Portrait Of A Crossdresser As A Young Man free porn video

Portrait of a crossdresser as a young man By Sara Keltaine I didn't write this for others but instead as an outlet to release the demons that have haunted me since I was a child. Some might think this story funny, others might think it sad, and the people that think they know me the best would be shocked. I'm writing under a pseudonym that has become my alter ego but I will get into why's of that later. I've been told I was a happy infant and my memories of that time are unremarkable. I think this is typical but my life soon changed with a series of events I wish I could forget. My parents divorced when I was in 2nd grade and I distinctly remember it. We sat by the window in our kitchen and I cried as I knew it was my fault. Most of my memories of that day are blurry but I remember begging my mom to stay married and the tears in her eyes as she told me she had to divorce my dad. I spent much of my time in the next few months thinking of ways to get my dad back. My dad disappeared and I didn't see him for a long time. I don't remember exactly when he returned for his first visit but it felt like a year. Something else occurred in my life at that time that I remember with crystal clarity. The story might not seem like much to an adult but it was traumatizing to me and I think led to behavior that I have repeated for much of my life. I was potty trained early but as I got to kindergarten, I remember my mom's frustration as I continued to wet the bed each night. By second grade, I had the occasional dry night but most times my morning ritual included a visit to the washing machine. Every night I went to sleep, I said my prayers, and prayed for a dry night. It's hard to explain to someone who hasn't gone through it but I still remember the fear I felt as I woke in the morning to check my bed. I was sure my bedwetting was the reason my parents were no longer together and each morning's failure made me feel worse. It reached a crisis when my best friend invited me to a sleepover. I always refused in the past but he was insistent so I convinced my mom. At bedtime, his parents made a spot for me in his room and I decided I had to tell my friend about my nightly problem. We were only eight years old and in our minds, it made sense that instead I would take a blanket and sleep on the back porch. The hard wood floor wasn't very comfortable but I was ecstatic to find I woke dry. The sun wasn't up and I couldn't get back to sleep so I crossed the street and entered my house around 5am. This created panic in my friend's house that was resolved when they came to tell my mom and they found me asleep in my own bed. My friend's parents yelled at him for moving me to the back porch and he was mad at me for leaving. The next day at school, I watched as he whispered something to another of our friends. I got a bad feeling as they continued to take quick glances at me, followed by laughter. I decided to confront him but before I could get close, he pointed and shouted, "Bedwetter!" To an adult this might not sound like much but I was still reeling from my parents divorce and my best friend was announcing my shame to the whole school. A few others joined in the chant as they yelled, "Bedwetter!" I felt trapped and in those situations, animal instincts take over. Fight or flight. I wanted to beat my friend into unconsciousness but he wasn't alone and as they continued to shout, more joined the mob. "Bedwetter!" I ran. Recess was in the gym on bad weather days and as I sprinted away from my accusers, I ran around the outside of the basketball court. I was the best athlete in my class and had a big lead but the gym was enclosed and every step only encouraged more kids to join. Their cries got louder, "Bedwetter!" When it seemed like the whole gym was chasing me, I ran for the bleachers and hid underneath. The mob serenaded me with a continuous chorus of "Bedwetter!, bedwetter!, bedwetter!" I have no idea how long I was there as I cried and shook uncontrollably. I heard a teacher yelling followed by the bell that ended recess. I stayed under the bleachers and hoped she didn't see me as I didn't want to go back to class. I wanted to go home but my mom had taken a job and no one was there. I felt like dying. The teacher had no idea what had happened and asked me if I was ok but I didn't respond. When she said she was going to call the ringleaders back to the gym, I dried my eyes and told her it was nothing. She insisted and I pleaded with her to let me go. I couldn't let her investigate as it would have meant repeating my shame out loud. I went back to class and a few of my 'friends' apologized though none of us ever spoke of it again. I swore off sleepovers altogether and became a loner as I knew every kid in school now considered me a freak. I found out years later that my dad wet the bed until he was 12. To this day, he has never admitted it to me but I found out because my grandmother thought it was funny. If you don't know this, the condition that causes bed wetting is usually passed genetically from the father to son. It was just something I would need to live with longer than most. I stopped around age 10 but it would have been nice to have someone around earlier to assure me it was going to end. Instead, my self-esteem could not have been lower. I lived in a rural town of a few thousand people where everyone went to church on Sunday and I loved it. I didn't entirely understand the lessons but I loved the sense of community. My mom had gone to this church since she was a child and she loved it too. The pastor picked her to lead the choir and she was on most of the church's committees. After the divorce, everything