The Spurious Sister free porn video

The Spurious Sister © 2019 by Nom de Plume It's one thing to pose as my missing sister to keep the money coming from a distant relative. It's quite another to start living her life.... "Aw Mom, do I really have dress up as a girl?" "Yes Andrew, please don't make such a fuss about it. They're only clothes! And you know how much it will mean to your Aunt Esther." "Does she really think I'm Amy?" "I'm afraid so. I suppose it was my fault, when your father and sister disappeared, not to tell her the truth about Amy, but I could tell she was on the brink of a nervous breakdown when she learned about your father, and I just couldn't bear to tell her that her favorite niece was probably gone forever." My father and sister had been on a three- day cruise to Mexico when a freak tsunami capsized their ship, and they'd been lost at sea. I was two years younger than my sister, and everyone said we looked like identical twins, except for the obvious difference below the belt. "It sucks that you told her I was the one with Dad," I sniffled. I was still feeling guilty about missing out on their ill-fated trip because of yet another run-in with the juvenile authorities. Vandalism, malicious mischief, and other assorted misdemeanors - I was compiling quite a rap sheet for a thirteen-year-old. "I know dear, I did a terrible thing, but you know how much your aunt adored your sister, and thanks to her generosity we've been able to keep this house and not worry about money, so please go along with the charade, just until I can find a job and figure out how to support us, okay?" My Aunt Esther, who lived in New York, was very rich, and I knew she'd become a lifeline for us. She was also half blind, and we hadn't seen her in several years, which were the only reasons my mother's dopey scheme to disguise me might work. One look at Mom's tormented face was enough to convince me to play along with her absurd fantasy. "Okay, if I gotta," I sighed. "But this is the only time." "We'll see," she said ominously. "Please come into my bedroom. I want to show you what you'll be wearing to dinner tonight." "Hey, who said anything about going out?" I whined as I followed her up the stairs. "If anyone in my school sees me, I'll be a dead man!" I figured I could fit into one of my sister's old sweatshirts and a pair of her old jeans, and we wouldn't be leaving the house. I was terrified that I'd be outed by one of my friends. "I doubt if any of the hooligans you hang out with will run into us at Chez Panisse," my mother said snidely. "Today would have been your sister's sixteenth birthday, and your aunt wants to make it a special occasion," she sighed. Once again my resistance melted - until I saw the clothes she'd laid out for me on her bed! Arrayed before me were a dress, with no sleeves and a full skirt, a pile of lingerie including a bra, panties and a slip, and sheer nylon stockings! Even worse, at the foot of the bed was a pair of ridiculously high heels! "There's no way I'm putting on that shit!" I shouted. My mother's slap hit me in the face like the crack of a whip. "Don't you ever speak to me in that tone of voice again, young man!" I was stunned into silence. "Aunt Esther bought this dress for you in New York, and she's expecting you to wear it, young lady!" I felt tears running down my cheeks. "But Mom, I'll never be able to wear this...stuff," I cried. I don't even know how to put it on! And look at those shoes, I'll fall down if I try to walk in them! Please don't make me do this!" "There, there, don't get so upset, dear. I'm here to help you every step of the way. For starters, take off your clothes while I draw a hot bath for you. I'll add some sweet bubble bath, and you can use my razor to shave your legs." "I'm not shaving my legs," I wailed. "Oh yes you are, or I'll shave them for you. Your aunt is expecting to see her niece as a budding young woman, and that's what you shall be. When you're done with your bath, I'll trim those loose ends and try to do something with your hair. I never thought I'd say this, but I'm glad you refused to get it cut for so long." I was shaking with sobs as I collapsed onto the bed. "Please, please don't make me do this," I begged her. "I promise I'll never get in trouble again." "This isn't punishment, dear," my mother said tenderly as she dried my eyes. It's necessary if we're going to be able to survive until I can find some way to support us. If your aunt finds out that I've lied to her, and that you're not really your sister, she'll cut us off completely, and we'll lose this house and be out on the street. Since your father's body was never found, the insurance company is being impossible, you know that. Now please, get with the program and stop wasting time. We only have a few hours to make you presentable and try to teach you how to walk in those heels." I was broken down with misery as I stripped and sank into her tub, which was overflowing with mounds of fragrant bubbles. "And don't forget to shampoo and condition your hair," she reminded me as I hung my head in despair. With a sigh of resignation, I picked up her razor and ran it over one of my legs. I didn't have much hair to begin with, and I was surprised by how easily I was able to whisk it off. Soon both of my legs were sleek and hairless, and I turned my attention to the hair on my head. It was long, almost down to my shoulders, which used to piss off my Dad no end. If only he could see me now, I thought sadly as I squeezed conditioner through my long blond hair. When I couldn't put it off any longer, I dried myself off and strapped a towel around my waist. My mother was waiting for me in her bedroom. "Okay princess, time to get beautiful," she smiled. I remembered how my sister, an incorrigible tomboy, used to complain bitterly every time my mother forced her to put on a dress for church. If only she were here instead of me! "Let's start with your hair. But first, please put on your panties. You can do it under your towel." During my long soak in the tub, I'd decided to employ a passive- aggressive approach to counteract my mother's madness. Thinking it might shock her, I dropped the towel to the floor and waited for her to hand me a pair of panties. Without batting an eye, she picked them up off the bed and waited for me to tug them up my hairless legs. "Oh good, they fit you perfectly," she observed. "When your aunt sent you that dress, I knew I'd have to find you some lingerie to go with it. As you know, your sister was more into jeans and sweatshirts, but I was able to find what I needed in her dresser. Let's put one of her bras on you before we tackle that mop of yours." "What for? I don't have tits." "You will if you want to fit into that dress. Here, hold out your arms." I lifted them a few inches, which was enough for her to slip them under the straps before she snapped the bra shut behind me. It was a bit snug, and the cups were like the collapsed sails of a boat on a windless sea. Before I could get off another wiseass comment, she began stuffing them with knee high stockings until they were nice and snug. "That'll have to do for now," she observed. For now? "Here, let's put on your slip while we're at it." "Why do I have to wear this thing?" "You'll need it under your dress," she said without explanation, as if some secret of the universe known only to females was hidden from me. She dropped it over my shoulders, and I shivered at the feeling of the soft material against my skin while she fussed with the straps. With that, she led me over to her vanity and sat me down. Sitting there in my slip, I watched in the mirror as she deftly snipped my long blond hair after she patiently combed it straight. I said "ouch" every time it snagged, to which she replied, "Welcome to the club, sweetie." When she was finished with the scissors, she took out her blow dryer and went to work with a brush, gently lifting and fluffing my hair until I began to look a little bit like my sister when she wasn't wearing her usual ponytail. "Okay, that will do for now," she said again. For now? "Next, let me see your hands. I held them out and she frowned at my bitten off nails. "I was afraid of this. Fortunately, the problem is easily solved." She opened one of her drawers and pulled out a package of press-on nails. "These should last several days," she said as she methodically applied one to each of my fingers. I was amazed by how feminine the French tips made my hands look. "I can take them off as soon as we come home from dinner, right?" My mother ignored the question. "Before we get you dressed, let's try just a little bit of makeup, okay?" "Amy never puts that sh...stuff on," I stammered. "Well, today you're Amy, and we're going to see how it looks on you." I sat back sullenly as she tried a little eye liner, mascara and lip gloss on me. To my alarm, they immediately changed my whole face, making me look much more girlish. "Very promising," my mother said. "Thank you, Andrew, I know this must be so hard for you! But I can tell already that your aunt will never suspect a thing. Now the fun begins," she said playfully as she took my hand and led me back to her bed. She sat me down and handed me the pantyhose which had freaked me out when I saw them. "These can be a little tricky, and they're kind of expensive, so please hike up your slip and listen very carefully." At that point, I finally snapped. "There is no fucking way I'm putting on pantyhose!" I shouted. "So like your sister," my mother chuckled. "I'll forgive that outburst because every woman in the world feels that way at one time or another. But they'll make your shoes fit much better, and your legs will look a lot nicer too. Now, stick out your left foot. That's right, now see how I've rolled one of them into a little doughnut shape? Here we go, up over your toes, up past your heel, nice and gently, that's good...now the other foot please, just like before, up we go, now stand up please," she said as she gently tugged them, one leg at a time, until they were up past my knees and almost to my panties. "Now, take the waistband in both hands and tug them up the rest of the way, that's right, try doing a deep knee-bend to get the last wrinkles out of them, perfect!" she said as she smoothed down my slip. "You really should have been a girl!" I was speechless as I looked down over the bulges in my bra and stared at my shimmering legs, peeking out from under the lacy hem of my slip, feeling a sensation of sheer delight like I'd never felt before. I was glad I had a slip on because