Dedication: This story is dedicated to my very dear friend – she knows who she is. Thanks for letting me write this story.
Disclaimer: My goal in writing this story was to contrast decisions and lifestyle choices, not to make value judgments against or to disparage anyone working in the sex industry. In fact, as I wrote it, it occurred to me that writing erotic fiction and publishing it in a public place might technically make me a sex industry worker, too, except I don't get paid for it. Other than "intangible benefits", of course.
Gotta love those intangible benefits.
This story is fictional, so any resemblance to any persons, in real life or elsewhere, is probably intentional on my part and the result of way too much imagination on your part. But at least I changed the names and embellished a little just to make it harder to recognize anyone.
Asako by Stephanie Silver
I heaved a heavy sigh as I slid beneath the sheets of our king-sized bed and snuggled up next to Dennis. It was two o'clock in the morning.
"How'd it go with Asako?" he asked.
I kissed him softy on the lips, not surprised to find him awake. My hand brushed across his dick, and lingered there, hoping to feel it respond. It did. I sighed again, "Dennis, my kid-sister's gonna be a whore."
Asako Harris is my kid-sister. Half-sister, actually. We're separated in age by about fourteen years, I guess. So in some ways, I was more like a mother to her. Not that our mom wasn't there. Not at all. Mom was always there when we needed her. But, I guess having a fourteen-year-old around means you have a built-in babysitter, which allowed Mom to work out of the house and bring in some needed extra money.
I won't even bother to go into the subject of our dads. Dads!? When did we ever see them? Asako's dad, Slater, was in a motorcycle gang. He had tattoos all over his chest and all the way down his right arm. He wore nothing but dirty blue jeans, a leather vest, and whatever t-shirt he happened to find in his closet that morning. Most of the t-shirts were x-rated, with pictures of nearly naked women on the back of flaming motorcycles with guys that looked just like him.
My dad, Bill Clarington, was a very respectable banking manager who wore ties and clean-pressed suits to work each morning, screwed the tellers at lunch, and then embezzled funds in the afternoon. He's in jail now, without any of those pretty young girls he was so fond of screwing on his lunch break, the victim of less-than-stellar embezzling practices. He got caught, in other words.
And somewhere on the way I got messed up too. I guess. I mean, some people would call me messed up. I'm happy with the way I turned out. I'm transgendered. Half-male, half-female. And don't tell straight people this, but I wouldn't want to be anything else. The best of both worlds.
Although sometimes I think it's more like the best of neither world.
Asako's dad had a thing for Japanese. Japanese food. Japanese culture. Japanese motorcycles. I think he's the only biker I know who didn't ride a Harley. So when Asako was born, Slater insisted on giving her a Japanese name. Even though neither he nor my mom are Japanese.
That left me taking care of Asako. I don't know. Maybe that contributed to my gender confusion. It was kind of like playing house, only I got to pretend I was the mom. Or maybe gender confusion was just something that was bound to happen one way or the other. I tell people, when they ask me why I want to dress and act like a girl, I didn't choose it; it chose me.
Asako was the girlhood I never had. By taking care of her, I got to experience all the things I missed by being a boy. I got to play with dolls. I didn't wear her clothes, and, once she was old enough, I didn't see her when she changed clothes. But I did the laundry, and occasionally picked out things for her to wear for the day, so I was always familiar with what she was wearing. I saw my little sister progress from diapers to cartoon undies to training bras to sexy lingerie. Those experiences only fueled my interest in dressing that way myself.
Asako was a year away from being a teenager when I finally worked up the nerve to tell Mom that I wanted to start living full-time as a woman. Surprisingly, Mom wasn't that surprised. Actually, I think she was somewhat relieved that it was finally out in the open. When I told her I wanted to save up my money for SRS, she supported my decision without hesitation.
Naturally, coming out the way I did included telling my kid-sister. She accepted it the same way, "Now I'll have a big sister," she said with a grin.