changed. Many of the members considered divorce a sin and it didn't take long before she was removed from all church functions. She quit going altogether and instead spent Sunday mornings watching the church services on television. I continued to attend with my brother and sister in hopes that somehow our ontinued attendance could bring back the past. When our father came back into our lives we started missing church as we spent every other weekend with him. After a year of harassment for our frequent absences, we stopped going to church as well. It was during this time I started to have thoughts I couldn't explain. I knew I was born male and kept having reoccurring idea that I wished I had been born female. It is hard to describe but when I thought of myself as a girl, it gave me a feeling of joy. I didn't need to ask anyone if these thoughts were proper as my town made it quite clear how boys and girls should act. I tried to push these thoughts from my mind and certainly couldn't take a chance and let anyone know. My classmates already thought I was a freak. The church and the people in the town already hated my family. I was an outcast and I didn't want to make it worse. I realize that some reading this might see my feeling of wanting to be a girl as unresolved rage I had for my dad. It is quite possible there is some truth in this thought. All I know is what I thought at the time and that I couldn't tell anyone. After almost needing to repeat the third grade for a slate full of D's and F's, I got mostly A's and B's in the fourth. I learned to guard my actions during this time. My natural inclination was to be more effeminate and I started a practice I've continued ever since. I never volunteered to go first and always let a male classmate take the lead so I could copy him. My only place of solace was on the athletic field but even there I received taunts that I ran like a girl. We moved to a bigger town and after finding new friends, things got better. My success in sports continued and the self-esteem it gave carried me through the next few years. What I didn't understand was puberty would change everything. I'm sure puberty is tough for everyone but as the testosterone coursed through my system I went out on my first dates with girls. I bounced from girl to girl which led one of my friends to ask me if I was gay. The question struck me like a ton of bricks, as I had never considered it before. Girls got me sexually aroused and knew I had no such feelings around boys my age. His question haunted me as I always grew bored in my relationships and even the prospect of eventual sex wasn't enough to entice me. I began to notice different things about women that they ignored. All boys are fascinated with breasts but I found myself intrigued by the clothes they wore. When the girls got old enough to start wearing makeup it sent me over the edge. The feelings got so intense that I convinced my mom one day that I was sick so I could stay home from school. As soon as everyone left I went straight to my mom's room. I spent an hour putting on blush, mascara, lipstick, and eyeshadow then topped it off with one of her wigs. I put on one of her nightgowns and went into the living room where I coughed and gagged as I tried to teach myself how to smoke one of her thin cigarettes I had stole. I did this all morning then put everything back and scrubbed my face until it felt like I was going to bleed. A skeptic might say that commitment issues stemming from my parent's divorce caused my problems with girls. They might also say I was copying the strongest role model in my life. I'm sure there is a bit of truth in both statements. As my dating life continued to struggle, I stayed home more often. It wasn't long until I had learned to smoke and was even better at the makeup table which would have shocked my junior high peers that had voted me male athlete of the year. It wasn't long after that I had my first real thoughts of suicide. As a kid, I remember looking at adults and wondering why people were gay or smoked or were fat or countless other things contrary to the ideal that society dictates. The truth is there are some things we can control and some things that are a part of us. Many people are overweight because they have metabolisms that run slower. It's just the way they are made. They are predisposed to be overweight and that's the way god made them. I think the same is true for the LGBT community as well. Just like there are fat people who work out constantly to remain skinny, there are transsexuals and gays that fight their natural urges. I know from personal experience that fighting these urges can lead to some very dark places. I led two lives and it worked for me as my grades were good and my athletic success made me popular. I graduated with honors and even received a few scholarships. I was a hero to some in the community and frequently heard the comment, "You are going to go far in life" which only made my anxiety worse. They didn't know I was barely prepared emotionally for what I was about to face. College is the time when many teenagers break their bonds with the past and figure out who they are. I was terrified to find out who I was and spent much of my time getting drunk and having a one night stands. This was easy in college as commitment isn't necessary. I'm sure there were many organizations on campus that would have been great help for me but I couldn't reach out. A few girls tried to get close but I pushed them away. I couldn't take a chance to tell them my deepest thoughts for fear of rejection. I also couldn't rely on my mother's dressing room to take the edge off. My depression darkened and considering all the alcohol I drank I'm shocked