When Kaylee Met Sally free porn video

I spent a long part of my life trying to figure out who the hell I was and what was wrong with me. Ever since I was a little kid in preschool, a tiny boy trying on princess dresses for dress-up and learning to fear being caught wearing one when my parents came to pick me up, I've had a thing for girl's clothing and makeup and everything feminine. I thought about it, joked about it, and feared maybe more than anything else to be forced into girls' clothes and makeup, not because it would be embarrassing but because I might have to admit the part of me that wanted it and liked it. Two halves of my personality pulled at each other at the ends: one that wanted nothing more than to get dressed up all feminine, with a particular desire to have a girl "force" me into it, while the other half shunned and repressed those thoughts as much as it could. It just felt wrong. I think in middle school I figured out that instead of just fantasizing about these desires I could probably look up girls doing makeovers on boys on youtube, and boy did I find what I was looking for. My absolute desire: I got to see boys getting terrible makeovers from their sisters and boyfriends, makeup poorly done and clothes awfully fitting, but nonetheless, boys dressed as girls. I figured out that I didn't care for drag, or anything where the boy was doing his own makeup and outfit without help - with no offense to drag queens and competent crossdressers (whose confidence and talents I greatly admire) they just didn't really do it for me. That's also how I learned to delete my internet history, when my parents called out and scolded me for these browsing habits. I remember trying to deflect the blame to a friend who came over and was actually the one interested in that kind of stuff - in retrospect, I'm sure they didn't believe the excuse, but nothing more was said of it and forever afterward I was more careful. I wondered for a long time if I was gay, although really a minimum of consideration proved that I was extremely attracted to girls and not at all to boys, so I think that idea was correctly dismissed. Maybe I was trans? I considered it for sure, after all, I was always so proud of the trans people I knew who were willing to break out of their shell and reveal who they truly were to a world which largely wouldn't accept it. But deeply, I didn't feel like a girl on the inside. I had plenty of super masculine interests and qualities too, and no part of me felt upset with the body I was born with, aside from the fact that I just wished I could dress up pretty sometimes too. I was a boy, I just had a thing for skirts. A fetish, I guess. See, when I saw a cute girl in the halls of Marcus Miller High School, I saw her tits and ass just like all the other boys (call it creepy, but that was the reality), but I also noticed her cute miniskirt and how her pretty tights just hugged her legs, and how those shoes matched perfectly. I saw how her top caressed her modest or immodest curves in just the right way. Most girls didn't wear much makeup to school, and the ones that did only did the basics since the day started at 7am and after all, it was just school, but every now and again when someone took the time to try a conspicuous lip color or a bolder eye look than usual, I noticed. I really liked it, and moreover, I envied it. As much as I wanted to be with the pretty girl and discover her body underneath the pretty clothes, I wanted to be with her while feeling those tights on my own legs, wearing that shiny pink lipgloss she rocked so well. Just as much as I wanted to get under her skirt, I wanted to get in it. You might correctly expect that my opportunities to fulfill this fantasy were limited. Turns out, despite what I had imagined, girls aren't super eager to just make a guy into a girl unless he asks, and god knows I was never going to ask. I had friends who were girls, sure, but not close ones and not all that many. Maybe if I had confidence enough to make people think it was a joke, sure, but I wasn't popular enough to do something like that as a gag. They'd think I really wanted it and liked it. I wouldn't dare. So my crossdressing adventures were limited to my imagination and internet fiction. Turns out, the bad makeover videos get kind of old and don't scratch the itch like a story does, and I read and read and read about boys forced into femininity by their mothers, girlfriends, captors, teachers, what have you. I felt gross about my weird little fetish, truly. This wasn't what men are supposed to do, I'd think. This was somehow wrong, and if god forbid anyone found out about my stupid kink I'd be mortified. Really, my wishes were ordered the following way. First, I wished I could be free of my curse, to no longer love all things girly and want them more than anything despite the world against me. Since