my penis was starting to stiffen! What the fuck was happening to me?" "Are you ready to try on your dress?" my mother asked, as if I had a choice. I gave her a look that could kill, although standing there in a slip and stockings, it was impossible to put up much of a fight. "What do I have to do?" I asked nervously. She smiled at me. "You look like such a girl right now! No, please don't take that the wrong way, I know you're my son, but this would be so much harder if you didn't pass as a girl. When I'm through with you, nobody who sees you will have a clue." The dress my Aunt Esther sent me was white with some kind of floral pattern. I watched while my mother pulled down the zipper in the back and helped me step into it. "Careful, don't let your slip get caught when I zip you up," she cautioned me. After my arms went under the straps, I felt it tightening around me, and after she raised the zipper and fastened the clasp at the top, she lifted the skirt and smoothed down my slip before she lowered the hem back down. "Take a look at yourself, Amy," she said, using my sister's name to address me for the first time. I walked over to her full-length mirror and stopped in my tracks, frozen in shock. What I saw in the mirror wasn't me. It was my sister on Easter Sunday, one of the few times when she grudgingly wore a dress. My mother stood beside me and gently clasped a necklace behind my neck. "I know what you're thinking," she said. "You look so much like her. Good thing she refused to get her ears pierced," she continued sadly. "I miss her so much!" She turned away so as not to let me see her cry. "Goodness, look at the time!" she said. "Your aunt will be here soon and I have to get dressed myself. As you've learned, it isn't so easy for a woman," she smiled. "Before I do, let's try those heels on you." I sat down on the bed and gingerly slipped them onto my feet. When I stood up, the pain was instantaneous, and I would have toppled over if my mother hadn't caught me. "Oh dear, let's try that again. Take baby steps and try to keep your balance this time." I did, and I was able to make it halfway across the bedroom before I nearly fell down again. Suddenly everything hit me at once, and I curled up in a ball on the carpet, kicking off my high heels and shaking with sobs. "I hate this! I'm a guy, not a girl! Why did Dad and Amy have to go on that stupid cruise?" It had been almost six months since they disappeared, and I thought I'd cried myself out by now...." My mother got down on her knees and wept along with me, hugging me and stroking my hair until I finally stood back up. She disappeared and returned in a few moments with a pair of shoes in her hand, black and white flats from Amy's closet. "Try these, dear," she said softly. I stepped into them, and found myself able to walk around the room comfortably. "Please go downstairs and try to get used to your clothes before your aunt gets here. I'll be down as soon as I'm dressed. Oh, and take this with you - you'll need to get used to carrying one." She handed me a purse with the hairbrush and lip gloss inside it. Welcome to my world! It occurred to me sometime later that after all I'd been through, I was actually grateful to be wearing a comfortable pair of women's shoes. At least my crying jag extinguished the strange sensations I'd been feeling in my panties - for a while.... *** I paced around the living room, totally weirded out by my dress and nylons. They were so unlike anything I'd ever worn! No wonder Amy hated to wear them, I said to myself as I tried sitting down and getting back up without my dress flying every which way. At least my shoes were comfortable, I thought as I looked down at them while I tried crossing and uncrossing my legs the way I'd seen Mom and my teachers do it. I couldn't believe how dainty they made my feet look. That, and the electric sensation of my stockinged legs sliding against each other, started that strange, delightful feeling in my panties again.... I was startled by a knock on the door! I got up and peered out the window. A stretch limousine was parked in our driveway, and some guy in a uniform was standing at the front door. "Mom," I yelled up the stairs, "I think Aunt Esther might be here!" My mother appeared at the top of the stairs in her slip. In all my years I'd never seen her half undressed, but things were suddenly different now...."Let her in, I'll be down in a minute, and remember who you are!" When I stared back at her in confusion, she whispered, "Talk like a girl!" I tentatively opened the door. The chauffeur informed me that Madam Esther was waiting in the car. "Please tell her to come in," I said softly. "Of course, Miss." He returned to the limo, opened the back door and stuck his head in. A few moments later, my Aunt Esther gracefully emerged and walked serenely up the front walk. She was beautifully dressed in a longish skirt, with an elaborate scarf tied loosely around her neck, and still very attractive despite her gray hair. The driver took her hand and guided her as she slowly made her way. When she walked through the door, I stepped back nervously while she told her driver to wait in the car. "Amy, darling, come give me a hug." I hugged her awkwardly, then she stood back and raised her expensive designer glasses so she could study me more closely. "Such a pretty young girl," she smiled, "and that dress looks lovely on you!" "Thanks, it's nice," was all I could think of to say. She took my hand and sat down beside me on the sofa. "Mom will be down in a minute." "Ah, your mother. Before she joins us, let me tell you a few things that have to stay between us. Your father was my baby brother, in fact he was almost twenty years younger than me. A 'Saturday night surprise' I once overheard your grandmother tell someone. As you know, both of our parents went to early graves, and they left us each with a sizable inheritance. Perhaps it was because your father was so young, but he went through his money very quickly, God rest his soul. Fortunately, he met your mother, who was the best thing that ever happened to him. Anyway, I was very fortunate with my investments, and because I never married, I have more money now than I know what to do with. You are my only heir, child, and someday it will all be yours." I was stupefied, trying to think of something to say when Mom came down the stairs in her best dress. "Esther, it's so nice to see you," she said as they exchanged air kisses. "Your daughter is absolutely divine," my aunt said. "I thought you told me that she was still a tomboy? She's certainly turned into a beautiful young lady." I could feel myself blushing. "It's been a very difficult six months, and Amy has grown up a lot," my mother lied. There was another knock on the door, and my mother excused herself to answer it. I heard muffled voices, and when I craned my neck, I thought I could see a blue policeman's uniform! Sure enough, an officer poked his head into the room and looked Aunt Esther and me up and down while my mother spoke to him in hushed tones. Eventually he left, and when Mom returned, she had an ashen expression on her face. "Our reservation at Chez Panisse is at 7:00, so we'd better leave soon," she said. Aunt Esther insisted on taking us in her limo, and I almost forgot my purse before we piled into her stretch. It was the most luxurious vehicle I'd ever been in, and I forgot that I was wearing a dress and sat down awkwardly on the settee before my mother rescued me by tugging the hem down to my knees. Something was obviously bothering her, but she put on a brave face and made small talk with my aunt on the way to the restaurant. When we got there, the chauffeur opened the door for us and there was another awkward moment for me as I scrambled out of the limo in my dress, then we three "ladies" were escorted into the restaurant and shown by the hostess to a table laden with more china and crystal than I'd ever seen. Sensing my discomfort, my aunt assured me that nobody would notice if I used the wrong fork! Aunt Esther ordered Kir Royales for herself and Mom and a pink lady mocktail for me (ugh) before she made a startling proposition: "I know Amy's school lets out for the summer next week, and I was hoping I could persuade you to let her fly back to New York with me. It would be a wonderful opportunity for us to get to know one another better, and I'm sure she'd love all the things we could do in New York - the shows, the museums, the shopping...." I expected my mother to rule it out immediately. I was a boy, with my own life to live, and there was no way I was going to spend summer vacation living as a girl in New York with an old lady! As soon as Aunt Esther dropped us off after dinner, I was going to take off my stupid dress and all the other junk and reclaim my life. But Mom had a strange look on her face, and she told my aunt she'd have to think about it. I tried to kick her under the table with a dainty shoe. After we ordered our entrees, Aunt Esther excused herself to visit the ladies' room. As soon as she left, I tore into my mother. "Why didn't you tell her no?" My mother's voice was icy calm. "Andrew, did you steal a car last night?" "What? No way!" "Andrew, a cop came to the door tonight and he was looking for you, with a warrant for your arrest for grand theft auto!" "That's bullshit! Okay, so I was out with my friends last night, and we might have borrowed a car for a while, but I wasn't driving or anything...." "Oh Andrew, how could you be so stupid! Those 'friends' obviously fingered you to try to get off themselves. Do you know what's going to happen to you? With your record, they'll sentence you to a juvenile detention facility for a long time." "No way! We've got to hire a lawyer!" "With what? I can barely make ends meet as it is." "Maybe Aunt Esther will pay for one!" "Your aunt thinks you're a girl, remember?" "So you think I should go to New York until the heat's off?" "I don't know what to think anymore, Andrew. I'm so tired of all the trouble you keep getting into, and this time I'm afraid I can't help you, unless...." "Unless I agree to spend the summer living as a girl! No way!" "Your aunt's invitation may be the only way out." "Some invitation! With her I'd probably have to wear a dress every day!" "So like your sister. You might find a dress more comfortable than an orange jumpsuit. Uh-oh, here comes your aunt, let's drop it for now...." My aunt could obviously tell that we'd been having an argument. "Oh dear, I hope everything's all right?" she inquired. My mother squeezed my