Mailbag Monday: Sex – Good, Bad, and None

Posted: June 16, 2014 by Isaac Cross in Advice, Learn Something, Technique

It’s Monday, so here are some quick answers from to questions that I have received.

Or… In some cases, questions that someone asked in my general vicinity or somewhere on the internet. But I am answering them here, because that’s where I am.

The questions have been paraphrased or otherwise edited down to the essential details.

Do you Have a Question? Drop it at the Contact Me Page, or you can post to any of the social network platforms listed to the left. (Unless you are on your phone or something, in which case, you can find he list here.


Also be sure to subscribe using the “Stalk Me” button to receive email updates and notifications of new posts and/or follow me on all the social networks. I post unique things to each one, so it pays to Follow Me Everywhere.

Does BDSM = Sex?

I identify as asexual and I’m interested in discussing and learning about what interests others in sadism and masochism as well as techniques they may use which are not necessarily sexual. I’ve been looking for resources about S&M specifically but haven’t found any.

Everyone approaches BDSM differently. For some, everything has a sexual flavor to it, and many people end every SM experience with sex. But many others have absolutely no connection between their SM play and their sexy time. For me, while it certainly varies up and down, I would say that about 80% of my SM play has no sexual element to it at all. At the two primary clubs that I play at, sex is a rarity, even though it is allowed.

As far as resources are concerned, most instructional books and websites that I am aware of have plenty of information that is useful whether or not sex is incorporated as an element. Check out my bookshelf page for lots of great ones. Consider starting with SM101 by Jay Wiseman and figure out from there which types of activities interest you most.

If you have specific questions about a particular activity, feel free to respond in the comments or send me an email at

And speaking of not having sex…

Is Chastity Supposed To Be This Frustrating? 

I’m on day 3 of chastity, and my god I’m super frustrated. This isn’t my first time in chastity, but last time was only 2 days, and he wants to push me to a week this time.

So my question is, is chastity mainly a mind game? It’s been throwing me through many different emotions, ranging from depression to anxiety. Is this just from not cumming everyday like normal? It’s making me a bratty smart mouth bottom just begging for punishment.

The main point I’m trying to get at, is how to I mentally overcome chastity?

Well, the short answer is, “Yes”. Chastity is supposed to be very frustrating. But it is also a process. Everyone is going to experience that process differently, but it will almost certainly affect your mental state in significant ways.

There is a book on the Bookshelf Page called Male Chastity: A Guide To Keyholders. As the title implies, it is written more for your keyholder than for you, but since it gives a lot of insight into the mental process of the male in chastity, the book may help you to understand the process that you are going through a little bit better.

There is not, as far as I know, any good books on actually being in chastity, or advice for dealing with it, but if you do a google search, you will find many websites and communities dedicated to this topic. You might also join the Fetlife community for males in chastity and ask your questions there.

The one thing I will say for sure is that what you get out of the chastity experience is absolutely determined by your attitude. If you are trying to “mentally overcome” it or trying to win the “mental game”, then you are going to struggle and suffer a lot. If that’s what you and your keyholder want, that’s fine, there is nothing wrong with that. But if you are trying to reduce your suffering and frustration, the key is to surrender to it, rather than trying to conquer it. Accept that the way you feel cannot be controlled, and be sure to communicate with your keyholder often so they know what you are feeling and can decide what to do about it, if anything.

Long Term Bondage and Sexual Torture

My GF wants to be tied up and sexually tortured “for days” (her words). Help with logistics?

She said she wants to make some ground rules first, but what should we keep in mind? She wants to feel as if she’s been kidnapped, how should I take her to the bathroom, feed her etc, without taking her out of it?

This is a first for both of us. She says she wants her will to be completely broken, and she doesn’t want there to be a safe word.

I know I have written on this website that I don’t use safewords, but that does not include a scene like this. There absolutely, 100%, MUST be a safeword. Or several. The standard in clubs is the traffic light system. Green says that everything is OK, even though it sounds like it’s not. Yellow says that something needs to be adjusted, but I still want to keep going. Red means you want to stop all together.

No mater what type of play you are doing, the bottom MUST have a way to remove consent and stop what is happening or the top can and will be charged with crimes including rape, assault, kidnapping, and any number of other charges.

As for logistics, starting with several days is simply too much.

I have been with my current partner for 9 years. Shortly after our fifth anniversary, I arranged for her to be kidnapped for her birthday. To do this, I enlisted the help of 10 other people, we planned for months in advance. There was a 20 page briefing packet and we rehearsed every aspect of the scene multiple times before hand using a stunt-bottom. You can read about that experience here, here, and here.

After that massive amount of planning, the scene lasted about 6 hours. That was more than enough to achieve a “break” and any longer would have simply been too much for her. And that is with 5 years of very extreme play and experience with edgier scenes.

And by the way, at the end of that day, the tops involved needed more aftercare than my partner did. Non-consensual role-play can be deeply disturbing if you aren’t prepared for it. So concerns for her aside, you need to make sure that YOU can handle a scene like this.

You are putting yourselves at an incredible risk if you go through with this as described in your question.

It’s a hot fantasy, but there are just too many land mines to make it worth the trip.

Here is a practical suggestion, though.

If she wants to be stuck in the house for a few days and be at your mercy. Simply pack up every single piece of clothing in the house and store it somewhere else for a few days. She won’t be able to leave, she will relay on you for everything needed, you can set up ways for her to earn her clothing back a piece at a time (First socks, then shoes, then underwear, etc). This will be much lower pressure, can be seriously fun, and achieves that vulnerable, dependent, and captive experience without the logistical hurtles and safety concerns of actually having her tied in place for long periods. Just an idea.

Anyway, the bottom line is you should start smaller. Don’t do this until you know that both of you can handle it. And whatever you do, make sure your top priorities are:
1. Her Safety and Well-being
2. Your Safety and Well-being
3. Not Getting Arrested
4. Fun

That’s it for this week. Be sure to contact me if you have questions and follow me everywhere for other posts, comments, advice, and updates.

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