistic and want deliverance of painful pounding.

I personally have a hard time of writing of degradation. That is simply NOT me, although I clearly recognize those that need that and have employed such well beyond my own comfort zones for the enjoyment of the sub needing it. I wont be writing of technique of degradation here (I am certain there are other blogs good for that) but will include some elements for some subs desiring so (and the Doms wishing to give such for their subs joys).

Lubrication – I have wrote of this technique before. Lube your sub as you would a real doll, or appliance. Go over board in this preparation. It fulfills many of their needs for being “used” as such.

Initial Stretching – Apply just a bit more. Start with two fingers instead of one. Employ double penetration between the vagina and anus as an alternating counter balance. When one is starting to feel (you will know from your subs auditory and visual cues) that it is getting very well stimulated – alternate to the other. A bit of aggressive pace and movement can likely be easily employed. If I were to set a goal for you as the Dom, it is to go from one to the other build up to potential release then alternate, and keep doing do until both can release together.

Pain is pleasure, Pleasure is pain. Also written of before, orgasm and sensations of sexual pleasure can be delayed or postponed with the introduction of pain. Spanking, clothesline pins on fleshy parts, nipple clamps, low temperature burning wax, and hair pulling all fit the bill. If your sub is Anal initiated and wants the full experience – hold YOUR penetration until every aspect of the subs body is ready to pop with fulfillment. If they release before you achieve this – the time to build it back up is less than a third. Make it an experience they will remember just from walking or sitting the next day. It is okay.

I enjoyed completing this tonight – even if there were a few areas I wanted to flesh out a bit more. I look forward to any questions or comments, and “Happy Anal to all, and to all a good night”.