hand. "Just a little mother-daughter conversation," she sighed. "We've been having a lot more of them since she became a teenager." "I see. I certainly hope my invitation wasn't the cause. Of course Amy doesn't want to spend the summer with her maiden aunt," she smiled. "A pretty girl like you must have lots of boyfriends." "No way," I blurted out. "Well, you will dear, soon enough." The waiter appeared with our salads, and we ate in silence for a while. It was so surreal, sitting in a fancy restaurant in a dress, sipping my pink lady, watching my feminine fingertips curled around my salad fork...maybe New York wasn't such a bad idea after all? From what I'd heard about the juvenile detention facility from some of my friends, I'd be more likely to wind up with a "boyfriend" there than I would living as a girl in New York! "How soon could we leave?" I blurted out, shocking my mother. "For New York? I'm flying back the day after tomorrow. Are you sure you want to join me?" "I'm not sure she can," my mother broke in. "I'm not worried about her missing the last few days of school, but her wardrobe consists of jeans, sweatshirts, tee shirts and sneakers." "Nonsense! She can wear that dress on the plane - we'll be flying first class, of course. I'd like nothing more than to take my niece shopping in New York." I almost backed out at the sound of that, but when my mother agreed to let me go, my fate was sealed. *** The next day was a nightmare for me. As soon as my aunt dropped us off after dinner, my mother went into full panic mode. She started by rummaging through my sister's dresser drawers and closet until late into the night, but not before she helped me get undressed and take off my makeup. And she insisted that I wear some of my sister's old pajamas to bed, in case the cops came back! I slept in the next morning, a Sunday. When I finally woke up and went downstairs, my mother was sitting at the kitchen table, going over a long list in her hand. "Good morning, Amy," she said. "I'll fix us some breakfast in a minute, but first we have some things to discuss." "Maybe New York isn't such a good idea." "It's too late for that, Missy," she said without looking up from her list. "The first thing we have to do today is go to the CVS to pick up some female essentials for you: shampoo, conditioner, a hair dryer, mirror, brush, some scrunches in case you want to wear a ponytail, and of course some moisturizer and your own makeup - lip gloss, eye liner and shadow, mascara and a light foundation. I'll trim your eyebrows before you leave," she said, looking up at me, "and I guess we'd better get you a razor and some shaving cream for that peach fuzz on your face, and your legs of course...." I thought I was going to throw up. "I think I'd rather go to jail," I told her. "Next, we have to go to the outlets to try to find you some clothes. I looked at the label on that dress your aunt bought you, and it must have cost her a fortune! I don't feel right about her having to put together a whole wardrobe for you at New York prices. Your sister's bras and panties will be just fine, and I found a couple of skirts and dresses in her closet that might work, and some more shoes that might fit you, although I don't think she'd worn any of them in a long time. We'll go upstairs and try them on after breakfast." "This really sucks! Why can't I just be a tomboy like Amy." "Because you really are a boy, and if we don't try to make you look like a girl, you won't even get on the airplane with Amy's ID. Because it's Sunday, we won't be able to get you an appointment at my hair salon before you leave, but with a little more trimming I think I can make your hair pass inspection, and you'll have to be careful with those fingernails. I'll get you some more too," she said, adding them to her list. That's how my last day as a boy started. Maybe not physically, but mentally for sure, as she relentlessly reinforced every little feminine gesture, and stopped me every time I slipped into guy mode. After we finished our breakfast, she marched me upstairs and into her bathroom for another bubble bath. I didn't have to wash my hair or shave my legs this time, although she did have me run a razor over my face - there was next to nothing there - and she showed me how to moisturize my face and body all over before I put on another pair of Amy's panties and tried to learn how to fasten a bra, since once I got to New York I'd be on my own. I was too overwhelmed by all the changes to be frightened by the prospect - that would come later. At least there was no slip and pantyhose to contend with that morning! After my mother showed me how to put on a light coat of foundation makeup and had me practice a bit with an eyeliner, mascara and lip gloss, she taught me how to pull my hair high up into a ponytail at the back if my head - not down by my neck like I sometimes wore it as a guy - and made sure I knew how to fasten it with a scrunchie before we ventured into my sister's old bedroom. She had me try on a couple of her old skirts, one of which fit me okay, and a few of her dresses, which all cried out "church" to me. Her shorts and jeans fit all right, and I tried on a bunch of girly tee shirts which fit me too. But the find of the day was an old romper, which buttoned up like it was made for me, and I liked that it was like wearing shorts instead of a skirt. None of her shoes fit me very well, although my mother thought I might be able to squeeze my feet into some of them if I put on stockings, but her sandals fit me perfectly. This resulted in another trip to the bathroom where she made me sit still while she clipped, filed and painted my toenails a bright pink! By the time we were through with her fashion show, I was exhausted. She let me rest while she added some more items to her list. Stretched out on the sofa in a girlish romper, pink toenails peeking out from my sandals, playing with a strand of my ponytail, I must have dozed off. For the first time in my life, I dreamed that I was a girl. When I woke up, the strange sensation in my panties had turned into an embarrassing wet spot. *** My aunt, who was staying at a five-star hotel, offered to treat us to lunch, but my mother begged off, telling her that we had too much to do to get me organized for the trip. For once, she wasn't lying: after she woke me up (and I changed my panties) it was off to the drug store, where I watched as she methodically went down her list, adding a makeup bag and some sanitary napkins. I later learned that she had detected my little "accident" on the sofa and wanted to make sure I wouldn't be embarrassed if it happened again. Next, she pulled into a strip mall and asked me to wait in the car. I lost sight of her and couldn't see where she was headed. She was gone for about half an hour, returning with a shopping bag full of something. When I asked her what she got, she said, "It'll be a surprise tomorrow." Then it was off to the outlets, where we spent the afternoon trudging from one store to the next: two skirts, two tops, one sundress, two pairs of flats, and one light jacket later ("it rains in New York," she informed me) our last stop was at Claire's, where she selected several items of costume jewelry to finish off her list. "Most girls your age have their ears pierced. Your sister always refused to, and I'm sure you feel the same way, so I'm getting you some hoops with little spring clips that are very cute." "Whatever," I sighed. *** The rest of that day is a blur. We stopped at a fast food restaurant for dinner, but nobody looked at me funny or took me for anything but a teenaged girl. I actually caught a few guys staring at me, which creeped me out a little, but I would soon learn to get used to it. When we got home, Mom hauled one of her old suitcases out of the attic, and she spent hours sifting through my new things and Amy's old clothes, double-checking against another one of her lists to make sure I had everything a young woman would need in the big city. She even tossed in a summer nightgown, matching robe and slippers that she'd gotten Amy as a gift and had never been worn, and when I wasn't looking, she added the high heels that I'd rejected before she snapped it shut. We were up early the next morning to get me ready for my flight. First another bubble bath - I was beginning to enjoy them, even if it meant shaving my legs and washing and conditioning my hair. There are no bubble baths in jail, it occurred to me as I patted myself dry and wrapped a towel around my head in a turban after Mom taught me how. She also showed me how to wrap my bath towel around my chest, just above where my breasts would be if I had breasts. It was almost like she was making up for all the mother-daughter moments that she'd missed with Amy, who would sooner have slit her wrists than put up with all the girl stuff that I was being indoctrinated into. She watched me moisturize and put on my makeup, giving me little tips along the way. Then she pulled the towel off my head and handed me the dryer and brush. This took some more coaching, but soon my hair was styled to look reasonably feminine, and a few last snips with her scissors gave me some bangs. "All right Amy, now let me see you get dressed. Don't be embarrassed, it's very important that you know how to do this on your own before you go to New York." She watched as I pulled on a pair of panties under my towel, and looked on approvingly as I got my bra fastened behind my back. "Very good, it looks like you've been doing this all your life!" I was fumbling around for some knee highs to stuff into it when she handed me a box filled with two pert silicone breast forms. "This is the little present I bought for you yesterday," she said as she showed me how to tuck them into my bra cups. They were flesh colored, teardrop shaped and each had a realistic-looking nipple. Sized for a petite woman, they looked and felt like the real thing. "While we're at it, I suggest you tuck this into the front of your panties - there are plenty more in your suitcase. Girls wear them when they're having their periods," she explained, "but boys have been known to have emissions too...." Enough said! I put on my pantyhose before I put on my slip this time, and once again they triggered that strange, delightful sensation in my panties. I was glad Mom gave me that pad! Stepping into my slip and feeling it slide up my silky legs gave me another rush, which I tried to ignore as I stepped into my dress. It was very awkward trying to get the zipper started, but eventually after hiking up