So in a similar style to my first episode today we are entering the chaotic realm of cuckolding. I say chaotic due to navigational issues, but I think we can all agree, chaos can be fun! Rainstorms are chaotic, and yet some of us like to dance in the rain! I know I do!

So, cuckolding – what is it?   

If you have never heard of the term before then I will say that I am very surprised, but I will do you the courtesy of an explanation. In its simplest form cuckolding is the term used to describe the act in which a boyfriend or husband either watches or is aware of his adulteress partner engaging in sexual activity with another man. There are so many subtle details that are unique to any given couple, but the general idea is that the boyfriend or husband experience intense sexual gratification from either watching, or hearing about his partners experiences.

Now, if you are a potential cuckold, then this description will likely strike a chord with you immediately. You’ll either be sitting there thinking about all the possibilities of such a naughty opportunity, or this will have been the subject of many fantasies for you prior to this podcast. If you are instantly thinking to yourself “Nope, that’s definitely not my cup of tea!” then chances are it won’t be – and so I wouldn’t recommend pushing yourself into a situation in order to declare your status as a well seasoned kinkster. 

Ms Ruby’s Cuckolding Tips

So, if you are thinking about Cuckolding for the first time then here are my tips on how to get started!

Fantasize during solo play sessions

When you feel the urge to pleasure yourself, I would highly recommend taking the time to think on the cuckolding theme. Plan it out and let your mind wander in that direction. How do you discover your wife’s need for new cock? Do you walk in on her with another guy? Does she tell you about an experience with an ex lover while you are getting it on? You can start off subtle or dream big, there are no wrong answers. Put yourself in the scenario and try to engage with your own arousal and emotions. What types of feelings are coming up? For most guys it will be an intense concoction of lust and jealousy. And it is perfectly okay to feel jealous. The great thing about this scenario is that we are free to feel what we feel and we don’t get any of the potential complications of a real life experience. Feel it out and try to understand what it is about cuckolding that most appeals to you.

Watch cuckold porn

This one seems pretty obvious as it is usually the go to solution for many kink explorers. Now you will encounter so many different scenarios with this one. Some of them will appeal to you, whilst others may not. This is okay. As I said before – we are just feeling it out at the moment. Some may even inspire future fantasies or roleplay scenarios for you, which is always a good thing. Just make sure you won’t be interrupted whilst doing this. The last thing you want is an extra layer of anxiety in the mix whilst browsing. 

Ask your partner about her exs

If and when you are ready to experience a more realistic feeling of what cuckolding can do for your arousal, then feel free to ask your wife or girlfriend about her past experiences. It is absolutely crucial that you pick the right time to do this. You don’t want to freak her out by randomly asking her whilst she is preparing dinner or something like that. The best time to do it is when you are both in bed, relaxed and comfortable. Now, if the previous two tips have invoked intense feelings of jealousy you may want to tread carefully with this one. If you know you can handle it, then you can go ahead and ask. But an honest assessment of your emotions and reactions prior to jumping in will allow you to make the right decision for you. Remember, it is perfectly okay to keep cuckolding in the realm of fantasy. There is no reason to try and manifest it in reality unless you really want to do so!

Ask a mistress for advice

If you are wanting to know how far to take it and need someone to guide you through the challenging terrain of kink exploration, then you know we are here for exactly that! Consider arranging a session with one of us to chat about your new fascination with cuckolding. We would be more than happy to accommodate your needs. And roleplay is a fantastic outlet for sexual tension and self discovery! We will work out exactly what works for you and feel out your personal limits.

Chat to your partner about your new fantasy

If you feel as though the information would be well received – think about discussing it with your partner. You should do this without any expectation for her to fulfil your desire. You need to approach this in a different way. You’re not asking for her participation, so much as confiding in her. Trust me, if you do it this way without any expectations, she is far more likely to receive the information well. Maybe she will even entertain the idea if her curiosity is peaked.

