This is a fascinating development, and I’ve really enjoyed following your adventures over the past months. I’m afraid this one’s out of my circle of knowledge, but I really hope some other readers will comment with their opinions/advice. Good luck!

Mmmm…thoughtful, measured, BDSM…sounds like a tremendous idea. Lots of fun can be had with this new aspect, and it sounds like a very promising twist on your already very liberating relationship! There is nothing more rewarding for me than connecting with someone else on a level that allows such wants and desires not only to be expressed but encouraged and brought to life.

She is undoubtedly a remarkable woman and you, my friend, are one very lucky bastard. I like how you are affording her the level of care and respect that she deserves by being so thoughtful and in removing her from anyone else’s agenda (unless and until she actually wants a different hand on the tiller of this particular type of ship).

I am no Master, but I have given it a lot of thought and study, and do have experience which is along the lines of what you suggest, so I do feel qualified to at least share some of my own thoughts, impressions and experiences with D/s and lighter (but by no means not intense) BDSM.

D/s requires a fair bit of thought not just about what to do by why – to what purpose and end. You can pick up most of the how by watching some porn or reading erotic literature (even Mr. Grey’s exploits do detail a few choice moves), but the why is much harder to discern, much less talked about/shared. The why needs to be understood (at least implicitly and by you) so that you are thoughtful and deliberate in your attempts and in order for those efforts to have the highest chance of hitting the proverbial target with your lady.

So lets start with what I do know – though I am physically tall and strong, I do not project myself in a particularly rough or overly aggressive physical way. I am also not boisterous or gruff or a particularly “domineering” personality. For ages, I thought that those things were important. What I can say is this – unless you lady is really looking for a highly specific experience with a visual of a particular flavor that you are simply not physically capable of filling, than this impression is simply missing the point entirely. What matters most is your approach and your understanding, not on your experience level or competence with what specifically you plan on doing.

Why are you doing whatever it is that you plan on doing? How is it contributing to her overall arousal and experience? At this point in my life I do have very strong feelings and expectations of what I want both me and my partner to feel and experience, why I want them (what does it contribute to the experience – part of a continuum of sensations that builds to something else, introduce variety, playful novelty, something unexpected or out of character, etc.), and some concept of the best way to experience and enjoy them (call it part of my life long quest of a sensualist to study and imagine and learn these things from others).

It is my “vision” of how to maximize the enjoyment of sex and sexuality in all of its varieties and variations and flavors. I have not done everything I have seen or know of or even those things intend to do, but I do know how each one of them introduces a new element a new dimension and that if done with confidence, and creativity and with an open mind and a healthy dose of playfulness and a partner who adores you and is willing to follow your vision, that you can make that “Vision” are reality. Even though there is a give and take and negotiation around the roles and ground rules, you are already well into a D/s journey -one with one party (you) expressing a “vision” of what your sexual relationship could be, the other (her) opening herself up to such a possibility and contributing (or finally admitting) her own desires and fantasies, and then leaving it in your hands to execute (at least for now).

In terms of your approach, you should focus on the goal and not be not overly focused on how you plan on getting there. So what is your goal? The goal is simple – to introduce a number of increasingly stronger physical sensations with the idea that the purpose of the painful ones is to induce a physiological reaction (increased heart-rate, shortness of breath, muscle tension, tears, flush of blood, release of endorphins and adrenaline, etc.). For better or worse, the physiological reactions to pain are inherently sexually arousing – or at the very least are the building blocks to sexual arousal. Combining these acts with soft, tender pleasurable sensations – even explicitly sexual ones – and the mind quickly becomes overloaded from all the intense inputs – inducing a of confusion as to what is going to come next. That is why taking your time and repeating patterns and cycles are so important because they give the mind something to grab onto and make sense of – and know when to expect the next dose of pleasure.