my dress a bit I got the hang of it, and bit by bit I was able to get the zipper all the way up. I even found the clasp and was able to get it fastened too. "Very good, you get a star," my mother beamed. "Now lift up your dress and make sure your slip isn't all tangled." Sure enough, it was, and she showed me how to straighten everything out. After I stepped into my flats, she handed me a necklace and watched while I figured out how to get it clasped behind my back. "Another star, you were born to do this," she teased me. "Mom, I know you're trying to cheer me up, but that really isn't helping." "What's the matter, dear? Are you scared?" "Terrified!" "I'm sorry, and I'm sorry you've gotten yourself into this predicament. I know all of this must feel incredibly strange for you, but just try to imagine what it would be like to be locked up?" "That's the only thing that's keeping me going." "Come here and get a good look at yourself." She stood me in front of her full-length mirror, and once again I had almost an out of body experience, as if I were staring at my older sister, only looking better than she ever did. "Sweetheart, I'm not saying this to tease you or make light of the situation, but you have to admit that you make a very pretty girl. I know this is only for a little while, so why not try to make it an adventure? Someday you'll look back on all this and wonder how you were ever able to pull it off. But you can pull it off, if you keep a positive attitude, so please try, okay?" "I'll try, Mom. And one thing's for sure. I'll never go for a joyride in a hot car again!" She hugged me, and I hugged her back, for a long time. Then she gathered up my makeup, hair dryer and brush and stuffed them all in an outside pocket of my suitcase. "One more thing," she told me. "There's a casual purse for everyday in your suitcase. You'll need to take the purse you carried last night on the plane. Now this is very important! I know you're not used to carrying a purse, but in addition to a brush and lip gloss I've put a girl's wallet in there with some mad money in case you want to buy something at the airport, and your sister's learner's permit, which you'll need for identification to get on the plane. Go ahead, take it out so you'll know where to find it when you get to the airport." I opened my purse and fished out Amy's identification. She looked like a ragamuffin in her picture, but my mother told me not to worry. "TSA will just think you've blossomed." "Where's my cellphone?" "I think that would be a mistake. The police might be monitoring it. And no social media! Remember, you're no longer Andrew." "You're telling me," I sighed after another long look in the mirror. "Check out the outside pocket of your purse." I did, and found a fully charged cellphone. "That's Amy's old phone. Your father wouldn't let her take it on the cruise so she wouldn't be texting her friends all the time. All of her friends have long since stopped trying to reach her on it, but the number's still good, so we can keep in touch that way, but only if absolutely necessary." Just then the doorbell rang, and my mother peered out the window to make sure it wasn't the police. "Your aunt's limo is here," she announced. I helped her lug my suitcase down the stairs, and when she opened the door the driver took it the rest of the way. Mom accompanied me down the front walk and watched as I climbed into the car. There were tears in her eyes as she said goodbye to Aunt Esther, hugged me one last time, and watched us drive away. As we pulled out of the driveway, I saw a police car down the street, with an officer inside, watching the house. A stakeout! Fortunately, a teenaged girl getting into a limousine was the last thing they were looking for.... My Aunt was wearing a dress that looked very expensive, even to my untrained eye. I tried to think of something to say, but she beat me to it. "You look so lovely in that dress," she complemented me as we rode to the airport. "I was a little afraid you'd show up dressed like a boy. Jeans and sweatshirts, that's all you had on the last time I saw you." Talk about weird! "Uh, you look nice in your dress too," I stammered, "and thanks again for buying my dress. My Mom says it must have cost you a fortune." She threw back her head and laughed. "I love your mother, such a character. What I find fascinating is how you went from being a tomboy to a delightful young woman. I'm sure your mother had something to do with it?" Lady, you don't know the half of it, I said to myself. "Mom and I have gotten a lot closer since Dad and Amy...I mean Andrew disappeared," I said, almost blowing my cover before we even got on the plane! My aunt seemed not to notice my slip up. "What time do we get to New York?" I asked to change the subject. "Around six o'clock. It should take us another hour to get to my apartment. Have you ever been to New York?" "No, what's it like?" She threw back her head and laughed again. "So precious, the innocence of youth....I'll tell you all about it on the plane." When we got to the airport, the driver handled our suitcases while Aunt Esther led me to the first class ticket counter, bypassing a long line of hassled passengers. I stood there quietly until I was asked to produce my identification. The moment of truth! But the woman at the counter just glanced at it, and my aunt handed me my boarding pass which had Amy's name on it. So far, so good! "We're TSA Pre," she told me as we headed for security. "What does that mean?" "It means we can skip the long lines and we won't have to take our shoes off." I just followed her, and after I showed Amy's ID again to the TSA officer, who stared right at me after glancing at Amy's photo, all I had to do was put my purse on a conveyor belt and follow my aunt through a metal detector. I was so glad I didn't have to walk through with only pantyhose on my feet! After we collected our things, we walked quickly to our gate, where the first class passengers were already boarding. We were in seats 1A and 1B. I had to put my purse in the overhead compartment before I could stretch out in my enormous aisle seat. My aunt, who had the window, kicked off her heels, so I did the same with my flats and tucked my legs up under my dress. "This is amazing," I said. The only other times I've flown it's been coach or Southwest." "First class is a far cry from the old days, but it's still the only way to travel." A flight attendant asked us if we wanted something to drink, and I was shocked when my aunt asked for champagne for both of us! "She's twenty-one," my aunt winked at her. Other than a few sips of beer with the guys, I'd never really drank alcohol, and my first glass of champagne on an empty stomach gave me a little buzz. After we took off, my aunt showed me how to raise the footrest, and it felt so weird to see pink painted toes through my pantyhose when I stretched out my legs. Aunt Esther ordered mimosas, and I was starting to feel pretty loose as we climbed through the skies. "You asked me about New York," my aunt said. "New York is a giant madhouse, crawling with refugees from every part of the world, everyone on the make." "And you like living there?" I found it hard to believe that an old woman would enjoy a place like that. "You didn't let me finish! The Upper East Side of Manhattan, where I've lived for almost forty years now, has been and always will be an enclave for the rich and famous. My apartment is on Fifth Avenue, overlooking Central Park. I can walk or take a taxi to the theater district, all the best stores, world famous museums and galleries, or just stay in my apartment if the weather is unpleasant and watch the world race by. Downtown Manhattan has Wall Street, and uptown is Harlem, but midtown Manhattan is the center of the universe, and I couldn't possibly leave it. I came there as a young woman, got into modeling, and even made a few magazine covers and TV commercials when I was in my prime. Then your grandparents' health deteriorated, and I helped them both in their final days before they passed away. My inheritance made me a wealthy woman, so I returned to New York, bought my apartment and gradually turned into a lady of leisure - the modeling jobs dried up after my looks started to go," she added. "Young women today have it so much better, you can do anything!" "Wow, that's so amazing. You were really a model?" "Yes, and to be quite honest, I think you have all the makings. You're pretty, thin, and tall enough to get a first look. I still have friends at my old agency if you'd like to give it a try. They're always looking for fresh new faces." I was sure she was kidding. *** I had one more glass of champagne with breakfast, a delicious omelette, and by then I was feeling no pain. Aunt Esther pulled down the window shade and closed her eyes, and soon I drifted off into a deep sleep. I can remember two vivid dreams. The first was a nightmare: I was in jail, surrounded by a gang of much older guys, who kept teasing me and pushing me around, bragging about which one of them would be the first to give it to me up the ass. I woke up with a start, and was relieved to find myself in my first class sleeper seat, even if I was wearing a dress! The second dream was more profound: once again I dreamed that I was a girl. I was wearing a tennis dress this time, very short and sexy, and one of the guys from my prison dream was in it too, only now he was wearing white shorts and a white polo shirt. He was running me all over the court until I gave up, and when we met at the net, he kissed me! I woke up again, to the wicked delight of my penis pulsing in my panties, soaking my pad. I must have moaned or groaned out loud, because when I looked up, I could see Aunt Esther staring at me with a strange expression on her face. "Must have been quite a dream," she said. "Yeah. I have to go to the bathroom." There was a lavatory exclusively for first class passengers at the front of the plane, and after I fumbled around getting my shoes on, I grabbed my purse out of the overhead and I locked myself in. My hair was a mess and my lip gloss was gone! After I lifted up my dress and slip and pulled down my hose and panties, I tossed my pad into the trash, wiped myself off as best I could with a wet paper towel, and relieved myself standing up. I was about to pull myself back together when I spied a little drawer under the vanity with "Sanitary Napkins" written on it. Sure enough, it was a supply of fresh pads for female passengers, and I stuffed one into my panties. After my dress was back in place, I