that seemed unlikely, my second wish was exactly what you'd think. I wanted to get a pretty makeover from a pretty girl, and I wanted to get away with it without anyone knowing, or at least caring. Seems easy enough, until you try. I remember vividly the first time I was left home alone and the thought crossed my mind to sneak into moms closet and try something on. By high school, I was already much larger than her, and she also had distinct mom-fashion I didn't love, but nevertheless I carefully entered and managed to find myself a camisole and a pair of tights. This was the first time I'd actually worn anything beyond a dress over my shirt for a laugh. The feeling of nylon and fabric against my skin was intoxicating - I couldn't believe just how much softer everything was than normal boy clothes, even more so than I had imagined. Terrified of the door busting open and being caught, I migrated to the makeup table and carefully applied just a few strokes of mascara like I'd seen done online before. And then panic set in. I quickly took off the tights and cami and returned them to their original locations as closely as I could to how I found them, and raced to the other bathroom to work on un-darkening my lashes. Mom's makeup was high quality, and didn't come off easily. After scrubbing my eyes with tissues and paper towels and whatever disposable items I could find (since I had to destroy all of the evidence) I resorted to trying to pull out some of my lashes just to make them look less thick. After much effort, it worked, or at least it worked well enough to avoid suspicion. My eyes were red from scrubbing, kind of like I had cried, but no one suspected a thing when mom and dad came home. Honestly, I'm not sure if they would have noticed even if I didn't get it all off. After all, it's not like they would have been expecting it, and it's easy to miss what you don't expect. But like a drug, even raids into moms closet grew dull after a while. I had tried all of the limited amount of mom's stuff that could claim to fit me, even almost getting stuck in one absolutely terrifying experience. If that zipper on her top hadn't budged in time, my options would have been to cut the garment off or wait to be discovered. Either one, I would have rather died. I really, really wish I didn't have to spend so much mental energy on trying to get feminized, if only once. Over the years it felt like every decent chance fell through my grasp or was way too conspicuous for any comfort at all. It seemed like any time a girl would do something girly to a boy, like tie a ribbon or clip a barrette in his hair at lunch, it was always because she was flirting with him. Girls didn't flirt with me. But high school revealed a lot more to me about a changing world out there. In the early 2010's LGBT issues were becoming accepted at a far higher rate than I ever knew, and it was growing, too. I wasn't a part of the LGBT community, although my weird interest seemed to lie on the border of it. I got more brazen with half-jokes and subtle comments which threatened to give me away, but I could try to pass off as comedy. One of my favorites was whenever a girl mentioned what she would wear to a party or event or whatever. I would chime in. "Well if you wear that then one of us will have to change." Real slick. I let my guard down, but it was freeing. Little comments about fashion flew under the radar, pointers like "I'd wear blue shoes with that" to others didn't actually mean *I* would wear them. The thing is, that's exactly what I meant. By sophomore year I had it in my head that if I could just get alone with a group of girls who were friends, maybe in one of their rooms or something, inevitably someone would suggest makeovers and I'd "reluctantly" go along with it. This was easier said than done, and with my friends and opportunities I didn't exactly have many chances for that circumstance. Worse, even the one or two times it seemed to border on that kind of situation arising, no one actually brought up makeovers. Turns out, girls only suggested that kind of thing when boys weren't there. This is all just to say that I just wanted a makeover, and had no idea how to go about getting one in any way that wouldn't out me as a freak. The next great idea: bets. How hard could it be? I'd just make a bit with a girl or a guy and the penalty for my losing would be that they can do my makeup! Drop a double or nothing for a dress and we're in business. There were two problems that emerged from this. First, I had trouble coming up with an opposite side of the bet that was any good and something I genuinely wanted, and second, I always had to be the one to suggest my own eventual punishment. There's not much bite in, "Hey well if I win...uh... idk you have to do something for me, but if you win I'll dress up as a girl." That sure sounds like a boy who wants to