I didn't kill myself. The thought of suicide was a constant companion but I graduated with decent grades and entered the workforce. Entry-level work given to all recent college graduates filled my days. At night, I found an unlikely outlet in video games. Designers gear most games to men but I will never forget the first time I played a Lara Croft title. The storyline was set up to tease boys with Lara's impossibly large breasts but I felt freedom being able to put myself in her role. It's hard to describe unless you are like me but it made me really happy. I moved from that game to an online roleplaying game where player interaction determined the story. It changed everything when I realized I could create a female character and I felt an odd joy as I did it. I created my perfect vision of a female. She was medium height with her red hair pulled back into a sporty little ponytail and green eyes that seemed to glisten. I hit the randomizer to give her a name. You can probably guess the name as it is under the title. Sara and I had many adventures but our relationship has changed over the years. Little by little, I was no longer playing a game but roleplaying a female and it liberated me. No one could see me behind the keyboard and everyone treated me like a girl. I made it very clear to all that I wasn't interested in cybersex and the server where I played was full of nice guys that didn't mind roleplaying adventures with a tomboy. In hindsight, doing this seems creepy but there wasn't any malicious intent. She became my alternate personality and soon old urges returned. I bought my first pack of women's cigarettes from the corner store and smoked during the breaks of roleplay sessions. I kidded myself my habit was like having a cigarette after making love to a woman. The real reason was much darker. It wasn't long before I was going through a pack a week which caused nicotine cravings at work. Unless you've been addicted, it is hard to describe the need for a cigarette. When you are hooked, the chemicals inside the smoke hit your lungs and rush to your extremities through your blood vessels. Nothing feels quite like a cigarette if you haven't had one in a while. If you don't smoke enough you feel an emptiness in your lungs as they ache for more. It feels similar to being hungry so many people that can't smoke replace it with eating. That's why many people complain about weight gain when they quit smoking. For me it was just the opposite. As I smoked all night, I went cold turkey at work, and I ate to cover my cravings. My reduced lung capacity and sedentary computer hobby quickly led to a weight increase. I stopped dating entirely and I focused on being Sara instead. After two years of this behavior, I knew I had to make a change. Work was getting intense and my late night sessions were affecting my job. I quit both hobbies and started working out. It took me about six months to get back into shape and while I did this, my job flourished. I became my company's fix-it-man and they promoted me a few times in rapid succession. Life was good. I spent most of my time flying around the country doing something I was good at and making a ton of money in the process. I could not fly away from my demons. It started innocently one night on the road when I had an urge for a cigarette. If you've ever smoked you know you never really quit and one night my willpower was at a low ebb. My travel schedule killed my workout routine and after I had that first one, it didn't take long for cigarettes to replace the treadmill. I won't try to explain my rationale as most obsessions don't make sense. I do have to admit that I loved that I was smoking again. The feeling of smoking once you've quit for a while is amazing and I decided I wanted to be a real smoker this time. I found a website that claimed to make you a pack a day smoker in a month. I know this sounds stupid but I'm a goal oriented person and the idea hooked me. It was only a month. I'd get to a pack a day and quit again. I'd done it before, I could do it again. The articles on the website I used weren't only about smoking. They had other articles that were darker and at first I laughed at their absurdity. I had dabbled in the past with women's makeup but these articles were talking about cross dressing. The whole web site was set up with a mantra that people should be themselves despite what society thought. If you want to smoke, be a smoker. If you were want to wear women's clothing, be a cross dresser. If you wanted to be a woman, look into transgender therapy. These weren't the only articles but these were the ones that drew my attention. As I made slow progress to my pack a day habit, I kept coming back to the articles about transgenders. Eventually I took a test that found I had many characteristics of a female. The site cautioned that no test was perfect and it encouraged readers to do more research and see a professional if the feelings got out of control. As I read other websites, I found many things that sounded a lot like me and the shame of things I'd done earlier in my life re-entered my mind. At the forefront was the period when I dressed in my mother's clothing and the website cautioned there might be further problems if I totally ignored these feelings. Their list of issues fit my life almost perfectly - lack of sleep, depression, issues with intimacy, and loneliness. It said you can fool yourself for a while but in the end, you can't fool your mind. It would be incorrect to say I had entirely quit crossdressing during the years since I left home though at the time I would have objected if someone told me that. Every Halloween I had some female friends dress me up in their clothes. I don't know