Talk about it during sex

So, you’ve gone through with it. You’ve told your partner your inner most secrets. She’s responded well and has asked you questions about your new fantasy. She understands all of the elements that you enjoy and she is open to chatting more about it. How do you progress from here? Well, instead of asking her to go out and find a new fuck buddy, you are going to humbly request that she allows some kinky dialog during sex. Maybe you ask her to describe her exs big cock while your deep inside her. Maybe you even like the idea of being humiliated a little so you ask her to compare your efforts with his, making a point to tell you he was a lot better. Maybe you want her to make up a story about getting off with someone at her last work do.  If you have followed my previous tips, then you should be well versed in your own cuckold arousal triggers. Also, I just want to mention, that if you are going to follow this tip, then make her feel special too! She is catering to your fantasy and so the least you can do is treat her to a meal or nice new lingerie set. Make a date of this with the intention of some really hot sex afterwards!

Talk about the reality of cuckolding

So if all has gone well so far, then there is no reason not to have a real life chat about the practicalities of cuckolding and what it would mean for you and your partner. This conversation isn’t the kinky kind, so much as a reality check. You need to take stock of your relationship, communication skills and expectations. If you really want to take things further then this step cannot be skipped. Check in with her and let her know that this is something you would love to experience in real life. If she  tells you that she will not entertain the idea in reality, then you will need to except her decision and not push any further. If she is a little more open, then you need to be totally honest, talking about the good as well as the potential hang ups.

You remember at the beginning when I said that cuckolding can become chaotic. Well this is where all of these concerns need to be addressed and ironed out. Talk about the situation as a hypothetical. If you feel an argument brewing, apologise in a genuine way and let her know that you do not want her to feel pressured at all. The decision to move forward has to be mutual, or it will be a disaster. Don’t push. Be patient. Also, let her know that you have no interest in the roles being reversed at any point. If your fantasy is solely based on cuckolding, let her know you do not want to engage sexually with any other women and that your only desire is to see her being pleasured in the way she deserves.

Find the bull together

So in cuckolding the term bull is used to describe the other guy. The man that will be engaging in sexual experiences with your partner. Usually the guy is an alpha/Dom type, but this doesn’t have to be the case. I have coached many clients in cuckolding situations where the other man has been pretty laid back and polite. It is important to feel this area out as a couple for a few reasons. 1) the selection process will be a lot smoother. Sometimes online adds for a third party for bedroom fun can attract all the creeps. It’s your job as a couple to help identify a good match. Finding the right person is going to take time and so you need to prepare yourself for that crucial vetting process. You want someone who is exciting for your partner, but at the same time respectful of your boundaries. 2.) when you look at this as a couples task, you actually gain sexual excitement from it! Watching her look through photos and hearing her honest opinions about other men will drive you wild! So, take the time to really think about what you are looking for and then get to work!

Do a phone / video call

Once you have found a good candidate, then you will want to think about inviting him to chat with both of you. This is not for sexual conversation. At this time you are just trying to figure out if this guy is worth meeting up with! Sex shouldn’t come up. This is a casual chat to see how you all interreact and get on. Think of it as a casual interview.

Arrange a casual meet up

As I’ve mentioned before, this is a long process, but so worth it when you find the right person! You’ll want to meet in a public setting – like a coffee shop. Again, this meet up is not about sex. Instead, this is a real life opportunity to get to know each other a little better. Make sure you and your partner have a subtle signal if there are any immediate red flags. That way, you can leave pretty quickly without causing a scene. If he insists on coming home with you, then note this IS a red flag!

Arrange a final date

So you’ve followed all of my tips and you now have a potential match. This time you want to arrange something a little more intimate. I suggest cocktails at a local bar. DO NOT get drunk! You want to keep your wits about you, having one or two drinks will enable you to loosen up without losing your head! I would recommend booking a separate date it you all want to move forward from here. This allows you to sleep on it and go over any ground rules with your new play mate!

My personal experiences with Cuckolding

If you want to hear about my experiences then you will need to listen to my Cuckolding 101 Podcast Episode. You can find this HERE!

That’s all for this week guys, tune in next week where we will be discussing Edging and why it is one of my absolute favourite tools in teasing!