Oh, and that is just the physical part…layered throughout the whole experience is whatever else you can bring to the table from a mental and emotional perspective. Whatever would be unexpected, or provocative, or difficult or embarrassing to answer when confused and in a compromising position, or plays on some of her fears or shameful thoughts (seems like a great time to insert a butt plug and comment on her virgin ass if she is sensitive or embarrassed by the notion of anal play -and there is nothing like threatening (or announcing your intent) to fuck her in the ass when she is firmly tied up and unable to move or resist).

Next, show her that you care, that you understand that what you are doing is intense (in both a good and bad way), that this is what she asked for and you intend to give her that experience to the fullest – encourage her to continue and remind her why – and show her that you ARE empathetic and care about her as you are doing it…even if that means you still intend to continue on or increase the intensity (obviously you need to set some ground rules for safe words or other signals before you even begin and follow them accordingly). Tell her how much you love her for being so brave, tell her how excited it makes you to see her like this, tell her how proud you are of how strong she is, tell her how beautiful she looks tied up like that…how wet and swollen her pussy is…tell her to let herself go, that she is allowed to cry…to not hold anything in or back, encourage her to give in to the range of feelings and emotions that are coursing through her… basically that you are there for her not only now but after this is all over as well…

Finally, why is she doing this? Is she a masochist? That would be a perfectly acceptable answer and there would really be no role play necessary other than the fact that you really have to play the part and match her intensity with an attitude of your own that says you won’t stop unless and until she uses her safe word, and that you will not have much more than feigned feelings of empathy (you should really be playing up the notion that you will be testing her boundries (and at least threaten to cross over your pre-arranged rules or limits).

If she is not a masochist, you could also introduce the role play element… Why must she endure this? Was she a naughty school girl, did she piss you off with her driving on the highway, was she insolent and insulting to you in front of your friends????

Each of these layers adds to the intense physical confusion she is already experiencing, provides more information and feelings to further overload her rational mind (it is already working overtime to process and categorize these intense physical sensations with the onslaught of unusual and unexpected reactions). Mix each of the following acts up and try to form a pattern which does repeat even if it does get more intense:

short sharp physical pain (spank on her ass)
mild physical pleasure,
gentle caring words,
longer duller pain (pinch or twist her nipples)
provocotive statemtents (your nipples are really red and hard, your cunt is really swollen and wet, I can see your pretty asshole puckered up tight, you look like such a slut tied up with your pussy exposed so anyone could fuck you, what if I left you here tied up like this for a few hours and went to a bar to have a drink),
simple question – Is this what you want me to do to you?
hard question – Do you like my finger in your ass? Would you like me to fuck you up the ass right now?
provocative question – What if we were in a hotel and I ordered room service with you looking like this? If I left you tied up here and went to a bar would you be concerned that I might bring someone home with me? Would you ever want to be fucked like this by a complete stranger?

Pick a pattern and repeat over and over again. With any luck you will get her rational mind to retreat much further than through ordinary sex. If you are really lucky, you may help get her mind to shut down entirely. At that point she will be all physical and emotional which is a very raw, very vulnerable, very intense place to be with very few defenses left – a truly beautiful sight especially with someone who you care so much about. One where every anxiety and fear and shortcoming as a woman, wife, mother, daughter, lover/partner will be right there on the surface. Expect lots of tears, uncontrollable guttural sobbing, and screams of intense feeling. Don’t take it past that point for now.

Lastly, you should approach every aspect with supreme confidence. Confidence, that you understand and accept why she wants to explore this side of her sexuality. Confidence in knowing that how you get there matters much less than the notion that you WILL get her there if she opens herself up to allowing it to really progress. Confident because you have come prepared with a seemingly endless supply of ideas and options for how to get there – some physical, some verbal, some with impliments and devices, some with nothing but your hands, some playful, some serious, and everything with the objective of being anything but plain and ordinary and like you would do to her when not in this intense space (other than those things that bring her the most immediate and intense pleasure which are great to know as a contrast to your more intense moments of pain).