what it is but many females love to do this and I was a happy test subject. When I graduated from college, I had female roommates for a while and I used their mascara and eyeliner when they weren't around. Of course, shame followed each of these sessions and I stopped when I got my own place and no longer had easy access to cosmetics. As I continued my research, things started to make more sense and it helped to know that I wasn't the only person like this. I worked up my courage and made a trip to a local grocery. I tried to hide what I was doing as I hovered in the makeup aisle looking for something I'd want to buy. I chose an eyeliner pencil that I hid among all my other groceries. I didn't dare look the cashier in the eye but I eventually realized that I was one of a thousand people they saw every day and they really didn't care what I bought. After my first purchase, every week turned into a spending spree of what I would use that weekend. I did lots of experimentation. As I got more comfortable with the confused stares of the women, I spent hours going up and down the aisles. I reminded myself I didn't need their approval, I was there for me. I've always wondered if my presence became a joke to the people manning the security cameras but I was like a kid in a candy store and I had to try everything. It helped when I found a good shop that catered exclusively to cross dressers. The woman running the place greeted me at the door and asked for my name. I started to give her my ID and she stopped me. 'No, your real name.' The emphasis on the words 'real name' made me realize what she really was asking. I told her my name was Sara Keltaine. It felt great to tell a person face to face the name I used in private. She showed me around the store and fit me with a bunch cute tops, blouses, high heels, and a wig. I had gone into the store under the pretense it was for Halloween but I'm sure she saw through my ruse. She was nice enough to go along and as I checked out, she asked if I had breast forms. I'm sure my face turned twenty shades of red at this comment. I didn't even know breast forms existed until I read about them a few weeks earlier. At the time, I laughed at the thought but as I faced the storekeeper, I didn't know what to say. She pulled some out and encouraged me to try them. Warming to the idea, my first thought was to tell her these were too small. They were B cup and like any man, I wanted at least a D. She said she'd sell me whatever I wanted but asked that I try the B first. She mentioned that in cross dressing a little goes a long way and it was usually best to use moderation unless you wanted to look like a drag queen. I considered her words as I tried them on and I swear if someone offered to attach them permanently to my body at that very moment, I would have agreed. It was as if she had returned a piece of my own body. I liked them so much I asked if I could wear them out of the store, which brought a smile to her face. She knew she'd helped someone take a big step and now she had a new loyal customer. My schedule at work continued to be hectic but I couldn't stand to be without my clothing. I started checking my suitcase at airports because security doesn't allow you to carry on liquids. I could only imagine the horror of explaining the contents of my makeup bag as hundreds of impatient travelers looked on. It would have been like 2nd grade all over again. My worst scare was when we were running late for a plane and my boss said we didn't have time to check bags. I panicked but refused him, as I knew the security X-rays would find a pouch full of items hidden in a secret compartment. After that scare, I started carrying things that wouldn't attract security like eyeliner pencils, solid lipstick and tubes of mascara that looked like a pen. My breastforms went into my suitcase and I prayed I never had to pull them out. I would have left them at home but I found I slept a lot better when I wore them. My smoking project that was supposed to last a month hit its second year. It felt good to go out on my balcony fully crossdressed and smoke a cigarette. I only did it at night and while it wasn't exactly coming out of the closet, many people could see my darkened image under the stars. I spent a lot of time out there and it felt like I had finally found my place in the world. As my feelings about crossdressing went from a place of shame to one of acceptance, a strange thing began to happen. I had never been attracted to men in my life but the more I cross dressed, the more I noticed men and my unconscious reactions now included both genders. I don't think I could go as far as to say I'm sexual attracted to men but if I lived 100% of my time as a woman I'm sure my feelings would change even more. If I replaced the testosterone in my body with estrogen, I could easily see my preference changing entirely. This realization scared me a bit and it made me wonder how our mind works. I was happy to bask in my true nature but smoking caused my weight to balloon again and I decided it was time to quit. I had only smoked brands that were considered feminine and now that I was able to crossdress in private without residual shame, I knew I didn't need to smoke anymore. It was a long journey but I knew I was on the right track. It is funny to realize in hindsight that cigarettes helped me to discover my true self but the act of smoking is self-destructive and I needed to stop. I never hit my pack a day goal. I honestly didn't try as I eventually figured out that I was only awake at home for 5 hours during the week. To smoke a pack daily meant I would need to smoke a cigarette every 15 minutes. As it takes at least 5 minutes to smoke one cigarette, I