So, for example, if I were told to dress up like a woman, it wouldn't be humiliating. I don't enjoy it, and I look ridiculous dressed as a woman. I have a very masculine body, and a hairy one at that. I have no intention to shave (and I'm not allowed to. Wife will cut me.), and so I will never look even remotely passable. So cross dressing doesn't appeal to me, and I don't find it particularly humiliating, at least not in a fun way. It's just ridiculous. Now, licking boots is humiliating, and I love doing it. But as much as I love it because it's humiliating, it's also humiliating because I love it.
For today's story, we have someone who DOES like dressing like a woman. Who IS proud of himself as a woman, and who DOES understand that there is nothing wrong with wanting to be a woman. Being transgendered is not something that should be shunned or considered to be a bad thing. But if you cross dress in public, piece by piece, that is going to be humiliating. But in a good way. A fun way.
Changing at the MallI took a deep breath and looked at myself in the rearview mirror. My skin looked good, freshly shaved. My eyebrows were plucked, and my hair was nice and short. My tie was straight, my suit as good as such a cheap suit could look, and the messenger bag I bought still clean and simple looking. I checked inside for the breast forms, the wig, and the teasing comb for adjusting that wig.
I locked my keys in the car. Now there was no way to run away; I either admitted that I couldn't do it, or I did it and showed off. No other way to get back in the car, no other way to get home.
It's a long walk to the door of the mall. There just weren't that many spaces open by the time I pulled in. At least I didn't have to do this on Black Friday or something like that. It's busy, but not ridiculous.
The first thing I do is the makeover. That's the one that will draw the most attention, that will make it most clear what I'm doing. Yes, other people will see. Yes, I'm doing this in public. But there's nothing wrong with any of it. People who are upset at seeing a man dressed as a woman need to get over themselves. They won't; they'll point, they'll stare, and they'll snicker at me. They'll whisper, thinking I won't hear. Some might even yell. But that's ignorance on their part. There's nothing wrong with what I'm doing.
The girl at the makeup counter is young. Probably still in high school, or was until very recently. I'm not sure if that's a good thing or a bad thing. She's attractive, but she probably doesn't have the social graces to not – oh fuck it. Here goes.
I sit down in the chair and smile at her.
“Can I help you?” she asks, looking around as if expecting to see my wife walking around somewhere, and me just the annoyed husband taking a seat during a marathon shopping trip.
“Yes,” I say. “I need a makeover.”
She laughs, as if unsure how else to react. Very nervous. But not judgmental. Not yet, anyway. “Um,” she says, “I've never really worked on a man before. I'm not entirely sure what I can show you. Some skin care, I guess. But you have really nice skin, so I don't know if--”
I hold up a hand. “I don't want that,” I say. And just as her eyes are starting to fade, just as she starts seeing a commission go racing away, I smile at her. “I want you to give me a makeover as if I were a woman,” I said. “Makeup that will bring out the color of my eyes, that will hide any blemishes in my skin, and that will go well with my hair.”
She smiles, understanding. “And what color is your hair going to be?”
“Blonde,” I say. “Platinum blonde.”
“I can do that.”
“Don't be subtle,” I say. “And ring me up for whatever you decide to use.”
She smiles even wider at that. The dollar signs are almost visible in her innocent, doe like brown eyes. “You're the boss,” she says.
I get the first stares on my way out of the department store. Here I am, wearing a cheap suit, cheap but formal and very obviously masculine shoes, carrying a messenger bag, with a very female face. The girl at the makeup counter, Terry, told me that I was just on the edge of looking slutty, and that it was a look that could work both day time and at night. It was all on how I played it and what I wore with it. She asked if I was going to be wearing the suit. I had promised her I hadn't intended to. Not for long.
She smiled and wished me a happy day. But that was before I left the store. I haven't gotten a smile since. At least, not a kind one.
The next store on my list is literally as far away as possible. I have to walk the whole length of the mall dressed very obviously like a man, with my face very obviously made up like a woman. I get some confused looks. Some smirks. Some mocking smiles. A lot of whispering, the occasional pointing, and a lot of children saying the rude things that adults couldn't get away with. It's easier to ignore the children. They don't understand, they're innocent. There's nothing cruel in their rudeness. Hearing their parents explain that I'm just a confused man, or that there's something wrong with me, or that I'm sick and they should never talk to anyone like me; that hurts a little. But I'm not here to change minds. I'm here to change clothes.
