THE BEGINNERS GUIDE TO CONTEMPORARY CUCKOLDRY
The primary question I receive from men is how to discuss cuckoldry with their mates
once the subject is broached. Many couples think that they can jump into active
cuckolding with little to no recourse by establishing a few rules.
Unfortunately, this is not always the case. When exploring cuckoldry, you open your
world and your relationship to a myriad of possibilities. They might not be what you
expect. Moving from fantasy to reality requires a bit of forethought and a lot of
transparently honest communication.
Here are over 40 questions I recommend reviewing before your first sexual
encounter. I cover these and more in private mentoring, but this is enough to start
the conversation.
Take your time answering the questions in this workbook. The more detailed and
honest your answers are now, the fewer hiccups you are likely to encounter later. For
more helpful information, check out my best essays on cuckoldry or contact me for a
free consultation.
Understanding Your Identity: What Does It Mean to Be a Cuckoldress or a
Cuckold?
Begin understanding what being a Cuckoldress or a cuckold means to you by answering
the questions in the next section honestly about yourself. Skip any questions that do
not apply to your role in the relationship by writing “Not applicable” in the answer
section.
If you are answering these questions with your partner, print two copies, answer the
questions separately and without discussing your answers until you complete the
exercise. Then, once you have completed the exercise and reviewed your answers
separately, discuss your responses.
Practice transparent honesty, active listening, and compassionate acceptance as you
listen to your partner’s responses, especially if your response or the response you
expected or desired from your partner differs.
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THE BEGINNERS GUIDE TO CONTEMPORARY CUCKOLDRY
1. Do you identify as a submissive man who enjoys watching his wife explore
sexually?
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2. Do you identify as a dominant man who enjoys showing off his wife sexually?
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3. Are you a woman who is confident in her sexuality and enjoys having power
over her husband?
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4. Are you a submissive woman who prefers that someone else take the lead in
the bedroom, but does not seem to have that sexual compatibility with her
mate?
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5. Do you want chastity, humiliation, sissification, forced feminization, forced
bisexual activity, or any other fetishes included in your relationship?
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THE BEGINNERS GUIDE TO CONTEMPORARY CUCKOLDRY
6. Do you prefer sharing your identity as a cuckoldress or cuckold something
openly or keeping it discreet?
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7. How would you prefer to practice cuckoldry — passively, actively, or
organically?
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8. Is this a game you prefer to play on vacation and long weekends, or something
you want to influence every aspect of your life?
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9. Do you prefer something more vanilla as a female-centric couple or do you
want a bit of kink mixed in to add some spice?
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10. Do you feel drawn more to Contemporary Cuckoldry or hotwifery?
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THE BEGINNERS GUIDE TO CONTEMPORARY CUCKOLDRY
11. How would you prefer to interact with a Bull or a Lover?
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12. Would you prefer to call a third person a Lover or a Bull?
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If you fall somewhere between the answers you provided so far, specify what you
want so you and your current or future triad will understand fully what you mean and
what you need to feel fulfilled. Then, continue with the remaining questions.
The Basics
1. What do you hope to add to your relationship by exploring cuckoldry together?
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2. How will you handle the angst?
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3. How will you handle the emotional bond that occurs with a lover and a cuckoldress?
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4. Will romance be a part of your active cuckolding with the lover?
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THE BEGINNERS GUIDE TO CONTEMPORARY CUCKOLDRY
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5. What rituals do you have in place for bonding before and after you take a lover?
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6. Will the experience be temporary to test the waters?
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If so, how will you decide when it ends (e.g., a set date, a specific reaction, a
one-time thing)?
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7. How will you move forward if you discover cuckoldry is not something you enjoy?
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Will either of you be disappointed if that's the case?
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How will you handle that disappointment?
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If you find you enjoy it, how often will you actively involve a third-party?
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THE BEGINNERS GUIDE TO CONTEMPORARY CUCKOLDRY
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The Third Person
1. What type of lover do you want? (e.g. full-time, part-time, rotating, live-in)
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Do you prefer Bulls, Hedonists or some other variety?
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What criteria must a man meet to be considered a potential lover?
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Would a dominant, submissive or switch personality complement your
relationship best?
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2. How will the third person fit into your lives?
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Are you looking for a series of one-night stands or something more consistent?
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THE BEGINNERS GUIDE TO CONTEMPORARY CUCKOLDRY
If you are expecting something more consistent, does it include a live-in
arrangement?
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What would the living arrangement be?
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If you have children, how will he be introduced, if at all, to the family (e.g., a
family friend, a coworker, etc.)?
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Health Questions
1. How will you handle protection (e.g., condoms, birth control, etc.)?
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Who will be responsible for providing it?
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What type(s) of fluid bonding will there be with the lover? (e.g. kissing,
swallowing pre-cum, semen/vaginal fluid, etc.)
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Who decides when, with whom, and under what circumstances this will
happen?
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THE BEGINNERS GUIDE TO CONTEMPORARY CUCKOLDRY
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2. Will you get full spectrum STD/STI tests before? (Bear in mind that you must
specifically request an HSV1/HSV2 aka Herpes Simplex Virus Test. It is not part of a
“full spectrum” test without a specific request per the CDC.)
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3. Have you considered how you will handle an unplanned pregnancy, which is a very real
risk even for the most cautious couples?
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4. Who will start these conversations with the potential lover?
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Logistics
1. What will you say to anyone who shows concern for your marriage, if someone sees
you and the potential or current lover in a public setting?
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2. Where will active cuckolding take place?
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THE BEGINNERS GUIDE TO CONTEMPORARY CUCKOLDRY
If outside the home, who will assume financial responsibility for the dates?
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If inside the home, what criteria or security measures must be met?
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Do you have a contingency plan if something goes wrong?
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3. What precautions must you take to prevent your increased sexual activity from
impacting your careers?
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4. How will nights out affect your children and what reason will you give them for your
absence if any?
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These are important questions to which you must have the answers before deciding
what agreements will govern your exploration or your first encounter. Even after you
answer these questions, be open to other questions that will arise as you explore.
Continue discussing cuckoldry and your expectations as you explore.
Do you need help understanding yourself, your partner, or this exercise? Join me for a
free discovery session today by clicking the booking link below.
To leave feedback on this exercise, click here.
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