lose, and that was my first awful misstep. Sally was a friend on mine. One year below me, we were both at the top of our respective classes and I admired her a lot. She was cute for sure - hardly 5 feet tall but athletic, with really pretty straight black hair and flawless slightly tan skin. A lot of boys had crushes on her, including myself at some point or another, but she was deeply out of my league and I had learned to go for other girls who were more achievable. After all, we were actually fairly close friends as a result of a family connection, and we had been for a while. It was with her I attempted to make a few bets, but it didn't take long for her to seem uncomfortable with it. I almost begged her to describe what she would do to me if I lost, just to fantasize, and she answered only reluctantly. I said she'd have to bake me cookies in a bikini if I won a game of chess, although it never really got shaken on and that was that. We played the game under unclear circumstances, and it wasn't very hard to win - so much so that if I had thrown it, it would have been glaringly obvious. I freed her of her unclear obligation and departed. I have to imagine she and I both wondered what really would have happened if I lost. I don't think she would have insisted on me following through with my self-declared punishment, and I wouldn't have begged for it either. It would seem far too much like I was more excited to lose than she was to win. See, the worst part I guess is that she seemed half into it. Sometimes, it struck me that she actually did want to see me in a dress, but other times, I guess when I pushed it too far, she really didn't anymore. The idea was fine, but I have to believe my eagerness to push it turned her off of the idea. Maybe if I'd suggested the makeover and just shut up I could have gotten it. I feared I'd been far too obvious. That was sophomore year, and I backed off on trying to get made over for a while. I wanted a girlfriend; then whoever she was, she could do it to me, right? Unfortunately, that was harder than expected and through a lot of heartbreaks, I finished junior year still single. Sally and I stayed friends, maybe even getting closer in that time, but I avoided bringing up any girly stuff. It wasn't worth being exposed, and I still had high school to finish, even if that meant missing my chance at a boy makeover story of my own like all the fiction I'd read online. I guess it really was just fake, or maybe there was always college? Senior year started as normal. I was swamped by schoolwork which limited the time I spent thinking about my stupid kink. I didn't mind - high performance meant I could focus on even more performance, and the rest of the time I spent with friends not worried about deep fulfillment of a fetish or whatever. Sometime around October I remember a guy friend I was talking to casually asked what I was going to wear for senior Halloween. I reacted the same way I often did: dry humor, which happened to give away more truth than they even realized. "I'm thinking a group costume, PowerPuff girls. I call Blossom, you can be Bubbles and we need to find a Buttercup," I answered without any hesitation. I cracked a smile at the joke. He laughed and brushed it off. "If you actually want to do a group thing, let me know! I have a few people who might want to get in too!" That sounded promising. I caught Sally's eye slightly down the hall, and she had a pensive look on her face. "Hey Kyler!" she started up in that bubbly way she always had. "Can I ask you something?" "Yeah of course," I replied happily, without much thought. "Well I heard your joke a moment ago and I was just wondering...could I give you a makeover?" My heart started beating out of my chest instantly. It was like my worst fear and deepest desire manifested all at once and I had to force myself to play it cool. I scanned the halls around me to see if anyone else could hear or was listening - there were people, but none who seemed to notice us. "Uh, why?" I asked, noncommittally. I didn't want to give a hard no, of course, because my heart was screaming at me to shout yes up to the heavens. I also couldn't come off too excited, either. "Well, no real reason I guess, I just think it could be kind of fun" she replied, and then continued at a softer volume, "And...I thought you might want to?" So she really was onto me those years ago. Great. How could I say yes without actually giving away how much I wanted to say yes? Plausible deniability was the name of the game here - I was allowed to do something if it was fun or funny, right? It's not weird if we don't make it weird, right? "I mean, if you really want to, I guess that's fine" I answered, trying my best to disguise my intentions. That sentence was enough to make it seem like I was just going along with her, I didn't *actually* want it. At least, that's how it