There are so many levels to cuckholding.
During a cam session I usually list these levels to gauge two main aspects. One is how involved a guy wants to be in the whole scene, as well as his true desire and intention behind wanting to explore cuckholding.
General levels are:
· Knowing she (wife/gf) is with other guys, but not sharing any details
· She is with others and tell you all the details after she comes home
· She is with others and lets you touch or even taste after
· She is with others while you are home but in a different room
· She is with others while you are in the room-either getting to touch or not
· You get to prep her or him (usually oral performed on them) then watch them together
· You get to watch them then perform oral on one of both of them in a clean-up type action
· Be actively involved while they are playing together-often licking pussy or balls while they fuck, could be stimulating either of their assholes, etc.
· Could be more actively involved with his cock-usually being fucked during or after he fucks her
Depending on what level the guy is interested in speaks to the underlying reason for his interest in cuckholding overall. There is usually one of two underlying reasons behind a desire for cuckholding. The first is that he wants to prioritize his partners pleasure, the second is because he wants to play with a cock. He may want to prioritize his partners pleasure because she is his priority, or because he is inadequate in some way-could be premature ejaculation, or penis size etc. The most common reason that men are interested in cuckholding is because he wants to have exposure and experience with another cock and feels he needs his partner there “to make it ok”. In this case his partners pleasure is often of little or no interest to him.
When a guy is focused on her pleasure it is a sweet and beautiful thing. This usually comes from one of two sources.
1) There is a power dynamic aspect to their relationship. She is a Top, Domme, or the commander in the relationship, and he has an aspect of servitude in how they interact. He most likely defaults to her in many areas of their life. Or, he is always in charge in life, work, relationships, but gives it all up in their sexual relationships. His prioritizing her pleasure in itself gives him pleasure and a level of satisfaction.
2) He has some level of inadequacy in his life or sexual ability. This could be from a lack of general confidence, could be a lack of sexual skill or experience, he could have a problem with premature ejaculation, a smaller than desired penis.** Accepting that he has an inadequacy, and therefore prioritizing their partners pleasure over his own is a beautiful thing.
When a guy is focused on his involvement with another cock it can be a very different experience for all involved. This is usually that he simply feels the need to have a trusted partner/woman with him in order to accept his desire to play with another cock.*** It can be that he wants to explore with the support of his partner or share the experience together. In this case the focus is not specifically on her pleasure but on his experience.
Successful and/or long-term cuckholding relationship involve a lot of communication, respect and understanding. There are so many ways to have assumptions and misunderstandings get in the way. Clear communication about intentions and expectations can ensure that all involved have a wonderful time before, during and after play time. This also leads to discussing how you find a third to join your relationship whether for a single session or an ongoing situation.
Regardless of the underlying reason for the interest in cuckholding the partners have to be able to be honest and clear with each other. A couple needs to establish some ground rules on their expectations, and most importantly limits on the activities of the scene. While no one can fully script how a play session will go they do need to be able to agree and then communicate with their third as what is ok and what is not ok. Partners need to be confident in speaking up and establishing the rules. Once these rules are established it is time to find a person to join.
Some people want to have someone that they know and are already friends with since there is already a connection and possibly chemistry which can make everyone comfortable. Others prefer a complete stranger that is only in their lives for this aspect (single session or ongoing). While it is super easy to find horny men who want to have sex in a variety of ways, the challenge can be to find one that is capable of understanding the dynamic, the rules and the expectations. This can be a frustrating and challenging process to work through to find the right match. Often hiring a professional (male sex worker) is a good idea because there is a level of professionalism and often experience. There is so much communication needed prior to the play session, but there is often just as much needed afterwards. Right after, all three can discuss what they liked, what they would alter, what they hated. The three-way conversation is usually needed if the goal is a repeat play session, less if it was a one-time thing. The couple certainly needs to discuss in detail how they enjoyed the session, what they would change and what they didn’t want to do again. So often fantasies can be really challenging to bring into a reality, and this can lead to a high level of disappointment if it doesn’t play out as expected. Whether a one-time thing or an ongoing power dynamic the relationship will change and grow through new experiences.
**Penis size has absolutely nothing to do with the ability to pleasure a partner. Small penises can be amazing and large ones can be absolutely useless.
***There are so many layers of stigma and internalized homophobia in our society and this is a huge example. Men feel like they need a woman around in order to play with another cock.