9 Reasons to Covet a Crossdressing Partner Want to feel like a goddess? Let him play sissy. Maybe you caught him, or maybe he told you. You may have been married for decades, or on a first date. Regardless…the moment you learn your man crossdresses,1 it’s going to shake you. But take heart—once you get over the shock, you’ll learn that you’ve just received a gift that can make your life and relationship truly amazing. Aside from my profession, I’m
9 Reasons to Covet a Crossdressing Partner
Want to feel like a goddess? Let him play sissy.
Maybe you caught him, or maybe he told you. You may have been married for decades, or on a first date. Regardless…the moment you learn your man crossdresses,1 it’s going to shake you. But take heart—once you get over the shock, you’ll learn that you’ve just received a gift that can make your life and relationship truly amazing.
Aside from my profession, I’m probably not much different from you: a straight ciswoman who loves accomplished, rugged, alpha men. I’ve been involved with vanilla men and kinky men, submissive men and dominant men, and loved them all. In my 50s, I left corporate life to begin a new career mentoring crossdressers (CDs), sissies,2 and other gender players, and have worked with hundreds since then.
And, yes, they talk to me about you, a lot: their wives, girlfriends, and dating prospects. About how much they love you, or want to love you…and how they know you’d be threatened, shut down, hysterical, judgmental if you found out…that you’d never understand. They confide the pain of keeping this secret from you, often for decades, rooted in fear of losing your love and respect. Single guys want to know when to tell a new girlfriend, or wonder if they can repress it for a lifetime if they can only “find the right girl.” (The overwhelming answer seems to be NO.)
And what is his sin? That he likes feeling the texture of silk and lace against his skin? That he sometimes enjoys dropping the burden of masculinity to play in a sandbox of soft, colorful fantasy? That this is how he loves to escape the stresses and harshness of everyday life, if only momentarily?
I’m not here to tell you WHY he likes it… you can find plenty on that from people more qualified than I. But I AM telling you what can be in it for you as his partner, once you move past your own fears and insecurities. Even if it doesn’t stoke your own fire, it can always be fun—and it’s a powerful bonding mechanism. If you’re broad-minded enough to adjust your thinking and attitudes, the crossdresser in front of you can be a dream mate.
So… the bomb has dropped. He wears panties and more. He’s kept this secret for years. Nobody chooses this; it’s in his wiring. And if he trusted you enough to tell you, that’s a special spot, my friend.
So before reaching for the smelling salts or heading for the door, consider the benefits you’d be rejecting. Some are practical, some more profound:
Even if you weren’t into Barbies as a kid (I wasn’t), glamming up a man as an adult is a whole new world of fun. Lighten up and play, and forget about gender roles… doll him up and see what you can create!
Life is about making memories. I promise, you’ll always remember the experience of turning your reserved Bob the Accountant into Babette the Slutty Coquette. So will he. Fondly. Forever. In vivid detail.
Love it? Hate it? You win either way. He secretly adores it, even in male mode, and is an enthusiastic companion if you include him in your shopping adventures. Do you find it tedious or too time-consuming? With guidance, he can become your own personal shopper—just let him buy some pretties of his own.
Make him wear panties or a dress, show some playful appreciation, and most submissive-type CDs will do more of it, and more happily. Why? Because he gets to do “female stuff,”3 and you told him to. Ditto for developing new talents: sewing, cooking, massages, serving you breakfast in bed. All you have to do is ask, with intermittent positive reinforcement. Seriously.
You’re not bisexual, you say? You only want a manly man in bed? That’s okay! You have as much right to your erotic preferences as he does. If you don’t enjoy his crossdressing in your sex life, he won’t push it. Remember, though, that he also deserves opportunities to enjoy this part of himself, erotically and otherwise. It’s unfair to deny him that. Find compromises that work for you both.
But if you can open your mind to this part of him in the bedroom, even sometimes, you have much to look forward to. While many CDS have staid exteriors, they become playful, imaginative, creative lovers when set free—and they’re more turned on by giving you pleasure than receiving it. Really.
It’s easy to tap into his innate desire to please you—just tell him what you want. A hard, dominant masculine fuck? A soft, sensual evening of pampering and worship? Wine, Netflix, and a foot massage? You can have it. A sissy is wired to make you happy, but the electricity comes from your participation. Put him in panties at appropriate times. You’ll see.
When he looks at another woman, he’s more often studying her wardrobe and mannerisms than wondering what she’d look like naked (but he’s still a straight or bi man, so that won’t completely escape his mind). If he’s looking at you, it’s with increased devotion because he realizes how lucky he is. He knows that he won’t get this support from most women. The very fact that you accept this deeply personal need of his can commit him to you for life.
Gender play brings a fun new element into your dynamic as a couple, no matter how long you’ve been together. A crossdressing partner introduces a smorgasbord of things you can explore and do together, within your mutual tastes and boundaries: clothes, lingerie, makeup, outings, remote control toys, domestic and sexual service, role play, Femdom fantasies… you might even be drawn to more intense practices such as orgasm control, chastity, strap-on play, BDSM, or cuckoldry. It’s easier to maintain a playful spirit with so many creative ways to delight and surprise each other.
After sharing his most intimate desires with you and experiencing the joy that your acceptance brings, a CD or sissy is capable of emotional depth that he would never reveal to less accepting partners. You’ll find him more attentive than most men.
Your enjoyment of his femme side liberates the softer parts of his nature that are repressed in daily life. When he dresses, he wants to show how caring he is…he wants to see things from a “female point of view”3…he wants to be your girlfriend. You’ll be surprised by how sensitive, nurturing, and sensual he’ll become.
If you go out in public together en femme, people will look. So what? Assuming you’re both well mannered and dressed appropriately (e.g., no stripper shoes and lingerie at a family restaurant), those brief glances and occasional stares are typically rooted in curiosity or garden-variety discomfort with the unfamiliar, not direct hostility. Consider that you’re helping to open minds to all forms of “differentness.” Being secure in who you are, and in who you love, silently inspires others who may be hiding their own secret.
Being in a relationship with a crossdresser provides an opportunity to examine what gender, relationships, sex, and love mean to you. You can check your capacity to accept things you don’t yet understand, and get clearer on what you value in your partner. Whether he’s disclosed his secret himself or you’ve discovered it on your own, his soul has been bared to you. The resulting growth and self-awareness, individually and as a couple, are priceless.
Remember, he’s still a man. He will still protect and care for you. You can still be on his arm in public. People will admire you as a couple—perhaps with some envy at how connected and playful you seem to be. Nobody else has to know about his desires. You do…and that means the world to him.
Give him the magnificent gift of loving all of him. Not just the parts you cherry pick. You’re likely to get the same in return.
If you can’t find you can’t do that, if it’s just too much of a personal stretch, then be kind. Don’t shame or try to “fix” him. Let him go. Find someone whom you can love completely, and give him the chance to receive the same.
But if you suspect your guy crossdresses, send him a link to this article, or print it and leave it somewhere he’ll find it. Maybe with a tube of lipstick and some new panties. It’ll be a love letter that drops him to his knees.
1 This article is about crossdressers, not transwomen, although some of the benefits are similar. I’m talking about men who identify as male and dress in feminine attire for relaxation, escape, or erotic pleasure.
2Sissies are a special subset of crossdressers. In my world, it’s a term of endearment, not an insult. I use the terms interchangeably in this article mostly because “sissy” is fun to say, and they love hearing that word. It’s like candy sprinkles to a sissy.
3Yes, I know. Don’t flame me about gender stereotypes. This refers to a “female point of view” as the CD perceives it—which is usually within the stereotype.
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