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Upon entering middle school, I had been dressing up as a girl in private for almost four years. Unfortunately, my hobby was a secret veneered by layers of false masculinity. In public, I wore clothing associated with skateboarding, rock bands, and other traditional masculine interests. Around friends, I attempted to fit the aspiring male mold that puberty would eventually produce. In most people's eyes, I was a normal, run-of-the-mill kid trying to find his place in the world. No one knew that when I put the skateboard away for the night, I exchanged my chain wallets and baggy jeans for a pair of heels and a sundress. In my small town, there had been rumors concerning my sexual orientation, but luckily, no one knew about my crossdressing hobby; however, I eventually learned it was unhealthy to keep secrets from close friends. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ After everyone in my house fell asleep, I'd spend the hours trying on dresses, skirts, tights, and anything feminine – anything considered taboo for a boy to wear. Unlike the time I spent as a male, I wasn't trying to impress anyone when I dressed up as a girl. When I picked up skateboarding, it was because other people told me it was a cool thing to do. There was an image associated with skateboarding. No one told me that crossdressing would help my popularity. In other words, I was being true to myself every time I stepped in a dress. Of course, I couldn't confide in anyone. Any time I had introduced feminine elements to my masculine wardrobe, it was met with utter contempt. Family members would berate me for applying lipstick or discipline me for painting my nails. Quickly, I learned to avert anything feminine during the daylight hours. Since expressing femininity was frowned upon, I built a masculine facade to hide behind. I opened up to no one. I became rebellious. I got into fist fights. I was miserable. Consequently, my thrills for dressing – and anything recalcitrant in nature – grew exponentially. All of my superficial masculine traits died the moment I slid a pair of panties up my legs. By the time I finished my make up and slid into a pair of heels, the facade was completely eroded. I'd walk through my laundry room like a runway mode. I'd twirl and feel the air rush up my skirt, only to stop and admire myself in the mirror, smiling the whole time. It felt so natural, I was supposed to be a girl. One night, I was tired of hiding my true self. I invited a friend to sleep over, where I asked him to play truth or dare. As he thought of a dare for me, I interjected, telling him to dare me to wear a dress. Immediately, he laughed off the best amateur galleries idea, but I persisted. I went off to the laundry room to find an outfit, and within moments, I reemerged four inches taller, my legs covered in pantyhose, and my body hugged by a tight green mini dress. My friend broke into laughter, but couldn't conceal his admiration. I pranced and posed for his pleasure, and despite his pleas for me to stop, his gaze told me otherwise. I could see his eyes locked on my legs as I sat down next to him. His laughs turned to silence, finally met with inquisition. Personally, he had no interest in crossdressing, but he admitted I pulled off women's clothing quite well. I stayed dressed as a girl the rest of the night, feeling joyful that I finally found someone I could confide in. Unfortunately, the euphoria was short lived. He moved away a month later, but not before telling our peers of my crossdressing fiasco. Perhaps he acted preemptively, worrying that I would tell others he found me attractive. Nevertheless, the word was out: I dressed as a girl in private. Despite my greatest fears being leaked, I never heard much of it. I was picked on mercilessly by people for supposedly being gay, but no one ever mentioned my crossdressing hobby. This surprised me, as I was extremely androgynous during these times (I'd frequently get mistaken to be a girl by strangers thanks to my long hair, small frame, and softspoken voice). What's more, I hit puberty much later than anyone in my school. People would pick on me for looking like a girl, but no one ever mentioned that I actually dressed like a girl in private. Thus, I thought my secret was safe. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ No matter how many layers you cover your true self in, some people can see right through them. My best friend in middle school was one of them. She didn't buy the macho facade I pathetically tried to maintain. We got along extremely well, mainly because she knew I would never try anything romantic with her. She would tell me anything and everything, because we both knew the nature of our platonic relationship. I was deep in the friend zone with her and loved that she could read me when everyone else was either missing my true personality or was too shy to point it out. At this point in my life, I had no sexual experience and had no plans for sexual activity even if it fell in my lap. I had male friends that would