seemed in my own head. "Ok!" she coyly smiled back. "Why don't you come over this weekend? My parents should both be out for most of Saturday." "Sure thing," I responded. "See you later! I'll text you!" were her last words as the warning bell rang and we went off to classes. How was I supposed to focus on anything for the rest of the day, or rest of the week for that matter? She blindsided me with this on a fucking Tuesday, and now I had to eagerly count the hours until my moment of reckoning which wouldn't come for 5 more sleepless nights. She texted me as promised after school. "Hey, so just wanted to double check we're on for Saturday, how about noon? Also, I know I just said makeover but just to verify you're a large, right?" "Yeah, I'll be there, and yeah that's right," I answered, and then rapidly deleted the text. There could be no evidence. I actually saw Sally a few times in school before Saturday, and neither of us brought up this odd forbidden arrangement we had made. She shot me a couple winks throughout the week which I could only interpret to refer to one thing. I thought as the days went on I might grow more comfortable with the idea. The opposite actually happened. Every day I wondered harder and harder if I should actually be going through with this. It was crazy, stupid, risky, whatever. What if she's planning something unkind? What if she takes pictures and they get out? How do I explain this as anything other than what it was? I really thought about calling it off. It wouldn't have been hard, just a quick, "Hey I'm actually busy Saturday," or. "I'm really not up for this like I thought it was." The first would be a lie, the second might border on truth, but it took all of my mental strength to stop defeating myself and accept that I did want to go. I really, really, wanted to go. Friday afternoon I was overcome with anxiety but fought through it. Sally sent me a reminder text just like for a doctor's appointment: "Hey Kyler, just verifying you're still coming tomorrow at noon. I can't wait for you to see what I have planned!" She had something planned? I really expected her to just wing it, but honestly it was only to my benefit that she'd already put thought into it. Maybe I'd actually come out alright. How could I turn her down at this point, especially if she'd already put work into planning? I was committed. Do or die. "Yeah, see you then," I answered straightforwardly. I still didn't want to betray my internal excitement to her. "Great, do me a favor and shave before you come." "Noted." It's not like I had much stubble, but enough to need attention every now and again. If she wanted me smooth-faced I'd arrive smooth-faced. Seemed reasonable, I thought, if I was getting a makeover after all. Friday night I hardly slept at all in anticipation. Something inside of me just felt like it was going to fall apart, like every other close brush up with success had fallen apart before. She was going to cancel, or back out, or get sick, or something divine would get in the way of my ultimate satisfaction. But somehow, nothing did. I woke up Saturday and shaved, as prescribed, and drove over to Sally's wearing my typical tee shirt and jeans combo. Maybe the whole thing was a huge gotcha, just to see if I'd really come. My hand hesitated as I knocked on the door. She was ready for me and opened it quickly, inviting me in. I took off my shoes. She wasn't wearing anything remarkable, just a casual hoodie and sweatpants, with minimal makeup but she really didn't need any anyway. "Do you want anything? A drink? A snack?" she asked. "I'll have a water if it's no bother," I answered. We walked over to the kitchen and she poured me a glass. It was like being in limbo as I drank it. We both knew why we were here. I guess I was just waiting for her signal; I definitely wasn't going to be the one to say it first. As I finished she spoke up. "So, are you ready?" "I guess," I replied with very genuine apprehension. I was completely nervous, and she could probably tell by the slight shakes of my hand. "Don't be nervous! Come on, it'll be fun. You're gonna be so pretty!" It was oddly reassuring. Usually, a boy being told he's going to be made pretty is a threat, not a kindness. She took me by the hand up the stairs and we entered her room. It wasn't particularly huge, but a pretty standard girl's bedroom with photos of her and her friends strung up on the walls, fairy lights and pink bedsheets. The walls were a very gentle light sky blue with a hint of green, almost bordering on teal. Her desk and vanity were on the same wall, on opposite sides of her bed. Across the room were her closet and the door to her own bathroom, a luxury I certainly didn't have at home. She sat me down on the bed first and sized me up. As she looked up and down, she noticed that I had freshly shaved my face as requested. "I'm assuming that's