It was a long way into my kinky journey before I had given the proper amount of thinking to why I have always enjoyed the sight (and very idea!) of boys who like “girly” things. I didn’t grow up in the modern times we now find ourselves in, where gender is fluid, and crosses boundaries rarely imagined before, all as a way of self expression, comfortableness, identity, and a lifestyle. Many of us remember the “boy” and “girl” toy aisles very blatantly separated, variations of 50 shades of blue and pink galore.
This, I believe, is where the substructure of my alpha female personality started to form. I didn’t intend to have a particular disdain for all things “girly”, I just did. I had waist length hair that I refused to wear down most of time, even when my parents insisted on pigtails, of all god awful hairstyles. I didn’t wear dresses, the closet full of them gathering dust and stretching on my broad little shoulders. Nail painting, makeup, heck Barbies (whose hair I would shave and dye various colors with fingernail polish) were not something I was mildly interested in. Well into my teens I still considered myself a tomboy even with my beauty pageant awards tucked away behind Nirvana posters and lava lamps.
I wouldn’t say I hated being a girl but I certainly didn’t enjoy it the way most girls seemed to. I couldn’t get myself to get too excited, we couldn’t even pee standing up (!), a problem GoGirl finally attempted to fix. ‘What was so great about being a girl anyway’ I would ask myself constantly.
It wasn’t until I met the most girly boy I knew in college that it all started to click. His name was Evan but I called him ‘Eve’ often. He was beside himself at not being a girl.
‘You don’t know what you’re missing’ he’d sigh and say wishfully looking through my unopened high heel boxes and gifted lingerie. Finally, one day I asked him what being a girl would mean to him.
‘So, let me make you a girl’ I offered one day. His reaction was that of someone who had just opened the door to Ed McMahon holding a fated Publishers Clearing House check. (Does anyone remember those?). He jumped up and down, speechlessly squealed and nodded until I thought his neck was going to fall off and then he started to playfully beg – the light bulb in my head didn’t just light up, it exploded.
What followed was a series of trials, errors, and lots of fun finding the feminine that was deeply hidden inside of myself through a boy. He let me have free range of his ‘Eve’ side as we called it. He didn’t say no to anything and even suggested things I hadn’t even considered.
He was my first sissy doll and I didn’t even know it!
I’ve long since gotten in touch with my feelings behind sissies, crossdressers, and just generally boys who like to (and deserve to) feel pretty and have tried to spread my view on this wherever I can. I don’t speak for all cis-females who have an affinity for a nice pair of legs in stockings belonging to a male, I am only sharing what I find draws me in this direction.
Flattery will get you everywhere (maybe even in my panties)
I know it takes a lot of “balls” for a male identified person to take the leap to dress up as the superior sex and I am flattered by that. The pains of bras, lacey panties, garter belts, stockings, heels, and not-poking-yourself-blind when applying nearly all makeup can only fully be appreciated once you’ve experienced it. Since entering the kink community, I have been able to chat, play with, and get to know some really amazing boys who like to dress up as girls. I’ve been a part of several transformation processes from beginning to end, feeling nothing but pride at the end results. For me personally, growing up it was a lot easier for me to “act like a boy” and get away with it, than the majority of men I’ve met whose femme side was stifled, shamed and even forbidden! I like to think every boy who wants to, and gets to express his girly side (big or small), is finally being given permission to find his power.
…I present to you…
Ahh the great reveal. This…this is when I get the most enjoyment out of watching boys in dresses do their thing. Try as hard as I might, I can never really imagine a man as their female self. Even when I’m the one crafting/creating the look! How they will walk, what style of clothes they choose, the hair (OMG the hair), if they will opt-out of certain feminine aspects, and even the shades of makeup applied, all speaks to my creative roleplay and costume side. There’s still a part of me that gets overjoyed at costume parties, playing dress-up, and looking at a “new person” in the mirror when it suits me. Gender bending is the beacon of that in my eyes.
Girls just wanna have fun
I can’t think of a time that I’ve witnessed a man dressing up as a female who didn’t express the rush often associated with such. Especially if they went undetected! Not every boy who dresses up wants to “pass” but for those who do or at least fly under the radar it can be a glimpse into an unfamiliar, yet very real world they currently live in. Some of the people I’ve spent time with who cross these self-imposed, societal reinforced lines for the first time ever experience something new and exciting. They can partake in activities, conversations, roles, and go places mentally and physically uncharted to them. My sissy has no interest in being treated like a lady until he’s dressed in his sissy side and then he wants all the stops haha – door holding, chair pulled out, slutty pet names, and more. It’s fun to see how “she” would like to be treated.
It’s just fucking hot
I’ve come to learn I just like boys in panties and more. I’m so used to wearing these items myself that it’s a flip of my senses to feel it on another. Have you ever watched as pantyhose stretched to contain an ever growing…er…excitement? Or how those new to lipstick still hold their lips slightly pouted out while wearing it? The tiny, purposeful steps taken when the wearer isn’t adept at heels…yep all of this tickles my lady loins. Finding out two exes of mine were secretly dressing up without me because of the response they’d gotten from previous partners was heartbreaking and also a missed opportunity for us to connect.
Without Evan, I never would have blossomed into the stiletto nailed, heel wearing, garter belt owning, makeup enthusiast I am today. It took a boy who liked girly things to teach me how awesome it was to honor my feminine power within. In a system that is slowly undoing the design to work against women, it’s always been a fresh breath of air to encounter someone who willingly shares that power with me despite everything being told to them of the contrary.
I know not all femdoms, or any one for that matter, is into the non-humiliating aspect of boys dressing up but I am. I also know for those guys who are dressing, whether undisclosed or not a big fear is being found out. I’ve seen the authentic reveal of this ruin relationships, break trust, create an unseen sense of shame through judgement, and worse – breaking up and alienating friends and family.
This post is for those people.
You’re not alone. There are other men who like the very same and maybe more than you do. There are executives donning satin underwear in meetings, Dads who have a favorite lipstick color, boyfriends who prefer eyeshadow to mowing the lawn, and guys who get a rush when they put on a wig and see someone new in the mirror. And for each one of those, there is a female out there who will not only admire but embolden you to embrace that side of yourself. They love you for you. And if they don’t…fuck em’.
About the Author
d20domme is unapologetically kinky after over 10 years in the community. She is known as pint-height, poly(androus), plus-size, POC, 24/7 Femdom who knows what she wants and will use her craft in mindfuckery and persuasive viper tongue to get it. Her main kink is normalizing kinky lifestyles across the board and thus she can often be found writing on her blog From Mundane To Mistress, chatting away on podcasts, teaching classes, demos, or presenting locally in the Washington, DC area, New York, and sometimes across the pond in Europe.