In the second department store, I find a very nice light pink blouse and a tie made of rhinestones. I check that they are my size, pay for them, and then go put them on. I'm still wearing my suit jacket, but there's no doubt what's going on anymore, even if no one looks at my face. The tie is all sparkly, hanging loose around my neck, and it draws attention. I guess it draws the attention away from my face. That makes it a bit less embarrassing.
I frown at scold myself for that kind of thinking as I stuff the original shirt and tie, the man's clothing, in a trash can outside the department store. What I'm doing isn't something to be embarrassed about. It's freeing. I should be enjoying myself. I should be accepting who I am, who I want to be. Next time I come shopping, it will be entirely as a woman, and entirely for women's clothing. This time I am going through the transfer for all to see. Let them be uncomfortable. I need to be proud.
Which is why the next thing I buy is a bright pink leather purse. One with lots of shiny metal on it, one that has a small strap. I put the strap up on my shoulder, not across my torso like the messenger bag was. Everything from the bag is now in my purse. I gave the bag to a kid outside the store. He had to be a teenager, and he was laughing so hard at me that it made my ears burn. But when I offered him the bag, he took it. He asked what the catch was, but eventually he took it. Called me a fag, too.
I sighed, but I didn't say anything back.
Across the mall is another department store. Before I get there, though, there's one of those stores specifically for younger girls. Not children; college girls and older women who are trying to look like they're twenty-one. Which is probably why it's called Forever 21.
I get a lot of looks in there. Girls are cruel, especially at that age. They point at me and laugh openly. The women shake their heads in disgust. At first, no one comes over and asks if I need help.
But one of them, finally, gets the courage to do it. “What are you looking for?” she asks.
I look at her name tag. Morgan. “I need a new jacket,” I say. “One that matches my shirt and my purse better.”
She nods and leads me over to a selection of jackets. At first, she points out jackets that might be for men or for women. Then she stops herself and looks at me again. “You don't want something unisex, do you?”
I shake my head. “Not even close.”
She smiles. Then she walks over and grabs a half jacket off a rack. It's leather, light gray. It has sleeves, but the jacket cuts off just below them.
“Something like this will help give the illusion of curves,” she says. “It's like layering shirts on top of each other.” Morgan points down at herself. She has a long sleeved shirt, her thumbs poking through the sleeves. On top is a t-shirt that doesn't go down far enough to cover the first shirt. There's a third underneath all three, showing only at the bottom. “See?” she says. “It gives the illusion of curvy hips without having to get fat.”
I laugh at that, at the casual way she talks. “Do you work on commission Morgan?” I ask.
She nods, her smile fading just a little bit.
“Let's go with the jacket then,” I say. “And show me some shirts to help with the effect.”
I keep the blouse and the tie; they are cute. But once I have the three shirts -a pale tan on the bottom, long sleeved brown, and bright pink on top- and the jacket on, I toss my suit coat. The shirts are snug, but Morgan assured me they would stretch if I needed them too. She gestured at my chest when she said that. And she said it with such a smile that I had her bring me over to look at shoes.
We settled on a pair of pumps the same color as my coat, with simple stockings I wasn't planning on keeping. It was a bit delicate to balance, and she offered to help me up. I smiled at her and told her that it wasn't my first time in heels.
By the time she rang me up, Morgan was as chatty as anyone else. “You really look great,” she said. It made me wish I could tip her.
Here, in this third department store, I already miss her. I'm getting more double takes than before, as people see the whole picture. But without breasts, without feminine hair, I still look like a man. Too much so. And the pants aren't helping.
So I have to do something about them. I've never really realized just how many options there are when it comes to women's clothing. I mean, I knew the sections for women were always at least two or three times the size of the areas for men's clothes, but even that never really did it justice. If I want pants, I have to decide between slacks, jeans, stretch pants, yoga pants, capri pants, and others that I just don't even have words for. And even within each category, there are sub categories. Do I want boot cut jeans? Low cut? High cut? Hip huggers? Maybe I want cargo pants. Do I want the ones that add curves or the ones that subtract them?
No, I'm not going into all that. Too complex. And it feels like a cheat. I don't want to walk out of here wearing pants. I want as skirt. And not a long flowing one, either. But I also don't want a skimpy short skirt. This isn't getting dressed on a dare. I'm not trying to look like a slut. I'm sure that will come in time. But right now, I want something comfortable.
Something like a pencil skirt with a nice slit up the side. One with pin stripes to help me look skinny. A skirt that matches my coat and my pumps.
