Playing the Hand I Was Dealt with Style...
My Experience with Gender Dysphoria

In another story, I made mention of: “Proto me, not being able to withstand the testosterone onslaught during gestation.”
When I was born, gender dysphoria wasn’t a thing. We were told that boys have a penis, girls have a vagina and that’s that. Of course it was a thing, but it didn’t have a clinical definition and even though it does today, for some reason it’s still something of a debate.
Gender Identity Disorder was added to the DSM-3 in 1980. This term was replaced by Gender Dysphoria with the publication of the DSM-5 in 2013.
The earliest evidence of transvestism can be found in Greek and Norse Mythology. Although there’s a hard line drawn between transvestism and transgender, other than ancient rituals and festivals, there are reasons why many play an alternate role. Even those who have no intention of identifying as the opposite sex are often cited as feeling a welcome release from limiting gender expectations.
Gender dysphoria is defined as: A marked incongruence between one’s experienced/expressed gender and assigned gender, as manifested by at least six of the following (one of which must be the first criterion):
A strong desire to be of the other gender or an insistence that one is the other gender (or some alternative gender different from one’s assigned gender)
A desire - YES, but it's more like embracing a part of me that's already there. Insistence about being another gender, no.
In boys (assigned gender), a strong preference for cross-dressing or simulating female attire; or in girls (assigned gender), a strong preference for wearing only typical masculine clothing and a strong resistance to the wearing of typical feminine clothing
In an everyday sense, any semblance of alternate dress and ornamentation is a way of being which I prefer.
A strong preference for cross-gender roles in make-believe play or fantasy play
For me, sensual and sexual experience is heightened by expressing emotion, feelings and my feminine being at the heart which is how I really feel inside. I've been told that I touch like a girl, kiss like a girl and emote like a girl. I don't put any thought into this, it can't be role play.
A strong preference for the toys, games or activities stereotypically used or engaged in by the other gender
Even though I spent some of my younger years in competitive sports, I’d much rather have meaningful conversations with my female friends than drink beer and yell at a television, shoot guns or drive a 4x4 pickup.
A strong preference for playmates of the other gender
Liberated women are so much more engaging, both mentally and physically.
In boys (assigned gender), a strong rejection of typically masculine toys, games, and activities and a strong avoidance of rough-and-tumble play; or in girls (assigned gender), a strong rejection of typically feminine toys, games, and activities
Not a fan of division, hate, war, boxing, ultimate fighting or any activity that involves hurting people in any way other than D/s roleplay.
A strong dislike of one’s sexual anatomy
You’ll read more about this later.
A strong desire for the physical sex characteristics that match one’s experienced gender
It’s more a way of being than the secondary sex characteristics, but yes… I love feeling pretty and looking pretty. It’s empowering in a wonderful way.
I did my best to fit in. I played little league baseball and I tried real hard to like cars and trucks. My brother and I sat in the basement at our friend Mike's house and built hot rod model kits.
The boys in grade school were so offensive and I got into lots of fights. Their idea of play was hurtful. For the most part, the girls didn’t act that way. I watched them play and their idea of play seemed preferable to me.
Neither of my parents wanted kids, but ended up having two boys. I’m pretty sure that my mom would have preferred at least one of us to be a girl. She named me Jaime. I took some shit in school for my name alone. There were no other males named Jaime at that time, none I knew of.
In the first temple we attended, I noticed that the men and women were not only separated by a curtain divider, but the men were the only ones allowed to recite prayers and speak aloud. Even at that young age I called bullshit. Where did the men come from? Shouldn’t women deserve the same opportunities to participate? In my mind it was completely ass-backward. The women should have been the honored Cantors, chanting prayers while the men remained silent. Lack of equality is one of the many reasons why I’m an atheist.
My mom realized that I had a gift for art at a young age and I’m happy that she took it upon herself to foster it. After grade school on the days I didn’t have Hebrew school she would drop my brother and I off at Fleisher Art Memorial. It was an incredible formative experience in many ways. I got to draw, paint and learn pottery at a wonderful non-profit organization run by volunteer art teachers from the best art schools in Philly.
My pottery class was taught by a woman named Rachel. She had a mop of curly black hair and an amazing smile. I asked for her help a lot. The closer I could get to her, the better. Rachel smelled like patchouli and at that time I had no idea what it was, but I loved it. I admired her. Not because she was pretty, but because she was teaching something she was absolutely passionate about. She had a glow that I could feel. At that age, I’m almost certain I’d never met anyone with such enthusiasm. She appeared to be a magic, otherworldly being and I was sad when my class with her ended.