come on to me, but I wasn't interested. In her case, she had already lost her virginity and seemed to be exploring her sexual side. Occasionally, she dressed very provocatively and got loads of attention from men. I admired her as well, but mainly because I wanted to emulate her. Years earlier, I was introduced to the power of feminine sexuality through Victoria's Secret when I discovered a discarded catalog in my house. I was shocked to see women so scantily clad, but also, I wanted to be like them. I didn't want to wear drab clothing and walk like a tank. I wanted to flow and be graceful. I wanted to wear gentle clothing and express myself. After seeing that catalog, I was forever locked in the shackles of masculinity. Although every boy in our school desired her attention, I was the only one receiving it since I never made a pass at her. She talked to me as if I was her closest girl friend, telling me everything two girls share with one another, despite the fact I never told her I dressed up as a girl. She assumed I was gay, never knowing I had a huge crush on her. Sometimes, she would sit next to me in her miniskirt, allowing me to see everything. She viewed me as nothing more than another girl friend. My feelings for her continually grew, but I knew we would never be a couple. Mainly, she made it very clear she wasn't attracted to me. Moreover, I was so happy to have her as a friend and I didn't want to lose that. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Following reading class one day (for those of us who failed Spanish class, we were sent to reading class to brush up on our English skills), we made our route towards the second floor where our next class was. While making our way up the stairs, she sheepishly said to me, "Can I dress you up as a girl?" I was flooded with emotion. My first reaction was to scream and beg her to do so, but reality struck: There was no way I could openly express excitement for being dressed as a girl. Consequently, I acted like I didn't want it to happen. I responded with a pathetic, "no way", which she easily fought through. She knew I would submit to her will. She knew she could have her way with me. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ I arrived at her house early in the afternoon. We began the day by walking around her neighborhood, chatting about whatever the hell middle schoolers chat about. Despite her dressing conservatively, men honked their horns and made crude comments as they drove past us. Back at her house, we made our way to her room. Due to her sexual history, she was required to keep her door open. Furthermore, her younger sister had to be present with us at all times to make sure we didn't cross the line. Obviously, nothing was going to happen anyways, as she had no attraction for me and thought I was gay. I uttered a few dumb jokes after sitting on her bed, but she looked preoccupied. She seemed to have a goal in mind. I developed a combination of excitement and nervousness at the prospect of being dressed up by her. Eventually, she made her intentions clear when she started looking through her make up. She pulled out her lipstick and commanded me, "Come here." Obediently, I walked over to her desk, where she sat me down and cupped my face with her left hand. I had never seen her look so focused as she applied deep red lipstick on me. For years, I could not determine what she was feeling while applying my make up. Perhaps there was a dominant/submissive undertone to our acts, but I was too young to realize them. Yet, I was definitely seeing a different side of her. She was serious for once, as if she had been imagining what it would be like to dress me up for ages. When she was done, she took a step back and told me to purse my lips. She couldn't hide her excitement. I looked in the mirror and saw anything but a boy. Already androgynous with my long, straight hair and feminine features, the red lipstick by itself made me pass as a girl. Her little sister shouted out, "You look like a girl!" Embarrassed, I denied it, even though I knew it was true. Plus, I too, could not hide my smile after looking in the mirror. Hell, even when I denied looking like a girl, I sounded like a girl with my light voice. She continued to apply my make up as my heart raced. Funnily enough, I could feel her excitement growing as well. For me, I was finally realizing my dream. I was sharing my feminine side with someone and they actually liked it. I wasn't she if she was going to completely transform me, but my excitement overwhelmed me as my thoughts raced. I tried to make little comments to ease my tension, only to be met with hushes as she continued her focused assault on my remaining traces of masculinity. Out of the corner of my eye, I noticed a dress conspicuously draped over a chair, complimented by a bra and mary janes. Were these for me? She wouldn't of laid out her clothes for tomorrow already, right? With my make up complete, she took a step back to admire her final product. She looked content. I saw a look in her eyes I had never seen before. Often, women