all you shaved?" she asked. "Uh...yeah," I said, not expecting the question. "That's just fine. We won't do anything permanent until next time anyway." Next time? "Ok, let's get going," she said, again taking me by the hand and instructing me to sit down at the vanity. It was a large white table with an abundance of drawers and a mirror with a ring light all around it. I wouldn't be looking there much though, as she turned me around to point away from the mirror and towards her. "Alright, no peeking!" she exclaimed, and got to work. My heart was pounding and I was hard as a rock, and I hoped she didn't notice either, although I figured she probably sensed both. To begin, she took a basic thin lilac headband and used it to push my medium-length brown hair out of my face. It had an almost comically large attached off-center grosgrain bow, the slight weight of which I felt among the small points of pressure the band pressed along my scalp. Sally then went at me with moisturizers and skin products before attacking with an array of brushes covering all different angles of my face and even a bit down my neck. My eyes were assaulted by tools and pens and wands and brushes, my cheeks dusted by a huge fluffy brush which felt like heaven, and all other implements of destruction and creation flurried around me while I sat still following her every command to open, close, tilt, pucker, or whatever else. I was the perfect model. Of course, I recognized most of the products she was using. I'd seen and read enough to know more about makeup than almost any boy my age who wasn't a budding MUA - I had all knowledge short of actual experience applying it. I really didn't expect Sally to be able to achieve much, it's not like I had the most feminine face or body around. I was thin, but defined, and I imagined my strong cheekbones and brow might be hard to disguise. "One more thing!" she announced proudly. How could I not recognize the crimson-red lipstick approaching my nervously waiting lips. I slightly opened my mouth as I looked into her eyes while she applied it. I saw focus - the face of Michelangelo completing his last strokes on the Sistine chapel. The pigment glided over my lips with a slight tug at first, but then easily on the second pass as she filled in the gaps. She finished and capped the tube, smacking her lips together at me as I had seen many times before. It was an instruction, and I mimicked her action as she cleaned up the edges lightly with a tissue and admired her final product. I started to turn around, in both fear and anticipation, but she stopped me. "Hold on - one more thing," she said. She grabbed a wig similar to my natural hair color, but much longer, and pulled it over my head, removing the headband. She brushed it behind my shoulders and straightening out the loose hairs. Finally, she turned me around. In the mirror I saw a very pretty girl, wearing no makeup, looking over the shoulder of a much closer, even prettier girl with long wavy brown hair and a face like no other. My hands came to my cheeks in surprise as I saw the girl's eyes blink in time with mine, and head turn as I moved my own. Her face was a stunning, perfectly smooth pale shade, with color brought on by a generous rosy blush and a contour which softened her masculine features into barely passably feminine ones, but passable nonetheless. When her eyes closed, bold black and gold glitter eyeshadow sent light in every which direction, radiating pure glamour, and when they opened again her eyelids disappeared behind long, dark lashes and a thin trace of eyeliner, culminating in a wing in her outer corner. On the inner corner, a bright spot of white glittery highlight grabbed attention and narrowed her nose, and the same shimmery highlighter lifted her already strong cheekbones into something out of a magazine. But stunning as her eyes were, I couldn't help but stare at her perfectly shaped, luxuriant crimson lips, painted to perfection in such a way to give a cupid's bow and sharp corners and volume in the places her natural lips otherwise failed to impress. The teenage dream girl was wearing my tee shirt. Sally wasn't just an artist, she was evidently a magician. Then, a moment of terror. "Hey Sally, we're here!" a voice called, knocking on her locked bedroom door. "YOU SAID YOUR PARENTS WERE GONE!" I angrily whispered. "Yeah, they'll be going back out soon, don't worry about it." "WHAT IF THEY COME IN HERE?" I continued. "Then we say you lost a bet and I got to do your makeup. It's really not a big deal." "IT IS A BIG DEAL!" "Kyler, relax. They won't come in, and even if they do they'll see a girl. Even if they recognize you, they won't care. We're just having fun." Would they really believe that? Sally left me behind in the room for a moment to say hi to her parents. I didn't know how to play it. Do I try to hide? It looks much worse if I