And if I'm going to wear a skirt, I can't keep wearing boxer briefs. I need panties. A cheap pair for now.
Once they're paid for, I go back to the changing room and try everything on. I like the feel of the panties, the feel of the stockings, and the feel of the skirt. But there's something wrong. I turn around and see what it is: the lines of the panties. They're all wrong. They show through the skirt. Well, that won't do.
Victoria's Secret has some nice stockings, one with long stripes that go along with my skirt. And they have thong after thong after thong. And garter belts to hold up the stockings.
The hard part, though, is the bra.
Eventually, I get the courage to ask for help. I'm expecting something rude here. Something where the woman insists that they don't help men. That they won't help a sissy. That I'm disgusting, pathetic, and wrong.
But she doesn't do that. She's very kind and helpful. The only question she asks is for a cup size. I show her the breast forms. She leaves me in the changing room, comes back a few minutes later with a perfect bra.
“Let's get this on you,” she says. “Now be honest with me. If the straps are too tight, we can loosen things a little. It's important that this be comfortable. Otherwise, you're going to spend all day itching, or pulling at it, or something like that.”
We get the breasts on with the bra, and she helps me adjust everything. “You are beautiful,” she says. “You make a very pretty woman.”
I smile at that. “Better a woman than a man.”
“I don't know,” she says, looking me up and down. “I bet you're a pretty man too.”
I shrug. “I'd rather be a pretty girl.”
She smiles and asks if I have a wig. She helps me put it on, helps me adjust it, and then stands back to admire me, giving me the chance to admire myself in the mirror. “Like I said,” she tells me, “beautiful.”
I didn't need extra bras or panties. But there is plenty of room in the purse now, and she deserved the commission.
My last stop is right where I started. I walk up to Terry and ask her if my makeup still looks good.
She smiles at me, then her jaw drops. “Holy shit,” she says. “Is that you?”
I nod. “You like?” I do a little twirl so she can see the full effect.
Terry laughs. “Amazing,” she says. “You look great.”
I smile at her, give her a wink and a light girly kiss on the cheek.
The way back to the car is still long, but it's a much nicer walk than the way in. I'm taller, and I feel taller, more so than just the heels. There's a big smile on my face, and the looks I get aren't of disgust anymore. The whispers aren't followed by laughter. When a girl looks me up and down with a mean look on her face, I know that she isn't thinking that I'm a pathetic sissy who shouldn't be allowed in public like that.
She's thinking what a bitch I am for having better legs than she does.
That makes me laugh all the way back to the car. It's unlocked when I get there, and there's an envelope on the seat. Inside the envelope are pictures of me. Pictures of me coming in to the mall, pictures of me at each store. Pictures of every step of my transformation.
I locked my keys in the car. Now there was no way to run away; I either admitted that I couldn't do it, or I did it and showed off. No other way to get back in the car, no other way to get home.
It's a long walk to the door of the mall. There just weren't that many spaces open by the time I pulled in. At least I didn't have to do this on Black Friday or something like that. It's busy, but not ridiculous.
The first thing I do is the makeover. That's the one that will draw the most attention, that will make it most clear what I'm doing. Yes, other people will see. Yes, I'm doing this in public. But there's nothing wrong with any of it. People who are upset at seeing a man dressed as a woman need to get over themselves. They won't; they'll point, they'll stare, and they'll snicker at me. They'll whisper, thinking I won't hear. Some might even yell. But that's ignorance on their part. There's nothing wrong with what I'm doing.
The girl at the makeup counter is young. Probably still in high school, or was until very recently. I'm not sure if that's a good thing or a bad thing. She's attractive, but she probably doesn't have the social graces to not – oh fuck it. Here goes.
I sit down in the chair and smile at her.
“Can I help you?” she asks, looking around as if expecting to see my wife walking around somewhere, and me just the annoyed husband taking a seat during a marathon shopping trip.
“Yes,” I say. “I need a makeover.”
She laughs, as if unsure how else to react. Very nervous. But not judgmental. Not yet, anyway. “Um,” she says, “I've never really worked on a man before. I'm not entirely sure what I can show you. Some skin care, I guess. But you have really nice skin, so I don't know if--”
I hold up a hand. “I don't want that,” I say. And just as her eyes are starting to fade, just as she starts seeing a commission go racing away, I smile at her. “I want you to give me a makeover as if I were a woman,” I said. “Makeup that will bring out the color of my eyes, that will hide any blemishes in my skin, and that will go well with my hair.”