The first time I ever kissed a girl was in the fourth grade. Her name was Tracy. She was quiet and kept to herself. She sat next to me. I liked her a lot and I couldn’t help but steal a glance of her from time to time. She caught me on occasion, and most of the time I would quickly look away, or down at my desk.
One day when she caught me, I was so guilty I had to smile and to my surprise… she smiled back. That day, while everyone was at lunch, I went back up to the classroom. I think I was just trying to distance myself from a bully who wouldn’t stop bothering me.
I walked into the empty room and a moment later I heard a voice behind me say, ”wanna play a game?” There she was with a mischievous smile on her face.
She pulled me over to the coat closet, pushed me in and closed the door behind us. I was nervous. I found myself sitting in the back corner of the closet on the floor in the dark and she kneeled down in front of me. Before I knew what was going on, I felt one of her hands on the back of my head and the other on my shoulder as her lips pushed gently into mine. She tasted like strawberries. I was shocked.
She said, “Do you want to do it again?” I said yes. She said I wasn’t allowed to touch her and she needed to do something first. She rolled her strawberry lip-gloss around her lips and then around mine. In the 1970’s it was all the rage. It was called Kissing Potion. When she leaned forward, pushed me into the corner and began kissing me, something changed.
It was so much more than my first real kiss. Her warm, sweet wet lips pushed across mine and in that moment, I belonged to her. Without realizing it, I touched her side with my hand and she stopped and leaned back. “What did I tell you?” I’m sorry I said. I told her I liked the way her jacket felt. She wore a burgundy satin baseball jacket. She said “Okay, keep your hands on my sides and don’t move them.”
I promised, but just before we were about to kiss again, the rest of our classmates started coming into the room. Suddenly I was scared to death that someone would find us. She put her hands on my shoulders and said, “Ssshhhh… just be quiet.” I relaxed as she pushed me back into the corner and we started to kiss again. I had the feeling she’d done this before.
Lost in her lips, fifteen minutes passed in an instant and before we knew it, the bell rang.
This signaled the beginning of art class, and our teacher led our classmates down to the art room. Again the room was empty and we emerged from the closet. It was bright, I was dizzy and stumbled around, still in shock. Tracy grabbed my hands and said, “Listen, this is our secret and you can’t tell anyone! Okay?” I agreed, wiped my sticky face on my shirt and we ran down to art class.
That fall, I wasn’t sure what I should be for Halloween. Getting dressed up for Halloween was one of my absolute favorite things. Up until then, I’d been Casper the Ghost, a devil complete with plastic pitchfork and a pirate with a sword and flintlock pistol.
I was freaking out because I couldn’t come up with anything and my friends would be around to meet me in a couple hours to make the rounds and collect our sugar laden bounty. My mom brought up the idea of doing some gender bending and I don’t remember having any objections.
She had a gold sequined cocktail dress, sheer nylon pantyhose and a bra that she stuffed some socks into. She had some heels that matched which just about killed me. This was my first time in heels. She did a fabulous job with the makeup and the finishing touch was an old rabbit fur jacket.
My friends and neighbors had no idea it was me. I should have been clued in at that point, but it wasn’t acceptable for anyone to be anything other than their assigned sex at birth. A costume sure, no one would think twice... but it was just a little too exciting. I got to be pretty for the first time in my life and... I - loved - every - second - of it.
It was a cute dress, but I’m definitely not a fan of sequins. I respect drag kings and queens, but I wouldn’t have any interest in doing that. Sequins remind me of drag, over the top outfits and exaggerated makeup. Sequins are also sharp and scratchy.
When I got to high school, I needed some sort of outlet and thanks to a few friends I found the Grateful Dead. I wore very colorful, comfortable clothing, smoked pot, drank gallons of shroom tea, and danced at every opportunity. I had the pleasure of meeting and dancing with some amazing hippy girls and I cherished witnessing them blossom into the earth goddesses they were meant to be.
I admired the flowing dresses, the angel sleeves, the velvet bell bottoms, the ornamentation and the way they moved. The stars in my heaven.
I think it was the second year of high school when my grandma passed away. She lived with us and no one had the heart to go through and clear out her things. I would sneak into her room from time to time and rummage around in her closet. There were boxes and boxes of stuff. Family mementos and remnants of a long, eventful life.
One day I was pushing things around in her dresser and my hands felt something that sent a lightning bolt to my brain. It was a dark blue 1950’s heavy nylon slip. I held it in my hands for a moment and then quickly folded it up and ran to my room. I had a 2x4 that I used to brace the door closed which I shoved in place. I tore off all my clothes and slid the slip over my body. The sensations that it sent through me made me remember Tracy, her satin jacket and those wet, wild and wonderful kisses.