By the time Asako was sixteen, we were going on shopping trips together: swooning over shoes, sorting through five-for-ten panties, and trying on outfits in the dressing room and then getting one another's opinion. We became best friends. Well, as close as two sisters can be when one's sixteen and the other is dreading the arrival of her thirtieth birthday.
Our new-found closeness also included boy talk. Since I continued to live close to Mom and Asako, it was easy for her to stop off at my place on her way home from school for a talk. Mom had a social life of her own, so I often found myself back in the role of taking care of my kid-sister, making her dinner or picking her up after field hockey practice or whatever else needed to be done. It was more than once that I would call Mom at some point and let her know that Asako was sleeping over.
Weekends were when that happened the most. With neither of us needing to get up early the next day, some of our talks lasted until well past midnight.
We even double-dated a couple times. I still remember the time we went skating. As a trans-female, it's tricky to know when to tell someone your full history. Telling them too soon means telling a lot of people who really don't need to know; waiting too long risks offending them by not being completely "truthful". The result for me was a lot of "forgetful" dates: dates where I realized about half-way through the date that there was no attraction and so no reason I'd ever consider telling them my history.
This particular double-date was one of those "forgetful" ones. Whenever we talk about it, we both can recall the tiniest details, from what the weather was like, to how the popcorn smelled on the boardwalk where we were skating, to what movie was playing at the theater we passed by. But neither of us can remember the name of the guy I was dating. We just call him The Guy We Don't Remember. We do remember that he got blisters on his feet from his rented skates, and he looked so funny sitting there on that park bench, his pant legs rolled up, rubbing his feet and talking on his cell phone.
"Probably calling for a taxi," I giggled to Asako, who laughed louder than was appropriate. It turned out to be one of those bonding moments, when we both suddenly realized that guys might come and go in our lives, but our love for one another would last forever.
And then there was Craig! Craig was Asako's first real boyfriend. He was also the first guy to break her heart. He was also a jerk.
Craig, Craig Hatch, was just weird. I never knew what exactly attracted Asako to him. It was obvious what he saw in my baby sister. And every time I saw that particular look in his eye, my old male characteristics would come back and make me just want to kick him in the nuts. Or something. I'm sure a dad could explain it better than me, but I know it had something to do with that instinct fathers have to protect their little girls from... Well, from guys like Craig.
He was a travel writer, which meant he actually had more in common with me than he did with my sister. One day, when something happened that Asako couldn't make their date at the last minute, I ended up having a long talk with him about our common interest: writing. I'd never told Craig that I was transgendered and didn't plan on telling him - to me he wasn't on the short list, and my intuition said he never would be - and I knew Asako wouldn't tell anyone without checking with me first. So when the conversation got around to what genre of writing I did, I settled for a partial truth: erotic fiction. I didn't see a need to tell him I specialized in transgendered erotic fiction.
The conversation moved to the importance of having a good beginning to a story if you wanted to keep a reader's interest, and I shared with him the beginning from one of my stories that I thought had a good beginning. It went: "Three years ago I married my best friend. Often, a statement like that is the beginning of a wonderful love story. In this case, it's the beginning of a very strange one."
Craig was one of those know-it-alls. Or at least he thought he knew it all. The trouble with most know-it-alls is they usually don't know it all, and are usually clueless what things it is they don't know. He wasn't the least bit shy about sharing his opinion and giving the impression that only a fool could possibly disagree with him. Which, I suppose, was the biggest reason I had for disliking him: I almost always disagreed with him.
But I kept quiet and let him talk. It's not in my nature to argue with someone over something as meaningless as a difference of opinion. And, no matter how I felt about him, he was still Asako's boyfriend, and that meant I had to be nice to him.
One day, a few weeks after our talk on writing, he asked me how that story was going that I told him about, and if I'd ever managed to add anything to the beginning I'd shared. I can only say that I was amused, because it showed how little he actually paid attention. "I finished that story almost two years ago," I told him. "I was just telling you how it started."