who have given me makeovers take a step back and smile in glee upon seeing a man transformed into a woman; with her however, she looked relieved, almost as if to say, "Everything I've been imagining has come to light. This is the true you." Having reached a new level of trust with one another, she dropped her demands and asked me if I would go and change into the dress I mentioned previously. Her tone suggested it would mean a lot to her if I did. Clearly, I was more than happy to wear her clothes and complete the transformation. Surprisingly even to myself, I dropped all pretenses of iconoclasm as I agreed to wear the dress without a hint of protest. Emerging from the restroom, she looked at me with an admiration that I had never seen from anyone. In my boy clothing, there is no chance I would have garnered such a look from her. Adding comic relief, her little sister laughed hysterically at my defenseless appearance. Although I was in a new environment and had every right to fear judgment, I felt comfortable because of her – my pillar of support. I cannot stress how important support is when trying to function as a member of the opposite sex. It takes courage to begin crossdressing – it's an act that can invite strong ridicule from one's peers. Although crossdressing is an act of individuality and unique expression, it is frowned upon due to the patriarchal society we live in. Facing the world alone while trying to be true to one's self is nearly impossible, so having her there made me feel confident. We made our ways downstairs where her family responded with glee. Her father paid little heed to me while her mother complimented my appearance with hyperbolic gasps. Her older sister – who thought I was gay based on my mannerisms – couldn't stop teasing me. She called me by a feminine version of my name, and demanded that I act like a proper lady. Worth noting, this was all in fun. Regardless, I performed a little curtsy whenever she asked for it. As we walked through her neighborhood, the initial excitement of it all calmed down. Although the novelty of it had not worn off, she was not acknowledging my new persona; rather, she was interacting with me as if she had opened up my true self. Instead of making a big deal of my appearance, it was as if she relieved me: "You're a girl now. You were always supposed to be. Finally your appearance matches your personality. Glad we got that out of the way. Let's continue building our friendship now." ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Two months later, she moved away. I wouldn't see her again for six years. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ After high school, I worked in a restaurant while attending college. I was helping a co-worker out by dropping food off at their table, when I saw her for the first time since amateur pussy thumbs middle school. We couldn't contain our enthusiasm, asking one another a barrage of questions. As it turned out, she had followed in her father's footsteps by joining the military. Currently, she was stationed overseas. I was lucky to have caught her visiting friends and family in our hometown. She would be departing in a week, but she was adamant that we hang out and catch up before then. On a sleepy weeknight, we went out for drinks at a local dive where my friend bar-tended. This meant we wouldn't be carded and would be free to enjoy one another's company. With hardly anyone at the bar, we spent the night reminiscing and filling each other in on the town's gossip. Eventually, she brought up the time she dressed me up. I hadn't dressed with another person since that time six years previously. In the meantime, I hid my true self from everyone, causing my depression to bloom. Throughout school, I was relieved to keep my crossdressing a secret, but now I understood it was unhealthy to conceal it. I was tired of hiding. I was beginning to not care what people in my town thought. I was constantly grappling with who I was and who society expected me to be. Each time I gravitated towards the latter, I sank further into depression. I knew my happiness depended on my confidence in my feminine self. I had an opportunity to let my friend know how I felt, so I let my emotions pour. I told her how much her support meant to me, how I always enjoyed expressing my feminine side with her. She was intrigued, wanting to know why I hadn't confided in her when we were friends. I explained that the societal pressures were too great, and I was too much of a coward to face my male peers. We sobered up before heading out. Before dropping her off, she asked me to drive around town so we could continue to reminisce. We passed familiar spots: the houses of old friends, parks, our old school, and so on. Recently, I had moved into a studio in an apartment complex, and she asked me amateur pussy thumbs to drive by it, karup dreams claiming she wanted to see where I lived. As we neared the complex, she asked if I had a woman's wardrobe. After telling her that I had more womens clothing than mens, she grew excited and asked to see. Without