meowjennie
Virgin
- Joined
- Sep 12, 2020
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Preface: Crossdressing isn’t a monolith. It’s a sensitive and complicated subject, and well beyond the scope of this post to address every single reason that a person might crossdress. I speak only from the perspective that I have personal experience with, which is a cis male who normally presents as masculine but fully presents as feminine on occasion with a desire to be as “passable” as possible. Many crossdressers don’t dress fully, or don’t desire to pass, and that’s perfectly fine. It’s possible that you don’t agree with what I have to say, in which case please open a dialogue so that we can better understand each other!
One of my earliest memories is going into my mom’s room to put on one of her dresses; it was so long that I could barely walk in the thing. Even though I didn’t quite know what I was doing, I knew it was “wrong,” so when my mom came to her room to look for me, I tried to keep her out by pushing against the door with all of my five-year-old strength. My memory is murky after that but I can only assume I got a scolding and a firm explanation that dresses were for girls and not boys.
Over the years, the compulsion got stronger. When at a friend’s house I might opportunistically steal a piece of clothing from their sister, not because I wanted to do anything lewd with it, but because it was pretty and I wanted to wear it. In junior high, I bought my first piece of girls’ clothing: a cute striped halter top from a retail store, nervously lying to the curious cashier that it was for my (fictitious) girlfriend.
In college I got a real girlfriend, and of course that meant I would secretly borrow her clothes to wear. On one occasion, she dropped by the dorm to surprise me and I refused to see her because I had been experimenting with her eyeliner and couldn’t figure out how to get it off. I lied and told her that it was because I hated surprises, and she cried. It was the first time my secret had spilled over into “real life,” and the consequences were very real.
Eventually I was able to move into a studio apartment of my own. Away from prying eyes, I purchased awful wigs, heels that were either too big or too small, fashionable clothes that would literally rip at the seams when I tried to squeeze into them, and makeup that didn’t match my skin tone. Nonetheless, I was in love with all of it, because it was the first time I could transform from head to toe into the girl that I wanted to look like. I relished the sensations of tight spandex, silky polyester, and delicate lace, and when looking in a mirror after a few glasses of wine, imagined that I almost looked pretty.
It was chasing this feeling of prettiness that led me to make an account for my femme persona on a dating site. In my mind, the highest form of validation of my feminine appearance was the interest of another guy. At that point, I knew deep down that I still wasn’t very passable as a girl, so I was incredibly flattered when this tall, fit, gentleman with a great smile invited me on a movie date. Up until that point, I had only ventured around the block dressed up under the cover of darkness, so it sounded like a grand adventure to be able to experience being a girl for a night in public. Tentatively, I agreed.
My date was very sweet, and didn’t mention my broad shoulders, narrow hips, or square jaw, even though I got more than a few curious or alarmed looks from other people. By the end of the night, I was extremely confused. It sounds silly and naive but I hadn’t ever considered the possibility of having sex with a guy, but I was so caught up in feeling like a girl that I wanted to go home with him. This deviates from the majority of crossdressers, who are straight, but I ended up losing my virginity a second time that night.
I’ll never know what happened to him after that, because as soon as I got home I deleted my dating profile and tossed all of my girl stuff into the dumpster.
Many crossdressers will likely be familiar with “purging,” or getting rid of all their girl stuff. Purging is usually triggered by being or nearly-being “caught,” and wishing to avert embarrassment or as part of a compromise, the crossdresser resolves to never again indulge in such behavior. For me, my first purge was triggered by the terrifying realization that I might not be completely straight. I told myself that if I simply never crossdress again, I could live out the rest of my life as the regular straight dude that everyone thought I was. Perhaps over time, I wouldn’t even want to crossdress anymore.