hide and they see me hiding. Do I just stay here? Ultimately, paralysis won out. I sat in the chair, just waiting for my life to end, when Sally came back in, saying goodbye to her folks. It was just a stop back at home before the next round of errands. Dad had to pee. Sally's parents would be on their way again in a moment, luckily never having seen me. "Close one, huh?" she said through laughter as she reentered her room. I didn't find it nearly as funny. After a few seconds, I cracked a small smile again. "I guess you look more like a boy right now than I do," I chuckled. She agreed, but then started to speak again. "Ok Kyler, now my next question. I have some clothes for you if you're willing to wear them. You don't have to, but I think you might want to." I paused. Was there any point in deniability anymore? "Well I guess it's not really worth stopping halfway, if I'm already here." That was all the assent she needed, and got to laying out a few things. Her first idea was a short black skater skirt with rose floral pattern, and a white peasant-style top. I asked her to look away as I disrobed and put on the basic outfit. I thought it looked cute, although my makeup was a bit overdone for the ostensibly casual get up. Sally apparently thought the same and made a few mental notes as she looked me up and down. "Yeah, just as I thought," she said softly. "you don't have a lot of leg hair, but it's really enough to give it away, plus the look just doesn't quite make sense. I should have known better but I guess I got carried away with your makeup. I have something else, but it'll take a bit more effort." "Ok, hit me," I agreed. She rummaged through a drawer and pulled out a black thing and a pink thing. She didn't really expect me to wear women's underwear, right? "The dress will only fit right if you tuck your stuff back and wear these." She offered me a pair of seemingly tiny pink panties and my erection jumped just looking at it. "Yeah...about that.." she continued. "Take care of it in the bathroom and then tuck your junk between your legs as you put on the panties. That should hold well enough. Then do the tights to cover up your legs - it's cold out so even better for them." I couldn't believe what was happening. As if it wasn't enough that I had a face full of makeup, I was about to be fully dressed up as a girl at Sally's command (or at least, her offer). I was exhilarated and terrified. First, I had to do something about my, uh, problem below. I entered her bathroom. Look, I'm not huge. It's an insecurity, but I'm not so small that it doesn't show under a skirt. It felt wrong to get off in Sally's bathroom. We weren't a couple and it was just a defilement in my mind. Maybe I could just control myself and let it go down? That wasn't happening. Reluctantly, I got to business. It only took a few seconds and I took care of the evidence, flushing the toilet paper wad I'd used down the toilet. A quick cleanup and suddenly I was faced with the reality of pulling a pair of pink panties up my legs. The feeling was sensational to say the least. As I secured my unit back under and slipped the garment into place, I noticed how much of my shapely ass (if I do say so myself) remained exposed to the air. It wasn't for long, as I rolled up the mostly opaque tights in my hands and stepped in, one foot at a time, rolling the delicate nylon up my legs. I'd felt it before, but somehow this time felt so much more real than sneaking around with mom's. I emerged from the side room and Sally was pleased I'd managed to get the tights up with no issues. I guess she couldn't have been too surprised, given she'd obviously clued-in to my interest in women's things. She was ready with a bra, pink, matching my panties. It wasn't for much other than shape, and the padded b cups gave my chest a bit more shape as she clasped it in the back for me. By now, this whole process had been going on for so long that it almost didn't feel out of the ordinary anymore. "Are you ready?" she asked me, approaching the closet to get the dress. "Yes" I said, unintentionally in a slightly higher voice than normal. The dress in question was a mini crushed velvet short cap-sleeve item in a deep red, matching my lipstick perfectly I could tell already. I stepped in gently, careful not to tear the tight garment as it came over my hips and torso. Sally zipped it up for me in the back after my arms entered the short sleeves. The neckline wasn't very deep, so I didn't have to worry about the bra showing at all, but my new small breasts gave it a naturally feminine shape. For a 5'9" high school boy, I had a surprisingly good body for a girl, I was just learning. The way the short garment tugged on my ass as I turned, and how my tights seemed to resist movements were immaculate feelings of femininity, but even in this incredible outfit I knew I needed something more. Sally