Welcome to episode, "150: Permission to Be You: Rethinking Masculinity, Eroticism, Kinks, Cross-Dressing Without the Shame, Sexuality, Self-Love & Coming Home to Yourself" of the All Things Love and Intimacy Podcast, hosted by Katie Ziskind, Licensed Marriage and Family Therapist, Certified Sex Therapy Informed Professional, 500-hour Registered Yoga Teacher and yoga therapist, and the founder of Wisdom Within Counseling and Coaching.
What happens when the man you were taught to be doesn't fully match the person you feel yourself becoming?
You grew up in a conservative or religious environment where masculinity was very clearly defined. You were taught that being a man meant being strong, dominant, stoic, heterosexual, emotionally contained, and always in control. You learned that vulnerability was weakness and that certain kinds of pleasure, softness, or feminine expression were something to hide.
And then, as an adult, you discover another part of yourself.
Maybe you love wearing feminine clothing. It brings you comfort. You feel beautiful or peaceful in a way you haven't allowed yourself to experience before. You have sexual interests that don't fit the rules you were given. Maybe you enjoy forms of sexual pleasure that create questions about your identity.
Katie speaks directly to men who may have spent years hiding parts of themselves because of conservative, religious, patriarchal, or traditional beliefs about what it means to be masculine. If you enjoy wearing women's clothing, exploring feminine expression, experiencing softness, or discovering sexual desires that don't fit the expectations you were raised with, you are not alone.
This episode explores why cross-dressing can feel both comforting and complicated. Katie discusses how anxious parts can emerge when you begin questioning beliefs you've held for decades, particularly when sexuality, masculinity, religion, and family expectations have been deeply intertwined.
Katie also explores the connection between narcissistic or emotionally difficult parenting, childhood conditioning, shame, people-pleasing, emotional suppression, and the masculine mental load. When you've spent your life managing everyone else's emotions, being strong, providing, protecting, and "cushioning" other people, learning to nurture yourself can feel unfamiliar—but incredibly healing.
The conversation also addresses sexual pleasure and sexual orientation. Enjoying anal stimulation or penetration does not automatically determine whether a man is gay, straight, bisexual, or another sexual orientation. Sexual behavior and sexual orientation are related but distinct aspects of human sexuality. Katie discusses why discovering new forms of pleasure can nevertheless bring up anxiety, shame, confusion, or fear—especially for men raised in conservative or religious environments.
She is a sex-positive, LGBTQIA+-affirming therapist specializing in relationships, sexuality, intimacy, trauma, complex trauma, attachment, and emotional connection.
Katie Ziskind specializes counseling and coaching for feminine men, cross dressers, and transgender women in relationships, sexuality, intimacy, sexual abuse, religious trauma, complex trauma and C-PTSD, emotional connection, and the places where our early experiences can shape how we understand ourselves, our bodies, our relationships, and our sexuality.
She is deeply passionate about working with men and penis owners who are exploring parts of themselves that they may have spent years hiding—including cross-dressing, feminine expression, sexuality, bisexuality, sexual desires, sexual orientation questions, vulnerability, and the emotional conflict that can happen when your authentic self doesn't fit neatly into the masculine or conservative, religious expectations you grew up with.
At Wisdom Within Counseling and Coaching, we can help you understand the difference between what you genuinely desire and what you were taught you were supposed to desire.