I started going to thrift shops, looking for things that felt good to wear underneath my regular clothing. I was self conscious and embarrassed and I felt like there was something wrong with me.
There’s nothing wrong with being sensual.
What most people think of when you say the word sensual is sexual pleasure, but that’s not what I mean. Even though the definition of sensual references that potential quality, sensuality is primarily a gratification of the senses and the pleasure that comes with experiencing your senses fully.
I had a traumatic eye injury when I was young which rendered me completely blind for two years. This happened the year after I started attending the Fleisher Art Memorial. At just the moment where I started waking up to the beauty of the natural world, the sunrises and sunsets, the colors of nature, the subtlety of human interaction… I lost it all.
It was far and away my darkest hour. I was laying in a hospital bed with second and third degree burns across my face and at 7 years old, overheard the doctors telling my parents it was unlikely that I’d ever see again.
Thanks to a few eye surgeries, skin grafts and glasses with lenses that were as thick as old Coke bottle bottoms, I eventually regained my sight and my face healed about the way it should. I can tell you without hesitation that I’ll never take the sense of sight for granted. I treasure shapes and colors, watching the way the wind blows the leaves around and all manner of mundane things that simply don’t register with a majority of people. To the point where the simple things can make me super emotional inside.
My brother is the consummate audiophile. He introduced me to all sorts of music. Eventually, I picked up the electric bass and I wasn’t good at it, but I played bass, keyboards and sang in a garage band. I have an armada of African Djembes and attended several workshops on African Drumming. Like any hippy worth their tie dye, I go to drum circles occasionally and I delight in the sounds of nature.
The olfactory sense isn’t particularly sharp, but one of the reasons why I love cooking is the aroma of various herbs, spices and seasonings. I can still smell the musk of a woman and I can sense female pheromones. I just can’t deal with most perfumes and colognes. If anything, they completely turn me off. I’ll always be a sucker for sandalwood and patchouli though.
If it wasn’t already clear, I have a tactile thing. Everything from wet sand flowing through my fingers at the beach, feeling the bark on a tree or petting dogs and cats. The texture of finer fabrics against my skin makes my entire body tingle. It’s a shame that society still doesn’t accept men who dress in a comfortable and sensual way. Most fabrics that go into men's clothing are like 60 grit sandpaper.
Satin and nylon are a kink that's often associated with gay men. One thing I understood early on was that I’m not gay. I’m open minded enough that I’ve had a few experiences with men and haven't ruled it out, but you’d have to be a naturally effeminate or androgynous man to scratch the surface of my attention.
I love everything about women and I can wax poetic. I don’t consider men and women equals. I always thought women had better mental and physical qualities, but that doesn’t mean a man and a woman can’t be equals in mutually respectful friendships and partnerships.
I really don’t like most men. There are lots of self-centered, immature assholes out there, endearing to women who are not in full possession of themselves. It's safe to say that I have a healthy misandry for men. Who started most wars? Who enslaved others? Who are quick to judge, quick to anger and slow to understand? In my mind, men are guilty until proven innocent.
What I love about women is that they can change their mind like the wind, be outwardly emotional and change their look at will. They’re allowed to be colorful, soft and sensual or righteous, fierce and absolutely badass.
Other than the fact that it functioned as represented in the advert, I’ve never liked my body. I've grown full beards a few times which didn’t look half bad, but I’d rather be clean shaven. I have an 8 o’clock shadow 1 minute and 3 seconds after shaving and my body hair is relentless. It’s a constant, losing battle. The only hair I like is the hair on my head. Most of my life, I've had long brown hair with uneven sandy tones.
I remember standing next to my dad when I was really young, the both of us taking a piss at the same time. I remember seeing his junk and thinking about how weird and ugly it looked. It was always an impediment. Having your genitalia on the outside doesn’t seem like a good idea.
When I went to college, I decided to go to art school.
The first student I met, who I mentioned in another story, became a friend, and my first mistress. Her name was Amy. She lived with a fashion design major named Leah who was her primary partner in a D/s relationship. Amy strongly preferred female companions although her desire to play the dominant role was absolutely genderless.
She took delight in the forensic investigation of her subjects' deviant desires. She used physical touch, discipline, bondage, denial and all your senses to drive you absolutely insane. Amy had a gift that was so powerful and seductive that if she wanted to, she could get anyone to do anything. Thankfully that didn’t include robbing banks or killing people.
Amy made me wear lingerie under my clothes in art school. I certainly got some looks with saucy leggings showing through torn jeans and my old flat front motorcycle boots.