Craig and Asako stopped dating not long after that. I wasn't surprised. I wasn't surprised when he did it in the most classless and insensitive way possible: he just quit calling her. One day everything was fine; the next day it was all over. Only Asako didn't know that. Each day, when she talked to me and told me that he still hadn't called her, I remembered the way I'd seen him looking at me that last time, with the same leer he normally reserved for Asako or some other gal when he thought no one was watching. And despite all his perceived intuition and self-proclaimed ability to "read" people, I knew he still had no idea I was transgendered. Frankly I felt she was better off without him. But I didn't say that to her, and never would. I was nothing but supportive.
Losing Craig gave Asako some emotional issues of her own. I don't know. Probably they were always there, and losing Craig simply brought them to the surface. One day she confessed to me that she was bisexual. "Oh really?" I asked, "How do you know?"
It was a simple enough question. Her answer should have been something like, "Because I'm attracted to girls as much as I'm attracted to guys." But I had to ask because, unless she'd completely avoided the subject with me somehow, I hadn't gotten a single clue that she had any interest in girls sexually.
Of course my little sister was just trying to find herself. I suspect that being bisexual was just a way for her to somehow punish Craig. Only Craig, by that time, didn't care. With nothing really coming of her bisexuality, she eventually moved on to something else.
One warm summer day as we sat watching the sky darken from an approaching storm, Asako turned to me and said, "Suzi, I think I'm trans, too."
I looked at her skeptically. "What?"
"I want to be a boy," she said.
"A what!? I've spent my whole life trying NOT to be one of those disgusting creatures, and now you're here in my house telling me you want to give up your wonderful, sexy female body to be the very thing I couldn't stand being!?"
No, I didn't say that. I only thought it. It wouldn't have been supportive. And just then, Asako needed my support and understanding more than she needed a lecture. "How can I help?" I asked.
Asako made a cute boy. We cut her hair short and gave her a unisex style. We went shopping for some boy clothes for her. We found a few of my old boy things at Mom's house and gave her those. I thought of all the things I'd done over the years to make myself more feminine, and tried to figure out how to do the opposite. We wrapped her 34C breasts tightly with a surgical bandage to keep them from showing. I had her wear loose-fitting clothes. We took off all her makeup.
It didn't work. Asako is a naturally pretty girl. She ended up looking like a girl in boy clothes. Her tightly bound breasts looked as if they were just straining to get free. Her eyes, her eyelashes, her cheeks, her delicate fingers. There just wasn't anything manly looking about her. If anything, she looked even sexier as a boy than she did as a girl. As if trying to cover it all up simply emphasized the very things she was trying to hide. But I never told her that. Any of it.
Mercifully, that phase lasted only a few months, and one day she showed up at my apartment wearing a short skirt and low-cut top. I noticed the change, but didn't say anything. A few days later she added nail polish and makeup. And by the time the weather turned cold, there was no trace of that boy she claimed to have inside her.
Somewhere in all of Asako's confusion I met Dennis. All I can say is it was... not forgetful. No, I won't go so far as to say it was love at first sight. It took three or four sightings, at least.
I think the magical moment for me came one day when I saw him talking to another girl. I'd been helping Melanie Fox fill out a job application for the place I was working at, and was in a room just off the front lobby when I heard Melanie say, "Oh Dennis, I was just about to call you and see where you were. We need to be at that party in less than an hour."
It was the name Dennis that got my attention, since we had been on a few dates by then, so I peeked out, and there he was. He hadn't noticed me, and I decided not to say anything as I watched him with Melanie. She wrapped her arm around his elbow and pulled him close as they promenaded to the parking lot. I couldn't decide if he looked uncomfortable with her or not, although when she stopped to light up a cigarette, I was sure I detected a distinct frown.
Why did I care? Why did my heart skip a beat when I heard his name? Why did I secretly hope Melanie would fall into a manhole before they got to his car?
Two days later, when he hadn't called me, I decided to call him, using a totally unrelated issue as an excuse for calling. That business took only a few minutes, and I casually changed my tone to a friendly chat. "I saw you at my office the other day," I said.
"You did?"
"Yeah, you were there to pick up Melanie."