So with a clear goal, an open mind, hopefully, new found confidence that there is no real mystery to satisfying this want and desire of hers, and a steeled resolve that you are going to inflict pain – possibly lots of it (don’t go leaving marks, but the notion that she cant sit comfortably for a few days isn’t that outrageous) – and are prepared to do so come hell or high water (or hearing her safeword). Imagine it is just like getting your kids to swallow that bitter pill, its hard, but you aren’t going to take no for an answer…

Just remember, this is really about HER trusting you enough to even share such thoughts much less allow you to act them out. My own experience is that the “thoughful” “psychological” approach to D/s is in short supply but infinitely fascinating. Trust your vision not some so called Master and honor and respect the trust she is giving to you.

Oh, and let us know how it goes…

In case I wasn’t perfectly clear in my original post, I am no sadist. I am a lover not a fighter and I don’t totally get the pain thing – maybe I have just never really had the desire or willingness to go there or a partner able to expertly wield the whip – but I do know for certain that everyones reactions to pain are different. Not knowing you or her, I would add the following color/background to help you understand why exploring this may be an important opportunity for both of you and to help you get comfortable with the notion that the act of you inflicting pain (despite your expressed reluctance to do so to any great degree) may be perceived, received, and processed completely differently by your partner. In fact it may lead them to a wonderfully rewarding place at the hand (no pun intended) of someone (maybe the only person in their life or ever) that they trust enough to cede control of any aspect of their life! “Feeling” in this way, may finally give them the space and opportunity to relax and let go of the obligations and responsibilities that perpetually haunt them.

You say that she is a composed, in control person in her daily life. People like that are often so measured and controlled that they don’t allow themselves to get out of control, in fact, they are trained/conditioned stay in control almost at all costs and will do/endure almost anything to hold on to the reins (personal sacrifice of time, physical and emotional well being, never allowing a personal issue or illness to come before taking care of other responsibilities or other people in their life). Being in control all the time (or feeling the overwhelming need to be in control) is a very lonely place – I have no such compulsion…I do whatever I need/want to do and the rest I can easily let go – and I know how anxious and frustrated I get when I am confronted by an extended period of time where I must be in control or always “on-top” of things. Being in that “must keep it together” space 24/7/365 must really be awful.

Needless to say, when someone starts to compromise or sacrifice their own physical well being, you can be damn sure that they long ago started to cut back (if not jettison altogether) things that might be relevant to their own mental and emotional well being. Without that personal time and space, there is no no time to center oneself, no reset button, no allowance for creativity or imagining or dreaming and fantasizing – no escape! It must be suffocating.

Along with that endless personal self-sacrifice is a more nuanced but perfectly logical (even if ultimately misguided) prioritization chain about what she should do when she DOES get those rare moments of precious personal space. My understanding of what that prioritization list is or should be is irrelevant, but, suffice it to say, sex and nurturing ones innate sexuality, is (as it is for many, many women) predictably very low on the list (almost at the absolute bottom).

There are all sort of reasons why this is the case and cultural and societal norms and beliefs play a huge role in diminishing the importance of it – disproportionately so for women – but, I can not think of anything more depressing or fundamentally wrong-headed that this is, generally speaking, a reality for most women – especially mothers and doubly so for working mothers.

It sounds as if you have experienced quite a bit sexually and know who you are and are not, what you like and what you don’t and what satisfies and fulfills you at least sexually if not also emotionally. Lucky for you (and me and all the others who have realized the importance of sex and sexuality to ones emotional health and well being), there are probably years of emotional self sacrifice underpinning your woman’s perspective. If my characterizations and assumptions are right (or even close) there are at least as many years of complete neglect of anything but her most basic of sexual needs. Forget about being able to express them clearly or of having an elaborate or diverse repertoire of sexual fantasy’s on anything but the most generic level.