Her partner Leah and I became good friends. I finally found someone who loved to role play, dress up and go bending in public with me. We would make the thrift shop rounds together and create complex alternate identities for each other. We would get really deep into character and go to the Copa Banana on South Street for drinks. We were hysterical.
Amy was a player on the Philly kink scene back then. She couldn’t spend as much time doing that with the demanding school schedule, but she carved out as much time as she could to attend events.
I’m afraid she lost a ton of street cred because of me. Her friends in that scene were almost exclusively gay and lesbian. There was no LGBTQIA at that time, only L & G. They had a mutual distrust for each other and a mutual dislike of bisexuals. Not only did I not fit, but on 2 occasions I became the subject of not so quiet criticism. Although I'd been respectful, it seemed that I wasn't welcome in her circles. Amy’s submissive subjects were always female until I came along.
I felt like an imposter, an unwelcome outsider. It hurt then and it still hurts now.
I’m sure Amy didn’t feel good about that either. To her credit, she never took it out on me. Invariably, when you see D/s relations in movies or read about them in mainstream books involving the dominant female as a top and a feminine trap as a bottom, there always seems to be a strong element of humiliation involved.
That’s a crying shame.
If you ever set out into these waters, there’s something you need to know. A submissive is not inferior to their mistress or master. They are not lesser or weaker. In fact, being able to give oneself fully requires courage and an inner strength that not everyone has, excellent communication and a great deal of mutual respect. It’s about learning to understand and respect each other's needs and desires.
A good top doesn’t just tear their bottom to bits and walk away. They listen very carefully, respond thoughtfully, respect boundaries and provide good quality aftercare. I was in awe of Amy and Leah. I got to watch as Amy would draw a bath for Leah and cradle her in her arms. It wasn’t just a check in, it was a moment to honor the strength and courage it took for Leah to give herself completely and a sincere thank you for helping fulfill Amy’s desires.
Not sure how I fell into kink, but I know it’s not a natural progression for those who deal with gender dysphoria.
Thanks to a few friends, I discovered the burn community. It’s kind of like what being a dead head was like for me with the option of being able to present in just about any way without judgement. I’ve met people who represent every facet of LGBTQIA+ and lots of really nice cis-gender people as well.
At one of the burns I wore a torn black t-shirt, these luscious long black satin and lace bloomers that were custom made by a wonderful seamstress and my oxblood Doc Martens. I made a big black furry wolf tail that hung off a belt in the back. My nails were black with rainbow sparkles. I got a bunch of compliments.
The Halloween before Covid hit, I 'came out' to some old friends. Elliott and Stephanie throw a Halloween party almost every year and I decided to go as a rave girl. I wore a skin tight cropped Suzi Fox white liquid vinyl t-shirt with a neck collar, a matching white circle skirt, white fishnets under calf high, white vinyl lace up platform gogo boots with those fuzzy white leg warmers. A friend did rainbow hair extensions and makeup for me. I finished it off with a mess of beaded rave candy wrist bracelets.
When I walked in, none of my friends knew it was me. They were shocked and I was simply stunning. All the guys just stood there while the girls and I danced to funky tunes like Groove is in the Heart. It was a special moment. The guys still don’t know what to make of it.
Was it a costume or something more? The girls loved it, but no one had the balls to ask.
Would I ever consider gender reassignment? I’m over 50 years old and I think that ship has sailed.
It’s refreshing to see people starting to acknowledge gender dysphoria in a more broad sense. One day, I hope I can be me in public. I have no interest in going out everyday full on sissy… but to simply be comfortable. To wear my harem pants, tank top and sandals. Nothing unusual for women in the warmer months, but you should hear the shit I get at the local beer distributor.
“What are YOU supposed to be?!”
I dunno… anything I feel like?
About the Creator
Jaime Winter
I have a life filled with weird and wonderful experience. I am a writer, a graphic designer and crafter.
I hope you enjoy my stories and my perspective. Much Love, Jaime
Contact: [email protected]


Comments (1)
Hi Jamie - So sorry I've missed this - I've been following your eclectic stories but haven't seen you around. This reminds me of a story I've written - with an entirely different slant - but I've so enjoyed yours thank you for sharing you are a marvelous StoryTeller. btw; Someone is stealing our stories and posting them as theirs. This has happened to my "Popsicle" Verbatim. Please check your precious original offerings to see if this has happened to you; it has been done to over 44 of us. Our Judey has been so very helpful (see comments under her TOP 'Plagiarism') - So nice that our little Village has one another's back. Jay Jay Kantor, Chatsworth, California 'Senior' Vocal Author - Vocal Author Community -