sensed my yearning and pulled out a box, wrapped up like a Christmas present and handed it to me. I was taken aback. "Open it!" she instructed. I sat on her bed and tore off the ribbon holding the box shut. As I removed the lid, in front of me were a pair of incredible silver satin 4" heels, with a slightly pointed toe and single short ankle strap at the top. I was in love. "These are my size?" I asked. "Try them on!" she answered. It occurred to me that she must have bought all of this stuff specifically for me, it certainly wouldn't have fit her. She knew I'd go for it, and really went all out. I loved her for that. The shoes slid onto my feet snugly but comfortably; they were perfect. I got the hang of walking in them quickly - that's what happens when you spend your whole life waiting for a moment like this. "Do you love them?" she asked. "Sally..." I could barely stammer out the words. Tears began to form in my eyes before I stifled them back. "I love it, Sally. Thank you. I can't believe how amazing I look. You're incredible." She took it to heart and gave me a big hug. While I wore the heels I must have been a solid foot taller than her, but she grabbed my waist and squeezed kindly. I leaned down to take her as well. "I knew you would! But we can't call you Kyler now can we? You need a girl name." "What about Kylie?" "Nah. Too close to your real name. Not that anyone would recognize you like this, but if someone really thought about it hard they might put it together. What about Kaylee?" "Kaylee it is," I answered. "Well Kaylee still needs a couple finishing touches before we go out," said Sally. "WHAT!" I exclaimed. "I CAN'T GO OUT LIKE THIS!" "Kaylee, look at yourself. You're beautiful and totally inconspicuous. No one would think twice of it, they'll just see a pretty and slightly overdressed girl." "You really think so? I don't believe you," I countered. "Yes I think so. And don't worry about it. We'll drive well out of time to Glenview and then no one would know you anyway. That's 40 miles away." I didn't know what to say. No part of me wanted to go out dressed like this, but I did feel like I owed Sally everything for today. "Alright. What did you have in mind?" "Let's get dinner at Giampaolo's." That was the best Italian restaurant in the state, at least some would say. It wasn't cheap, but my outfit would fit in at a place like that. "Sounds like a date?" I asked half-sarcastically. It was sarcastic, of course, if she shot it down, and only serious if she went along with it. "It's a date. Can't wait to show off my beautiful girlfriend," she cooed. Holy. Shit. This was happening. This couldn't be real. It was too much. "But hold on, we're not quite done with you," she went on. We need to do your nails first. I stood perfectly still as she coated my fingernails with a red polish matching my dress and lips. As she left it to dry, I felt her drape a small gold necklace, hardly longer than a choker, around my neck and secure it in the back - just the right delicate touch of jewelry for the look. "Alright princess, I know it's been all about you today but if we want to beat the dinner rush I'll have to get ready now so you just sit your pretty little butt there and wait now." I felt pretty. I felt really, really pretty. I knew I would love feeling pretty, and I loved feeling pretty. And maybe almost as much, I loved watching Sally undress and dress herself into something immaculately pretty too. Sally didn't need much makeup for her natural beauty, but when she wanted to it could take her to another level. Some brown shimmery eyeshadow and a red lip like mine set my heart on fire. She decided on stockings, and I watched as she drew the incredibly sheer garments up her perfectly smooth legs, connecting them to the waiting black garter belt at the top. She wore a black lace bra to match the black lace panties, similarly styled to mine although arguably sexier than even the pink. Her dress was also a mini tight thing, black silk barely reaching over the tops of her stockings, revealing them if she leaned too far one way or the other. The top of the dress was off shoulder, revealing both a good bit of her chest and daring anyone to look her way. She pulled back one side of her black hair and secured it behind her head, curling the bottoms in a way I didn't truly understand but resulting in an impossibly seductive bond- girl hairstyle I fawned over. Some black heels made the look complete I've still never felt so terrified as I did exiting her room dressed like this, despite even knowing the house was empty. She gave me a little black clutch to hold onto, containing some basic items and most importantly, my lipstick to touch up. I never would have thought of it, but Sally was so on top of things. Driving to Giampaolo's felt like I wasn't even in a dress. She drove and we talked about school, life, sports, music, whatever