would have spent my all my time outside and it took me around an hour to properly get dressed. Even with my limited time, I found my cravings got to the point that I was going through a carton of cigarettes every other week. I did some math and figured it meant I was smoking about 12 cigarettes every night and 20 cigarettes each day on the weekends. My lungs hurt just typing that sentence as it meant I smoked a cigarette every 20 minutes. I did find when you smoke that much you don't really enjoy it but instead you are preventing a craving. Quitting cold turkey wasn't too bad. I've read that the addictive quality of nicotine is like heroin but the worst part is the first 3 days. Past that, the chemical addiction is gone but to stay smoke free means you need to stay strong against the mental urges. It's been a few years since I quit and I rarely think about it anymore but I admit I have thought about it a few times as I wrote this story about the depths of my obsession. So far I've been able to withstand it. Now that I'm older I'm at peace with how things have turned out. At one point, I considered hormones and an operation but it would have been career suicide to live full time as a woman. No one knows about my issue and I realize I have chosen a lonely road. If I were given a chance to go back in time, I'd probably goto my 12 year old self and start hormone replacement therapy. I'd have the surgery, change my name, and completely break with the past. I like to think that in an alternate universe there is a woman living happily in my place. It brings a smile to my face but I cannot change now. It always bugs me when religious people make the comment that being LGBT is a choice. Anyone who is part of this community knows they have little choice. I think many would choose to be 'normal' if they could. I would have given anything to be able to marry one of the girls I met when I was twenty. Most of my friends got married around that time and started having kids soon after. Dating for me felt like I was just going through the motions of a relationship. I knew eventually they would come to despise my disinterest and it was easier for me to push them away. Right now, I'm dating a really nice girl who doesn't want anything serious and says she never wants kids. I'm good with that though she does like to tease me that our roles are reversed. I'm still a decent athlete but low on the he-man meter but that doesn't seem to bother her. We have similar goals and for now, our relationship seems to work. If she ever changes her mind and wants more, I need to decide if I think she can handle my truth. I'd like to think I will tell her but past history makes me think I will push her away. I hope I'm wrong. To get past the emotional highs and lows that caused some of my destructive behavior, I've gone on anti-depressants and that has helped a lot. I have promised myself that if it gets bad again I'm going to see a therapist. In the past fifteen years, the thought of suicide has been a constant companion ever since it began in junior high. Now that I've found some peace I can't let myself backslide again. So far, the drugs and the freedom to crossdress have been doing the trick. When I look back on my life, I think I withdrew into myself after I faced a series of life altering situations. Things were different back then and while I'm sure most people had good intentions I'm also sure my life would be different today with a better support structure. That isn't to say that my penchant for crossdressing would be different. I believe with all my heart that I was born this way but maybe I would have had the courage to face it sooner and had a lot less angst. I'm sure there are some that would disagree with my self-diagnosis and tell me I just haven't met the right girl. They are entitled to their opinion but they don't know my pain. If you are wondering, I typed this in high heels, panty hose, and a skirt. I have on a bra with the same breast forms I bought a few years ago, a blouse that matches the skirt, and matching necklace/clip-on earrings. My face is made up with a good amount of base with dark-red lipstick and highlighted with false eyelashes, green contacts, and a moderate amount of eyeshadow, mascara, and eyeliner. It is all topped by a red-headed wig with hair that falls to my shoulders. I'm writing this on a weekend so I've lengthened my fingernails with extensions and painted them with dark-red gel. It took me awhile to adjust to using fingernail extensions but now I really like the clack of the plastic as they hit the keys on my computer. It surprises me how good I've gotten at makeup and sometimes I wish I had gone into that profession instead. I used to think that effeminate men went into that line of work to be with others like them but I wonder if part of it is because it is only job where they can be themselves. It's too bad our society isn't more open minded. I've started taking more chances and have gone outside fully dressed in the daytime. I'm aware of the dangers but the advice the lady gave in the shop has proven correct and I take pains to blend in rather than stand out. People that know me would never recognize me if I passed them on the street though I'm careful to avoid their neighborhoods. If I look in the mirror, I know that I don't pass as a woman under close inspection but I also know most don't look that close. If someone gave me the ability to change sexes tomorrow, and that's all anyone ever knew, I'd take that offer in a second. Unfortunately it doesn't work like that. I wish I had the courage to turn my back on everything for something like HRT but it isn't a miracle cure either. I'm a crossdresser and I'm at peace with that. I have to be.