hesitation, I parked the car and we ventured inside. I showed her my vintage dresses, my cardigans, my denim jackets and scarves. I dressed to impress women, not men. Some crossdressers wear fetish outfits or revealing outfits, which is fine, but my goal has always been to pass as a woman. Plus, I love fashion. Even while dressed as a guy, I take pride in my appearance. I'll gladly spend hours searching for the right outfit. Shyly, she asked to see me dressed up, as long as I was okay with it. Of course, I was more than okay with it, so I gladly obliged. I offered her a drink while I slipped into a 50s sundress and pastel cardigan. This time, I was able to apply my make up on my own. Before I knew it, I was back in a situation I had spent years dreaming about. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Quite often, I'd lay in my bed, alone, wondering what could have been. I never wanted a romantic relationship with her, rather, I wanted her friendship and support. Many nights, I'd lay awake and dream of an alternate reality where I had the support of my best friend to dress as a girl. I imagined us exchanging clothes and having sleep overs. Most of all, I imagined myself being able to express myself regularly. I imagined myself being happy. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ The woman on my couch had changed much since her childhood. No longer conforming to gender norms, she had dropped her revealing outfits in favor of loose jeans and a hoodie; her shoes were flat, her make up removed, and her hair short. Her cisgender days were over. She looked better than ever. With each drink, our buzz became stronger, our chemistry more vivid, the distance between us shorter. We could no longer deny our attraction, evidenced by the sides of our legs pressed against each others. She placed her hand on my chin and moved in for a slow kiss. As her free hand traced the hairs on my neck, I wrapped my arms around her and brought her down with me on the couch. My excitement grew at a pace my moans couldn't stop. I wrapped my legs around her, causing my sundress to fall around my waist. Perhaps from her time in the military, she had gained muscle and was significantly stronger than me. I felt small compared to her, protected at the same time. As she pressed her pelvis against me, she asked what I wanted. I managed to moan, "I want you to fuck me." She responded by saying, "You know I can't do that." Knowing she meant this in a physical sense i.e. she doesn't have the right equipment for performing the act, I told her about my strap-on. I pulled out my box of toys and within moments, she was ready. I wrapped my legs around her as tight as possible. I wanted us to be as close as physically possible. I was clinging to her out of passion, excitement, and support. Her fucking me represented acceptance. Not only was she accepting a side of me often shunned by society, but she was attracted to it. The most I could to show her my gratitude was to pull her into me, as deep as she could go. I was extremely happy to be so comfortable playing the role of a woman during sex. Finally, I was having satisfying sex – sex where I wasn't uncomfortable playing the masculine role, attempting to dominate when every aspect of my personality screamed submissive. I was having a blissful peace of mind. Begging for closeness, begging for for acceptance, and begging for support, I hugged her as tight as possible as she penetrated me. She quieted my moans by pressing her lips tightly against mine, inserting her tongue to further suppress my noises further. Instinctively, I sucked on her tongue. I wanted every possible piece of her to be intertwined with me. I am not spiritual, but I could feel our souls uniting, and I felt had to do everything I could physically to symbolically represent this bond. Pumping faster and faster, she was now the one moaning karups hometown uncontrollably. I was shocked to see her enjoying herself so much. I knew I would enjoy sex with her, but I had no idea a woman could get so turned on fucking me. I always assumed no one would be truly interested in performing this act on me, so to have her get so turned on by it was truly surreal. I was taken aback when she lost all control of her moans. I had made women orgasm in the past, but I never heard any of them scream like this. Without touching myself, I shot a violent eruption that nestled itself in between our pressed stomachs. With both our orgasms complete, she fell on top of me from exhaustion. I stroked her hair while she rested. ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ Years passed, and although we still keep in touch through text messages and facebook, we've both moved on. She traveled the world until she fell in love with a man and married him. Eventually they settled down some three thousand miles away from where I live. In fact, we haven't seen each other face-to-face since the week I saw her – the week where she gave me the confidence to be true to myself, the confidence to never settle for anything other than my happiness. throw_away_3030