She smiles, understanding. “And what color is your hair going to be?”
“Blonde,” I say. “Platinum blonde.”
“I can do that.”
“Don't be subtle,” I say. “And ring me up for whatever you decide to use.”
She smiles even wider at that. The dollar signs are almost visible in her innocent, doe like brown eyes. “You're the boss,” she says.
I get the first stares on my way out of the department store. Here I am, wearing a cheap suit, cheap but formal and very obviously masculine shoes, carrying a messenger bag, with a very female face. The girl at the makeup counter, Terry, told me that I was just on the edge of looking slutty, and that it was a look that could work both day time and at night. It was all on how I played it and what I wore with it. She asked if I was going to be wearing the suit. I had promised her I hadn't intended to. Not for long.
She smiled and wished me a happy day. But that was before I left the store. I haven't gotten a smile since. At least, not a kind one.
The next store on my list is literally as far away as possible. I have to walk the whole length of the mall dressed very obviously like a man, with my face very obviously made up like a woman. I get some confused looks. Some smirks. Some mocking smiles. A lot of whispering, the occasional pointing, and a lot of children saying the rude things that adults couldn't get away with. It's easier to ignore the children. They don't understand, they're innocent. There's nothing cruel in their rudeness. Hearing their parents explain that I'm just a confused man, or that there's something wrong with me, or that I'm sick and they should never talk to anyone like me; that hurts a little. But I'm not here to change minds. I'm here to change clothes.
In the second department store, I find a very nice light pink blouse and a tie made of rhinestones. I check that they are my size, pay for them, and then go put them on. I'm still wearing my suit jacket, but there's no doubt what's going on anymore, even if no one looks at my face. The tie is all sparkly, hanging loose around my neck, and it draws attention. I guess it draws the attention away from my face. That makes it a bit less embarrassing.
I frown at scold myself for that kind of thinking as I stuff the original shirt and tie, the man's clothing, in a trash can outside the department store. What I'm doing isn't something to be embarrassed about. It's freeing. I should be enjoying myself. I should be accepting who I am, who I want to be. Next time I come shopping, it will be entirely as a woman, and entirely for women's clothing. This time I am going through the transfer for all to see. Let them be uncomfortable. I need to be proud.
Which is why the next thing I buy is a bright pink leather purse. One with lots of shiny metal on it, one that has a small strap. I put the strap up on my shoulder, not across my torso like the messenger bag was. Everything from the bag is now in my purse. I gave the bag to a kid outside the store. He had to be a teenager, and he was laughing so hard at me that it made my ears burn. But when I offered him the bag, he took it. He asked what the catch was, but eventually he took it. Called me a fag, too.
I sighed, but I didn't say anything back.
Across the mall is another department store. Before I get there, though, there's one of those stores specifically for younger girls. Not children; college girls and older women who are trying to look like they're twenty-one. Which is probably why it's called Forever 21.
I get a lot of looks in there. Girls are cruel, especially at that age. They point at me and laugh openly. The women shake their heads in disgust. At first, no one comes over and asks if I need help.
But one of them, finally, gets the courage to do it. “What are you looking for?” she asks.
I look at her name tag. Morgan. “I need a new jacket,” I say. “One that matches my shirt and my purse better.”
She nods and leads me over to a selection of jackets. At first, she points out jackets that might be for men or for women. Then she stops herself and looks at me again. “You don't want something unisex, do you?”
I shake my head. “Not even close.”
She smiles. Then she walks over and grabs a half jacket off a rack. It's leather, light gray. It has sleeves, but the jacket cuts off just below them.
“Something like this will help give the illusion of curves,” she says. “It's like layering shirts on top of each other.” Morgan points down at herself. She has a long sleeved shirt, her thumbs poking through the sleeves. On top is a t-shirt that doesn't go down far enough to cover the first shirt. There's a third underneath all three, showing only at the bottom. “See?” she says. “It gives the illusion of curvy hips without having to get fat.”
I laugh at that, at the casual way she talks. “Do you work on commission Morgan?” I ask.
She nods, her smile fading just a little bit.
“Let's go with the jacket then,” I say. “And show me some shirts to help with the effect.”
I keep the blouse and the tie; they are cute. But once I have the three shirts -a pale tan on the bottom, long sleeved brown, and bright pink on top- and the jacket on, I toss my suit coat. The shirts are snug, but Morgan assured me they would stretch if I needed them too. She gestured at my chest when she said that. And she said it with such a smile that I had her bring me over to look at shoes.