It sounds to me as if she is looking for someone to become her emotional and sexual guide/guardian, or as I like to think of it her Emotional Dominant. Someone to take care of her in the ways that she is fundamentally ill-equipped or unable to do for herself. Foremost among those “needs” is her recognition of the relative importance to her of exploring her sexuality to nurture and sustain her emotional well being and an acknowledgement of her fear or frustration at her inability to go there without trusted counsel.

It sounds like that person is YOU, or at least it could be. This is a long way from the mostly bullshit version of a D/s relationship seen in porn. This is a different animal altogether and potentially much, much more rewarding for you both, one in which you really can assess what your own sexual goals and aspirations are and how you can push her towards filling all of them. You have to take responsibility for making sure that she gets as much or more out of whatever experience you can dream up, and it has to fit within the boundaries you negotiate, but, if in introducing her to the pleasures of another woman your dick finds itself in said other woman, then everyone wins… and by the way, the pleasure and enjoyment that you take away is a big-time turn on for her IF she is really letting go of that control and her old ways of thinking that created the imbalance in the first place.

So do what you have been doing…talk to her about it, introduce her to your world, open her eyes to all the ways that you can feel and express yourself through your sexuality, challenge her and provoke her (in ways that are both shocking and endearing) to both express her beliefs and also her wants and desires. She has already bought in to this adventurous lifestyle that you have introduced her to with a very open mind (no other way to describe that second man experience). It is your time to understand how your life experiences are so different from hers and that many of the basic things you take for granted might not even exist in her mind. Now it is time for you to develop your own Vision of how to do that!

This is about taking that Dominant role emotionally and sexually in your relationship. Everyone always gets complex hardcore “Story of O” image when they imagine such situations/circumstances. You do not have to be that type of dominant. You simply have to decide if you are willing (there really should be no doubt that you are able – because you seem like a very intellegent man) to take on that type of a roll for her. Make no mistake, this very well may be much more about her and what she needs than you and what you want or need. Also don’t make the mistake of thinking that by expressing such a need that she may want you to build a St. Andrews Cross in your basement and keep her in a cage at night! She “needs” someone to take her someplace she can not access on her own – that isn’t always or even necessarily sexual and it really may be no more complex than doing exactly what you already seem to be doing…but the outward acknowledgement and acceptance of such a dynamic could in and of itself ease her mind and conscious immensely… So be careful not to walk into this discussion thinking that you are about to redefine your entire relationship.

If upon further discussion and exploration she does want that St. Andrews cross and you with bullwhip in hand, then the question is still open as to whether it will scratch your itch sufficiently to justify the increased care and attention and effort on your part. Trust me, this type of a relationship could require a lot more effort on your part. But, if you derive pleasure from seeing your woman’s eyes opened to the possibilities, watching her tentative first steps, hoping to see the unbridled joy and ecstasy that her sexual liberation might bring her, feeling the love and adoration and affection that she may bestow upon you for making such a difference in her life, and better yet, being a participant who is along for the exhilarating ride and, through this process, being able to make your own wants and desires and fantasies known and possibly come true (there is very little a truly dedicated sub won’t do to show their appreciation for the gift that you have given them)…then you will have truly crossed over and no one has been truly harmed or disrespected or degraded in the process.

So how far outside of your comfort zone or areas of interest would you go to achieve such an outcome? What could you get out of it? What could she do for you that would make it worthwhile (and don’t insist on a threesome with another woman for administering a few weak slaps on the ass!!!) – but suggesting that you would like her to be open to you introducing her to other things, slowly, gently with respect and understanding of how she feels, but in a way that likely challenge her own current perspective and pushes her boundaries (teach her how to give a better blow-job…deep throat…swallow your cum – help her understand why a woman’s touch instead of another man’s may in fact be what she needs) Anything and everything is negotiable, thinking about it, talking about it exploring it may be rewarding enough and you may both conclude that you should skip the whips and chains entirely.

Or you may realize how the opportunity before you is sooo much greater than you think…