"Oh, her." His tone was non-committal and even.
I decided to act, for the moment, as if she was his girlfriend and that I didn't mind. "She's very pretty," I said. Which was true.
"She smokes too much," he said. "I hate smoking."
"Did you let her smoke in your car?" It was a trick question. I knew she couldn't have possibly finished her cigarette before they'd gotten to his car.
"It was her car," he said. "She just asked me to drive. Mine's in the shop for a few days."
And suddenly I knew I wanted him. Except I still hadn't told him my history. We made a date for that weekend, and on a balcony overlooking a bend in the river just after sunset I took a deep breath and told him my secret.
"I don't care," he said at length. "I still want to be with you."
And we've been together ever since. I slowly introduced him to the TG world, and learned that he's the most tolerant, accepting and caring man that I could ever hope to meet. He accepted all of my TG friends without hesitation. And, well, the sex is incredible.
Meanwhile, Asako was still going through emotional issues. After deciding to go back to being female, she suddenly became very clingy. At a time when I kind of needed some space to work on my relationship with Dennis. That clinginess was something new, something I'd never seen in her before. And it was hard for me to deal with. In hindsight, I realize that Craig had hurt her more deeply than I imagined. My normally self-confident sister had suddenly grown indecisive and needy.
Asako started asking to borrow some of my favorite outfits, and even buying things that were exactly like things I had in my closet. As any girl can tell you, wearing the same outfit as another girl anywhere makes us uncomfortable, and Asako was stretching my patience with her insistence on looking just like me. In another situation I might have said something, or simply refused to cooperate, but I sensed that Asako was going through some difficult times, and the best thing I could do was agree.
Besides, I was finding myself getting very comfortable with Dennis. If being my little sister's twin was all it took to make her happy, it didn't matter to me. The three of us started going clubbing and stuff together, and I would spend the evening dancing with Dennis while Asako made her own friends. I found it really didn't matter that we were wearing the same outfit.
That changed one day when we decided to go to a costume event at one of my favorite TG clubs, Le Parc. The theme was Victorian and Steampunk. Neither of us knew what steampunk meant, so we decided to go shopping for something Victorian. That wasn't much better, but at least we had some idea what we were looking for.
When I found the perfect dress at Freed's Formalwear, I knew Asako would want the same thing. It was a bit pricey and beyond her budget, but I knew it meant a lot to her, so I offered to buy it for her. "Just pay me back when you can," I said, knowing I'd never see the money. What did I care about money? This was my baby sister's feelings we were talking about. Money didn't matter.
The dress was black lace, with an open-front skirt revealing a shorter skirt underneath. The lace bodice was semi-transparent below an opaque bra, with empress sleeves and gloves to match. With black lace-up boots, it was guaranteed to turn more than a few heads.
On the day of the party we decided to go skating together and then go back to my place and change into our new gowns. Skating had become one of our favorite activities since we discovered a nice trail near the river where we could skate and talk and enjoy each other's company. The fact that it did so much to keep our bums looking tight, firm and sexy only added to our enjoyment. We'd even joke sometimes about how sexy we were getting, and how the boys wouldn't be able to keep their hands off of us.
When we got back to my apartment, Asako started changing while I took a semi-urgent phone call from my office. When I finally got off the phone, Asako was already dressed. She walked out and let me see how she looked by doing a slow twirl.
I was stunned. My baby sister looked absolutely gorgeous! The black lace against her black hair was a perfect match, drawing attention to her dark eyes and slender figure. "Hold still. I have to get a picture," I insisted.
As I snapped a picture of my very beautiful sister, I suddenly realized one thing. I couldn't wear that same outfit. Not for my usual selfish reasons of wanting to be unique, but for just the opposite reason: I didn't want to detract from her. To this day I've never been able to wear that gown. It hangs in my closet, unused and unworn. It's my dress, but it belongs to Asako.