ran my brush through my hair and applied a coat of lip gloss. There was a spray bottle of women's cologne above the sink, and I lifted my dress back up and zapped myself to try to conceal the musky scent of my spent semen. Aunt Esther was waiting for me. "Everything all right? You were gone a long time!" "I'm fine," I answered nervously, worried that she'd seen through me somehow. Had I blown everything already? "I've been thinking about your modeling potential. Every major designer is looking for an edge, something that differentiates them from the pack, models with that something extra special. I think you might just have it." "Me?" My aunt must be going senile! Couldn't she tell I was really a guy? I felt relieved that she hadn't seen through my disguise. "Something to think about," she said before she closed her eyes and dozed off again. *** The next morning, I woke up with my first hangover, uncertain at first as to who or where I was. The straps of the nightgown around my shoulders reminded me that I was Amy, and the luxurious four-poster bed, and the horns honking outside my window, reminded me that I was in the guest room of Aunt Esther's Fifth Avenue apartment. Last night came back to me slowly...the limo from the airport to Manhattan - my eyes must have been as big as saucers, taking in all the skyscrapers - followed by a mind-boggling tour of Aunt Esther's luxurious apartment. After she fixed us a light supper, I was totally exhausted from my day of traveling cross-country as a girl, but after my aunt showed me the guest bedroom, she suggested that I hang up all the skirts and dresses from my suitcase, and put my lingerie away in dresser drawers, before I collapsed into bed. My nightgown might have told me that I was Amy, but the raging hard-on in my panties reminded me that I was all boy! How was I ever going to get through another day in girl's clothes like this? I tugged my panties down to my knees, rolled over on my side, and began stroking myself with the satin folds of my nightgown. The feeling was exquisite, indescribable, and it didn't take me long to erupt onto the sheets of my bed. When I finally came down to earth, I tucked my softening penis back into my panties, and put on the robe and slippers which matched my nightgown. They were all in a pretty shade of pink that my sister wouldn't be caught dead in. After I tied my hair into a loose ponytail and brushed my teeth, I found Aunt Esther in the kitchen, sipping coffee and reading the New York Times. "Good morning sleepyhead," she smiled. "Good morning, what time is it?" "Almost ten o'clock! But that's only seven o'clock your time, so I knew you'd be sleeping in this morning. You'll be on New York time before you know it. What a pretty robe and nightgown!" "Oh, thanks, Mom got them for me." I sat down and had a glass of orange juice while Aunt Esther scrambled some eggs and put some bread in the toaster. "Shall I tell you what I have planned for today?" "Sure," I yawned. "After you get yourself dressed, I thought we might start with a quick visit to the Museum of Modern Art, just to give you a feel for it. Then we can walk through Central Park to Rockefeller Center and have lunch, before we do a little shopping." "My mom bought me some clothes yesterday." "I'm sure they'll be just fine, would you like me to help you pick out an outfit to wear today, something appropriate?" I nodded my head yes. "Anyway, after we hit the stores, we can have dinner at a wonderful pizza place near the theater district, and if you're not too tired I got us tickets to see Jersey Boys. How does all that sound?" I was overwhelmed. "It all sounds so cool!" I said. "You're the best aunt ever." I had never been spoiled like that in my life, and I felt a twinge of jealousy towards my sister, even though I'd taken her place. This was all just a fantasy, but it was real too, and I knew that I was starting to enjoy it. "I know the past few months have been difficult for you," my aunt weighed her words, as if she had something on her mind. "Let's enjoy the day and live for the moment, you have a big city to explore!" So after breakfast, my aunt followed me upstairs, and when she saw my unmade bed, she gently told me that it would be very nice if I could make it starting tomorrow. I started to apologize but she told me not to worry about it, and I helped her as she pulled up the sheets, fluffed the pillows and smoothed on a duvet. Then it was into my closet, where she suggested that I wear the sundress, since the temperature was supposed to rise into the high eighties. "Do I have to wear a slip and pantyhose again?" I asked her. "Goodness no, your dress is fully lined and your legs will roast if you wear stockings! Those white flats will be perfect with your dress." I was so glad! Fortunately, my bedroom had its own bathroom with an old-fashioned tub, and after she left, it was up to me to make me a girl again. My aunt had some amazing French bath crystals which made the water feel sooooo good! After a long soak, I shaved my legs and washed and conditioned my hair, then I moisturized my skin all over before I put on my makeup, unassisted for the first time. Not bad! Then I dried my hair, which I decided to wear in a ponytail today since I had a scrunchie which matched my dress. So far, so good...I popped a pad into the front of my panties and it took me several tries to get my bra fastened and my breast forms just right. Then all that was left was my dress! I slipped it on and pulled up the zipper like a pro. I stepped into my cute flats, selected a simple necklace that I thought looked all right with my dress, and even managed to clip on a pair of earrings. Almost done! After I put my wallet, cellphone, lip gloss, hairbrush and an extra sanitary pad in my "everyday" purse, I took a look at myself in the full-length mirror on the back of the closet door. Once again, I had that strange sensation of looking at somebody else, not my sister this time, just a very pretty girl who happened to be me. I could feel something beginning to stir in my panties, so I quickly turned away and walked into the living room, where my aunt was waiting for me. "You look lovely, dear!" "You too! I really like your skirt," I said lamely. She was dressed with casual elegance in a white pleated skirt that came down well past her knees, a colorful blouse, and low-heeled shoes, no stockings. I found myself becoming much more attuned to what she was wearing, and how she carried herself, the more time I spent with her as a girl. "I'll be ready in a few minutes," she said. I sat down on a big chair and played with my dress, which had a very full skirt. On a whim I opened my purse and switched on Amy's old cell phone. To my surprise, I had a text from Mom. Is everything ok? Yep. Got myself dressed solo today. Wonderful! What did you put on? My sundress. We're off to some museum. Have a wonderful time Did you know Aunt E used to be a model? Oh yes. Ask her about JFK Jr Who's JFK Jr? Google him! Gotta go I switched off my phone when Aunt Esther returned, and we were off to conquer the Big Apple. *** My first day in New York was the most wonderful day of my life, even if I had to spend it as a girl! It started with a leisurely walk down Fifth Avenue on a bright sunny morning. The people on the street were all in a hurry. It was already quite warm, and for the first time I appreciated how comfortable I could be in women's clothes, wearing only a bra, panties and a sundress, while the guys in their suits, ties and wingtips sweated on the sidewalk as they passed me by. The feeling of my sundress swishing around my bare legs was incredible! When we got to the Museum of Modern Art, I was totally blown away. I don't think I ever spent much time in museums as a boy, but this place knocked me out! So many wild paintings and sculptures, all by artists I've never heard of. Some of the exhibits were totally off the wall! My aunt seemed to know everything about anything, and she pointed out interesting things about this and that, but we only scratched the surface. When she finally tore me away, we crossed Fifth Avenue and went for a stroll through Central Park, and I was blown away once again. That park is huge! Acres and acres of beautifully landscaped gardens, all kinds of trees and giant boulders, I think we even walked past a zoo before we came out in front of a huge hotel, I think she said it was The Plaza, and she pointed out Trump Tower as we made our way to Rockefeller Center. There was a restaurant overlooking the ice rink, although all the ice was gone and there were flowers everywhere, and we had a fun lunch while we got to know each other better. She went to the ladies' room after we sat down, and I pulled out Amy's old phone and googled JFK Jr. I felt like such a dunce, not knowing that he was the only son of President Kennedy, anyway his pictures were amazing, what a stud! When my aunt got back, I said, "My mom told me to ask you about JFK Jr." "Oh she did, did she? Well, I guess that means you're old enough...I dated him for a while." "Really! Did the secret service have to come along?" She threw back her head and laughed her familiar laugh. "Good Lord no, he was the most eligible bachelor in New York, and that would've cramped his style." "So where did you guys go?" "Mostly his apartment, since I was sharing mine with two other girls. I lived down in Chelsea then, that's a little south of here, still in Manhattan." "Oh. Was that when you were a model?" "Um hmm." "So what was he like?" She closed her eyes and smiled. "He was handsome, athletic, and tons of fun." "So did you like make it with him in his apartment?" "Good girls never kiss and tell. Smart bad girls too," she added slyly. "Oh wow. You got laid by JFK Jr." "Well, that clinches it," she said. "What do you mean?" "Oh nothing, we'll discuss it later. I'm looking at your fingernails, and I think one of them came off." "Yeah, these are press-on jobs Mom gave me when she made me dress up...I mean when we knew you were coming." "I understand. Our next stop is to my nail salon." *** An hour later, my hands and feet had been recreated. Gone were the cheap press-on fingernails, replaced by long, glistening talons in a soft coral which my Aunt assured me would stay on and last a long time. As for my toenails, the coat of quick dry polish my mother had given them was replaced by hot pink! It was almost a shame to put my flats on after that, and Aunt Esther must have read my mind, because our next stop was to an exclusive shoe store on Madison Avenue, where she insisted on