For a few years, it almost worked. I would catch myself being a little too interested in the racks of clothes when shopping with my girlfriend, or spending too much time admiring a cute girl’s outfit on Instagram, but would immediately quash any stray thoughts. Eventually, a really bad breakup shattered my vow of abstinence, and I splurged to fully restock my feminine closet almost overnight. This time, I told myself, it’d be different: I had gotten all of that bisexual stuff out of my system.
Of course, that was a lie. I liked girls, and I had no romantic interest in men, but when dressed up I would nonetheless find myself seeking their validation. I had become the very kind of girl that I disliked: insecure and attention-seeking.
Queue several cycles of hooking up with a guy, purging out of guilt and shame, a period of abstinence, only to cave again.
At some point I realized the futility and wastefulness of it all—the desire to crossdress had begun when I was but a wee tyke and would remain with me until the day I died. Purging and abstinence were ineffective in eliminating or even reducing the urge. There are some parallels to be drawn with alcoholism: the compulsion will always be there, though it can be suppressed.
But did I need to or even want to suppress it? An alcoholic destroys both himself and his relationships with the people who care about him, but I wasn’t harming anyone with my hobby, and though filling up two closets was more expensive than filling one, I was able to afford it. I could either continue to unsuccessfully fight it, or learn to embrace it in a healthy way.
I was able to choose the latter, but it’s not difficult to imagine situations where the choice becomes much more difficult. Perhaps a crossdresser was caught by their partner, who can’t accept it and delivers the ultimatum of either giving up crossdressing or separating. Or perhaps a crossdresser lives in a part of the world where their job or even safety can be at jeopardy if they’re ever discovered. I’m fortunate that these aren’t factors for me.
Today, I’m free to become Jennie whenever I wish. By embracing my feminine side and shedding the guilt and shame, I’m a happier and more complete individual. I can talk about my feelings more deeply and more openly. I’m more sensitive to the needs of others. As an added bonus, my complexion has significantly improved when I discovered feminine skincare, and it’s also a powerful motivation for me to stay in shape and stave off the dad-bod so that I can continue to fit into the girl clothes I own.
Are there other crossdressers on Literotica who can relate to any of this? I've started a crossdressing blog and am very interested in different perspectives on the subject. It's difficult to get people to speak candidly about crossdressing, even on the internet, but I thought I'd give it a try.
-Jennie
One of my earliest memories is going into my mom’s room to put on one of her dresses; it was so long that I could barely walk in the thing. Even though I didn’t quite know what I was doing, I knew it was “wrong,” so when my mom came to her room to look for me, I tried to keep her out by pushing against the door with all of my five-year-old strength. My memory is murky after that but I can only assume I got a scolding and a firm explanation that dresses were for girls and not boys.
Over the years, the compulsion got stronger. When at a friend’s house I might opportunistically steal a piece of clothing from their sister, not because I wanted to do anything lewd with it, but because it was pretty and I wanted to wear it. In junior high, I bought my first piece of girls’ clothing: a cute striped halter top from a retail store, nervously lying to the curious cashier that it was for my (fictitious) girlfriend.
In college I got a real girlfriend, and of course that meant I would secretly borrow her clothes to wear. On one occasion, she dropped by the dorm to surprise me and I refused to see her because I had been experimenting with her eyeliner and couldn’t figure out how to get it off. I lied and told her that it was because I hated surprises, and she cried. It was the first time my secret had spilled over into “real life,” and the consequences were very real.
Eventually I was able to move into a studio apartment of my own. Away from prying eyes, I purchased awful wigs, heels that were either too big or too small, fashionable clothes that would literally rip at the seams when I tried to squeeze into them, and makeup that didn’t match my skin tone. Nonetheless, I was in love with all of it, because it was the first time I could transform from head to toe into the girl that I wanted to look like. I relished the sensations of tight spandex, silky polyester, and delicate lace, and when looking in a mirror after a few glasses of wine, imagined that I almost looked pretty.