Fortunately, because we didn't have time to go shopping again, I had managed to collect a small assortment of gowns, so I quickly sorted through those for an alternative. Shopping for clothes is a girl's guilty pleasure, and I enjoyed it as much as any other girl. Maybe more. I had a dark blue taffeta gown with a huge ruffle skirt and a strapless top that I realized would just match the summer hat I had bought only a few days earlier. I bought the hat because I liked it without really thinking what I'd ever be able to wear it with. Buy first, think later, right? The look was probably more Southern Belle than Victorian, but it would do in a pinch.
Okay, I have to confess that I look better in blue than I do in black anyway. With my blonde hair and light skin, black tends to make me look washed out while blue does just the opposite. But it's more fun to think I had noble, sisterly reasons for giving up the black gown.
Asako won the prize that night for best Victorian outfit – a $500 gift certificate at the mall. She made a couple of new friends, and spent the night dancing with at least one of them. I noticed it as we were leaving and more so over the next few weeks: Asako changed that night. She regained her old self-confidence and became independent again. It was the last time we talked about wearing the same outfit.
As I began stroking Dennis's erection, he replied, "Nothing wrong with being a whore."
I was quiet for a moment, not sure if I disagreed with him or not. I was pretty sure I was a slut. My girlfriends from the club and I practically reveled in our strong sexual urges. Bawdy jokes there were perfectly normal and almost expected. Calling each other and ourselves sluts and whores was a form of affection. And there was no question the stories I wrote and published on-line were intended to arouse and titillate. Were the things I did that much different from what she was doing, just because I didn't make any money doing it?
Dennis's pole swelled beneath my touch to its full length, reminding me of the pole Asako had spent most of the night wrapping her legs around as she danced and climbed and slid back down again. I slid my hand up and down, mimicking the movements I'd watched her performing earlier. "You don't think it's wrong to charge people for it?"
Dennis sighed, which could have indicated either his lack of interest in a philosophical discussion at two in the morning, or enjoyment at what I was doing to his cock. I glanced at his face, but with his eyes closed it was still hard to tell. "Do you want me to suck you?" I asked.
"Yes."
It wasn't really a question. I knew he always wanted that. And I liked doing it. Asking was nothing more than a way of telling him. I opened my mouth and wrapped it around his cock. Dennis rewarded me with another sigh. "That feels good, baby," he said.
I looked up at him without taking my mouth off of his cock. His eyes were open now and he was watching me. I made sure he was able to get a good view of his cock in my mouth as I thought about the guys who had been watching my sister dance. Was it the same look? A look of silent appreciation?
"Take off your top," he said after a minute.
I obeyed by climbing on top of him and lowering the upper portion of my smooth cotton chemise, slipping my arms through the straps and letting the fabric bunch around my waist. I rocked softly backward and forward, feeling his erection beneath me as I waited for Dennis to take it all in with his eyes.
"I love seeing your tits," he said as he reached up to begin fondling them.
"I like showing them to you," I admitted, savoring the delicious feel of a man's eyes on my breasts. I wondered if Asako got that same feeling whenever she took her top off in front of a pair of appreciative eyes. Or pairs. How could she not? It had to be exciting for her.
I leaned forward to find the radio next to the bed and turned it on so I could dance. The movement brought my slowly hardening nipples near Dennis's hungry mouth, and his response was exactly what you'd expect. I gasped. Having my nipples sucked has always been the easiest way for me to orgasm as a woman. "Ooo yeah, make me cum," I urged.
Asako's nipples had gotten hard more than a few times, I recalled. Was there any way to fake that? None that I knew of. Cold water, of course, but, the Climax Club, where Asako worked, had been warm. Hot even. Of course I'd been wearing clothes the whole time. Maybe it was different if you spent the night naked or nearly naked as Asako had done. Somehow I didn't think so.
Dennis's hands were snaking their way up each of my thighs, pushing my skirt higher as he exposed my black cotton panties trimmed with white lace. I closed my eyes, savoring the sensations.
Asako had started off each set with a short skirt, her hands eventually finding their way beneath it to caress her bare flesh. It was extremely erotic to watch, even for me. I could only imagine how much the guys had enjoyed it. I'd glanced around at them a few times. Perverts. They all wanted just one thing, to see my baby sister take her clothes off.