We settled on a pair of pumps the same color as my coat, with simple stockings I wasn't planning on keeping. It was a bit delicate to balance, and she offered to help me up. I smiled at her and told her that it wasn't my first time in heels.
By the time she rang me up, Morgan was as chatty as anyone else. “You really look great,” she said. It made me wish I could tip her.
Here, in this third department store, I already miss her. I'm getting more double takes than before, as people see the whole picture. But without breasts, without feminine hair, I still look like a man. Too much so. And the pants aren't helping.
So I have to do something about them. I've never really realized just how many options there are when it comes to women's clothing. I mean, I knew the sections for women were always at least two or three times the size of the areas for men's clothes, but even that never really did it justice. If I want pants, I have to decide between slacks, jeans, stretch pants, yoga pants, capri pants, and others that I just don't even have words for. And even within each category, there are sub categories. Do I want boot cut jeans? Low cut? High cut? Hip huggers? Maybe I want cargo pants. Do I want the ones that add curves or the ones that subtract them?
No, I'm not going into all that. Too complex. And it feels like a cheat. I don't want to walk out of here wearing pants. I want as skirt. And not a long flowing one, either. But I also don't want a skimpy short skirt. This isn't getting dressed on a dare. I'm not trying to look like a slut. I'm sure that will come in time. But right now, I want something comfortable.
Something like a pencil skirt with a nice slit up the side. One with pin stripes to help me look skinny. A skirt that matches my coat and my pumps.
And if I'm going to wear a skirt, I can't keep wearing boxer briefs. I need panties. A cheap pair for now.
Once they're paid for, I go back to the changing room and try everything on. I like the feel of the panties, the feel of the stockings, and the feel of the skirt. But there's something wrong. I turn around and see what it is: the lines of the panties. They're all wrong. They show through the skirt. Well, that won't do.
Victoria's Secret has some nice stockings, one with long stripes that go along with my skirt. And they have thong after thong after thong. And garter belts to hold up the stockings.
The hard part, though, is the bra.
Eventually, I get the courage to ask for help. I'm expecting something rude here. Something where the woman insists that they don't help men. That they won't help a sissy. That I'm disgusting, pathetic, and wrong.
But she doesn't do that. She's very kind and helpful. The only question she asks is for a cup size. I show her the breast forms. She leaves me in the changing room, comes back a few minutes later with a perfect bra.
“Let's get this on you,” she says. “Now be honest with me. If the straps are too tight, we can loosen things a little. It's important that this be comfortable. Otherwise, you're going to spend all day itching, or pulling at it, or something like that.”
We get the breasts on with the bra, and she helps me adjust everything. “You are beautiful,” she says. “You make a very pretty woman.”
I smile at that. “Better a woman than a man.”
“I don't know,” she says, looking me up and down. “I bet you're a pretty man too.”
I shrug. “I'd rather be a pretty girl.”
She smiles and asks if I have a wig. She helps me put it on, helps me adjust it, and then stands back to admire me, giving me the chance to admire myself in the mirror. “Like I said,” she tells me, “beautiful.”
I didn't need extra bras or panties. But there is plenty of room in the purse now, and she deserved the commission.
My last stop is right where I started. I walk up to Terry and ask her if my makeup still looks good.
She smiles at me, then her jaw drops. “Holy shit,” she says. “Is that you?”
I nod. “You like?” I do a little twirl so she can see the full effect.
Terry laughs. “Amazing,” she says. “You look great.”
I smile at her, give her a wink and a light girly kiss on the cheek.
The way back to the car is still long, but it's a much nicer walk than the way in. I'm taller, and I feel taller, more so than just the heels. There's a big smile on my face, and the looks I get aren't of disgust anymore. The whispers aren't followed by laughter. When a girl looks me up and down with a mean look on her face, I know that she isn't thinking that I'm a pathetic sissy who shouldn't be allowed in public like that.
She's thinking what a bitch I am for having better legs than she does.
That makes me laugh all the way back to the car. It's unlocked when I get there, and there's an envelope on the seat. Inside the envelope are pictures of me. Pictures of me coming in to the mall, pictures of me at each store. Pictures of every step of my transformation.
Under the pictures is a note.
“I'm so proud of you, my pretty little sissy.”
Brrrrrriliant... :) xx
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