buying me a pair of open-toed white sandals with a little heel on them. I was worried that maybe I wouldn't be able to walk in them, but after trying them on in the store and walking around a little, I could tell that I'd be all right, and they made my feet look so feminine! The next stop was Sax Fifth Avenue, where my aunt made me try on a little white sweater that just covered my shoulders. "You may need it in the restaurant or the theater tonight, sometimes the air conditioning can get very cold," she explained. "Now, I'm going to treat you to something a little bit extravagant, but we are still celebrating your sixteenth birthday, aren't we?" Before I could think of a reason why not, she led me into a jewelry store called Cartier where she asked a saleslady to show us their "less expensive" wristwatches. I started to protest, but she cut me off. "A young woman needs a reliable watch," she insisted, "and giving you one for your birthday will give me great pleasure, so let's not have an argument." When I tried one on my wrist, I didn't need any more convincing, it was so elegant! "Now, we have a big decision to make," she said before we checked out. "Most girls your age have their ears pierced. You're sixteen now, and you need to start wearing cute earrings. What do you say?" I don't know why I didn't say no on the spot! Up until that moment, everything she and Mom had done to me was completely reversible. This would be like crossing some kind of line, from which there might be no turning back. I don't know why, maybe I was just overwhelmed and excited, but I told her yes. Two sharp stings later, I had passed the point of no return. *** What can I say about dinner and the Broadway musical? The pizza place my aunt took us too was unlike anyplace I'd ever been - it had stained glass windows (I think it used to be a church or something) and the pizza was out of this world. Then it was off to see Jersey Boys, which was a total first for me, like so many other things I'd experienced in the past three days, had it only been that long since I started living as Amy? Anyway, the show was awesome, some really funny guys singing some old songs I'd never heard before, but the whole theater was rocking and I totally got into it. Oh what a night! When the show was over, we caught a taxi back to my aunt's apartment, and as soon as I'd taken off my dress, creamed off my makeup, swabbed my earlobes and put on my nightgown, I fell fast asleep. *** The next morning, when I made my bed, I saw the remnants of the wet spot I'd created when I jerked off in my nightgown the day before. Aunt Esther couldn't help but notice it when she helped me make up the bed yesterday! A little worried about that, I stuck my head into the kitchen after I'd put on my robe and slippers. "Good morning, Andrew," my aunt said without looking up from her paper. "Good morning," I said back to her, and it took me a few moments to realize what had just happened. When it finally sank in, I started to shake all over, then I broke down and cried. "I'm sorry, I'm so sorry," I blurted out. "This wasn't my idea! Mom thought you'd wish Amy was alive instead of me, then when the cops started looking for me, I had to keep up the disguise...I'm sorry, I'm so, so sorry," I wailed. She took me in her arms and hugged me, patting me on the back and rubbing my shoulders as I cried and cried. "It's all right, dear, everything's going to be all right. Can I still call you Amy?" "Y-yes," I sniffed. Why wasn't she mad at me? I was sure I'd be on the next plane out of New York, and Mom and I would be homeless. "You can call me Amy. Please call me Amy," I sobbed. "Sit down and tell me all about it," she said. "I think I've already figured out most of it, but what was that about the cops?" In between sobs, I poured it all out for her. When I was done, she shook her head sadly. "You poor thing...I'm not very happy with your mother, but I guess her intentions were good. As for you, young lady, no more criminal mischief while you're in New York! The NYPD isn't as dense as your local authorities." That made me smile in spite of myself, then my aunt giggled and shook her head, and I cried some more until my tears ran dry. "When do I have to fly home?" "Do you want to go home, Amy?" "No, no I don't...I want to stay here with you, for a while...." "Then let's pretend that nothing's happened. I still think of you as Amy, and if you don't mind my spoiling you a little, I can make you a bit more convincing as a girl." "What gave me away?" "Nothing gave you away! Sweetheart, you are drop dead passable as a girl. It was only when we started to spend time together that I picked up little hints, clues that I really didn't put together till yesterday, but it had nothing to do with the way you look, or talk, or your mannerisms....let me make us some breakfast and we'll talk about it some more." My aunt made delicious blueberry pancakes, with real maple syrup, and I tried coffee for the first time in my life. "How long have you wanted to be a girl?" she asked me after we sat down to eat. "That's what's so weird about all this! I never wanted to become a girl, not ever. When Mom told me I had to dress up and pretend to be Amy because you were coming, we had a big fight." "Your sister was never very feminine. Did she ever say she wished she was a boy?" "All the time! It used to drive my mom crazy, but Dad kind of treated her like a boy, taking her fishing and encouraging her to play sports." "Did your father do things like that with you too?" "Maybe not so much. I'm not nearly as athletic as my sister was, and I spent a lot of time alone, playing video games and stuff. But I never wanted to be a girl." "And how do you feel right now? Do you like being Amy for a change?" I didn't hesitate. "I love it. Not at first, I hated my mother when she forced me to put on that dress you got for Amy, but little by little I guess I got used to it, and yesterday, spending the whole day with you as a girl, was the best day of my life. I guess my sister always got all the attention, but all those nice things you did for me made me feel sorta special, and now I'm not so sure I want to go back." "Go back home?" "No, go back to being a guy. I guess I'm pretty screwed up, huh?" "I don't think so, Amy. You're just exploring your limits. I'm no psychiatrist, but from what I've read and seen on TV, there are a lot of young people like you. I suspect that your sister was just the same, although it's much easier for girls to be tomboys, our society has always kind of accepted it, and most girls grow out of it. I'm sure that's what your mother expected Amy to do. But for boys, I think it's a lot different." "No kidding. My friends at school would beat the crap out of me if they could see me right now." "Well, they're not going to get the chance. And I don't even think I'll tell your mother about my little discovery, at least not for a while. What do you say if we just keep pretending that you're Amy?" "Are you sure that's okay?" "That's what your mother wanted, isn't it?" "I guess you're right." "Well, now that that's settled, let's get dressed and figure out what we're going to do today. Remember to tuck a shower cap over your ears when you take your bath, and don't wash your hair today. Have you been following the instructions about taking care of your ears till the holes are healed?" "Yep, and they don't even hurt much." "Attagirl!" *** And so began my summer as a girl in New York City. I think we went to every museum in Manhattan - well, that's an exaggeration, but there were lots of them, and I even got to channel my inner boy at the Museum of Natural History, those dinosaur fossils are unbelievable! I got to channel my inner boy at Yankee Stadium too, after Aunt Esther bought me some shorts and a girly tee shirt and sneakers. We had amazing seats behind third base, and the game was epic! But most of my time was spent in skirts and dresses, and my inner girl was happier with all the musicals and plays we went to. My aunt read the New York Times every morning, and I got hooked on it too. There was so much to learn about the world! For the first time in my life, my horizons were expanding. One day I came across an article in the Health and Science section that was to have a profound effect on me - more about that later.... We also watched the Today show during breakfast, and one day I remarked that the girl doing the weather had really cute hair. "That's a bob, dear, they're very easy to take care of, and I think you'd look adorable with your hair that way. Why don't you try it? It would certainly look better than that mop of yours." I stuck out my tongue at her as she picked up the phone to make an appointment for me at her salon, and later that morning I was sitting in a chair being worked over by a sharp young woman who suggested that a little tint might bring out the color of my hair. Two hours later, I was a head-turning blonde! On the way back to the apartment, my aunt suggested that we do something about my makeup too, and by the end of the day I was a sophisticated city girl, with a new supply of expensive makeup to replace the stuff my mom bought for me at the drugstore. It wasn't all fun and games: we spent a very somber afternoon at the 911 memorial and museum, and my aunt arranged for a service in remembrance of my father and my sister at St. Patrick's Cathedral. I was overwhelmed by how beautiful the church was, and the service made us both cry. I wore a black dress that my aunt bought for me with black stockings and the high heels that my mother slipped into my suitcase. I can't say that they were very comfortable, but I got around on them okay, and after seeing me walk in them my aunt told me again that I could be a model! But the highlight of the summer happened out on Long Island. One day my aunt told me that we'd been invited to spend the weekend at one of her friend's houses in the Hamptons. When I told her I didn't know where that was, she laughed and told me it was where the rich people went to the beach. Her friend was one of them, and she had a big house with a swimming pool and tennis court. Her son, who had just been accepted at Yale, would be there, although my aunt confided that everyone knew he was gay, so he wouldn't pose a threat to me. So after another shopping excursion for a girl's swimsuit, which had to strategically cover me in all the right places, and a cute little tennis dress, we were off to the Hamptons in another limousine. We got there late Friday afternoon - the traffic getting out of the city was awful - in time for a casual dinner on their deck overlooking the Atlantic. The soon-to-be Yale man's name was Robert, and he was very good-looking. We sat next to each other during dinner and we kind of hit it off. The next morning, he asked me to play tennis with him, and after I told him I wasn't very good, he played with me anyway, and we had a fun time swatting the ball back and forth. Playing tennis in my skimpy little dress was like running around in lingerie and sneakers! It reminded me a little of that dream I had on the plane, and I started to get that feeling in my panties once again.... Fortunately, Aunt Esther got me a gaffe at a ballet store before we left Manhattan, and my boy parts were safely tucked away under my swimsuit when I dove into the pool after our tennis game. Robert and I splashed around together, and he had fun dunking me until I dunked him back! I looked over at Aunt Esther a few times, but she was totally preoccupied with her girlfriends. I put on a simple white sundress for dinner, and Robert and I sat next to each other again. Our hostess was already tipsy from cocktail hour, and she poured us each a glass of wine! Mine went straight to my head, and I could tell that Robert had a buzz on too when he snuck us each another glass when nobody was looking. He asked me if I'd like to go for a walk on the beach after dinner. He started talking about what life was going to be like at Yale, and I just listened and said as little about me as possible. I blame the wine for what happened next. "I don't know why I'm so attracted to you," he said. "I've always known I was gay. Maybe I'm really bi?" "No, you're definitely not bi, Robert." I took his hand. "Not even close." "How can you say that?" "Because I'm really a boy." "You're what?" "It's true. See for yourself if you don't believe me." I spun on my bare feet in the sand and lifted up my dress. He reached under it, and felt my stiffening penis inside my panties. Then he kissed me, like I'd never been kissed before. I wrapped my arms around his shoulders and kissed him back. This was way better than my dream on the plane! He took my hand and led me into the dunes, where he lay down beside me, pulled down my panties, and started to suckle me under my dress. It was sheer heaven! I ran my fingers through his hair as I came closer and closer, until I couldn't hold out any longer, and I came with a rush into his mouth. Every synapse in my body was on fire as I came and came and came, and he gobbled me up like there was no tomorrow. When I had nothing more to give, he eased himself up and looked into my eyes. "You taste delicious." "Anytime, buddy boy." "Why are you pretending to be a girl?" "It's a long story." "We have all night." He kissed me, while I began to stroke his stiffening penis. I gave him a sanitized version, careful not to tell him I was only 14. "Wow," he said. "I thought I was hot shit getting into an Ivy League college, but my life's been dullsville compared to yours. I've never made it with a jailbird," he teased me. "I'll have to go back and face the music sooner or later, I guess." "Are you a virgin?" "I am." "Don't worry, I'll be gentle." He rolled me over onto my tummy, pulled my panties the rest of the way off, and started to probe me with his rock-hard penis. I gasped when I felt the pain of entry, which was soon replaced by an incredible feeling of raw, carnal pleasure as he filled me up and began to thrust, back and forth, in and out, as if our bodies were made to be played with this way, and he kept pumping faster and faster until he cried out and I could feel his hot jism deep inside me, making a woman out of me. It didn't feel wrong, it felt so good! We lay there panting, lost in our separate thoughts. "Please don't tell anyone that I'm not a girl," I said. "Are you kidding? Right now, my mother is thrilled, thinking that I'm making it with a chick. Your secret is safe with me, baby." We crept back into the house, where the adults had already gone to bed. It took me a long time to fall asleep, after he kissed me goodnight and we slipped into our separate bedrooms. The next morning, after Aunt Esther and I packed up and got ready to leave, Robert asked me for my email address and cellphone number. I gave him Amy's. During the long drive back to New York, Aunt Esther finally got around to asking me about my disappearance the previous night. "Good girls don't kiss and tell. Smart bad girls either," I reminded her. She laughed all the way back to Manhattan. *** Summer was winding down, and I began to worry about what I was going to do with myself when it was time to go back to school. The cops were still looking for me, and I knew that if I turned up at my school as a girl, I'd get my ass kicked for sure. I had to be honest with myself. I wasn't sure that I ever wanted to go back to being geeky Andrew, after my summer in Manhattan as a pretty girl.... Fate intervened in a totally unexpected way: I was having breakfast with Aunt Esther one morning in late August when my cellphone buzzed with a text from Mom. I rarely heard from her, to avoid giving the cops a trail, so I thought it might be important. Her text gave me the shock of my life. "Holy shit!" I shouted. "What is it, dear?" Aunt Esther asked me. I handed her my cellphone opened to the message: Your father and sister are alive *** "Are you sure you don't want to come with me?" I asked Aunt Esther for the hundredth time. "No dear, the last thing your family needs right now is me in the way. You've got to put your lives back together first. Don't worry, I'll come see you soon." "Does Mom know when I'll get there?" "Yes, and she's going to meet your plane. When I spoke to her this morning, she was a nervous wreck, but I made sure she got your flight information. Your father and sister will be in the hospital for several more days, she told me." "Does she know I'm coming back as a girl?" "Yes, of course, that's the only photo ID you have. I'm sure she's expecting you to change back into Andrew once you get home." "I wish you were coming to help me explain!" "Sweetie, this is a decision only you can make. I'm sure now it's the right decision for you, but it's been your decision, and you're going to have to own it." "I know, it's just going to be hard, with my Dad and Amy especially. But I'm just so happy they're alive!" The shocking news of my father and sister being discovered alive on a desert island made the front page of the New York Times. Somehow, they had managed to swim to an overturned lifeboat, and drifted for days without food or water until they washed ashore on a remote atoll in the middle of the Pacific. There, they had survived by their wits, eating fruit and coconuts, and fish they were able to catch with their bare hands. They were severely malnourished, and badly sunburned, but otherwise in remarkably good condition. I packed my suitcase with most of the clothes I'd brought from home, and a few of the outfits Aunt Esther got me in New York. The rest of my new things would be waiting for me when I came back, which I hoped would be soon. For my flight, I decided to wear the same dress I wore on my flight to New York, with pantyhose and the high heels that I now felt at home in. My limo to the airport was waiting for me on Fifth Avenue, so after a long hug and a kiss goodbye, I was off to catch my flight. *** I was a supremely confident young woman now as I made my way through check-in and security, but first class wasn't the same without Aunt Esther! Although I looked much older with my new hairdo and more sophisticated makeup, there was no way the flight attendant was going to offer me a glass of champagne, and the creepy businessman sitting next to me kept staring at my legs...I closed my eyes and thought back to my crazy romp in the dunes with Robert, and wondered if I'd ever see him again? I had a lot of time to think about other things, too. For starters, how to tell my parents that I wanted to be a girl full-time, and start taking female hormones before it was too late? My puberty had already started, and it wouldn't be long before my body started to change more and more. What's more, I had fallen head over heels in love with New York, and Aunt Esther told me several times that she'd love to have a full-time houseguest as she got older. She could open doors for me that my parents never could, and after I heard it from her enough times, I was beginning to believe that I really could make it as a model. "Transgender is all the rage now Amy, and with your bone structure and waifish figure, the designers would be falling all over themselves to get you into their dresses." She had confirmed this with her old agency, without revealing to them that her potential prot?g?e was her nephew/niece, and if I weren't racing home, I'd probably be in front of a camera right now. There was even a private high school for young models, which my aunt was sure would accept me, since she was on the board of trustees! But most of all, my thoughts came back to my family. How had Dad and Amy ever survived that long on a remote island, totally cut off from civilization? While they were subsisting on nuts and berries, I'd been living a life of total luxury, and I knew that I could never have made it if the roles had been reversed. My father was smart and he knew how to take care of himself, but my sister? She'd been a tomboy before she went overboard, but she was still just a teenaged girl, and she'd been fighting for survival for months on end, without any hope of rescue. How had that changed her? I was about to find out. *** My mother didn't recognize me at first when I waved to her at the baggage carousel. "Oh my God, is that really you? If you hadn't been wearing that dress, I never would have known...everything about you is so different! And how did you get so tall." "It's my heels, Mom," I said as we hugged each other. "You packed them for me, remember?" She stood back and studied me intently from head to toe. "I just can't believe it! I was a little worried that your aunt might see right through you, but how could she?" I decided to wait till later to tell her. My suitcase came down the ramp, and Mom insisted on pulling it. "When can I see Dad and Amy?" "We can see them later today in the hospital, after we go home so you can change." "Are the cops still looking for me?" "Oh, I forgot to tell you in all the excitement, your hooligan friends all pleaded guilty the other day, and the DA has dropped all the charges against you!" What a load off my mind! "That's so great! Let's go straight to the