Just like the pervert beneath me at that moment. The one whose hard dick was pressing up against my crotch. The one I was in love with. The one I wanted to give myself to before either of us went to sleep. I opened my eyes and looked at him, half expecting to see one of the faces from the crowd at Climax staring back at me. I saw Dennis. I was putting on my own private strip show for him.
When he tried to pull my panties off, I stopped him. "Pay me a dollar first. And put it in my panties." I had to know how it felt.
Dennis chuckled, thinking I was kidding. "You're serious?" he asked when he saw I wasn't laughing.
I pushed my skirt back down, covering myself and then began covering my breasts. I wanted sex, but I wanted respect more. If Dennis wasn't going to do what I asked, I wasn't going to let him continue. At least in theory. If he hadn't scrambled off the bed to find his wallet, I might have changed my mind.
His actions reminded me of the guys I'd watched scrambling for their wallets when Asako had stripped to nothing more than a g-string. I remembered the words her manager had told her earlier, "If they don't pay, you don't play. Got it?"
At the time his words had chilled me. They seemed so heartless. So mercenary. So devoid of intimacy. In hindsight, I think it just brought home to me the personal nature of what was going on. Asako was making her start as a stripper in the sex industry. Whatever her feelings, or mine, about sex, this wasn't about sex. It was about money. It was business. "If they don't pay, you don't play."
"Shit!" Dennis growled, "All I got are twenties."
"Watch your language," I reminded. "And twenties will be fine. I was expecting hundreds."
My words surprised me. I said it wanting to make the point that I should be worth a lot to him. What surprised me was how little difference there was, really, between what I expected of him and what Asako expected of her customers. In fact, I seemed to expect more from Dennis than she did from them. Did that make me a whore?
I hardly knew what to think. Dennis came back with two twenty-dollar bills. I got on top of him again, my breasts exposed, and rubbed my panty-clad crotch on his cock, which had grown soft again. When I felt him starting to respond once more, I pulled the chemise all the way up over my shoulders so that I was wearing only panties.
Asako had needed to dance close to each guy with a folded-up dollar bill in his hand, suggestively wiggling and swaying her shapely ass, enticing them to put the money inside her g-string. I realized I needed to give Dennis a similar hint. I tucked my fingers inside the waistband of my panties and pulled it out slightly, showing him where I wanted the money.
He hesitated. He really did. I had to smile. It was so cute. I had no intentions of keeping his money. I just wanted his commitment. But he didn't know that. Finally, after I guess deciding I was going to be an expensive lay that night, he tucked the first bill into the left side of my panties. The second bill, on the right side, he gave up without much fight.
And then I kissed him. As our lips parted, I whispered, "Now take them back out."
He took the money back, but only after reaching inside my panties to play with my pussy first. A moment later he rolled me onto my front and helped me take my panties off. The two twenty-dollar bills lay forgotten as our passion mounted.
I love how Dennis's cock feels when he enters me. It's the perfect size. "Smooth as butter" is the only way I can describe it. This time I lay flat on my tummy as he mounted me from behind, keeping my legs close together as he got on top. It's my favorite position, but one I can only do with him without working up to it first. I moaned as I felt his cock go up inside me. That has to be the most delicious feeling there is.
Dennis began thrusting, taking several minutes to reach his climax. As he did, he pushed forward, his cheek next to my ear. "I'm cumming, baby, here it cums."
And it did. I felt his cock twitch inside me. I felt complete. I felt satisfied. I had everything I wanted.
"Keep it," he said, when I handed Dennis back his money the next morning. "You deserve it."
"I can't," I said. I didn't add the part about taking money for sex making me feel like a whore.
He looked at me for a moment, his eyes burning a hole in my soul. I think, in that moment, he understood. I'm not sure I did. "It's not for the sex," he said finally. "It's just `cause I like you."
"Oh. Okay, that's different," I said, and took the money.