It was chasing this feeling of prettiness that led me to make an account for my femme persona on a dating site. In my mind, the highest form of validation of my feminine appearance was the interest of another guy. At that point, I knew deep down that I still wasn’t very passable as a girl, so I was incredibly flattered when this tall, fit, gentleman with a great smile invited me on a movie date. Up until that point, I had only ventured around the block dressed up under the cover of darkness, so it sounded like a grand adventure to be able to experience being a girl for a night in public. Tentatively, I agreed.
My date was very sweet, and didn’t mention my broad shoulders, narrow hips, or square jaw, even though I got more than a few curious or alarmed looks from other people. By the end of the night, I was extremely confused. It sounds silly and naive but I hadn’t ever considered the possibility of having sex with a guy, but I was so caught up in feeling like a girl that I wanted to go home with him. This deviates from the majority of crossdressers, who are straight, but I ended up losing my virginity a second time that night.
I’ll never know what happened to him after that, because as soon as I got home I deleted my dating profile and tossed all of my girl stuff into the dumpster.
Many crossdressers will likely be familiar with “purging,” or getting rid of all their girl stuff. Purging is usually triggered by being or nearly-being “caught,” and wishing to avert embarrassment or as part of a compromise, the crossdresser resolves to never again indulge in such behavior. For me, my first purge was triggered by the terrifying realization that I might not be completely straight. I told myself that if I simply never crossdress again, I could live out the rest of my life as the regular straight dude that everyone thought I was. Perhaps over time, I wouldn’t even want to crossdress anymore.
For a few years, it almost worked. I would catch myself being a little too interested in the racks of clothes when shopping with my girlfriend, or spending too much time admiring a cute girl’s outfit on Instagram, but would immediately quash any stray thoughts. Eventually, a really bad breakup shattered my vow of abstinence, and I splurged to fully restock my feminine closet almost overnight. This time, I told myself, it’d be different: I had gotten all of that bisexual stuff out of my system.
Of course, that was a lie. I liked girls, and I had no romantic interest in men, but when dressed up I would nonetheless find myself seeking their validation. I had become the very kind of girl that I disliked: insecure and attention-seeking.
Queue several cycles of hooking up with a guy, purging out of guilt and shame, a period of abstinence, only to cave again.
At some point I realized the futility and wastefulness of it all—the desire to crossdress had begun when I was but a wee tyke and would remain with me until the day I died. Purging and abstinence were ineffective in eliminating or even reducing the urge. There are some parallels to be drawn with alcoholism: the compulsion will always be there, though it can be suppressed.
But did I need to or even want to suppress it? An alcoholic destroys both himself and his relationships with the people who care about him, but I wasn’t harming anyone with my hobby, and though filling up two closets was more expensive than filling one, I was able to afford it. I could either continue to unsuccessfully fight it, or learn to embrace it in a healthy way.
I was able to choose the latter, but it’s not difficult to imagine situations where the choice becomes much more difficult. Perhaps a crossdresser was caught by their partner, who can’t accept it and delivers the ultimatum of either giving up crossdressing or separating. Or perhaps a crossdresser lives in a part of the world where their job or even safety can be at jeopardy if they’re ever discovered. I’m fortunate that these aren’t factors for me.
Today, I’m free to become Jennie whenever I wish. By embracing my feminine side and shedding the guilt and shame, I’m a happier and more complete individual. I can talk about my feelings more deeply and more openly. I’m more sensitive to the needs of others. As an added bonus, my complexion has significantly improved when I discovered feminine skincare, and it’s also a powerful motivation for me to stay in shape and stave off the dad-bod so that I can continue to fit into the girl clothes I own.
Are there other crossdressers on Literotica who can relate to any of this? I've started a crossdressing blog and am very interested in different perspectives on the subject. It's difficult to get people to speak candidly about crossdressing, even on the internet, but I thought I'd give it a try.
-Jennie
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Loads of elements in there that chime with my own story.
Your underlying femininity really comes out.