hospital." She stopped pulling my suitcase and stared at me. "You can't be serious." "Why not?" She looked at me like I'd lost my mind. "Because you're dressed as a girl, that's why! We can't let your father and sister see you like this! They have no idea that we told your aunt that it was really her nephew who was lost at sea, or that the police have been searching for you. There was no way I was going to tell them after all they've been through. As far as they know, you've been away for a few days visiting your aunt in New York, not spending the summer turning yourself into a...into a...." "Go on and say it, Mom. This was all your idea, remember? I fought you every step of the way." "What happened to you in New York, Andrew? It's like I don't even know you!" I took the handle of my suitcase and started to tow it towards the parking garage. "I'll tell you all about it in the car. On the way to the hospital to see my father and sister." *** I let it all hang out as my mother started to drive, everything except my roll in the dunes with a Yale man. She was mortified when I told her that Aunt Esther had figured out my true identity, and I made sure she knew how displeased she'd been to be taken advantage of like that. "I think she took pity on me, especially after I told her that the cops wanted to arrest me, so she let me stay with her anyway. But Mom, none of this was her idea. Oh sure, once she was stuck with me living with her as a girl, she made little suggestions and bought me a few things to help me get by, but she never told me to go back to being Andrew, not once." "Then why don't you want to take off those clothes? We can get you a haircut before we go to the hospital, and cut off those nails...my God, did you get your ears pierced?" "Yep." "But why, Andrew? What's going on here? Are you telling me that you want to turn yourself into a...into a woman?" "Bingo!" *** She pulled over to the side of the road and wept. "I don't know what to think anymore....first I lose my husband and daughter, then my son has the police after him, then my husband and daughter turn up alive and she tells me she wants to spend the rest of her life as a man, and my husband agrees with her, and then my son comes home looking like a fashion model...." "Play that back for me again! Not the bit about me, what you said about Amy wanting to become a man." "You'll have to see her to believe it! Skin like leather, her hair cut so short she looks like a boy, muscles on her arms that you wouldn't believe...." "And what about Dad, what did you say just now?" "He told me that if it wasn't for your sister, he never would have made it. Apparently, he lost consciousness after two days drifting in that lifeboat, and it was your sister who spotted an island and jumped into the sea, towing the lifeboat behind her through shark infested waters. Then she found a stream and carried water back to your father in a giant leaf. After she revived him and nursed him back to health, they explored the island together and found enough food to survive until a passing ship spotted a signal flag she'd made out of the skirt she was wearing when they went overboard." "Wow. That sounds like Amy." "Your father says she's more of a man than anyone he knows," she looked at me pointedly, "and if she doesn't want to be a girl anymore, that's fine with him. At first I thought he must be delirious." She started the car back up. "I've lost my daughter, and now I'm about to lose my son." "Mom, Amy was never happy about being a girl. Aunt Esther thinks that maybe one of the reasons you made me take her place was to, I don't know, fill some void she'd left behind. Now she's back, and I'm still here, and if you think you've lost your daughter, maybe you're looking in the wrong place." My mother was silent for a long time. "Your father isn't going to like this." "No kidding! But he's got his son now, and you've got me. I love you, Mom, and I want to be the best daughter in the world, if you'll only let me." "Are you sure that's what you really want? There's a lot of baggage that comes along with being a woman." "If Amy can survive what she just went though, I can put up with the hassles of being a girl." "Your father will never stand for it." She pulled into the hospital parking garage. "Go ahead, maybe the shock of seeing you dressed like that will snap him back to his senses." With those words of encouragement, I followed her up an elevator and down a long hallway to a private room shared by my father and sister, which was unusual. When I walked in, I could scarcely believe my eyes: my sister looked like Fritz in The Swiss Family Robinson, and my father looked like Tom Hanks in Cast Away, with a long white beard and skin the color and texture of a catcher's mitt. She had nodded off, but his eyes followed me as I crossed the room to his bed and kissed him on the forehead. "Dad, I can't believe you're really alive!" "Andrew? Why are you dressed like that?" He turned to my mother. "Is this some kind of sick joke?" "Mom had nothing to do with it. Can't we talk about it later? I've missed you so much!" He sat up straight in his bed and shook his head. "I can't fucking believe it!" "Dad, please don't get mad at me, I'll try to explain...." "Explain what, that you want to dress like a girl? Go ahead, you were never half the boy your sister was. Christ, if you'd been on that ship instead of her, I'd be dead for sure." He turned to my mother again. "I know you put him up to this, to get back at me for Amy!" His voice got louder and louder, and when I looked over at my sister, she was awake and staring at me intently. "Andrew, is that you?" "Hi sis, welcome back!" I said as I took her hand, noticing that her fingernails were gnarled and cracked. All traces of femininity in her face were gone, and she stared at me with piercing blue eyes like I was a total stranger. "Why are you wearing a dress? Are those pantyhose? Omigod, did you get your ears pierced too? Yuck!" she exclaimed. "Yes, yes and yes, sister. What happened to your hair?" "I cut if off with a clam shell. What happened to yours, little brother?" The conversation went downhill from there. My father started shouting at my mother, who burst into tears, and my sister just stared at me like I was a freak show attraction. When a nurse came into the room to quiet things down, my mother took me by the arm and marched me out of the room. "Are you satisfied?" she asked bitterly. I spun away from her and walked back into the room. "Since this may be the last time we see each other for a long time, I want you all to listen to what I have to say, especially you, Amy." My mother had followed me back into the room, and they all looked at me in stunned silence. "How long have you known you wanted to be a boy?" "All my life." "Well, I didn't know I wanted to be a girl until we thought you were dead. I can't explain why it happened, but it did, and my feelings about becoming a girl are as real and strong as yours are about becoming a boy." I turned to my father. "I always knew you were disappointed in me, Dad. I was your only son and I couldn't measure up to my sister! All those hours you spent playing catch with her, all those fishing trips with her, how do you think that made me feel? Like a worthless little dweeb, and that's what I was becoming, lousy at school, always getting in trouble with the cops....some future, huh?" "As for you, Mom, can you try to imagine how I felt when you told Aunt Esther that I was dead because I was on that cruise, not Amy?" My father and sister both gasped. "And how I felt when you forced me to dress up as a girl to trick her into thinking I was Amy when she came to visit? All so she would keep sending money for her favorite niece?" More gasps, and my mother broke down with tears of shame. "That's right, dear old Aunt Esther, who was kind enough to invite Amy to stay with her in New York, except Amy happened to be me, and I couldn't refuse because the cops were after me for stealing a car!" My father was beside himself. "Why did you drag my sister into this? Our son stole a car? Why didn't you tell me?" "I couldn't tell you because you were dead!" my mother shouted. "And yes, I told your sister that Amy was alive instead of Andrew, because like us, she loved Amy more, and because without her help there was no way we were going to be able to survive!" She broke down again, and my father just stared at her in shocked silence. "Andrew, can I ask you something?" my sister asked. "What's so great about being a girl anyway?" "You should try it sometime, sister. Look, I know you should have been the boy, why is it so hard for you to understand that I want to be you?" "We all know that's impossible," my mother said. "Nope, you're wrong. If Amy wants to become a man, there's surgery and hormones that can make that happen." "That's what we were talking about, Dad," she said. "And the same goes for me, only I'll have to start taking hormones soon, before I start growing a beard and my voice changes and stuff." "Dear God," my father said. Ignoring him, I spoke only to Amy. "There's something else. Usually sex affirmation surgery for a girl who wants to become a guy is sort of limited - I mean, you'll be able to have your breasts cut off, and hormones will give you a beard and stuff, but there's not much they can do for you downstairs." "Dear God," my mother said. "But because our DNA is the same, it ought to be possible for us to switch genders completely. Reciprocal transplant surgery, they're calling it, performed on both of us, so you wind up with my penis and balls, and I'll get your womb and vagina. I'll still have to grow my own breasts, but hormones will take care of that in no time," I added. "Dear God," my parents said in unison. "Are you sure about this?" Amy asked with excitement in her voice. "Totally. There's a doctor in New York who's looking for brother and sister candidates right now. I read all about him in the...." "Now hold on, this is all moving way too fast," my father cut me off. "And how are we supposed to pay for all this?" my mother chimed in. "Are you kidding? According to today's New York Times, Dad and Amy are going to be swamped with book and movie deals. Just wait till they throw little brother-turned-sister into the saga." The three of them just stared at me. "Please think it over. If you don't want to go there, that's cool, I have a modeling career waiting for me in New York." I reached into my purse and handed Amy her old cellphone. "Here ya go, bro. If a guy named Robert calls, he's looking for me." The End