topic could come up. She really had a chemistry with everyone that made spending time with her amazing. This felt special, though. It was a date, after all, and I'd never dared to ask her on a real date before. I didn't think she would have gone on a date with Kyler. She seemed really glad to go with Kaylee though. We pulled into the full parking lot at around 4, and the place was already packed. "Damn it. We didn't beat the rush," she cursed. I hadn't heard her swear before. I liked it. We got out of the car to put our name in at the host station. It was a 40 minute wait. Not the worst, not great either. We took a seat together at one of the benches inside the lobby. Wouldn't you know it that two well-dressed gentlemen at the bar caught my eye just as I glanced over. I quickly looked away, almost forgetting that I was a boy in a dress in public. But it wasn't quick enough. The two guys, probably college-aged, approached Sally and me, obviously trying to subtly flex on their way over. "Hey ladies" the taller one began. "I sure hope your boyfriends haven't left you waiting here all alone." I certainly didn't know what to say. I had only been a girl for a few hours now, this was uncharted territory. I definitely wanted them to leave, fuck if I knew how to make it happen. Sally took over, though. "Sorry boys, we're taken, but I'm sure there are a couple cute girls around for you to bother somewhere else!" she said with a bright tone and smile, despite the rudeness of the statement. "Taken huh?" the second boy asked, skeptically. "Yeah!" Sally answered, and in one motion grabbed my chin in her hand and took me into a deep romantic kiss. My first, and still the best. I couldn't tell if I was tasting my lipstick or hers, but we went at it until the boys vanished and we were starting to get some looks for the aggressive PDA. She pulled away first with a huge smile on her face, and based on how her lipstick was messed up I'm sure mine was too. We retreated to the women's bathroom together and burst out laughing at what happened. I would never have believed I could attract a boy like that, actually, a decently handsome one, ever. One look in the mirror reminded me of just how not crazy it was. I looked hot, save for the lipstick I carefully repaired. Sally helped me at the end - I still wasn't sure just how she had done it so perfectly, but it was better than I could by myself. Dinner was perfect (but hideously expensive - we split the check). The ride back to her place was fun, and as I undressed from the day's activities she invited me to spend the night. Her parents were already in bed early, and would be out for church in the morning giving me time to make an escape. I scrubbed my makeup off and removed the nail polish - something I didn't want to accidentally forget. Sally told me to leave the panties on. After she had almost completely undressed, leaving only her panties on and perfect, perky boobs on full display for me, she escaped into the closet and pulled out two babydoll nightgowns in different sizes. The black one was hers, and the baby pink one, I quickly realized, was mine. With makeup off and only the skimpy lingerie remaining, I laid on top of her and lost my virginity the same night as my first kiss only hours before. I probably didn't do great. If she noticed, she pretended well enough to still make me feel good about it. I woke up before she did, and checked my phone. A few missed calls from mom reminded me that I hadn't actually told anyone my plans that day - whoops. It was probably time to get going anyway. I kissed Sally on the forehead as I arose and pulled off the nightie and panties, returning into yesterday's clothes. They felt so rough and gross compared to the pretty things I had worn on the date. I wanted them again, but I had enough composure back in me not to beg for it. I'm sure Sally would want to see Kaylee again soon enough, and she'd be there in a heartbeat for sure. Kaylee returned a few more times over the next months, but those are different stories. I finished high school that year and Sally the next, and although I went to college first, we stayed together long distance until we were reunited at State U. I took on the persona of Kaylee often in our relationship, although I believe deeply that she came to love Kyler just as much. I can do it all myself now, no help needed, although there's still nothing quite like when she does my makeup for me, and I'll do it for her. Nothing has ever quite lived up to that first makeover, but nothing ever has to. We had that experience together, and it was everything it ever needed to be. I don't know what compelled her to offer that day, or how I managed to accept, but I couldn't be happier. I intend to marry Sally once we're ready to do so. The real question in my mind, is will I be wearing a tux or a wedding dress up on that altar?